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In the title compound, C29H27Cl2N5O2·C4H8O, the polycyclic system is composed of three parts: one central pyridine ring substituted by two functionalized pyrazoline rings. The dihedral angles between the central pyridine plane and pyrazoline planes are 5.11 (1) and 13.99 (1)°, whereas the dihedral angles between each chloro­phenyl plane and the attached pyrazoline planes are 88.65 (1) and 83.87 (1)°. Mol­ecules are linked by inter­molecular C—H...O hydrogen bonds, forming a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808018497/bh2175sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536808018497/bh2175Isup2.hkl
Contains datablock I

CCDC reference: 696592

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Comment top

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).

Related literature top

For related literature, see: Holla et al. (2002); Palaska et al. (1996); Soudi et al. (2005); Chopra et al.(2006).

Experimental top

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.

Refinement top

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.

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 15% probability level.
[Figure 2] Fig. 2. Crystal packing diagram of compound (I). Hydrogen bonds are indicated by dashed lines.
3,5-Bis[1-acetyl-5-(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-3-yl]-2,6-dimethylpyridine tetrahydrofuran solvate top
Crystal data top
C29H27Cl2N5O2·C4H8OF(000) = 1304
Mr = 620.56Dx = 1.276 Mg m3
Monoclinic, P21/cMelting point = 489–491 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 16.888 (3) Åθ = 2.2–20.8°
b = 11.180 (2) ŵ = 0.24 mm1
c = 17.313 (4) ÅT = 293 K
β = 98.69 (3)°Prism, colourless
V = 3231.5 (11) Å30.20 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
5715 independent reflections
Radiation source: fine-focus sealed tube2714 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ω scansθmax = 25.1°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2017
Tmin = 0.953, Tmax = 0.976k = 1313
16422 measured reflectionsl = 1420
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-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 reflectionsΔρmax = 0.31 e Å3
393 parametersΔρmin = 0.36 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0020 (6)
Crystal data top
C29H27Cl2N5O2·C4H8OV = 3231.5 (11) Å3
Mr = 620.56Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.888 (3) ŵ = 0.24 mm1
b = 11.180 (2) ÅT = 293 K
c = 17.313 (4) Å0.20 × 0.20 × 0.10 mm
β = 98.69 (3)°
Data collection top
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 = 0.976Rint = 0.037
16422 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.171H-atom parameters constrained
S = 0.95Δρmax = 0.31 e Å3
5715 reflectionsΔρmin = 0.36 e Å3
393 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.60818 (16)0.4491 (2)0.07953 (16)0.0487 (7)
C20.61080 (17)0.4038 (2)0.00456 (17)0.0545 (8)
C30.5585 (2)0.3053 (3)0.03305 (18)0.0768 (10)
H3A0.57630.28220.08100.115*
H3B0.50410.33270.04380.115*
H3C0.56170.23780.00150.115*
N10.66326 (15)0.4459 (2)0.03987 (13)0.0595 (7)
C50.71460 (17)0.5337 (3)0.01436 (16)0.0567 (8)
C60.7692 (2)0.5687 (3)0.07116 (18)0.0774 (10)
H6A0.75910.51850.11650.116*
H6B0.82390.55940.04700.116*
H6C0.75970.65070.08630.116*
C70.71516 (16)0.5856 (2)0.05992 (16)0.0497 (7)
C80.55499 (17)0.4029 (3)0.13232 (16)0.0515 (7)
C90.56623 (19)0.4295 (3)0.21808 (17)0.0738 (10)
H9A0.56410.51490.22750.089*
H9B0.61700.39860.24400.089*
C100.49590 (18)0.3651 (3)0.24637 (16)0.0605 (8)
H100.51660.30340.28430.073*
C110.43991 (17)0.4448 (3)0.28162 (16)0.0556 (8)
C120.4319 (2)0.4375 (3)0.35906 (19)0.0790 (10)
H120.46220.38180.39060.095*
C130.3796 (2)0.5111 (3)0.3915 (2)0.0890 (11)
H130.37510.50480.44420.107*
C140.3353 (2)0.5921 (3)0.3460 (2)0.0743 (10)
C150.3422 (2)0.6030 (3)0.2690 (2)0.0839 (11)
H150.31230.65970.23800.101*
C160.3946 (2)0.5282 (3)0.23771 (19)0.0773 (10)
H160.39890.53520.18500.093*
C170.40085 (19)0.2213 (3)0.1693 (2)0.0646 (9)
C180.3759 (2)0.1615 (3)0.0924 (2)0.0840 (11)
H18A0.41670.10620.08260.126*
H18B0.36830.22060.05170.126*
H18C0.32660.11910.09340.126*
C190.76779 (17)0.6835 (2)0.09060 (17)0.0533 (7)
C200.82785 (18)0.8467 (3)0.16815 (18)0.0634 (8)
H200.79950.92340.16280.076*
C210.7666 (2)0.7438 (3)0.16844 (18)0.0712 (9)
H21A0.78300.68900.21130.085*
H21B0.71370.77460.17260.085*
C220.9101 (2)0.8921 (3)0.0629 (2)0.0842 (11)
C230.9350 (3)0.8490 (4)0.0120 (2)0.1197 (17)
H23A0.97540.90120.02650.179*
H23B0.88940.84890.05260.179*
H23C0.95600.76930.00490.179*
C240.89355 (19)0.8516 (3)0.23768 (18)0.0601 (8)
C250.9417 (2)0.7542 (3)0.2596 (2)0.0760 (10)
H250.93210.68270.23240.091*
C261.0037 (3)0.7608 (4)0.3210 (2)0.0918 (12)
H261.03590.69450.33530.110*
C271.0171 (3)0.8655 (5)0.3602 (2)0.0953 (12)
C280.9697 (3)0.9627 (4)0.3417 (2)0.0921 (12)
H280.97891.03310.37030.111*
C290.9079 (2)0.9559 (3)0.2799 (2)0.0767 (10)
H290.87551.02230.26670.092*
C300.7975 (7)0.4446 (8)0.3062 (6)0.264 (6)
H30A0.77780.46450.25210.317*
H30B0.80690.51800.33590.317*
C310.8602 (6)0.3835 (13)0.3112 (7)0.272 (6)
H31A0.90710.43170.32910.327*
H31B0.86590.34740.26140.327*
C320.8479 (8)0.2933 (8)0.3685 (10)0.309 (7)
H32A0.83210.21760.34350.371*
H32B0.89610.28150.40600.371*
C330.7871 (7)0.3404 (12)0.4042 (4)0.259 (5)
H33A0.76120.28110.43270.311*
H33B0.80410.40830.43740.311*
Cl11.09785 (9)0.87718 (15)0.43586 (8)0.1632 (7)
Cl20.26751 (7)0.68157 (10)0.38565 (7)0.1173 (5)
C40.66139 (16)0.5401 (2)0.10563 (15)0.0507 (7)
H4A0.66100.57160.15530.061*
N20.49515 (14)0.3347 (2)0.10922 (13)0.0552 (6)
N30.45775 (15)0.3068 (2)0.17305 (14)0.0623 (7)
N40.82032 (15)0.7275 (2)0.05271 (14)0.0632 (7)
N50.85993 (15)0.8201 (2)0.09521 (14)0.0677 (7)
O10.37297 (14)0.19533 (19)0.22848 (14)0.0840 (7)
O20.93475 (17)0.9838 (2)0.09668 (14)0.1037 (9)
O30.7430 (3)0.3717 (6)0.3371 (5)0.261 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0502 (18)0.0502 (17)0.0481 (17)0.0035 (14)0.0149 (13)0.0042 (13)
C20.0529 (19)0.0607 (19)0.0503 (18)0.0040 (15)0.0093 (15)0.0033 (14)
C30.086 (3)0.090 (2)0.057 (2)0.029 (2)0.0194 (17)0.0155 (17)
N10.0638 (17)0.0687 (17)0.0483 (15)0.0095 (14)0.0156 (13)0.0002 (12)
C50.059 (2)0.065 (2)0.0502 (19)0.0019 (17)0.0198 (15)0.0054 (15)
C60.079 (2)0.097 (3)0.062 (2)0.018 (2)0.0332 (18)0.0049 (18)
C70.0493 (18)0.0514 (17)0.0509 (18)0.0021 (14)0.0160 (14)0.0049 (13)
C80.0512 (19)0.0568 (18)0.0483 (18)0.0031 (15)0.0130 (14)0.0025 (14)
C90.069 (2)0.106 (3)0.0494 (19)0.0218 (19)0.0191 (16)0.0043 (17)
C100.063 (2)0.071 (2)0.0493 (18)0.0085 (17)0.0149 (15)0.0097 (15)
C110.060 (2)0.065 (2)0.0429 (18)0.0101 (16)0.0134 (15)0.0078 (15)
C120.101 (3)0.085 (3)0.053 (2)0.013 (2)0.0188 (19)0.0137 (18)
C130.120 (3)0.094 (3)0.059 (2)0.003 (3)0.032 (2)0.003 (2)
C140.074 (2)0.069 (2)0.082 (3)0.0083 (19)0.017 (2)0.0141 (19)
C150.091 (3)0.076 (2)0.080 (3)0.008 (2)0.001 (2)0.005 (2)
C160.088 (3)0.090 (3)0.053 (2)0.006 (2)0.0098 (18)0.0104 (19)
C170.064 (2)0.056 (2)0.080 (3)0.0052 (17)0.0312 (18)0.0061 (17)
C180.086 (3)0.071 (2)0.100 (3)0.025 (2)0.028 (2)0.013 (2)
C190.0510 (18)0.0547 (18)0.0569 (19)0.0065 (15)0.0166 (15)0.0053 (14)
C200.061 (2)0.059 (2)0.074 (2)0.0064 (16)0.0248 (17)0.0054 (16)
C210.067 (2)0.079 (2)0.074 (2)0.0209 (18)0.0321 (17)0.0136 (17)
C220.088 (3)0.090 (3)0.078 (3)0.042 (2)0.026 (2)0.006 (2)
C230.138 (4)0.149 (4)0.086 (3)0.075 (3)0.063 (3)0.016 (3)
C240.065 (2)0.058 (2)0.062 (2)0.0119 (17)0.0270 (16)0.0035 (16)
C250.087 (3)0.065 (2)0.078 (2)0.009 (2)0.018 (2)0.0066 (18)
C260.093 (3)0.091 (3)0.089 (3)0.006 (2)0.010 (2)0.014 (2)
C270.103 (3)0.111 (3)0.070 (3)0.026 (3)0.008 (2)0.000 (2)
C280.112 (3)0.087 (3)0.078 (3)0.031 (3)0.016 (2)0.027 (2)
C290.089 (3)0.063 (2)0.082 (3)0.0087 (19)0.026 (2)0.0139 (18)
C300.200 (9)0.245 (10)0.344 (12)0.037 (9)0.030 (9)0.194 (9)
C310.172 (8)0.43 (2)0.246 (11)0.069 (10)0.118 (8)0.043 (10)
C320.337 (17)0.183 (8)0.391 (19)0.106 (9)0.002 (13)0.113 (10)
C330.288 (13)0.412 (17)0.082 (5)0.054 (11)0.046 (6)0.043 (7)
Cl10.1458 (12)0.2111 (15)0.1152 (10)0.0404 (11)0.0362 (9)0.0005 (9)
Cl20.1092 (9)0.1077 (9)0.1404 (10)0.0055 (7)0.0365 (7)0.0408 (7)
C40.0535 (18)0.0540 (18)0.0476 (17)0.0036 (15)0.0173 (14)0.0003 (13)
N20.0572 (16)0.0591 (15)0.0530 (15)0.0118 (13)0.0199 (12)0.0011 (12)
N30.0685 (18)0.0679 (17)0.0552 (16)0.0182 (14)0.0247 (13)0.0002 (12)
N40.0627 (18)0.0715 (17)0.0588 (16)0.0186 (14)0.0205 (13)0.0003 (13)
N50.0727 (18)0.0739 (18)0.0610 (17)0.0265 (15)0.0251 (14)0.0021 (14)
O10.0943 (18)0.0717 (15)0.0984 (18)0.0104 (13)0.0544 (14)0.0121 (13)
O20.127 (2)0.0940 (19)0.0980 (19)0.0551 (17)0.0416 (16)0.0050 (15)
O30.146 (4)0.291 (7)0.330 (9)0.017 (4)0.017 (5)0.093 (6)
Geometric parameters (Å, º) top
C1—C41.387 (3)C19—N41.278 (3)
C1—C21.400 (4)C19—C211.509 (4)
C1—C81.469 (4)C20—N51.478 (4)
C2—N11.343 (3)C20—C241.510 (4)
C2—C31.497 (4)C20—C211.547 (4)
C3—H3A0.9600C20—H200.9800
C3—H3B0.9600C21—H21A0.9700
C3—H3C0.9600C21—H21B0.9700
N1—C51.340 (3)C22—O21.222 (4)
C5—C71.410 (4)C22—N51.350 (4)
C5—C61.498 (4)C22—C231.502 (5)
C6—H6A0.9600C23—H23A0.9600
C6—H6B0.9600C23—H23B0.9600
C6—H6C0.9600C23—H23C0.9600
C7—C41.388 (4)C24—C251.377 (4)
C7—C191.459 (4)C24—C291.378 (4)
C8—N21.281 (3)C25—C261.378 (5)
C8—C91.498 (4)C25—H250.9300
C9—C101.531 (4)C26—C271.355 (5)
C9—H9A0.9700C26—H260.9300
C9—H9B0.9700C27—C281.359 (5)
C10—N31.485 (4)C27—Cl11.747 (4)
C10—C111.495 (4)C28—C291.378 (5)
C10—H100.9800C28—H280.9300
C11—C161.363 (4)C29—H290.9300
C11—C121.370 (4)C30—C311.252 (10)
C12—C131.386 (5)C30—O31.396 (8)
C12—H120.9300C30—H30A0.9700
C13—C141.349 (5)C30—H30B0.9700
C13—H130.9300C31—C321.452 (12)
C14—C151.361 (5)C31—H31A0.9700
C14—Cl21.738 (4)C31—H31B0.9700
C15—C161.386 (5)C32—C331.380 (13)
C15—H150.9300C32—H32A0.9700
C16—H160.9300C32—H32B0.9700
C17—O11.226 (3)C33—O31.328 (9)
C17—N31.350 (4)C33—H33A0.9700
C17—C181.493 (4)C33—H33B0.9700
C18—H18A0.9600C4—H4A0.9300
C18—H18B0.9600N2—N31.389 (3)
C18—H18C0.9600N4—N51.384 (3)
C4—C1—C2117.2 (2)N5—C20—H20109.5
C4—C1—C8118.8 (2)C24—C20—H20109.5
C2—C1—C8123.9 (3)C21—C20—H20109.5
N1—C2—C1121.3 (3)C19—C21—C20103.3 (2)
N1—C2—C3113.9 (3)C19—C21—H21A111.1
C1—C2—C3124.7 (3)C20—C21—H21A111.1
C2—C3—H3A109.5C19—C21—H21B111.1
C2—C3—H3B109.5C20—C21—H21B111.1
H3A—C3—H3B109.5H21A—C21—H21B109.1
C2—C3—H3C109.5O2—C22—N5119.4 (3)
H3A—C3—H3C109.5O2—C22—C23124.3 (3)
H3B—C3—H3C109.5N5—C22—C23116.2 (3)
C5—N1—C2121.2 (2)C22—C23—H23A109.5
N1—C5—C7121.1 (2)C22—C23—H23B109.5
N1—C5—C6114.0 (3)H23A—C23—H23B109.5
C7—C5—C6124.9 (3)C22—C23—H23C109.5
C5—C6—H6A109.5H23A—C23—H23C109.5
C5—C6—H6B109.5H23B—C23—H23C109.5
H6A—C6—H6B109.5C25—C24—C29118.3 (3)
C5—C6—H6C109.5C25—C24—C20121.5 (3)
H6A—C6—H6C109.5C29—C24—C20120.2 (3)
H6B—C6—H6C109.5C24—C25—C26121.3 (3)
C4—C7—C5117.0 (3)C24—C25—H25119.4
C4—C7—C19118.9 (3)C26—C25—H25119.4
C5—C7—C19124.1 (2)C27—C26—C25118.8 (4)
N2—C8—C1122.9 (2)C27—C26—H26120.6
N2—C8—C9113.8 (2)C25—C26—H26120.6
C1—C8—C9123.3 (3)C26—C27—C28121.7 (4)
C8—C9—C10103.6 (2)C26—C27—Cl1119.5 (4)
C8—C9—H9A111.0C28—C27—Cl1118.8 (4)
C10—C9—H9A111.0C27—C28—C29119.2 (3)
C8—C9—H9B111.0C27—C28—H28120.4
C10—C9—H9B111.0C29—C28—H28120.4
H9A—C9—H9B109.0C24—C29—C28120.7 (4)
N3—C10—C11113.0 (2)C24—C29—H29119.7
N3—C10—C9101.0 (2)C28—C29—H29119.7
C11—C10—C9114.8 (3)C31—C30—O3104.8 (8)
N3—C10—H10109.2C31—C30—H30A110.8
C11—C10—H10109.2O3—C30—H30A110.8
C9—C10—H10109.2C31—C30—H30B110.8
C16—C11—C12117.2 (3)O3—C30—H30B110.8
C16—C11—C10121.1 (3)H30A—C30—H30B108.9
C12—C11—C10121.7 (3)C30—C31—C32102.7 (8)
C11—C12—C13121.6 (3)C30—C31—H31A111.2
C11—C12—H12119.2C32—C31—H31A111.2
C13—C12—H12119.2C30—C31—H31B111.2
C14—C13—C12119.5 (3)C32—C31—H31B111.2
C14—C13—H13120.2H31A—C31—H31B109.1
C12—C13—H13120.2C33—C32—C31103.5 (8)
C13—C14—C15120.6 (3)C33—C32—H32A111.1
C13—C14—Cl2119.8 (3)C31—C32—H32A111.1
C15—C14—Cl2119.6 (3)C33—C32—H32B111.1
C14—C15—C16118.9 (3)C31—C32—H32B111.1
C14—C15—H15120.5H32A—C32—H32B109.0
C16—C15—H15120.5O3—C33—C3293.9 (7)
C11—C16—C15122.2 (3)O3—C33—H33A113.0
C11—C16—H16118.9C32—C33—H33A113.0
C15—C16—H16118.9O3—C33—H33B113.0
O1—C17—N3119.2 (3)C32—C33—H33B113.0
O1—C17—C18123.2 (3)H33A—C33—H33B110.4
N3—C17—C18117.6 (3)C1—C4—C7122.1 (3)
C17—C18—H18A109.5C1—C4—H4A119.0
C17—C18—H18B109.5C7—C4—H4A119.0
H18A—C18—H18B109.5C8—N2—N3108.5 (2)
C17—C18—H18C109.5C17—N3—N2121.8 (2)
H18A—C18—H18C109.5C17—N3—C10124.5 (3)
H18B—C18—H18C109.5N2—N3—C10113.0 (2)
N4—C19—C7122.2 (3)C19—N4—N5109.4 (2)
N4—C19—C21113.0 (3)C22—N5—N4120.6 (3)
C7—C19—C21124.8 (2)C22—N5—C20124.7 (3)
N5—C20—C24111.6 (3)N4—N5—C20113.3 (2)
N5—C20—C21100.6 (2)C33—O3—C30100.0 (7)
C24—C20—C21115.8 (3)
C4—C1—C2—N10.7 (4)C21—C20—C24—C29127.4 (3)
C8—C1—C2—N1176.9 (3)C29—C24—C25—C261.4 (5)
C4—C1—C2—C3179.5 (3)C20—C24—C25—C26177.1 (3)
C8—C1—C2—C31.9 (5)C24—C25—C26—C270.1 (6)
C1—C2—N1—C50.6 (4)C25—C26—C27—C281.6 (6)
C3—C2—N1—C5179.6 (3)C25—C26—C27—Cl1177.6 (3)
C2—N1—C5—C70.4 (4)C26—C27—C28—C291.9 (6)
C2—N1—C5—C6179.4 (3)Cl1—C27—C28—C29177.3 (3)
N1—C5—C7—C41.2 (4)C25—C24—C29—C281.1 (5)
C6—C5—C7—C4178.5 (3)C20—C24—C29—C28177.5 (3)
N1—C5—C7—C19178.3 (3)C27—C28—C29—C240.5 (6)
C6—C5—C7—C192.0 (5)O3—C30—C31—C3218.4 (14)
C4—C1—C8—N2167.5 (3)C30—C31—C32—C3317.0 (16)
C2—C1—C8—N214.9 (4)C31—C32—C33—O345.8 (12)
C4—C1—C8—C913.4 (4)C2—C1—C4—C70.2 (4)
C2—C1—C8—C9164.2 (3)C8—C1—C4—C7178.0 (2)
N2—C8—C9—C102.2 (4)C5—C7—C4—C11.1 (4)
C1—C8—C9—C10178.7 (3)C19—C7—C4—C1178.4 (2)
C8—C9—C10—N32.6 (3)C1—C8—N2—N3179.7 (2)
C8—C9—C10—C11119.2 (3)C9—C8—N2—N30.6 (3)
N3—C10—C11—C1649.3 (4)O1—C17—N3—N2175.8 (3)
C9—C10—C11—C1665.7 (4)C18—C17—N3—N23.2 (4)
N3—C10—C11—C12130.7 (3)O1—C17—N3—C106.3 (5)
C9—C10—C11—C12114.2 (3)C18—C17—N3—C10172.7 (3)
C16—C11—C12—C130.4 (5)C8—N2—N3—C17169.2 (3)
C10—C11—C12—C13179.7 (3)C8—N2—N3—C101.4 (3)
C11—C12—C13—C140.1 (6)C11—C10—N3—C1769.2 (4)
C12—C13—C14—C150.8 (6)C9—C10—N3—C17167.7 (3)
C12—C13—C14—Cl2178.1 (3)C11—C10—N3—N2120.5 (3)
C13—C14—C15—C161.0 (5)C9—C10—N3—N22.6 (3)
Cl2—C14—C15—C16177.8 (3)C7—C19—N4—N5178.8 (2)
C12—C11—C16—C150.1 (5)C21—C19—N4—N51.0 (4)
C10—C11—C16—C15179.9 (3)O2—C22—N5—N4168.8 (3)
C14—C15—C16—C110.6 (5)C23—C22—N5—N414.0 (5)
C4—C7—C19—N4177.9 (3)O2—C22—N5—C203.5 (6)
C5—C7—C19—N42.6 (4)C23—C22—N5—C20179.3 (3)
C4—C7—C19—C212.4 (4)C19—N4—N5—C22170.4 (3)
C5—C7—C19—C21177.1 (3)C19—N4—N5—C203.6 (3)
N4—C19—C21—C204.7 (4)C24—C20—N5—C2264.2 (4)
C7—C19—C21—C20175.0 (3)C21—C20—N5—C22172.4 (3)
N5—C20—C21—C196.0 (3)C24—C20—N5—N4129.5 (3)
C24—C20—C21—C19126.5 (3)C21—C20—N5—N46.1 (3)
N5—C20—C24—C2560.2 (4)C32—C33—O3—C3056.7 (11)
C21—C20—C24—C2554.1 (4)C31—C30—O3—C3350.4 (13)
N5—C20—C24—C29118.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9B···O30.972.493.423 (7)163
C21—H21B···O1i0.972.573.211 (4)123
C9—H9A···O1i0.972.353.234 (4)151
C23—H23A···O2ii0.962.453.385 (4)166
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+2, y+2, z.

Experimental details

Crystal data
Chemical formulaC29H27Cl2N5O2·C4H8O
Mr620.56
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)16.888 (3), 11.180 (2), 17.313 (4)
β (°) 98.69 (3)
V3)3231.5 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.20 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.953, 0.976
No. of measured, independent and
observed [I > 2σ(I)] reflections
16422, 5715, 2714
Rint0.037
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.171, 0.95
No. of reflections5715
No. of parameters393
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.31, 0.36

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9B···O30.972.493.423 (7)162.5
C21—H21B···O1i0.972.573.211 (4)123.4
C9—H9A···O1i0.972.353.234 (4)150.6
C23—H23A···O2ii0.962.453.385 (4)165.5
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+2, y+2, z.
 

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