Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030504/hb2376sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030504/hb2376Isup2.hkl |
CCDC reference: 657686
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.002 Å
- Disorder in main residue
- R factor = 0.040
- wR factor = 0.113
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT213_ALERT_2_C Atom O1A has ADP max/min Ratio ............. 3.30 prola PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3 PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 4.40 Deg. O1A -N3 -O1B 1.555 1.555 1.555
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C11 = ... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A mixture of 1-aryl-3-(3,4-dimethoxy -6-nitrophenyl) -2-propene-1-ones (0.01 mol) and phenylhydrazine (0.01 mol) in glacial acetic acid (5 ml) was taken in a conical flask and irradiated in a microwave oven for 5 minutes. The resultant solution was poured into a beaker containing crushed ice and the solid separated was collected by filtration, washed with water, dried and recrystallized from formacetic acid. Red blocks of (I) were grown from ethanol by slow evaporation at room temperature.
The O atoms of the nitro group are disordered over two sites in a 0.68 (2):0.32 (2) ratio (sum constrained to unity). All the H atoms were fixed geometrically (C—H = 0.93=0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(carrier).
Five- and six-membered heterocyclic compounds are important constituents that often exist in biologically active natural products and synthetic compounds of medicinal interest (Gilchrist, 1998). In this series, 1,3,5–trisubstituted pyrazolines, prepared from phenylhydrazine and chalcone derivatives (Nakamichi et al., 2002) have been used as antitumour (Taylor et al., 1992) agents. Here we report the structure of the title compound, (I), a new derivative of pyrazoline.
In the pyrazoline ring (Fig. 1), the C12═N2 [1.287 (3) Å] and N1—N2 [1.382 (3) Å] bond lengths are shorter than those found in similar structures reported by Rurack et al. (2000) and Ge (2006). [C═N = 1.291 (2) Å, 1.293 (3)Å and N—N = 1.394 (3) Å, 1.384 (2)Å respectively]. The C3—C11—N1—C18 torsion angle in (I) of 85.48 (16)° indicates a gauche conformation for the substituents. The pyrazoline ring shows a slightly distorted envelope conformation with C9 deviating by 0.036 (3)Å from the plane of C10, C11, N1 and N2. The dihedral angle between the pyrazoline ring and the 3–phenyl ring is 4.6 (1)°, marking their near co-planarity with a maximum deviation of 0.068 (3)Å for atom C(17). The 5–phenyl ring is almost perpendicular to the pyrazoline ring as the dihedral angle between them is 75.4 (1)°.
The molecular packing is stabilized by weak C—H···O and C—H···N interactions (Table 1, Fig. 2).
For related literature, see: Gilchrist (1998); Nakamichi et al. (2002); Rurack et al. (2000); Taylor et al. (1992); Ge (2006).
Data collection: APEX (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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).
Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids (arbitrary spheres for the H atoms). | |
Fig. 2. Hydrogen bonding interactions in (I) shown as dashed lines. |
C23H21N3O4 | F(000) = 1696 |
Mr = 403.43 | Dx = 1.292 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 55 reflections |
a = 36.0919 (7) Å | θ = 5–11° |
b = 13.4372 (1) Å | µ = 0.09 mm−1 |
c = 8.8190 (2) Å | T = 296 K |
β = 104.099 (1)° | Block, red |
V = 4148.15 (13) Å3 | 0.35 × 0.30 × 0.20 mm |
Z = 8 |
Bruker SMART CCD diffractometer | Rint = 0.033 |
ω scans | θmax = 25.3°, θmin = 1.2° |
9555 measured reflections | h = −42→31 |
3721 independent reflections | k = −16→16 |
2605 reflections with I > 2σ(I) | l = −7→10 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.040 | w = 1/[σ2(Fo2) + (0.0637P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.114 | (Δ/σ)max < 0.001 |
S = 0.99 | Δρmax = 0.10 e Å−3 |
3721 reflections | Δρmin = −0.16 e Å−3 |
292 parameters |
C23H21N3O4 | V = 4148.15 (13) Å3 |
Mr = 403.43 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 36.0919 (7) Å | µ = 0.09 mm−1 |
b = 13.4372 (1) Å | T = 296 K |
c = 8.8190 (2) Å | 0.35 × 0.30 × 0.20 mm |
β = 104.099 (1)° |
Bruker SMART CCD diffractometer | 2605 reflections with I > 2σ(I) |
9555 measured reflections | Rint = 0.033 |
3721 independent reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.10 e Å−3 |
3721 reflections | Δρmin = −0.16 e Å−3 |
292 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) | |
C1 | 0.04766 (4) | 0.15292 (14) | 0.6636 (2) | 0.0745 (5) | |
H1 | 0.0341 | 0.0973 | 0.618 | 0.089* | |
C2 | 0.08305 (4) | 0.14080 (11) | 0.77009 (19) | 0.0653 (4) | |
C3 | 0.10437 (4) | 0.22122 (10) | 0.84411 (16) | 0.0522 (4) | |
C4 | 0.08773 (4) | 0.31481 (11) | 0.80876 (17) | 0.0559 (4) | |
H4 | 0.1005 | 0.3702 | 0.8592 | 0.067* | |
C5 | 0.05307 (4) | 0.32859 (12) | 0.70193 (18) | 0.0627 (4) | |
C6 | 0.03303 (4) | 0.24523 (13) | 0.62634 (19) | 0.0674 (4) | |
C7 | −0.02062 (5) | 0.1837 (2) | 0.4375 (3) | 0.1142 (8) | |
H7A | −0.0045 | 0.1479 | 0.3845 | 0.171* | |
H7B | −0.0428 | 0.2074 | 0.3624 | 0.171* | |
H7C | −0.0284 | 0.1403 | 0.5105 | 0.171* | |
C8 | 0.05319 (6) | 0.50507 (15) | 0.7358 (3) | 0.1170 (8) | |
H8A | 0.0543 | 0.5001 | 0.8453 | 0.175* | |
H8B | 0.0382 | 0.562 | 0.6928 | 0.175* | |
H8C | 0.0786 | 0.5122 | 0.7216 | 0.175* | |
C9 | 0.17542 (4) | 0.21164 (10) | 0.85409 (18) | 0.0570 (4) | |
H9A | 0.192 | 0.1543 | 0.8812 | 0.068* | |
H9B | 0.1639 | 0.211 | 0.7426 | 0.068* | |
C10 | 0.19683 (4) | 0.30695 (10) | 0.90319 (16) | 0.0500 (3) | |
C11 | 0.14472 (4) | 0.21363 (10) | 0.94876 (17) | 0.0528 (4) | |
H11 | 0.147 | 0.1544 | 1.0152 | 0.063* | |
C12 | 0.22849 (4) | 0.34477 (11) | 0.84239 (16) | 0.0528 (4) | |
C13 | 0.24274 (4) | 0.28957 (13) | 0.73612 (19) | 0.0665 (4) | |
H13 | 0.2315 | 0.2289 | 0.7005 | 0.08* | |
C14 | 0.27354 (5) | 0.32351 (14) | 0.6821 (2) | 0.0749 (5) | |
H14 | 0.2829 | 0.2853 | 0.6117 | 0.09* | |
C15 | 0.29022 (5) | 0.41318 (14) | 0.7324 (2) | 0.0753 (5) | |
H15 | 0.3108 | 0.436 | 0.6962 | 0.09* | |
C16 | 0.27623 (5) | 0.46919 (13) | 0.8368 (2) | 0.0729 (5) | |
H16 | 0.2874 | 0.5303 | 0.8702 | 0.087* | |
C17 | 0.24589 (4) | 0.43598 (12) | 0.89252 (18) | 0.0618 (4) | |
H17 | 0.237 | 0.4744 | 0.9638 | 0.074* | |
C18 | 0.14669 (4) | 0.31886 (10) | 1.18989 (16) | 0.0489 (3) | |
C19 | 0.16297 (4) | 0.39793 (11) | 1.28447 (17) | 0.0588 (4) | |
H19 | 0.1795 | 0.4413 | 1.2512 | 0.071* | |
C20 | 0.15472 (5) | 0.41225 (13) | 1.42746 (18) | 0.0712 (5) | |
H20 | 0.1659 | 0.4651 | 1.4903 | 0.085* | |
C21 | 0.13019 (5) | 0.34949 (13) | 1.4787 (2) | 0.0769 (5) | |
H21 | 0.1245 | 0.3601 | 1.5748 | 0.092* | |
C22 | 0.11419 (5) | 0.27102 (14) | 1.3861 (2) | 0.0749 (5) | |
H22 | 0.0978 | 0.2279 | 1.4206 | 0.09* | |
C23 | 0.12210 (4) | 0.25515 (12) | 1.24222 (19) | 0.0640 (4) | |
H23 | 0.111 | 0.2018 | 1.1805 | 0.077* | |
N1 | 0.15523 (3) | 0.30319 (9) | 1.04577 (13) | 0.0530 (3) | |
N2 | 0.18567 (3) | 0.35337 (8) | 1.01177 (13) | 0.0512 (3) | |
N3 | 0.09614 (6) | 0.03865 (13) | 0.8015 (3) | 0.1039 (6) | |
O1A | 0.1226 (6) | 0.0251 (11) | 0.856 (2) | 0.217 (11) | 0.32 (2) |
O2A | 0.0810 (7) | −0.0219 (9) | 0.692 (3) | 0.150 (9) | 0.32 (2) |
O1B | 0.13056 (17) | 0.0181 (4) | 0.8620 (6) | 0.0994 (18) | 0.68 (2) |
O2B | 0.07079 (11) | −0.0280 (3) | 0.7954 (18) | 0.133 (3) | 0.68 (2) |
O3 | −0.00013 (3) | 0.26599 (10) | 0.51909 (15) | 0.0943 (4) | |
O4 | 0.03612 (3) | 0.41708 (9) | 0.65777 (15) | 0.0895 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0562 (9) | 0.0791 (12) | 0.0831 (12) | −0.0132 (9) | 0.0070 (8) | −0.0252 (9) |
C2 | 0.0544 (9) | 0.0571 (10) | 0.0805 (11) | −0.0057 (7) | 0.0090 (8) | −0.0163 (8) |
C3 | 0.0465 (7) | 0.0560 (9) | 0.0544 (8) | −0.0053 (7) | 0.0128 (6) | −0.0076 (6) |
C4 | 0.0499 (8) | 0.0585 (9) | 0.0583 (9) | −0.0052 (7) | 0.0116 (7) | −0.0080 (7) |
C5 | 0.0521 (9) | 0.0721 (10) | 0.0634 (9) | 0.0034 (8) | 0.0128 (7) | −0.0007 (8) |
C6 | 0.0439 (8) | 0.0927 (13) | 0.0627 (9) | −0.0030 (8) | 0.0078 (7) | −0.0117 (9) |
C7 | 0.0633 (11) | 0.171 (2) | 0.0927 (15) | −0.0215 (13) | −0.0106 (10) | −0.0300 (15) |
C8 | 0.1029 (16) | 0.0712 (13) | 0.158 (2) | 0.0177 (12) | −0.0050 (15) | −0.0059 (14) |
C9 | 0.0481 (8) | 0.0579 (9) | 0.0623 (9) | 0.0015 (6) | 0.0082 (7) | −0.0064 (7) |
C10 | 0.0467 (7) | 0.0532 (8) | 0.0468 (8) | 0.0045 (6) | 0.0048 (6) | 0.0021 (6) |
C11 | 0.0497 (7) | 0.0487 (8) | 0.0570 (8) | −0.0034 (6) | 0.0069 (6) | −0.0037 (6) |
C12 | 0.0458 (7) | 0.0607 (9) | 0.0486 (8) | 0.0045 (6) | 0.0051 (6) | 0.0070 (7) |
C13 | 0.0605 (9) | 0.0757 (11) | 0.0636 (10) | 0.0038 (8) | 0.0158 (8) | −0.0013 (8) |
C14 | 0.0638 (10) | 0.0997 (13) | 0.0652 (10) | 0.0148 (10) | 0.0236 (8) | 0.0080 (9) |
C15 | 0.0552 (9) | 0.0993 (14) | 0.0731 (11) | 0.0025 (9) | 0.0192 (8) | 0.0248 (10) |
C16 | 0.0645 (10) | 0.0762 (11) | 0.0779 (11) | −0.0064 (8) | 0.0171 (9) | 0.0142 (9) |
C17 | 0.0572 (9) | 0.0654 (10) | 0.0624 (9) | −0.0007 (7) | 0.0138 (7) | 0.0054 (7) |
C18 | 0.0444 (7) | 0.0515 (8) | 0.0492 (8) | 0.0016 (6) | 0.0084 (6) | 0.0038 (6) |
C19 | 0.0679 (9) | 0.0545 (9) | 0.0550 (8) | −0.0081 (7) | 0.0165 (7) | −0.0002 (7) |
C20 | 0.0940 (12) | 0.0650 (10) | 0.0565 (9) | −0.0043 (9) | 0.0218 (9) | −0.0042 (8) |
C21 | 0.0960 (13) | 0.0823 (12) | 0.0604 (10) | 0.0022 (10) | 0.0344 (9) | 0.0049 (9) |
C22 | 0.0743 (11) | 0.0834 (12) | 0.0750 (11) | −0.0091 (9) | 0.0334 (9) | 0.0107 (9) |
C23 | 0.0586 (9) | 0.0666 (10) | 0.0681 (10) | −0.0126 (7) | 0.0181 (8) | −0.0028 (8) |
N1 | 0.0488 (6) | 0.0571 (7) | 0.0529 (7) | −0.0123 (5) | 0.0121 (5) | −0.0067 (5) |
N2 | 0.0488 (6) | 0.0538 (7) | 0.0490 (6) | −0.0051 (5) | 0.0081 (5) | 0.0020 (5) |
N3 | 0.0774 (12) | 0.0602 (11) | 0.1527 (17) | −0.0077 (10) | −0.0133 (11) | −0.0300 (11) |
O1A | 0.116 (9) | 0.062 (5) | 0.39 (2) | 0.029 (6) | −0.092 (11) | −0.055 (7) |
O2A | 0.157 (9) | 0.057 (4) | 0.189 (14) | −0.003 (4) | −0.046 (10) | −0.039 (6) |
O1B | 0.059 (2) | 0.067 (2) | 0.159 (4) | 0.0116 (14) | −0.001 (2) | −0.0281 (18) |
O2B | 0.100 (2) | 0.0738 (17) | 0.202 (7) | −0.0342 (14) | −0.010 (3) | −0.005 (2) |
O3 | 0.0558 (7) | 0.1252 (11) | 0.0873 (9) | −0.0017 (7) | −0.0105 (6) | −0.0107 (8) |
O4 | 0.0699 (7) | 0.0812 (9) | 0.1052 (10) | 0.0147 (7) | −0.0018 (7) | 0.0063 (7) |
C1—C6 | 1.357 (2) | C12—C17 | 1.399 (2) |
C1—C2 | 1.399 (2) | C13—C14 | 1.389 (2) |
C1—H1 | 0.93 | C13—H13 | 0.93 |
C2—C3 | 1.3933 (19) | C14—C15 | 1.371 (2) |
C2—N3 | 1.456 (2) | C14—H14 | 0.93 |
C3—C4 | 1.396 (2) | C15—C16 | 1.377 (2) |
C3—C11 | 1.5258 (19) | C15—H15 | 0.93 |
C4—C5 | 1.383 (2) | C16—C17 | 1.379 (2) |
C4—H4 | 0.93 | C16—H16 | 0.93 |
C5—O4 | 1.3505 (19) | C17—H17 | 0.93 |
C5—C6 | 1.410 (2) | C18—C19 | 1.3897 (19) |
C6—O3 | 1.361 (2) | C18—C23 | 1.3902 (19) |
C7—O3 | 1.424 (2) | C18—N1 | 1.3949 (17) |
C7—H7A | 0.96 | C19—C20 | 1.378 (2) |
C7—H7B | 0.96 | C19—H19 | 0.93 |
C7—H7C | 0.96 | C20—C21 | 1.376 (2) |
C8—O4 | 1.430 (2) | C20—H20 | 0.93 |
C8—H8A | 0.96 | C21—C22 | 1.372 (2) |
C8—H8B | 0.96 | C21—H21 | 0.93 |
C8—H8C | 0.96 | C22—C23 | 1.384 (2) |
C9—C10 | 1.5040 (19) | C22—H22 | 0.93 |
C9—C11 | 1.541 (2) | C23—H23 | 0.93 |
C9—H9A | 0.97 | N1—N2 | 1.3829 (15) |
C9—H9B | 0.97 | N3—O1A | 0.98 (2) |
C10—N2 | 1.2867 (17) | N3—O1B | 1.257 (7) |
C10—C12 | 1.467 (2) | N3—O2B | 1.272 (4) |
C11—N1 | 1.4717 (17) | N3—O2A | 1.282 (10) |
C11—H11 | 0.98 | O2A—O2B | 1.07 (3) |
C12—C13 | 1.388 (2) | ||
C6—C1—C2 | 120.45 (15) | C14—C13—H13 | 119.5 |
C6—C1—H1 | 119.8 | C15—C14—C13 | 120.18 (16) |
C2—C1—H1 | 119.8 | C15—C14—H14 | 119.9 |
C3—C2—C1 | 122.30 (15) | C13—C14—H14 | 119.9 |
C3—C2—N3 | 121.69 (14) | C14—C15—C16 | 119.55 (16) |
C1—C2—N3 | 116.00 (14) | C14—C15—H15 | 120.2 |
C2—C3—C4 | 115.82 (13) | C16—C15—H15 | 120.2 |
C2—C3—C11 | 124.64 (13) | C15—C16—C17 | 120.90 (17) |
C4—C3—C11 | 119.39 (12) | C15—C16—H16 | 119.5 |
C5—C4—C3 | 122.78 (13) | C17—C16—H16 | 119.5 |
C5—C4—H4 | 118.6 | C16—C17—C12 | 120.35 (15) |
C3—C4—H4 | 118.6 | C16—C17—H17 | 119.8 |
O4—C5—C4 | 125.83 (14) | C12—C17—H17 | 119.8 |
O4—C5—C6 | 114.77 (14) | C19—C18—C23 | 118.84 (13) |
C4—C5—C6 | 119.38 (15) | C19—C18—N1 | 120.48 (12) |
C1—C6—O3 | 125.44 (15) | C23—C18—N1 | 120.68 (13) |
C1—C6—C5 | 119.17 (14) | C20—C19—C18 | 120.12 (14) |
O3—C6—C5 | 115.39 (15) | C20—C19—H19 | 119.9 |
O3—C7—H7A | 109.5 | C18—C19—H19 | 119.9 |
O3—C7—H7B | 109.5 | C21—C20—C19 | 120.98 (16) |
H7A—C7—H7B | 109.5 | C21—C20—H20 | 119.5 |
O3—C7—H7C | 109.5 | C19—C20—H20 | 119.5 |
H7A—C7—H7C | 109.5 | C22—C21—C20 | 119.12 (15) |
H7B—C7—H7C | 109.5 | C22—C21—H21 | 120.4 |
O4—C8—H8A | 109.5 | C20—C21—H21 | 120.4 |
O4—C8—H8B | 109.5 | C21—C22—C23 | 120.89 (15) |
H8A—C8—H8B | 109.5 | C21—C22—H22 | 119.6 |
O4—C8—H8C | 109.5 | C23—C22—H22 | 119.6 |
H8A—C8—H8C | 109.5 | C22—C23—C18 | 120.04 (15) |
H8B—C8—H8C | 109.5 | C22—C23—H23 | 120 |
C10—C9—C11 | 102.46 (11) | C18—C23—H23 | 120 |
C10—C9—H9A | 111.3 | N2—N1—C18 | 119.19 (11) |
C11—C9—H9A | 111.3 | N2—N1—C11 | 112.24 (10) |
C10—C9—H9B | 111.3 | C18—N1—C11 | 124.77 (11) |
C11—C9—H9B | 111.3 | C10—N2—N1 | 109.52 (11) |
H9A—C9—H9B | 109.2 | O1A—N3—O1B | 4.4 (13) |
N2—C10—C12 | 121.14 (13) | O1A—N3—O2B | 119.9 (10) |
N2—C10—C9 | 113.28 (12) | O1B—N3—O2B | 119.3 (4) |
C12—C10—C9 | 125.54 (13) | O1A—N3—O2A | 116.1 (10) |
N1—C11—C3 | 111.70 (11) | O1B—N3—O2A | 112.2 (8) |
N1—C11—C9 | 102.22 (10) | O2B—N3—O2A | 49.5 (12) |
C3—C11—C9 | 112.31 (12) | O1A—N3—C2 | 120.1 (9) |
N1—C11—H11 | 110.1 | O1B—N3—C2 | 121.9 (3) |
C3—C11—H11 | 110.1 | O2B—N3—C2 | 117.3 (2) |
C9—C11—H11 | 110.1 | O2A—N3—C2 | 113.3 (6) |
C13—C12—C17 | 118.03 (14) | O2B—O2A—N3 | 64.7 (11) |
C13—C12—C10 | 120.76 (14) | O2A—O2B—N3 | 65.7 (5) |
C17—C12—C10 | 121.19 (13) | C6—O3—C7 | 116.90 (16) |
C12—C13—C14 | 120.99 (16) | C5—O4—C8 | 118.52 (14) |
C12—C13—H13 | 119.5 | ||
C6—C1—C2—C3 | 1.2 (3) | N1—C18—C19—C20 | −179.27 (13) |
C6—C1—C2—N3 | −179.87 (17) | C18—C19—C20—C21 | −0.4 (2) |
C1—C2—C3—C4 | 1.7 (2) | C19—C20—C21—C22 | 0.8 (3) |
N3—C2—C3—C4 | −177.18 (15) | C20—C21—C22—C23 | −0.7 (3) |
C1—C2—C3—C11 | −173.75 (14) | C21—C22—C23—C18 | 0.3 (3) |
N3—C2—C3—C11 | 7.3 (3) | C19—C18—C23—C22 | 0.0 (2) |
C2—C3—C4—C5 | −2.8 (2) | N1—C18—C23—C22 | 179.35 (14) |
C11—C3—C4—C5 | 172.92 (13) | C19—C18—N1—N2 | 13.30 (19) |
C3—C4—C5—O4 | −177.22 (14) | C23—C18—N1—N2 | −165.99 (12) |
C3—C4—C5—C6 | 1.0 (2) | C19—C18—N1—C11 | 169.58 (13) |
C2—C1—C6—O3 | 176.69 (16) | C23—C18—N1—C11 | −9.7 (2) |
C2—C1—C6—C5 | −3.0 (3) | C3—C11—N1—N2 | −116.82 (12) |
O4—C5—C6—C1 | −179.59 (15) | C9—C11—N1—N2 | 3.46 (14) |
C4—C5—C6—C1 | 2.0 (2) | C3—C11—N1—C18 | 85.48 (16) |
O4—C5—C6—O3 | 0.7 (2) | C9—C11—N1—C18 | −154.24 (12) |
C4—C5—C6—O3 | −177.77 (14) | C12—C10—N2—N1 | 179.09 (11) |
C11—C9—C10—N2 | 5.23 (15) | C9—C10—N2—N1 | −3.25 (16) |
C11—C9—C10—C12 | −177.23 (12) | C18—N1—N2—C10 | 158.75 (11) |
C2—C3—C11—N1 | −163.01 (14) | C11—N1—N2—C10 | −0.33 (15) |
C4—C3—C11—N1 | 21.66 (18) | C3—C2—N3—O1A | −14.5 (15) |
C2—C3—C11—C9 | 82.81 (18) | C1—C2—N3—O1A | 166.5 (15) |
C4—C3—C11—C9 | −92.52 (15) | C3—C2—N3—O1B | −19.2 (4) |
C10—C9—C11—N1 | −4.77 (13) | C1—C2—N3—O1B | 161.9 (3) |
C10—C9—C11—C3 | 115.09 (12) | C3—C2—N3—O2B | 147.0 (8) |
N2—C10—C12—C13 | 173.82 (13) | C1—C2—N3—O2B | −31.9 (9) |
C9—C10—C12—C13 | −3.5 (2) | C3—C2—N3—O2A | −158 (2) |
N2—C10—C12—C17 | −4.5 (2) | C1—C2—N3—O2A | 23 (2) |
C9—C10—C12—C17 | 178.15 (13) | O1A—N3—O2A—O2B | 108.2 (15) |
C17—C12—C13—C14 | 0.5 (2) | O1B—N3—O2A—O2B | 110.4 (10) |
C10—C12—C13—C14 | −177.84 (13) | C2—N3—O2A—O2B | −106.8 (8) |
C12—C13—C14—C15 | −0.6 (2) | O1A—N3—O2B—O2A | −100.1 (14) |
C13—C14—C15—C16 | 0.1 (2) | O1B—N3—O2B—O2A | −95.1 (9) |
C14—C15—C16—C17 | 0.5 (2) | C2—N3—O2B—O2A | 98.3 (7) |
C15—C16—C17—C12 | −0.6 (2) | C1—C6—O3—C7 | −1.3 (3) |
C13—C12—C17—C16 | 0.1 (2) | C5—C6—O3—C7 | 178.40 (16) |
C10—C12—C17—C16 | 178.44 (13) | C4—C5—O4—C8 | −5.7 (3) |
C23—C18—C19—C20 | 0.0 (2) | C6—C5—O4—C8 | 175.99 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···O1Bi | 0.93 | 2.55 | 3.467 (6) | 170 |
C20—H20···N2ii | 0.93 | 2.54 | 3.364 (2) | 149 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) x, −y+1, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C23H21N3O4 |
Mr | 403.43 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 296 |
a, b, c (Å) | 36.0919 (7), 13.4372 (1), 8.8190 (2) |
β (°) | 104.099 (1) |
V (Å3) | 4148.15 (13) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.35 × 0.30 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9555, 3721, 2605 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.114, 0.99 |
No. of reflections | 3721 |
No. of parameters | 292 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.10, −0.16 |
Computer programs: APEX (Bruker, 2000), SAINT (Bruker, 2000), SAINT, 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 |
C15—H15···O1Bi | 0.93 | 2.55 | 3.467 (6) | 170 |
C20—H20···N2ii | 0.93 | 2.54 | 3.364 (2) | 149 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) x, −y+1, z+1/2. |
Five- and six-membered heterocyclic compounds are important constituents that often exist in biologically active natural products and synthetic compounds of medicinal interest (Gilchrist, 1998). In this series, 1,3,5–trisubstituted pyrazolines, prepared from phenylhydrazine and chalcone derivatives (Nakamichi et al., 2002) have been used as antitumour (Taylor et al., 1992) agents. Here we report the structure of the title compound, (I), a new derivative of pyrazoline.
In the pyrazoline ring (Fig. 1), the C12═N2 [1.287 (3) Å] and N1—N2 [1.382 (3) Å] bond lengths are shorter than those found in similar structures reported by Rurack et al. (2000) and Ge (2006). [C═N = 1.291 (2) Å, 1.293 (3)Å and N—N = 1.394 (3) Å, 1.384 (2)Å respectively]. The C3—C11—N1—C18 torsion angle in (I) of 85.48 (16)° indicates a gauche conformation for the substituents. The pyrazoline ring shows a slightly distorted envelope conformation with C9 deviating by 0.036 (3)Å from the plane of C10, C11, N1 and N2. The dihedral angle between the pyrazoline ring and the 3–phenyl ring is 4.6 (1)°, marking their near co-planarity with a maximum deviation of 0.068 (3)Å for atom C(17). The 5–phenyl ring is almost perpendicular to the pyrazoline ring as the dihedral angle between them is 75.4 (1)°.
The molecular packing is stabilized by weak C—H···O and C—H···N interactions (Table 1, Fig. 2).