


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808018497/bh2175sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808018497/bh2175Isup2.hkl |
CCDC reference: 696592
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.006 Å
- R factor = 0.055
- wR factor = 0.171
- Data-to-parameter ratio = 14.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT360_ALERT_2_B Short C(sp3)-C(sp3) Bond C30 - C31 ... 1.25 Ang.
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc. PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C9 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C27 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C32 - C33 ... 1.38 Ang. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT194_ALERT_1_C Missing _cell_measurement_reflns_used datum .... ? PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C32 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C33
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT793_ALERT_4_G Check the Absolute Configuration of C10 ..... S PLAT793_ALERT_4_G Check the Absolute Configuration of C20 ..... S
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 4 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 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
2,6-Dimethyl-3,5-di-[3-(4-chlorophenyl)-acryloyl-pyridine (1 mmol, 0.436 g), and 85% hydrazine hydrate solution (4 mmol, 0.235 g) were dissolved in 5 mL of acetic acid. The mixture was refluxed for 8 h, and then allowed to cool to room temperature. The reaction mixture was poured into crushed ice, and neutralized with diluted NaOH solution. The solid separated was filtered off, washed with water, dried and recrystallized from ethyl acetate, to give a colourless compound in a yield of of 42% (m.p. 489–491 K). Single crystals suitable for X-ray analysis were obtained form tetrahydrofuran at room temperature.
All H atoms were placed in calculated positions, with C—H = 0.93–0.98 Å, and included in the final cycles of refinement using a riding model and Uiso(H) = 1.2–1.5Ueq(C). The THF solvate molecule has high displacement parameters, suggesting that the molecule is probably disordered over a number of positions.
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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).
C29H27Cl2N5O2·C4H8O | F(000) = 1304 |
Mr = 620.56 | Dx = 1.276 Mg m−3 |
Monoclinic, P21/c | Melting point = 489–491 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 16.888 (3) Å | θ = 2.2–20.8° |
b = 11.180 (2) Å | µ = 0.24 mm−1 |
c = 17.313 (4) Å | T = 293 K |
β = 98.69 (3)° | Prism, colourless |
V = 3231.5 (11) Å3 | 0.20 × 0.20 × 0.10 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 5715 independent reflections |
Radiation source: fine-focus sealed tube | 2714 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
ω scans | θmax = 25.1°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −20→17 |
Tmin = 0.953, Tmax = 0.976 | k = −13→13 |
16422 measured reflections | l = −14→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.055 | H-atom parameters constrained |
wR(F2) = 0.171 | w = 1/[σ2(Fo2) + (0.0811P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.95 | (Δ/σ)max < 0.001 |
5715 reflections | Δρmax = 0.31 e Å−3 |
393 parameters | Δρmin = −0.36 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0020 (6) |
C29H27Cl2N5O2·C4H8O | V = 3231.5 (11) Å3 |
Mr = 620.56 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.888 (3) Å | µ = 0.24 mm−1 |
b = 11.180 (2) Å | T = 293 K |
c = 17.313 (4) Å | 0.20 × 0.20 × 0.10 mm |
β = 98.69 (3)° |
Bruker SMART CCD area-detector diffractometer | 5715 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2714 reflections with I > 2σ(I) |
Tmin = 0.953, Tmax = 0.976 | Rint = 0.037 |
16422 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.171 | H-atom parameters constrained |
S = 0.95 | Δρmax = 0.31 e Å−3 |
5715 reflections | Δρmin = −0.36 e Å−3 |
393 parameters |
x | y | z | Uiso*/Ueq | ||
C1 | 0.60818 (16) | 0.4491 (2) | 0.07953 (16) | 0.0487 (7) | |
C2 | 0.61080 (17) | 0.4038 (2) | 0.00456 (17) | 0.0545 (8) | |
C3 | 0.5585 (2) | 0.3053 (3) | −0.03305 (18) | 0.0768 (10) | |
H3A | 0.5763 | 0.2822 | −0.0810 | 0.115* | |
H3B | 0.5041 | 0.3327 | −0.0438 | 0.115* | |
H3C | 0.5617 | 0.2378 | 0.0015 | 0.115* | |
N1 | 0.66326 (15) | 0.4459 (2) | −0.03987 (13) | 0.0595 (7) | |
C5 | 0.71460 (17) | 0.5337 (3) | −0.01436 (16) | 0.0567 (8) | |
C6 | 0.7692 (2) | 0.5687 (3) | −0.07116 (18) | 0.0774 (10) | |
H6A | 0.7591 | 0.5185 | −0.1165 | 0.116* | |
H6B | 0.8239 | 0.5594 | −0.0470 | 0.116* | |
H6C | 0.7597 | 0.6507 | −0.0863 | 0.116* | |
C7 | 0.71516 (16) | 0.5856 (2) | 0.05992 (16) | 0.0497 (7) | |
C8 | 0.55499 (17) | 0.4029 (3) | 0.13232 (16) | 0.0515 (7) | |
C9 | 0.56623 (19) | 0.4295 (3) | 0.21808 (17) | 0.0738 (10) | |
H9A | 0.5641 | 0.5149 | 0.2275 | 0.089* | |
H9B | 0.6170 | 0.3986 | 0.2440 | 0.089* | |
C10 | 0.49590 (18) | 0.3651 (3) | 0.24637 (16) | 0.0605 (8) | |
H10 | 0.5166 | 0.3034 | 0.2843 | 0.073* | |
C11 | 0.43991 (17) | 0.4448 (3) | 0.28162 (16) | 0.0556 (8) | |
C12 | 0.4319 (2) | 0.4375 (3) | 0.35906 (19) | 0.0790 (10) | |
H12 | 0.4622 | 0.3818 | 0.3906 | 0.095* | |
C13 | 0.3796 (2) | 0.5111 (3) | 0.3915 (2) | 0.0890 (11) | |
H13 | 0.3751 | 0.5048 | 0.4442 | 0.107* | |
C14 | 0.3353 (2) | 0.5921 (3) | 0.3460 (2) | 0.0743 (10) | |
C15 | 0.3422 (2) | 0.6030 (3) | 0.2690 (2) | 0.0839 (11) | |
H15 | 0.3123 | 0.6597 | 0.2380 | 0.101* | |
C16 | 0.3946 (2) | 0.5282 (3) | 0.23771 (19) | 0.0773 (10) | |
H16 | 0.3989 | 0.5352 | 0.1850 | 0.093* | |
C17 | 0.40085 (19) | 0.2213 (3) | 0.1693 (2) | 0.0646 (9) | |
C18 | 0.3759 (2) | 0.1615 (3) | 0.0924 (2) | 0.0840 (11) | |
H18A | 0.4167 | 0.1062 | 0.0826 | 0.126* | |
H18B | 0.3683 | 0.2206 | 0.0517 | 0.126* | |
H18C | 0.3266 | 0.1191 | 0.0934 | 0.126* | |
C19 | 0.76779 (17) | 0.6835 (2) | 0.09060 (17) | 0.0533 (7) | |
C20 | 0.82785 (18) | 0.8467 (3) | 0.16815 (18) | 0.0634 (8) | |
H20 | 0.7995 | 0.9234 | 0.1628 | 0.076* | |
C21 | 0.7666 (2) | 0.7438 (3) | 0.16844 (18) | 0.0712 (9) | |
H21A | 0.7830 | 0.6890 | 0.2113 | 0.085* | |
H21B | 0.7137 | 0.7746 | 0.1726 | 0.085* | |
C22 | 0.9101 (2) | 0.8921 (3) | 0.0629 (2) | 0.0842 (11) | |
C23 | 0.9350 (3) | 0.8490 (4) | −0.0120 (2) | 0.1197 (17) | |
H23A | 0.9754 | 0.9012 | −0.0265 | 0.179* | |
H23B | 0.8894 | 0.8489 | −0.0526 | 0.179* | |
H23C | 0.9560 | 0.7693 | −0.0049 | 0.179* | |
C24 | 0.89355 (19) | 0.8516 (3) | 0.23768 (18) | 0.0601 (8) | |
C25 | 0.9417 (2) | 0.7542 (3) | 0.2596 (2) | 0.0760 (10) | |
H25 | 0.9321 | 0.6827 | 0.2324 | 0.091* | |
C26 | 1.0037 (3) | 0.7608 (4) | 0.3210 (2) | 0.0918 (12) | |
H26 | 1.0359 | 0.6945 | 0.3353 | 0.110* | |
C27 | 1.0171 (3) | 0.8655 (5) | 0.3602 (2) | 0.0953 (12) | |
C28 | 0.9697 (3) | 0.9627 (4) | 0.3417 (2) | 0.0921 (12) | |
H28 | 0.9789 | 1.0331 | 0.3703 | 0.111* | |
C29 | 0.9079 (2) | 0.9559 (3) | 0.2799 (2) | 0.0767 (10) | |
H29 | 0.8755 | 1.0223 | 0.2667 | 0.092* | |
C30 | 0.7975 (7) | 0.4446 (8) | 0.3062 (6) | 0.264 (6) | |
H30A | 0.7778 | 0.4645 | 0.2521 | 0.317* | |
H30B | 0.8069 | 0.5180 | 0.3359 | 0.317* | |
C31 | 0.8602 (6) | 0.3835 (13) | 0.3112 (7) | 0.272 (6) | |
H31A | 0.9071 | 0.4317 | 0.3291 | 0.327* | |
H31B | 0.8659 | 0.3474 | 0.2614 | 0.327* | |
C32 | 0.8479 (8) | 0.2933 (8) | 0.3685 (10) | 0.309 (7) | |
H32A | 0.8321 | 0.2176 | 0.3435 | 0.371* | |
H32B | 0.8961 | 0.2815 | 0.4060 | 0.371* | |
C33 | 0.7871 (7) | 0.3404 (12) | 0.4042 (4) | 0.259 (5) | |
H33A | 0.7612 | 0.2811 | 0.4327 | 0.311* | |
H33B | 0.8041 | 0.4083 | 0.4374 | 0.311* | |
Cl1 | 1.09785 (9) | 0.87718 (15) | 0.43586 (8) | 0.1632 (7) | |
Cl2 | 0.26751 (7) | 0.68157 (10) | 0.38565 (7) | 0.1173 (5) | |
C4 | 0.66139 (16) | 0.5401 (2) | 0.10563 (15) | 0.0507 (7) | |
H4A | 0.6610 | 0.5716 | 0.1553 | 0.061* | |
N2 | 0.49515 (14) | 0.3347 (2) | 0.10922 (13) | 0.0552 (6) | |
N3 | 0.45775 (15) | 0.3068 (2) | 0.17305 (14) | 0.0623 (7) | |
N4 | 0.82032 (15) | 0.7275 (2) | 0.05271 (14) | 0.0632 (7) | |
N5 | 0.85993 (15) | 0.8201 (2) | 0.09521 (14) | 0.0677 (7) | |
O1 | 0.37297 (14) | 0.19533 (19) | 0.22848 (14) | 0.0840 (7) | |
O2 | 0.93475 (17) | 0.9838 (2) | 0.09668 (14) | 0.1037 (9) | |
O3 | 0.7430 (3) | 0.3717 (6) | 0.3371 (5) | 0.261 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0502 (18) | 0.0502 (17) | 0.0481 (17) | −0.0035 (14) | 0.0149 (13) | 0.0042 (13) |
C2 | 0.0529 (19) | 0.0607 (19) | 0.0503 (18) | −0.0040 (15) | 0.0093 (15) | 0.0033 (14) |
C3 | 0.086 (3) | 0.090 (2) | 0.057 (2) | −0.029 (2) | 0.0194 (17) | −0.0155 (17) |
N1 | 0.0638 (17) | 0.0687 (17) | 0.0483 (15) | −0.0095 (14) | 0.0156 (13) | −0.0002 (12) |
C5 | 0.059 (2) | 0.065 (2) | 0.0502 (19) | −0.0019 (17) | 0.0198 (15) | 0.0054 (15) |
C6 | 0.079 (2) | 0.097 (3) | 0.062 (2) | −0.018 (2) | 0.0332 (18) | −0.0049 (18) |
C7 | 0.0493 (18) | 0.0514 (17) | 0.0509 (18) | −0.0021 (14) | 0.0160 (14) | 0.0049 (13) |
C8 | 0.0512 (19) | 0.0568 (18) | 0.0483 (18) | −0.0031 (15) | 0.0130 (14) | 0.0025 (14) |
C9 | 0.069 (2) | 0.106 (3) | 0.0494 (19) | −0.0218 (19) | 0.0191 (16) | −0.0043 (17) |
C10 | 0.063 (2) | 0.071 (2) | 0.0493 (18) | −0.0085 (17) | 0.0149 (15) | 0.0097 (15) |
C11 | 0.060 (2) | 0.065 (2) | 0.0429 (18) | −0.0101 (16) | 0.0134 (15) | 0.0078 (15) |
C12 | 0.101 (3) | 0.085 (3) | 0.053 (2) | 0.013 (2) | 0.0188 (19) | 0.0137 (18) |
C13 | 0.120 (3) | 0.094 (3) | 0.059 (2) | 0.003 (3) | 0.032 (2) | 0.003 (2) |
C14 | 0.074 (2) | 0.069 (2) | 0.082 (3) | −0.0083 (19) | 0.017 (2) | −0.0141 (19) |
C15 | 0.091 (3) | 0.076 (2) | 0.080 (3) | 0.008 (2) | −0.001 (2) | 0.005 (2) |
C16 | 0.088 (3) | 0.090 (3) | 0.053 (2) | 0.006 (2) | 0.0098 (18) | 0.0104 (19) |
C17 | 0.064 (2) | 0.056 (2) | 0.080 (3) | −0.0052 (17) | 0.0312 (18) | 0.0061 (17) |
C18 | 0.086 (3) | 0.071 (2) | 0.100 (3) | −0.025 (2) | 0.028 (2) | −0.013 (2) |
C19 | 0.0510 (18) | 0.0547 (18) | 0.0569 (19) | −0.0065 (15) | 0.0166 (15) | 0.0053 (14) |
C20 | 0.061 (2) | 0.059 (2) | 0.074 (2) | −0.0064 (16) | 0.0248 (17) | −0.0054 (16) |
C21 | 0.067 (2) | 0.079 (2) | 0.074 (2) | −0.0209 (18) | 0.0321 (17) | −0.0136 (17) |
C22 | 0.088 (3) | 0.090 (3) | 0.078 (3) | −0.042 (2) | 0.026 (2) | 0.006 (2) |
C23 | 0.138 (4) | 0.149 (4) | 0.086 (3) | −0.075 (3) | 0.063 (3) | −0.016 (3) |
C24 | 0.065 (2) | 0.058 (2) | 0.062 (2) | −0.0119 (17) | 0.0270 (16) | −0.0035 (16) |
C25 | 0.087 (3) | 0.065 (2) | 0.078 (2) | −0.009 (2) | 0.018 (2) | −0.0066 (18) |
C26 | 0.093 (3) | 0.091 (3) | 0.089 (3) | 0.006 (2) | 0.010 (2) | 0.014 (2) |
C27 | 0.103 (3) | 0.111 (3) | 0.070 (3) | −0.026 (3) | 0.008 (2) | 0.000 (2) |
C28 | 0.112 (3) | 0.087 (3) | 0.078 (3) | −0.031 (3) | 0.016 (2) | −0.027 (2) |
C29 | 0.089 (3) | 0.063 (2) | 0.082 (3) | −0.0087 (19) | 0.026 (2) | −0.0139 (18) |
C30 | 0.200 (9) | 0.245 (10) | 0.344 (12) | −0.037 (9) | 0.030 (9) | 0.194 (9) |
C31 | 0.172 (8) | 0.43 (2) | 0.246 (11) | 0.069 (10) | 0.118 (8) | 0.043 (10) |
C32 | 0.337 (17) | 0.183 (8) | 0.391 (19) | 0.106 (9) | 0.002 (13) | 0.113 (10) |
C33 | 0.288 (13) | 0.412 (17) | 0.082 (5) | 0.054 (11) | 0.046 (6) | 0.043 (7) |
Cl1 | 0.1458 (12) | 0.2111 (15) | 0.1152 (10) | −0.0404 (11) | −0.0362 (9) | 0.0005 (9) |
Cl2 | 0.1092 (9) | 0.1077 (9) | 0.1404 (10) | 0.0055 (7) | 0.0365 (7) | −0.0408 (7) |
C4 | 0.0535 (18) | 0.0540 (18) | 0.0476 (17) | −0.0036 (15) | 0.0173 (14) | −0.0003 (13) |
N2 | 0.0572 (16) | 0.0591 (15) | 0.0530 (15) | −0.0118 (13) | 0.0199 (12) | 0.0011 (12) |
N3 | 0.0685 (18) | 0.0679 (17) | 0.0552 (16) | −0.0182 (14) | 0.0247 (13) | −0.0002 (12) |
N4 | 0.0627 (18) | 0.0715 (17) | 0.0588 (16) | −0.0186 (14) | 0.0205 (13) | 0.0003 (13) |
N5 | 0.0727 (18) | 0.0739 (18) | 0.0610 (17) | −0.0265 (15) | 0.0251 (14) | −0.0021 (14) |
O1 | 0.0943 (18) | 0.0717 (15) | 0.0984 (18) | −0.0104 (13) | 0.0544 (14) | 0.0121 (13) |
O2 | 0.127 (2) | 0.0940 (19) | 0.0980 (19) | −0.0551 (17) | 0.0416 (16) | −0.0050 (15) |
O3 | 0.146 (4) | 0.291 (7) | 0.330 (9) | −0.017 (4) | −0.017 (5) | 0.093 (6) |
C1—C4 | 1.387 (3) | C19—N4 | 1.278 (3) |
C1—C2 | 1.400 (4) | C19—C21 | 1.509 (4) |
C1—C8 | 1.469 (4) | C20—N5 | 1.478 (4) |
C2—N1 | 1.343 (3) | C20—C24 | 1.510 (4) |
C2—C3 | 1.497 (4) | C20—C21 | 1.547 (4) |
C3—H3A | 0.9600 | C20—H20 | 0.9800 |
C3—H3B | 0.9600 | C21—H21A | 0.9700 |
C3—H3C | 0.9600 | C21—H21B | 0.9700 |
N1—C5 | 1.340 (3) | C22—O2 | 1.222 (4) |
C5—C7 | 1.410 (4) | C22—N5 | 1.350 (4) |
C5—C6 | 1.498 (4) | C22—C23 | 1.502 (5) |
C6—H6A | 0.9600 | C23—H23A | 0.9600 |
C6—H6B | 0.9600 | C23—H23B | 0.9600 |
C6—H6C | 0.9600 | C23—H23C | 0.9600 |
C7—C4 | 1.388 (4) | C24—C25 | 1.377 (4) |
C7—C19 | 1.459 (4) | C24—C29 | 1.378 (4) |
C8—N2 | 1.281 (3) | C25—C26 | 1.378 (5) |
C8—C9 | 1.498 (4) | C25—H25 | 0.9300 |
C9—C10 | 1.531 (4) | C26—C27 | 1.355 (5) |
C9—H9A | 0.9700 | C26—H26 | 0.9300 |
C9—H9B | 0.9700 | C27—C28 | 1.359 (5) |
C10—N3 | 1.485 (4) | C27—Cl1 | 1.747 (4) |
C10—C11 | 1.495 (4) | C28—C29 | 1.378 (5) |
C10—H10 | 0.9800 | C28—H28 | 0.9300 |
C11—C16 | 1.363 (4) | C29—H29 | 0.9300 |
C11—C12 | 1.370 (4) | C30—C31 | 1.252 (10) |
C12—C13 | 1.386 (5) | C30—O3 | 1.396 (8) |
C12—H12 | 0.9300 | C30—H30A | 0.9700 |
C13—C14 | 1.349 (5) | C30—H30B | 0.9700 |
C13—H13 | 0.9300 | C31—C32 | 1.452 (12) |
C14—C15 | 1.361 (5) | C31—H31A | 0.9700 |
C14—Cl2 | 1.738 (4) | C31—H31B | 0.9700 |
C15—C16 | 1.386 (5) | C32—C33 | 1.380 (13) |
C15—H15 | 0.9300 | C32—H32A | 0.9700 |
C16—H16 | 0.9300 | C32—H32B | 0.9700 |
C17—O1 | 1.226 (3) | C33—O3 | 1.328 (9) |
C17—N3 | 1.350 (4) | C33—H33A | 0.9700 |
C17—C18 | 1.493 (4) | C33—H33B | 0.9700 |
C18—H18A | 0.9600 | C4—H4A | 0.9300 |
C18—H18B | 0.9600 | N2—N3 | 1.389 (3) |
C18—H18C | 0.9600 | N4—N5 | 1.384 (3) |
C4—C1—C2 | 117.2 (2) | N5—C20—H20 | 109.5 |
C4—C1—C8 | 118.8 (2) | C24—C20—H20 | 109.5 |
C2—C1—C8 | 123.9 (3) | C21—C20—H20 | 109.5 |
N1—C2—C1 | 121.3 (3) | C19—C21—C20 | 103.3 (2) |
N1—C2—C3 | 113.9 (3) | C19—C21—H21A | 111.1 |
C1—C2—C3 | 124.7 (3) | C20—C21—H21A | 111.1 |
C2—C3—H3A | 109.5 | C19—C21—H21B | 111.1 |
C2—C3—H3B | 109.5 | C20—C21—H21B | 111.1 |
H3A—C3—H3B | 109.5 | H21A—C21—H21B | 109.1 |
C2—C3—H3C | 109.5 | O2—C22—N5 | 119.4 (3) |
H3A—C3—H3C | 109.5 | O2—C22—C23 | 124.3 (3) |
H3B—C3—H3C | 109.5 | N5—C22—C23 | 116.2 (3) |
C5—N1—C2 | 121.2 (2) | C22—C23—H23A | 109.5 |
N1—C5—C7 | 121.1 (2) | C22—C23—H23B | 109.5 |
N1—C5—C6 | 114.0 (3) | H23A—C23—H23B | 109.5 |
C7—C5—C6 | 124.9 (3) | C22—C23—H23C | 109.5 |
C5—C6—H6A | 109.5 | H23A—C23—H23C | 109.5 |
C5—C6—H6B | 109.5 | H23B—C23—H23C | 109.5 |
H6A—C6—H6B | 109.5 | C25—C24—C29 | 118.3 (3) |
C5—C6—H6C | 109.5 | C25—C24—C20 | 121.5 (3) |
H6A—C6—H6C | 109.5 | C29—C24—C20 | 120.2 (3) |
H6B—C6—H6C | 109.5 | C24—C25—C26 | 121.3 (3) |
C4—C7—C5 | 117.0 (3) | C24—C25—H25 | 119.4 |
C4—C7—C19 | 118.9 (3) | C26—C25—H25 | 119.4 |
C5—C7—C19 | 124.1 (2) | C27—C26—C25 | 118.8 (4) |
N2—C8—C1 | 122.9 (2) | C27—C26—H26 | 120.6 |
N2—C8—C9 | 113.8 (2) | C25—C26—H26 | 120.6 |
C1—C8—C9 | 123.3 (3) | C26—C27—C28 | 121.7 (4) |
C8—C9—C10 | 103.6 (2) | C26—C27—Cl1 | 119.5 (4) |
C8—C9—H9A | 111.0 | C28—C27—Cl1 | 118.8 (4) |
C10—C9—H9A | 111.0 | C27—C28—C29 | 119.2 (3) |
C8—C9—H9B | 111.0 | C27—C28—H28 | 120.4 |
C10—C9—H9B | 111.0 | C29—C28—H28 | 120.4 |
H9A—C9—H9B | 109.0 | C24—C29—C28 | 120.7 (4) |
N3—C10—C11 | 113.0 (2) | C24—C29—H29 | 119.7 |
N3—C10—C9 | 101.0 (2) | C28—C29—H29 | 119.7 |
C11—C10—C9 | 114.8 (3) | C31—C30—O3 | 104.8 (8) |
N3—C10—H10 | 109.2 | C31—C30—H30A | 110.8 |
C11—C10—H10 | 109.2 | O3—C30—H30A | 110.8 |
C9—C10—H10 | 109.2 | C31—C30—H30B | 110.8 |
C16—C11—C12 | 117.2 (3) | O3—C30—H30B | 110.8 |
C16—C11—C10 | 121.1 (3) | H30A—C30—H30B | 108.9 |
C12—C11—C10 | 121.7 (3) | C30—C31—C32 | 102.7 (8) |
C11—C12—C13 | 121.6 (3) | C30—C31—H31A | 111.2 |
C11—C12—H12 | 119.2 | C32—C31—H31A | 111.2 |
C13—C12—H12 | 119.2 | C30—C31—H31B | 111.2 |
C14—C13—C12 | 119.5 (3) | C32—C31—H31B | 111.2 |
C14—C13—H13 | 120.2 | H31A—C31—H31B | 109.1 |
C12—C13—H13 | 120.2 | C33—C32—C31 | 103.5 (8) |
C13—C14—C15 | 120.6 (3) | C33—C32—H32A | 111.1 |
C13—C14—Cl2 | 119.8 (3) | C31—C32—H32A | 111.1 |
C15—C14—Cl2 | 119.6 (3) | C33—C32—H32B | 111.1 |
C14—C15—C16 | 118.9 (3) | C31—C32—H32B | 111.1 |
C14—C15—H15 | 120.5 | H32A—C32—H32B | 109.0 |
C16—C15—H15 | 120.5 | O3—C33—C32 | 93.9 (7) |
C11—C16—C15 | 122.2 (3) | O3—C33—H33A | 113.0 |
C11—C16—H16 | 118.9 | C32—C33—H33A | 113.0 |
C15—C16—H16 | 118.9 | O3—C33—H33B | 113.0 |
O1—C17—N3 | 119.2 (3) | C32—C33—H33B | 113.0 |
O1—C17—C18 | 123.2 (3) | H33A—C33—H33B | 110.4 |
N3—C17—C18 | 117.6 (3) | C1—C4—C7 | 122.1 (3) |
C17—C18—H18A | 109.5 | C1—C4—H4A | 119.0 |
C17—C18—H18B | 109.5 | C7—C4—H4A | 119.0 |
H18A—C18—H18B | 109.5 | C8—N2—N3 | 108.5 (2) |
C17—C18—H18C | 109.5 | C17—N3—N2 | 121.8 (2) |
H18A—C18—H18C | 109.5 | C17—N3—C10 | 124.5 (3) |
H18B—C18—H18C | 109.5 | N2—N3—C10 | 113.0 (2) |
N4—C19—C7 | 122.2 (3) | C19—N4—N5 | 109.4 (2) |
N4—C19—C21 | 113.0 (3) | C22—N5—N4 | 120.6 (3) |
C7—C19—C21 | 124.8 (2) | C22—N5—C20 | 124.7 (3) |
N5—C20—C24 | 111.6 (3) | N4—N5—C20 | 113.3 (2) |
N5—C20—C21 | 100.6 (2) | C33—O3—C30 | 100.0 (7) |
C24—C20—C21 | 115.8 (3) | ||
C4—C1—C2—N1 | 0.7 (4) | C21—C20—C24—C29 | −127.4 (3) |
C8—C1—C2—N1 | −176.9 (3) | C29—C24—C25—C26 | −1.4 (5) |
C4—C1—C2—C3 | 179.5 (3) | C20—C24—C25—C26 | 177.1 (3) |
C8—C1—C2—C3 | 1.9 (5) | C24—C25—C26—C27 | 0.1 (6) |
C1—C2—N1—C5 | −0.6 (4) | C25—C26—C27—C28 | 1.6 (6) |
C3—C2—N1—C5 | −179.6 (3) | C25—C26—C27—Cl1 | −177.6 (3) |
C2—N1—C5—C7 | −0.4 (4) | C26—C27—C28—C29 | −1.9 (6) |
C2—N1—C5—C6 | 179.4 (3) | Cl1—C27—C28—C29 | 177.3 (3) |
N1—C5—C7—C4 | 1.2 (4) | C25—C24—C29—C28 | 1.1 (5) |
C6—C5—C7—C4 | −178.5 (3) | C20—C24—C29—C28 | −177.5 (3) |
N1—C5—C7—C19 | −178.3 (3) | C27—C28—C29—C24 | 0.5 (6) |
C6—C5—C7—C19 | 2.0 (5) | O3—C30—C31—C32 | −18.4 (14) |
C4—C1—C8—N2 | 167.5 (3) | C30—C31—C32—C33 | −17.0 (16) |
C2—C1—C8—N2 | −14.9 (4) | C31—C32—C33—O3 | 45.8 (12) |
C4—C1—C8—C9 | −13.4 (4) | C2—C1—C4—C7 | 0.2 (4) |
C2—C1—C8—C9 | 164.2 (3) | C8—C1—C4—C7 | 178.0 (2) |
N2—C8—C9—C10 | −2.2 (4) | C5—C7—C4—C1 | −1.1 (4) |
C1—C8—C9—C10 | 178.7 (3) | C19—C7—C4—C1 | 178.4 (2) |
C8—C9—C10—N3 | 2.6 (3) | C1—C8—N2—N3 | 179.7 (2) |
C8—C9—C10—C11 | −119.2 (3) | C9—C8—N2—N3 | 0.6 (3) |
N3—C10—C11—C16 | −49.3 (4) | O1—C17—N3—N2 | 175.8 (3) |
C9—C10—C11—C16 | 65.7 (4) | C18—C17—N3—N2 | −3.2 (4) |
N3—C10—C11—C12 | 130.7 (3) | O1—C17—N3—C10 | 6.3 (5) |
C9—C10—C11—C12 | −114.2 (3) | C18—C17—N3—C10 | −172.7 (3) |
C16—C11—C12—C13 | 0.4 (5) | C8—N2—N3—C17 | −169.2 (3) |
C10—C11—C12—C13 | −179.7 (3) | C8—N2—N3—C10 | 1.4 (3) |
C11—C12—C13—C14 | 0.1 (6) | C11—C10—N3—C17 | −69.2 (4) |
C12—C13—C14—C15 | −0.8 (6) | C9—C10—N3—C17 | 167.7 (3) |
C12—C13—C14—Cl2 | 178.1 (3) | C11—C10—N3—N2 | 120.5 (3) |
C13—C14—C15—C16 | 1.0 (5) | C9—C10—N3—N2 | −2.6 (3) |
Cl2—C14—C15—C16 | −177.8 (3) | C7—C19—N4—N5 | 178.8 (2) |
C12—C11—C16—C15 | −0.1 (5) | C21—C19—N4—N5 | −1.0 (4) |
C10—C11—C16—C15 | 179.9 (3) | O2—C22—N5—N4 | 168.8 (3) |
C14—C15—C16—C11 | −0.6 (5) | C23—C22—N5—N4 | −14.0 (5) |
C4—C7—C19—N4 | 177.9 (3) | O2—C22—N5—C20 | 3.5 (6) |
C5—C7—C19—N4 | −2.6 (4) | C23—C22—N5—C20 | −179.3 (3) |
C4—C7—C19—C21 | −2.4 (4) | C19—N4—N5—C22 | −170.4 (3) |
C5—C7—C19—C21 | 177.1 (3) | C19—N4—N5—C20 | −3.6 (3) |
N4—C19—C21—C20 | 4.7 (4) | C24—C20—N5—C22 | −64.2 (4) |
C7—C19—C21—C20 | −175.0 (3) | C21—C20—N5—C22 | 172.4 (3) |
N5—C20—C21—C19 | −6.0 (3) | C24—C20—N5—N4 | 129.5 (3) |
C24—C20—C21—C19 | −126.5 (3) | C21—C20—N5—N4 | 6.1 (3) |
N5—C20—C24—C25 | −60.2 (4) | C32—C33—O3—C30 | −56.7 (11) |
C21—C20—C24—C25 | 54.1 (4) | C31—C30—O3—C33 | 50.4 (13) |
N5—C20—C24—C29 | 118.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9B···O3 | 0.97 | 2.49 | 3.423 (7) | 163 |
C21—H21B···O1i | 0.97 | 2.57 | 3.211 (4) | 123 |
C9—H9A···O1i | 0.97 | 2.35 | 3.234 (4) | 151 |
C23—H23A···O2ii | 0.96 | 2.45 | 3.385 (4) | 166 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+2, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | C29H27Cl2N5O2·C4H8O |
Mr | 620.56 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 16.888 (3), 11.180 (2), 17.313 (4) |
β (°) | 98.69 (3) |
V (Å3) | 3231.5 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.20 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.953, 0.976 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16422, 5715, 2714 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.171, 0.95 |
No. of reflections | 5715 |
No. of parameters | 393 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.36 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9B···O3 | 0.97 | 2.49 | 3.423 (7) | 162.5 |
C21—H21B···O1i | 0.97 | 2.57 | 3.211 (4) | 123.4 |
C9—H9A···O1i | 0.97 | 2.35 | 3.234 (4) | 150.6 |
C23—H23A···O2ii | 0.96 | 2.45 | 3.385 (4) | 165.5 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+2, −y+2, −z. |
Nitrogen-containing heterocycles compounds are well known natural products moieties which present interesting biological activities and pharmacological properties (Holla et al., 2002; Soudi et al., 2005). For example, 1,3,5-trisubstitituted pyrazolines show reversible and selective monoamine oxidase inhibitory properties. Their selective biological activity is in part due to the influence of substitution on the compounds conformation (Palaska et al., 1996). These useful applications for the 1,3,5-trisubstituted pyrazolines attracted our attention and we present here a new member of this family.
The molecular structure of (I) consists of one polycyclic molecule and one tetrahydrofuran solvent molecule (Fig. 1). There are two substituted phenyl rings bonded with two different pyrazoline rings, and these two pyrazoline rings are further bonded with one central pyridine ring. The dihedral angles between the pyridine plane and the two pyrazoline planes are 5.10 and 13.99°. Each substituted phenyl plane is nearly normal to the corresponding pyrazoline plane, with dihedral angles of 88.04 and 83.38°. Bond lengths in the pyrazoline rings and substituted phenyl rings are in good agreement with those found in similar compounds (e.g. Chopra et al., 2006).
In the crystal structure, there are three types of intermolecular and one intramolecular hydrogen bonds, which make the crystal structure to be more stable (see hydrogen-bond geometry Table).