2-Ethoxy-3-(4-fluorophenyl)-4-oxo-5-phenyl-3,4-dihydro-5H-pyrrolo[3,2-d]pyrimidine-7-carbonitrile
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060187/at2469sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060187/at2469Isup2.hkl |
CCDC reference: 673073
To a solution of the ethyl 3-((4-fluorophenylimino)methyleneamino)- 4-cyano-1-phenyl-1H-pyrrole-2-carboxylate (II) (3 mmol) in dichloromethane (5 ml) was added sodium ethoxide(3 mmol)/ethanol (5 ml). After stirring the reaction mixture for 4 h, the solvent was removed under reduced pressure and the residue was recrystallized from ethanol to give the title compound, in a yield of 83%. Suitable crystals were obtained by vapour diffusion of ethanol into dichloromethane at room temperature.
All H-atoms were positioned geometrically and refined using a riding model with C—H = 0.93 Å, Uiso=1.2Ueq (C) for Csp2, C—H = 0.97 Å, Uiso = 1.2Ueq (C) for CH2, C—H = 0.96 Å, Uiso = 1.5Ueq (C) for CH3. The relative occupancies for the disordered components were refined anisotropically to yield relative occupancies of 0.65 (2) and 0.35 (2), respectively, for C20, C21 and C20', C21'. The H atoms of these disorder atoms were located geometrically and refined using a riding model.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).
C21H15FN4O2 | F(000) = 776 |
Mr = 374.37 | Dx = 1.322 Mg m−3 |
Monoclinic, P21/c | Melting point: 543.0 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 10.7513 (5) Å | Cell parameters from 2131 reflections |
b = 13.2684 (7) Å | θ = 2.2–21.9° |
c = 13.2210 (7) Å | µ = 0.10 mm−1 |
β = 93.890 (1)° | T = 273 K |
V = 1881.66 (17) Å3 | Block, colourless |
Z = 4 | 0.20 × 0.10 × 0.10 mm |
Bruker SMART 4K CCD area-detector diffractometer | 4099 independent reflections |
Radiation source: fine-focus sealed tube | 2039 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.087 |
ϕ and ω scans | θmax = 27.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −13→13 |
Tmin = 0.981, Tmax = 0.991 | k = −16→16 |
20895 measured reflections | l = −16→16 |
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) = 0.141 | H-atom parameters constrained |
S = 0.90 | w = 1/[σ2(Fo2) + (0.0591P)2] where P = (Fo2 + 2Fc2)/3 |
4099 reflections | (Δ/σ)max < 0.001 |
274 parameters | Δρmax = 0.17 e Å−3 |
6 restraints | Δρmin = −0.21 e Å−3 |
C21H15FN4O2 | V = 1881.66 (17) Å3 |
Mr = 374.37 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.7513 (5) Å | µ = 0.10 mm−1 |
b = 13.2684 (7) Å | T = 273 K |
c = 13.2210 (7) Å | 0.20 × 0.10 × 0.10 mm |
β = 93.890 (1)° |
Bruker SMART 4K CCD area-detector diffractometer | 4099 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 2039 reflections with I > 2σ(I) |
Tmin = 0.981, Tmax = 0.991 | Rint = 0.087 |
20895 measured reflections |
R[F2 > 2σ(F2)] = 0.060 | 6 restraints |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 0.90 | Δρmax = 0.17 e Å−3 |
4099 reflections | Δρmin = −0.21 e Å−3 |
274 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 | Occ. (<1) | |
C1 | 0.3122 (2) | 0.13945 (18) | 0.20338 (17) | 0.0528 (6) | |
C2 | 0.3710 (2) | 0.0917 (2) | 0.1285 (2) | 0.0726 (8) | |
H2 | 0.4348 | 0.0461 | 0.1451 | 0.087* | |
C3 | 0.3351 (3) | 0.1116 (2) | 0.0277 (2) | 0.0803 (8) | |
H3 | 0.3756 | 0.0811 | −0.0242 | 0.096* | |
C4 | 0.2401 (3) | 0.1761 (2) | 0.00691 (19) | 0.0698 (8) | |
C5 | 0.1809 (3) | 0.2252 (2) | 0.0792 (2) | 0.0756 (8) | |
H5 | 0.1166 | 0.2702 | 0.0620 | 0.091* | |
C6 | 0.2186 (2) | 0.20656 (19) | 0.17943 (18) | 0.0673 (7) | |
H6 | 0.1800 | 0.2398 | 0.2307 | 0.081* | |
C7 | 0.2762 (2) | 0.06506 (18) | 0.3691 (2) | 0.0572 (6) | |
C8 | 0.3997 (2) | 0.09608 (16) | 0.50746 (16) | 0.0481 (6) | |
C9 | 0.4827 (2) | 0.14991 (16) | 0.45414 (16) | 0.0464 (5) | |
C10 | 0.4589 (2) | 0.17129 (17) | 0.34947 (17) | 0.0519 (6) | |
C11 | 0.5521 (2) | 0.15273 (18) | 0.61627 (18) | 0.0561 (6) | |
H11 | 0.6013 | 0.1657 | 0.6754 | 0.067* | |
C12 | 0.4439 (2) | 0.09814 (17) | 0.61092 (16) | 0.0516 (6) | |
C13 | 0.3863 (2) | 0.0526 (2) | 0.6939 (2) | 0.0617 (7) | |
C14 | 0.6841 (2) | 0.24385 (18) | 0.50197 (17) | 0.0549 (6) | |
C15 | 0.7155 (2) | 0.3248 (2) | 0.5633 (2) | 0.0727 (8) | |
H15 | 0.6672 | 0.3410 | 0.6167 | 0.087* | |
C16 | 0.8181 (3) | 0.3818 (2) | 0.5454 (3) | 0.0946 (10) | |
H16 | 0.8393 | 0.4367 | 0.5868 | 0.114* | |
C17 | 0.8894 (3) | 0.3581 (3) | 0.4670 (3) | 0.1001 (11) | |
H17 | 0.9589 | 0.3970 | 0.4550 | 0.120* | |
C18 | 0.8581 (3) | 0.2764 (3) | 0.4058 (2) | 0.0899 (9) | |
H18 | 0.9065 | 0.2605 | 0.3523 | 0.108* | |
C19 | 0.7552 (2) | 0.2182 (2) | 0.4234 (2) | 0.0697 (7) | |
H19 | 0.7345 | 0.1626 | 0.3828 | 0.084* | |
C20 | 0.0819 (10) | −0.0131 (13) | 0.3779 (7) | 0.083 (3) | 0.65 (2) |
H20A | 0.0585 | 0.0380 | 0.4255 | 0.100* | 0.65 (2) |
H20B | 0.1110 | −0.0723 | 0.4155 | 0.100* | 0.65 (2) |
C21 | −0.0264 (6) | −0.0390 (9) | 0.3046 (6) | 0.093 (3) | 0.65 (2) |
H21A | −0.0556 | 0.0210 | 0.2699 | 0.140* | 0.65 (2) |
H21B | −0.0924 | −0.0672 | 0.3409 | 0.140* | 0.65 (2) |
H21C | −0.0003 | −0.0871 | 0.2561 | 0.140* | 0.65 (2) |
C21' | −0.0320 (12) | 0.0133 (19) | 0.352 (2) | 0.144 (8) | 0.35 (2) |
H21D | −0.0171 | 0.0747 | 0.3889 | 0.217* | 0.35 (2) |
H21E | −0.0945 | −0.0255 | 0.3828 | 0.217* | 0.35 (2) |
H21F | −0.0603 | 0.0288 | 0.2831 | 0.217* | 0.35 (2) |
C20' | 0.0904 (14) | −0.0484 (10) | 0.3525 (19) | 0.071 (5) | 0.35 (2) |
H20C | 0.1168 | −0.0708 | 0.4204 | 0.085* | 0.35 (2) |
H20D | 0.0810 | −0.1066 | 0.3082 | 0.085* | 0.35 (2) |
F1 | 0.20318 (17) | 0.19477 (13) | −0.09212 (10) | 0.1037 (6) | |
N1 | 0.35061 (17) | 0.12065 (14) | 0.30899 (13) | 0.0522 (5) | |
N2 | 0.29355 (17) | 0.05079 (14) | 0.46511 (15) | 0.0563 (5) | |
N3 | 0.57688 (17) | 0.18511 (14) | 0.52239 (14) | 0.0511 (5) | |
N4 | 0.3401 (2) | 0.01462 (19) | 0.75895 (18) | 0.0874 (8) | |
O1 | 0.17933 (16) | 0.02517 (14) | 0.31431 (12) | 0.0802 (6) | |
O2 | 0.51702 (16) | 0.22586 (14) | 0.29545 (12) | 0.0745 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0566 (14) | 0.0621 (15) | 0.0395 (15) | −0.0110 (12) | 0.0020 (12) | 0.0040 (12) |
C2 | 0.0683 (17) | 0.099 (2) | 0.0506 (18) | 0.0091 (15) | 0.0075 (14) | 0.0043 (15) |
C3 | 0.082 (2) | 0.118 (2) | 0.0420 (17) | −0.0072 (18) | 0.0119 (15) | −0.0034 (16) |
C4 | 0.081 (2) | 0.090 (2) | 0.0365 (16) | −0.0267 (17) | −0.0099 (14) | 0.0092 (15) |
C5 | 0.091 (2) | 0.082 (2) | 0.0516 (18) | 0.0023 (16) | −0.0100 (15) | 0.0057 (15) |
C6 | 0.0823 (19) | 0.0754 (18) | 0.0436 (16) | 0.0024 (15) | −0.0013 (14) | −0.0009 (13) |
C7 | 0.0492 (14) | 0.0687 (17) | 0.0538 (17) | −0.0062 (12) | 0.0028 (13) | 0.0050 (13) |
C8 | 0.0536 (14) | 0.0525 (14) | 0.0385 (14) | 0.0102 (11) | 0.0054 (11) | 0.0006 (11) |
C9 | 0.0500 (13) | 0.0546 (14) | 0.0352 (13) | 0.0025 (11) | 0.0061 (11) | 0.0010 (11) |
C10 | 0.0529 (14) | 0.0586 (15) | 0.0449 (15) | −0.0044 (12) | 0.0070 (12) | 0.0049 (12) |
C11 | 0.0628 (16) | 0.0669 (16) | 0.0383 (15) | 0.0127 (13) | 0.0012 (12) | −0.0076 (12) |
C12 | 0.0614 (15) | 0.0572 (15) | 0.0370 (15) | 0.0143 (12) | 0.0090 (12) | 0.0021 (11) |
C13 | 0.0693 (17) | 0.0736 (18) | 0.0426 (16) | 0.0161 (14) | 0.0059 (13) | 0.0022 (14) |
C14 | 0.0499 (14) | 0.0617 (16) | 0.0524 (16) | 0.0040 (12) | −0.0020 (12) | −0.0027 (13) |
C15 | 0.0681 (18) | 0.0745 (19) | 0.074 (2) | −0.0022 (15) | −0.0049 (15) | −0.0136 (15) |
C16 | 0.081 (2) | 0.090 (2) | 0.110 (3) | −0.0136 (19) | −0.008 (2) | −0.016 (2) |
C17 | 0.070 (2) | 0.105 (3) | 0.124 (3) | −0.0250 (19) | −0.002 (2) | 0.001 (2) |
C18 | 0.0674 (19) | 0.118 (3) | 0.086 (2) | −0.0061 (19) | 0.0174 (16) | 0.002 (2) |
C19 | 0.0624 (17) | 0.0803 (19) | 0.0672 (19) | −0.0003 (15) | 0.0091 (14) | −0.0061 (14) |
C20 | 0.079 (5) | 0.097 (7) | 0.075 (6) | −0.040 (5) | 0.008 (3) | 0.015 (4) |
C21 | 0.066 (4) | 0.128 (7) | 0.086 (5) | −0.029 (4) | 0.003 (3) | 0.002 (4) |
C21' | 0.128 (12) | 0.163 (17) | 0.14 (2) | 0.022 (11) | 0.029 (13) | 0.018 (12) |
C20' | 0.073 (8) | 0.087 (10) | 0.053 (9) | −0.025 (6) | 0.003 (6) | 0.004 (7) |
F1 | 0.1247 (14) | 0.1418 (15) | 0.0421 (10) | −0.0247 (12) | −0.0131 (9) | 0.0147 (9) |
N1 | 0.0524 (11) | 0.0683 (13) | 0.0360 (11) | −0.0075 (10) | 0.0041 (9) | 0.0083 (9) |
N2 | 0.0607 (13) | 0.0673 (13) | 0.0412 (13) | 0.0002 (10) | 0.0060 (10) | 0.0094 (10) |
N3 | 0.0542 (12) | 0.0605 (12) | 0.0385 (12) | 0.0025 (10) | 0.0020 (9) | −0.0033 (9) |
N4 | 0.0942 (18) | 0.112 (2) | 0.0575 (16) | 0.0063 (14) | 0.0210 (14) | 0.0230 (14) |
O1 | 0.0692 (12) | 0.1153 (15) | 0.0552 (12) | −0.0358 (11) | −0.0027 (10) | 0.0205 (10) |
O2 | 0.0754 (12) | 0.0968 (13) | 0.0505 (11) | −0.0280 (10) | −0.0012 (9) | 0.0203 (10) |
C1—C6 | 1.365 (3) | C14—C15 | 1.374 (3) |
C1—C2 | 1.366 (3) | C14—C19 | 1.374 (3) |
C1—N1 | 1.451 (3) | C14—N3 | 1.432 (3) |
C2—C3 | 1.388 (3) | C15—C16 | 1.371 (4) |
C2—H2 | 0.9300 | C15—H15 | 0.9300 |
C3—C4 | 1.346 (4) | C16—C17 | 1.367 (4) |
C3—H3 | 0.9300 | C16—H16 | 0.9300 |
C4—C5 | 1.352 (4) | C17—C18 | 1.381 (4) |
C4—F1 | 1.365 (3) | C17—H17 | 0.9300 |
C5—C6 | 1.381 (3) | C18—C19 | 1.382 (4) |
C5—H5 | 0.9300 | C18—H18 | 0.9300 |
C6—H6 | 0.9300 | C19—H19 | 0.9300 |
C7—N2 | 1.284 (3) | C20—O1 | 1.477 (6) |
C7—O1 | 1.337 (3) | C20—C21 | 1.504 (8) |
C7—N1 | 1.379 (3) | C20—H20A | 0.9700 |
C8—N2 | 1.374 (3) | C20—H20B | 0.9700 |
C8—C9 | 1.375 (3) | C21—H21A | 0.9600 |
C8—C12 | 1.418 (3) | C21—H21B | 0.9600 |
C9—N3 | 1.390 (3) | C21—H21C | 0.9600 |
C9—C10 | 1.419 (3) | C21'—C20' | 1.549 (10) |
C10—O2 | 1.219 (2) | C21'—H21D | 0.9600 |
C10—N1 | 1.417 (3) | C21'—H21E | 0.9600 |
C11—N3 | 1.357 (3) | C21'—H21F | 0.9600 |
C11—C12 | 1.368 (3) | C20'—O1 | 1.480 (9) |
C11—H11 | 0.9300 | C20'—H20C | 0.9700 |
C12—C13 | 1.429 (3) | C20'—H20D | 0.9700 |
C13—N4 | 1.140 (3) | ||
C6—C1—C2 | 120.3 (2) | C14—C15—H15 | 120.1 |
C6—C1—N1 | 119.5 (2) | C17—C16—C15 | 120.2 (3) |
C2—C1—N1 | 120.1 (2) | C17—C16—H16 | 119.9 |
C1—C2—C3 | 119.7 (3) | C15—C16—H16 | 119.9 |
C1—C2—H2 | 120.1 | C16—C17—C18 | 119.9 (3) |
C3—C2—H2 | 120.1 | C16—C17—H17 | 120.1 |
C4—C3—C2 | 118.3 (3) | C18—C17—H17 | 120.1 |
C4—C3—H3 | 120.8 | C17—C18—C19 | 120.4 (3) |
C2—C3—H3 | 120.8 | C17—C18—H18 | 119.8 |
C3—C4—C5 | 123.3 (2) | C19—C18—H18 | 119.8 |
C3—C4—F1 | 118.6 (3) | C14—C19—C18 | 118.8 (3) |
C5—C4—F1 | 118.1 (3) | C14—C19—H19 | 120.6 |
C4—C5—C6 | 118.1 (3) | C18—C19—H19 | 120.6 |
C4—C5—H5 | 121.0 | O1—C20—C21 | 105.0 (6) |
C6—C5—H5 | 121.0 | O1—C20—H20A | 110.7 |
C1—C6—C5 | 120.2 (2) | C21—C20—H20A | 110.7 |
C1—C6—H6 | 119.9 | O1—C20—H20B | 110.7 |
C5—C6—H6 | 119.9 | C21—C20—H20B | 110.7 |
N2—C7—O1 | 122.2 (2) | H20A—C20—H20B | 108.8 |
N2—C7—N1 | 126.7 (2) | C20'—C21'—H21D | 109.5 |
O1—C7—N1 | 111.1 (2) | C20'—C21'—H21E | 109.5 |
N2—C8—C9 | 124.6 (2) | H21D—C21'—H21E | 109.5 |
N2—C8—C12 | 128.0 (2) | C20'—C21'—H21F | 109.5 |
C9—C8—C12 | 107.3 (2) | H21D—C21'—H21F | 109.5 |
C8—C9—N3 | 108.15 (19) | H21E—C21'—H21F | 109.5 |
C8—C9—C10 | 121.6 (2) | O1—C20'—C21' | 102.6 (8) |
N3—C9—C10 | 129.9 (2) | O1—C20'—H20C | 111.3 |
O2—C10—N1 | 120.1 (2) | C21'—C20'—H20C | 111.3 |
O2—C10—C9 | 128.6 (2) | O1—C20'—H20D | 111.3 |
N1—C10—C9 | 111.3 (2) | C21'—C20'—H20D | 111.3 |
N3—C11—C12 | 109.8 (2) | H20C—C20'—H20D | 109.2 |
N3—C11—H11 | 125.1 | C7—N1—C10 | 121.96 (19) |
C12—C11—H11 | 125.1 | C7—N1—C1 | 120.56 (18) |
C11—C12—C8 | 106.8 (2) | C10—N1—C1 | 117.07 (17) |
C11—C12—C13 | 126.5 (2) | C7—N2—C8 | 113.5 (2) |
C8—C12—C13 | 126.7 (2) | C11—N3—C9 | 107.92 (19) |
N4—C13—C12 | 178.7 (3) | C11—N3—C14 | 123.73 (19) |
C15—C14—C19 | 120.8 (2) | C9—N3—C14 | 128.34 (19) |
C15—C14—N3 | 118.9 (2) | C7—O1—C20 | 112.6 (4) |
C19—C14—N3 | 120.3 (2) | C7—O1—C20' | 125.0 (10) |
C16—C15—C14 | 119.9 (3) | C20—O1—C20' | 22.9 (7) |
C16—C15—H15 | 120.1 | ||
C6—C1—C2—C3 | −0.1 (4) | N2—C7—N1—C10 | −0.7 (4) |
N1—C1—C2—C3 | −178.8 (2) | O1—C7—N1—C10 | 179.49 (19) |
C1—C2—C3—C4 | −1.7 (4) | N2—C7—N1—C1 | −173.2 (2) |
C2—C3—C4—C5 | 2.4 (4) | O1—C7—N1—C1 | 7.0 (3) |
C2—C3—C4—F1 | −179.1 (2) | O2—C10—N1—C7 | −174.4 (2) |
C3—C4—C5—C6 | −1.2 (4) | C9—C10—N1—C7 | 4.6 (3) |
F1—C4—C5—C6 | −179.8 (2) | O2—C10—N1—C1 | −1.7 (3) |
C2—C1—C6—C5 | 1.3 (4) | C9—C10—N1—C1 | 177.32 (19) |
N1—C1—C6—C5 | −180.0 (2) | C6—C1—N1—C7 | 73.3 (3) |
C4—C5—C6—C1 | −0.7 (4) | C2—C1—N1—C7 | −108.0 (3) |
N2—C8—C9—N3 | 179.27 (19) | C6—C1—N1—C10 | −99.5 (3) |
C12—C8—C9—N3 | −0.1 (2) | C2—C1—N1—C10 | 79.2 (3) |
N2—C8—C9—C10 | 6.0 (3) | O1—C7—N2—C8 | 178.6 (2) |
C12—C8—C9—C10 | −173.36 (19) | N1—C7—N2—C8 | −1.1 (3) |
C8—C9—C10—O2 | 172.0 (2) | C9—C8—N2—C7 | −1.5 (3) |
N3—C9—C10—O2 | 0.3 (4) | C12—C8—N2—C7 | 177.7 (2) |
C8—C9—C10—N1 | −7.0 (3) | C12—C11—N3—C9 | −0.5 (2) |
N3—C9—C10—N1 | −178.7 (2) | C12—C11—N3—C14 | −179.63 (19) |
N3—C11—C12—C8 | 0.4 (2) | C8—C9—N3—C11 | 0.3 (2) |
N3—C11—C12—C13 | −179.2 (2) | C10—C9—N3—C11 | 172.9 (2) |
N2—C8—C12—C11 | −179.5 (2) | C8—C9—N3—C14 | 179.4 (2) |
C9—C8—C12—C11 | −0.2 (2) | C10—C9—N3—C14 | −8.0 (4) |
N2—C8—C12—C13 | 0.1 (4) | C15—C14—N3—C11 | −46.1 (3) |
C9—C8—C12—C13 | 179.4 (2) | C19—C14—N3—C11 | 132.7 (2) |
C11—C12—C13—N4 | −135 (12) | C15—C14—N3—C9 | 134.9 (2) |
C8—C12—C13—N4 | 46 (12) | C19—C14—N3—C9 | −46.3 (3) |
C19—C14—C15—C16 | 0.8 (4) | N2—C7—O1—C20 | 14.4 (9) |
N3—C14—C15—C16 | 179.6 (2) | N1—C7—O1—C20 | −165.8 (8) |
C14—C15—C16—C17 | −0.1 (4) | N2—C7—O1—C20' | −7.7 (8) |
C15—C16—C17—C18 | −0.2 (5) | N1—C7—O1—C20' | 172.1 (7) |
C16—C17—C18—C19 | −0.2 (5) | C21—C20—O1—C7 | 171.1 (11) |
C15—C14—C19—C18 | −1.2 (4) | C21—C20—O1—C20' | −61 (3) |
N3—C14—C19—C18 | −180.0 (2) | C21'—C20'—O1—C7 | 112 (2) |
C17—C18—C19—C14 | 0.8 (4) | C21'—C20'—O1—C20 | 49 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···F1i | 0.93 | 2.49 | 3.306 (3) | 146 |
C11—H11···O2i | 0.93 | 2.37 | 2.910 (3) | 117 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C21H15FN4O2 |
Mr | 374.37 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 273 |
a, b, c (Å) | 10.7513 (5), 13.2684 (7), 13.2210 (7) |
β (°) | 93.890 (1) |
V (Å3) | 1881.66 (17) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.20 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART 4K CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.981, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20895, 4099, 2039 |
Rint | 0.087 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.141, 0.90 |
No. of reflections | 4099 |
No. of parameters | 274 |
No. of restraints | 6 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.21 |
Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···F1i | 0.93 | 2.49 | 3.306 (3) | 146.0 |
C11—H11···O2i | 0.93 | 2.37 | 2.910 (3) | 117.0 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
We have recently focused on the synthesis of fused heterocyclic systems containing a fused pyrimidinone unit using the aza-Wittig reaction (Ding et al., 2004). Some X-ray crystal structures of fused pyrimidinone derivatives have been reported (Hu, Li et al., 2005; Hu et al., 2006). Pyrrolopyrimidine derivatives are of great importance because of their remarkable biological properties (Shih, et al., 2002; Niwas, et al., 1994). We present here the structure of one such pyrrolopyrimidine derivative, (I) (Fig. 1), which may be used as a new precursor for obtaining bioactive molecules.
The bond lengths and angles in (I) are unexceptional. The pyrrole (A), the pyrimidinone (B) and the C1—C6 benzene(C), the C14—C19 benzene(D) rings are, of course, planar and the dihedral angles between them are A/B = 2.91 (12)°, B/C = 75.23 (12)°, A/D = 46.11 (14)°. C20, C21 and attached hydrogen atoms are disordered over two sites, with refined occupancies of 0.65 (2) and 0.35 (2). Intermolecular C—H···O and C—H···F hydrogen bonds (Fig. 2 and Table 2) seem to be effective in stabilizing the crystal structure. Further stability is provided by offset π-π stacking interactions (Janiak, 2000) involving A and B rings. The A:A interplanar distance are 3.315 (1) Å with distances between adjacent ring centroids of 3.796 (1) Å. (symmetry code relating the adjacent rings: 1 - x, -y, 1 - z). A further interaction occurs between two adjacent A and B rings (symmetry code: 1 - x, -y, 1 - z), with an interplanar distance of 3.300 (1) Å and a centroid-to-centroid distance of 3.592 (1) (Fig. 2).