organic compounds
5-tert-Butyl 3-ethyl 1-isopropyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine-3,5-dicarboxylate
aMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
*Correspondence e-mail: huanmeiguo@163.com
In the title compound, C17H27N3O4, the six-membered ring adopts a half-chair conformation with the N atom and the adjacent methylene C atom displaced by −0.391 (2) and 0.358 (2) Å, respectively, from the plane of the other four atoms. In the crystal, molecules are linked by weak C—H⋯O interactions.
Related literature
For a related structure and background references to heterocycles as pharmaceuticals, see: Guo (2011).
Experimental
Crystal data
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Refinement
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Data collection: CrystalClear (Rigaku, 2007); cell CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
https://doi.org/10.1107/S1600536811046332/hb6476sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046332/hb6476Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536811046332/hb6476Isup3.cml
The title compound was synthesized with 5-tert-butyl 3-ethyl 6,7-dihydro-1H- pyrazolo[4,3-c]pyridine-3,5(4H)- dicarboxylate (1 eq), NaH (2.5 eq) and 2-bromopropane (1.2 eq) in THF at 273 K to room temperature. Single crystals of the compound suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.
All H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances in the range 0.98–1.00 Å, and with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(Cmethyl).
As part of our ongoing studies of heterocycles (Guo, 2011), herein we report the structure of the title compound.
In the molecule (Fig. 1), all bond lengths and angles are within normal ranges.The atoms N1, N2, C1, C2, C3, C4 and C6 lie in a plan(p1), with a maximum deviation of 0.0100 (15)Å; atoms N3, C13, O3, O4, and C14 lie in a plan(p2) too, the maximum deviation is 0.0552 (12)Å. The dihedral angle between p1 and p2 is 75.44 (5)°.
For a related structure and background references to heterocycles as pharmaceuticals, see: Guo (2011).
Data collection: CrystalClear (Rigaku, 2007); cell
CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. |
C17H27N3O4 | F(000) = 728 |
Mr = 337.42 | Dx = 1.252 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5928 reflections |
a = 13.017 (3) Å | θ = 1.6–27.5° |
b = 12.771 (3) Å | µ = 0.09 mm−1 |
c = 11.952 (3) Å | T = 173 K |
β = 115.760 (3)° | Block, colorless |
V = 1789.4 (7) Å3 | 0.21 × 0.17 × 0.06 mm |
Z = 4 |
Rigaku MM007-HF CCD (Saturn 724+) diffractometer | 4013 independent reflections |
Radiation source: rotating anode | 3330 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.039 |
ω scans at fixed χ = 45° | θmax = 27.4°, θmin = 1.7° |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007) | h = −16→14 |
Tmin = 0.981, Tmax = 0.995 | k = −16→15 |
7844 measured reflections | l = −8→15 |
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) = 0.128 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0346P)2 + 1.0152P] where P = (Fo2 + 2Fc2)/3 |
4013 reflections | (Δ/σ)max = 0.001 |
223 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C17H27N3O4 | V = 1789.4 (7) Å3 |
Mr = 337.42 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.017 (3) Å | µ = 0.09 mm−1 |
b = 12.771 (3) Å | T = 173 K |
c = 11.952 (3) Å | 0.21 × 0.17 × 0.06 mm |
β = 115.760 (3)° |
Rigaku MM007-HF CCD (Saturn 724+) diffractometer | 4013 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007) | 3330 reflections with I > 2σ(I) |
Tmin = 0.981, Tmax = 0.995 | Rint = 0.039 |
7844 measured reflections |
R[F2 > 2σ(F2)] = 0.060 | 0 restraints |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.27 e Å−3 |
4013 reflections | Δρmin = −0.22 e Å−3 |
223 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.89479 (12) | 0.21624 (10) | 0.88381 (12) | 0.0305 (3) | |
O2 | 0.83497 (11) | 0.09119 (10) | 0.73679 (11) | 0.0270 (3) | |
O3 | 0.59568 (12) | −0.19414 (12) | 0.66795 (13) | 0.0379 (4) | |
O4 | 0.62019 (11) | −0.32250 (10) | 0.80972 (12) | 0.0272 (3) | |
N1 | 0.86219 (13) | −0.02179 (11) | 1.09856 (13) | 0.0214 (3) | |
N2 | 0.87328 (12) | 0.06944 (11) | 1.04856 (13) | 0.0208 (3) | |
N3 | 0.77214 (13) | −0.23478 (12) | 0.81927 (14) | 0.0231 (3) | |
C1 | 0.86041 (14) | 0.04334 (13) | 0.93459 (16) | 0.0191 (4) | |
C2 | 0.83954 (14) | −0.06483 (14) | 0.91134 (16) | 0.0194 (4) | |
C3 | 0.84147 (14) | −0.10378 (14) | 1.01911 (16) | 0.0202 (4) | |
C4 | 0.82646 (16) | −0.21603 (14) | 1.04464 (17) | 0.0236 (4) | |
H4A | 0.7507 | −0.2267 | 1.0436 | 0.028* | |
H4B | 0.8859 | −0.2369 | 1.1272 | 0.028* | |
C5 | 0.83677 (16) | −0.28141 (14) | 0.94246 (17) | 0.0241 (4) | |
H5B | 0.9181 | −0.2869 | 0.9595 | 0.029* | |
H5A | 0.8080 | −0.3530 | 0.9433 | 0.029* | |
C6 | 0.82002 (16) | −0.13484 (14) | 0.80231 (17) | 0.0245 (4) | |
H6A | 0.7665 | −0.1010 | 0.7241 | 0.029* | |
H6B | 0.8930 | −0.1474 | 0.7974 | 0.029* | |
C7 | 0.86696 (14) | 0.12674 (14) | 0.85268 (16) | 0.0206 (4) | |
C8 | 0.83558 (18) | 0.16686 (16) | 0.64603 (17) | 0.0307 (4) | |
H8B | 0.9146 | 0.1795 | 0.6575 | 0.037* | |
H8A | 0.8028 | 0.2342 | 0.6559 | 0.037* | |
C9 | 0.7652 (2) | 0.12184 (19) | 0.51993 (18) | 0.0409 (5) | |
H9B | 0.7695 | 0.1678 | 0.4565 | 0.061* | |
H9A | 0.6856 | 0.1159 | 0.5067 | 0.061* | |
H9C | 0.7943 | 0.0523 | 0.5141 | 0.061* | |
C10 | 0.85336 (16) | −0.02244 (14) | 1.21705 (16) | 0.0241 (4) | |
H10 | 0.8639 | −0.0962 | 1.2482 | 0.029* | |
C11 | 0.94661 (17) | 0.04410 (16) | 1.31347 (17) | 0.0298 (4) | |
H11B | 1.0211 | 0.0209 | 1.3211 | 0.045* | |
H11C | 0.9441 | 0.0366 | 1.3939 | 0.045* | |
H11A | 0.9348 | 0.1177 | 1.2877 | 0.045* | |
C12 | 0.73472 (17) | 0.01270 (18) | 1.19462 (19) | 0.0365 (5) | |
H12B | 0.7229 | 0.0853 | 1.1652 | 0.055* | |
H12C | 0.7267 | 0.0079 | 1.2723 | 0.055* | |
H12A | 0.6779 | −0.0324 | 1.1318 | 0.055* | |
C13 | 0.65564 (16) | −0.24563 (15) | 0.75820 (17) | 0.0246 (4) | |
C14 | 0.49694 (16) | −0.34246 (16) | 0.76793 (18) | 0.0293 (4) | |
C15 | 0.49744 (19) | −0.43108 (18) | 0.8521 (2) | 0.0433 (6) | |
H15A | 0.4187 | −0.4506 | 0.8330 | 0.065* | |
H15C | 0.5368 | −0.4085 | 0.9389 | 0.065* | |
H15B | 0.5371 | −0.4916 | 0.8389 | 0.065* | |
C16 | 0.44174 (18) | −0.3756 (2) | 0.6327 (2) | 0.0434 (6) | |
H16B | 0.3628 | −0.3971 | 0.6094 | 0.065* | |
H16C | 0.4843 | −0.4345 | 0.6207 | 0.065* | |
H16A | 0.4425 | −0.3167 | 0.5805 | 0.065* | |
C17 | 0.44277 (19) | −0.24554 (19) | 0.7929 (2) | 0.0410 (5) | |
H17A | 0.4487 | −0.1872 | 0.7428 | 0.062* | |
H17C | 0.4823 | −0.2273 | 0.8811 | 0.062* | |
H17B | 0.3622 | −0.2595 | 0.7708 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0424 (8) | 0.0206 (7) | 0.0280 (7) | −0.0067 (6) | 0.0148 (6) | −0.0004 (5) |
O2 | 0.0420 (8) | 0.0206 (7) | 0.0205 (6) | −0.0026 (6) | 0.0154 (6) | 0.0015 (5) |
O3 | 0.0346 (8) | 0.0423 (9) | 0.0303 (8) | −0.0006 (7) | 0.0079 (7) | 0.0120 (7) |
O4 | 0.0233 (7) | 0.0266 (7) | 0.0301 (7) | −0.0030 (5) | 0.0099 (6) | 0.0028 (6) |
N1 | 0.0283 (8) | 0.0172 (7) | 0.0201 (7) | −0.0012 (6) | 0.0119 (7) | 0.0001 (6) |
N2 | 0.0246 (8) | 0.0177 (7) | 0.0211 (7) | −0.0008 (6) | 0.0108 (6) | 0.0007 (6) |
N3 | 0.0275 (8) | 0.0192 (7) | 0.0226 (8) | −0.0042 (6) | 0.0110 (7) | −0.0027 (6) |
C1 | 0.0179 (8) | 0.0192 (9) | 0.0202 (8) | −0.0008 (7) | 0.0085 (7) | 0.0001 (7) |
C2 | 0.0199 (8) | 0.0194 (9) | 0.0198 (8) | −0.0022 (7) | 0.0094 (7) | −0.0015 (7) |
C3 | 0.0215 (9) | 0.0183 (9) | 0.0209 (8) | −0.0013 (7) | 0.0092 (7) | −0.0012 (7) |
C4 | 0.0294 (10) | 0.0199 (9) | 0.0219 (9) | −0.0032 (8) | 0.0114 (8) | 0.0010 (7) |
C5 | 0.0263 (9) | 0.0193 (9) | 0.0248 (9) | −0.0005 (7) | 0.0093 (8) | −0.0005 (7) |
C6 | 0.0340 (10) | 0.0205 (9) | 0.0233 (9) | −0.0065 (8) | 0.0164 (8) | −0.0037 (7) |
C7 | 0.0191 (8) | 0.0204 (9) | 0.0225 (9) | 0.0005 (7) | 0.0093 (7) | 0.0022 (7) |
C8 | 0.0410 (12) | 0.0279 (10) | 0.0263 (10) | −0.0007 (9) | 0.0176 (9) | 0.0068 (8) |
C9 | 0.0554 (14) | 0.0414 (13) | 0.0237 (10) | −0.0036 (11) | 0.0152 (10) | 0.0064 (9) |
C10 | 0.0354 (10) | 0.0223 (9) | 0.0177 (8) | 0.0003 (8) | 0.0143 (8) | 0.0017 (7) |
C11 | 0.0368 (11) | 0.0302 (11) | 0.0210 (9) | 0.0016 (9) | 0.0113 (9) | −0.0022 (8) |
C12 | 0.0343 (11) | 0.0490 (13) | 0.0320 (11) | −0.0023 (10) | 0.0198 (9) | 0.0007 (10) |
C13 | 0.0285 (10) | 0.0229 (9) | 0.0231 (9) | −0.0023 (8) | 0.0118 (8) | −0.0022 (8) |
C14 | 0.0223 (9) | 0.0337 (11) | 0.0321 (10) | −0.0019 (8) | 0.0121 (8) | −0.0006 (9) |
C15 | 0.0356 (12) | 0.0398 (13) | 0.0555 (15) | −0.0079 (10) | 0.0207 (11) | 0.0071 (11) |
C16 | 0.0289 (11) | 0.0602 (16) | 0.0395 (12) | −0.0135 (11) | 0.0133 (10) | −0.0149 (11) |
C17 | 0.0385 (12) | 0.0445 (13) | 0.0453 (13) | 0.0071 (10) | 0.0231 (11) | −0.0003 (11) |
O1—C7 | 1.208 (2) | C8—H8B | 0.9900 |
O2—C7 | 1.340 (2) | C8—H8A | 0.9900 |
O2—C8 | 1.455 (2) | C9—H9B | 0.9800 |
O3—C13 | 1.214 (2) | C9—H9A | 0.9800 |
O4—C13 | 1.343 (2) | C9—H9C | 0.9800 |
O4—C14 | 1.480 (2) | C10—C12 | 1.516 (3) |
N1—N2 | 1.345 (2) | C10—C11 | 1.519 (3) |
N1—C3 | 1.360 (2) | C10—H10 | 1.0000 |
N1—C10 | 1.470 (2) | C11—H11B | 0.9800 |
N2—C1 | 1.340 (2) | C11—H11C | 0.9800 |
N3—C13 | 1.375 (2) | C11—H11A | 0.9800 |
N3—C5 | 1.468 (2) | C12—H12B | 0.9800 |
N3—C6 | 1.472 (2) | C12—H12C | 0.9800 |
C1—C2 | 1.412 (2) | C12—H12A | 0.9800 |
C1—C7 | 1.474 (2) | C14—C15 | 1.512 (3) |
C2—C3 | 1.371 (2) | C14—C16 | 1.516 (3) |
C2—C6 | 1.508 (2) | C14—C17 | 1.517 (3) |
C3—C4 | 1.496 (2) | C15—H15A | 0.9800 |
C4—C5 | 1.533 (2) | C15—H15C | 0.9800 |
C4—H4A | 0.9900 | C15—H15B | 0.9800 |
C4—H4B | 0.9900 | C16—H16B | 0.9800 |
C5—H5B | 0.9900 | C16—H16C | 0.9800 |
C5—H5A | 0.9900 | C16—H16A | 0.9800 |
C6—H6A | 0.9900 | C17—H17A | 0.9800 |
C6—H6B | 0.9900 | C17—H17C | 0.9800 |
C8—C9 | 1.497 (3) | C17—H17B | 0.9800 |
C7—O2—C8 | 116.44 (14) | C8—C9—H9C | 109.5 |
C13—O4—C14 | 120.61 (14) | H9B—C9—H9C | 109.5 |
N2—N1—C3 | 112.56 (14) | H9A—C9—H9C | 109.5 |
N2—N1—C10 | 120.08 (14) | N1—C10—C12 | 109.16 (15) |
C3—N1—C10 | 126.43 (15) | N1—C10—C11 | 110.89 (15) |
C1—N2—N1 | 104.24 (14) | C12—C10—C11 | 112.66 (17) |
C13—N3—C5 | 120.72 (15) | N1—C10—H10 | 108.0 |
C13—N3—C6 | 116.71 (15) | C12—C10—H10 | 108.0 |
C5—N3—C6 | 113.42 (14) | C11—C10—H10 | 108.0 |
N2—C1—C2 | 111.82 (15) | C10—C11—H11B | 109.5 |
N2—C1—C7 | 118.53 (15) | C10—C11—H11C | 109.5 |
C2—C1—C7 | 129.64 (16) | H11B—C11—H11C | 109.5 |
C3—C2—C1 | 104.29 (15) | C10—C11—H11A | 109.5 |
C3—C2—C6 | 121.62 (16) | H11B—C11—H11A | 109.5 |
C1—C2—C6 | 134.09 (16) | H11C—C11—H11A | 109.5 |
N1—C3—C2 | 107.09 (15) | C10—C12—H12B | 109.5 |
N1—C3—C4 | 126.83 (15) | C10—C12—H12C | 109.5 |
C2—C3—C4 | 126.07 (16) | H12B—C12—H12C | 109.5 |
C3—C4—C5 | 107.16 (14) | C10—C12—H12A | 109.5 |
C3—C4—H4A | 110.3 | H12B—C12—H12A | 109.5 |
C5—C4—H4A | 110.3 | H12C—C12—H12A | 109.5 |
C3—C4—H4B | 110.3 | O3—C13—O4 | 125.96 (18) |
C5—C4—H4B | 110.3 | O3—C13—N3 | 123.52 (17) |
H4A—C4—H4B | 108.5 | O4—C13—N3 | 110.48 (15) |
N3—C5—C4 | 111.58 (15) | O4—C14—C15 | 102.34 (15) |
N3—C5—H5B | 109.3 | O4—C14—C16 | 110.48 (15) |
C4—C5—H5B | 109.3 | C15—C14—C16 | 111.31 (19) |
N3—C5—H5A | 109.3 | O4—C14—C17 | 108.74 (16) |
C4—C5—H5A | 109.3 | C15—C14—C17 | 110.36 (18) |
H5B—C5—H5A | 108.0 | C16—C14—C17 | 113.07 (18) |
N3—C6—C2 | 108.50 (14) | C14—C15—H15A | 109.5 |
N3—C6—H6A | 110.0 | C14—C15—H15C | 109.5 |
C2—C6—H6A | 110.0 | H15A—C15—H15C | 109.5 |
N3—C6—H6B | 110.0 | C14—C15—H15B | 109.5 |
C2—C6—H6B | 110.0 | H15A—C15—H15B | 109.5 |
H6A—C6—H6B | 108.4 | H15C—C15—H15B | 109.5 |
O1—C7—O2 | 123.77 (16) | C14—C16—H16B | 109.5 |
O1—C7—C1 | 125.12 (17) | C14—C16—H16C | 109.5 |
O2—C7—C1 | 111.09 (15) | H16B—C16—H16C | 109.5 |
O2—C8—C9 | 107.22 (16) | C14—C16—H16A | 109.5 |
O2—C8—H8B | 110.3 | H16B—C16—H16A | 109.5 |
C9—C8—H8B | 110.3 | H16C—C16—H16A | 109.5 |
O2—C8—H8A | 110.3 | C14—C17—H17A | 109.5 |
C9—C8—H8A | 110.3 | C14—C17—H17C | 109.5 |
H8B—C8—H8A | 108.5 | H17A—C17—H17C | 109.5 |
C8—C9—H9B | 109.5 | C14—C17—H17B | 109.5 |
C8—C9—H9A | 109.5 | H17A—C17—H17B | 109.5 |
H9B—C9—H9A | 109.5 | H17C—C17—H17B | 109.5 |
C3—N1—N2—C1 | −0.73 (19) | C3—C2—C6—N3 | 16.5 (2) |
C10—N1—N2—C1 | −170.41 (15) | C1—C2—C6—N3 | −164.66 (18) |
N1—N2—C1—C2 | 0.77 (19) | C8—O2—C7—O1 | 0.4 (3) |
N1—N2—C1—C7 | 179.55 (14) | C8—O2—C7—C1 | 178.84 (15) |
N2—C1—C2—C3 | −0.5 (2) | N2—C1—C7—O1 | 8.1 (3) |
C7—C1—C2—C3 | −179.14 (17) | C2—C1—C7—O1 | −173.39 (18) |
N2—C1—C2—C6 | −179.51 (18) | N2—C1—C7—O2 | −170.33 (15) |
C7—C1—C2—C6 | 1.9 (3) | C2—C1—C7—O2 | 8.2 (3) |
N2—N1—C3—C2 | 0.4 (2) | C7—O2—C8—C9 | −163.00 (16) |
C10—N1—C3—C2 | 169.31 (16) | N2—N1—C10—C12 | 75.7 (2) |
N2—N1—C3—C4 | 179.00 (16) | C3—N1—C10—C12 | −92.4 (2) |
C10—N1—C3—C4 | −12.1 (3) | N2—N1—C10—C11 | −49.0 (2) |
C1—C2—C3—N1 | 0.07 (18) | C3—N1—C10—C11 | 142.90 (17) |
C6—C2—C3—N1 | 179.20 (15) | C14—O4—C13—O3 | −8.2 (3) |
C1—C2—C3—C4 | −178.52 (17) | C14—O4—C13—N3 | 174.12 (15) |
C6—C2—C3—C4 | 0.6 (3) | C5—N3—C13—O3 | 166.25 (18) |
N1—C3—C4—C5 | −165.31 (16) | C6—N3—C13—O3 | 21.5 (3) |
C2—C3—C4—C5 | 13.0 (2) | C5—N3—C13—O4 | −16.0 (2) |
C13—N3—C5—C4 | −77.8 (2) | C6—N3—C13—O4 | −160.74 (14) |
C6—N3—C5—C4 | 67.98 (19) | C13—O4—C14—C15 | −178.30 (17) |
C3—C4—C5—N3 | −44.5 (2) | C13—O4—C14—C16 | 63.1 (2) |
C13—N3—C6—C2 | 97.36 (18) | C13—O4—C14—C17 | −61.5 (2) |
C5—N3—C6—C2 | −49.90 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5B···O1i | 0.99 | 2.51 | 3.303 (3) | 137 |
C11—H11A···O1ii | 0.98 | 2.57 | 3.320 (3) | 133 |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C17H27N3O4 |
Mr | 337.42 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 173 |
a, b, c (Å) | 13.017 (3), 12.771 (3), 11.952 (3) |
β (°) | 115.760 (3) |
V (Å3) | 1789.4 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.21 × 0.17 × 0.06 |
Data collection | |
Diffractometer | Rigaku MM007-HF CCD (Saturn 724+) |
Absorption correction | Multi-scan (CrystalClear; Rigaku, 2007) |
Tmin, Tmax | 0.981, 0.995 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7844, 4013, 3330 |
Rint | 0.039 |
(sin θ/λ)max (Å−1) | 0.648 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.128, 1.09 |
No. of reflections | 4013 |
No. of parameters | 223 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.22 |
Computer programs: CrystalClear (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5B···O1i | 0.99 | 2.51 | 3.303 (3) | 137 |
C11—H11A···O1ii | 0.98 | 2.57 | 3.320 (3) | 133 |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) x, −y+1/2, z+1/2. |
Acknowledgements
The author would like to thank Shandong Provincial Natural Science Foundation, China (Y2008B29) and Yuandu Scholar of Weifang City.
References
Guo, H.-M. (2011). Acta Cryst. E67, o2516. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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As part of our ongoing studies of heterocycles (Guo, 2011), herein we report the structure of the title compound.
In the molecule (Fig. 1), all bond lengths and angles are within normal ranges.The atoms N1, N2, C1, C2, C3, C4 and C6 lie in a plan(p1), with a maximum deviation of 0.0100 (15)Å; atoms N3, C13, O3, O4, and C14 lie in a plan(p2) too, the maximum deviation is 0.0552 (12)Å. The dihedral angle between p1 and p2 is 75.44 (5)°.