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
| 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 |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl98Ksup2.hkl Contains datablock ethyl98K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl298Ksup3.hkl Contains datablock ethyl298K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl328Ksup4.hkl Contains datablock ethyl328K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl348Ksup5.hkl Contains datablock ethyl348K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl350Ksup6.hkl Contains datablock ethyl350K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl352Ksup7.hkl Contains datablock ethyl352K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl354Ksup8.hkl Contains datablock ethyl354K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl356Ksup9.hkl Contains datablock ethyl356K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl358Ksup10.hkl Contains datablock ethyl358K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl360Ksup11.hkl Contains datablock ethyl360K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl362Ksup12.hkl Contains datablock ethyl362K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl364Ksup13.hkl Contains datablock ethyl364K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl366Ksup14.hkl Contains datablock ethyl366K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl368Ksup15.hkl Contains datablock ethyl368K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl370Ksup16.hkl Contains datablock ethyl370K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl372Ksup17.hkl Contains datablock ethyl372K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061ethyl374Ksup18.hkl Contains datablock ethyl374K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061propyl98Ksup19.hkl Contains datablock propyl98K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061propyl298Ksup20.hkl Contains datablock propyl298K |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103005792/lc0061propyl348Ksup21.hkl Contains datablock propyl348K |
| 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
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
C9H18N2O2 | F(000) = 204 |
Mr = 186.25 | Dx = 1.172 Mg m−3 |
Triclinic, P1 | Melting point: 375 K |
a = 8.7038 (14) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.204 (3) Å | Cell parameters from 4199 reflections |
c = 4.9747 (10) Å | θ = 2.3–27.5° |
α = 93.021 (11)° | µ = 0.08 mm−1 |
β = 90.616 (7)° | T = 98 K |
γ = 90.319 (10)° | Plate, colourless |
V = 527.64 (19) Å3 | 0.80 × 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 tube | Rint = 0.035 |
Graphite monochromator | θmax = 27.5°, θmin = 2.3° |
Detector resolution: 10 pixels mm-1 | h = −10→11 |
Oscillation method scans | k = −15→15 |
6068 measured reflections | l = −6→6 |
2076 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.128 | All 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 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.44032 (10) | 0.57459 (7) | 0.24164 (18) | 0.0197 (2) | |
O2 | 0.02166 (10) | 0.40706 (7) | 0.22035 (18) | 0.0195 (2) | |
N1 | 0.19696 (12) | 0.53547 (8) | 0.3825 (2) | 0.0165 (3) | |
H11 | 0.128 (2) | 0.5538 (14) | 0.506 (4) | 0.021 (4)* | |
N2 | 0.25049 (12) | 0.41607 (8) | 0.0069 (2) | 0.0167 (2) | |
H21 | 0.338 (2) | 0.4465 (14) | 0.003 (4) | 0.023 (4)* | |
C1 | 0.33545 (14) | 0.59050 (9) | 0.4018 (2) | 0.0158 (3) | |
C2 | 0.15101 (14) | 0.44889 (9) | 0.1958 (2) | 0.0162 (3) | |
C11 | 0.35090 (15) | 0.67433 (10) | 0.6398 (2) | 0.0178 (3) | |
H111 | 0.439 (2) | 0.6487 (13) | 0.745 (3) | 0.021 (4)* | |
H112 | 0.2602 (19) | 0.6735 (13) | 0.748 (3) | 0.018 (4)* | |
C12 | 0.38521 (15) | 0.79070 (10) | 0.5489 (3) | 0.0198 (3) | |
H121 | 0.405 (2) | 0.8406 (15) | 0.712 (4) | 0.027 (4)* | |
H122 | 0.4770 (19) | 0.7875 (13) | 0.445 (3) | 0.018 (4)* | |
C13 | 0.25484 (18) | 0.84117 (10) | 0.3886 (3) | 0.0260 (3) | |
H131 | 0.232 (2) | 0.7902 (16) | 0.225 (4) | 0.033 (5)* | |
C14 | 0.3084 (3) | 0.95237 (12) | 0.2891 (3) | 0.0387 (4) | |
H141 | 0.332 (2) | 1.0040 (17) | 0.440 (4) | 0.040 (5)* | |
H142 | 0.397 (3) | 0.9434 (18) | 0.175 (5) | 0.047 (6)* | |
H143 | 0.224 (3) | 0.9838 (19) | 0.185 (5) | 0.053 (6)* | |
C15 | 0.10882 (18) | 0.85613 (13) | 0.5535 (4) | 0.0354 (4) | |
H151 | 0.131 (2) | 0.9070 (17) | 0.722 (4) | 0.041 (5)* | |
H152 | 0.065 (3) | 0.7830 (19) | 0.622 (5) | 0.050 (6)* | |
H153 | 0.026 (3) | 0.8914 (19) | 0.445 (5) | 0.052 (6)* | |
C21 | 0.21377 (14) | 0.32246 (10) | −0.1823 (2) | 0.0181 (3) | |
H211 | 0.2767 (18) | 0.3308 (13) | −0.340 (3) | 0.017 (4)* | |
H212 | 0.107 (2) | 0.3260 (13) | −0.231 (3) | 0.019 (4)* | |
C22 | 0.24513 (17) | 0.21233 (11) | −0.0605 (3) | 0.0252 (3) | |
H221 | 0.355 (2) | 0.2097 (16) | −0.005 (4) | 0.039 (5)* | |
H222 | 0.179 (2) | 0.2045 (15) | 0.100 (4) | 0.033 (5)* | |
H223 | 0.221 (2) | 0.1502 (16) | −0.196 (4) | 0.037 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0159 (4) | 0.0238 (5) | 0.0191 (4) | −0.0018 (3) | 0.0033 (4) | −0.0007 (3) |
O2 | 0.0150 (4) | 0.0237 (5) | 0.0195 (4) | −0.0031 (3) | 0.0032 (3) | −0.0011 (3) |
N1 | 0.0139 (5) | 0.0198 (5) | 0.0155 (5) | −0.0004 (4) | 0.0037 (4) | −0.0015 (4) |
N2 | 0.0136 (5) | 0.0197 (5) | 0.0164 (5) | −0.0017 (4) | 0.0012 (4) | −0.0018 (4) |
C1 | 0.0158 (6) | 0.0165 (5) | 0.0154 (6) | 0.0006 (4) | −0.0010 (5) | 0.0030 (4) |
C2 | 0.0165 (6) | 0.0171 (5) | 0.0151 (5) | 0.0006 (4) | −0.0008 (4) | 0.0024 (4) |
C11 | 0.0169 (6) | 0.0210 (6) | 0.0153 (6) | −0.0003 (4) | 0.0001 (5) | −0.0010 (4) |
C12 | 0.0192 (6) | 0.0196 (6) | 0.0204 (6) | −0.0026 (4) | 0.0016 (5) | −0.0018 (4) |
C13 | 0.0374 (8) | 0.0186 (6) | 0.0215 (6) | 0.0000 (5) | −0.0086 (6) | −0.0014 (5) |
C14 | 0.0656 (12) | 0.0217 (7) | 0.0289 (8) | −0.0009 (7) | −0.0022 (8) | 0.0029 (6) |
C15 | 0.0244 (7) | 0.0270 (7) | 0.0544 (10) | 0.0034 (5) | −0.0106 (7) | −0.0002 (7) |
C21 | 0.0170 (6) | 0.0214 (6) | 0.0156 (6) | −0.0004 (4) | −0.0001 (5) | −0.0030 (4) |
C22 | 0.0274 (7) | 0.0213 (6) | 0.0267 (7) | 0.0014 (5) | 0.0014 (6) | −0.0010 (5) |
Geometric parameters (Å, º) top
O1—C1 | 1.2275 (15) | C13—C15 | 1.527 (2) |
O2—C2 | 1.2435 (15) | C13—C14 | 1.540 (2) |
N1—C1 | 1.3766 (15) | C13—H131 | 1.01 (2) |
N1—C2 | 1.4224 (15) | C14—H141 | 0.98 (2) |
N1—H11 | 0.880 (19) | C14—H142 | 0.97 (2) |
N2—C2 | 1.3321 (16) | C14—H143 | 0.99 (2) |
N2—C21 | 1.4730 (15) | C15—H151 | 1.03 (2) |
N2—H21 | 0.846 (18) | C15—H152 | 1.04 (2) |
C1—C11 | 1.5280 (16) | C15—H153 | 1.01 (3) |
C11—C12 | 1.5417 (17) | C21—C22 | 1.5280 (18) |
C11—H111 | 0.984 (18) | C21—H211 | 0.971 (16) |
C11—H112 | 0.961 (17) | C21—H212 | 0.959 (17) |
C12—C13 | 1.5304 (19) | C22—H221 | 0.99 (2) |
C12—H121 | 1.003 (18) | C22—H222 | 0.997 (19) |
C12—H122 | 0.955 (17) | C22—H223 | 1.01 (2) |
| | | |
C1—N1—C2 | 128.59 (10) | C15—C13—H131 | 109.2 (11) |
C1—N1—H11 | 116.4 (11) | C12—C13—H131 | 107.8 (11) |
C2—N1—H11 | 114.9 (11) | C14—C13—H131 | 108.1 (11) |
C2—N2—C21 | 120.62 (11) | C13—C14—H141 | 110.9 (12) |
C2—N2—H21 | 119.6 (12) | C13—C14—H142 | 110.9 (13) |
C21—N2—H21 | 119.6 (12) | H141—C14—H142 | 109.8 (18) |
O1—C1—N1 | 123.40 (11) | C13—C14—H143 | 108.6 (13) |
O1—C1—C11 | 121.49 (11) | H141—C14—H143 | 107.5 (18) |
N1—C1—C11 | 115.11 (10) | H142—C14—H143 | 109.1 (19) |
O2—C2—N2 | 123.75 (11) | C13—C15—H151 | 109.7 (11) |
O2—C2—N1 | 118.33 (11) | C13—C15—H152 | 113.7 (13) |
N2—C2—N1 | 117.90 (11) | H151—C15—H152 | 106.7 (17) |
C1—C11—C12 | 112.12 (10) | C13—C15—H153 | 110.8 (13) |
C1—C11—H111 | 104.6 (10) | H151—C15—H153 | 107.7 (18) |
C12—C11—H111 | 109.3 (9) | H152—C15—H153 | 108.0 (18) |
C1—C11—H112 | 110.2 (10) | N2—C21—C22 | 112.23 (10) |
C12—C11—H112 | 111.1 (10) | N2—C21—H211 | 106.7 (9) |
H111—C11—H112 | 109.3 (14) | C22—C21—H211 | 110.5 (9) |
C13—C12—C11 | 114.44 (11) | N2—C21—H212 | 108.5 (10) |
C13—C12—H121 | 107.3 (10) | C22—C21—H212 | 109.0 (10) |
C11—C12—H121 | 108.8 (10) | H211—C21—H212 | 109.9 (14) |
C13—C12—H122 | 110.3 (10) | C21—C22—H221 | 108.9 (12) |
C11—C12—H122 | 107.9 (9) | C21—C22—H222 | 109.5 (11) |
H121—C12—H122 | 107.8 (14) | H221—C22—H222 | 109.7 (17) |
C15—C13—C12 | 112.30 (12) | C21—C22—H223 | 110.3 (12) |
C15—C13—C14 | 110.07 (13) | H221—C22—H223 | 109.7 (17) |
C12—C13—C14 | 109.30 (13) | H222—C22—H223 | 108.7 (15) |
| | | |
C2—N1—C1—O1 | 4.1 (2) | O1—C1—C11—C12 | 58.34 (15) |
C2—N1—C1—C11 | −175.84 (11) | N1—C1—C11—C12 | −121.68 (12) |
C21—N2—C2—O2 | −2.54 (18) | C1—C11—C12—C13 | 65.93 (14) |
C21—N2—C2—N1 | 176.29 (10) | C11—C12—C13—C15 | 62.45 (15) |
C1—N1—C2—O2 | 177.05 (11) | C11—C12—C13—C14 | −175.11 (12) |
C1—N1—C2—N2 | −1.85 (19) | C2—N2—C21—C22 | −81.62 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O1i | 0.846 (18) | 2.300 (18) | 2.9778 (15) | 137.4 (16) |
N1—H11···O2ii | 0.880 (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
C9H18N2O2 | F(000) = 204 |
Mr = 186.25 | Dx = 1.109 Mg m−3 |
Triclinic, P1 | Melting point: 375 K |
a = 8.8173 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.4339 (12) Å | Cell parameters from 3690 reflections |
c = 5.0963 (1) Å | θ = 2.3–27.5° |
α = 92.912 (12)° | µ = 0.08 mm−1 |
β = 89.876 (3)° | T = 298 K |
γ = 90.152 (10)° | Plate, colourless |
V = 558.00 (6) Å3 | 0.80 × 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 tube | Rint = 0.026 |
Graphite monochromator | θmax = 27.5°, θmin = 2.3° |
Detector resolution: 10 pixels mm-1 | h = −11→11 |
Oscillation method scans | k = −16→16 |
6494 measured reflections | l = −6→6 |
2292 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.057 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.171 | H-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 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.43498 (13) | 0.57527 (10) | 0.2374 (2) | 0.0566 (3) | |
O2 | 0.02574 (12) | 0.40870 (10) | 0.2301 (2) | 0.0559 (3) | |
N1 | 0.19711 (14) | 0.53487 (11) | 0.3806 (3) | 0.0458 (3) | |
H11 | 0.1303 | 0.5546 | 0.4964 | 0.055* | |
N2 | 0.25183 (14) | 0.41611 (11) | 0.0194 (3) | 0.0467 (3) | |
H21 | 0.3377 | 0.4486 | 0.0081 | 0.056* | |
C1 | 0.33136 (17) | 0.59074 (12) | 0.3945 (3) | 0.0434 (3) | |
C2 | 0.15267 (17) | 0.44949 (12) | 0.2036 (3) | 0.0435 (3) | |
C11 | 0.34433 (19) | 0.67384 (13) | 0.6232 (3) | 0.0506 (4) | |
H111 | 0.4235 | 0.6518 | 0.7407 | 0.061* | |
H112 | 0.2497 | 0.6756 | 0.7206 | 0.061* | |
C12 | 0.3802 (2) | 0.78742 (14) | 0.5365 (4) | 0.0593 (5) | |
H122 | 0.4721 | 0.7845 | 0.4314 | 0.071* | |
H121 | 0.4003 | 0.8337 | 0.6917 | 0.071* | |
C13 | 0.2540 (3) | 0.83858 (16) | 0.3773 (4) | 0.0796 (7) | |
H131 | 0.2317 | 0.7905 | 0.2237 | 0.096* | |
C14 | 0.3089 (5) | 0.9478 (2) | 0.2795 (6) | 0.1270 (14) | |
H142 | 0.4010 | 0.9374 | 0.1807 | 0.152* | |
H141 | 0.3273 | 0.9970 | 0.4276 | 0.152* | |
H143 | 0.2326 | 0.9770 | 0.1696 | 0.152* | |
C15 | 0.1085 (3) | 0.8545 (2) | 0.5371 (8) | 0.1137 (11) | |
H152 | 0.0752 | 0.7865 | 0.5975 | 0.136* | |
H153 | 0.0313 | 0.8837 | 0.4289 | 0.136* | |
H151 | 0.1275 | 0.9034 | 0.6853 | 0.136* | |
C21 | 0.21680 (19) | 0.32495 (14) | −0.1641 (3) | 0.0521 (4) | |
H211 | 0.2769 | 0.3309 | −0.3224 | 0.062* | |
H212 | 0.1107 | 0.3281 | −0.2130 | 0.062* | |
C22 | 0.2482 (3) | 0.21723 (17) | −0.0493 (5) | 0.0752 (6) | |
H223 | 0.2233 | 0.1603 | −0.1764 | 0.090* | |
H222 | 0.1875 | 0.2102 | 0.1056 | 0.090* | |
H221 | 0.3536 | 0.2129 | −0.0045 | 0.090* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0431 (6) | 0.0655 (7) | 0.0603 (7) | −0.0078 (5) | 0.0161 (5) | −0.0055 (5) |
O2 | 0.0417 (6) | 0.0639 (7) | 0.0611 (7) | −0.0104 (5) | 0.0151 (5) | −0.0057 (5) |
N1 | 0.0388 (6) | 0.0504 (7) | 0.0478 (7) | −0.0021 (5) | 0.0119 (5) | −0.0017 (5) |
N2 | 0.0373 (6) | 0.0524 (7) | 0.0500 (7) | −0.0035 (5) | 0.0094 (5) | −0.0028 (5) |
C1 | 0.0393 (7) | 0.0459 (7) | 0.0454 (7) | 0.0009 (6) | 0.0040 (6) | 0.0075 (6) |
C2 | 0.0375 (7) | 0.0473 (8) | 0.0459 (8) | 0.0003 (5) | 0.0075 (6) | 0.0044 (6) |
C11 | 0.0484 (8) | 0.0565 (9) | 0.0464 (8) | −0.0022 (7) | 0.0016 (7) | −0.0007 (7) |
C12 | 0.0574 (10) | 0.0546 (9) | 0.0648 (10) | −0.0081 (7) | 0.0072 (8) | −0.0070 (8) |
C13 | 0.1154 (19) | 0.0504 (10) | 0.0725 (13) | 0.0025 (11) | −0.0222 (13) | −0.0023 (9) |
C14 | 0.222 (4) | 0.0612 (14) | 0.099 (2) | 0.0031 (19) | 0.000 (2) | 0.0182 (14) |
C15 | 0.0764 (17) | 0.0853 (18) | 0.179 (3) | 0.0166 (13) | −0.027 (2) | 0.0036 (19) |
C21 | 0.0456 (8) | 0.0586 (9) | 0.0512 (9) | 0.0001 (7) | 0.0038 (7) | −0.0056 (7) |
C22 | 0.0866 (15) | 0.0569 (11) | 0.0815 (14) | 0.0030 (10) | 0.0070 (12) | −0.0040 (9) |
Geometric parameters (Å, º) top
O1—C1 | 1.2227 (19) | C13—C15 | 1.526 (4) |
O2—C2 | 1.2375 (18) | C13—C14 | 1.547 (3) |
N1—C1 | 1.3710 (19) | C13—H131 | 0.9800 |
N1—C2 | 1.413 (2) | C14—H142 | 0.9600 |
N1—H11 | 0.8600 | C14—H141 | 0.9600 |
N2—C2 | 1.3328 (19) | C14—H143 | 0.9600 |
N2—C21 | 1.465 (2) | C15—H152 | 0.9600 |
N2—H21 | 0.8600 | C15—H153 | 0.9600 |
C1—C11 | 1.522 (2) | C15—H151 | 0.9600 |
C11—C12 | 1.533 (2) | C21—C22 | 1.515 (3) |
C11—H111 | 0.9700 | C21—H211 | 0.9700 |
C11—H112 | 0.9700 | C21—H212 | 0.9700 |
C12—C13 | 1.537 (3) | C22—H223 | 0.9600 |
C12—H122 | 0.9700 | C22—H222 | 0.9600 |
C12—H121 | 0.9700 | C22—H221 | 0.9600 |
| | | |
C1—N1—C2 | 129.32 (13) | C15—C13—H131 | 108.4 |
C1—N1—H11 | 115.3 | C12—C13—H131 | 108.4 |
C2—N1—H11 | 115.3 | C14—C13—H131 | 108.4 |
C2—N2—C21 | 121.00 (13) | C13—C14—H142 | 109.5 |
C2—N2—H21 | 119.5 | C13—C14—H141 | 109.5 |
C21—N2—H21 | 119.5 | H142—C14—H141 | 109.5 |
O1—C1—N1 | 123.17 (15) | C13—C14—H143 | 109.5 |
O1—C1—C11 | 121.57 (14) | H142—C14—H143 | 109.5 |
N1—C1—C11 | 115.25 (13) | H141—C14—H143 | 109.5 |
O2—C2—N2 | 123.65 (15) | C13—C15—H152 | 109.5 |
O2—C2—N1 | 118.60 (13) | C13—C15—H153 | 109.5 |
N2—C2—N1 | 117.74 (13) | H152—C15—H153 | 109.5 |
C1—C11—C12 | 113.22 (13) | C13—C15—H151 | 109.5 |
C1—C11—H111 | 108.9 | H152—C15—H151 | 109.5 |
C12—C11—H111 | 108.9 | H153—C15—H151 | 109.5 |
C1—C11—H112 | 108.9 | N2—C21—C22 | 112.64 (15) |
C12—C11—H112 | 108.9 | N2—C21—H211 | 109.1 |
H111—C11—H112 | 107.7 | C22—C21—H211 | 109.1 |
C11—C12—C13 | 114.62 (16) | N2—C21—H212 | 109.1 |
C11—C12—H122 | 108.6 | C22—C21—H212 | 109.1 |
C13—C12—H122 | 108.6 | H211—C21—H212 | 107.8 |
C11—C12—H121 | 108.6 | C21—C22—H223 | 109.5 |
C13—C12—H121 | 108.6 | C21—C22—H222 | 109.5 |
H122—C12—H121 | 107.6 | H223—C22—H222 | 109.5 |
C15—C13—C12 | 112.0 (2) | C21—C22—H221 | 109.5 |
C15—C13—C14 | 109.9 (2) | H223—C22—H221 | 109.5 |
C12—C13—C14 | 109.8 (2) | H222—C22—H221 | 109.5 |
| | | |
C2—N1—C1—O1 | 3.1 (3) | O1—C1—C11—C12 | 56.7 (2) |
C2—N1—C1—C11 | −176.24 (14) | N1—C1—C11—C12 | −123.93 (15) |
C21—N2—C2—O2 | −1.4 (2) | C1—C11—C12—C13 | 66.0 (2) |
C21—N2—C2—N1 | 177.30 (13) | C11—C12—C13—C15 | 62.9 (2) |
C1—N1—C2—O2 | 178.47 (14) | C11—C12—C13—C14 | −174.74 (19) |
C1—N1—C2—N2 | −0.3 (2) | C2—N2—C21—C22 | −82.8 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O1i | 0.86 | 2.37 | 3.0573 (17) | 137 |
N1—H11···O2ii | 0.86 | 1.99 | 2.8525 (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
C9H18N2O2 | F(000) = 204 |
Mr = 186.25 | Dx = 1.114 Mg m−3 |
Triclinic, P1 | Melting point: 375 K |
a = 8.7817 (18) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.381 (2) Å | Cell parameters from 3475 reflections |
c = 5.1113 (11) Å | θ = 2.3–27.5° |
α = 92.491 (8)° | µ = 0.08 mm−1 |
β = 90.164 (9)° | T = 328 K |
γ = 89.589 (9)° | Plate, colourless |
V = 555.17 (19) Å3 | 0.80 × 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 tube | Rint = 0.026 |
Graphite monochromator | θmax = 27.5°, θmin = 2.3° |
Detector resolution: 10 pixels mm-1 | h = −11→11 |
Oscillation method scans | k = −15→16 |
7578 measured reflections | l = −6→6 |
2169 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.162 | H 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 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.43409 (16) | 0.57524 (13) | 0.2348 (3) | 0.0691 (5) | |
O2 | 0.02639 (15) | 0.40900 (13) | 0.2335 (3) | 0.0688 (5) | |
N1 | 0.19755 (18) | 0.53428 (14) | 0.3789 (4) | 0.0565 (4) | |
H11 | 0.134 (3) | 0.5526 (18) | 0.491 (5) | 0.063 (6)* | |
N2 | 0.25155 (19) | 0.41618 (14) | 0.0232 (3) | 0.0589 (5) | |
H21 | 0.331 (3) | 0.4469 (19) | 0.017 (5) | 0.070 (7)* | |
C1 | 0.3307 (2) | 0.59059 (15) | 0.3924 (4) | 0.0537 (5) | |
C2 | 0.1534 (2) | 0.44946 (16) | 0.2065 (4) | 0.0543 (5) | |
C11 | 0.3432 (3) | 0.67318 (18) | 0.6154 (5) | 0.0641 (5) | |
H112 | 0.252 (3) | 0.676 (2) | 0.715 (5) | 0.081 (7)* | |
H111 | 0.427 (3) | 0.650 (2) | 0.729 (6) | 0.097 (9)* | |
C12 | 0.3788 (3) | 0.7864 (2) | 0.5310 (6) | 0.0760 (7) | |
H121 | 0.400 (3) | 0.842 (2) | 0.704 (6) | 0.101 (9)* | |
H122 | 0.480 (4) | 0.782 (2) | 0.415 (6) | 0.103 (9)* | |
C13 | 0.2550 (4) | 0.8377 (2) | 0.3726 (7) | 0.0996 (10) | |
H131 | 0.234 (4) | 0.790 (3) | 0.224 (8) | 0.131 (12)* | |
C14 | 0.3084 (7) | 0.9468 (3) | 0.2766 (9) | 0.1566 (19) | |
H143 | 0.2285 | 0.9790 | 0.1770 | 0.188* | |
H142 | 0.3968 | 0.9359 | 0.1683 | 0.188* | |
H141 | 0.3333 | 0.9939 | 0.4245 | 0.188* | |
C15 | 0.1083 (4) | 0.8540 (3) | 0.5295 (11) | 0.1496 (18) | |
H153 | 0.0324 | 0.8869 | 0.4228 | 0.179* | |
H151 | 0.1279 | 0.9000 | 0.6817 | 0.179* | |
H152 | 0.0725 | 0.7852 | 0.5827 | 0.179* | |
C21 | 0.2176 (3) | 0.32596 (19) | −0.1566 (5) | 0.0652 (6) | |
H212 | 0.111 (3) | 0.3305 (18) | −0.210 (5) | 0.069 (6)* | |
H211 | 0.279 (3) | 0.3354 (19) | −0.316 (5) | 0.078 (7)* | |
C22 | 0.2497 (5) | 0.2186 (2) | −0.0422 (8) | 0.0929 (9) | |
H223 | 0.229 (4) | 0.161 (3) | −0.165 (7) | 0.110 (10)* | |
H222 | 0.188 (4) | 0.209 (2) | 0.100 (7) | 0.104 (10)* | |
H221 | 0.363 (4) | 0.214 (3) | 0.001 (6) | 0.114 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0488 (7) | 0.0798 (10) | 0.0782 (10) | −0.0104 (6) | 0.0217 (7) | −0.0042 (8) |
O2 | 0.0478 (8) | 0.0781 (10) | 0.0802 (10) | −0.0124 (7) | 0.0188 (7) | −0.0034 (8) |
N1 | 0.0449 (8) | 0.0618 (10) | 0.0630 (10) | −0.0027 (7) | 0.0163 (7) | 0.0010 (8) |
N2 | 0.0429 (8) | 0.0654 (10) | 0.0683 (11) | −0.0045 (7) | 0.0120 (7) | 0.0013 (8) |
C1 | 0.0434 (9) | 0.0560 (10) | 0.0625 (11) | 0.0012 (7) | 0.0067 (8) | 0.0122 (9) |
C2 | 0.0422 (9) | 0.0583 (11) | 0.0631 (11) | 0.0002 (7) | 0.0106 (8) | 0.0099 (9) |
C11 | 0.0565 (12) | 0.0684 (13) | 0.0673 (13) | −0.0027 (10) | 0.0054 (10) | 0.0014 (10) |
C12 | 0.0675 (14) | 0.0705 (14) | 0.0896 (17) | −0.0082 (11) | 0.0109 (12) | −0.0023 (13) |
C13 | 0.133 (3) | 0.0673 (16) | 0.098 (2) | 0.0028 (16) | −0.0226 (19) | 0.0039 (15) |
C14 | 0.258 (6) | 0.080 (2) | 0.135 (3) | 0.004 (3) | 0.005 (4) | 0.030 (2) |
C15 | 0.089 (2) | 0.113 (3) | 0.247 (6) | 0.024 (2) | −0.025 (3) | 0.011 (3) |
C21 | 0.0526 (11) | 0.0728 (14) | 0.0698 (14) | −0.0016 (9) | 0.0059 (10) | −0.0026 (11) |
C22 | 0.102 (2) | 0.0703 (17) | 0.106 (2) | 0.0013 (15) | 0.0101 (19) | −0.0013 (16) |
Geometric parameters (Å, º) top
O1—C1 | 1.224 (2) | C13—C15 | 1.527 (5) |
O2—C2 | 1.236 (2) | C13—C14 | 1.534 (5) |
N1—C1 | 1.366 (2) | C13—H131 | 0.96 (4) |
N1—C2 | 1.398 (3) | C14—H143 | 0.9600 |
N1—H11 | 0.82 (3) | C14—H142 | 0.9600 |
N2—C2 | 1.325 (2) | C14—H141 | 0.9600 |
N2—C21 | 1.448 (3) | C15—H153 | 0.9600 |
N2—H21 | 0.80 (2) | C15—H151 | 0.9600 |
C1—C11 | 1.502 (3) | C15—H152 | 0.9600 |
C11—C12 | 1.519 (3) | C21—C22 | 1.500 (4) |
C11—H112 | 0.95 (3) | C21—H212 | 0.98 (2) |
C11—H111 | 0.98 (3) | C21—H211 | 0.99 (3) |
C12—C13 | 1.507 (4) | C22—H223 | 0.95 (3) |
C12—H121 | 1.12 (3) | C22—H222 | 0.92 (3) |
C12—H122 | 1.07 (3) | C22—H221 | 1.02 (4) |
| | | |
C1—N1—C2 | 129.89 (17) | C12—C13—H131 | 108 (2) |
C1—N1—H11 | 115.1 (16) | C15—C13—H131 | 108 (2) |
C2—N1—H11 | 115.0 (16) | C14—C13—H131 | 109 (2) |
C2—N2—C21 | 121.34 (18) | C13—C14—H143 | 109.5 |
C2—N2—H21 | 117.7 (18) | C13—C14—H142 | 109.5 |
C21—N2—H21 | 120.9 (18) | H143—C14—H142 | 109.5 |
O1—C1—N1 | 122.75 (19) | C13—C14—H141 | 109.5 |
O1—C1—C11 | 121.63 (18) | H143—C14—H141 | 109.5 |
N1—C1—C11 | 115.62 (17) | H142—C14—H141 | 109.5 |
O2—C2—N2 | 123.54 (19) | C13—C15—H153 | 109.5 |
O2—C2—N1 | 118.75 (17) | C13—C15—H151 | 109.5 |
N2—C2—N1 | 117.71 (17) | H153—C15—H151 | 109.5 |
C1—C11—C12 | 114.0 (2) | C13—C15—H152 | 109.5 |
C1—C11—H112 | 110.6 (15) | H153—C15—H152 | 109.5 |
C12—C11—H112 | 108.5 (16) | H151—C15—H152 | 109.5 |
C1—C11—H111 | 107.6 (17) | N2—C21—C22 | 112.8 (2) |
C12—C11—H111 | 107.6 (16) | N2—C21—H212 | 109.0 (13) |
H112—C11—H111 | 108 (2) | C22—C21—H212 | 110.1 (13) |
C13—C12—C11 | 114.6 (2) | N2—C21—H211 | 107.1 (14) |
C13—C12—H121 | 106.5 (15) | C22—C21—H211 | 111.2 (14) |
C11—C12—H121 | 111.0 (15) | H212—C21—H211 | 106 (2) |
C13—C12—H122 | 108.0 (16) | C21—C22—H223 | 111 (2) |
C11—C12—H122 | 108.2 (16) | C21—C22—H222 | 110 (2) |
H121—C12—H122 | 108 (2) | H223—C22—H222 | 107 (3) |
C12—C13—C15 | 111.8 (3) | C21—C22—H221 | 108.9 (18) |
C12—C13—C14 | 110.2 (3) | H223—C22—H221 | 106 (3) |
C15—C13—C14 | 109.5 (3) | H222—C22—H221 | 113 (3) |
| | | |
C2—N1—C1—O1 | 3.4 (3) | O1—C1—C11—C12 | 55.6 (3) |
C2—N1—C1—C11 | −176.41 (19) | N1—C1—C11—C12 | −124.7 (2) |
C21—N2—C2—O2 | −2.0 (3) | C1—C11—C12—C13 | 65.7 (3) |
C21—N2—C2—N1 | 177.44 (18) | C11—C12—C13—C15 | 63.1 (4) |
C1—N1—C2—O2 | 178.90 (19) | C11—C12—C13—C14 | −174.8 (3) |
C1—N1—C2—N2 | −0.5 (3) | C2—N2—C21—C22 | −82.2 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O1i | 0.80 (2) | 2.44 (3) | 3.067 (2) | 136 (2) |
N1—H11···O2ii | 0.82 (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
C9H18N2O2 | F(000) = 204 |
Mr = 186.25 | Dx = 1.113 Mg m−3 |
Triclinic, P1 | Melting point: 375 K |
a = 8.740 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.357 (2) Å | Cell parameters from 2704 reflections |
c = 5.1473 (12) Å | θ = 1.7–26.9° |
α = 91.509 (8)° | µ = 0.08 mm−1 |
β = 90.236 (11)° | T = 348 K |
γ = 89.525 (13)° | Plate, colourless |
V = 555.7 (2) Å3 | 0.80 × 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 tube | Rint = 0.036 |
Graphite monochromator | θmax = 27.5°, θmin = 2.3° |
Detector resolution: 10 pixels mm-1 | h = −10→10 |
Oscillation method scans | k = −15→15 |
6205 measured reflections | l = −6→6 |
1939 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.082 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.255 | H-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 parameters | Δρmax = 0.27 e Å−3 |
5 restraints | Δρmin = −0.21 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.4329 (2) | 0.5747 (2) | 0.2314 (5) | 0.0846 (7) | |
O2 | 0.0266 (2) | 0.4099 (2) | 0.2382 (5) | 0.0837 (7) | |
N1 | 0.1972 (3) | 0.5337 (2) | 0.3770 (5) | 0.0701 (7) | |
H11 | 0.1302 | 0.5530 | 0.4913 | 0.084* | |
N2 | 0.2522 (3) | 0.4162 (2) | 0.0286 (5) | 0.0732 (7) | |
H21 | 0.3388 | 0.4483 | 0.0170 | 0.088* | |
C1 | 0.3299 (3) | 0.5903 (2) | 0.3881 (6) | 0.0684 (8) | |
C2 | 0.1534 (3) | 0.4499 (3) | 0.2098 (6) | 0.0689 (8) | |
C11 | 0.3418 (4) | 0.6722 (3) | 0.6063 (7) | 0.0805 (9) | |
H112 | 0.4210 | 0.6488 | 0.7254 | 0.097* | |
H111 | 0.2459 | 0.6740 | 0.7005 | 0.097* | |
C12 | 0.3776 (5) | 0.7849 (3) | 0.5237 (9) | 0.1003 (12) | |
H122 | 0.4711 | 0.7827 | 0.4229 | 0.120* | |
H121 | 0.3961 | 0.8299 | 0.6777 | 0.120* | |
C13 | 0.2532 (6) | 0.8367 (4) | 0.3649 (10) | 0.1236 (17) | |
H131 | 0.2302 | 0.7897 | 0.2137 | 0.148* | |
C14 | 0.3071 (11) | 0.9462 (5) | 0.2717 (15) | 0.196 (4) | |
H143 | 0.2280 | 0.9787 | 0.1692 | 0.235* | |
H142 | 0.3975 | 0.9361 | 0.1682 | 0.235* | |
H141 | 0.3298 | 0.9926 | 0.4192 | 0.235* | |
C15 | 0.1075 (6) | 0.8540 (5) | 0.5253 (17) | 0.185 (3) | |
H152 | 0.0729 | 0.7856 | 0.5861 | 0.222* | |
H153 | 0.0294 | 0.8857 | 0.4191 | 0.222* | |
H151 | 0.1287 | 0.9015 | 0.6714 | 0.222* | |
C21 | 0.2180 (4) | 0.3277 (3) | −0.1486 (7) | 0.0808 (9) | |
H211 | 0.2786 | 0.3345 | −0.3046 | 0.097* | |
H212 | 0.1109 | 0.3317 | −0.1981 | 0.097* | |
C22 | 0.2497 (6) | 0.2198 (3) | −0.0343 (10) | 0.1109 (14) | |
H223 | 0.2247 | 0.1635 | −0.1591 | 0.133* | |
H222 | 0.1887 | 0.2120 | 0.1187 | 0.133* | |
H221 | 0.3561 | 0.2145 | 0.0110 | 0.133* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0539 (12) | 0.0981 (16) | 0.1021 (16) | −0.0133 (10) | 0.0244 (11) | −0.0008 (13) |
O2 | 0.0553 (13) | 0.0932 (15) | 0.1029 (17) | −0.0144 (10) | 0.0238 (11) | −0.0022 (13) |
N1 | 0.0513 (13) | 0.0771 (15) | 0.0822 (16) | −0.0061 (11) | 0.0199 (11) | 0.0039 (13) |
N2 | 0.0508 (13) | 0.0810 (16) | 0.0878 (17) | −0.0061 (11) | 0.0168 (12) | 0.0008 (14) |
C1 | 0.0514 (15) | 0.0752 (17) | 0.0796 (19) | −0.0018 (12) | 0.0091 (13) | 0.0186 (15) |
C2 | 0.0480 (15) | 0.0787 (18) | 0.0809 (19) | −0.0023 (12) | 0.0141 (13) | 0.0139 (15) |
C11 | 0.0653 (19) | 0.084 (2) | 0.092 (2) | −0.0069 (15) | 0.0076 (16) | 0.0038 (18) |
C12 | 0.085 (3) | 0.095 (3) | 0.121 (3) | −0.013 (2) | 0.016 (2) | −0.004 (2) |
C13 | 0.157 (5) | 0.094 (3) | 0.120 (4) | 0.001 (3) | −0.020 (3) | 0.011 (3) |
C14 | 0.299 (11) | 0.105 (4) | 0.186 (7) | −0.006 (5) | 0.006 (7) | 0.048 (4) |
C15 | 0.102 (4) | 0.143 (5) | 0.312 (10) | 0.027 (3) | −0.020 (5) | 0.028 (6) |
C21 | 0.0619 (19) | 0.092 (2) | 0.089 (2) | −0.0042 (15) | 0.0082 (16) | 0.0021 (18) |
C22 | 0.115 (3) | 0.086 (3) | 0.131 (4) | 0.001 (2) | 0.007 (3) | 0.004 (2) |
Geometric parameters (Å, º) top
O1—C1 | 1.222 (4) | C13—C14 | 1.526 (8) |
O2—C2 | 1.228 (3) | C13—C15 | 1.531 (9) |
N1—C1 | 1.359 (4) | C13—H131 | 0.9800 |
N1—C2 | 1.385 (4) | C14—H143 | 0.9600 |
N1—H11 | 0.8600 | C14—H142 | 0.9600 |
N2—C2 | 1.330 (4) | C14—H141 | 0.9600 |
N2—C21 | 1.439 (4) | C15—H152 | 0.9600 |
N2—H21 | 0.8600 | C15—H153 | 0.9600 |
C1—C11 | 1.496 (5) | C15—H151 | 0.9600 |
C11—C12 | 1.503 (5) | C21—C22 | 1.495 (5) |
C11—H112 | 0.9700 | C21—H211 | 0.9700 |
C11—H111 | 0.9700 | C21—H212 | 0.9700 |
C12—C13 | 1.506 (7) | C22—H223 | 0.9600 |
C12—H122 | 0.9700 | C22—H222 | 0.9600 |
C12—H121 | 0.9700 | C22—H221 | 0.9600 |
| | | |
C1—N1—C2 | 129.9 (3) | C12—C13—H131 | 109.1 |
C1—N1—H11 | 115.1 | C14—C13—H131 | 109.1 |
C2—N1—H11 | 115.1 | C15—C13—H131 | 109.1 |
C2—N2—C21 | 121.7 (3) | C13—C14—H143 | 109.5 |
C2—N2—H21 | 119.2 | C13—C14—H142 | 109.5 |
C21—N2—H21 | 119.2 | H143—C14—H142 | 109.5 |
O1—C1—N1 | 122.3 (3) | C13—C14—H141 | 109.5 |
O1—C1—C11 | 122.2 (3) | H143—C14—H141 | 109.5 |
N1—C1—C11 | 115.5 (3) | H142—C14—H141 | 109.5 |
O2—C2—N2 | 123.6 (3) | C13—C15—H152 | 109.5 |
O2—C2—N1 | 118.4 (3) | C13—C15—H153 | 109.5 |
N2—C2—N1 | 118.0 (3) | H152—C15—H153 | 109.5 |
C1—C11—C12 | 114.6 (3) | C13—C15—H151 | 109.5 |
C1—C11—H112 | 108.6 | H152—C15—H151 | 109.5 |
C12—C11—H112 | 108.6 | H153—C15—H151 | 109.5 |
C1—C11—H111 | 108.6 | N2—C21—C22 | 112.6 (3) |
C12—C11—H111 | 108.6 | N2—C21—H211 | 109.1 |
H112—C11—H111 | 107.6 | C22—C21—H211 | 109.1 |
C11—C12—C13 | 114.1 (3) | N2—C21—H212 | 109.1 |
C11—C12—H122 | 108.7 | C22—C21—H212 | 109.1 |
C13—C12—H122 | 108.7 | H211—C21—H212 | 107.8 |
C11—C12—H121 | 108.7 | C21—C22—H223 | 109.5 |
C13—C12—H121 | 108.7 | C21—C22—H222 | 109.5 |
H122—C12—H121 | 107.6 | H223—C22—H222 | 109.5 |
C12—C13—C14 | 109.6 (5) | C21—C22—H221 | 109.5 |
C12—C13—C15 | 111.0 (4) | H223—C22—H221 | 109.5 |
C14—C13—C15 | 108.8 (5) | H222—C22—H221 | 109.5 |
| | | |
C2—N1—C1—O1 | 3.0 (5) | O1—C1—C11—C12 | 55.3 (4) |
C2—N1—C1—C11 | −176.5 (3) | N1—C1—C11—C12 | −125.3 (3) |
C21—N2—C2—O2 | −1.0 (5) | C1—C11—C12—C13 | 65.7 (5) |
C21—N2—C2—N1 | 178.3 (3) | C11—C12—C13—C14 | −175.0 (4) |
C1—N1—C2—O2 | 179.3 (3) | C11—C12—C13—C15 | 64.8 (6) |
C1—N1—C2—N2 | 0.1 (5) | C2—N2—C21—C22 | −82.8 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O1i | 0.86 | 2.39 | 3.069 (3) | 137 |
N1—H11···O2ii | 0.86 | 2.00 | 2.859 (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
C9H18N2O2 | F(000) = 204 |
Mr = 186.25 | Dx = 1.107 Mg m−3 |
Triclinic, P1 | Melting point: 375 K |
a = 8.7514 (15) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.460 (2) Å | Cell parameters from 4431 reflections |
c = 5.1254 (9) Å | θ = 2.9–27.4° |
α = 91.510 (5)° | µ = 0.08 mm−1 |
β = 90.273 (9)° | T = 350 K |
γ = 89.642 (8)° | Plate, colourless |
V = 558.69 (16) Å3 | 0.80 × 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 tube | Rint = 0.021 |
Graphite monochromator | θmax = 27.5°, θmin = 2.3° |
Detector resolution: 10 pixels mm-1 | h = −11→11 |
Oscillation method scans | k = −16→16 |
6495 measured reflections | l = −6→6 |
2118 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.120 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.250 | H-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 parameters | Δρmax = 0.20 e Å−3 |
6 restraints | Δρmin = −0.22 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.4331 (3) | 0.5744 (2) | 0.2313 (6) | 0.0800 (9) | |
O2 | 0.0270 (3) | 0.4095 (2) | 0.2386 (6) | 0.0797 (9) | |
N1 | 0.1970 (3) | 0.5338 (3) | 0.3786 (7) | 0.0657 (9) | |
H11 | 0.1304 | 0.5529 | 0.4939 | 0.079* | |
N2 | 0.2526 (4) | 0.4162 (3) | 0.0302 (7) | 0.0683 (9) | |
H12 | 0.3392 | 0.4478 | 0.0190 | 0.082* | |
C1 | 0.3300 (4) | 0.5901 (3) | 0.3871 (8) | 0.0623 (10) | |
C2 | 0.1535 (4) | 0.4499 (3) | 0.2105 (8) | 0.0633 (10) | |
C11 | 0.3413 (5) | 0.6722 (3) | 0.6048 (9) | 0.0775 (12) | |
H112 | 0.4203 | 0.6496 | 0.7252 | 0.093* | |
H111 | 0.2453 | 0.6739 | 0.6988 | 0.093* | |
C12 | 0.3767 (6) | 0.7844 (4) | 0.5202 (11) | 0.1012 (17) | |
H122 | 0.3968 | 0.8289 | 0.6746 | 0.121* | |
H121 | 0.4694 | 0.7820 | 0.4172 | 0.121* | |
C13 | 0.2530 (8) | 0.8371 (5) | 0.3637 (13) | 0.123 (2) | |
H131 | 0.2292 | 0.7913 | 0.2107 | 0.148* | |
C14 | 0.3071 (13) | 0.9459 (5) | 0.2724 (18) | 0.201 (5) | |
H143 | 0.2277 | 0.9788 | 0.1718 | 0.242* | |
H142 | 0.3966 | 0.9362 | 0.1666 | 0.242* | |
H141 | 0.3310 | 0.9911 | 0.4214 | 0.242* | |
C15 | 0.1083 (8) | 0.8548 (7) | 0.523 (2) | 0.192 (4) | |
H152 | 0.0741 | 0.7873 | 0.5872 | 0.230* | |
H153 | 0.0301 | 0.8852 | 0.4154 | 0.230* | |
H151 | 0.1294 | 0.9030 | 0.6681 | 0.230* | |
C21 | 0.2183 (5) | 0.3279 (4) | −0.1466 (9) | 0.0788 (12) | |
H211 | 0.2785 | 0.3348 | −0.3037 | 0.095* | |
H212 | 0.1113 | 0.3317 | −0.1959 | 0.095* | |
C22 | 0.2505 (7) | 0.2204 (4) | −0.0324 (12) | 0.1091 (18) | |
H223 | 0.2262 | 0.1647 | −0.1586 | 0.131* | |
H222 | 0.1891 | 0.2121 | 0.1205 | 0.131* | |
H221 | 0.3567 | 0.2155 | 0.0141 | 0.131* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0511 (15) | 0.095 (2) | 0.094 (2) | −0.0123 (14) | 0.0241 (15) | −0.0030 (17) |
O2 | 0.0525 (16) | 0.092 (2) | 0.095 (2) | −0.0142 (14) | 0.0228 (14) | −0.0050 (17) |
N1 | 0.0484 (17) | 0.073 (2) | 0.076 (2) | −0.0032 (14) | 0.0209 (15) | −0.0020 (17) |
N2 | 0.0504 (17) | 0.074 (2) | 0.080 (2) | −0.0057 (15) | 0.0134 (16) | −0.0016 (18) |
C1 | 0.049 (2) | 0.067 (2) | 0.072 (2) | 0.0016 (17) | 0.0082 (18) | 0.0141 (19) |
C2 | 0.0451 (19) | 0.071 (2) | 0.075 (3) | 0.0033 (17) | 0.0150 (18) | 0.010 (2) |
C11 | 0.064 (3) | 0.082 (3) | 0.087 (3) | −0.006 (2) | 0.010 (2) | 0.004 (2) |
C12 | 0.087 (4) | 0.097 (4) | 0.120 (4) | −0.012 (3) | 0.026 (3) | −0.005 (3) |
C13 | 0.145 (6) | 0.105 (4) | 0.120 (5) | 0.005 (4) | −0.020 (4) | 0.015 (4) |
C14 | 0.316 (14) | 0.098 (5) | 0.192 (9) | −0.006 (7) | 0.019 (9) | 0.047 (6) |
C15 | 0.109 (6) | 0.147 (7) | 0.321 (14) | 0.029 (5) | −0.021 (7) | 0.029 (8) |
C21 | 0.060 (2) | 0.092 (3) | 0.084 (3) | −0.003 (2) | 0.010 (2) | −0.001 (3) |
C22 | 0.114 (4) | 0.086 (4) | 0.127 (5) | 0.002 (3) | 0.010 (4) | −0.001 (3) |
Geometric parameters (Å, º) top
O1—C1 | 1.219 (4) | C13—C15 | 1.523 (11) |
O2—C2 | 1.230 (4) | C13—C14 | 1.524 (10) |
N1—C1 | 1.362 (5) | C13—H131 | 0.9800 |
N1—C2 | 1.391 (5) | C14—H143 | 0.9600 |
N1—H11 | 0.8600 | C14—H142 | 0.9600 |
N2—C2 | 1.329 (5) | C14—H141 | 0.9600 |
N2—C21 | 1.438 (5) | C15—H152 | 0.9600 |
N2—H12 | 0.8600 | C15—H153 | 0.9600 |
C1—C11 | 1.496 (6) | C15—H151 | 0.9600 |
C11—C12 | 1.510 (7) | C21—C22 | 1.501 (7) |
C11—H112 | 0.9700 | C21—H211 | 0.9700 |
C11—H111 | 0.9700 | C21—H212 | 0.9700 |
C12—C13 | 1.502 (9) | C22—H223 | 0.9600 |
C12—H122 | 0.9700 | C22—H222 | 0.9600 |
C12—H121 | 0.9700 | C22—H221 | 0.9600 |
| | | |
C1—N1—C2 | 129.3 (3) | C12—C13—H131 | 109.0 |
C1—N1—H11 | 115.3 | C15—C13—H131 | 109.0 |
C2—N1—H11 | 115.3 | C14—C13—H131 | 109.0 |
C2—N2—C21 | 121.6 (3) | C13—C14—H143 | 109.5 |
C2—N2—H12 | 119.2 | C13—C14—H142 | 109.5 |
C21—N2—H12 | 119.2 | H143—C14—H142 | 109.5 |
O1—C1—N1 | 122.8 (4) | C13—C14—H141 | 109.5 |
O1—C1—C11 | 122.3 (4) | H143—C14—H141 | 109.5 |
N1—C1—C11 | 115.0 (3) | H142—C14—H141 | 109.5 |
O2—C2—N2 | 123.3 (4) | C13—C15—H152 | 109.5 |
O2—C2—N1 | 118.7 (3) | C13—C15—H153 | 109.5 |
N2—C2—N1 | 118.0 (3) | H152—C15—H153 | 109.5 |
C1—C11—C12 | 114.8 (4) | C13—C15—H151 | 109.5 |
C1—C11—H112 | 108.6 | H152—C15—H151 | 109.5 |
C12—C11—H112 | 108.6 | H153—C15—H151 | 109.5 |
C1—C11—H111 | 108.6 | N2—C21—C22 | 113.1 (4) |
C12—C11—H111 | 108.6 | N2—C21—H211 | 109.0 |
H112—C11—H111 | 107.5 | C22—C21—H211 | 109.0 |
C13—C12—C11 | 115.0 (4) | N2—C21—H212 | 109.0 |
C13—C12—H122 | 108.5 | C22—C21—H212 | 109.0 |
C11—C12—H122 | 108.5 | H211—C21—H212 | 107.8 |
C13—C12—H121 | 108.5 | C21—C22—H223 | 109.5 |
C11—C12—H121 | 108.5 | C21—C22—H222 | 109.5 |
H122—C12—H121 | 107.5 | H223—C22—H222 | 109.5 |
C12—C13—C15 | 111.6 (6) | C21—C22—H221 | 109.5 |
C12—C13—C14 | 110.0 (6) | H223—C22—H221 | 109.5 |
C15—C13—C14 | 108.2 (7) | H222—C22—H221 | 109.5 |
| | | |
C2—N1—C1—O1 | 2.3 (7) | O1—C1—C11—C12 | 55.4 (6) |
C2—N1—C1—C11 | −176.9 (4) | N1—C1—C11—C12 | −125.3 (4) |
C21—N2—C2—O2 | −0.4 (6) | C1—C11—C12—C13 | 66.8 (6) |
C21—N2—C2—N1 | 178.3 (4) | C11—C12—C13—C15 | 64.3 (7) |
C1—N1—C2—O2 | 179.4 (4) | C11—C12—C13—C14 | −175.6 (5) |
C1—N1—C2—N2 | 0.7 (6) | C2—N2—C21—C22 | −83.5 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H12···O1i | 0.86 | 2.39 | 3.070 (4) | 137 |
N1—H11···O2ii | 0.86 | 1.99 | 2.853 (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
C9H18N2O2 | F(000) = 204 |
Mr = 186.25 | Dx = 1.116 Mg m−3 |
Triclinic, P1 | Melting point: 375 K |
a = 8.7503 (15) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.4205 (13) Å | Cell parameters from 2561 reflections |
c = 5.0998 (3) Å | θ = 1.6–27.2° |
α = 90.921 (8)° | µ = 0.08 mm−1 |
β = 89.723 (12)° | T = 352 K |
γ = 89.714 (10)° | Plate, colourless |
V = 554.18 (12) Å3 | 0.80 × 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 tube | Rint = 0.043 |
Graphite monochromator | θmax = 27.5°, θmin = 2.8° |
Detector resolution: 10 pixels mm-1 | h = −11→11 |
Oscillation method scans | k = −16→16 |
6495 measured reflections | l = −6→6 |
1968 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.109 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.357 | H-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 parameters | Δρmax = 0.25 e Å−3 |
5 restraints | Δρmin = −0.27 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.4334 (3) | 0.5747 (3) | 0.2302 (6) | 0.0916 (10) | |
O2 | 0.0271 (3) | 0.4095 (2) | 0.2407 (6) | 0.0884 (10) | |
N1 | 0.1975 (4) | 0.5334 (3) | 0.3774 (6) | 0.0736 (10) | |
H11 | 0.1306 | 0.5514 | 0.4943 | 0.088* | |
N2 | 0.2528 (4) | 0.4164 (3) | 0.0297 (6) | 0.0762 (10) | |
H21 | 0.3397 | 0.4480 | 0.0171 | 0.091* | |
C1 | 0.3279 (4) | 0.5905 (3) | 0.3858 (8) | 0.0713 (10) | |
C2 | 0.1544 (5) | 0.4503 (3) | 0.2098 (8) | 0.0745 (10) | |
C11 | 0.3418 (5) | 0.6719 (3) | 0.6031 (9) | 0.0841 (12) | |
H112 | 0.4200 | 0.6475 | 0.7228 | 0.101* | |
H111 | 0.2460 | 0.6746 | 0.6992 | 0.101* | |
C12 | 0.3806 (6) | 0.7842 (4) | 0.5206 (11) | 0.1075 (17) | |
H122 | 0.4733 | 0.7820 | 0.4156 | 0.129* | |
H121 | 0.4004 | 0.8281 | 0.6756 | 0.129* | |
C13 | 0.2535 (8) | 0.8365 (5) | 0.3631 (12) | 0.131 (2) | |
H131 | 0.2308 | 0.7903 | 0.2109 | 0.157* | |
C14 | 0.3088 (15) | 0.9449 (6) | 0.2663 (19) | 0.220 (6) | |
H142 | 0.4007 | 0.9348 | 0.1651 | 0.264* | |
H141 | 0.3291 | 0.9916 | 0.4139 | 0.264* | |
H143 | 0.2315 | 0.9768 | 0.1589 | 0.264* | |
C15 | 0.1084 (8) | 0.8520 (7) | 0.524 (2) | 0.188 (4) | |
H152 | 0.0739 | 0.7835 | 0.5849 | 0.225* | |
H153 | 0.0308 | 0.8839 | 0.4178 | 0.225* | |
H151 | 0.1289 | 0.8984 | 0.6722 | 0.225* | |
C21 | 0.2191 (5) | 0.3275 (4) | −0.1474 (9) | 0.0883 (13) | |
H211 | 0.2798 | 0.3347 | −0.3057 | 0.106* | |
H212 | 0.1122 | 0.3313 | −0.1964 | 0.106* | |
C22 | 0.2506 (8) | 0.2200 (4) | −0.0318 (13) | 0.1205 (19) | |
H223 | 0.2263 | 0.1644 | −0.1575 | 0.145* | |
H222 | 0.1890 | 0.2115 | 0.1227 | 0.145* | |
H221 | 0.3567 | 0.2150 | 0.0136 | 0.145* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0625 (17) | 0.104 (2) | 0.108 (2) | −0.0180 (14) | 0.0261 (15) | −0.0071 (17) |
O2 | 0.0576 (17) | 0.101 (2) | 0.106 (2) | −0.0170 (13) | 0.0298 (14) | −0.0096 (16) |
N1 | 0.0580 (18) | 0.081 (2) | 0.0813 (19) | −0.0088 (14) | 0.0220 (14) | −0.0016 (16) |
N2 | 0.0542 (18) | 0.085 (2) | 0.089 (2) | −0.0068 (14) | 0.0168 (15) | −0.0017 (17) |
C1 | 0.0460 (18) | 0.081 (2) | 0.087 (2) | 0.0021 (15) | 0.0141 (15) | 0.017 (2) |
C2 | 0.055 (2) | 0.082 (2) | 0.086 (2) | −0.0021 (16) | 0.0158 (17) | 0.010 (2) |
C11 | 0.071 (3) | 0.082 (2) | 0.098 (3) | −0.0082 (19) | 0.010 (2) | 0.004 (2) |
C12 | 0.084 (3) | 0.103 (4) | 0.135 (4) | −0.012 (3) | 0.024 (3) | −0.009 (3) |
C13 | 0.162 (7) | 0.108 (4) | 0.123 (5) | 0.003 (4) | −0.011 (4) | 0.011 (3) |
C14 | 0.34 (2) | 0.125 (6) | 0.193 (9) | 0.002 (7) | 0.005 (10) | 0.047 (6) |
C15 | 0.105 (6) | 0.165 (7) | 0.294 (12) | 0.022 (5) | −0.012 (7) | 0.029 (7) |
C21 | 0.067 (3) | 0.096 (3) | 0.101 (3) | −0.008 (2) | 0.018 (2) | −0.005 (2) |
C22 | 0.133 (5) | 0.098 (4) | 0.130 (5) | 0.008 (3) | 0.007 (4) | −0.003 (3) |
Geometric parameters (Å, º) top
O1—C1 | 1.228 (4) | C13—C15 | 1.519 (11) |
O2—C2 | 1.237 (5) | C13—C14 | 1.522 (10) |
N1—C1 | 1.346 (5) | C13—H131 | 0.9800 |
N1—C2 | 1.384 (5) | C14—H142 | 0.9600 |
N1—H11 | 0.8600 | C14—H141 | 0.9600 |
N2—C2 | 1.319 (5) | C14—H143 | 0.9600 |
N2—C21 | 1.448 (5) | C15—H152 | 0.9600 |
N2—H21 | 0.8600 | C15—H153 | 0.9600 |
C1—C11 | 1.494 (6) | C15—H151 | 0.9600 |
C11—C12 | 1.503 (6) | C21—C22 | 1.493 (7) |
C11—H112 | 0.9700 | C21—H211 | 0.9700 |
C11—H111 | 0.9700 | C21—H212 | 0.9700 |
C12—C13 | 1.524 (8) | C22—H223 | 0.9600 |
C12—H122 | 0.9700 | C22—H222 | 0.9600 |
C12—H121 | 0.9700 | C22—H221 | 0.9600 |
| | | |
C1—N1—C2 | 130.1 (3) | C15—C13—H131 | 108.7 |
C1—N1—H11 | 114.9 | C14—C13—H131 | 108.7 |
C2—N1—H11 | 114.9 | C12—C13—H131 | 108.7 |
C2—N2—C21 | 122.0 (4) | C13—C14—H142 | 109.5 |
C2—N2—H21 | 119.0 | C13—C14—H141 | 109.5 |
C21—N2—H21 | 119.0 | H142—C14—H141 | 109.5 |
O1—C1—N1 | 122.4 (4) | C13—C14—H143 | 109.5 |
O1—C1—C11 | 120.8 (4) | H142—C14—H143 | 109.5 |
N1—C1—C11 | 116.7 (3) | H141—C14—H143 | 109.5 |
O2—C2—N2 | 123.1 (4) | C13—C15—H152 | 109.5 |
O2—C2—N1 | 118.5 (3) | C13—C15—H153 | 109.5 |
N2—C2—N1 | 118.4 (4) | H152—C15—H153 | 109.5 |
C1—C11—C12 | 115.6 (4) | C13—C15—H151 | 109.5 |
C1—C11—H112 | 108.4 | H152—C15—H151 | 109.5 |
C12—C11—H112 | 108.4 | H153—C15—H151 | 109.5 |
C1—C11—H111 | 108.4 | N2—C21—C22 | 113.2 (4) |
C12—C11—H111 | 108.4 | N2—C21—H211 | 108.9 |
H112—C11—H111 | 107.4 | C22—C21—H211 | 108.9 |
C11—C12—C13 | 112.7 (4) | N2—C21—H212 | 108.9 |
C11—C12—H122 | 109.1 | C22—C21—H212 | 108.9 |
C13—C12—H122 | 109.1 | H211—C21—H212 | 107.8 |
C11—C12—H121 | 109.1 | C21—C22—H223 | 109.5 |
C13—C12—H121 | 109.1 | C21—C22—H222 | 109.5 |
H122—C12—H121 | 107.8 | H223—C22—H222 | 109.5 |
C15—C13—C14 | 109.7 (8) | C21—C22—H221 | 109.5 |
C15—C13—C12 | 112.0 (5) | H223—C22—H221 | 109.5 |
C14—C13—C12 | 108.9 (6) | H222—C22—H221 | 109.5 |
| | | |
C2—N1—C1—O1 | 0.6 (6) | O1—C1—C11—C12 | 55.9 (5) |
C2—N1—C1—C11 | −176.8 (3) | N1—C1—C11—C12 | −126.7 (4) |
C21—N2—C2—O2 | −0.2 (6) | C1—C11—C12—C13 | 66.3 (6) |
C21—N2—C2—N1 | 177.8 (3) | C11—C12—C13—C15 | 63.9 (8) |
C1—N1—C2—O2 | 179.9 (4) | C11—C12—C13—C14 | −174.6 (6) |
C1—N1—C2—N2 | 1.8 (6) | C2—N2—C21—C22 | −83.5 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O1i | 0.86 | 2.36 | 3.047 (4) | 137 |
N1—H11···O2ii | 0.86 | 1.98 | 2.840 (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
C9H18N2O2 | F(000) = 204 |
Mr = 186.25 | Dx = 1.094 Mg m−3 |
Triclinic, P1 | Melting point: 375 K |
a = 8.7270 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.6010 (13) Å | Cell parameters from 4364 reflections |
c = 5.1459 (3) Å | θ = 2.9–27.5° |
α = 91.317 (9)° | µ = 0.08 mm−1 |
β = 90.331 (11)° | T = 354 K |
γ = 89.001 (9)° | Plate, colourless |
V = 565.65 (7) Å3 | 0.80 × 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 tube | Rint = 0.026 |
Graphite monochromator | θmax = 27.5°, θmin = 2.3° |
Detector resolution: 10 pixels mm-1 | h = −11→11 |
Oscillation method scans | k = −16→16 |
6513 measured reflections | l = −6→6 |
2122 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.118 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.277 | H-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 parameters | Δρmax = 0.22 e Å−3 |
5 restraints | Δρmin = −0.22 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.4326 (3) | 0.5747 (3) | 0.2307 (7) | 0.0861 (10) | |
O2 | 0.0267 (3) | 0.4098 (3) | 0.2401 (7) | 0.0852 (10) | |
N1 | 0.1973 (4) | 0.5339 (3) | 0.3778 (7) | 0.0709 (10) | |
H11 | 0.1303 | 0.5531 | 0.4923 | 0.085* | |
N2 | 0.2522 (4) | 0.4164 (3) | 0.0306 (7) | 0.0712 (10) | |
H21 | 0.3383 | 0.4480 | 0.0169 | 0.085* | |
C1 | 0.3297 (4) | 0.5903 (3) | 0.3861 (9) | 0.0666 (11) | |
C2 | 0.1532 (4) | 0.4496 (3) | 0.2123 (9) | 0.0661 (11) | |
C11 | 0.3404 (5) | 0.6721 (4) | 0.6014 (10) | 0.0811 (13) | |
H112 | 0.4189 | 0.6492 | 0.7229 | 0.097* | |
H111 | 0.2437 | 0.6747 | 0.6937 | 0.097* | |
C12 | 0.3767 (7) | 0.7834 (4) | 0.5180 (13) | 0.112 (2) | |
H121 | 0.3964 | 0.8268 | 0.6723 | 0.134* | |
H122 | 0.4702 | 0.7803 | 0.4168 | 0.134* | |
C13 | 0.2538 (8) | 0.8369 (5) | 0.3608 (14) | 0.131 (2) | |
H131 | 0.2307 | 0.7922 | 0.2078 | 0.157* | |
C14 | 0.3074 (14) | 0.9447 (6) | 0.271 (2) | 0.219 (5) | |
H143 | 0.2279 | 0.9777 | 0.1698 | 0.262* | |
H142 | 0.3976 | 0.9350 | 0.1663 | 0.262* | |
H141 | 0.3305 | 0.9890 | 0.4195 | 0.262* | |
C15 | 0.1081 (9) | 0.8545 (7) | 0.518 (2) | 0.209 (5) | |
H152 | 0.0748 | 0.7879 | 0.5821 | 0.250* | |
H153 | 0.0296 | 0.8843 | 0.4088 | 0.250* | |
H151 | 0.1280 | 0.9024 | 0.6613 | 0.250* | |
C21 | 0.2180 (5) | 0.3283 (4) | −0.1443 (10) | 0.0819 (13) | |
H211 | 0.2783 | 0.3345 | −0.3009 | 0.098* | |
H212 | 0.1107 | 0.3328 | −0.1938 | 0.098* | |
C22 | 0.2503 (8) | 0.2210 (4) | −0.0295 (13) | 0.116 (2) | |
H223 | 0.2251 | 0.1663 | −0.1547 | 0.140* | |
H222 | 0.1893 | 0.2134 | 0.1234 | 0.140* | |
H221 | 0.3569 | 0.2150 | 0.0157 | 0.140* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0583 (17) | 0.102 (2) | 0.098 (2) | −0.0109 (15) | 0.0267 (16) | −0.0047 (19) |
O2 | 0.0544 (16) | 0.100 (2) | 0.102 (2) | −0.0142 (15) | 0.0237 (15) | −0.0063 (18) |
N1 | 0.0523 (18) | 0.079 (2) | 0.082 (2) | −0.0025 (16) | 0.0237 (17) | 0.001 (2) |
N2 | 0.0510 (18) | 0.082 (2) | 0.081 (2) | −0.0032 (16) | 0.0158 (16) | −0.0026 (19) |
C1 | 0.053 (2) | 0.071 (3) | 0.077 (3) | 0.0035 (18) | 0.0116 (19) | 0.016 (2) |
C2 | 0.049 (2) | 0.074 (3) | 0.076 (3) | 0.0056 (18) | 0.0106 (19) | 0.014 (2) |
C11 | 0.068 (3) | 0.083 (3) | 0.092 (3) | −0.003 (2) | 0.014 (2) | 0.005 (3) |
C12 | 0.098 (4) | 0.106 (4) | 0.132 (5) | −0.011 (3) | 0.028 (4) | −0.010 (4) |
C13 | 0.151 (7) | 0.113 (5) | 0.129 (6) | 0.014 (5) | −0.017 (5) | 0.025 (4) |
C14 | 0.342 (16) | 0.108 (6) | 0.208 (10) | −0.001 (8) | 0.033 (10) | 0.045 (6) |
C15 | 0.120 (7) | 0.166 (8) | 0.340 (16) | 0.035 (6) | −0.023 (9) | 0.032 (9) |
C21 | 0.062 (2) | 0.098 (3) | 0.086 (3) | −0.002 (2) | 0.012 (2) | 0.000 (3) |
C22 | 0.121 (5) | 0.092 (4) | 0.136 (5) | 0.003 (3) | 0.012 (4) | −0.001 (4) |
Geometric parameters (Å, º) top
O1—C1 | 1.217 (5) | C13—C15 | 1.520 (11) |
O2—C2 | 1.232 (5) | C13—C14 | 1.527 (11) |
N1—C1 | 1.367 (5) | C13—H131 | 0.9800 |
N1—C2 | 1.403 (6) | C14—H143 | 0.9600 |
N1—H11 | 0.8600 | C14—H142 | 0.9600 |
N2—C2 | 1.332 (5) | C14—H141 | 0.9600 |
N2—C21 | 1.447 (6) | C15—H152 | 0.9600 |
N2—H21 | 0.8600 | C15—H153 | 0.9600 |
C1—C11 | 1.499 (6) | C15—H151 | 0.9600 |
C11—C12 | 1.516 (7) | C21—C22 | 1.510 (8) |
C11—H112 | 0.9700 | C21—H211 | 0.9700 |
C11—H111 | 0.9700 | C21—H212 | 0.9700 |
C12—C13 | 1.500 (9) | C22—H223 | 0.9600 |
C12—H121 | 0.9700 | C22—H222 | 0.9600 |
C12—H122 | 0.9700 | C22—H221 | 0.9600 |
| | | |
C1—N1—C2 | 130.3 (3) | C12—C13—H131 | 108.9 |
C1—N1—H11 | 114.9 | C15—C13—H131 | 108.9 |
C2—N1—H11 | 114.9 | C14—C13—H131 | 108.9 |
C2—N2—C21 | 121.4 (4) | C13—C14—H143 | 109.5 |
C2—N2—H21 | 119.3 | C13—C14—H142 | 109.5 |
C21—N2—H21 | 119.3 | H143—C14—H142 | 109.5 |
O1—C1—N1 | 122.4 (4) | C13—C14—H141 | 109.5 |
O1—C1—C11 | 122.1 (4) | H143—C14—H141 | 109.5 |
N1—C1—C11 | 115.5 (4) | H142—C14—H141 | 109.5 |
O2—C2—N2 | 123.0 (4) | C13—C15—H152 | 109.5 |
O2—C2—N1 | 119.4 (4) | C13—C15—H153 | 109.5 |
N2—C2—N1 | 117.6 (3) | H152—C15—H153 | 109.5 |
C1—C11—C12 | 115.6 (4) | C13—C15—H151 | 109.5 |
C1—C11—H112 | 108.4 | H152—C15—H151 | 109.5 |
C12—C11—H112 | 108.4 | H153—C15—H151 | 109.5 |
C1—C11—H111 | 108.4 | N2—C21—C22 | 113.7 (4) |
C12—C11—H111 | 108.4 | N2—C21—H211 | 108.8 |
H112—C11—H111 | 107.4 | C22—C21—H211 | 108.8 |
C13—C12—C11 | 115.0 (5) | N2—C21—H212 | 108.8 |
C13—C12—H121 | 108.5 | C22—C21—H212 | 108.8 |
C11—C12—H121 | 108.5 | H211—C21—H212 | 107.7 |
C13—C12—H122 | 108.5 | C21—C22—H223 | 109.5 |
C11—C12—H122 | 108.5 | C21—C22—H222 | 109.5 |
H121—C12—H122 | 107.5 | H223—C22—H222 | 109.5 |
C12—C13—C15 | 111.4 (6) | C21—C22—H221 | 109.5 |
C12—C13—C14 | 110.5 (7) | H223—C22—H221 | 109.5 |
C15—C13—C14 | 108.2 (8) | H222—C22—H221 | 109.5 |
| | | |
C2—N1—C1—O1 | 2.7 (7) | O1—C1—C11—C12 | 54.2 (6) |
C2—N1—C1—C11 | −176.8 (4) | N1—C1—C11—C12 | −126.4 (4) |
C21—N2—C2—O2 | −1.5 (7) | C1—C11—C12—C13 | 66.9 (6) |
C21—N2—C2—N1 | 178.4 (4) | C11—C12—C13—C15 | 64.0 (8) |
C1—N1—C2—O2 | 179.8 (4) | C11—C12—C13—C14 | −175.8 (6) |
C1—N1—C2—N2 | −0.1 (6) | C2—N2—C21—C22 | −82.3 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O1i | 0.86 | 2.39 | 3.073 (4) | 137 |
N1—H11···O2ii | 0.86 | 1.99 | 2.850 (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
C9H18N2O2 | F(000) = 204 |
Mr = 186.25 | Dx = 1.108 Mg m−3 |
Triclinic, P1 | Melting point: 375 K |
a = 8.726 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.460 (3) Å | Cell parameters from 2070 reflections |
c = 5.1382 (12) Å | θ = 2.3–27.5° |
α = 91.423 (6)° | µ = 0.08 mm−1 |
β = 90.143 (10)° | T = 356 K |
γ = 89.297 (11)° | Plate, colourless |
V = 558.5 (2) Å3 | 0.80 × 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 tube | Rint = 0.035 |
Graphite monochromator | θmax = 27.5°, θmin = 2.3° |
Detector resolution: 10 pixels mm-1 | h = −10→11 |
Oscillation method scans | k = −15→15 |
6409 measured reflections | l = −6→6 |
1713 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.079 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.250 | H-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 parameters | Δρmax = 0.23 e Å−3 |
5 restraints | Δρmin = −0.24 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.4321 (3) | 0.5743 (2) | 0.2297 (5) | 0.0906 (8) | |
O2 | 0.0271 (3) | 0.4103 (2) | 0.2409 (5) | 0.0873 (8) | |
N1 | 0.1970 (3) | 0.5337 (2) | 0.3769 (5) | 0.0726 (8) | |
H11 | 0.1302 | 0.5527 | 0.4923 | 0.087* | |
N2 | 0.2523 (3) | 0.4164 (2) | 0.0323 (5) | 0.0759 (8) | |
H21 | 0.3390 | 0.4479 | 0.0207 | 0.091* | |
C1 | 0.3290 (4) | 0.5900 (3) | 0.3840 (6) | 0.0721 (9) | |
C2 | 0.1537 (4) | 0.4496 (3) | 0.2106 (6) | 0.0708 (8) | |
C11 | 0.3411 (4) | 0.6720 (3) | 0.5999 (7) | 0.0851 (10) | |
H112 | 0.4200 | 0.6487 | 0.7200 | 0.102* | |
H111 | 0.2448 | 0.6746 | 0.6940 | 0.102* | |
C12 | 0.3775 (5) | 0.7834 (3) | 0.5164 (10) | 0.1125 (14) | |
H122 | 0.4708 | 0.7803 | 0.4140 | 0.135* | |
H121 | 0.3975 | 0.8276 | 0.6705 | 0.135* | |
C13 | 0.2533 (7) | 0.8369 (4) | 0.3592 (11) | 0.138 (2) | |
H131 | 0.2304 | 0.7911 | 0.2066 | 0.165* | |
C14 | 0.3084 (12) | 0.9448 (5) | 0.2669 (17) | 0.217 (4) | |
H143 | 0.2299 | 0.9777 | 0.1636 | 0.260* | |
H142 | 0.3993 | 0.9343 | 0.1639 | 0.260* | |
H141 | 0.3309 | 0.9905 | 0.4149 | 0.260* | |
C15 | 0.1063 (8) | 0.8539 (6) | 0.5178 (19) | 0.205 (4) | |
H152 | 0.0722 | 0.7861 | 0.5793 | 0.246* | |
H153 | 0.0283 | 0.8849 | 0.4100 | 0.246* | |
H151 | 0.1262 | 0.9014 | 0.6637 | 0.246* | |
C21 | 0.2181 (4) | 0.3286 (3) | −0.1433 (7) | 0.0846 (10) | |
H211 | 0.2787 | 0.3350 | −0.3000 | 0.102* | |
H212 | 0.1109 | 0.3328 | −0.1926 | 0.102* | |
C22 | 0.2501 (7) | 0.2215 (3) | −0.0277 (10) | 0.1194 (15) | |
H223 | 0.2260 | 0.1656 | −0.1528 | 0.143* | |
H222 | 0.1882 | 0.2137 | 0.1248 | 0.143* | |
H221 | 0.3564 | 0.2163 | 0.0189 | 0.143* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0631 (14) | 0.1048 (18) | 0.1040 (17) | −0.0101 (12) | 0.0276 (13) | −0.0024 (14) |
O2 | 0.0605 (15) | 0.0961 (16) | 0.1052 (18) | −0.0090 (11) | 0.0257 (12) | −0.0039 (13) |
N1 | 0.0594 (15) | 0.0782 (17) | 0.0803 (16) | −0.0007 (12) | 0.0216 (12) | 0.0030 (13) |
N2 | 0.0572 (15) | 0.0836 (18) | 0.0868 (18) | −0.0003 (12) | 0.0171 (12) | 0.0004 (14) |
C1 | 0.0579 (18) | 0.0747 (19) | 0.085 (2) | 0.0035 (14) | 0.0125 (15) | 0.0196 (16) |
C2 | 0.0550 (17) | 0.0787 (19) | 0.079 (2) | 0.0058 (14) | 0.0136 (14) | 0.0123 (16) |
C11 | 0.078 (2) | 0.082 (2) | 0.095 (2) | −0.0011 (17) | 0.0099 (18) | 0.0000 (18) |
C12 | 0.100 (3) | 0.103 (3) | 0.135 (4) | −0.010 (2) | 0.025 (3) | −0.006 (3) |
C13 | 0.165 (6) | 0.107 (3) | 0.142 (4) | 0.012 (3) | −0.021 (4) | 0.016 (3) |
C14 | 0.333 (14) | 0.110 (4) | 0.210 (8) | −0.003 (6) | 0.015 (8) | 0.047 (5) |
C15 | 0.122 (6) | 0.162 (6) | 0.331 (12) | 0.038 (4) | −0.011 (7) | 0.022 (7) |
C21 | 0.065 (2) | 0.097 (2) | 0.091 (2) | 0.0017 (17) | 0.0127 (16) | −0.0025 (19) |
C22 | 0.134 (4) | 0.092 (3) | 0.132 (4) | 0.007 (3) | 0.007 (3) | 0.003 (3) |
Geometric parameters (Å, º) top
O1—C1 | 1.211 (4) | C13—C14 | 1.520 (9) |
O2—C2 | 1.225 (4) | C13—C15 | 1.532 (10) |
N1—C1 | 1.357 (4) | C13—H131 | 0.9800 |
N1—C2 | 1.390 (4) | C14—H143 | 0.9600 |
N1—H11 | 0.8600 | C14—H142 | 0.9600 |
N2—C2 | 1.314 (4) | C14—H141 | 0.9600 |
N2—C21 | 1.435 (4) | C15—H152 | 0.9600 |
N2—H21 | 0.8600 | C15—H153 | 0.9600 |
C1—C11 | 1.494 (5) | C15—H151 | 0.9600 |
C11—C12 | 1.501 (6) | C21—C22 | 1.497 (6) |
C11—H112 | 0.9700 | C21—H211 | 0.9700 |
C11—H111 | 0.9700 | C21—H212 | 0.9700 |
C12—C13 | 1.509 (8) | C22—H223 | 0.9600 |
C12—H122 | 0.9700 | C22—H222 | 0.9600 |
C12—H121 | 0.9700 | C22—H221 | 0.9600 |
| | | |
C1—N1—C2 | 129.6 (3) | C12—C13—H131 | 108.7 |
C1—N1—H11 | 115.2 | C14—C13—H131 | 108.7 |
C2—N1—H11 | 115.2 | C15—C13—H131 | 108.7 |
C2—N2—C21 | 121.3 (3) | C13—C14—H143 | 109.5 |
C2—N2—H21 | 119.3 | C13—C14—H142 | 109.5 |
C21—N2—H21 | 119.3 | H143—C14—H142 | 109.5 |
O1—C1—N1 | 122.9 (3) | C13—C14—H141 | 109.5 |
O1—C1—C11 | 121.7 (3) | H143—C14—H141 | 109.5 |
N1—C1—C11 | 115.5 (3) | H142—C14—H141 | 109.5 |
O2—C2—N2 | 124.1 (3) | C13—C15—H152 | 109.5 |
O2—C2—N1 | 118.2 (3) | C13—C15—H153 | 109.5 |
N2—C2—N1 | 117.7 (3) | H152—C15—H153 | 109.5 |
C1—C11—C12 | 115.1 (3) | C13—C15—H151 | 109.5 |
C1—C11—H112 | 108.5 | H152—C15—H151 | 109.5 |
C12—C11—H112 | 108.5 | H153—C15—H151 | 109.5 |
C1—C11—H111 | 108.5 | N2—C21—C22 | 112.7 (3) |
C12—C11—H111 | 108.5 | N2—C21—H211 | 109.0 |
H112—C11—H111 | 107.5 | C22—C21—H211 | 109.0 |
C11—C12—C13 | 114.7 (4) | N2—C21—H212 | 109.0 |
C11—C12—H122 | 108.6 | C22—C21—H212 | 109.0 |
C13—C12—H122 | 108.6 | H211—C21—H212 | 107.8 |
C11—C12—H121 | 108.6 | C21—C22—H223 | 109.5 |
C13—C12—H121 | 108.6 | C21—C22—H222 | 109.5 |
H122—C12—H121 | 107.6 | H223—C22—H222 | 109.5 |
C12—C13—C14 | 109.9 (6) | C21—C22—H221 | 109.5 |
C12—C13—C15 | 111.6 (5) | H223—C22—H221 | 109.5 |
C14—C13—C15 | 109.2 (6) | H222—C22—H221 | 109.5 |
| | | |
C2—N1—C1—O1 | 2.0 (5) | O1—C1—C11—C12 | 55.1 (5) |
C2—N1—C1—C11 | −176.7 (3) | N1—C1—C11—C12 | −126.2 (3) |
C21—N2—C2—O2 | −0.5 (5) | C1—C11—C12—C13 | 66.6 (5) |
C21—N2—C2—N1 | 178.6 (3) | C11—C12—C13—C14 | −175.2 (5) |
C1—N1—C2—O2 | 180.0 (3) | C11—C12—C13—C15 | 63.5 (6) |
C1—N1—C2—N2 | 0.8 (5) | C2—N2—C21—C22 | −83.1 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O1i | 0.86 | 2.39 | 3.073 (4) | 137 |
N1—H11···O2ii | 0.86 | 1.98 | 2.844 (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
C9H18N2O2 | F(000) = 204 |
Mr = 186.25 | Dx = 1.095 Mg m−3 |
Triclinic, P1 | Melting point: 375 K |
a = 8.7438 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.5269 (10) Å | Cell parameters from 2719 reflections |
c = 5.1573 (4) Å | θ = 4.0–27.4° |
α = 90.802 (6)° | µ = 0.08 mm−1 |
β = 90.388 (7)° | T = 358 K |
γ = 89.224 (3)° | Plate, colourless |
V = 564.77 (7) Å3 | 1.00 × 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 tube | Rint = 0.058 |
Graphite monochromator | θmax = 27.4°, θmin = 2.3° |
Detector resolution: 10 pixels mm-1 | h = −11→11 |
Oscillation method scans | k = −16→16 |
6499 measured reflections | l = −6→6 |
2397 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.103 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.298 | H-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 parameters | Δρmax = 0.36 e Å−3 |
5 restraints | Δρmin = −0.28 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.4322 (2) | 0.57411 (19) | 0.2289 (5) | 0.0866 (7) | |
O2 | 0.0270 (2) | 0.40995 (18) | 0.2426 (5) | 0.0839 (7) | |
N1 | 0.1973 (2) | 0.53358 (18) | 0.3763 (5) | 0.0685 (7) | |
H11 | 0.1306 | 0.5524 | 0.4905 | 0.082* | |
N2 | 0.2522 (3) | 0.4163 (2) | 0.0331 (5) | 0.0731 (7) | |
H21 | 0.3389 | 0.4474 | 0.0215 | 0.088* | |
C1 | 0.3293 (3) | 0.5898 (2) | 0.3831 (6) | 0.0685 (8) | |
C2 | 0.1542 (3) | 0.4499 (2) | 0.2113 (6) | 0.0677 (7) | |
C11 | 0.3410 (4) | 0.6723 (2) | 0.6002 (7) | 0.0828 (9) | |
H112 | 0.2446 | 0.6749 | 0.6923 | 0.099* | |
H111 | 0.4194 | 0.6489 | 0.7215 | 0.099* | |
C12 | 0.3775 (5) | 0.7827 (3) | 0.5155 (9) | 0.1082 (13) | |
H122 | 0.4706 | 0.7795 | 0.4142 | 0.130* | |
H121 | 0.3976 | 0.8264 | 0.6683 | 0.130* | |
C13 | 0.2537 (6) | 0.8362 (4) | 0.3571 (10) | 0.1355 (18) | |
H131 | 0.2316 | 0.7911 | 0.2050 | 0.163* | |
C14 | 0.3083 (11) | 0.9447 (5) | 0.2640 (17) | 0.222 (4) | |
H143 | 0.2295 | 0.9776 | 0.1607 | 0.267* | |
H142 | 0.3988 | 0.9349 | 0.1619 | 0.267* | |
H141 | 0.3306 | 0.9897 | 0.4113 | 0.267* | |
C15 | 0.1067 (7) | 0.8530 (6) | 0.5095 (17) | 0.204 (4) | |
H153 | 0.0307 | 0.8861 | 0.4009 | 0.244* | |
H151 | 0.1263 | 0.8981 | 0.6577 | 0.244* | |
H152 | 0.0704 | 0.7852 | 0.5662 | 0.244* | |
C21 | 0.2184 (4) | 0.3287 (3) | −0.1431 (7) | 0.0823 (9) | |
H211 | 0.2797 | 0.3354 | −0.2980 | 0.099* | |
H212 | 0.1117 | 0.3333 | −0.1946 | 0.099* | |
C22 | 0.2493 (5) | 0.2215 (3) | −0.0267 (10) | 0.1145 (14) | |
H223 | 0.2248 | 0.1665 | −0.1510 | 0.137* | |
H222 | 0.1876 | 0.2138 | 0.1249 | 0.137* | |
H221 | 0.3555 | 0.2157 | 0.0205 | 0.137* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0643 (12) | 0.0974 (15) | 0.0986 (16) | −0.0124 (10) | 0.0275 (11) | −0.0013 (12) |
O2 | 0.0601 (12) | 0.0913 (14) | 0.1009 (16) | −0.0127 (9) | 0.0233 (10) | −0.0026 (12) |
N1 | 0.0559 (12) | 0.0734 (14) | 0.0766 (15) | −0.0013 (10) | 0.0194 (10) | 0.0026 (12) |
N2 | 0.0567 (13) | 0.0770 (15) | 0.0859 (17) | −0.0015 (10) | 0.0183 (11) | −0.0011 (12) |
C1 | 0.0560 (14) | 0.0729 (16) | 0.0771 (18) | 0.0034 (11) | 0.0139 (12) | 0.0141 (13) |
C2 | 0.0534 (13) | 0.0737 (16) | 0.0764 (18) | 0.0043 (11) | 0.0155 (12) | 0.0136 (14) |
C11 | 0.0733 (18) | 0.0785 (19) | 0.097 (2) | 0.0010 (14) | 0.0112 (16) | 0.0006 (17) |
C12 | 0.104 (3) | 0.094 (3) | 0.127 (3) | −0.011 (2) | 0.027 (2) | −0.009 (2) |
C13 | 0.163 (5) | 0.101 (3) | 0.142 (4) | 0.008 (3) | −0.022 (4) | 0.014 (3) |
C14 | 0.351 (13) | 0.109 (4) | 0.208 (8) | −0.010 (5) | 0.035 (8) | 0.048 (5) |
C15 | 0.132 (5) | 0.145 (5) | 0.332 (11) | 0.029 (4) | −0.038 (7) | 0.009 (6) |
C21 | 0.0658 (17) | 0.091 (2) | 0.090 (2) | 0.0008 (14) | 0.0127 (15) | −0.0019 (17) |
C22 | 0.120 (3) | 0.089 (3) | 0.134 (3) | 0.006 (2) | 0.009 (3) | 0.004 (2) |
Geometric parameters (Å, º) top
O1—C1 | 1.217 (3) | C13—C15 | 1.522 (9) |
O2—C2 | 1.238 (3) | C13—C14 | 1.531 (8) |
N1—C1 | 1.361 (4) | C13—H131 | 0.9800 |
N1—C2 | 1.395 (4) | C14—H143 | 0.9600 |
N1—H11 | 0.8600 | C14—H142 | 0.9600 |
N2—C2 | 1.322 (4) | C14—H141 | 0.9600 |
N2—C21 | 1.447 (4) | C15—H153 | 0.9600 |
N2—H21 | 0.8600 | C15—H151 | 0.9600 |
C1—C11 | 1.516 (5) | C15—H152 | 0.9600 |
C11—C12 | 1.495 (5) | C21—C22 | 1.498 (5) |
C11—H112 | 0.9700 | C21—H211 | 0.9700 |
C11—H111 | 0.9700 | C21—H212 | 0.9700 |
C12—C13 | 1.508 (7) | C22—H223 | 0.9600 |
C12—H122 | 0.9700 | C22—H222 | 0.9600 |
C12—H121 | 0.9700 | C22—H221 | 0.9600 |
| | | |
C1—N1—C2 | 129.5 (2) | C12—C13—H131 | 108.6 |
C1—N1—H11 | 115.2 | C15—C13—H131 | 108.6 |
C2—N1—H11 | 115.2 | C14—C13—H131 | 108.6 |
C2—N2—C21 | 122.1 (2) | C13—C14—H143 | 109.5 |
C2—N2—H21 | 118.9 | C13—C14—H142 | 109.5 |
C21—N2—H21 | 118.9 | H143—C14—H142 | 109.5 |
O1—C1—N1 | 122.6 (3) | C13—C14—H141 | 109.5 |
O1—C1—C11 | 122.1 (3) | H143—C14—H141 | 109.5 |
N1—C1—C11 | 115.3 (2) | H142—C14—H141 | 109.5 |
O2—C2—N2 | 123.5 (3) | C13—C15—H153 | 109.5 |
O2—C2—N1 | 118.2 (3) | C13—C15—H151 | 109.5 |
N2—C2—N1 | 118.3 (2) | H153—C15—H151 | 109.5 |
C12—C11—C1 | 115.1 (3) | C13—C15—H152 | 109.5 |
C12—C11—H112 | 108.5 | H153—C15—H152 | 109.5 |
C1—C11—H112 | 108.5 | H151—C15—H152 | 109.5 |
C12—C11—H111 | 108.5 | N2—C21—C22 | 112.9 (3) |
C1—C11—H111 | 108.5 | N2—C21—H211 | 109.0 |
H112—C11—H111 | 107.5 | C22—C21—H211 | 109.0 |
C11—C12—C13 | 114.6 (3) | N2—C21—H212 | 109.0 |
C11—C12—H122 | 108.6 | C22—C21—H212 | 109.0 |
C13—C12—H122 | 108.6 | H211—C21—H212 | 107.8 |
C11—C12—H121 | 108.6 | C21—C22—H223 | 109.5 |
C13—C12—H121 | 108.6 | C21—C22—H222 | 109.5 |
H122—C12—H121 | 107.6 | H223—C22—H222 | 109.5 |
C12—C13—C15 | 112.2 (5) | C21—C22—H221 | 109.5 |
C12—C13—C14 | 110.0 (5) | H223—C22—H221 | 109.5 |
C15—C13—C14 | 108.7 (6) | H222—C22—H221 | 109.5 |
| | | |
C2—N1—C1—O1 | 2.1 (5) | O1—C1—C11—C12 | 54.6 (4) |
C2—N1—C1—C11 | −176.8 (3) | N1—C1—C11—C12 | −126.5 (3) |
C21—N2—C2—O2 | 0.1 (4) | C1—C11—C12—C13 | 66.9 (5) |
C21—N2—C2—N1 | 178.8 (2) | C11—C12—C13—C15 | 63.1 (6) |
C1—N1—C2—O2 | 179.5 (3) | C11—C12—C13—C14 | −175.7 (5) |
C1—N1—C2—N2 | 0.8 (4) | C2—N2—C21—C22 | −82.7 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O1i | 0.86 | 2.40 | 3.085 (3) | 137 |
N1—H11···O2ii | 0.86 | 2.00 | 2.861 (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
C9H18N2O2 | F(000) = 204 |
Mr = 186.25 | Dx = 1.091 Mg m−3 |
Triclinic, P1 | Melting point: 375 K |
a = 8.7564 (14) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.5792 (14) Å | Cell parameters from 2770 reflections |
c = 5.1472 (6) Å | θ = 2.8–27.3° |
α = 90.683 (10)° | µ = 0.08 mm−1 |
β = 90.707 (6)° | T = 360 K |
γ = 89.216 (6)° | Plate, colourless |
V = 566.82 (13) Å3 | 1.00 × 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 tube | Rint = 0.055 |
Graphite monochromator | θmax = 27.4°, θmin = 2.3° |
Detector resolution: 10 pixels mm-1 | h = −11→11 |
Oscillation method scans | k = −16→16 |
6442 measured reflections | l = −6→6 |
2389 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.100 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.316 | H-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 parameters | Δρmax = 0.31 e Å−3 |
5 restraints | Δρmin = −0.29 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.4323 (3) | 0.5741 (2) | 0.2286 (6) | 0.0901 (8) | |
O2 | 0.0268 (3) | 0.4099 (2) | 0.2428 (5) | 0.0870 (8) | |
N1 | 0.1970 (3) | 0.5334 (2) | 0.3761 (6) | 0.0710 (8) | |
H11 | 0.1304 | 0.5521 | 0.4898 | 0.085* | |
N2 | 0.2524 (3) | 0.4167 (2) | 0.0336 (6) | 0.0747 (8) | |
H21 | 0.3385 | 0.4483 | 0.0205 | 0.090* | |
C1 | 0.3288 (4) | 0.5898 (3) | 0.3835 (7) | 0.0698 (9) | |
C2 | 0.1541 (4) | 0.4501 (3) | 0.2124 (7) | 0.0712 (9) | |
C11 | 0.3405 (5) | 0.6718 (3) | 0.5965 (8) | 0.0845 (10) | |
H112 | 0.4188 | 0.6486 | 0.7190 | 0.101* | |
H111 | 0.2443 | 0.6743 | 0.6881 | 0.101* | |
C12 | 0.3769 (6) | 0.7824 (4) | 0.5126 (11) | 0.1170 (16) | |
H121 | 0.4692 | 0.7795 | 0.4104 | 0.140* | |
H122 | 0.3979 | 0.8254 | 0.6662 | 0.140* | |
C13 | 0.2526 (7) | 0.8365 (4) | 0.3553 (13) | 0.140 (2) | |
H131 | 0.2293 | 0.7922 | 0.2024 | 0.168* | |
C14 | 0.3085 (14) | 0.9442 (5) | 0.264 (2) | 0.233 (5) | |
H143 | 0.2299 | 0.9782 | 0.1622 | 0.279* | |
H142 | 0.3982 | 0.9340 | 0.1610 | 0.279* | |
H141 | 0.3327 | 0.9881 | 0.4127 | 0.279* | |
C15 | 0.1069 (8) | 0.8536 (7) | 0.509 (2) | 0.218 (5) | |
H153 | 0.0310 | 0.8877 | 0.4020 | 0.261* | |
H151 | 0.1281 | 0.8977 | 0.6588 | 0.261* | |
H152 | 0.0699 | 0.7862 | 0.5650 | 0.261* | |
C21 | 0.2183 (4) | 0.3289 (3) | −0.1393 (8) | 0.0845 (10) | |
H211 | 0.2780 | 0.3356 | −0.2956 | 0.101* | |
H212 | 0.1113 | 0.3331 | −0.1895 | 0.101* | |
C22 | 0.2504 (7) | 0.2222 (4) | −0.0241 (11) | 0.1191 (16) | |
H223 | 0.2252 | 0.1676 | −0.1486 | 0.143* | |
H222 | 0.1899 | 0.2141 | 0.1285 | 0.143* | |
H221 | 0.3567 | 0.2165 | 0.0220 | 0.143* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0673 (14) | 0.1010 (18) | 0.1031 (18) | −0.0140 (12) | 0.0296 (13) | −0.0023 (14) |
O2 | 0.0617 (14) | 0.0968 (17) | 0.1034 (19) | −0.0135 (11) | 0.0254 (12) | −0.0052 (14) |
N1 | 0.0581 (14) | 0.0739 (16) | 0.0816 (17) | −0.0041 (11) | 0.0225 (12) | 0.0009 (13) |
N2 | 0.0576 (14) | 0.0799 (17) | 0.0870 (19) | −0.0035 (12) | 0.0198 (13) | −0.0010 (14) |
C1 | 0.0573 (16) | 0.0748 (19) | 0.078 (2) | −0.0007 (13) | 0.0135 (14) | 0.0148 (15) |
C2 | 0.0556 (16) | 0.0758 (19) | 0.083 (2) | 0.0048 (13) | 0.0173 (14) | 0.0131 (16) |
C11 | 0.079 (2) | 0.080 (2) | 0.095 (3) | 0.0000 (17) | 0.0101 (19) | 0.0035 (19) |
C12 | 0.110 (3) | 0.106 (3) | 0.135 (4) | −0.014 (3) | 0.026 (3) | −0.008 (3) |
C13 | 0.162 (6) | 0.111 (4) | 0.148 (5) | 0.011 (4) | −0.020 (4) | 0.018 (3) |
C14 | 0.371 (16) | 0.107 (5) | 0.222 (9) | −0.005 (6) | 0.024 (10) | 0.049 (5) |
C15 | 0.125 (6) | 0.169 (7) | 0.357 (14) | 0.028 (5) | −0.041 (8) | 0.009 (8) |
C21 | 0.068 (2) | 0.093 (2) | 0.093 (2) | −0.0001 (17) | 0.0115 (18) | −0.004 (2) |
C22 | 0.129 (4) | 0.089 (3) | 0.139 (4) | 0.004 (3) | 0.012 (3) | −0.004 (3) |
Geometric parameters (Å, º) top
O1—C1 | 1.227 (4) | C13—C15 | 1.522 (11) |
O2—C2 | 1.243 (4) | C13—C14 | 1.527 (10) |
N1—C1 | 1.363 (4) | C13—H131 | 0.9800 |
N1—C2 | 1.390 (5) | C14—H143 | 0.9600 |
N1—H11 | 0.8600 | C14—H142 | 0.9600 |
N2—C2 | 1.328 (4) | C14—H141 | 0.9600 |
N2—C21 | 1.443 (5) | C15—H153 | 0.9600 |
N2—H21 | 0.8600 | C15—H151 | 0.9600 |
C1—C11 | 1.499 (5) | C15—H152 | 0.9600 |
C11—C12 | 1.502 (6) | C21—C22 | 1.495 (6) |
C11—H112 | 0.9700 | C21—H211 | 0.9700 |
C11—H111 | 0.9700 | C21—H212 | 0.9700 |
C12—C13 | 1.508 (8) | C22—H223 | 0.9600 |
C12—H121 | 0.9700 | C22—H222 | 0.9600 |
C12—H122 | 0.9700 | C22—H221 | 0.9600 |
| | | |
C1—N1—C2 | 129.7 (3) | C12—C13—H131 | 108.7 |
C1—N1—H11 | 115.2 | C15—C13—H131 | 108.7 |
C2—N1—H11 | 115.2 | C14—C13—H131 | 108.7 |
C2—N2—C21 | 121.6 (3) | C13—C14—H143 | 109.5 |
C2—N2—H21 | 119.2 | C13—C14—H142 | 109.5 |
C21—N2—H21 | 119.2 | H143—C14—H142 | 109.5 |
O1—C1—N1 | 122.5 (3) | C13—C14—H141 | 109.5 |
O1—C1—C11 | 121.9 (3) | H143—C14—H141 | 109.5 |
N1—C1—C11 | 115.6 (3) | H142—C14—H141 | 109.5 |
O2—C2—N2 | 123.4 (3) | C13—C15—H153 | 109.5 |
O2—C2—N1 | 118.4 (3) | C13—C15—H151 | 109.5 |
N2—C2—N1 | 118.2 (3) | H153—C15—H151 | 109.5 |
C1—C11—C12 | 115.9 (3) | C13—C15—H152 | 109.5 |
C1—C11—H112 | 108.3 | H153—C15—H152 | 109.5 |
C12—C11—H112 | 108.3 | H151—C15—H152 | 109.5 |
C1—C11—H111 | 108.3 | N2—C21—C22 | 113.8 (4) |
C12—C11—H111 | 108.3 | N2—C21—H211 | 108.8 |
H112—C11—H111 | 107.4 | C22—C21—H211 | 108.8 |
C11—C12—C13 | 114.7 (4) | N2—C21—H212 | 108.8 |
C11—C12—H121 | 108.6 | C22—C21—H212 | 108.8 |
C13—C12—H121 | 108.6 | H211—C21—H212 | 107.7 |
C11—C12—H122 | 108.6 | C21—C22—H223 | 109.5 |
C13—C12—H122 | 108.6 | C21—C22—H222 | 109.5 |
H121—C12—H122 | 107.6 | H223—C22—H222 | 109.5 |
C12—C13—C15 | 112.3 (6) | C21—C22—H221 | 109.5 |
C12—C13—C14 | 109.5 (6) | H223—C22—H221 | 109.5 |
C15—C13—C14 | 108.9 (7) | H222—C22—H221 | 109.5 |
| | | |
C2—N1—C1—O1 | 2.1 (6) | O1—C1—C11—C12 | 54.4 (5) |
C2—N1—C1—C11 | −177.0 (3) | N1—C1—C11—C12 | −126.5 (4) |
C21—N2—C2—O2 | −0.7 (5) | C1—C11—C12—C13 | 67.5 (6) |
C21—N2—C2—N1 | 178.3 (3) | C11—C12—C13—C15 | 63.5 (7) |
C1—N1—C2—O2 | 179.6 (3) | C11—C12—C13—C14 | −175.5 (6) |
C1—N1—C2—N2 | 0.5 (5) | C2—N2—C21—C22 | −82.8 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O1i | 0.86 | 2.41 | 3.092 (4) | 137 |
N1—H11···O2ii | 0.86 | 2.01 | 2.867 (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
C9H18N2O2 | F(000) = 204 |
Mr = 186.25 | Dx = 1.104 Mg m−3 |
Triclinic, P1 | Melting point: 375 K |
a = 8.670 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.5515 (9) Å | Cell parameters from 2412 reflections |
c = 5.1490 (5) Å | θ = 2.8–27.4° |
α = 90.036 (7)° | µ = 0.08 mm−1 |
β = 91.078 (4)° | T = 362 K |
γ = 88.834 (4)° | Plate, colourless |
V = 560.11 (9) Å3 | 1.00 × 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 tube | Rint = 0.032 |
Graphite monochromator | θmax = 27.5°, θmin = 2.4° |
Detector resolution: 10 pixels mm-1 | h = −11→11 |
Oscillation method scans | k = −16→16 |
6484 measured reflections | l = −6→6 |
2361 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.094 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.332 | H-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 parameters | Δρmax = 0.37 e Å−3 |
5 restraints | Δρmin = −0.34 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.4317 (3) | 0.5740 (2) | 0.2258 (5) | 0.0949 (9) | |
O2 | 0.0275 (3) | 0.4100 (2) | 0.2453 (5) | 0.0914 (9) | |
N1 | 0.1969 (3) | 0.5334 (2) | 0.3743 (6) | 0.0748 (8) | |
H11 | 0.1295 | 0.5524 | 0.4868 | 0.090* | |
N2 | 0.2531 (3) | 0.4165 (2) | 0.0370 (6) | 0.0797 (9) | |
H21 | 0.3405 | 0.4471 | 0.0254 | 0.096* | |
C1 | 0.3285 (3) | 0.5898 (3) | 0.3805 (7) | 0.0746 (9) | |
C2 | 0.1545 (4) | 0.4502 (3) | 0.2152 (7) | 0.0743 (9) | |
C11 | 0.3404 (5) | 0.6710 (3) | 0.5935 (8) | 0.0920 (11) | |
H112 | 0.4198 | 0.6471 | 0.7166 | 0.110* | |
H111 | 0.2434 | 0.6736 | 0.6845 | 0.110* | |
C12 | 0.3768 (6) | 0.7819 (4) | 0.5084 (11) | 0.1242 (17) | |
H121 | 0.3985 | 0.8246 | 0.6615 | 0.149* | |
H122 | 0.4697 | 0.7789 | 0.4064 | 0.149* | |
C13 | 0.2523 (8) | 0.8363 (4) | 0.3527 (13) | 0.152 (2) | |
H131 | 0.2281 | 0.7923 | 0.2006 | 0.183* | |
C14 | 0.3107 (14) | 0.9435 (6) | 0.260 (2) | 0.251 (6) | |
H143 | 0.2318 | 0.9787 | 0.1563 | 0.301* | |
H142 | 0.4010 | 0.9322 | 0.1577 | 0.301* | |
H141 | 0.3358 | 0.9870 | 0.4075 | 0.301* | |
C15 | 0.1059 (8) | 0.8539 (7) | 0.507 (2) | 0.227 (5) | |
H153 | 0.0287 | 0.8887 | 0.3991 | 0.273* | |
H151 | 0.1280 | 0.8976 | 0.6555 | 0.273* | |
H152 | 0.0686 | 0.7864 | 0.5635 | 0.273* | |
C21 | 0.2176 (4) | 0.3298 (3) | −0.1379 (8) | 0.0913 (11) | |
H211 | 0.2779 | 0.3365 | −0.2936 | 0.110* | |
H212 | 0.1094 | 0.3346 | −0.1887 | 0.110* | |
C22 | 0.2508 (6) | 0.2234 (4) | −0.0178 (11) | 0.1232 (16) | |
H223 | 0.2254 | 0.1684 | −0.1399 | 0.148* | |
H222 | 0.1900 | 0.2159 | 0.1348 | 0.148* | |
H221 | 0.3583 | 0.2176 | 0.0291 | 0.148* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0658 (13) | 0.1088 (19) | 0.1116 (19) | −0.0130 (12) | 0.0314 (13) | −0.0022 (14) |
O2 | 0.0629 (13) | 0.0996 (17) | 0.1131 (19) | −0.0112 (11) | 0.0291 (12) | −0.0031 (14) |
N1 | 0.0582 (14) | 0.0805 (17) | 0.0866 (17) | −0.0030 (11) | 0.0229 (12) | 0.0022 (13) |
N2 | 0.0590 (14) | 0.0865 (18) | 0.0943 (19) | 0.0009 (12) | 0.0211 (13) | 0.0013 (15) |
C1 | 0.0584 (15) | 0.0772 (19) | 0.089 (2) | 0.0043 (13) | 0.0159 (14) | 0.0167 (16) |
C2 | 0.0570 (15) | 0.0818 (19) | 0.085 (2) | 0.0020 (13) | 0.0165 (14) | 0.0119 (16) |
C11 | 0.080 (2) | 0.089 (2) | 0.107 (3) | −0.0002 (18) | 0.0159 (19) | 0.000 (2) |
C12 | 0.117 (4) | 0.109 (3) | 0.148 (4) | −0.010 (3) | 0.034 (3) | −0.007 (3) |
C13 | 0.177 (6) | 0.112 (4) | 0.166 (6) | 0.012 (4) | −0.020 (5) | 0.023 (4) |
C14 | 0.389 (17) | 0.115 (5) | 0.250 (11) | −0.002 (7) | 0.047 (11) | 0.062 (6) |
C15 | 0.129 (6) | 0.163 (7) | 0.387 (15) | 0.039 (5) | −0.026 (8) | 0.019 (8) |
C21 | 0.072 (2) | 0.100 (3) | 0.102 (3) | 0.0020 (18) | 0.0164 (18) | −0.004 (2) |
C22 | 0.129 (4) | 0.096 (3) | 0.144 (4) | 0.005 (3) | 0.010 (3) | 0.003 (3) |
Geometric parameters (Å, º) top
O1—C1 | 1.222 (4) | C13—C15 | 1.522 (11) |
O2—C2 | 1.232 (4) | C13—C14 | 1.527 (11) |
N1—C1 | 1.355 (4) | C13—H131 | 0.9800 |
N1—C2 | 1.378 (5) | C14—H143 | 0.9600 |
N1—H11 | 0.8600 | C14—H142 | 0.9600 |
N2—C2 | 1.329 (4) | C14—H141 | 0.9600 |
N2—C21 | 1.447 (5) | C15—H153 | 0.9600 |
N2—H21 | 0.8600 | C15—H151 | 0.9600 |
C1—C11 | 1.500 (5) | C15—H152 | 0.9600 |
C11—C12 | 1.501 (6) | C21—C22 | 1.492 (6) |
C11—H112 | 0.9700 | C21—H211 | 0.9700 |
C11—H111 | 0.9700 | C21—H212 | 0.9700 |
C12—C13 | 1.487 (8) | C22—H223 | 0.9600 |
C12—H121 | 0.9700 | C22—H222 | 0.9600 |
C12—H122 | 0.9700 | C22—H221 | 0.9600 |
| | | |
C1—N1—C2 | 129.8 (3) | C12—C13—H131 | 108.7 |
C1—N1—H11 | 115.1 | C15—C13—H131 | 108.7 |
C2—N1—H11 | 115.1 | C14—C13—H131 | 108.7 |
C2—N2—C21 | 121.9 (3) | C13—C14—H143 | 109.5 |
C2—N2—H21 | 119.0 | C13—C14—H142 | 109.5 |
C21—N2—H21 | 119.0 | H143—C14—H142 | 109.5 |
O1—C1—N1 | 122.1 (4) | C13—C14—H141 | 109.5 |
O1—C1—C11 | 122.4 (3) | H143—C14—H141 | 109.5 |
N1—C1—C11 | 115.5 (3) | H142—C14—H141 | 109.5 |
O2—C2—N2 | 122.9 (4) | C13—C15—H153 | 109.5 |
O2—C2—N1 | 118.7 (3) | C13—C15—H151 | 109.5 |
N2—C2—N1 | 118.4 (3) | H153—C15—H151 | 109.5 |
C1—C11—C12 | 115.6 (4) | C13—C15—H152 | 109.5 |
C1—C11—H112 | 108.4 | H153—C15—H152 | 109.5 |
C12—C11—H112 | 108.4 | H151—C15—H152 | 109.5 |
C1—C11—H111 | 108.4 | N2—C21—C22 | 112.2 (4) |
C12—C11—H111 | 108.4 | N2—C21—H211 | 109.2 |
H112—C11—H111 | 107.4 | C22—C21—H211 | 109.2 |
C13—C12—C11 | 114.7 (4) | N2—C21—H212 | 109.2 |
C13—C12—H121 | 108.6 | C22—C21—H212 | 109.2 |
C11—C12—H121 | 108.6 | H211—C21—H212 | 107.9 |
C13—C12—H122 | 108.6 | C21—C22—H223 | 109.5 |
C11—C12—H122 | 108.6 | C21—C22—H222 | 109.5 |
H121—C12—H122 | 107.6 | H223—C22—H222 | 109.5 |
C12—C13—C15 | 112.3 (6) | C21—C22—H221 | 109.5 |
C12—C13—C14 | 108.8 (7) | H223—C22—H221 | 109.5 |
C15—C13—C14 | 109.5 (7) | H222—C22—H221 | 109.5 |
| | | |
C2—N1—C1—O1 | 2.6 (5) | O1—C1—C11—C12 | 54.3 (5) |
C2—N1—C1—C11 | −175.9 (3) | N1—C1—C11—C12 | −127.2 (4) |
C21—N2—C2—O2 | 0.6 (5) | C1—C11—C12—C13 | 67.6 (6) |
C21—N2—C2—N1 | −179.9 (3) | C11—C12—C13—C15 | 63.7 (8) |
C1—N1—C2—O2 | 179.7 (3) | C11—C12—C13—C14 | −175.0 (6) |
C1—N1—C2—N2 | 0.2 (5) | C2—N2—C21—C22 | −83.2 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O1i | 0.86 | 2.39 | 3.077 (4) | 137 |
N1—H11···O2ii | 0.86 | 2.01 | 2.866 (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
C9H18N2O2 | F(000) = 204 |
Mr = 186.25 | Dx = 1.085 Mg m−3 |
Triclinic, P1 | Melting point: 375 K |
a = 8.7109 (12) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.6454 (10) Å | Cell parameters from 2832 reflections |
c = 5.1787 (6) Å | θ = 2.8–27.5° |
α = 90.134 (7)° | µ = 0.08 mm−1 |
β = 90.557 (4)° | T = 364 K |
γ = 88.953 (4)° | Triclinic, p -1 |
V = 570.32 (11) Å3 | 1.00 × 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 tube | Rint = 0.028 |
Graphite monochromator | θmax = 27.5°, θmin = 2.3° |
Detector resolution: 10 pixels mm-1 | h = −11→11 |
Oscillation method scans | k = −16→16 |
7726 measured reflections | l = −6→6 |
2503 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.091 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.301 | H-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 parameters | Δρmax = 0.33 e Å−3 |
5 restraints | Δρmin = −0.34 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.4319 (3) | 0.5736 (2) | 0.2249 (5) | 0.0986 (9) | |
O2 | 0.0272 (2) | 0.4103 (2) | 0.2467 (5) | 0.0946 (8) | |
N1 | 0.1969 (3) | 0.5332 (2) | 0.3748 (5) | 0.0782 (8) | |
H11 | 0.1299 | 0.5519 | 0.4879 | 0.094* | |
N2 | 0.2527 (3) | 0.4164 (2) | 0.0378 (5) | 0.0816 (8) | |
H21 | 0.3394 | 0.4473 | 0.0241 | 0.098* | |
C1 | 0.3282 (3) | 0.5898 (3) | 0.3795 (7) | 0.0773 (9) | |
C2 | 0.1543 (3) | 0.4501 (3) | 0.2157 (7) | 0.0770 (9) | |
C11 | 0.3393 (4) | 0.6712 (3) | 0.5878 (8) | 0.0947 (11) | |
H112 | 0.4174 | 0.6478 | 0.7108 | 0.114* | |
H111 | 0.2423 | 0.6741 | 0.6781 | 0.114* | |
C12 | 0.3765 (6) | 0.7815 (4) | 0.5040 (12) | 0.1366 (19) | |
H121 | 0.3983 | 0.8236 | 0.6563 | 0.164* | |
H122 | 0.4690 | 0.7784 | 0.4012 | 0.164* | |
C13 | 0.2526 (8) | 0.8360 (5) | 0.3510 (13) | 0.164 (2) | |
H131 | 0.2278 | 0.7921 | 0.2005 | 0.197* | |
C14 | 0.3093 (14) | 0.9432 (6) | 0.256 (2) | 0.268 (6) | |
H143 | 0.2300 | 0.9774 | 0.1545 | 0.321* | |
H142 | 0.3988 | 0.9324 | 0.1516 | 0.321* | |
H141 | 0.3345 | 0.9869 | 0.4013 | 0.321* | |
C15 | 0.1066 (9) | 0.8549 (7) | 0.506 (2) | 0.254 (5) | |
H153 | 0.0311 | 0.8906 | 0.3998 | 0.305* | |
H151 | 0.1294 | 0.8977 | 0.6542 | 0.305* | |
H152 | 0.0674 | 0.7882 | 0.5612 | 0.305* | |
C21 | 0.2184 (4) | 0.3296 (3) | −0.1327 (8) | 0.0941 (11) | |
H211 | 0.2785 | 0.3363 | −0.2883 | 0.113* | |
H212 | 0.1108 | 0.3342 | −0.1821 | 0.113* | |
C22 | 0.2509 (6) | 0.2236 (4) | −0.0161 (11) | 0.1308 (17) | |
H223 | 0.2256 | 0.1694 | −0.1385 | 0.157* | |
H222 | 0.1902 | 0.2157 | 0.1362 | 0.157* | |
H221 | 0.3579 | 0.2177 | 0.0291 | 0.157* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0688 (13) | 0.1134 (18) | 0.1148 (19) | −0.0135 (12) | 0.0318 (13) | −0.0016 (14) |
O2 | 0.0659 (13) | 0.1035 (17) | 0.1153 (19) | −0.0122 (11) | 0.0291 (12) | −0.0042 (14) |
N1 | 0.0613 (14) | 0.0823 (16) | 0.0916 (18) | −0.0019 (11) | 0.0244 (12) | 0.0028 (14) |
N2 | 0.0597 (14) | 0.0895 (18) | 0.0961 (19) | −0.0029 (12) | 0.0200 (13) | 0.0002 (15) |
C1 | 0.0602 (16) | 0.0814 (19) | 0.090 (2) | 0.0025 (13) | 0.0160 (14) | 0.0168 (16) |
C2 | 0.0569 (15) | 0.086 (2) | 0.088 (2) | 0.0057 (14) | 0.0179 (14) | 0.0129 (17) |
C11 | 0.083 (2) | 0.087 (2) | 0.115 (3) | −0.0018 (17) | 0.0169 (19) | 0.002 (2) |
C12 | 0.124 (4) | 0.118 (4) | 0.169 (5) | −0.011 (3) | 0.040 (3) | −0.007 (3) |
C13 | 0.175 (6) | 0.133 (4) | 0.183 (6) | 0.019 (4) | −0.013 (5) | 0.039 (4) |
C14 | 0.416 (18) | 0.120 (5) | 0.268 (11) | −0.021 (7) | 0.024 (11) | 0.065 (6) |
C15 | 0.138 (6) | 0.191 (8) | 0.432 (16) | 0.044 (5) | −0.026 (8) | 0.027 (9) |
C21 | 0.073 (2) | 0.103 (3) | 0.106 (3) | 0.0018 (17) | 0.0162 (18) | −0.001 (2) |
C22 | 0.135 (4) | 0.100 (3) | 0.157 (4) | 0.007 (3) | 0.013 (3) | 0.001 (3) |
Geometric parameters (Å, º) top
O1—C1 | 1.226 (4) | C13—C15 | 1.525 (11) |
O2—C2 | 1.236 (4) | C13—C14 | 1.536 (10) |
N1—C1 | 1.360 (4) | C13—H131 | 0.9800 |
N1—C2 | 1.388 (5) | C14—H143 | 0.9600 |
N1—H11 | 0.8600 | C14—H142 | 0.9600 |
N2—C2 | 1.329 (4) | C14—H141 | 0.9600 |
N2—C21 | 1.440 (5) | C15—H153 | 0.9600 |
N2—H21 | 0.8600 | C15—H151 | 0.9600 |
C1—C11 | 1.494 (5) | C15—H152 | 0.9600 |
C11—C12 | 1.503 (6) | C21—C22 | 1.493 (6) |
C11—H112 | 0.9700 | C21—H211 | 0.9700 |
C11—H111 | 0.9700 | C21—H212 | 0.9700 |
C12—C13 | 1.492 (8) | C22—H223 | 0.9600 |
C12—H121 | 0.9700 | C22—H222 | 0.9600 |
C12—H122 | 0.9700 | C22—H221 | 0.9600 |
| | | |
C1—N1—C2 | 129.9 (3) | C12—C13—H131 | 108.6 |
C1—N1—H11 | 115.0 | C15—C13—H131 | 108.6 |
C2—N1—H11 | 115.0 | C14—C13—H131 | 108.6 |
C2—N2—C21 | 121.9 (3) | C13—C14—H143 | 109.5 |
C2—N2—H21 | 119.1 | C13—C14—H142 | 109.5 |
C21—N2—H21 | 119.1 | H143—C14—H142 | 109.5 |
O1—C1—N1 | 122.0 (3) | C13—C14—H141 | 109.5 |
O1—C1—C11 | 122.3 (3) | H143—C14—H141 | 109.5 |
N1—C1—C11 | 115.7 (3) | H142—C14—H141 | 109.5 |
O2—C2—N2 | 123.0 (3) | C13—C15—H153 | 109.5 |
O2—C2—N1 | 118.7 (3) | C13—C15—H151 | 109.5 |
N2—C2—N1 | 118.3 (3) | H153—C15—H151 | 109.5 |
C1—C11—C12 | 116.5 (4) | C13—C15—H152 | 109.5 |
C1—C11—H112 | 108.2 | H153—C15—H152 | 109.5 |
C12—C11—H112 | 108.2 | H151—C15—H152 | 109.5 |
C1—C11—H111 | 108.2 | N2—C21—C22 | 113.5 (4) |
C12—C11—H111 | 108.2 | N2—C21—H211 | 108.9 |
H112—C11—H111 | 107.3 | C22—C21—H211 | 108.9 |
C13—C12—C11 | 114.6 (4) | N2—C21—H212 | 108.9 |
C13—C12—H121 | 108.6 | C22—C21—H212 | 108.9 |
C11—C12—H121 | 108.6 | H211—C21—H212 | 107.7 |
C13—C12—H122 | 108.6 | C21—C22—H223 | 109.5 |
C11—C12—H122 | 108.6 | C21—C22—H222 | 109.5 |
H121—C12—H122 | 107.6 | H223—C22—H222 | 109.5 |
C12—C13—C15 | 112.7 (6) | C21—C22—H221 | 109.5 |
C12—C13—C14 | 109.7 (6) | H223—C22—H221 | 109.5 |
C15—C13—C14 | 108.4 (7) | H222—C22—H221 | 109.5 |
| | | |
C2—N1—C1—O1 | 1.9 (5) | O1—C1—C11—C12 | 53.8 (5) |
C2—N1—C1—C11 | −176.9 (3) | N1—C1—C11—C12 | −127.3 (4) |
C21—N2—C2—O2 | −0.4 (5) | C1—C11—C12—C13 | 68.3 (6) |
C21—N2—C2—N1 | 179.1 (3) | C11—C12—C13—C15 | 64.2 (8) |
C1—N1—C2—O2 | −179.9 (3) | C11—C12—C13—C14 | −174.8 (6) |
C1—N1—C2—N2 | 0.6 (5) | C2—N2—C21—C22 | −83.0 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O1i | 0.86 | 2.39 | 3.083 (3) | 137 |
N1—H11···O2ii | 0.86 | 2.00 | 2.860 (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
C9H18N2O2 | F(000) = 204 |
Mr = 186.25 | Dx = 1.088 Mg m−3 |
Triclinic, P1 | Melting point: 375 K |
a = 8.7157 (12) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.6307 (7) Å | Cell parameters from 2373 reflections |
c = 5.1642 (7) Å | θ = 2.8–27.4° |
α = 89.78 (1)° | µ = 0.08 mm−1 |
β = 90.522 (6)° | T = 366 K |
γ = 88.757 (5)° | Plate, colourless |
V = 568.34 (11) Å3 | 1.00 × 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 tube | Rint = 0.033 |
Graphite monochromator | θmax = 27.5°, θmin = 2.3° |
Detector resolution: 10 pixels mm-1 | h = −11→11 |
Oscillation method scans | k = −16→16 |
6593 measured reflections | l = −6→6 |
2383 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.100 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.342 | H-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 parameters | Δρmax = 0.32 e Å−3 |
5 restraints | Δρmin = −0.35 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.4312 (3) | 0.5736 (2) | 0.2226 (6) | 0.1031 (10) | |
O2 | 0.0275 (3) | 0.4105 (2) | 0.2482 (6) | 0.0982 (10) | |
N1 | 0.1970 (3) | 0.5329 (2) | 0.3746 (6) | 0.0805 (9) | |
H11 | 0.1307 | 0.5513 | 0.4892 | 0.097* | |
N2 | 0.2532 (3) | 0.4167 (2) | 0.0410 (7) | 0.0849 (10) | |
H21 | 0.3401 | 0.4471 | 0.0282 | 0.102* | |
C1 | 0.3274 (4) | 0.5894 (3) | 0.3763 (8) | 0.0797 (10) | |
C2 | 0.1540 (4) | 0.4501 (3) | 0.2168 (8) | 0.0822 (11) | |
C11 | 0.3390 (5) | 0.6702 (3) | 0.5821 (10) | 0.1012 (13) | |
H111 | 0.4173 | 0.6465 | 0.7051 | 0.121* | |
H112 | 0.2423 | 0.6733 | 0.6734 | 0.121* | |
C12 | 0.3760 (7) | 0.7804 (4) | 0.4976 (15) | 0.154 (3) | |
H121 | 0.3992 | 0.8220 | 0.6500 | 0.185* | |
H122 | 0.4675 | 0.7773 | 0.3922 | 0.185* | |
C13 | 0.2512 (9) | 0.8357 (6) | 0.3477 (17) | 0.176 (3) | |
H131 | 0.2261 | 0.7926 | 0.1964 | 0.212* | |
C14 | 0.3096 (17) | 0.9424 (7) | 0.252 (3) | 0.299 (8) | |
H143 | 0.2313 | 0.9775 | 0.1498 | 0.358* | |
H142 | 0.3994 | 0.9309 | 0.1489 | 0.358* | |
H141 | 0.3349 | 0.9857 | 0.3983 | 0.358* | |
C15 | 0.1057 (10) | 0.8541 (9) | 0.503 (3) | 0.271 (6) | |
H153 | 0.0293 | 0.8889 | 0.3954 | 0.325* | |
H151 | 0.1278 | 0.8977 | 0.6496 | 0.325* | |
H152 | 0.0680 | 0.7874 | 0.5609 | 0.325* | |
C21 | 0.2180 (5) | 0.3301 (4) | −0.1300 (9) | 0.1003 (13) | |
H211 | 0.2777 | 0.3365 | −0.2867 | 0.120* | |
H212 | 0.1102 | 0.3348 | −0.1785 | 0.120* | |
C22 | 0.2515 (7) | 0.2241 (4) | −0.0079 (13) | 0.135 (2) | |
H223 | 0.2260 | 0.1692 | −0.1277 | 0.162* | |
H222 | 0.1915 | 0.2169 | 0.1459 | 0.162* | |
H221 | 0.3586 | 0.2183 | 0.0363 | 0.162* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0734 (16) | 0.117 (2) | 0.120 (2) | −0.0134 (14) | 0.0366 (15) | −0.0011 (17) |
O2 | 0.0680 (15) | 0.107 (2) | 0.121 (2) | −0.0110 (13) | 0.0309 (14) | −0.0051 (16) |
N1 | 0.0627 (16) | 0.0837 (19) | 0.096 (2) | −0.0030 (13) | 0.0232 (14) | −0.0002 (16) |
N2 | 0.0622 (16) | 0.092 (2) | 0.101 (2) | −0.0023 (14) | 0.0219 (15) | −0.0020 (17) |
C1 | 0.0637 (18) | 0.082 (2) | 0.093 (2) | 0.0011 (15) | 0.0165 (17) | 0.0163 (18) |
C2 | 0.0587 (17) | 0.091 (2) | 0.097 (3) | 0.0060 (16) | 0.0196 (17) | 0.016 (2) |
C11 | 0.089 (3) | 0.089 (3) | 0.126 (4) | −0.001 (2) | 0.020 (2) | 0.004 (2) |
C12 | 0.145 (5) | 0.119 (4) | 0.201 (7) | −0.007 (4) | 0.053 (5) | −0.008 (4) |
C13 | 0.181 (7) | 0.140 (5) | 0.207 (8) | 0.017 (5) | −0.013 (6) | 0.043 (5) |
C14 | 0.47 (2) | 0.117 (6) | 0.308 (15) | −0.035 (9) | 0.053 (15) | 0.050 (7) |
C15 | 0.140 (8) | 0.223 (10) | 0.45 (2) | 0.056 (7) | −0.018 (10) | 0.008 (11) |
C21 | 0.077 (2) | 0.113 (3) | 0.112 (3) | 0.000 (2) | 0.018 (2) | −0.004 (3) |
C22 | 0.138 (5) | 0.102 (3) | 0.166 (5) | 0.004 (3) | 0.013 (4) | 0.004 (3) |
Geometric parameters (Å, º) top
O1—C1 | 1.222 (4) | C13—C15 | 1.520 (13) |
O2—C2 | 1.233 (4) | C13—C14 | 1.532 (13) |
N1—C1 | 1.355 (5) | C13—H131 | 0.9800 |
N1—C2 | 1.385 (5) | C14—H143 | 0.9600 |
N1—H11 | 0.8600 | C14—H142 | 0.9600 |
N2—C2 | 1.323 (5) | C14—H141 | 0.9600 |
N2—C21 | 1.445 (5) | C15—H153 | 0.9600 |
N2—H21 | 0.8600 | C15—H151 | 0.9600 |
C1—C11 | 1.481 (6) | C15—H152 | 0.9600 |
C11—C12 | 1.499 (7) | C21—C22 | 1.500 (7) |
C11—H111 | 0.9700 | C21—H211 | 0.9700 |
C11—H112 | 0.9700 | C21—H212 | 0.9700 |
C12—C13 | 1.490 (10) | C22—H223 | 0.9600 |
C12—H121 | 0.9700 | C22—H222 | 0.9600 |
C12—H122 | 0.9700 | C22—H221 | 0.9600 |
| | | |
C1—N1—C2 | 129.9 (3) | C12—C13—H131 | 108.4 |
C1—N1—H11 | 115.0 | C15—C13—H131 | 108.4 |
C2—N1—H11 | 115.0 | C14—C13—H131 | 108.4 |
C2—N2—C21 | 121.2 (3) | C13—C14—H143 | 109.5 |
C2—N2—H21 | 119.4 | C13—C14—H142 | 109.5 |
C21—N2—H21 | 119.4 | H143—C14—H142 | 109.5 |
O1—C1—N1 | 122.6 (4) | C13—C14—H141 | 109.5 |
O1—C1—C11 | 121.6 (4) | H143—C14—H141 | 109.5 |
N1—C1—C11 | 115.7 (3) | H142—C14—H141 | 109.5 |
O2—C2—N2 | 123.4 (4) | C13—C15—H153 | 109.5 |
O2—C2—N1 | 118.9 (3) | C13—C15—H151 | 109.5 |
N2—C2—N1 | 117.6 (3) | H153—C15—H151 | 109.5 |
C1—C11—C12 | 116.8 (5) | C13—C15—H152 | 109.5 |
C1—C11—H111 | 108.1 | H153—C15—H152 | 109.5 |
C12—C11—H111 | 108.1 | H151—C15—H152 | 109.5 |
C1—C11—H112 | 108.1 | N2—C21—C22 | 112.4 (4) |
C12—C11—H112 | 108.1 | N2—C21—H211 | 109.1 |
H111—C11—H112 | 107.3 | C22—C21—H211 | 109.1 |
C13—C12—C11 | 114.5 (5) | N2—C21—H212 | 109.1 |
C13—C12—H121 | 108.6 | C22—C21—H212 | 109.1 |
C11—C12—H121 | 108.6 | H211—C21—H212 | 107.9 |
C13—C12—H122 | 108.6 | C21—C22—H223 | 109.5 |
C11—C12—H122 | 108.6 | C21—C22—H222 | 109.5 |
H121—C12—H122 | 107.6 | H223—C22—H222 | 109.5 |
C12—C13—C15 | 113.4 (7) | C21—C22—H221 | 109.5 |
C12—C13—C14 | 108.9 (8) | H223—C22—H221 | 109.5 |
C15—C13—C14 | 109.2 (9) | H222—C22—H221 | 109.5 |
| | | |
C2—N1—C1—O1 | 1.1 (6) | O1—C1—C11—C12 | 53.9 (6) |
C2—N1—C1—C11 | −177.2 (4) | N1—C1—C11—C12 | −127.7 (4) |
C21—N2—C2—O2 | 0.4 (6) | C1—C11—C12—C13 | 69.0 (7) |
C21—N2—C2—N1 | 179.5 (3) | C11—C12—C13—C15 | 63.5 (10) |
C1—N1—C2—O2 | −179.3 (3) | C11—C12—C13—C14 | −174.6 (7) |
C1—N1—C2—N2 | 1.6 (6) | C2—N2—C21—C22 | −83.6 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O1i | 0.86 | 2.40 | 3.085 (4) | 137 |
N1—H11···O2ii | 0.86 | 2.00 | 2.855 (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
C9H18N2O2 | F(000) = 204 |
Mr = 186.25 | Dx = 1.081 Mg m−3 |
Triclinic, P1 | Melting point: 375 K |
a = 8.6912 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.7757 (6) Å | Cell parameters from 2775 reflections |
c = 5.1587 (1) Å | θ = 2.8–27.5° |
α = 88.386 (2)° | µ = 0.08 mm−1 |
β = 91.168 (6)° | T = 368 K |
γ = 88.4630 (19)° | Plate, colourless |
V = 572.24 (4) Å3 | 1.00 × 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 tube | Rint = 0.021 |
Graphite monochromator | θmax = 27.5°, θmin = 2.3° |
Detector resolution: 10 pixels mm-1 | h = −11→11 |
Oscillation method scans | k = −16→16 |
7417 measured reflections | l = −6→6 |
2283 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.099 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.308 | H-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 parameters | Δρmax = 0.24 e Å−3 |
17 restraints | Δρmin = −0.28 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.4310 (3) | 0.5728 (2) | 0.2201 (6) | 0.1095 (11) | |
O2 | 0.0279 (3) | 0.4107 (2) | 0.2539 (6) | 0.1050 (10) | |
N1 | 0.1966 (3) | 0.5326 (2) | 0.3729 (6) | 0.0858 (10) | |
H11 | 0.1302 | 0.5513 | 0.4852 | 0.103* | |
N2 | 0.2532 (3) | 0.4167 (3) | 0.0458 (7) | 0.0928 (10) | |
H21 | 0.3403 | 0.4466 | 0.0329 | 0.111* | |
C1 | 0.3272 (4) | 0.5884 (3) | 0.3710 (7) | 0.0866 (11) | |
C2 | 0.1542 (4) | 0.4496 (3) | 0.2198 (8) | 0.0861 (11) | |
C11A | 0.3370 (5) | 0.6696 (3) | 0.5749 (9) | 0.1098 (14) | 0.874 (6) |
H111 | 0.4138 | 0.6454 | 0.7035 | 0.132* | 0.874 (6) |
H112 | 0.2388 | 0.6729 | 0.6609 | 0.132* | 0.874 (6) |
C12A | 0.3760 (7) | 0.7806 (4) | 0.4893 (15) | 0.158 (3) | 0.874 (6) |
H121 | 0.4671 | 0.7782 | 0.3839 | 0.190* | 0.874 (6) |
H122 | 0.3993 | 0.8208 | 0.6412 | 0.190* | 0.874 (6) |
C13A | 0.2445 (9) | 0.8353 (6) | 0.3344 (16) | 0.179 (4) | 0.874 (6) |
H131 | 0.2167 | 0.7941 | 0.1839 | 0.214* | 0.874 (6) |
C14A | 0.3006 (18) | 0.9430 (6) | 0.245 (3) | 0.288 (8) | 0.874 (6) |
H142 | 0.3886 | 0.9340 | 0.1373 | 0.433* | 0.874 (6) |
H141 | 0.3286 | 0.9824 | 0.3935 | 0.433* | 0.874 (6) |
H143 | 0.2198 | 0.9799 | 0.1477 | 0.433* | 0.874 (6) |
C15A | 0.1029 (11) | 0.8553 (9) | 0.500 (3) | 0.265 (6) | 0.874 (6) |
H153 | 0.0226 | 0.8887 | 0.3940 | 0.397* | 0.874 (6) |
H151 | 0.1296 | 0.8998 | 0.6394 | 0.397* | 0.874 (6) |
H152 | 0.0678 | 0.7898 | 0.5688 | 0.397* | 0.874 (6) |
C11B | 0.3370 (5) | 0.6696 (3) | 0.5749 (9) | 0.1098 (14) | 0.126 (6) |
H113 | 0.4414 | 0.6943 | 0.5864 | 0.132* | 0.126 (6) |
H114 | 0.3120 | 0.6385 | 0.7419 | 0.132* | 0.126 (6) |
C12B | 0.226 (2) | 0.7623 (11) | 0.511 (5) | 0.158 (3) | 0.126 (6) |
H123 | 0.1857 | 0.7549 | 0.3363 | 0.190* | 0.126 (6) |
H124 | 0.1400 | 0.7581 | 0.6276 | 0.190* | 0.126 (6) |
C13B | 0.293 (4) | 0.8711 (8) | 0.531 (7) | 0.179 (4) | 0.126 (6) |
H132 | 0.2095 | 0.9233 | 0.5035 | 0.214* | 0.126 (6) |
C14B | 0.411 (8) | 0.888 (4) | 0.317 (11) | 0.288 (8) | 0.126 (6) |
H144 | 0.4524 | 0.9566 | 0.3303 | 0.433* | 0.126 (6) |
H145 | 0.3611 | 0.8819 | 0.1507 | 0.433* | 0.126 (6) |
H146 | 0.4925 | 0.8361 | 0.3371 | 0.433* | 0.126 (6) |
C15B | 0.368 (6) | 0.888 (3) | 0.797 (10) | 0.265 (6) | 0.126 (6) |
H154 | 0.3793 | 0.9611 | 0.8222 | 0.397* | 0.126 (6) |
H155 | 0.4667 | 0.8526 | 0.8076 | 0.397* | 0.126 (6) |
H156 | 0.3031 | 0.8593 | 0.9295 | 0.397* | 0.126 (6) |
C21 | 0.2181 (5) | 0.3309 (3) | −0.1245 (9) | 0.1067 (14) | |
H211 | 0.2772 | 0.3384 | −0.2811 | 0.128* | |
H212 | 0.1099 | 0.3358 | −0.1742 | 0.128* | |
C22 | 0.2527 (7) | 0.2252 (4) | −0.0027 (12) | 0.145 (2) | |
H223 | 0.2259 | 0.1722 | −0.1225 | 0.174* | |
H222 | 0.1940 | 0.2169 | 0.1517 | 0.174* | |
H221 | 0.3605 | 0.2187 | 0.0409 | 0.174* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0768 (16) | 0.125 (2) | 0.129 (2) | −0.0137 (14) | 0.0384 (16) | −0.0026 (18) |
O2 | 0.0712 (16) | 0.116 (2) | 0.129 (2) | −0.0131 (14) | 0.0339 (15) | −0.0055 (17) |
N1 | 0.0638 (16) | 0.091 (2) | 0.103 (2) | −0.0010 (14) | 0.0245 (15) | 0.0014 (18) |
N2 | 0.0661 (17) | 0.104 (2) | 0.109 (2) | −0.0023 (15) | 0.0234 (16) | −0.0014 (19) |
C1 | 0.068 (2) | 0.085 (2) | 0.106 (3) | 0.0029 (17) | 0.0175 (19) | 0.017 (2) |
C2 | 0.0628 (19) | 0.092 (2) | 0.102 (3) | 0.0040 (17) | 0.0193 (19) | 0.016 (2) |
C11A | 0.092 (3) | 0.099 (3) | 0.139 (4) | 0.001 (2) | 0.022 (3) | 0.004 (3) |
C12A | 0.151 (6) | 0.120 (5) | 0.209 (8) | −0.018 (4) | 0.075 (6) | −0.013 (5) |
C13A | 0.201 (9) | 0.152 (7) | 0.178 (8) | 0.009 (6) | −0.019 (7) | 0.049 (6) |
C14A | 0.48 (2) | 0.098 (6) | 0.287 (14) | −0.008 (8) | 0.042 (14) | 0.056 (7) |
C15A | 0.151 (8) | 0.209 (10) | 0.432 (19) | 0.052 (7) | 0.029 (10) | −0.005 (11) |
C11B | 0.092 (3) | 0.099 (3) | 0.139 (4) | 0.001 (2) | 0.022 (3) | 0.004 (3) |
C12B | 0.151 (6) | 0.120 (5) | 0.209 (8) | −0.018 (4) | 0.075 (6) | −0.013 (5) |
C13B | 0.201 (9) | 0.152 (7) | 0.178 (8) | 0.009 (6) | −0.019 (7) | 0.049 (6) |
C14B | 0.48 (2) | 0.098 (6) | 0.287 (14) | −0.008 (8) | 0.042 (14) | 0.056 (7) |
C15B | 0.151 (8) | 0.209 (10) | 0.432 (19) | 0.052 (7) | 0.029 (10) | −0.005 (11) |
C21 | 0.085 (3) | 0.113 (3) | 0.123 (3) | 0.002 (2) | 0.021 (2) | 0.000 (3) |
C22 | 0.150 (5) | 0.115 (4) | 0.169 (5) | 0.005 (3) | 0.017 (4) | 0.000 (4) |
Geometric parameters (Å, º) top
O1—C1 | 1.219 (4) | C15A—H153 | 0.9600 |
O2—C2 | 1.231 (4) | C15A—H151 | 0.9600 |
N1—C1 | 1.356 (5) | C15A—H152 | 0.9600 |
N1—C2 | 1.393 (5) | C12B—C13B | 1.53 (2) |
N1—H11 | 0.8600 | C12B—H123 | 0.9700 |
N2—C2 | 1.326 (5) | C12B—H124 | 0.9700 |
N2—C21 | 1.459 (6) | C13B—C15B | 1.53 (6) |
N2—H21 | 0.8600 | C13B—C14B | 1.53 (7) |
C1—C11A | 1.501 (6) | C13B—H132 | 0.9800 |
C11A—C12A | 1.522 (6) | C14B—H144 | 0.9600 |
C11A—H111 | 0.9700 | C14B—H145 | 0.9600 |
C11A—H112 | 0.9700 | C14B—H146 | 0.9600 |
C11A—C12B | 1.530 (18) | C15B—H154 | 0.9600 |
C12A—C13A | 1.524 (10) | C15B—H155 | 0.9600 |
C12A—H121 | 0.9700 | C15B—H156 | 0.9600 |
C12A—H122 | 0.9700 | C21—C22 | 1.493 (7) |
C13A—C15A | 1.531 (14) | C21—H211 | 0.9700 |
C13A—C14A | 1.533 (12) | C21—H212 | 0.9700 |
C13A—H131 | 0.9800 | C22—H223 | 0.9600 |
C14A—H142 | 0.9600 | C22—H222 | 0.9600 |
C14A—H141 | 0.9600 | C22—H221 | 0.9600 |
C14A—H143 | 0.9600 | | |
| | | |
C1—N1—C2 | 129.5 (3) | H153—C15A—H151 | 109.5 |
C1—N1—H11 | 115.2 | C13A—C15A—H152 | 109.5 |
C2—N1—H11 | 115.2 | H153—C15A—H152 | 109.5 |
C2—N2—C21 | 121.6 (3) | H151—C15A—H152 | 109.5 |
C2—N2—H21 | 119.2 | C13B—C12B—H123 | 108.3 |
C21—N2—H21 | 119.2 | C13B—C12B—H124 | 108.3 |
O1—C1—N1 | 123.1 (4) | H123—C12B—H124 | 107.4 |
O1—C1—C11A | 122.0 (4) | C12B—C13B—C15B | 111.8 (7) |
N1—C1—C11A | 114.8 (3) | C12B—C13B—C14B | 109.9 (7) |
O2—C2—N2 | 123.7 (4) | C15B—C13B—C14B | 110.4 (7) |
O2—C2—N1 | 118.5 (3) | C12B—C13B—H132 | 108.2 |
N2—C2—N1 | 117.8 (3) | C15B—C13B—H132 | 108.2 |
C1—C11A—C12A | 118.0 (4) | C14B—C13B—H132 | 108.2 |
C1—C11A—H111 | 107.8 | C13B—C14B—H144 | 109.5 |
C12A—C11A—H111 | 107.8 | C13B—C14B—H145 | 109.5 |
C1—C11A—H112 | 107.8 | H144—C14B—H145 | 109.5 |
C12A—C11A—H112 | 107.8 | C13B—C14B—H146 | 109.5 |
H111—C11A—H112 | 107.2 | H144—C14B—H146 | 109.5 |
C11A—C12A—C13A | 112.2 (5) | H145—C14B—H146 | 109.5 |
C11A—C12A—H121 | 109.2 | C13B—C15B—H154 | 109.5 |
C13A—C12A—H121 | 109.2 | C13B—C15B—H155 | 109.5 |
C11A—C12A—H122 | 109.2 | H154—C15B—H155 | 109.5 |
C13A—C12A—H122 | 109.2 | C13B—C15B—H156 | 109.5 |
H121—C12A—H122 | 107.9 | H154—C15B—H156 | 109.5 |
C12A—C13A—C15A | 112.2 (7) | H155—C15B—H156 | 109.5 |
C12A—C13A—C14A | 107.4 (7) | N2—C21—C22 | 113.3 (4) |
C15A—C13A—C14A | 106.7 (10) | N2—C21—H211 | 108.9 |
C12A—C13A—H131 | 110.1 | C22—C21—H211 | 108.9 |
C15A—C13A—H131 | 110.1 | N2—C21—H212 | 108.9 |
C14A—C13A—H131 | 110.1 | C22—C21—H212 | 108.9 |
C13A—C14A—H142 | 109.5 | H211—C21—H212 | 107.7 |
C13A—C14A—H141 | 109.5 | C21—C22—H223 | 109.5 |
H142—C14A—H141 | 109.5 | C21—C22—H222 | 109.5 |
C13A—C14A—H143 | 109.5 | H223—C22—H222 | 109.5 |
H142—C14A—H143 | 109.5 | C21—C22—H221 | 109.5 |
H141—C14A—H143 | 109.5 | H223—C22—H221 | 109.5 |
C13A—C15A—H153 | 109.5 | H222—C22—H221 | 109.5 |
C13A—C15A—H151 | 109.5 | | |
| | | |
C2—N1—C1—O1 | 1.4 (6) | C11A—C12A—C13A—C15A | 66.5 (9) |
C2—N1—C1—C11A | −177.0 (4) | C11A—C12A—C13A—C14A | −176.5 (7) |
C21—N2—C2—O2 | 0.9 (6) | C2—N2—C21—C22 | −84.0 (5) |
C21—N2—C2—N1 | −179.4 (3) | C2—N1—C1—C11B | −177.0 (4) |
C1—N1—C2—O2 | −179.4 (4) | O1—C1—C11B—C12B | 109.5 (13) |
C1—N1—C2—N2 | 0.9 (6) | N1—C1—C11B—C12B | −72.0 (13) |
O1—C1—C11A—C12A | 52.5 (6) | C1—C11B—C12B—C13B | −132.0 (18) |
N1—C1—C11A—C12A | −129.1 (5) | C11B—C12B—C13B—C15B | −55 (3) |
C1—C11A—C12A—C13A | 70.6 (7) | C11B—C12B—C13B—C14B | 68 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O1i | 0.86 | 2.41 | 3.098 (4) | 137 |
N1—H11···O2ii | 0.86 | 2.00 | 2.863 (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
C9H18N2O2 | F(000) = 204 |
Mr = 186.25 | Dx = 1.084 Mg m−3 |
Triclinic, P1 | Melting point: 375 K |
a = 8.605 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.855 (2) Å | Cell parameters from 2605 reflections |
c = 5.1699 (10) Å | θ = 2.9–27.5° |
α = 87.263 (16)° | µ = 0.08 mm−1 |
β = 92.266 (9)° | T = 370 K |
γ = 88.060 (8)° | Plate, colourless |
V = 570.39 (19) Å3 | 1.00 × 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 tube | Rint = 0.031 |
Graphite monochromator | θmax = 27.5°, θmin = 2.4° |
Detector resolution: 10 pixels mm-1 | h = −11→11 |
Oscillation method scans | k = −16→16 |
9055 measured reflections | l = −6→6 |
2263 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.116 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.386 | H-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 parameters | Δρmax = 0.28 e Å−3 |
17 restraints | Δρmin = −0.27 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.4305 (4) | 0.5716 (3) | 0.2153 (8) | 0.1207 (14) | |
O2 | 0.0278 (4) | 0.4110 (3) | 0.2582 (8) | 0.1167 (14) | |
N1 | 0.1965 (4) | 0.5326 (3) | 0.3720 (8) | 0.0955 (13) | |
H11 | 0.1305 | 0.5508 | 0.4836 | 0.115* | |
N2 | 0.2530 (4) | 0.4165 (3) | 0.0519 (8) | 0.1012 (14) | |
H21 | 0.3406 | 0.4461 | 0.0375 | 0.121* | |
C1 | 0.3268 (5) | 0.5873 (4) | 0.3646 (10) | 0.0971 (15) | |
C2 | 0.1552 (5) | 0.4504 (4) | 0.2223 (11) | 0.0985 (15) | |
C11A | 0.3352 (7) | 0.6690 (4) | 0.5612 (11) | 0.124 (2) | 0.813 (8) |
H111 | 0.4121 | 0.6450 | 0.6949 | 0.148* | 0.813 (8) |
H112 | 0.2355 | 0.6728 | 0.6420 | 0.148* | 0.813 (8) |
C12A | 0.3745 (11) | 0.7794 (5) | 0.472 (2) | 0.177 (4) | 0.813 (8) |
H121 | 0.4654 | 0.7767 | 0.3666 | 0.212* | 0.813 (8) |
H122 | 0.3997 | 0.8191 | 0.6216 | 0.212* | 0.813 (8) |
C13A | 0.2393 (13) | 0.8341 (8) | 0.314 (2) | 0.190 (5) | 0.813 (8) |
H131 | 0.2089 | 0.7940 | 0.1649 | 0.228* | 0.813 (8) |
C14A | 0.292 (3) | 0.9422 (9) | 0.226 (4) | 0.333 (12) | 0.813 (8) |
H142 | 0.3805 | 0.9348 | 0.1191 | 0.499* | 0.813 (8) |
H141 | 0.3210 | 0.9802 | 0.3748 | 0.499* | 0.813 (8) |
H143 | 0.2090 | 0.9793 | 0.1283 | 0.499* | 0.813 (8) |
C15A | 0.0990 (16) | 0.8579 (13) | 0.477 (4) | 0.307 (10) | 0.813 (8) |
H153 | 0.0174 | 0.8920 | 0.3691 | 0.461* | 0.813 (8) |
H151 | 0.1291 | 0.9026 | 0.6126 | 0.461* | 0.813 (8) |
H152 | 0.0623 | 0.7940 | 0.5525 | 0.461* | 0.813 (8) |
C11B | 0.3352 (7) | 0.6690 (4) | 0.5612 (11) | 0.124 (2) | 0.187 (8) |
H113 | 0.4408 | 0.6926 | 0.5774 | 0.148* | 0.187 (8) |
H114 | 0.3077 | 0.6393 | 0.7286 | 0.148* | 0.187 (8) |
C12B | 0.224 (2) | 0.7617 (10) | 0.482 (5) | 0.177 (4) | 0.187 (8) |
H123 | 0.1895 | 0.7551 | 0.3029 | 0.212* | 0.187 (8) |
H124 | 0.1336 | 0.7572 | 0.5866 | 0.212* | 0.187 (8) |
C13B | 0.290 (4) | 0.8698 (8) | 0.507 (7) | 0.190 (5) | 0.187 (8) |
H132 | 0.2034 | 0.9212 | 0.4914 | 0.228* | 0.187 (8) |
C14B | 0.399 (8) | 0.893 (4) | 0.286 (10) | 0.333 (12) | 0.187 (8) |
H144 | 0.4386 | 0.9616 | 0.3013 | 0.499* | 0.187 (8) |
H145 | 0.3428 | 0.8897 | 0.1230 | 0.499* | 0.187 (8) |
H146 | 0.4843 | 0.8427 | 0.2957 | 0.499* | 0.187 (8) |
C15B | 0.376 (5) | 0.881 (3) | 0.769 (9) | 0.307 (10) | 0.187 (8) |
H154 | 0.3904 | 0.9533 | 0.7959 | 0.461* | 0.187 (8) |
H155 | 0.4749 | 0.8445 | 0.7707 | 0.461* | 0.187 (8) |
H156 | 0.3148 | 0.8518 | 0.9044 | 0.461* | 0.187 (8) |
C21 | 0.2180 (6) | 0.3318 (4) | −0.1106 (12) | 0.1171 (19) | |
H211 | 0.2776 | 0.3384 | −0.2656 | 0.140* | |
H212 | 0.1085 | 0.3371 | −0.1638 | 0.140* | |
C22 | 0.2534 (9) | 0.2264 (5) | 0.0197 (17) | 0.167 (3) | |
H223 | 0.2272 | 0.1734 | −0.0975 | 0.200* | |
H222 | 0.1934 | 0.2187 | 0.1717 | 0.200* | |
H221 | 0.3622 | 0.2198 | 0.0684 | 0.200* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.080 (2) | 0.146 (3) | 0.139 (3) | −0.0148 (19) | 0.037 (2) | −0.006 (2) |
O2 | 0.077 (2) | 0.129 (3) | 0.147 (3) | −0.0122 (18) | 0.034 (2) | −0.011 (2) |
N1 | 0.070 (2) | 0.100 (3) | 0.117 (3) | −0.0018 (19) | 0.025 (2) | −0.001 (2) |
N2 | 0.071 (2) | 0.114 (3) | 0.120 (3) | −0.003 (2) | 0.023 (2) | −0.004 (3) |
C1 | 0.070 (3) | 0.098 (3) | 0.123 (4) | 0.000 (2) | 0.017 (3) | 0.008 (3) |
C2 | 0.062 (2) | 0.114 (4) | 0.119 (4) | 0.005 (2) | 0.027 (2) | 0.016 (3) |
C11A | 0.095 (4) | 0.110 (4) | 0.166 (6) | −0.002 (3) | 0.021 (3) | 0.002 (4) |
C12A | 0.168 (9) | 0.138 (7) | 0.231 (11) | −0.024 (6) | 0.088 (9) | 0.000 (7) |
C13A | 0.191 (11) | 0.173 (9) | 0.197 (12) | −0.007 (8) | −0.029 (9) | 0.054 (9) |
C14A | 0.54 (4) | 0.117 (9) | 0.34 (2) | 0.007 (13) | 0.04 (2) | 0.053 (11) |
C15A | 0.143 (11) | 0.246 (16) | 0.53 (3) | 0.046 (10) | 0.048 (14) | −0.045 (17) |
C11B | 0.095 (4) | 0.110 (4) | 0.166 (6) | −0.002 (3) | 0.021 (3) | 0.002 (4) |
C12B | 0.168 (9) | 0.138 (7) | 0.231 (11) | −0.024 (6) | 0.088 (9) | 0.000 (7) |
C13B | 0.191 (11) | 0.173 (9) | 0.197 (12) | −0.007 (8) | −0.029 (9) | 0.054 (9) |
C14B | 0.54 (4) | 0.117 (9) | 0.34 (2) | 0.007 (13) | 0.04 (2) | 0.053 (11) |
C15B | 0.143 (11) | 0.246 (16) | 0.53 (3) | 0.046 (10) | 0.048 (14) | −0.045 (17) |
C21 | 0.088 (3) | 0.125 (4) | 0.138 (5) | 0.006 (3) | 0.016 (3) | −0.004 (4) |
C22 | 0.153 (7) | 0.126 (5) | 0.222 (9) | 0.008 (5) | 0.020 (6) | −0.018 (6) |
Geometric parameters (Å, º) top
O1—C1 | 1.221 (6) | C15A—H153 | 0.9600 |
O2—C2 | 1.241 (6) | C15A—H151 | 0.9600 |
N1—C1 | 1.345 (6) | C15A—H152 | 0.9600 |
N1—C2 | 1.386 (7) | C12B—C13B | 1.53 (2) |
N1—H11 | 0.8600 | C12B—H123 | 0.9700 |
N2—C2 | 1.321 (6) | C12B—H124 | 0.9700 |
N2—C21 | 1.440 (7) | C13B—C15B | 1.53 (6) |
N2—H21 | 0.8600 | C13B—C14B | 1.53 (7) |
C1—C11A | 1.497 (7) | C13B—H132 | 0.9800 |
C11A—C12A | 1.525 (9) | C14B—H144 | 0.9600 |
C11A—H111 | 0.9700 | C14B—H145 | 0.9600 |
C11A—H112 | 0.9700 | C14B—H146 | 0.9600 |
C11A—C12B | 1.530 (17) | C15B—H154 | 0.9600 |
C12A—C13A | 1.526 (14) | C15B—H155 | 0.9600 |
C12A—H121 | 0.9700 | C15B—H156 | 0.9600 |
C12A—H122 | 0.9700 | C21—C22 | 1.500 (9) |
C13A—C15A | 1.53 (2) | C21—H211 | 0.9700 |
C13A—C14A | 1.532 (18) | C21—H212 | 0.9700 |
C13A—H131 | 0.9800 | C22—H223 | 0.9600 |
C14A—H142 | 0.9600 | C22—H222 | 0.9600 |
C14A—H141 | 0.9600 | C22—H221 | 0.9600 |
C14A—H143 | 0.9600 | | |
| | | |
C1—N1—C2 | 128.1 (4) | H153—C15A—H151 | 109.5 |
C1—N1—H11 | 115.9 | C13A—C15A—H152 | 109.5 |
C2—N1—H11 | 115.9 | H153—C15A—H152 | 109.5 |
C2—N2—C21 | 122.3 (4) | H151—C15A—H152 | 109.5 |
C2—N2—H21 | 118.9 | C13B—C12B—H123 | 108.2 |
C21—N2—H21 | 118.9 | C13B—C12B—H124 | 108.2 |
O1—C1—N1 | 123.7 (5) | H123—C12B—H124 | 107.4 |
O1—C1—C11A | 122.6 (5) | C12B—C13B—C15B | 112.2 (7) |
N1—C1—C11A | 113.7 (4) | C12B—C13B—C14B | 109.9 (7) |
O2—C2—N2 | 122.9 (6) | C15B—C13B—C14B | 110.3 (7) |
O2—C2—N1 | 117.9 (4) | C12B—C13B—H132 | 108.1 |
N2—C2—N1 | 119.2 (4) | C15B—C13B—H132 | 108.1 |
C1—C11A—C12A | 118.6 (6) | C14B—C13B—H132 | 108.1 |
C1—C11A—H111 | 107.7 | C13B—C14B—H144 | 109.5 |
C12A—C11A—H111 | 107.7 | C13B—C14B—H145 | 109.5 |
C1—C11A—H112 | 107.7 | H144—C14B—H145 | 109.5 |
C12A—C11A—H112 | 107.7 | C13B—C14B—H146 | 109.5 |
H111—C11A—H112 | 107.1 | H144—C14B—H146 | 109.5 |
C11A—C12A—C13A | 111.5 (7) | H145—C14B—H146 | 109.5 |
C11A—C12A—H121 | 109.3 | C13B—C15B—H154 | 109.5 |
C13A—C12A—H121 | 109.3 | C13B—C15B—H155 | 109.5 |
C11A—C12A—H122 | 109.3 | H154—C15B—H155 | 109.5 |
C13A—C12A—H122 | 109.3 | C13B—C15B—H156 | 109.5 |
H121—C12A—H122 | 108.0 | H154—C15B—H156 | 109.5 |
C12A—C13A—C15A | 112.9 (10) | H155—C15B—H156 | 109.5 |
C12A—C13A—C14A | 107.4 (11) | N2—C21—C22 | 113.4 (5) |
C15A—C13A—C14A | 103.6 (14) | N2—C21—H211 | 108.9 |
C12A—C13A—H131 | 110.9 | C22—C21—H211 | 108.9 |
C15A—C13A—H131 | 110.9 | N2—C21—H212 | 108.9 |
C14A—C13A—H131 | 110.9 | C22—C21—H212 | 108.9 |
C13A—C14A—H142 | 109.5 | H211—C21—H212 | 107.7 |
C13A—C14A—H141 | 109.5 | C21—C22—H223 | 109.5 |
H142—C14A—H141 | 109.5 | C21—C22—H222 | 109.5 |
C13A—C14A—H143 | 109.5 | H223—C22—H222 | 109.5 |
H142—C14A—H143 | 109.5 | C21—C22—H221 | 109.5 |
H141—C14A—H143 | 109.5 | H223—C22—H221 | 109.5 |
C13A—C15A—H153 | 109.5 | H222—C22—H221 | 109.5 |
C13A—C15A—H151 | 109.5 | | |
| | | |
C2—N1—C1—O1 | 0.7 (8) | C11A—C12A—C13A—C15A | 68.4 (13) |
C2—N1—C1—C11A | −178.1 (5) | C11A—C12A—C13A—C14A | −178.0 (11) |
C21—N2—C2—O2 | 1.3 (8) | C2—N2—C21—C22 | −83.3 (6) |
C21—N2—C2—N1 | −179.8 (5) | C2—N1—C1—C11B | −178.1 (5) |
C1—N1—C2—O2 | −179.2 (4) | O1—C1—C11B—C12B | 107.1 (13) |
C1—N1—C2—N2 | 1.8 (8) | N1—C1—C11B—C12B | −74.1 (12) |
O1—C1—C11A—C12A | 50.8 (8) | C1—C11B—C12B—C13B | −134.6 (18) |
N1—C1—C11A—C12A | −130.3 (6) | C11B—C12B—C13B—C15B | −47 (3) |
C1—C11A—C12A—C13A | 72.2 (10) | C11B—C12B—C13B—C14B | 76 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O1i | 0.86 | 2.42 | 3.107 (5) | 138 |
N1—H11···O2ii | 0.86 | 2.01 | 2.870 (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
C9H18N2O2 | F(000) = 204 |
Mr = 186.25 | Dx = 1.068 Mg m−3 |
Triclinic, P1 | Melting point: 375 K |
a = 8.6137 (18) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.994 (3) Å | Cell parameters from 2962 reflections |
c = 5.1906 (11) Å | θ = 2.8–27.5° |
α = 86.197 (10)° | µ = 0.08 mm−1 |
β = 91.616 (12)° | T = 372 K |
γ = 88.099 (6)° | Plate, colourless |
V = 579.1 (2) Å3 | 1.00 × 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 tube | Rint = 0.040 |
Graphite monochromator | θmax = 27.5°, θmin = 2.8° |
Detector resolution: 10 pixels mm-1 | h = −11→11 |
Oscillation method scans | k = −16→16 |
8178 measured reflections | l = −6→6 |
2312 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.124 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.334 | H-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 parameters | Δρmax = 0.39 e Å−3 |
17 restraints | Δρmin = −0.29 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.4299 (3) | 0.5710 (2) | 0.2076 (6) | 0.1290 (10) | |
O2 | 0.0275 (2) | 0.41152 (19) | 0.2663 (5) | 0.1204 (9) | |
N1 | 0.1962 (3) | 0.5315 (2) | 0.3685 (6) | 0.1017 (9) | |
H11 | 0.1302 | 0.5501 | 0.4793 | 0.122* | |
N2 | 0.2536 (3) | 0.4159 (2) | 0.0604 (6) | 0.1066 (10) | |
H21 | 0.3419 | 0.4445 | 0.0464 | 0.128* | |
C1 | 0.3266 (4) | 0.5868 (2) | 0.3546 (7) | 0.1013 (11) | |
C2 | 0.1551 (4) | 0.4493 (3) | 0.2288 (7) | 0.1005 (10) | |
C11A | 0.3342 (5) | 0.6684 (2) | 0.5442 (8) | 0.1283 (14) | 0.774 (6) |
H111 | 0.4095 | 0.6449 | 0.6797 | 0.154* | 0.774 (6) |
H112 | 0.2338 | 0.6734 | 0.6235 | 0.154* | 0.774 (6) |
C12A | 0.3760 (7) | 0.7768 (3) | 0.4458 (17) | 0.203 (4) | 0.774 (6) |
H121 | 0.4117 | 0.8143 | 0.5903 | 0.243* | 0.774 (6) |
H122 | 0.4606 | 0.7720 | 0.3273 | 0.243* | 0.774 (6) |
C13A | 0.2389 (8) | 0.8363 (6) | 0.3087 (18) | 0.219 (5) | 0.774 (6) |
H131 | 0.2028 | 0.7964 | 0.1663 | 0.263* | 0.774 (6) |
C14A | 0.284 (2) | 0.9425 (7) | 0.195 (3) | 0.382 (11) | 0.774 (6) |
H142 | 0.3715 | 0.9348 | 0.0870 | 0.574* | 0.774 (6) |
H141 | 0.3097 | 0.9854 | 0.3320 | 0.574* | 0.774 (6) |
H143 | 0.1976 | 0.9739 | 0.0932 | 0.574* | 0.774 (6) |
C15A | 0.0997 (13) | 0.8609 (12) | 0.471 (3) | 0.343 (8) | 0.774 (6) |
H153 | 0.0187 | 0.8947 | 0.3623 | 0.515* | 0.774 (6) |
H151 | 0.1302 | 0.9055 | 0.6023 | 0.515* | 0.774 (6) |
H152 | 0.0623 | 0.7981 | 0.5506 | 0.515* | 0.774 (6) |
C11B | 0.3342 (5) | 0.6684 (2) | 0.5442 (8) | 0.1283 (14) | 0.226 (6) |
H113 | 0.4411 | 0.6872 | 0.5726 | 0.154* | 0.226 (6) |
H114 | 0.2940 | 0.6429 | 0.7082 | 0.154* | 0.226 (6) |
C12B | 0.2364 (14) | 0.7629 (5) | 0.434 (3) | 0.203 (4) | 0.226 (6) |
H123 | 0.2284 | 0.7604 | 0.2479 | 0.243* | 0.226 (6) |
H124 | 0.1322 | 0.7575 | 0.4991 | 0.243* | 0.226 (6) |
C13B | 0.2968 (16) | 0.8678 (6) | 0.495 (2) | 0.219 (5) | 0.226 (6) |
H132 | 0.2084 | 0.9173 | 0.4930 | 0.263* | 0.226 (6) |
C14B | 0.408 (3) | 0.904 (2) | 0.287 (4) | 0.382 (11) | 0.226 (6) |
H144 | 0.4415 | 0.9723 | 0.3196 | 0.574* | 0.226 (6) |
H145 | 0.3566 | 0.9061 | 0.1206 | 0.574* | 0.226 (6) |
H146 | 0.4974 | 0.8577 | 0.2904 | 0.574* | 0.226 (6) |
C15B | 0.378 (3) | 0.8645 (19) | 0.761 (3) | 0.343 (8) | 0.226 (6) |
H154 | 0.3968 | 0.9336 | 0.8066 | 0.515* | 0.226 (6) |
H155 | 0.4755 | 0.8264 | 0.7572 | 0.515* | 0.226 (6) |
H156 | 0.3137 | 0.8314 | 0.8874 | 0.515* | 0.226 (6) |
C21 | 0.2183 (4) | 0.3335 (3) | −0.1002 (8) | 0.1250 (14) | |
H211 | 0.2782 | 0.3406 | −0.2555 | 0.150* | |
H212 | 0.1091 | 0.3391 | −0.1519 | 0.150* | |
C22 | 0.2530 (7) | 0.2286 (4) | 0.0324 (12) | 0.171 (2) | |
H223 | 0.2273 | 0.1765 | −0.0827 | 0.205* | |
H222 | 0.1925 | 0.2205 | 0.1845 | 0.205* | |
H221 | 0.3615 | 0.2219 | 0.0803 | 0.205* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0883 (14) | 0.142 (2) | 0.160 (2) | −0.0232 (14) | 0.0507 (15) | −0.0064 (17) |
O2 | 0.0841 (14) | 0.1289 (19) | 0.153 (2) | −0.0235 (13) | 0.0434 (14) | −0.0172 (16) |
N1 | 0.0761 (14) | 0.110 (2) | 0.121 (2) | −0.0094 (14) | 0.0330 (14) | −0.0047 (17) |
N2 | 0.0749 (15) | 0.114 (2) | 0.134 (2) | −0.0090 (14) | 0.0292 (16) | −0.0123 (18) |
C1 | 0.0783 (18) | 0.100 (2) | 0.124 (3) | −0.0042 (16) | 0.0224 (18) | 0.017 (2) |
C2 | 0.0698 (17) | 0.112 (2) | 0.118 (3) | −0.0006 (17) | 0.0233 (18) | 0.007 (2) |
C11A | 0.104 (3) | 0.111 (3) | 0.171 (4) | −0.009 (2) | 0.025 (3) | −0.006 (3) |
C12A | 0.182 (7) | 0.128 (5) | 0.304 (10) | −0.031 (5) | 0.103 (8) | −0.009 (5) |
C13A | 0.230 (9) | 0.173 (7) | 0.241 (11) | −0.039 (6) | −0.060 (8) | 0.074 (7) |
C14A | 0.63 (3) | 0.120 (7) | 0.385 (19) | −0.002 (10) | 0.07 (2) | 0.054 (8) |
C15A | 0.177 (9) | 0.357 (17) | 0.51 (2) | 0.045 (10) | 0.075 (12) | −0.105 (15) |
C11B | 0.104 (3) | 0.111 (3) | 0.171 (4) | −0.009 (2) | 0.025 (3) | −0.006 (3) |
C12B | 0.182 (7) | 0.128 (5) | 0.304 (10) | −0.031 (5) | 0.103 (8) | −0.009 (5) |
C13B | 0.230 (9) | 0.173 (7) | 0.241 (11) | −0.039 (6) | −0.060 (8) | 0.074 (7) |
C14B | 0.63 (3) | 0.120 (7) | 0.385 (19) | −0.002 (10) | 0.07 (2) | 0.054 (8) |
C15B | 0.177 (9) | 0.357 (17) | 0.51 (2) | 0.045 (10) | 0.075 (12) | −0.105 (15) |
C21 | 0.101 (2) | 0.131 (3) | 0.144 (4) | −0.004 (2) | 0.031 (2) | −0.008 (3) |
C22 | 0.178 (5) | 0.141 (4) | 0.193 (5) | 0.007 (3) | 0.006 (4) | −0.014 (4) |
Geometric parameters (Å, º) top
O1—C1 | 1.210 (4) | C15A—H153 | 0.9600 |
O2—C2 | 1.233 (4) | C15A—H151 | 0.9600 |
N1—C1 | 1.354 (4) | C15A—H152 | 0.9600 |
N1—C2 | 1.381 (5) | C12B—C13B | 1.525 (12) |
N1—H11 | 0.8600 | C12B—H123 | 0.9700 |
N2—C2 | 1.319 (4) | C12B—H124 | 0.9700 |
N2—C21 | 1.436 (5) | C13B—C15B | 1.53 (2) |
N2—H21 | 0.8600 | C13B—C14B | 1.53 (3) |
C1—C11A | 1.496 (5) | C13B—H132 | 0.9800 |
C11A—C12A | 1.523 (6) | C14B—H144 | 0.9600 |
C11A—H111 | 0.9700 | C14B—H145 | 0.9600 |
C11A—H112 | 0.9700 | C14B—H146 | 0.9600 |
C11A—C12B | 1.534 (10) | C15B—H154 | 0.9600 |
C12A—C13A | 1.522 (9) | C15B—H155 | 0.9600 |
C12A—H121 | 0.9700 | C15B—H156 | 0.9600 |
C12A—H122 | 0.9700 | C21—C22 | 1.502 (6) |
C13A—C15A | 1.522 (16) | C21—H211 | 0.9700 |
C13A—C14A | 1.530 (14) | C21—H212 | 0.9700 |
C13A—H131 | 0.9800 | C22—H223 | 0.9600 |
C14A—H142 | 0.9600 | C22—H222 | 0.9600 |
C14A—H141 | 0.9600 | C22—H221 | 0.9600 |
C14A—H143 | 0.9600 | | |
| | | |
C1—N1—C2 | 128.7 (3) | H153—C15A—H151 | 109.5 |
C1—N1—H11 | 115.7 | C13A—C15A—H152 | 109.5 |
C2—N1—H11 | 115.7 | H153—C15A—H152 | 109.5 |
C2—N2—C21 | 122.2 (3) | H151—C15A—H152 | 109.5 |
C2—N2—H21 | 118.9 | C13B—C12B—H123 | 108.3 |
C21—N2—H21 | 118.9 | C13B—C12B—H124 | 108.3 |
O1—C1—N1 | 123.8 (3) | H123—C12B—H124 | 107.4 |
O1—C1—C11A | 122.4 (3) | C12B—C13B—C15B | 112.0 (7) |
N1—C1—C11A | 113.8 (3) | C12B—C13B—C14B | 109.5 (7) |
O2—C2—N2 | 123.4 (4) | C15B—C13B—C14B | 109.9 (7) |
O2—C2—N1 | 118.3 (3) | C12B—C13B—H132 | 108.4 |
N2—C2—N1 | 118.3 (3) | C15B—C13B—H132 | 108.4 |
C1—C11A—C12A | 118.2 (4) | C14B—C13B—H132 | 108.4 |
C1—C11A—H111 | 107.8 | C13B—C14B—H144 | 109.5 |
C12A—C11A—H111 | 107.8 | C13B—C14B—H145 | 109.5 |
C1—C11A—H112 | 107.8 | H144—C14B—H145 | 109.5 |
C12A—C11A—H112 | 107.8 | C13B—C14B—H146 | 109.5 |
H111—C11A—H112 | 107.1 | H144—C14B—H146 | 109.5 |
C13A—C12A—C11A | 112.3 (5) | H145—C14B—H146 | 109.5 |
C13A—C12A—H121 | 109.1 | C13B—C15B—H154 | 109.5 |
C11A—C12A—H121 | 109.1 | C13B—C15B—H155 | 109.5 |
C13A—C12A—H122 | 109.1 | H154—C15B—H155 | 109.5 |
C11A—C12A—H122 | 109.1 | C13B—C15B—H156 | 109.5 |
H121—C12A—H122 | 107.9 | H154—C15B—H156 | 109.5 |
C12A—C13A—C15A | 117.0 (8) | H155—C15B—H156 | 109.5 |
C12A—C13A—C14A | 112.3 (9) | N2—C21—C22 | 112.8 (4) |
C15A—C13A—C14A | 103.3 (11) | N2—C21—H211 | 109.0 |
C12A—C13A—H131 | 108.0 | C22—C21—H211 | 109.0 |
C15A—C13A—H131 | 108.0 | N2—C21—H212 | 109.0 |
C14A—C13A—H131 | 108.0 | C22—C21—H212 | 109.0 |
C13A—C14A—H142 | 109.5 | H211—C21—H212 | 107.8 |
C13A—C14A—H141 | 109.5 | C21—C22—H223 | 109.5 |
H142—C14A—H141 | 109.5 | C21—C22—H222 | 109.5 |
C13A—C14A—H143 | 109.5 | H223—C22—H222 | 109.5 |
H142—C14A—H143 | 109.5 | C21—C22—H221 | 109.5 |
H141—C14A—H143 | 109.5 | H223—C22—H221 | 109.5 |
C13A—C15A—H153 | 109.5 | H222—C22—H221 | 109.5 |
C13A—C15A—H151 | 109.5 | | |
| | | |
C2—N1—C1—O1 | 0.6 (6) | C11A—C12A—C13A—C15A | 64.5 (11) |
C2—N1—C1—C11A | −177.8 (3) | C11A—C12A—C13A—C14A | −176.3 (9) |
C21—N2—C2—O2 | 1.7 (5) | C2—N2—C21—C22 | −84.1 (5) |
C21—N2—C2—N1 | −177.6 (3) | C2—N1—C1—C11B | −177.8 (3) |
C1—N1—C2—O2 | −177.8 (3) | O1—C1—C11B—C12B | 100.4 (7) |
C1—N1—C2—N2 | 1.6 (5) | N1—C1—C11B—C12B | −81.1 (7) |
O1—C1—C11A—C12A | 49.9 (5) | C1—C11B—C12B—C13B | −145.1 (10) |
N1—C1—C11A—C12A | −131.7 (4) | C11B—C12B—C13B—C15B | −33.4 (17) |
C1—C11A—C12A—C13A | 78.5 (7) | C11B—C12B—C13B—C14B | 88.8 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O1i | 0.86 | 2.41 | 3.100 (3) | 138 |
N1—H11···O2ii | 0.86 | 2.00 | 2.855 (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
C9H18N2O2 | F(000) = 204 |
Mr = 186.25 | Dx = 1.044 Mg m−3 |
Triclinic, P1 | Melting point: 375 K |
a = 8.6337 (14) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.1782 (16) Å | Cell parameters from 1921 reflections |
c = 5.2242 (18) Å | θ = 1.6–27.4° |
α = 85.948 (12)° | µ = 0.07 mm−1 |
β = 91.71 (2)° | T = 374 K |
γ = 88.030 (13)° | Plate, colourless |
V = 592.2 (2) Å3 | 1.00 × 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 tube | Rint = 0.041 |
Graphite monochromator | θmax = 27.5°, θmin = 2.4° |
Detector resolution: 10 pixels mm-1 | h = −11→11 |
Oscillation method scans | k = −16→16 |
8267 measured reflections | l = −6→6 |
1962 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.152 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.379 | H-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 parameters | Δρmax = 0.22 e Å−3 |
17 restraints | Δρmin = −0.22 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.4309 (4) | 0.5705 (3) | 0.2056 (8) | 0.1487 (15) | |
O2 | 0.0265 (4) | 0.4115 (2) | 0.2684 (8) | 0.1411 (15) | |
N1 | 0.1966 (4) | 0.5311 (3) | 0.3691 (9) | 0.1209 (14) | |
H11 | 0.1319 | 0.5483 | 0.4816 | 0.145* | |
N2 | 0.2533 (4) | 0.4162 (3) | 0.0625 (9) | 0.1289 (16) | |
H21 | 0.3412 | 0.4442 | 0.0446 | 0.155* | |
C1 | 0.3248 (5) | 0.5871 (3) | 0.3521 (10) | 0.1222 (18) | |
C2 | 0.1557 (5) | 0.4510 (4) | 0.2330 (11) | 0.1156 (17) | |
C11A | 0.3332 (6) | 0.6684 (3) | 0.5374 (11) | 0.148 (2) | 0.765 (6) |
H111 | 0.4093 | 0.6458 | 0.6715 | 0.178* | 0.765 (6) |
H112 | 0.2335 | 0.6734 | 0.6174 | 0.178* | 0.765 (6) |
C12A | 0.3736 (9) | 0.7748 (5) | 0.435 (2) | 0.227 (5) | 0.765 (6) |
H122 | 0.4541 | 0.7692 | 0.3107 | 0.272* | 0.765 (6) |
H121 | 0.4154 | 0.8108 | 0.5758 | 0.272* | 0.765 (6) |
C13A | 0.2368 (10) | 0.8371 (7) | 0.309 (2) | 0.248 (7) | 0.765 (6) |
H131 | 0.2004 | 0.7995 | 0.1650 | 0.298* | 0.765 (6) |
C14A | 0.277 (2) | 0.9430 (8) | 0.194 (3) | 0.366 (14) | 0.765 (6) |
H142 | 0.3645 | 0.9369 | 0.0865 | 0.549* | 0.765 (6) |
H141 | 0.3021 | 0.9855 | 0.3304 | 0.549* | 0.765 (6) |
H143 | 0.1898 | 0.9728 | 0.0944 | 0.549* | 0.765 (6) |
C15A | 0.0940 (18) | 0.8608 (14) | 0.463 (5) | 0.396 (14) | 0.765 (6) |
H153 | 0.0151 | 0.8944 | 0.3507 | 0.594* | 0.765 (6) |
H151 | 0.1215 | 0.9043 | 0.5954 | 0.594* | 0.765 (6) |
H152 | 0.0556 | 0.7985 | 0.5390 | 0.594* | 0.765 (6) |
C11B | 0.3332 (6) | 0.6684 (3) | 0.5374 (11) | 0.148 (2) | 0.235 (6) |
H113 | 0.4389 | 0.6904 | 0.5526 | 0.178* | 0.235 (6) |
H114 | 0.3028 | 0.6415 | 0.7054 | 0.178* | 0.235 (6) |
C12B | 0.2253 (14) | 0.7593 (6) | 0.444 (3) | 0.227 (5) | 0.235 (6) |
H123 | 0.2134 | 0.7607 | 0.2588 | 0.272* | 0.235 (6) |
H124 | 0.1240 | 0.7490 | 0.5149 | 0.272* | 0.235 (6) |
C13B | 0.2811 (16) | 0.8627 (6) | 0.517 (2) | 0.248 (7) | 0.235 (6) |
H132 | 0.1928 | 0.9117 | 0.5045 | 0.298* | 0.235 (6) |
C14B | 0.403 (3) | 0.900 (2) | 0.328 (4) | 0.366 (14) | 0.235 (6) |
H144 | 0.4330 | 0.9665 | 0.3660 | 0.549* | 0.235 (6) |
H145 | 0.3604 | 0.9014 | 0.1562 | 0.549* | 0.235 (6) |
H146 | 0.4923 | 0.8537 | 0.3447 | 0.549* | 0.235 (6) |
C15B | 0.350 (4) | 0.856 (2) | 0.791 (3) | 0.396 (14) | 0.235 (6) |
H154 | 0.3691 | 0.9235 | 0.8409 | 0.594* | 0.235 (6) |
H155 | 0.4452 | 0.8164 | 0.7993 | 0.594* | 0.235 (6) |
H156 | 0.2777 | 0.8247 | 0.9059 | 0.594* | 0.235 (6) |
C21 | 0.2164 (6) | 0.3329 (4) | −0.0932 (10) | 0.143 (2) | |
H211 | 0.2718 | 0.3396 | −0.2520 | 0.172* | |
H212 | 0.1062 | 0.3359 | −0.1364 | 0.172* | |
C22 | 0.2604 (9) | 0.2311 (4) | 0.0485 (16) | 0.204 (4) | |
H223 | 0.2366 | 0.1772 | −0.0590 | 0.245* | |
H222 | 0.2031 | 0.2235 | 0.2029 | 0.245* | |
H221 | 0.3695 | 0.2281 | 0.0914 | 0.245* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.102 (2) | 0.168 (3) | 0.182 (3) | −0.029 (2) | 0.051 (2) | −0.024 (3) |
O2 | 0.094 (2) | 0.140 (3) | 0.196 (4) | −0.0257 (18) | 0.052 (2) | −0.027 (2) |
N1 | 0.083 (2) | 0.124 (3) | 0.160 (4) | −0.021 (2) | 0.039 (3) | −0.018 (3) |
N2 | 0.087 (2) | 0.132 (3) | 0.173 (4) | −0.013 (2) | 0.039 (3) | −0.026 (3) |
C1 | 0.084 (3) | 0.116 (3) | 0.165 (5) | 0.003 (3) | 0.027 (3) | 0.007 (3) |
C2 | 0.064 (2) | 0.138 (4) | 0.142 (5) | 0.003 (3) | 0.015 (3) | 0.010 (3) |
C11A | 0.115 (4) | 0.119 (4) | 0.213 (6) | −0.017 (3) | 0.030 (4) | −0.018 (4) |
C12A | 0.187 (9) | 0.172 (7) | 0.325 (14) | −0.015 (7) | 0.108 (11) | 0.005 (8) |
C13A | 0.204 (11) | 0.269 (12) | 0.248 (14) | −0.030 (10) | −0.074 (11) | 0.118 (12) |
C14A | 0.62 (4) | 0.131 (9) | 0.34 (2) | −0.042 (13) | −0.03 (2) | 0.072 (10) |
C15A | 0.181 (13) | 0.35 (2) | 0.68 (4) | 0.033 (13) | 0.10 (2) | −0.17 (2) |
C11B | 0.115 (4) | 0.119 (4) | 0.213 (6) | −0.017 (3) | 0.030 (4) | −0.018 (4) |
C12B | 0.187 (9) | 0.172 (7) | 0.325 (14) | −0.015 (7) | 0.108 (11) | 0.005 (8) |
C13B | 0.204 (11) | 0.269 (12) | 0.248 (14) | −0.030 (10) | −0.074 (11) | 0.118 (12) |
C14B | 0.62 (4) | 0.131 (9) | 0.34 (2) | −0.042 (13) | −0.03 (2) | 0.072 (10) |
C15B | 0.181 (13) | 0.35 (2) | 0.68 (4) | 0.033 (13) | 0.10 (2) | −0.17 (2) |
C21 | 0.103 (4) | 0.149 (4) | 0.178 (6) | 0.000 (3) | 0.037 (4) | −0.007 (4) |
C22 | 0.192 (7) | 0.147 (5) | 0.278 (10) | −0.009 (5) | 0.043 (8) | −0.039 (6) |
Geometric parameters (Å, º) top
O1—C1 | 1.234 (6) | C15A—H153 | 0.9600 |
O2—C2 | 1.261 (6) | C15A—H151 | 0.9600 |
N1—C1 | 1.353 (6) | C15A—H152 | 0.9600 |
N1—C2 | 1.364 (7) | C12B—C13B | 1.530 (13) |
N1—H11 | 0.8600 | C12B—H123 | 0.9700 |
N2—C2 | 1.338 (6) | C12B—H124 | 0.9700 |
N2—C21 | 1.450 (7) | C13B—C15B | 1.53 (2) |
N2—H21 | 0.8600 | C13B—C14B | 1.53 (3) |
C1—C11A | 1.496 (7) | C13B—H132 | 0.9800 |
C11A—C12A | 1.521 (9) | C14B—H144 | 0.9600 |
C11A—H111 | 0.9700 | C14B—H145 | 0.9600 |
C11A—H112 | 0.9700 | C14B—H146 | 0.9600 |
C11A—C12B | 1.53 (11) | C15B—H154 | 0.9600 |
C12A—C13A | 1.521 (12) | C15B—H155 | 0.9600 |
C12A—H122 | 0.9700 | C15B—H156 | 0.9600 |
C12A—H121 | 0.9700 | C21—C22 | 1.517 (8) |
C13A—C15A | 1.53 (2) | C21—H211 | 0.9700 |
C13A—C14A | 1.534 (16) | C21—H212 | 0.9700 |
C13A—H131 | 0.9800 | C22—H223 | 0.9600 |
C14A—H142 | 0.9600 | C22—H222 | 0.9600 |
C14A—H141 | 0.9600 | C22—H221 | 0.9600 |
C14A—H143 | 0.9600 | | |
| | | |
C1—N1—C2 | 129.1 (4) | H153—C15A—H151 | 109.5 |
C1—N1—H11 | 115.5 | C13A—C15A—H152 | 109.5 |
C2—N1—H11 | 115.5 | H153—C15A—H152 | 109.5 |
C2—N2—C21 | 122.5 (4) | H151—C15A—H152 | 109.5 |
C2—N2—H21 | 118.8 | C13B—C12B—H123 | 108.6 |
C21—N2—H21 | 118.8 | C13B—C12B—H124 | 108.6 |
O1—C1—N1 | 123.6 (4) | H123—C12B—H124 | 107.6 |
O1—C1—C11A | 121.8 (4) | C12B—C13B—C15B | 111.2 (7) |
N1—C1—C11A | 114.5 (4) | C12B—C13B—C14B | 109.3 (7) |
O2—C2—N2 | 121.1 (6) | C15B—C13B—C14B | 109.9 (7) |
O2—C2—N1 | 119.6 (4) | C12B—C13B—H132 | 108.8 |
N2—C2—N1 | 119.3 (4) | C15B—C13B—H132 | 108.8 |
C1—C11A—C12A | 118.1 (6) | C14B—C13B—H132 | 108.8 |
C1—C11A—H111 | 107.8 | C13B—C14B—H144 | 109.5 |
C12A—C11A—H111 | 107.8 | C13B—C14B—H145 | 109.5 |
C1—C11A—H112 | 107.8 | H144—C14B—H145 | 109.5 |
C12A—C11A—H112 | 107.8 | C13B—C14B—H146 | 109.5 |
H111—C11A—H112 | 107.1 | H144—C14B—H146 | 109.5 |
C11A—C12A—C13A | 113.9 (6) | H145—C14B—H146 | 109.5 |
C11A—C12A—H122 | 108.8 | C13B—C15B—H154 | 109.5 |
C13A—C12A—H122 | 108.8 | C13B—C15B—H155 | 109.5 |
C11A—C12A—H121 | 108.8 | H154—C15B—H155 | 109.5 |
C13A—C12A—H121 | 108.8 | C13B—C15B—H156 | 109.5 |
H122—C12A—H121 | 107.7 | H154—C15B—H156 | 109.5 |
C12A—C13A—C15A | 120.4 (12) | H155—C15B—H156 | 109.5 |
C12A—C13A—C14A | 114.5 (10) | N2—C21—C22 | 110.9 (5) |
C15A—C13A—C14A | 102.2 (13) | N2—C21—H211 | 109.5 |
C12A—C13A—H131 | 106.3 | C22—C21—H211 | 109.5 |
C15A—C13A—H131 | 106.3 | N2—C21—H212 | 109.5 |
C14A—C13A—H131 | 106.3 | C22—C21—H212 | 109.5 |
C13A—C14A—H142 | 109.5 | H211—C21—H212 | 108.0 |
C13A—C14A—H141 | 109.5 | C21—C22—H223 | 109.5 |
H142—C14A—H141 | 109.5 | C21—C22—H222 | 109.5 |
C13A—C14A—H143 | 109.5 | H223—C22—H222 | 109.5 |
H142—C14A—H143 | 109.5 | C21—C22—H221 | 109.5 |
H141—C14A—H143 | 109.5 | H223—C22—H221 | 109.5 |
C13A—C15A—H153 | 109.5 | H222—C22—H221 | 109.5 |
C13A—C15A—H151 | 109.5 | | |
| | | |
C2—N1—C1—O1 | −2.0 (9) | C11A—C12A—C13A—C15A | 60.1 (16) |
C2—N1—C1—C11A | −178.7 (5) | C11A—C12A—C13A—C14A | −177.4 (11) |
C21—N2—C2—O2 | 1.0 (7) | C2—N2—C21—C22 | −86.2 (6) |
C21—N2—C2—N1 | −178.6 (5) | C2—N1—C1—C11B | −178.7 (5) |
C1—N1—C2—O2 | −176.5 (5) | O1—C1—C11B—C12B | 106.2 (9) |
C1—N1—C2—N2 | 3.1 (8) | N1—C1—C11B—C12B | −77.1 (8) |
O1—C1—C11A—C12A | 51.0 (7) | C1—C11B—C12B—C13B | −148.3 (10) |
N1—C1—C11A—C12A | −132.3 (6) | C11B—C12B—C13B—C15B | −40.8 (18) |
C1—C11A—C12A—C13A | 81.4 (10) | C11B—C12B—C13B—C14B | 80.6 (18) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O1i | 0.86 | 2.40 | 3.107 (5) | 139 |
N1—H11···O2ii | 0.86 | 2.00 | 2.862 (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
C10H20N2O2 | F(000) = 220 |
Mr = 200.28 | Dx = 1.123 Mg m−3 |
Triclinic, P1 | Melting point: 381 K |
a = 9.5437 (19) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.205 (4) Å | Cell parameters from 3224 reflections |
c = 4.8457 (13) Å | θ = 2.5–27.5° |
α = 92.029 (14)° | µ = 0.08 mm−1 |
β = 98.767 (9)° | T = 98 K |
γ = 78.875 (17)° | Plate, colourless |
V = 592.2 (3) Å3 | 0.50 × 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 tube | Rint = 0.051 |
Graphite monochromator | θmax = 27.5°, θmin = 2.2° |
Detector resolution: 10 pixels mm-1 | h = −11→12 |
Oscillation method scans | k = −16→17 |
6949 measured reflections | l = −6→6 |
2162 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.062 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.168 | All 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 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.11921 (18) | 0.55649 (14) | −0.0569 (4) | 0.0314 (4) | |
O2 | 0.40312 (18) | 0.41157 (13) | 0.6112 (3) | 0.0297 (4) | |
N1 | 0.3321 (2) | 0.52101 (15) | 0.2434 (4) | 0.0245 (4) | |
H11 | 0.422 (4) | 0.542 (2) | 0.292 (6) | 0.042 (8)* | |
N2 | 0.1782 (2) | 0.41817 (16) | 0.3633 (4) | 0.0271 (5) | |
H21 | 0.115 (4) | 0.445 (2) | 0.224 (7) | 0.041 (8)* | |
C1 | 0.2423 (2) | 0.57155 (18) | 0.0234 (5) | 0.0248 (5) | |
C2 | 0.3061 (2) | 0.44630 (17) | 0.4180 (5) | 0.0246 (5) | |
C11 | 0.3039 (3) | 0.65149 (18) | −0.1090 (5) | 0.0252 (5) | |
H111 | 0.414 (3) | 0.626 (2) | −0.111 (6) | 0.042 (8)* | |
H112 | 0.255 (3) | 0.662 (2) | −0.304 (6) | 0.029 (7)* | |
C12 | 0.2811 (3) | 0.75336 (19) | 0.0561 (5) | 0.0296 (5) | |
H121 | 0.336 (3) | 0.744 (2) | 0.247 (6) | 0.034 (7)* | |
H122 | 0.174 (4) | 0.773 (2) | 0.079 (7) | 0.049 (9)* | |
C13 | 0.3259 (3) | 0.84217 (19) | −0.0817 (6) | 0.0318 (6) | |
H131 | 0.268 (3) | 0.851 (2) | −0.267 (6) | 0.037 (8)* | |
C14 | 0.2853 (4) | 0.9422 (2) | 0.0804 (8) | 0.0484 (8) | |
H141 | 0.177 (4) | 0.960 (3) | 0.084 (7) | 0.059 (10)* | |
H142 | 0.308 (4) | 1.002 (3) | −0.020 (8) | 0.064 (11)* | |
H143 | 0.336 (4) | 0.935 (3) | 0.277 (9) | 0.070 (11)* | |
C15 | 0.4853 (3) | 0.8202 (3) | −0.1093 (8) | 0.0471 (8) | |
H151 | 0.512 (5) | 0.880 (3) | −0.185 (8) | 0.079 (13)* | |
H152 | 0.539 (4) | 0.809 (3) | 0.077 (7) | 0.051 (10)* | |
H153 | 0.510 (4) | 0.755 (3) | −0.239 (7) | 0.061 (10)* | |
C21 | 0.1370 (3) | 0.34246 (19) | 0.5315 (5) | 0.0270 (5) | |
H211 | 0.204 (3) | 0.333 (2) | 0.707 (6) | 0.032 (7)* | |
H212 | 0.037 (3) | 0.369 (2) | 0.581 (6) | 0.032 (7)* | |
C22 | 0.1387 (3) | 0.2395 (2) | 0.3795 (6) | 0.0338 (6) | |
H221 | 0.241 (4) | 0.210 (2) | 0.341 (7) | 0.045 (8)* | |
H222 | 0.080 (4) | 0.252 (3) | 0.189 (7) | 0.057 (10)* | |
C23 | 0.0812 (4) | 0.1644 (2) | 0.5410 (7) | 0.0403 (7) | |
H231 | 0.136 (4) | 0.153 (3) | 0.729 (7) | 0.049 (9)* | |
H232 | 0.084 (4) | 0.096 (3) | 0.456 (7) | 0.063 (11)* | |
H233 | −0.019 (4) | 0.195 (3) | 0.572 (7) | 0.053 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0236 (9) | 0.0398 (10) | 0.0299 (9) | −0.0107 (7) | −0.0062 (7) | 0.0047 (7) |
O2 | 0.0252 (9) | 0.0352 (9) | 0.0268 (9) | −0.0087 (7) | −0.0067 (7) | 0.0045 (7) |
N1 | 0.0221 (10) | 0.0286 (10) | 0.0233 (10) | −0.0094 (8) | −0.0014 (8) | 0.0010 (7) |
N2 | 0.0236 (11) | 0.0332 (11) | 0.0244 (10) | −0.0108 (8) | −0.0041 (8) | 0.0038 (8) |
C1 | 0.0228 (12) | 0.0285 (12) | 0.0220 (11) | −0.0052 (9) | 0.0005 (9) | −0.0030 (9) |
C2 | 0.0241 (12) | 0.0287 (11) | 0.0207 (11) | −0.0082 (9) | −0.0010 (9) | −0.0036 (8) |
C11 | 0.0259 (12) | 0.0287 (11) | 0.0209 (11) | −0.0068 (9) | 0.0002 (9) | 0.0006 (8) |
C12 | 0.0344 (14) | 0.0294 (12) | 0.0263 (12) | −0.0087 (10) | 0.0061 (10) | −0.0019 (9) |
C13 | 0.0337 (14) | 0.0298 (13) | 0.0320 (13) | −0.0092 (10) | 0.0008 (11) | 0.0021 (10) |
C14 | 0.062 (2) | 0.0305 (15) | 0.0533 (19) | −0.0095 (14) | 0.0100 (17) | −0.0029 (13) |
C15 | 0.0377 (17) | 0.0450 (17) | 0.064 (2) | −0.0187 (13) | 0.0093 (15) | 0.0040 (15) |
C21 | 0.0249 (12) | 0.0323 (12) | 0.0243 (11) | −0.0099 (9) | −0.0009 (10) | 0.0029 (9) |
C22 | 0.0367 (15) | 0.0318 (13) | 0.0360 (14) | −0.0095 (11) | 0.0122 (12) | −0.0016 (10) |
C23 | 0.0489 (18) | 0.0333 (14) | 0.0438 (17) | −0.0143 (12) | 0.0148 (14) | −0.0007 (12) |
Geometric parameters (Å, º) top
O1—C1 | 1.231 (3) | C13—H131 | 0.98 (3) |
O2—C2 | 1.244 (3) | C14—H141 | 1.01 (4) |
N1—C1 | 1.367 (3) | C14—H142 | 1.02 (4) |
N1—C2 | 1.403 (3) | C14—H143 | 1.00 (4) |
N1—H11 | 0.95 (3) | C15—H151 | 0.97 (4) |
N2—C2 | 1.329 (3) | C15—H152 | 0.97 (4) |
N2—C21 | 1.458 (3) | C15—H153 | 1.06 (4) |
N2—H21 | 0.87 (3) | C21—C22 | 1.522 (4) |
C1—C11 | 1.508 (3) | C21—H211 | 0.98 (3) |
C11—C12 | 1.537 (3) | C21—H212 | 1.01 (3) |
C11—H111 | 1.04 (3) | C22—C23 | 1.515 (4) |
C11—H112 | 0.99 (3) | C22—H221 | 1.03 (3) |
C12—C13 | 1.530 (3) | C22—H222 | 1.00 (4) |
C12—H121 | 0.99 (3) | C23—H231 | 0.98 (3) |
C12—H122 | 1.03 (3) | C23—H232 | 0.98 (4) |
C13—C15 | 1.518 (4) | C23—H233 | 1.00 (4) |
C13—C14 | 1.528 (4) | | |
| | | |
C1—N1—C2 | 128.9 (2) | C13—C14—H141 | 111 (2) |
C1—N1—H11 | 116.0 (18) | C13—C14—H142 | 110 (2) |
C2—N1—H11 | 115.0 (18) | H141—C14—H142 | 105 (3) |
C2—N2—C21 | 122.3 (2) | C13—C14—H143 | 110 (2) |
C2—N2—H21 | 120 (2) | H141—C14—H143 | 109 (3) |
C21—N2—H21 | 117 (2) | H142—C14—H143 | 113 (3) |
O1—C1—N1 | 123.6 (2) | C13—C15—H151 | 110 (3) |
O1—C1—C11 | 122.0 (2) | C13—C15—H152 | 107 (2) |
N1—C1—C11 | 114.4 (2) | H151—C15—H152 | 108 (3) |
O2—C2—N2 | 125.0 (2) | C13—C15—H153 | 111 (2) |
O2—C2—N1 | 118.1 (2) | H151—C15—H153 | 110 (3) |
N2—C2—N1 | 116.9 (2) | H152—C15—H153 | 111 (3) |
C1—C11—C12 | 110.1 (2) | N2—C21—C22 | 111.7 (2) |
C1—C11—H111 | 110.4 (17) | N2—C21—H211 | 108.6 (16) |
C12—C11—H111 | 108.8 (17) | C22—C21—H211 | 110.1 (16) |
C1—C11—H112 | 108.5 (15) | N2—C21—H212 | 110.0 (16) |
C12—C11—H112 | 110.3 (16) | C22—C21—H212 | 109.3 (16) |
H111—C11—H112 | 109 (2) | H211—C21—H212 | 107 (2) |
C13—C12—C11 | 113.5 (2) | C23—C22—C21 | 111.7 (2) |
C13—C12—H121 | 108.4 (16) | C23—C22—H221 | 111.5 (17) |
C11—C12—H121 | 110.0 (16) | C21—C22—H221 | 109.3 (17) |
C13—C12—H122 | 109.8 (18) | C23—C22—H222 | 111 (2) |
C11—C12—H122 | 108.3 (18) | C21—C22—H222 | 109 (2) |
H121—C12—H122 | 107 (2) | H221—C22—H222 | 104 (3) |
C15—C13—C14 | 111.3 (3) | C22—C23—H231 | 111.7 (19) |
C15—C13—C12 | 112.3 (2) | C22—C23—H232 | 115 (2) |
C14—C13—C12 | 109.7 (2) | H231—C23—H232 | 106 (3) |
C15—C13—H131 | 109.7 (17) | C22—C23—H233 | 109.7 (19) |
C14—C13—H131 | 107.0 (17) | H231—C23—H233 | 104 (3) |
C12—C13—H131 | 106.6 (17) | H232—C23—H233 | 110 (3) |
| | | |
C2—N1—C1—O1 | −0.7 (4) | N1—C1—C11—C12 | −83.1 (3) |
C2—N1—C1—C11 | 177.0 (2) | C1—C11—C12—C13 | −173.8 (2) |
C21—N2—C2—O2 | 0.8 (4) | C11—C12—C13—C15 | −61.3 (3) |
C21—N2—C2—N1 | −179.1 (2) | C11—C12—C13—C14 | 174.3 (2) |
C1—N1—C2—O2 | −178.6 (2) | C2—N2—C21—C22 | −106.1 (3) |
C1—N1—C2—N2 | 1.3 (4) | N2—C21—C22—C23 | −174.1 (2) |
O1—C1—C11—C12 | 94.6 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O2i | 0.95 (3) | 1.88 (3) | 2.820 (3) | 178 (3) |
N2—H21···O1ii | 0.87 (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
C10H20N2O2 | F(000) = 220 |
Mr = 200.28 | Dx = 1.017 Mg m−3 |
Triclinic, P1 | Melting point: 381 K |
a = 9.547 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.688 (6) Å | Cell parameters from 3480 reflections |
c = 5.1166 (16) Å | θ = 1.5–27.2° |
α = 90.902 (14)° | µ = 0.07 mm−1 |
β = 97.109 (8)° | T = 298 K |
γ = 80.47 (2)° | Plate, colourless |
V = 654.3 (4) Å3 | 0.50 × 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 tube | Rint = 0.071 |
Graphite monochromator | θmax = 27.5°, θmin = 2.2° |
Detector resolution: 10 pixels mm-1 | h = −12→12 |
Oscillation method scans | k = −17→17 |
10255 measured reflections | l = −6→6 |
2485 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.117 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.377 | H-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 parameters | Δρmax = 0.34 e Å−3 |
6 restraints | Δρmin = −0.32 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.1236 (3) | 0.5584 (3) | −0.0332 (6) | 0.1050 (12) | |
O2 | 0.3975 (3) | 0.4154 (2) | 0.5961 (6) | 0.0975 (11) | |
N1 | 0.3307 (3) | 0.5232 (2) | 0.2512 (6) | 0.0836 (11) | |
H11 | 0.4137 | 0.5401 | 0.2863 | 0.100* | |
N2 | 0.1742 (3) | 0.4212 (3) | 0.3621 (7) | 0.0911 (12) | |
H21 | 0.1154 | 0.4484 | 0.2325 | 0.109* | |
C1 | 0.2437 (4) | 0.5731 (3) | 0.0441 (8) | 0.0811 (11) | |
C2 | 0.3029 (4) | 0.4485 (3) | 0.4130 (8) | 0.0808 (11) | |
C11 | 0.3108 (4) | 0.6517 (3) | −0.0726 (8) | 0.0900 (13) | |
H111 | 0.2751 | 0.6597 | −0.2582 | 0.108* | |
H112 | 0.4137 | 0.6310 | −0.0575 | 0.108* | |
C12 | 0.2772 (5) | 0.7513 (3) | 0.0675 (10) | 0.1093 (16) | |
H121 | 0.1747 | 0.7661 | 0.0737 | 0.131* | |
H122 | 0.3230 | 0.7439 | 0.2478 | 0.131* | |
C13 | 0.3234 (6) | 0.8397 (3) | −0.0551 (13) | 0.134 (2) | |
H131 | 0.2810 | 0.8447 | −0.2399 | 0.160* | |
C14 | 0.2702 (10) | 0.9370 (4) | 0.0806 (19) | 0.217 (5) | |
H141 | 0.1681 | 0.9456 | 0.0758 | 0.261* | |
H143 | 0.2956 | 0.9914 | −0.0094 | 0.261* | |
H142 | 0.3137 | 0.9351 | 0.2604 | 0.261* | |
C15 | 0.4856 (6) | 0.8229 (6) | −0.049 (2) | 0.209 (4) | |
H151 | 0.5138 | 0.8783 | −0.1293 | 0.251* | |
H152 | 0.5156 | 0.7636 | −0.1440 | 0.251* | |
H153 | 0.5297 | 0.8161 | 0.1304 | 0.251* | |
C21 | 0.1313 (4) | 0.3472 (3) | 0.5193 (8) | 0.0930 (14) | |
H211 | 0.0317 | 0.3671 | 0.5449 | 0.112* | |
H212 | 0.1878 | 0.3433 | 0.6910 | 0.112* | |
C22 | 0.1503 (6) | 0.2446 (3) | 0.3913 (11) | 0.1219 (18) | |
H221 | 0.0991 | 0.2492 | 0.2148 | 0.146* | |
H222 | 0.2510 | 0.2224 | 0.3769 | 0.146* | |
C23 | 0.0952 (7) | 0.1689 (4) | 0.5501 (15) | 0.150 (2) | |
H232 | 0.1068 | 0.1061 | 0.4624 | 0.180* | |
H231 | −0.0043 | 0.1908 | 0.5653 | 0.180* | |
H233 | 0.1485 | 0.1622 | 0.7225 | 0.180* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0711 (15) | 0.133 (3) | 0.109 (2) | −0.0320 (15) | −0.0182 (15) | 0.031 (2) |
O2 | 0.0768 (16) | 0.109 (2) | 0.104 (2) | −0.0281 (15) | −0.0173 (16) | 0.0273 (17) |
N1 | 0.0662 (16) | 0.100 (3) | 0.085 (2) | −0.0257 (16) | −0.0085 (15) | 0.0091 (18) |
N2 | 0.0703 (17) | 0.112 (3) | 0.093 (2) | −0.0310 (17) | −0.0100 (16) | 0.0215 (19) |
C1 | 0.0654 (17) | 0.098 (3) | 0.080 (2) | −0.0186 (18) | −0.0014 (17) | 0.002 (2) |
C2 | 0.0667 (19) | 0.091 (3) | 0.085 (2) | −0.0214 (18) | −0.0011 (19) | 0.006 (2) |
C11 | 0.087 (2) | 0.099 (3) | 0.086 (2) | −0.019 (2) | 0.011 (2) | 0.009 (2) |
C12 | 0.111 (3) | 0.100 (4) | 0.124 (4) | −0.023 (3) | 0.036 (3) | 0.007 (3) |
C13 | 0.147 (5) | 0.102 (4) | 0.160 (5) | −0.031 (3) | 0.037 (4) | 0.018 (4) |
C14 | 0.271 (12) | 0.101 (5) | 0.298 (11) | −0.032 (6) | 0.105 (10) | 0.005 (6) |
C15 | 0.153 (6) | 0.157 (6) | 0.347 (13) | −0.075 (5) | 0.080 (8) | 0.006 (8) |
C21 | 0.080 (2) | 0.105 (3) | 0.096 (3) | −0.027 (2) | 0.003 (2) | 0.017 (3) |
C22 | 0.122 (4) | 0.106 (4) | 0.144 (4) | −0.024 (3) | 0.035 (4) | 0.006 (3) |
C23 | 0.165 (6) | 0.110 (4) | 0.183 (6) | −0.029 (4) | 0.045 (5) | 0.016 (4) |
Geometric parameters (Å, º) top
O1—C1 | 1.213 (5) | C13—H131 | 0.9800 |
O2—C2 | 1.252 (4) | C14—H141 | 0.9600 |
N1—C1 | 1.377 (5) | C14—H143 | 0.9600 |
N1—C2 | 1.404 (6) | C14—H142 | 0.9600 |
N1—H11 | 0.8600 | C15—H151 | 0.9600 |
N2—C2 | 1.337 (5) | C15—H152 | 0.9600 |
N2—C21 | 1.444 (6) | C15—H153 | 0.9600 |
N2—H21 | 0.8600 | C21—C22 | 1.533 (6) |
C1—C11 | 1.506 (6) | C21—H211 | 0.9700 |
C11—C12 | 1.534 (6) | C21—H212 | 0.9700 |
C11—H111 | 0.9700 | C22—C23 | 1.524 (9) |
C11—H112 | 0.9700 | C22—H221 | 0.9700 |
C12—C13 | 1.524 (7) | C22—H222 | 0.9700 |
C12—H121 | 0.9700 | C23—H232 | 0.9600 |
C12—H122 | 0.9700 | C23—H231 | 0.9600 |
C13—C15 | 1.524 (8) | C23—H233 | 0.9600 |
C13—C14 | 1.532 (9) | | |
| | | |
C1—N1—C2 | 129.2 (3) | C13—C14—H141 | 109.5 |
C1—N1—H11 | 115.4 | C13—C14—H143 | 109.5 |
C2—N1—H11 | 115.4 | H141—C14—H143 | 109.5 |
C2—N2—C21 | 121.7 (3) | C13—C14—H142 | 109.5 |
C2—N2—H21 | 119.2 | H141—C14—H142 | 109.5 |
C21—N2—H21 | 119.2 | H143—C14—H142 | 109.5 |
O1—C1—N1 | 124.3 (4) | C13—C15—H151 | 109.5 |
O1—C1—C11 | 122.7 (4) | C13—C15—H152 | 109.5 |
N1—C1—C11 | 112.9 (3) | H151—C15—H152 | 109.5 |
O2—C2—N2 | 125.5 (4) | C13—C15—H153 | 109.5 |
O2—C2—N1 | 118.1 (3) | H151—C15—H153 | 109.5 |
N2—C2—N1 | 116.4 (3) | H152—C15—H153 | 109.5 |
C1—C11—C12 | 111.3 (3) | N2—C21—C22 | 112.4 (3) |
C1—C11—H111 | 109.4 | N2—C21—H211 | 109.1 |
C12—C11—H111 | 109.4 | C22—C21—H211 | 109.1 |
C1—C11—H112 | 109.4 | N2—C21—H212 | 109.1 |
C12—C11—H112 | 109.4 | C22—C21—H212 | 109.1 |
H111—C11—H112 | 108.0 | H211—C21—H212 | 107.9 |
C13—C12—C11 | 116.1 (4) | C23—C22—C21 | 111.7 (4) |
C13—C12—H121 | 108.3 | C23—C22—H221 | 109.3 |
C11—C12—H121 | 108.3 | C21—C22—H221 | 109.3 |
C13—C12—H122 | 108.3 | C23—C22—H222 | 109.3 |
C11—C12—H122 | 108.3 | C21—C22—H222 | 109.3 |
H121—C12—H122 | 107.4 | H221—C22—H222 | 107.9 |
C12—C13—C15 | 109.9 (4) | C22—C23—H232 | 109.5 |
C12—C13—C14 | 111.9 (4) | C22—C23—H231 | 109.5 |
C15—C13—C14 | 111.1 (6) | H232—C23—H231 | 109.5 |
C12—C13—H131 | 107.9 | C22—C23—H233 | 109.5 |
C15—C13—H131 | 107.9 | H232—C23—H233 | 109.5 |
C14—C13—H131 | 107.9 | H231—C23—H233 | 109.5 |
| | | |
C2—N1—C1—O1 | −0.4 (7) | N1—C1—C11—C12 | −88.8 (5) |
C2—N1—C1—C11 | 177.4 (4) | C1—C11—C12—C13 | −172.6 (4) |
C21—N2—C2—O2 | −0.5 (7) | C11—C12—C13—C15 | −62.5 (8) |
C21—N2—C2—N1 | −178.3 (4) | C11—C12—C13—C14 | 173.6 (6) |
C1—N1—C2—O2 | −178.0 (4) | C2—N2—C21—C22 | −98.4 (5) |
C1—N1—C2—N2 | −0.1 (6) | N2—C21—C22—C23 | −176.1 (5) |
O1—C1—C11—C12 | 89.0 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O2i | 0.86 | 2.02 | 2.873 (4) | 174 |
N2—H21···O1ii | 0.86 | 2.40 | 3.092 (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
C10H20N2O2 | F(000) = 220 |
Mr = 200.28 | Dx = 1.053 Mg m−3 |
Triclinic, P1 | Melting point: 381 K |
a = 9.405 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.3600 (19) Å | Cell parameters from 1956 reflections |
c = 5.1686 (8) Å | θ = 2.2–25.7° |
α = 93.609 (13)° | µ = 0.07 mm−1 |
β = 98.144 (12)° | T = 348 K |
γ = 79.387 (10)° | Plate, colourless |
V = 631.46 (19) Å3 | 0.50 × 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 tube | Rint = 0.078 |
Graphite monochromator | θmax = 27.5°, θmin = 2.2° |
Detector resolution: 10 pixels mm-1 | h = −10→12 |
Oscillation method scans | k = −13→16 |
10152 measured reflections | l = −6→5 |
1576 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.140 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.391 | H-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 parameters | Δρmax = 0.23 e Å−3 |
6 restraints | Δρmin = −0.18 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.1244 (5) | 0.5604 (4) | −0.0247 (11) | 0.123 (2) | |
O2 | 0.3953 (5) | 0.4151 (4) | 0.5898 (11) | 0.118 (2) | |
N1 | 0.3332 (5) | 0.5239 (4) | 0.2559 (12) | 0.0920 (18) | |
H11 | 0.4181 | 0.5404 | 0.2946 | 0.110* | |
N2 | 0.1729 (6) | 0.4231 (4) | 0.3557 (12) | 0.105 (2) | |
H21 | 0.1135 | 0.4495 | 0.2256 | 0.126* | |
C1 | 0.2465 (7) | 0.5732 (5) | 0.0567 (14) | 0.089 (2) | |
C2 | 0.3033 (7) | 0.4487 (5) | 0.4096 (16) | 0.095 (2) | |
C11 | 0.3133 (8) | 0.6498 (5) | −0.0617 (16) | 0.110 (2) | |
H111 | 0.2753 | 0.6552 | −0.2458 | 0.132* | |
H112 | 0.4183 | 0.6279 | −0.0472 | 0.132* | |
C12 | 0.2778 (9) | 0.7532 (5) | 0.0799 (19) | 0.138 (3) | |
H121 | 0.3301 | 0.7499 | 0.2558 | 0.166* | |
H122 | 0.1741 | 0.7682 | 0.0937 | 0.166* | |
C13 | 0.3184 (12) | 0.8392 (6) | −0.060 (2) | 0.170 (4) | |
H131 | 0.2765 | 0.8399 | −0.2447 | 0.204* | |
C14 | 0.267 (2) | 0.9396 (8) | 0.084 (4) | 0.308 (11) | |
H141 | 0.1620 | 0.9515 | 0.0729 | 0.370* | |
H142 | 0.2964 | 0.9943 | 0.0063 | 0.370* | |
H143 | 0.3085 | 0.9361 | 0.2648 | 0.370* | |
C15 | 0.4845 (12) | 0.8228 (9) | −0.028 (3) | 0.266 (9) | |
H151 | 0.5149 | 0.8774 | −0.1057 | 0.319* | |
H152 | 0.5213 | 0.7592 | −0.1127 | 0.319* | |
H153 | 0.5220 | 0.8215 | 0.1548 | 0.319* | |
C21 | 0.1277 (8) | 0.3497 (5) | 0.5162 (16) | 0.118 (3) | |
H211 | 0.0241 | 0.3686 | 0.5281 | 0.141* | |
H212 | 0.1800 | 0.3513 | 0.6917 | 0.141* | |
C22 | 0.1598 (12) | 0.2423 (5) | 0.393 (2) | 0.162 (4) | |
H221 | 0.2640 | 0.2210 | 0.3921 | 0.194* | |
H222 | 0.1121 | 0.2410 | 0.2142 | 0.194* | |
C23 | 0.1023 (15) | 0.1705 (7) | 0.556 (2) | 0.192 (5) | |
H231 | 0.1530 | 0.1702 | 0.7306 | 0.231* | |
H232 | 0.1181 | 0.1028 | 0.4782 | 0.231* | |
H233 | −0.0003 | 0.1935 | 0.5604 | 0.231* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.079 (3) | 0.154 (5) | 0.132 (4) | −0.029 (3) | −0.020 (3) | 0.023 (3) |
O2 | 0.090 (3) | 0.129 (4) | 0.131 (4) | −0.038 (3) | −0.031 (3) | 0.030 (3) |
N1 | 0.068 (3) | 0.103 (4) | 0.106 (4) | −0.030 (3) | −0.005 (3) | 0.007 (4) |
N2 | 0.079 (3) | 0.118 (4) | 0.122 (5) | −0.039 (3) | −0.009 (3) | 0.022 (4) |
C1 | 0.068 (4) | 0.106 (5) | 0.088 (5) | −0.014 (3) | −0.007 (4) | 0.007 (4) |
C2 | 0.067 (4) | 0.101 (5) | 0.114 (6) | −0.024 (4) | −0.007 (4) | −0.006 (4) |
C11 | 0.102 (5) | 0.121 (6) | 0.110 (6) | −0.028 (4) | 0.013 (5) | 0.005 (5) |
C12 | 0.121 (6) | 0.128 (7) | 0.180 (9) | −0.039 (5) | 0.049 (6) | 0.001 (7) |
C13 | 0.173 (10) | 0.123 (7) | 0.227 (13) | −0.043 (7) | 0.048 (9) | 0.006 (8) |
C14 | 0.39 (2) | 0.117 (9) | 0.46 (3) | −0.067 (11) | 0.16 (2) | 0.018 (13) |
C15 | 0.194 (14) | 0.175 (11) | 0.46 (3) | −0.078 (10) | 0.069 (16) | 0.046 (15) |
C21 | 0.081 (4) | 0.150 (7) | 0.122 (6) | −0.037 (4) | −0.004 (4) | 0.001 (6) |
C22 | 0.195 (10) | 0.124 (7) | 0.181 (11) | −0.063 (7) | 0.036 (9) | −0.015 (8) |
C23 | 0.255 (14) | 0.126 (7) | 0.216 (13) | −0.063 (8) | 0.062 (11) | 0.011 (8) |
Geometric parameters (Å, º) top
O1—C1 | 1.206 (8) | C13—H131 | 0.9800 |
O2—C2 | 1.224 (9) | C14—H141 | 0.9600 |
N1—C1 | 1.345 (8) | C14—H142 | 0.9600 |
N1—C2 | 1.410 (10) | C14—H143 | 0.9600 |
N1—H11 | 0.8600 | C15—H151 | 0.9600 |
N2—C2 | 1.320 (9) | C15—H152 | 0.9600 |
N2—C21 | 1.479 (11) | C15—H153 | 0.9600 |
N2—H21 | 0.8600 | C21—C22 | 1.528 (10) |
C1—C11 | 1.496 (11) | C21—H211 | 0.9700 |
C11—C12 | 1.526 (10) | C21—H212 | 0.9700 |
C11—H111 | 0.9700 | C22—C23 | 1.529 (17) |
C11—H112 | 0.9700 | C22—H221 | 0.9700 |
C12—C13 | 1.528 (14) | C22—H222 | 0.9700 |
C12—H121 | 0.9700 | C23—H231 | 0.9600 |
C12—H122 | 0.9700 | C23—H232 | 0.9600 |
C13—C15 | 1.524 (15) | C23—H233 | 0.9600 |
C13—C14 | 1.526 (16) | | |
| | | |
C1—N1—C2 | 128.5 (5) | C13—C14—H141 | 109.5 |
C1—N1—H11 | 115.7 | C13—C14—H142 | 109.5 |
C2—N1—H11 | 115.7 | H141—C14—H142 | 109.5 |
C2—N2—C21 | 120.9 (7) | C13—C14—H143 | 109.5 |
C2—N2—H21 | 119.6 | H141—C14—H143 | 109.5 |
C21—N2—H21 | 119.6 | H142—C14—H143 | 109.5 |
O1—C1—N1 | 125.1 (7) | C13—C15—H151 | 109.5 |
O1—C1—C11 | 120.6 (7) | C13—C15—H152 | 109.5 |
N1—C1—C11 | 114.3 (6) | H151—C15—H152 | 109.5 |
O2—C2—N2 | 124.4 (8) | C13—C15—H153 | 109.5 |
O2—C2—N1 | 118.8 (6) | H151—C15—H153 | 109.5 |
N2—C2—N1 | 116.8 (7) | H152—C15—H153 | 109.5 |
C1—C11—C12 | 109.5 (6) | N2—C21—C22 | 110.0 (6) |
C1—C11—H111 | 109.8 | N2—C21—H211 | 109.7 |
C12—C11—H111 | 109.8 | C22—C21—H211 | 109.7 |
C1—C11—H112 | 109.8 | N2—C21—H212 | 109.7 |
C12—C11—H112 | 109.8 | C22—C21—H212 | 109.7 |
H111—C11—H112 | 108.2 | H211—C21—H212 | 108.2 |
C11—C12—C13 | 112.5 (7) | C21—C22—C23 | 108.0 (7) |
C11—C12—H121 | 109.1 | C21—C22—H221 | 110.1 |
C13—C12—H121 | 109.1 | C23—C22—H221 | 110.1 |
C11—C12—H122 | 109.1 | C21—C22—H222 | 110.1 |
C13—C12—H122 | 109.1 | C23—C22—H222 | 110.1 |
H121—C12—H122 | 107.8 | H221—C22—H222 | 108.4 |
C15—C13—C14 | 107.1 (11) | C22—C23—H231 | 109.5 |
C15—C13—C12 | 106.7 (7) | C22—C23—H232 | 109.5 |
C14—C13—C12 | 108.1 (7) | H231—C23—H232 | 109.5 |
C15—C13—H131 | 111.6 | C22—C23—H233 | 109.5 |
C14—C13—H131 | 111.6 | H231—C23—H233 | 109.5 |
C12—C13—H131 | 111.6 | H232—C23—H233 | 109.5 |
| | | |
C2—N1—C1—O1 | 0.1 (11) | N1—C1—C11—C12 | −89.8 (8) |
C2—N1—C1—C11 | 179.4 (6) | C1—C11—C12—C13 | −169.7 (8) |
C21—N2—C2—O2 | 0.2 (11) | C11—C12—C13—C15 | −69.9 (11) |
C21—N2—C2—N1 | −176.2 (6) | C11—C12—C13—C14 | 175.2 (11) |
C1—N1—C2—O2 | −177.4 (6) | C2—N2—C21—C22 | −93.9 (8) |
C1—N1—C2—N2 | −0.8 (10) | N2—C21—C22—C23 | −176.4 (8) |
O1—C1—C11—C12 | 89.5 (9) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O2i | 0.86 | 1.96 | 2.815 (7) | 175 |
N2—H21···O1ii | 0.86 | 2.35 | 3.043 (8) | 138 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z. |