Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031534/hb2430sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031534/hb2430Isup2.hkl |
CCDC reference: 657687
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.002 Å
- Disorder in main residue
- R factor = 0.044
- wR factor = 0.130
- Data-to-parameter ratio = 17.3
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O5 .. N1 .. 2.82 Ang.
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg. PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.02 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O5 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O5' PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT301_ALERT_3_C Main Residue Disorder ......................... 3.00 Perc. PLAT432_ALERT_2_C Short Inter X...Y Contact O5' .. C6 .. 3.01 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 28.20 Deg. O5 -C13 -O5' 1.555 1.555 1.555
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C9 = ... R
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A mixture of 2-nitroveratraldehyde (0.01 mol), ethylaceto acetate (0.015 mole), thiourea (0.01 mol) and concentrated sulfuric acid (1–2 drops) in ethanol (10 ml) taken in a borosil beaker (100 ml capacity) was zapped inside a microwave oven for 3–4 minutes (power = 160 watt). The reaction mixture was then allowed to stand at room temperature and poured into water. The product separated was filtered, washed with water followed by ethanol, dried and finally recrystallized from ethanol by slow evaporation at room temperature to yield pale yellow rectangular blocks of (I).
Atom O5 is disordered over two sites with equal occupancies. All the H atoms were placed geometrically (C—H = 0.93–0.97 Å, N—H = 0.86 Å) and refined as riding with Uiso(H) = 1.2Ueq(carrier) or 1.5Ueq(methyl C).
As part of our ongoing strudies of biologically active molecules (Kumaradhas et al., 2007), we now report the synthesis and structure of the title compound, (I), (Fig. 1).
Within the 1,4–pyridimine ring, the C10—N2 and C10—N3 bonds are somewhat short, and the C1—C2 bond of the substituent 2–nitro–4,5–dimethoxy phenyl ring is lengthened, probably due to steric factors. The pyridimine ring shows a distorted envelope conformation in which C9 and N3 lie above the mean plane of the other ring atoms, having deviations of 0.303 (1)Å and 0.144 (1)Å respectively.
The dihedral angle of the pendant phenyl and aromatic rings with the central ring are 85.9 (1)° and 86.4 (1)° respectively, which marks the near-perpendicularity of both the rings.
In the crystal, the molecules of (I) form inversion dimers (Table 1, Fig. 2) via pairs of N—H···S hydrogen bonds thus generating R22(8) loops. A weak C—H···O interaction also occurs.
For related literature, see: Kumaradhas et al. (2007).
Data collection: APEX (Bruker, 2000); cell refinement: SAINT; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C22H23N3O6S | Z = 2 |
Mr = 457.49 | F(000) = 480 |
Triclinic, P1 | Dx = 1.334 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.1475 (8) Å | Cell parameters from 25 reflections |
b = 10.3588 (10) Å | θ = 5–11° |
c = 14.8263 (15) Å | µ = 0.19 mm−1 |
α = 86.620 (2)° | T = 296 K |
β = 78.262 (2)° | Block, pale yellow |
γ = 68.395 (2)° | 0.21 × 0.11 × 0.08 mm |
V = 1138.90 (19) Å3 |
Bruker APEX II CCD diffractometer | Rint = 0.017 |
ω scans | θmax = 28.0°, θmin = 2.1° |
13201 measured reflections | h = −10→10 |
5229 independent reflections | k = −13→13 |
4549 reflections with I > 2σ(I) | l = −19→18 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.044 | w = 1/[σ2(Fo2) + (0.0709P)2 + 0.188P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.130 | (Δ/σ)max = 0.001 |
S = 1.09 | Δρmax = 0.32 e Å−3 |
5229 reflections | Δρmin = −0.22 e Å−3 |
302 parameters |
C22H23N3O6S | γ = 68.395 (2)° |
Mr = 457.49 | V = 1138.90 (19) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.1475 (8) Å | Mo Kα radiation |
b = 10.3588 (10) Å | µ = 0.19 mm−1 |
c = 14.8263 (15) Å | T = 296 K |
α = 86.620 (2)° | 0.21 × 0.11 × 0.08 mm |
β = 78.262 (2)° |
Bruker APEX II CCD diffractometer | 4549 reflections with I > 2σ(I) |
13201 measured reflections | Rint = 0.017 |
5229 independent reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.32 e Å−3 |
5229 reflections | Δρmin = −0.22 e Å−3 |
302 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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S | 0.45829 (6) | 0.83000 (4) | 0.43847 (3) | 0.05704 (14) | |
O1 | 0.66977 (18) | 0.55834 (12) | 0.92626 (9) | 0.0652 (3) | |
O2 | 0.52874 (18) | 0.47350 (11) | 0.81277 (8) | 0.0621 (3) | |
O3 | 0.3863 (2) | 1.11302 (13) | 0.77587 (9) | 0.0747 (4) | |
O4 | 0.38192 (18) | 1.07621 (12) | 0.92019 (8) | 0.0638 (3) | |
O5 | −0.2304 (13) | 0.9803 (10) | 0.8041 (8) | 0.090 (2) | 0.5 |
O5' | −0.1923 (13) | 0.9289 (10) | 0.8221 (8) | 0.089 (2) | 0.5 |
O6 | −0.04308 (15) | 1.06751 (13) | 0.83484 (8) | 0.0618 (3) | |
N1 | 0.39604 (17) | 1.03669 (12) | 0.84201 (9) | 0.0473 (3) | |
N2 | 0.32962 (15) | 0.93324 (12) | 0.60670 (8) | 0.0424 (3) | |
H2 | 0.3986 | 0.9801 | 0.5912 | 0.051* | |
N3 | 0.18386 (16) | 0.80205 (12) | 0.56207 (8) | 0.0447 (3) | |
C1 | 0.56626 (19) | 0.65847 (15) | 0.87698 (10) | 0.0461 (3) | |
C2 | 0.4914 (2) | 0.61169 (14) | 0.81356 (10) | 0.0457 (3) | |
C3 | 0.38765 (19) | 0.70637 (14) | 0.75925 (9) | 0.0434 (3) | |
H3 | 0.3384 | 0.6746 | 0.718 | 0.052* | |
C4 | 0.35371 (17) | 0.84891 (13) | 0.76403 (8) | 0.0372 (3) | |
C5 | 0.42686 (17) | 0.89020 (13) | 0.82832 (9) | 0.0381 (3) | |
C6 | 0.53023 (18) | 0.79808 (14) | 0.88500 (9) | 0.0429 (3) | |
H6 | 0.5748 | 0.8307 | 0.9281 | 0.052* | |
C7 | 0.7410 (3) | 0.6026 (2) | 0.99266 (16) | 0.0827 (6) | |
H7A | 0.8186 | 0.6497 | 0.9626 | 0.124* | |
H7B | 0.8086 | 0.5235 | 1.0242 | 0.124* | |
H7C | 0.6444 | 0.6649 | 1.0362 | 0.124* | |
C8 | 0.4525 (3) | 0.41968 (18) | 0.75192 (14) | 0.0709 (5) | |
H8A | 0.3236 | 0.4612 | 0.7673 | 0.106* | |
H8B | 0.4892 | 0.3208 | 0.7582 | 0.106* | |
H8C | 0.4936 | 0.441 | 0.6895 | 0.106* | |
C9 | 0.23486 (17) | 0.94602 (13) | 0.70240 (9) | 0.0384 (3) | |
H9 | 0.2029 | 1.0416 | 0.7236 | 0.046* | |
C10 | 0.31935 (18) | 0.85618 (13) | 0.54131 (9) | 0.0411 (3) | |
C11 | 0.04369 (18) | 0.84849 (14) | 0.64043 (10) | 0.0437 (3) | |
C12 | 0.06332 (18) | 0.92001 (14) | 0.70715 (10) | 0.0421 (3) | |
C13 | −0.0804 (2) | 0.97947 (18) | 0.78865 (11) | 0.0547 (4) | |
C14 | −0.1783 (3) | 1.1408 (2) | 0.91359 (14) | 0.0761 (5) | |
H14A | −0.2157 | 1.0754 | 0.954 | 0.091* | |
H14B | −0.2831 | 1.2066 | 0.8929 | 0.091* | |
C15 | −0.0993 (3) | 1.2135 (3) | 0.96261 (17) | 0.0924 (7) | |
H15A | 0.0002 | 1.1472 | 0.9857 | 0.139* | |
H15B | −0.1884 | 1.2664 | 1.0131 | 0.139* | |
H15C | −0.0577 | 1.2748 | 0.9213 | 0.139* | |
C16 | −0.1218 (2) | 0.8164 (2) | 0.63980 (14) | 0.0648 (4) | |
H16A | −0.2048 | 0.8462 | 0.6973 | 0.097* | |
H16B | −0.0885 | 0.7182 | 0.6316 | 0.097* | |
H16C | −0.1776 | 0.8643 | 0.5902 | 0.097* | |
C17 | 0.1732 (2) | 0.71097 (15) | 0.49452 (10) | 0.0456 (3) | |
C18 | 0.2479 (2) | 0.56988 (15) | 0.50319 (11) | 0.0495 (3) | |
H18 | 0.3075 | 0.5323 | 0.5513 | 0.059* | |
C19 | 0.2334 (2) | 0.48365 (17) | 0.43937 (13) | 0.0602 (4) | |
H19 | 0.2839 | 0.3878 | 0.4446 | 0.072* | |
C20 | 0.1453 (3) | 0.53926 (19) | 0.36889 (13) | 0.0667 (5) | |
H20 | 0.1357 | 0.4812 | 0.3264 | 0.08* | |
C21 | 0.0711 (3) | 0.6803 (2) | 0.36084 (14) | 0.0750 (5) | |
H21 | 0.0114 | 0.7178 | 0.3127 | 0.09* | |
C22 | 0.0843 (3) | 0.76721 (18) | 0.42366 (13) | 0.0653 (5) | |
H22 | 0.0336 | 0.863 | 0.4182 | 0.078* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S | 0.0731 (3) | 0.0625 (3) | 0.0431 (2) | −0.0406 (2) | 0.00476 (17) | −0.00769 (16) |
O1 | 0.0813 (8) | 0.0456 (6) | 0.0700 (7) | −0.0122 (6) | −0.0376 (6) | −0.0021 (5) |
O2 | 0.0946 (9) | 0.0369 (5) | 0.0626 (7) | −0.0250 (6) | −0.0302 (6) | −0.0007 (5) |
O3 | 0.1192 (11) | 0.0593 (7) | 0.0756 (8) | −0.0612 (8) | −0.0346 (8) | 0.0162 (6) |
O4 | 0.0815 (8) | 0.0499 (6) | 0.0617 (7) | −0.0215 (6) | −0.0166 (6) | −0.0194 (5) |
O5 | 0.050 (2) | 0.132 (7) | 0.093 (5) | −0.047 (4) | 0.014 (2) | −0.040 (4) |
O5' | 0.080 (5) | 0.122 (6) | 0.079 (4) | −0.071 (5) | 0.026 (3) | −0.019 (3) |
O6 | 0.0557 (6) | 0.0628 (7) | 0.0611 (7) | −0.0246 (5) | 0.0126 (5) | −0.0179 (5) |
N1 | 0.0533 (7) | 0.0435 (6) | 0.0530 (7) | −0.0261 (5) | −0.0100 (5) | −0.0051 (5) |
N2 | 0.0493 (6) | 0.0475 (6) | 0.0393 (6) | −0.0309 (5) | −0.0028 (5) | 0.0008 (4) |
N3 | 0.0509 (6) | 0.0445 (6) | 0.0470 (6) | −0.0272 (5) | −0.0085 (5) | −0.0019 (5) |
C1 | 0.0484 (7) | 0.0447 (7) | 0.0446 (7) | −0.0150 (6) | −0.0096 (6) | −0.0055 (6) |
C2 | 0.0574 (8) | 0.0368 (7) | 0.0449 (7) | −0.0193 (6) | −0.0089 (6) | −0.0048 (5) |
C3 | 0.0526 (7) | 0.0403 (7) | 0.0425 (7) | −0.0216 (6) | −0.0102 (6) | −0.0056 (5) |
C4 | 0.0393 (6) | 0.0387 (6) | 0.0356 (6) | −0.0195 (5) | −0.0004 (5) | −0.0044 (5) |
C5 | 0.0388 (6) | 0.0379 (6) | 0.0398 (6) | −0.0199 (5) | 0.0007 (5) | −0.0074 (5) |
C6 | 0.0435 (7) | 0.0470 (7) | 0.0417 (7) | −0.0202 (6) | −0.0061 (5) | −0.0081 (5) |
C7 | 0.1015 (15) | 0.0638 (11) | 0.0877 (14) | −0.0146 (10) | −0.0580 (13) | −0.0021 (10) |
C8 | 0.1120 (15) | 0.0466 (9) | 0.0721 (11) | −0.0417 (10) | −0.0328 (11) | −0.0006 (8) |
C9 | 0.0419 (6) | 0.0363 (6) | 0.0395 (6) | −0.0198 (5) | −0.0023 (5) | −0.0018 (5) |
C10 | 0.0479 (7) | 0.0380 (6) | 0.0419 (7) | −0.0216 (6) | −0.0079 (5) | 0.0035 (5) |
C11 | 0.0423 (7) | 0.0399 (7) | 0.0529 (8) | −0.0205 (6) | −0.0086 (6) | 0.0044 (5) |
C12 | 0.0402 (7) | 0.0411 (7) | 0.0471 (7) | −0.0193 (5) | −0.0057 (5) | 0.0038 (5) |
C13 | 0.0459 (8) | 0.0655 (9) | 0.0538 (8) | −0.0257 (7) | −0.0007 (6) | −0.0023 (7) |
C14 | 0.0600 (10) | 0.0847 (13) | 0.0672 (11) | −0.0180 (10) | 0.0148 (9) | −0.0229 (10) |
C15 | 0.0887 (15) | 0.0849 (15) | 0.0886 (15) | −0.0272 (12) | 0.0184 (12) | −0.0394 (12) |
C16 | 0.0544 (9) | 0.0724 (11) | 0.0808 (12) | −0.0386 (9) | −0.0101 (8) | −0.0065 (9) |
C17 | 0.0536 (8) | 0.0428 (7) | 0.0486 (7) | −0.0256 (6) | −0.0124 (6) | 0.0004 (6) |
C18 | 0.0551 (8) | 0.0448 (7) | 0.0536 (8) | −0.0226 (6) | −0.0144 (6) | 0.0044 (6) |
C19 | 0.0711 (10) | 0.0429 (8) | 0.0718 (11) | −0.0268 (7) | −0.0126 (8) | −0.0043 (7) |
C20 | 0.0886 (13) | 0.0644 (10) | 0.0639 (10) | −0.0435 (10) | −0.0193 (9) | −0.0084 (8) |
C21 | 0.1055 (15) | 0.0693 (11) | 0.0692 (11) | −0.0398 (11) | −0.0457 (11) | 0.0091 (9) |
C22 | 0.0893 (13) | 0.0454 (8) | 0.0726 (11) | −0.0266 (8) | −0.0392 (10) | 0.0089 (7) |
S—C10 | 1.6733 (14) | C7—H7C | 0.96 |
O1—C1 | 1.3558 (18) | C8—H8A | 0.96 |
O1—C7 | 1.414 (2) | C8—H8B | 0.96 |
O2—C2 | 1.3496 (16) | C8—H8C | 0.96 |
O2—C8 | 1.433 (2) | C9—C12 | 1.5053 (17) |
O3—N1 | 1.2195 (17) | C9—H9 | 0.98 |
O4—N1 | 1.2212 (16) | C11—C12 | 1.3383 (19) |
O5—C13 | 1.194 (10) | C11—C16 | 1.505 (2) |
O5'—C13 | 1.221 (10) | C12—C13 | 1.480 (2) |
O6—C13 | 1.325 (2) | C14—C15 | 1.457 (3) |
O6—C14 | 1.456 (2) | C14—H14A | 0.97 |
N1—C5 | 1.4635 (16) | C14—H14B | 0.97 |
N2—C10 | 1.3257 (17) | C15—H15A | 0.96 |
N2—C9 | 1.4588 (16) | C15—H15B | 0.96 |
N2—H2 | 0.86 | C15—H15C | 0.96 |
N3—C10 | 1.3874 (17) | C16—H16A | 0.96 |
N3—C11 | 1.4166 (18) | C16—H16B | 0.96 |
N3—C17 | 1.4518 (17) | C16—H16C | 0.96 |
C1—C6 | 1.3730 (19) | C17—C18 | 1.370 (2) |
C1—C2 | 1.4128 (19) | C17—C22 | 1.376 (2) |
C2—C3 | 1.378 (2) | C18—C19 | 1.389 (2) |
C3—C4 | 1.4020 (18) | C18—H18 | 0.93 |
C3—H3 | 0.93 | C19—C20 | 1.367 (3) |
C4—C5 | 1.3833 (17) | C19—H19 | 0.93 |
C4—C9 | 1.5228 (18) | C20—C21 | 1.369 (3) |
C5—C6 | 1.388 (2) | C20—H20 | 0.93 |
C6—H6 | 0.93 | C21—C22 | 1.379 (2) |
C7—H7A | 0.96 | C21—H21 | 0.93 |
C7—H7B | 0.96 | C22—H22 | 0.93 |
C1—O1—C7 | 116.94 (13) | N3—C10—S | 122.04 (10) |
C2—O2—C8 | 117.96 (12) | C12—C11—N3 | 119.26 (12) |
C13—O6—C14 | 117.29 (14) | C12—C11—C16 | 124.83 (14) |
O3—N1—O4 | 123.17 (13) | N3—C11—C16 | 115.88 (13) |
O3—N1—C5 | 119.24 (12) | C11—C12—C13 | 122.83 (13) |
O4—N1—C5 | 117.60 (12) | C11—C12—C9 | 121.15 (12) |
C10—N2—C9 | 126.12 (11) | C13—C12—C9 | 116.02 (12) |
C10—N2—H2 | 116.9 | O5—C13—O5' | 28.2 (6) |
C9—N2—H2 | 116.9 | O5—C13—O6 | 118.7 (6) |
C10—N3—C11 | 121.49 (11) | O5'—C13—O6 | 122.6 (6) |
C10—N3—C17 | 118.25 (12) | O5—C13—C12 | 127.9 (6) |
C11—N3—C17 | 119.66 (11) | O5'—C13—C12 | 123.7 (6) |
O1—C1—C6 | 124.99 (13) | O6—C13—C12 | 111.26 (12) |
O1—C1—C2 | 115.74 (12) | O6—C14—C15 | 108.14 (16) |
C6—C1—C2 | 119.27 (13) | O6—C14—H14A | 110.1 |
O2—C2—C3 | 125.40 (12) | C15—C14—H14A | 110.1 |
O2—C2—C1 | 115.11 (13) | O6—C14—H14B | 110.1 |
C3—C2—C1 | 119.49 (12) | C15—C14—H14B | 110.1 |
C2—C3—C4 | 122.31 (12) | H14A—C14—H14B | 108.4 |
C2—C3—H3 | 118.8 | C14—C15—H15A | 109.5 |
C4—C3—H3 | 118.8 | C14—C15—H15B | 109.5 |
C5—C4—C3 | 116.15 (12) | H15A—C15—H15B | 109.5 |
C5—C4—C9 | 125.22 (11) | C14—C15—H15C | 109.5 |
C3—C4—C9 | 118.58 (11) | H15A—C15—H15C | 109.5 |
C4—C5—C6 | 123.17 (12) | H15B—C15—H15C | 109.5 |
C4—C5—N1 | 121.33 (12) | C11—C16—H16A | 109.5 |
C6—C5—N1 | 115.50 (11) | C11—C16—H16B | 109.5 |
C1—C6—C5 | 119.56 (12) | H16A—C16—H16B | 109.5 |
C1—C6—H6 | 120.2 | C11—C16—H16C | 109.5 |
C5—C6—H6 | 120.2 | H16A—C16—H16C | 109.5 |
O1—C7—H7A | 109.5 | H16B—C16—H16C | 109.5 |
O1—C7—H7B | 109.5 | C18—C17—C22 | 120.62 (14) |
H7A—C7—H7B | 109.5 | C18—C17—N3 | 119.71 (13) |
O1—C7—H7C | 109.5 | C22—C17—N3 | 119.65 (13) |
H7A—C7—H7C | 109.5 | C17—C18—C19 | 119.26 (14) |
H7B—C7—H7C | 109.5 | C17—C18—H18 | 120.4 |
O2—C8—H8A | 109.5 | C19—C18—H18 | 120.4 |
O2—C8—H8B | 109.5 | C20—C19—C18 | 120.23 (15) |
H8A—C8—H8B | 109.5 | C20—C19—H19 | 119.9 |
O2—C8—H8C | 109.5 | C18—C19—H19 | 119.9 |
H8A—C8—H8C | 109.5 | C19—C20—C21 | 120.08 (16) |
H8B—C8—H8C | 109.5 | C19—C20—H20 | 120 |
N2—C9—C12 | 109.01 (10) | C21—C20—H20 | 120 |
N2—C9—C4 | 111.33 (11) | C20—C21—C22 | 120.35 (16) |
C12—C9—C4 | 112.06 (10) | C20—C21—H21 | 119.8 |
N2—C9—H9 | 108.1 | C22—C21—H21 | 119.8 |
C12—C9—H9 | 108.1 | C17—C22—C21 | 119.46 (16) |
C4—C9—H9 | 108.1 | C17—C22—H22 | 120.3 |
N2—C10—N3 | 116.24 (12) | C21—C22—H22 | 120.3 |
N2—C10—S | 121.69 (10) | ||
C7—O1—C1—C6 | 1.9 (2) | C17—N3—C10—S | 5.02 (18) |
C7—O1—C1—C2 | −177.74 (17) | C10—N3—C11—C12 | −16.1 (2) |
C8—O2—C2—C3 | −1.2 (2) | C17—N3—C11—C12 | 172.90 (12) |
C8—O2—C2—C1 | 178.20 (15) | C10—N3—C11—C16 | 161.79 (14) |
O1—C1—C2—O2 | 2.0 (2) | C17—N3—C11—C16 | −9.19 (19) |
C6—C1—C2—O2 | −177.72 (13) | N3—C11—C12—C13 | 176.31 (13) |
O1—C1—C2—C3 | −178.59 (14) | C16—C11—C12—C13 | −1.4 (2) |
C6—C1—C2—C3 | 1.7 (2) | N3—C11—C12—C9 | −2.9 (2) |
O2—C2—C3—C4 | 179.72 (14) | C16—C11—C12—C9 | 179.39 (14) |
C1—C2—C3—C4 | 0.3 (2) | N2—C9—C12—C11 | 21.97 (17) |
C2—C3—C4—C5 | −1.5 (2) | C4—C9—C12—C11 | −101.72 (14) |
C2—C3—C4—C9 | −178.99 (13) | N2—C9—C12—C13 | −157.29 (12) |
C3—C4—C5—C6 | 0.75 (19) | C4—C9—C12—C13 | 79.02 (15) |
C9—C4—C5—C6 | 178.01 (12) | C14—O6—C13—O5 | 11.5 (5) |
C3—C4—C5—N1 | −177.98 (12) | C14—O6—C13—O5' | −21.1 (5) |
C9—C4—C5—N1 | −0.71 (19) | C14—O6—C13—C12 | 176.21 (15) |
O3—N1—C5—C4 | −35.34 (19) | C11—C12—C13—O5 | −4.6 (5) |
O4—N1—C5—C4 | 144.93 (13) | C9—C12—C13—O5 | 174.6 (5) |
O3—N1—C5—C6 | 145.85 (14) | C11—C12—C13—O5' | 29.9 (6) |
O4—N1—C5—C6 | −33.89 (17) | C9—C12—C13—O5' | −150.8 (5) |
O1—C1—C6—C5 | 177.86 (14) | C11—C12—C13—O6 | −167.62 (14) |
C2—C1—C6—C5 | −2.5 (2) | C9—C12—C13—O6 | 11.62 (19) |
C4—C5—C6—C1 | 1.3 (2) | C13—O6—C14—C15 | 170.88 (19) |
N1—C5—C6—C1 | −179.94 (12) | C10—N3—C17—C18 | 97.45 (16) |
C10—N2—C9—C12 | −27.44 (18) | C11—N3—C17—C18 | −91.28 (17) |
C10—N2—C9—C4 | 96.69 (15) | C10—N3—C17—C22 | −84.14 (19) |
C5—C4—C9—N2 | 108.95 (13) | C11—N3—C17—C22 | 87.13 (18) |
C3—C4—C9—N2 | −73.85 (14) | C22—C17—C18—C19 | 0.2 (2) |
C5—C4—C9—C12 | −128.66 (13) | N3—C17—C18—C19 | 178.56 (14) |
C3—C4—C9—C12 | 48.54 (16) | C17—C18—C19—C20 | −0.1 (3) |
C9—N2—C10—N3 | 11.6 (2) | C18—C19—C20—C21 | 0.1 (3) |
C9—N2—C10—S | −170.21 (11) | C19—C20—C21—C22 | −0.1 (3) |
C11—N3—C10—N2 | 12.12 (19) | C18—C17—C22—C21 | −0.2 (3) |
C17—N3—C10—N2 | −176.78 (12) | N3—C17—C22—C21 | −178.56 (17) |
C11—N3—C10—S | −166.08 (10) | C20—C21—C22—C17 | 0.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···Si | 0.86 | 2.61 | 3.4505 (11) | 167 |
C8—H8B···O3ii | 0.96 | 2.56 | 3.400 (2) | 146 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C22H23N3O6S |
Mr | 457.49 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 8.1475 (8), 10.3588 (10), 14.8263 (15) |
α, β, γ (°) | 86.620 (2), 78.262 (2), 68.395 (2) |
V (Å3) | 1138.90 (19) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.19 |
Crystal size (mm) | 0.21 × 0.11 × 0.08 |
Data collection | |
Diffractometer | Bruker APEX II CCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13201, 5229, 4549 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.661 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.130, 1.09 |
No. of reflections | 5229 |
No. of parameters | 302 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.32, −0.22 |
Computer programs: APEX (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···Si | 0.86 | 2.61 | 3.4505 (11) | 167 |
C8—H8B···O3ii | 0.96 | 2.56 | 3.400 (2) | 146 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x, y−1, z. |
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As part of our ongoing strudies of biologically active molecules (Kumaradhas et al., 2007), we now report the synthesis and structure of the title compound, (I), (Fig. 1).
Within the 1,4–pyridimine ring, the C10—N2 and C10—N3 bonds are somewhat short, and the C1—C2 bond of the substituent 2–nitro–4,5–dimethoxy phenyl ring is lengthened, probably due to steric factors. The pyridimine ring shows a distorted envelope conformation in which C9 and N3 lie above the mean plane of the other ring atoms, having deviations of 0.303 (1)Å and 0.144 (1)Å respectively.
The dihedral angle of the pendant phenyl and aromatic rings with the central ring are 85.9 (1)° and 86.4 (1)° respectively, which marks the near-perpendicularity of both the rings.
In the crystal, the molecules of (I) form inversion dimers (Table 1, Fig. 2) via pairs of N—H···S hydrogen bonds thus generating R22(8) loops. A weak C—H···O interaction also occurs.