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The substituted acetyl­acetone 3-[2-(pyridin-4-yl)eth­yl]pentane-2,4-dione, C12H15NO2, (1), with an ethyl­ene bridge between the acetyl­acetone moiety and the heteroaromatic ring, represents an attractive linker for mixed-metal coordination polymers. In the crystal, (1) adopts an anti­periplanar conformation with respect to the C—C bond in the central ethyl­ene group and almost coplanar acetyl­acetone and pyridyl groups. The ditopic mol­ecule exists as the enol tautomer, with proton disorder in the short intra­molecular hydrogen bond. Single-crystal neutron diffraction at 2.5 K indicated site occupancies of 0.602 (17) and 0.398 (17). The geometry of the acetyl­acetone moiety is in agreement with such a site preference of the bridging hydrogen: the O atom associated with the preferred H-atom site subtends the longer [1.305 (2) Å] and the more carbonyl-like O atom the shorter [1.288 (2) Å] C—O bond. Based on structure-factor calculations for the alternative H-atom sites, reflections particularly sensitive for proton distribution were identified and measured in a second neutron data collection at 170 K. At this temperature, 546 independent neutron intensities were used to refine positional and isotropic displacement parameters for a structure model in which parameters for C and O atoms were constrained to those obtained by single-crystal X-ray diffraction at the same temperature. The site occupancies for the disordered proton do not significantly differ from those at 2.5 K.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618015164/lg3228sup1.cif
Contains datablocks 1a, 1b, 1c, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015164/lg32281asup2.hkl
Contains datablock 1a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015164/lg32281bsup3.hkl
Contains datablock 1b

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015164/lg32281csup4.hkl
Contains datablock 1c

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618015164/lg32281asup5.cml
Supplementary material

CCDC references: 1875580; 1875579; 1875578

Computing details top

Data collection: SMART (Bruker, 2001) for (1c). Cell refinement: SMART (Bruker, 2001) for (1c). Data reduction: PRON2013 (Meven, 2013) for (1a), (1b); SAINT-Plus (Bruker, 2009) for (1c). Program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008) for (1c). Program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015) for (1a), (1b); SHELXL2013 (Sheldrick, 2015) for (1c). Molecular graphics: PLATON (Spek, 2009) for (1c). Software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015) for (1c).

3-[2-(Pyridin-4-yl)ethyl]pentane-2,4-dione (1a) top
Crystal data top
C12H15NO2F(000) = 35
Mr = 205.26Dx = 1.255 Mg m3
Monoclinic, C2/cNeutrons radiation, λ = 0.795and 1.171 Å
a = 8.768 (7) ÅCell parameters from 19 reflections
b = 11.115 (2) Åθ = 6.0–13.5°
c = 22.30 (4) ŵ = 0.001 mm1
β = 91.59 (13)°T = 3 K
V = 2172 (5) Å3Prism, colourless
Z = 84.2 × 3.3 × 3.2 mm
Data collection top
Closed Eulerian cradle HEiDi
diffractometer
Rint = 0.041
Radiation source: FRM IIθmax = 39.4°, θmin = 2.0°
rocking scanh = 1414
4136 measured reflectionsk = 1217
2207 independent reflectionsl = 3434
1978 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.038 w = 1/[σ2(Fo2) + (0.065P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.096(Δ/σ)max < 0.001
S = 1.15Δρmax = 0.10 e Å3
2207 reflectionsΔρmin = 0.10 e Å3
271 parametersExtinction correction: SHELXL2017 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraintsExtinction coefficient: 0.41 (3)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.27745 (18)0.92797 (15)0.25978 (7)0.0080 (3)
H1O0.3420 (11)0.9940 (9)0.2840 (4)0.0206 (10)*0.398 (17)
O20.43910 (19)1.03736 (15)0.33185 (7)0.0076 (3)
H2O0.3698 (8)1.0106 (6)0.2941 (3)0.0206 (10)*0.602 (17)
N10.57635 (11)0.29662 (10)0.45206 (4)0.00855 (19)
C10.21255 (16)0.72089 (13)0.26931 (6)0.0079 (3)
H1A0.1634 (5)0.7371 (4)0.22494 (16)0.0316 (8)
H1B0.2873 (4)0.6428 (3)0.26754 (18)0.0308 (8)
H1C0.1218 (4)0.6974 (4)0.29949 (17)0.0315 (8)
C20.29617 (15)0.83142 (13)0.29108 (6)0.0070 (3)
C30.38883 (15)0.83008 (13)0.34453 (6)0.0055 (2)
C40.45797 (15)0.93858 (13)0.36282 (6)0.0061 (2)
C50.55692 (17)0.95075 (14)0.41869 (6)0.0089 (3)
H5A0.6719 (4)0.9199 (5)0.40956 (19)0.0433 (11)
H5B0.5151 (5)0.8984 (4)0.45546 (16)0.0374 (9)
H5C0.5628 (5)1.0450 (4)0.43184 (18)0.0376 (10)
C60.41121 (15)0.71439 (13)0.37969 (6)0.0057 (2)
H6A0.4279 (4)0.7341 (3)0.42756 (13)0.0229 (7)
H6B0.3072 (3)0.6593 (3)0.37601 (15)0.0213 (6)
C70.54798 (15)0.63901 (13)0.35825 (6)0.0071 (2)
H7A0.5349 (4)0.6228 (4)0.30966 (13)0.0246 (7)
H7B0.6542 (4)0.6907 (3)0.36532 (16)0.0240 (7)
C80.56046 (15)0.52005 (13)0.39059 (6)0.0060 (3)
C90.65396 (15)0.50452 (14)0.44198 (6)0.0067 (2)
H90.7237 (4)0.5786 (3)0.45946 (15)0.0245 (7)
C100.65882 (15)0.39257 (14)0.47048 (6)0.0076 (3)
H100.7332 (4)0.3781 (3)0.50958 (14)0.0235 (7)
C110.48603 (16)0.31230 (13)0.40292 (6)0.0076 (3)
H110.4223 (4)0.2328 (3)0.38753 (16)0.0261 (7)
C120.47455 (16)0.42059 (13)0.37119 (6)0.0067 (3)
H120.4012 (4)0.4267 (3)0.33085 (15)0.0233 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0104 (7)0.0066 (7)0.0068 (6)0.0012 (5)0.0030 (5)0.0022 (5)
O20.0114 (7)0.0038 (7)0.0076 (6)0.0008 (5)0.0003 (5)0.0009 (5)
N10.0097 (4)0.0083 (5)0.0076 (4)0.0003 (3)0.0007 (3)0.0023 (3)
C10.0102 (6)0.0054 (6)0.0079 (5)0.0019 (5)0.0013 (5)0.0006 (5)
H1A0.044 (2)0.030 (2)0.0201 (15)0.0085 (16)0.0139 (15)0.0001 (14)
H1B0.0286 (18)0.0207 (19)0.043 (2)0.0043 (13)0.0013 (16)0.0092 (16)
H1C0.0306 (18)0.036 (2)0.0282 (17)0.0105 (16)0.0091 (15)0.0044 (15)
C20.0075 (6)0.0085 (7)0.0050 (6)0.0007 (5)0.0011 (5)0.0004 (4)
C30.0072 (6)0.0050 (7)0.0044 (5)0.0002 (4)0.0005 (4)0.0009 (4)
C40.0066 (6)0.0067 (7)0.0050 (5)0.0002 (4)0.0003 (4)0.0013 (5)
C50.0102 (6)0.0086 (7)0.0078 (6)0.0001 (5)0.0022 (5)0.0025 (5)
H5A0.0187 (16)0.073 (3)0.038 (2)0.0121 (18)0.0070 (15)0.015 (2)
H5B0.047 (2)0.046 (3)0.0188 (15)0.0175 (19)0.0072 (15)0.0114 (16)
H5C0.063 (3)0.0161 (18)0.0330 (19)0.0014 (16)0.0185 (19)0.0078 (14)
C60.0077 (6)0.0040 (6)0.0056 (5)0.0003 (5)0.0019 (4)0.0016 (5)
H6A0.0291 (16)0.0275 (19)0.0120 (12)0.0017 (13)0.0010 (11)0.0025 (11)
H6B0.0149 (14)0.0212 (17)0.0279 (15)0.0036 (11)0.0005 (12)0.0008 (12)
C70.0090 (6)0.0050 (6)0.0075 (5)0.0008 (5)0.0031 (5)0.0020 (5)
H7A0.0319 (17)0.0283 (19)0.0138 (13)0.0049 (13)0.0032 (12)0.0030 (12)
H7B0.0170 (13)0.0203 (16)0.0345 (18)0.0050 (11)0.0004 (13)0.0068 (13)
C80.0076 (5)0.0057 (7)0.0048 (5)0.0011 (4)0.0011 (4)0.0004 (4)
C90.0080 (6)0.0063 (6)0.0058 (5)0.0002 (4)0.0005 (4)0.0008 (4)
H90.0301 (16)0.0191 (17)0.0237 (15)0.0103 (13)0.0075 (13)0.0002 (12)
C100.0098 (6)0.0081 (7)0.0047 (5)0.0003 (5)0.0011 (5)0.0019 (5)
H100.0285 (15)0.0231 (19)0.0183 (14)0.0037 (13)0.0103 (12)0.0044 (12)
C110.0090 (6)0.0062 (7)0.0077 (6)0.0008 (4)0.0010 (5)0.0002 (5)
H110.0313 (17)0.0187 (18)0.0278 (16)0.0091 (13)0.0067 (14)0.0022 (12)
C120.0092 (6)0.0052 (6)0.0058 (5)0.0006 (4)0.0007 (5)0.0004 (4)
H120.0268 (16)0.0238 (18)0.0186 (14)0.0045 (12)0.0092 (12)0.0029 (12)
Geometric parameters (Å, º) top
O1—C21.288 (2)C5—H5C1.088 (4)
O1—H1O1.065 (10)C6—C71.549 (2)
O2—C41.305 (2)C6—H6A1.096 (4)
O2—H2O1.067 (8)C6—H6B1.100 (3)
N1—C111.345 (3)C7—C81.509 (2)
N1—C101.3462 (19)C7—H7A1.101 (4)
C1—C21.504 (2)C7—H7B1.102 (4)
C1—H1A1.083 (4)C8—C121.400 (2)
C1—H1B1.089 (4)C8—C91.401 (3)
C1—H1C1.088 (4)C9—C101.397 (2)
C2—C31.424 (3)C9—H91.091 (4)
C3—C41.405 (2)C10—H101.086 (4)
C3—C61.516 (2)C11—C121.399 (2)
C4—C51.504 (3)C11—H111.095 (4)
C5—H5A1.089 (4)C12—H121.093 (4)
C5—H5B1.078 (4)
C2—O1—H1O103.9 (6)C3—C6—H6A110.3 (2)
C2—O1—H2O100.5 (3)C7—C6—H6A109.0 (2)
C4—O2—H1O100.1 (4)C3—C6—H6B109.8 (2)
C4—O2—H2O104.1 (4)C7—C6—H6B108.9 (2)
C11—N1—C10116.42 (12)H6A—C6—H6B105.8 (3)
C2—C1—H1A109.7 (3)C8—C7—C6111.90 (14)
C2—C1—H1B112.0 (2)C8—C7—H7A109.3 (2)
H1A—C1—H1B108.9 (3)C6—C7—H7A109.4 (2)
C2—C1—H1C110.8 (3)C8—C7—H7B109.8 (2)
H1A—C1—H1C109.0 (3)C6—C7—H7B109.4 (2)
H1B—C1—H1C106.4 (3)H7A—C7—H7B106.9 (3)
O1—C2—C3121.56 (15)C12—C8—C9116.96 (14)
O1—C2—C1116.86 (15)C12—C8—C7120.88 (14)
C3—C2—C1121.56 (13)C9—C8—C7122.14 (13)
C4—C3—C2117.75 (12)C10—C9—C8119.43 (14)
C4—C3—C6121.95 (14)C10—C9—H9120.0 (2)
C2—C3—C6120.30 (13)C8—C9—H9120.6 (2)
O2—C4—C3121.40 (16)N1—C10—C9123.87 (14)
O2—C4—C5115.10 (15)N1—C10—H10115.7 (2)
C3—C4—C5123.49 (12)C9—C10—H10120.5 (2)
C4—C5—H5A109.4 (3)N1—C11—C12123.79 (14)
C4—C5—H5B112.4 (3)N1—C11—H11115.8 (2)
H5A—C5—H5B108.0 (4)C12—C11—H11120.4 (2)
C4—C5—H5C109.4 (2)C8—C12—C11119.52 (15)
H5A—C5—H5C108.4 (4)C8—C12—H12120.3 (2)
H5B—C5—H5C109.2 (4)C11—C12—H12120.1 (2)
C3—C6—C7112.92 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O21.07 (1)1.43 (1)2.438 (4)155 (1)
O2—H2O···O11.07 (1)1.43 (1)2.438 (4)155 (1)
3-[2-(Pyridin-4-yl)ethyl]pentane-2,4-dione (1b) top
Crystal data top
C12H15NO2F(000) = 35
Mr = 205.26Dx = 1.236 Mg m3
Monoclinic, C2/cNeutron radiation, λ = 0.795and 1.171 Å
a = 8.8583 (7) ÅCell parameters from 2722 reflections
b = 11.1031 (9) Åθ = 2.9–29.9°
c = 22.4335 (18) ŵ = 0.001 mm1
β = 91.876 (1)°T = 170 K
V = 2205.3 (3) Å3Prism, colourless
Z = 84.2 × 3.3 × 3.2 mm
Data collection top
Closed Eulerian cradle HEiDi
diffractometer
Rint = 0.040
Radiation source: FRM IIθmax = 39.3°, θmin = 3.3°
rocking scanh = 1213
1048 measured reflectionsk = 016
546 independent reflectionsl = 3434
508 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.060 w = 1/[σ2(Fo2) + (0.001P)2 + 2.P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.147(Δ/σ)max < 0.001
S = 1.22Δρmax = 0.08 e Å3
546 reflectionsΔρmin = 0.08 e Å3
75 parametersExtinction correction: SHELXL2017 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraintsExtinction coefficient: 0.65 (9)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.5750 (9)0.2957 (6)0.4521 (3)0.0340 (16)
O10.2784180.9257720.2604370.038
O20.4423001.0339990.3322920.038
C10.2135870.7202880.2698520.033
C20.2977010.8292650.2918570.026
C30.3904890.8272230.3442340.023
C40.4604160.9352080.3624970.029
C50.5590390.9459890.4177530.040
C60.4124360.7118890.3791160.026
C70.5457180.6359250.3579080.030
C80.5583610.5173080.3904020.026
C90.6516490.5022650.4409400.030
C100.6573190.3912670.4693460.031
C110.4864820.3109560.4031780.034
C120.4740750.4181500.3717060.032
H1O0.331 (6)0.995 (4)0.286 (3)0.049 (8)*0.41 (7)
H2O0.374 (4)1.011 (3)0.2943 (19)0.049 (8)*0.59 (7)
H1A0.169 (3)0.732 (3)0.2262 (13)0.069 (7)*
H1B0.288 (4)0.643 (3)0.2693 (15)0.076 (8)*
H1C0.130 (4)0.693 (3)0.2990 (16)0.075 (8)*
H5A0.663 (6)0.908 (5)0.412 (2)0.125 (17)*
H5B0.513 (4)0.906 (4)0.4561 (17)0.087 (10)*
H5C0.563 (4)1.036 (4)0.4327 (17)0.088 (10)*
H6A0.428 (2)0.7298 (19)0.4284 (10)0.043 (4)*
H6B0.310 (3)0.659 (2)0.3771 (9)0.043 (4)*
H7A0.527 (3)0.619 (2)0.3099 (11)0.052 (5)*
H7B0.650 (3)0.687 (3)0.3653 (13)0.062 (6)*
H90.730 (3)0.575 (3)0.4567 (11)0.056 (6)*
H100.733 (3)0.377 (2)0.5077 (11)0.051 (5)*
H110.426 (3)0.229 (3)0.3896 (14)0.065 (7)*
H120.405 (3)0.423 (3)0.3306 (13)0.061 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.049 (4)0.022 (3)0.031 (3)0.001 (3)0.006 (3)0.008 (2)
O10.0500.0260.0370.0010.0120.009
O20.0490.0190.0450.0060.0060.003
C10.0360.0290.0330.0040.0040.004
C20.0300.0200.0280.0010.0000.001
C30.0270.0170.0250.0000.0000.001
C40.0310.0230.0320.0000.0000.001
C50.0400.0370.0440.0050.0110.007
C60.0310.0200.0260.0030.0010.004
C70.0320.0260.0330.0060.0050.008
C80.0270.0220.0270.0070.0030.002
C90.0300.0270.0310.0010.0010.001
C100.0310.0340.0290.0040.0030.007
C110.0380.0230.0420.0010.0070.002
C120.0370.0290.0310.0060.0080.001
Geometric parameters (Å, º) top
N1—C101.337 (7)C5—H5C1.06 (4)
N1—C111.339 (7)C6—C71.5390
O1—C21.2909C6—H6A1.13 (2)
O1—H1O1.06 (4)C6—H6B1.08 (2)
O2—C41.2965C7—C81.5077
O2—H2O1.06 (4)C7—H7A1.10 (3)
C1—C21.4963C7—H7B1.10 (3)
C1—H1A1.05 (3)C8—C121.3874
C1—H1B1.08 (4)C8—C91.3910
C1—H1C1.05 (3)C9—C101.3876
C2—C31.4119C9—H91.11 (3)
C3—C41.4044C10—H101.08 (3)
C3—C61.5100C11—C121.3864
C4—C51.4977C11—H111.09 (3)
C5—H5A1.02 (6)C12—H121.09 (3)
C5—H5B1.06 (4)
C10—N1—C11115.9 (4)C3—C6—H6A111.6 (11)
C2—O1—H1O105 (2)C7—C6—H6A109.0 (11)
C2—O1—H2O100.8 (13)C3—C6—H6B110.1 (12)
C4—O2—H1O100.6 (17)C7—C6—H6B110.0 (12)
C4—O2—H2O105.8 (18)H6A—C6—H6B102.5 (15)
C2—C1—H1A111.9 (18)C8—C7—C6112.0
C2—C1—H1B110.5 (19)C8—C7—H7A109.1 (14)
H1A—C1—H1B107 (3)C6—C7—H7A107.9 (14)
C2—C1—H1C112 (2)C8—C7—H7B109.4 (15)
H1A—C1—H1C112 (3)C6—C7—H7B108.8 (15)
H1B—C1—H1C103 (3)H7A—C7—H7B110 (2)
O1—C2—C3122.1C12—C8—C9116.8
O1—C2—C1115.8C12—C8—C7121.1
C3—C2—C1122.1C9—C8—C7122.1
C4—C3—C2117.9C10—C9—C8119.5
C4—C3—C6121.7C10—C9—H9118.9 (14)
C2—C3—C6120.4C8—C9—H9121.3 (14)
O2—C4—C3121.6N1—C10—C9124.1 (3)
O2—C4—C5115.1N1—C10—H10115.6 (14)
C3—C4—C5123.3C9—C10—H10120.3 (13)
C4—C5—H5A111 (3)N1—C11—C12124.1 (3)
C4—C5—H5B114 (2)N1—C11—H11112.9 (16)
H5A—C5—H5B108 (4)C12—C11—H11122.9 (16)
C4—C5—H5C111 (2)C11—C12—C8119.6
H5A—C5—H5C114 (4)C11—C12—H12120.4 (16)
H5B—C5—H5C99 (3)C8—C12—H12119.8 (16)
C3—C6—C7113.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O21.06 (4)1.47 (4)2.449151 (4)
O2—H2O···O11.06 (4)1.47 (4)2.449151 (3)
3-[2-(Pyridin-4-yl)ethyl]pentane-2,4-dione (1c) top
Crystal data top
C12H15NO2F(000) = 880
Mr = 205.25Dx = 1.236 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 8.8583 (7) ÅCell parameters from 2722 reflections
b = 11.1031 (9) Åθ = 2.9–29.9°
c = 22.4335 (18) ŵ = 0.08 mm1
β = 91.876 (1)°T = 170 K
V = 2205.3 (3) Å3Block, colourless
Z = 80.19 × 0.18 × 0.18 mm
Data collection top
Bruker APEX CCD area detector
diffractometer
3290 independent reflections
Radiation source: Incoatec microsource2517 reflections with I > 2σ(I)
Multilayer optics monochromatorRint = 0.033
/w scansθmax = 30.7°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1212
Tmin = 0.656, Tmax = 0.746k = 1515
16619 measured reflectionsl = 3131
Refinement top
Refinement on F22 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.052H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.146 w = 1/[σ2(Fo2) + (0.0612P)2 + 1.752P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3290 reflectionsΔρmax = 0.33 e Å3
145 parametersΔρmin = 0.19 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.27842 (13)0.92577 (9)0.26044 (5)0.0380 (3)
O20.44230 (13)1.03400 (9)0.33229 (5)0.0378 (3)
H1O0.323 (4)0.989 (3)0.2812 (16)0.045*0.52 (4)
H2O0.387 (4)1.006 (4)0.2999 (14)0.045*0.48 (4)
N10.57646 (14)0.29558 (10)0.45184 (6)0.0331 (3)
C10.21359 (16)0.72029 (12)0.26985 (7)0.0329 (3)
H1A0.13240.70170.29700.049*
H1B0.28310.65180.26830.049*
H1C0.17030.73610.22990.049*
C20.29770 (15)0.82926 (11)0.29186 (6)0.0262 (3)
C30.39049 (14)0.82722 (10)0.34423 (6)0.0234 (2)
C40.46042 (15)0.93521 (11)0.36250 (6)0.0286 (3)
C50.55904 (18)0.94599 (14)0.41775 (7)0.0404 (4)
H5A0.65840.91120.41050.061*
H5B0.51260.90260.45050.061*
H5C0.57061.03110.42850.061*
C60.41244 (15)0.71189 (11)0.37912 (6)0.0256 (3)
H6A0.31880.66340.37540.031*
H6B0.42980.73180.42180.031*
C70.54572 (15)0.63592 (12)0.35791 (6)0.0304 (3)
H7A0.53230.62060.31460.036*
H7B0.64070.68180.36440.036*
C80.55836 (14)0.51731 (11)0.39040 (6)0.0255 (3)
C90.65165 (15)0.50226 (12)0.44094 (6)0.0295 (3)
H90.71100.56750.45590.035*
C100.65732 (15)0.39127 (13)0.46935 (6)0.0314 (3)
H100.72300.38290.50340.038*
C110.48648 (17)0.31096 (12)0.40318 (7)0.0345 (3)
H110.42770.24440.38940.041*
C120.47408 (16)0.41815 (12)0.37171 (6)0.0323 (3)
H120.40820.42370.33750.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0505 (6)0.0258 (5)0.0370 (6)0.0012 (4)0.0122 (5)0.0088 (4)
O20.0488 (6)0.0187 (4)0.0454 (6)0.0057 (4)0.0056 (5)0.0033 (4)
N10.0365 (6)0.0254 (6)0.0371 (7)0.0055 (5)0.0018 (5)0.0067 (5)
C10.0364 (7)0.0285 (7)0.0335 (7)0.0039 (5)0.0043 (6)0.0044 (5)
C20.0303 (6)0.0203 (6)0.0280 (6)0.0011 (5)0.0000 (5)0.0009 (5)
C30.0272 (6)0.0174 (5)0.0254 (6)0.0002 (4)0.0002 (4)0.0012 (4)
C40.0308 (6)0.0229 (6)0.0322 (7)0.0004 (5)0.0001 (5)0.0010 (5)
C50.0397 (8)0.0366 (8)0.0442 (9)0.0051 (6)0.0114 (7)0.0067 (6)
C60.0307 (6)0.0202 (5)0.0260 (6)0.0032 (5)0.0008 (5)0.0035 (4)
C70.0319 (6)0.0261 (6)0.0334 (7)0.0062 (5)0.0047 (5)0.0084 (5)
C80.0273 (6)0.0223 (6)0.0271 (6)0.0066 (5)0.0027 (5)0.0024 (5)
C90.0303 (6)0.0269 (6)0.0312 (7)0.0007 (5)0.0015 (5)0.0011 (5)
C100.0308 (6)0.0338 (7)0.0293 (7)0.0040 (5)0.0033 (5)0.0067 (5)
C110.0380 (7)0.0233 (6)0.0416 (8)0.0013 (5)0.0066 (6)0.0016 (5)
C120.0366 (7)0.0288 (6)0.0309 (7)0.0065 (5)0.0079 (5)0.0008 (5)
Geometric parameters (Å, º) top
O1—C21.2909 (15)C5—H5C0.9800
O1—H1O0.923 (19)C6—C71.5390 (18)
O2—C41.2965 (16)C6—H6A0.9900
O2—H2O0.919 (19)C6—H6B0.9900
N1—C101.3333 (19)C7—C81.5077 (17)
N1—C111.3413 (18)C7—H7A0.9900
C1—C21.4963 (18)C7—H7B0.9900
C1—H1A0.9800C8—C121.3874 (19)
C1—H1B0.9800C8—C91.3910 (18)
C1—H1C0.9800C9—C101.3876 (18)
C2—C31.4119 (18)C9—H90.9500
C3—C41.4044 (17)C10—H100.9500
C3—C61.5100 (16)C11—C121.3864 (19)
C4—C51.498 (2)C11—H110.9500
C5—H5A0.9800C12—H120.9500
C5—H5B0.9800
C2—O1—H1O108 (3)C7—C6—H6A109.0
C4—O2—H2O100 (3)C3—C6—H6B109.0
C10—N1—C11115.95 (12)C7—C6—H6B109.0
C2—C1—H1A109.5H6A—C6—H6B107.8
C2—C1—H1B109.5C8—C7—C6112.02 (11)
H1A—C1—H1B109.5C8—C7—H7A109.2
C2—C1—H1C109.5C6—C7—H7A109.2
H1A—C1—H1C109.5C8—C7—H7B109.2
H1B—C1—H1C109.5C6—C7—H7B109.2
O1—C2—C3122.06 (11)H7A—C7—H7B107.9
O1—C2—C1115.82 (12)C12—C8—C9116.78 (12)
C3—C2—C1122.11 (11)C12—C8—C7121.08 (12)
C4—C3—C2117.92 (11)C9—C8—C7122.12 (12)
C4—C3—C6121.65 (11)C10—C9—C8119.51 (13)
C2—C3—C6120.43 (11)C10—C9—H9120.2
O2—C4—C3121.60 (12)C8—C9—H9120.2
O2—C4—C5115.07 (12)N1—C10—C9124.15 (13)
C3—C4—C5123.33 (12)N1—C10—H10117.9
C4—C5—H5A109.5C9—C10—H10117.9
C4—C5—H5B109.5N1—C11—C12123.97 (13)
H5A—C5—H5B109.5N1—C11—H11118.0
C4—C5—H5C109.5C12—C11—H11118.0
H5A—C5—H5C109.5C11—C12—C8119.63 (13)
H5B—C5—H5C109.5C11—C12—H12120.2
C3—C6—C7113.06 (10)C8—C12—H12120.2
C3—C6—H6A109.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O20.92 (2)1.61 (3)2.4488 (15)149 (4)
O2—H2O···O10.92 (2)1.56 (2)2.4488 (15)161 (4)
 

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