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The combined study of electron-density features in three substituted hydropyrimidines of the Biginelli compound family has been fulfilled. Results of the low-temperature X-ray diffraction measurements and density functional theory (DFT) B3LYP/6-311++G** calculations of these compounds are described. The experimentally derived atomic and bonding characteristics determined within the quantum-topological theory of atoms in molecules and crystals (QTAIMC) were demonstrated to be fully transferable within chemically similar structures such as the Biginelli compounds. However, for certain covalent bonds they differ significantly from the theoretical results because of insufficient flexibility of the atom-centered multipole electron density model. It was concluded that currently analysis of the theoretical electron density provides a more reliable basis for the determination of the transferability of QTAIMC descriptors for molecular structures. Empirical corrections making the experimentally derived QTAIMC bond descriptors more transferable are proposed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768111033015/eb5011sup1.cif
Contains datablocks I, Imult, II, IImult

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111033015/eb5011Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111033015/eb5011IIsup3.hkl
Contains datablock II

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768111033015/eb5011sup4.pdf
Extra figures and tables

CCDC references: 849847; 849848

Computing details top

Data collection: CrystalClear,(2005) for (I), (II). Cell refinement: Otwinowski & Minor (1997) for (I), (II). Data reduction: SORTAV (Blessing, 1987, 1989,1995) for (I); SORTAV (Blessing, 1987,1989) for (II). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (I), (II). Program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) for (I), (II); Protas, J. (1997). MOLDOS97/MOLLY IBM PC-DOS for Imult, IImult.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
[Figure 11]
(I) top
Crystal data top
C9H14N2OSZ = 2
Mr = 198.28F(000) = 212
Triclinic, P1Dx = 1.303 Mg m3
a = 7.2533 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.8212 (3) ÅCell parameters from 9999 reflections
c = 9.1837 (3) Åθ = 2.3–55.6°
α = 97.187 (1)°µ = 0.28 mm1
β = 100.674 (1)°T = 110 K
γ = 94.106 (1)°Prism, colorless
V = 505.54 (2) Å30.40 × 0.22 × 0.14 mm
Data collection top
Bruker
diffractometer with a SMART 6000 CCD detector
10974 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
ω scansθmax = 55.6°, θmin = 2.3°
Absorption correction: multi-scan
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
h = 1516
Tmin = 0.909, Tmax = 1.106k = 1817
57560 measured reflectionsl = 2121
12868 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: difference Fourier map
wR(F2) = 0.092All H-atom parameters refined
S = 1.08 w = 1/[σ2(Fo2) + (0.0459P)2 + 0.0256P]
where P = (Fo2 + 2Fc2)/3
12868 reflections(Δ/σ)max = 0.001
174 parametersΔρmax = 0.81 e Å3
0 restraintsΔρmin = 0.58 e Å3
Crystal data top
C9H14N2OSγ = 94.106 (1)°
Mr = 198.28V = 505.54 (2) Å3
Triclinic, P1Z = 2
a = 7.2533 (2) ÅMo Kα radiation
b = 7.8212 (3) ŵ = 0.28 mm1
c = 9.1837 (3) ÅT = 110 K
α = 97.187 (1)°0.40 × 0.22 × 0.14 mm
β = 100.674 (1)°
Data collection top
Bruker
diffractometer with a SMART 6000 CCD detector
12868 independent reflections
Absorption correction: multi-scan
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
10974 reflections with I > 2σ(I)
Tmin = 0.909, Tmax = 1.106Rint = 0.042
57560 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.092All H-atom parameters refined
S = 1.08Δρmax = 0.81 e Å3
12868 reflectionsΔρmin = 0.58 e Å3
174 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S0.257791 (11)0.417146 (11)0.100343 (9)0.01531 (2)
O1.09288 (4)0.22556 (6)0.42300 (4)0.02704 (7)
N10.44346 (3)0.27510 (4)0.32474 (3)0.01352 (3)
N30.62324 (4)0.36956 (4)0.16492 (3)0.01422 (3)
C20.45354 (4)0.35047 (4)0.19876 (3)0.01240 (3)
C40.77766 (4)0.27105 (4)0.22534 (3)0.01324 (3)
C4'0.76443 (5)0.09252 (4)0.13056 (4)0.01648 (4)
C4''0.77977 (6)0.10447 (5)0.03140 (4)0.01948 (5)
C50.77282 (4)0.25825 (4)0.38786 (3)0.01344 (4)
C5'0.95553 (4)0.24516 (5)0.48341 (4)0.01607 (4)
C5"0.98389 (5)0.25638 (6)0.65112 (4)0.02109 (6)
C60.60141 (4)0.25116 (4)0.42923 (3)0.01260 (3)
C6'0.55530 (5)0.21774 (5)0.57679 (3)0.01675 (4)
H10.3349 (16)0.2604 (13)0.3451 (11)0.040 (3)*
H30.6343 (14)0.4217 (12)0.0892 (11)0.034 (2)*
H40.8945 (13)0.3399 (11)0.2145 (10)0.026 (2)*
H41'0.8667 (14)0.0271 (12)0.1758 (11)0.032 (2)*
H42'0.6494 (13)0.0269 (11)0.1332 (10)0.029 (2)*
H41"0.8970 (13)0.1695 (12)0.0374 (10)0.031 (2)*
H42"0.7764 (13)0.0103 (11)0.0853 (10)0.028 (2)*
H43"0.6778 (15)0.1612 (13)0.0814 (12)0.038 (3)*
H51"1.1192 (15)0.2792 (13)0.6970 (11)0.037 (2)*
H52"0.9177 (13)0.3497 (12)0.6930 (11)0.030 (2)*
H53"0.9361 (15)0.1501 (13)0.6763 (12)0.040 (3)*
H61'0.5918 (14)0.3127 (12)0.6537 (11)0.034 (2)*
H62'0.4222 (13)0.1842 (12)0.5678 (10)0.027 (2)*
H63'0.6188 (13)0.1226 (12)0.6197 (11)0.029 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.01181 (3)0.01940 (3)0.01626 (3)0.00409 (2)0.00269 (2)0.00708 (2)
O0.01109 (8)0.0521 (2)0.02109 (11)0.00633 (10)0.00525 (7)0.01214 (12)
N10.01003 (7)0.01882 (9)0.01295 (7)0.00205 (6)0.00312 (5)0.00540 (6)
N30.01197 (7)0.01831 (9)0.01487 (8)0.00390 (6)0.00476 (6)0.00728 (6)
C20.01125 (8)0.01405 (8)0.01279 (8)0.00246 (6)0.00296 (6)0.00371 (6)
C40.01071 (8)0.01747 (9)0.01298 (8)0.00278 (6)0.00360 (6)0.00499 (7)
C4'0.01802 (11)0.01742 (10)0.01571 (9)0.00457 (8)0.00502 (8)0.00471 (8)
C4''0.02268 (13)0.02163 (12)0.01444 (10)0.00266 (10)0.00474 (9)0.00180 (8)
C50.01024 (8)0.01875 (9)0.01232 (8)0.00238 (6)0.00278 (6)0.00463 (7)
C5'0.01074 (8)0.02340 (12)0.01483 (9)0.00230 (7)0.00218 (7)0.00572 (8)
C5"0.01588 (11)0.03289 (17)0.01427 (10)0.00558 (10)0.00048 (8)0.00429 (10)
C60.01072 (8)0.01633 (9)0.01147 (7)0.00169 (6)0.00283 (6)0.00354 (6)
C6'0.01504 (10)0.02391 (12)0.01236 (8)0.00149 (8)0.00416 (7)0.00472 (8)
Geometric parameters (Å, º) top
S—C21.6892 (3)C4''—H41"0.973 (9)
O—C5'1.2365 (4)C4''—H42"0.966 (9)
N1—C21.3738 (4)C4''—H43"0.963 (10)
N1—C61.3917 (4)C5—C61.3651 (4)
N1—H10.845 (11)C5—C5'1.4656 (4)
N3—C21.3270 (4)C5'—C5"1.5061 (5)
N3—C41.4684 (4)C5"—H51"0.988 (11)
N3—H30.862 (10)C5"—H52"0.979 (9)
C4—C51.5150 (4)C5"—H53"0.950 (10)
C4—C4'1.5370 (5)C6—C6'1.5036 (4)
C4—H40.999 (9)C6'—H61'0.945 (9)
C4'—C4''1.5257 (5)C6'—H62'0.967 (9)
C4'—H41'0.989 (10)C6'—H63'0.988 (9)
C4'—H42'0.954 (9)
C2—N1—C6123.30 (2)C4'—C4''—H43"111.5 (6)
C2—N1—H1116.0 (7)H41"—C4''—H43"107.4 (8)
C6—N1—H1119.8 (7)H42"—C4''—H43"108.4 (8)
C2—N3—C4122.42 (2)C6—C5—C5'126.60 (3)
C2—N3—H3117.6 (7)C6—C5—C4117.92 (2)
C4—N3—H3118.2 (7)C5'—C5—C4115.39 (2)
N3—C2—N1115.93 (2)O—C5'—C5118.15 (3)
N3—C2—S124.15 (2)O—C5'—C5"118.70 (3)
N1—C2—S119.90 (2)C5—C5'—C5"123.14 (3)
N3—C4—C5108.80 (2)C5'—C5"—H51"110.6 (6)
N3—C4—C4'110.64 (3)C5'—C5"—H52"110.9 (6)
C5—C4—C4'112.46 (2)H51"—C5"—H52"108.3 (8)
N3—C4—H4104.6 (5)C5'—C5"—H53"109.4 (7)
C5—C4—H4111.8 (5)H51"—C5"—H53"108.9 (8)
C4'—C4—H4108.3 (5)H52"—C5"—H53"108.7 (9)
C4''—C4'—C4112.76 (3)C5—C6—N1118.47 (2)
C4''—C4'—H41'108.9 (6)C5—C6—C6'128.51 (3)
C4—C4'—H41'109.1 (5)N1—C6—C6'113.02 (2)
C4''—C4'—H42'109.8 (6)C6—C6'—H61'113.7 (6)
C4—C4'—H42'110.1 (5)C6—C6'—H62'111.5 (5)
H41'—C4'—H42'106.0 (8)H61'—C6'—H62'108.6 (8)
C4'—C4''—H41"111.5 (6)C6—C6'—H63'114.3 (6)
C4'—C4''—H42"109.8 (5)H61'—C6'—H63'103.2 (8)
H41"—C4''—H42"108.1 (8)H62'—C6'—H63'104.7 (8)
(Imult) top
Crystal data top
?β = ?°
Mr = ?γ = ?°
?, ?V = ? Å3
a = ? ÅZ = ?
b = ? Å? radiation, λ = ? Å
c = ? Å × × mm
α = ?°
Data collection top
h = ??l = ??
k = ??
Refinement top
Refinement on F210418 reflections
Least-squares matrix: full275 parameters
R[F2 > 2σ(F2)] = 0.0190 restraints
wR(F2) = 0.030 ' w = 1/[σ2(Fo2) + (0.03P)2 + 2.56P]
where P = (Fo2 + 2Fc2)/3'
S = 1.43
Crystal data top
?β = ?°
Mr = ?γ = ?°
?, ?V = ? Å3
a = ? ÅZ = ?
b = ? Å? radiation, λ = ? Å
c = ? Å × × mm
α = ?°
Data collection top
Refinement top
R[F2 > 2σ(F2)] = 0.01910418 reflections
wR(F2) = 0.030275 parameters
S = 1.430 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S0.25777 (1)0.41714 (1)0.10035 (1)0.016
O1.09233 (4)0.22310 (8)0.42246 (4)0.028
N10.44344 (3)0.27514 (4)0.32472 (3)0.014
N30.62331 (3)0.36956 (4)0.16490 (3)0.015
C20.45356 (4)0.35041 (4)0.19873 (3)0.013
C40.77758 (4)0.27107 (4)0.22533 (3)0.014
C4'0.76432 (5)0.09243 (5)0.13048 (4)0.017
C4"0.77987 (6)0.10450 (6)0.03143 (4)0.020
C50.77280 (4)0.25834 (4)0.38787 (3)0.014
C5'0.95558 (4)0.24494 (5)0.48338 (4)0.016
C5"0.98376 (6)0.25615 (7)0.65110 (4)0.021
C60.60130 (4)0.25115 (4)0.42918 (3)0.013
C6'0.55524 (5)0.21770 (5)0.57670 (3)0.017
H10.313620.257340.348690.022
H30.637080.432280.077250.028
H40.905130.346150.213470.025
H41'0.880920.024880.180780.039
H42'0.632260.020520.136700.036
H41"0.904920.178420.039610.041
H42"0.765080.021060.093560.044
H43"0.662780.163080.084030.053
H51"1.129240.280470.699500.047
H52"0.914320.359380.695470.039
H53"0.929920.137270.678540.044
H61'0.601050.322590.663970.041
H62'0.410590.179410.570920.043
H63'0.621070.113660.621170.042
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.01187 (2)0.01929 (3)0.01616 (2)0.00406 (2)0.00274 (2)0.00702 (2)
O0.01106 (7)0.0518 (3)0.02027 (10)0.00620 (9)0.00499 (6)0.01159 (12)
N10.01004 (5)0.01874 (8)0.01291 (6)0.00200 (5)0.00315 (4)0.00531 (5)
N30.01207 (6)0.01825 (8)0.01465 (6)0.00390 (5)0.00479 (5)0.00720 (6)
C20.01102 (6)0.01442 (7)0.01278 (6)0.00253 (5)0.00300 (5)0.00398 (5)
C40.01087 (6)0.01736 (8)0.01275 (6)0.00261 (5)0.00364 (5)0.00484 (6)
C4'0.01814 (9)0.01736 (9)0.01559 (8)0.00455 (7)0.00510 (7)0.00468 (7)
C4"0.02284 (12)0.02143 (11)0.01429 (8)0.00252 (9)0.00477 (8)0.00181 (8)
C50.01022 (6)0.01898 (8)0.01221 (6)0.00242 (5)0.00284 (5)0.00466 (6)
C5'0.01054 (7)0.02415 (11)0.01441 (8)0.00249 (6)0.00222 (6)0.00576 (7)
C5"0.01592 (10)0.03289 (17)0.01424 (8)0.00570 (10)0.00064 (7)0.00434 (9)
C60.01052 (6)0.01677 (8)0.01130 (6)0.00169 (5)0.00289 (5)0.00370 (5)
C6'0.01517 (8)0.02387 (11)0.01220 (7)0.00151 (7)0.00417 (6)0.00473 (7)
(II) top
Crystal data top
C8H12N2O2F(000) = 720
Mr = 168.20Dx = 1.355 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 14.2785 (1) ÅCell parameters from 9999 reflections
b = 6.9187 (1) Åθ = 2.4–51.5°
c = 17.1827 (2) ŵ = 0.10 mm1
β = 103.642 (1)°T = 110 K
V = 1649.56 (1) Å3Prism, colorless
Z = 80.42 × 0.34 × 0.22 mm
Data collection top
Bruker
diffractometer with a SMART 6000 CCD detector
Rint = 0.048
Graphite monochromatorθmax = 51.5°, θmin = 2.4°
ω scansh = 029
46839 measured reflectionsk = 015
8718 independent reflectionsl = 3736
7330 reflections with I > 2σ(I)
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: difference Fourier map
wR(F2) = 0.116All H-atom parameters refined
S = 1.08 w = 1/[σ2(Fo2) + (0.0787P)2]
where P = (Fo2 + 2Fc2)/3
8718 reflections(Δ/σ)max = 0.001
157 parametersΔρmax = 0.81 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C8H12N2O2V = 1649.56 (1) Å3
Mr = 168.20Z = 8
Monoclinic, C2/cMo Kα radiation
a = 14.2785 (1) ŵ = 0.10 mm1
b = 6.9187 (1) ÅT = 110 K
c = 17.1827 (2) Å0.42 × 0.34 × 0.22 mm
β = 103.642 (1)°
Data collection top
Bruker
diffractometer with a SMART 6000 CCD detector
7330 reflections with I > 2σ(I)
46839 measured reflectionsRint = 0.048
8718 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.116All H-atom parameters refined
S = 1.08Δρmax = 0.81 e Å3
8718 reflectionsΔρmin = 0.25 e Å3
157 parameters
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.31998 (2)0.72688 (4)0.427659 (15)0.01857 (5)
O20.11751 (2)0.01312 (4)0.278433 (17)0.02043 (5)
N10.19285 (2)0.53867 (4)0.440001 (15)0.01468 (4)
N30.272344 (18)0.47801 (4)0.340460 (14)0.01372 (4)
C20.26456 (2)0.59029 (4)0.402018 (15)0.01342 (4)
C40.19485 (2)0.34889 (4)0.299860 (15)0.01320 (4)
C4'0.12283 (3)0.45513 (5)0.233209 (19)0.01869 (5)
C50.14602 (2)0.25923 (4)0.360596 (16)0.01279 (4)
C5'0.10425 (2)0.06699 (4)0.339243 (17)0.01410 (4)
C5"0.04508 (3)0.03817 (5)0.38795 (2)0.01790 (5)
C60.14326 (2)0.36476 (4)0.427177 (15)0.01277 (4)
C6'0.09215 (2)0.31871 (5)0.492226 (18)0.01685 (5)
H10.1881 (6)0.6101 (13)0.4794 (5)0.0277 (19)*
H30.3178 (7)0.5094 (13)0.3103 (6)0.033 (2)*
H40.2272 (6)0.2468 (12)0.2744 (5)0.0216 (17)*
H41'0.1564 (7)0.5016 (12)0.1901 (5)0.0275 (19)*
H42'0.0703 (7)0.3669 (13)0.2076 (6)0.034 (2)*
H43'0.0951 (7)0.5628 (13)0.2548 (6)0.0283 (19)*
H51"0.0187 (7)0.1557 (13)0.3579 (6)0.034 (2)*
H52"0.0841 (7)0.0625 (14)0.4437 (5)0.032 (2)*
H53"0.0089 (6)0.0475 (12)0.3969 (5)0.0229 (18)*
H61'0.1189 (7)0.2005 (14)0.5217 (5)0.034 (2)*
H62'0.0979 (7)0.4359 (15)0.5300 (6)0.036 (2)*
H63'0.0242 (7)0.3088 (14)0.4690 (6)0.035 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.02115 (10)0.01990 (10)0.01561 (8)0.00738 (7)0.00625 (7)0.00466 (7)
O20.02474 (11)0.01969 (10)0.02038 (10)0.00641 (8)0.01239 (8)0.00705 (8)
N10.01733 (9)0.01469 (9)0.01370 (8)0.00178 (6)0.00702 (6)0.00235 (6)
N30.01381 (8)0.01625 (9)0.01208 (7)0.00214 (6)0.00500 (6)0.00176 (6)
C20.01452 (9)0.01469 (9)0.01130 (8)0.00130 (6)0.00359 (6)0.00053 (7)
C40.01480 (9)0.01425 (9)0.01161 (8)0.00169 (6)0.00523 (6)0.00161 (7)
C4'0.01891 (12)0.02324 (13)0.01291 (9)0.00327 (9)0.00173 (8)0.00177 (8)
C50.01396 (9)0.01336 (9)0.01202 (8)0.00062 (6)0.00501 (6)0.00046 (6)
C5'0.01461 (9)0.01457 (9)0.01403 (9)0.00124 (7)0.00523 (7)0.00082 (7)
C5"0.02060 (12)0.01768 (11)0.01691 (10)0.00430 (8)0.00742 (8)0.00061 (8)
C60.01362 (9)0.01391 (9)0.01158 (8)0.00046 (6)0.00461 (6)0.00014 (6)
C6'0.01978 (12)0.01864 (11)0.01456 (9)0.00031 (8)0.00889 (8)0.00024 (8)
Geometric parameters (Å, º) top
O1—C21.2446 (4)C4'—H42'0.986 (9)
O2—C5'1.2361 (4)C4'—H43'0.958 (9)
N1—C21.3845 (4)C5—C61.3656 (4)
N1—C61.3872 (4)C5—C5'1.4684 (4)
N1—H10.853 (9)C5'—C5"1.5091 (4)
N3—C21.3379 (4)C5"—H51"0.989 (9)
N3—C41.4645 (4)C5"—H52"1.002 (9)
N3—H30.946 (10)C5"—H53"1.012 (8)
C4—C51.5177 (4)C6—C6'1.5060 (4)
C4—C4'1.5342 (4)C6'—H61'0.990 (9)
C4—H41.000 (8)C6'—H62'1.030 (10)
C4'—H41'1.024 (9)C6'—H63'0.960 (10)
C2—N1—C6123.74 (2)C6—C5—C5'127.11 (2)
C2—N1—H1115.5 (6)C6—C5—C4117.79 (2)
C6—N1—H1119.7 (6)C5'—C5—C4115.07 (2)
C2—N3—C4122.44 (2)O2—C5'—C5118.90 (3)
C2—N3—H3119.7 (6)O2—C5'—C5"118.04 (3)
C4—N3—H3114.7 (6)C5—C5'—C5"123.07 (2)
O1—C2—N3123.80 (3)C5'—C5"—H51"107.5 (5)
O1—C2—N1120.54 (3)C5'—C5"—H52"110.7 (5)
N3—C2—N1115.56 (3)H51"—C5"—H52"114.7 (8)
N3—C4—C5109.86 (2)C5'—C5"—H53"110.3 (5)
N3—C4—C4'111.19 (2)H51"—C5"—H53"110.6 (7)
C5—C4—C4'111.92 (2)H52"—C5"—H53"103.1 (7)
N3—C4—H4105.3 (5)C5—C6—N1118.84 (2)
C5—C4—H4110.3 (5)C5—C6—C6'128.57 (3)
C4'—C4—H4108.1 (5)N1—C6—C6'112.59 (2)
C4—C4'—H41'110.2 (5)C6—C6'—H61'111.0 (5)
C4—C4'—H42'109.9 (5)C6—C6'—H62'108.7 (6)
H41'—C4'—H42'107.9 (7)H61'—C6'—H62'111.3 (8)
C4—C4'—H43'110.4 (6)C6—C6'—H63'109.0 (6)
H41'—C4'—H43'110.0 (7)H61'—C6'—H63'112.6 (8)
H42'—C4'—H43'108.3 (8)H62'—C6'—H63'103.9 (8)
(IImult) top
Crystal data top
?β = ?°
Mr = ?γ = ?°
?, ?V = ? Å3
a = ? ÅZ = ?
b = ? Å? radiation, λ = ? Å
c = ? Å × × mm
α = ?°
Data collection top
h = ??l = ??
k = ??
Refinement top
Refinement on F6921 reflections
Least-squares matrix: full228 parameters
R[F2 > 2σ(F2)] = 0.0190 restraints
wR(F2) = 0.022 ' w = 1/[σ2(Fo2) + (0.00015)2]
S = 1.07
Crystal data top
?β = ?°
Mr = ?γ = ?°
?, ?V = ? Å3
a = ? ÅZ = ?
b = ? Å? radiation, λ = ? Å
c = ? Å × × mm
α = ?°
Data collection top
Refinement top
R[F2 > 2σ(F2)] = 0.0196921 reflections
wR(F2) = 0.022228 parameters
S = 1.070 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.32001 (2)0.72664 (4)0.42766 (1)0.019
O20.11744 (2)0.01319 (4)0.27846 (1)0.022
N10.19289 (2)0.53861 (3)0.44001 (1)0.015
N30.27227 (1)0.47811 (3)0.34040 (1)0.014
C20.26452 (2)0.59020 (4)0.40198 (1)0.014
C40.19490 (2)0.34905 (4)0.29991 (1)0.013
C4'0.12286 (2)0.45506 (5)0.23320 (1)0.018
C50.14605 (2)0.25924 (3)0.36061 (1)0.013
C5'0.10429 (2)0.06699 (4)0.33928 (1)0.014
C5"0.04502 (2)0.03810 (4)0.38796 (2)0.018
C60.14326 (2)0.36489 (3)0.42720 (1)0.013
C6'0.09221 (2)0.31865 (4)0.49226 (1)0.018
H10.187170.623020.486570.025
H30.324110.512710.311780.024
H40.229300.234970.272490.029
H41'0.158660.499640.188910.043
H42'0.065370.362760.205940.039
H43'0.095540.577660.257320.043
H51"0.019850.168090.357730.047
H52"0.086490.078600.445110.044
H53"0.014750.045420.394400.038
H61'0.120430.190800.522690.049
H62'0.102720.433300.534180.049
H63'0.016900.303310.469980.043
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.02112 (8)0.01998 (8)0.01524 (5)0.00748 (6)0.00650 (5)0.00485 (5)
O20.02535 (9)0.01968 (8)0.02022 (7)0.00709 (6)0.01297 (7)0.00739 (6)
N10.01743 (7)0.01472 (7)0.01338 (5)0.00191 (5)0.00702 (5)0.00250 (5)
N30.01374 (6)0.01627 (7)0.01178 (5)0.00230 (4)0.00497 (4)0.00174 (5)
C20.01466 (7)0.01466 (7)0.01121 (5)0.00178 (5)0.00377 (5)0.00103 (5)
C40.01464 (7)0.01432 (7)0.01145 (5)0.00155 (5)0.00519 (5)0.00152 (5)
C4'0.01877 (8)0.02333 (10)0.01287 (6)0.00322 (7)0.00166 (6)0.00193 (6)
C50.01422 (7)0.01340 (7)0.01178 (5)0.00078 (5)0.00516 (5)0.00065 (5)
C5'0.01509 (7)0.01429 (7)0.01393 (6)0.00166 (5)0.00577 (5)0.00122 (5)
C5"0.02068 (9)0.01773 (9)0.01675 (7)0.00433 (6)0.00740 (6)0.00054 (6)
C60.01379 (6)0.01381 (7)0.01128 (5)0.00019 (5)0.00490 (4)0.00012 (5)
C6'0.01956 (9)0.01876 (9)0.01448 (6)0.00048 (6)0.00880 (6)0.00021 (6)

Experimental details

(I)(Imult)(II)(IImult)
Crystal data
Chemical formulaC9H14N2OS?C8H12N2O2?
Mr198.28?168.20?
Crystal system, space groupTriclinic, P1?, ?Monoclinic, C2/c?, ?
Temperature (K)110?110?
a, b, c (Å)7.2533 (2), 7.8212 (3), 9.1837 (3)?, ?, ?14.2785 (1), 6.9187 (1), 17.1827 (2)?, ?, ?
α, β, γ (°)97.187 (1), 100.674 (1), 94.106 (1)?, ?, ?90, 103.642 (1), 90?, ?, ?
V3)505.54 (2)?1649.56 (1)?
Z2?8?
Radiation typeMo Kα?, λ = ? ÅMo Kα?, λ = ? Å
µ (mm1)0.28?0.10?
Crystal size (mm)0.40 × 0.22 × 0.14 × × 0.42 × 0.34 × 0.22 × ×
Data collection
DiffractometerBruker
diffractometer with a SMART 6000 CCD detector
?Bruker
diffractometer with a SMART 6000 CCD detector
?
Absorption correctionMulti-scan
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
??
Tmin, Tmax0.909, 1.106?, ??, ?
No. of measured, independent and
observed reflections
57560, 12868, 10974 [I > 2σ(I)]?, ?, ? (?)46839, 8718, 7330 [I > 2σ(I)]?, ?, ? (?)
Rint0.042?0.048?
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.092, 1.08 0.019, 0.030, 1.43 0.037, 0.116, 1.08 0.019, 0.022, 1.07
No. of reflections128681041887186921
No. of parameters174275157228
H-atom treatmentAll H-atom parameters refinedAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.81, 0.58?, ?0.81, 0.25?, ?

Computer programs: CrystalClear,(2005), Otwinowski & Minor (1997), SORTAV (Blessing, 1987, 1989,1995), SORTAV (Blessing, 1987,1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Protas, J. (1997). MOLDOS97/MOLLY IBM PC-DOS.

 

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