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The reaction of 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde and N-benzyl­methyl­amine under microwave irradiation gives 5-[benzyl(methyl)amino]-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde, C19H19N3O, (I). Subsequent reactions under basic conditions, between (I) and a range of aceto­phenones, yield the corresponding chalcones. These undergo cyclocondensation reactions with hydrazine to produce reduced bi­pyrazoles which can be N-formyl­ated with formic acid or N-acetyl­ated with acetic anhydride. The structures of (I) and of representative examples from this reaction sequence are reported, namely the chalcone (E)-3-{5-[benzyl(methyl)amino]-3-methyl-1-phenyl-1H-pyrazol-4-yl}-1-(4-bromo­phenyl)prop-2-en-1-one, C27H24BrN3O, (II), the N-formyl derivative (3RS)-5′-[benzyl(methyl)amino]-3′-methyl-1′,5-diphenyl-3,4-di­hydro-1′H,2H-[3,4′-bi­pyrazole]-2-carbaldehyde, C28H27N5O, (III), and the N-acetyl derivative (3RS)-2-acetyl-5′-[benzyl(methyl)amino]-5-(4-meth­oxy­phenyl)-3′-methyl-1′-phenyl-3,4-di­hydro-1′H,2H-[3,4′-bi­pyrazole], which crystallizes as the ethanol 0.945-solvate, C30H31N5O2·0.945C2H6O, (IV). There is significant delocalization of charge from the benzyl(methyl)amino substituent onto the carbonyl group in (I), but not in (II). In each of (III) and (IV), the reduced pyrazole ring is modestly puckered into an envelope conformation. The mol­ecules of (I) are linked by a combination of C—H...N and C—H...π(arene) hydrogen bonds to form a simple chain of rings; those of (III) are linked by a combination of C—H...O and C—H...N hydrogen bonds to form sheets of R22(8) and R66(42) rings, and those of (IV) are linked by a combination of O—H...N and C—H...O hydrogen bonds to form a ribbon of edge-fused R24(16) and R44(24) rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961701302X/sk3669sup1.cif
Contains datablocks global, I, II, III, IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961701302X/sk3669Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961701302X/sk3669IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961701302X/sk3669IIIsup4.hkl
Contains datablock III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961701302X/sk3669IVsup5.hkl
Contains datablock IV

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961701302X/sk3669Isup6.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961701302X/sk3669IIsup7.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961701302X/sk3669IIIsup8.cml
Supplementary material

CCDC references: 1574032; 1574031; 1574030; 1574029

Computing details top

For all structures, data collection: APEX3 (Bruker2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

5-[Benzyl(methyl)amino]-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (I) top
Crystal data top
C19H19N3OF(000) = 648
Mr = 305.37Dx = 1.269 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.811 (4) ÅCell parameters from 3698 reflections
b = 17.951 (9) Åθ = 2.3–27.6°
c = 11.405 (6) ŵ = 0.08 mm1
β = 92.36 (2)°T = 100 K
V = 1597.8 (14) Å3Block, yellow
Z = 40.32 × 0.27 × 0.12 mm
Data collection top
Bruker D8 Venture
diffractometer
3695 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube3267 reflections with I > 2σ(I)
Multilayer mirror monochromatorRint = 0.037
φ and ω scansθmax = 27.6°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS-2016/2; Bruker, 2016)
h = 1010
Tmin = 0.969, Tmax = 0.990k = 2323
51127 measured reflectionsl = 1414
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040 w = 1/[σ2(Fo2) + (0.0407P)2 + 0.8359P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.102(Δ/σ)max < 0.001
S = 1.09Δρmax = 0.32 e Å3
3695 reflectionsΔρmin = 0.22 e Å3
211 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0228 (18)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.42676 (12)0.39892 (5)0.43035 (9)0.0148 (2)
N20.55934 (12)0.41928 (6)0.35885 (9)0.0171 (2)
C30.48214 (15)0.44267 (6)0.26119 (10)0.0161 (2)
C40.30058 (14)0.43969 (6)0.26622 (10)0.0142 (2)
C50.26987 (14)0.41160 (6)0.37866 (10)0.0131 (2)
C110.47210 (14)0.35779 (6)0.53391 (10)0.0147 (2)
C120.58714 (16)0.38847 (7)0.61571 (11)0.0193 (3)
H120.63230.43690.60420.023*
C130.63574 (17)0.34765 (8)0.71461 (11)0.0251 (3)
H130.71450.36830.77140.030*
C140.57062 (17)0.27723 (8)0.73124 (12)0.0254 (3)
H140.60410.24950.79940.031*
C150.45633 (16)0.24705 (8)0.64838 (12)0.0242 (3)
H150.41120.19860.66000.029*
C160.40716 (15)0.28694 (7)0.54868 (11)0.0192 (3)
H160.32990.26590.49130.023*
C310.58601 (16)0.47034 (8)0.16327 (12)0.0238 (3)
H31C0.70810.46680.18600.036*
H31A0.55630.52240.14630.036*
H31B0.56180.44000.09310.036*
C410.18260 (15)0.47438 (6)0.18354 (10)0.0165 (2)
H410.22960.49430.11470.020*
O410.02824 (11)0.48099 (5)0.19223 (8)0.0208 (2)
N510.11994 (12)0.40354 (6)0.43358 (9)0.0152 (2)
C510.11004 (16)0.41319 (7)0.55967 (11)0.0197 (3)
H51A0.20430.44510.58860.029*
H51C0.11870.36450.59830.029*
H51B0.00040.43640.57700.029*
C520.02353 (15)0.36432 (7)0.37385 (11)0.0183 (3)
H52B0.01880.37220.28810.022*
H52A0.13290.38530.39980.022*
C5210.01818 (14)0.28206 (7)0.39978 (10)0.0166 (2)
C5220.07510 (16)0.23446 (7)0.33113 (11)0.0217 (3)
H5220.12990.25330.26440.026*
C5230.0888 (2)0.15969 (8)0.35925 (12)0.0295 (3)
H5230.15400.12750.31230.035*
C5240.0080 (2)0.13174 (8)0.45545 (13)0.0330 (4)
H5240.01790.08040.47480.040*
C5250.0868 (2)0.17837 (8)0.52316 (12)0.0302 (3)
H5250.14290.15910.58900.036*
C5260.10069 (16)0.25322 (7)0.49549 (11)0.0221 (3)
H5260.16700.28510.54220.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0113 (4)0.0153 (5)0.0177 (5)0.0007 (4)0.0002 (4)0.0029 (4)
N20.0134 (5)0.0181 (5)0.0198 (5)0.0003 (4)0.0017 (4)0.0028 (4)
C30.0155 (5)0.0137 (5)0.0191 (6)0.0010 (4)0.0008 (4)0.0004 (4)
C40.0145 (5)0.0112 (5)0.0170 (5)0.0002 (4)0.0000 (4)0.0007 (4)
C50.0132 (5)0.0089 (5)0.0171 (5)0.0005 (4)0.0018 (4)0.0011 (4)
C110.0127 (5)0.0154 (5)0.0161 (5)0.0038 (4)0.0005 (4)0.0017 (4)
C120.0187 (6)0.0185 (6)0.0203 (6)0.0014 (4)0.0024 (4)0.0028 (5)
C130.0232 (6)0.0333 (7)0.0181 (6)0.0054 (5)0.0056 (5)0.0038 (5)
C140.0225 (6)0.0346 (7)0.0192 (6)0.0089 (5)0.0007 (5)0.0091 (5)
C150.0196 (6)0.0220 (6)0.0312 (7)0.0026 (5)0.0020 (5)0.0104 (5)
C160.0153 (5)0.0179 (6)0.0240 (6)0.0006 (4)0.0031 (4)0.0026 (5)
C310.0188 (6)0.0289 (7)0.0239 (6)0.0007 (5)0.0046 (5)0.0061 (5)
C410.0195 (6)0.0135 (5)0.0162 (5)0.0016 (4)0.0014 (4)0.0014 (4)
O410.0175 (4)0.0191 (4)0.0253 (5)0.0017 (3)0.0032 (3)0.0055 (4)
N510.0123 (5)0.0172 (5)0.0162 (5)0.0004 (4)0.0002 (4)0.0014 (4)
C510.0201 (6)0.0213 (6)0.0178 (6)0.0034 (5)0.0037 (4)0.0001 (5)
C520.0120 (5)0.0190 (6)0.0236 (6)0.0016 (4)0.0034 (4)0.0058 (5)
C5210.0122 (5)0.0191 (6)0.0181 (6)0.0025 (4)0.0046 (4)0.0022 (4)
C5220.0214 (6)0.0272 (7)0.0160 (6)0.0004 (5)0.0036 (4)0.0019 (5)
C5230.0391 (8)0.0244 (7)0.0239 (7)0.0087 (6)0.0125 (6)0.0106 (5)
C5240.0547 (10)0.0159 (6)0.0264 (7)0.0019 (6)0.0225 (6)0.0005 (5)
C5250.0427 (8)0.0256 (7)0.0216 (7)0.0126 (6)0.0071 (6)0.0074 (5)
C5260.0226 (6)0.0224 (6)0.0214 (6)0.0036 (5)0.0014 (5)0.0015 (5)
Geometric parameters (Å, º) top
N1—C51.3571 (16)C31—H31B0.9800
N1—N21.3931 (15)C41—O411.2196 (16)
N1—C111.4252 (16)C41—H410.9500
N2—C31.3135 (16)N51—C511.4536 (17)
C3—C41.4227 (17)N51—C521.4672 (16)
C3—C311.4922 (17)C51—H51A0.9800
C4—C51.4077 (17)C51—H51C0.9800
C4—C411.4334 (16)C51—H51B0.9800
C5—N511.3584 (16)C52—C5211.5061 (18)
C11—C161.3820 (18)C52—H52B0.9900
C11—C121.3827 (17)C52—H52A0.9900
C12—C131.3850 (19)C521—C5221.3860 (18)
C12—H120.9500C521—C5261.3903 (18)
C13—C141.379 (2)C522—C5231.383 (2)
C13—H130.9500C522—H5220.9500
C14—C151.384 (2)C523—C5241.383 (2)
C14—H140.9500C523—H5230.9500
C15—C161.3846 (18)C524—C5251.376 (2)
C15—H150.9500C524—H5240.9500
C16—H160.9500C525—C5261.383 (2)
C31—H31C0.9800C525—H5250.9500
C31—H31A0.9800C526—H5260.9500
C5—N1—N2112.42 (10)O41—C41—C4126.85 (11)
C5—N1—C11129.50 (10)O41—C41—H41116.6
N2—N1—C11117.11 (9)C4—C41—H41116.6
C3—N2—N1104.71 (10)C5—N51—C51121.70 (10)
N2—C3—C4112.17 (11)C5—N51—C52119.57 (10)
N2—C3—C31119.75 (11)C51—N51—C52116.48 (10)
C4—C3—C31128.05 (11)N51—C51—H51A109.5
C5—C4—C3104.94 (10)N51—C51—H51C109.5
C5—C4—C41128.74 (11)H51A—C51—H51C109.5
C3—C4—C41124.89 (11)N51—C51—H51B109.5
N1—C5—N51124.20 (11)H51A—C51—H51B109.5
N1—C5—C4105.73 (10)H51C—C51—H51B109.5
N51—C5—C4129.84 (10)N51—C52—C521111.40 (10)
C16—C11—C12121.05 (11)N51—C52—H52B109.3
C16—C11—N1119.86 (11)C521—C52—H52B109.3
C12—C11—N1119.02 (11)N51—C52—H52A109.3
C11—C12—C13119.17 (12)C521—C52—H52A109.3
C11—C12—H12120.4H52B—C52—H52A108.0
C13—C12—H12120.4C522—C521—C526119.04 (12)
C14—C13—C12120.46 (12)C522—C521—C52120.29 (11)
C14—C13—H13119.8C526—C521—C52120.62 (11)
C12—C13—H13119.8C523—C522—C521120.32 (13)
C13—C14—C15119.76 (12)C523—C522—H522119.8
C13—C14—H14120.1C521—C522—H522119.8
C15—C14—H14120.1C524—C523—C522120.18 (13)
C14—C15—C16120.51 (13)C524—C523—H523119.9
C14—C15—H15119.7C522—C523—H523119.9
C16—C15—H15119.7C525—C524—C523119.91 (13)
C11—C16—C15119.03 (12)C525—C524—H524120.0
C11—C16—H16120.5C523—C524—H524120.0
C15—C16—H16120.5C524—C525—C526120.12 (14)
C3—C31—H31C109.5C524—C525—H525119.9
C3—C31—H31A109.5C526—C525—H525119.9
H31C—C31—H31A109.5C525—C526—C521120.43 (13)
C3—C31—H31B109.5C525—C526—H526119.8
H31C—C31—H31B109.5C521—C526—H526119.8
H31A—C31—H31B109.5
C5—N1—N2—C31.74 (13)C12—C13—C14—C150.2 (2)
C11—N1—N2—C3168.09 (10)C13—C14—C15—C160.2 (2)
N1—N2—C3—C41.02 (13)C12—C11—C16—C151.25 (18)
N1—N2—C3—C31179.18 (11)N1—C11—C16—C15178.26 (11)
N2—C3—C4—C50.01 (13)C14—C15—C16—C110.88 (19)
C31—C3—C4—C5177.99 (12)C5—C4—C41—O416.0 (2)
N2—C3—C4—C41167.35 (11)C3—C4—C41—O41170.30 (12)
C31—C3—C4—C4110.63 (19)N1—C5—N51—C5128.02 (17)
N2—N1—C5—N51173.27 (10)C4—C5—N51—C51145.73 (12)
C11—N1—C5—N5118.48 (18)N1—C5—N51—C52134.32 (12)
N2—N1—C5—C41.75 (12)C4—C5—N51—C5251.93 (17)
C11—N1—C5—C4166.50 (11)C5—N51—C52—C52189.82 (13)
C3—C4—C5—N11.03 (12)C51—N51—C52—C52173.42 (13)
C41—C4—C5—N1167.73 (11)N51—C52—C521—C52287.50 (14)
C3—C4—C5—N51173.60 (11)N51—C52—C521—C52689.88 (14)
C41—C4—C5—N516.9 (2)C526—C521—C522—C5231.45 (18)
C5—N1—C11—C1649.04 (17)C52—C521—C522—C523175.97 (11)
N2—N1—C11—C16118.75 (12)C521—C522—C523—C5240.68 (19)
C5—N1—C11—C12133.89 (13)C522—C523—C524—C5250.2 (2)
N2—N1—C11—C1258.32 (15)C523—C524—C525—C5260.3 (2)
C16—C11—C12—C130.89 (18)C524—C525—C526—C5210.5 (2)
N1—C11—C12—C13177.92 (11)C522—C521—C526—C5251.34 (18)
C11—C12—C13—C140.16 (19)C52—C521—C526—C525176.06 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C52—H52A···N2i0.992.513.402 (2)150
C526—H526···Cg1i0.952.743.584 (2)148
Symmetry code: (i) x1, y, z.
(E)-3-{5-[Benzyl(methyl)amino]-3-methyl-1-phenyl-1H-pyrazol-4-yl}-1-(4-bromophenyl)prop-2-en-1-one (II) top
Crystal data top
C27H24BrN3OF(000) = 2000
Mr = 486.39Dx = 1.384 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 31.172 (16) ÅCell parameters from 5344 reflections
b = 10.039 (6) Åθ = 2.2–27.5°
c = 17.861 (10) ŵ = 1.79 mm1
β = 123.334 (14)°T = 100 K
V = 4670 (5) Å3Block, yellow
Z = 80.37 × 0.28 × 0.17 mm
Data collection top
Bruker D8 Venture
diffractometer
5343 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube3912 reflections with I > 2σ(I)
Multilayer mirror monochromatorRint = 0.117
φ and ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS-2016/2; Bruker, 2016)
h = 3540
Tmin = 0.717, Tmax = 0.738k = 1312
49556 measured reflectionsl = 2323
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.038P)2 + 18.3538P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
5343 reflectionsΔρmax = 0.63 e Å3
291 parametersΔρmin = 0.71 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.31616 (9)0.7080 (2)0.19362 (17)0.0204 (5)
N20.30659 (9)0.8281 (2)0.14792 (17)0.0196 (5)
C30.35258 (11)0.8829 (3)0.1831 (2)0.0185 (6)
C40.39294 (11)0.8001 (3)0.2501 (2)0.0178 (6)
C50.36735 (11)0.6881 (3)0.2548 (2)0.0191 (6)
C110.27401 (11)0.6341 (3)0.1846 (2)0.0201 (6)
C120.23830 (11)0.5731 (3)0.1027 (2)0.0229 (7)
H120.24090.58310.05240.028*
C130.19889 (12)0.4972 (3)0.0963 (2)0.0258 (7)
H130.17430.45550.04120.031*
C140.19541 (11)0.4824 (3)0.1701 (2)0.0244 (7)
H140.16910.42840.16580.029*
C150.23042 (12)0.5465 (3)0.2505 (2)0.0274 (7)
H150.22760.53760.30050.033*
C160.26946 (12)0.6233 (3)0.2572 (2)0.0246 (7)
H160.29300.66840.31150.030*
C310.35817 (11)1.0175 (3)0.1531 (2)0.0230 (7)
H31A0.32441.04950.10460.034*
H31B0.38101.01100.13160.034*
H31C0.37281.07980.20360.034*
C410.44734 (11)0.8243 (3)0.29311 (19)0.0187 (6)
H410.45670.91060.28510.022*
C420.48651 (11)0.7384 (3)0.3435 (2)0.0218 (6)
H420.47940.65170.35530.026*
C430.54010 (11)0.7781 (3)0.3804 (2)0.0199 (6)
O430.55314 (8)0.8956 (2)0.38735 (15)0.0247 (5)
C4310.57969 (11)0.6699 (3)0.41018 (19)0.0191 (6)
C4320.63165 (11)0.7039 (3)0.4637 (2)0.0227 (6)
H4320.64090.79430.48060.027*
C4330.67023 (11)0.6087 (3)0.4929 (2)0.0228 (6)
H4330.70540.63280.53000.027*
C4340.65561 (11)0.4764 (3)0.4660 (2)0.0202 (6)
Br440.70677 (2)0.34263 (3)0.50516 (2)0.02657 (11)
C4350.60448 (12)0.4399 (3)0.4115 (2)0.0252 (7)
H4350.59530.34990.39310.030*
C4360.56662 (11)0.5365 (3)0.3840 (2)0.0228 (7)
H4360.53150.51180.34710.027*
N510.38907 (9)0.5756 (2)0.30942 (17)0.0214 (5)
C510.41273 (13)0.5978 (3)0.4060 (2)0.0280 (7)
H51A0.38610.59520.41920.042*
H51B0.42970.68500.42280.042*
H51C0.43820.52800.44010.042*
C520.36431 (11)0.4447 (3)0.2763 (2)0.0244 (7)
H52A0.34700.44090.21040.029*
H52B0.33790.43250.29030.029*
C5210.40390 (11)0.3335 (3)0.3196 (2)0.0218 (6)
C5220.44605 (12)0.3300 (3)0.3122 (2)0.0261 (7)
H5220.45050.39850.28040.031*
C5230.48183 (13)0.2269 (3)0.3510 (2)0.0311 (8)
H5230.51020.22460.34500.037*
C5240.47571 (13)0.1271 (3)0.3989 (2)0.0327 (8)
H5240.50020.05710.42590.039*
C5250.43416 (14)0.1301 (3)0.4069 (2)0.0314 (8)
H5250.43000.06200.43940.038*
C5260.39795 (13)0.2333 (3)0.3672 (2)0.0255 (7)
H5260.36940.23490.37290.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0157 (12)0.0142 (11)0.0290 (14)0.0005 (9)0.0107 (11)0.0023 (10)
N20.0182 (12)0.0129 (11)0.0278 (13)0.0032 (9)0.0128 (11)0.0033 (10)
C30.0152 (14)0.0142 (13)0.0242 (15)0.0032 (10)0.0098 (12)0.0020 (11)
C40.0153 (14)0.0125 (12)0.0240 (15)0.0021 (10)0.0099 (12)0.0000 (11)
C50.0176 (14)0.0134 (13)0.0260 (15)0.0014 (10)0.0118 (12)0.0013 (11)
C110.0126 (14)0.0123 (13)0.0317 (16)0.0016 (10)0.0099 (12)0.0023 (11)
C120.0197 (15)0.0149 (13)0.0294 (17)0.0030 (11)0.0105 (13)0.0036 (12)
C130.0193 (16)0.0148 (14)0.0332 (18)0.0014 (11)0.0080 (14)0.0013 (12)
C140.0147 (14)0.0158 (13)0.0396 (19)0.0013 (11)0.0130 (14)0.0012 (13)
C150.0254 (17)0.0217 (15)0.0363 (19)0.0017 (12)0.0177 (15)0.0002 (13)
C160.0220 (16)0.0215 (15)0.0290 (17)0.0037 (12)0.0131 (13)0.0028 (12)
C310.0183 (15)0.0155 (13)0.0328 (17)0.0027 (11)0.0126 (13)0.0029 (12)
C410.0166 (14)0.0140 (13)0.0244 (15)0.0012 (10)0.0104 (12)0.0014 (11)
C420.0178 (15)0.0141 (13)0.0316 (17)0.0002 (11)0.0123 (13)0.0007 (12)
C430.0192 (15)0.0141 (13)0.0237 (15)0.0030 (11)0.0101 (12)0.0008 (11)
O430.0199 (11)0.0139 (10)0.0376 (13)0.0010 (8)0.0142 (10)0.0003 (9)
C4310.0162 (14)0.0160 (13)0.0240 (15)0.0012 (11)0.0105 (12)0.0008 (11)
C4320.0185 (15)0.0136 (13)0.0346 (17)0.0015 (11)0.0137 (13)0.0005 (12)
C4330.0136 (14)0.0194 (14)0.0312 (17)0.0025 (11)0.0097 (13)0.0020 (12)
C4340.0180 (14)0.0135 (13)0.0288 (16)0.0038 (11)0.0127 (13)0.0015 (12)
Br440.01821 (16)0.01703 (15)0.03877 (19)0.00509 (12)0.01204 (13)0.00039 (13)
C4350.0213 (16)0.0153 (14)0.0334 (18)0.0006 (11)0.0114 (14)0.0033 (12)
C4360.0116 (14)0.0194 (14)0.0321 (17)0.0018 (11)0.0086 (12)0.0024 (12)
N510.0190 (13)0.0106 (11)0.0278 (14)0.0006 (9)0.0086 (11)0.0022 (10)
C510.0268 (17)0.0218 (15)0.0292 (17)0.0032 (13)0.0115 (14)0.0034 (13)
C520.0174 (15)0.0110 (13)0.0366 (18)0.0009 (11)0.0096 (13)0.0022 (12)
C5210.0192 (15)0.0119 (13)0.0278 (16)0.0010 (11)0.0088 (12)0.0013 (12)
C5220.0212 (16)0.0194 (15)0.0339 (17)0.0003 (12)0.0127 (14)0.0028 (13)
C5230.0182 (16)0.0306 (18)0.039 (2)0.0021 (13)0.0122 (15)0.0041 (15)
C5240.0264 (18)0.0179 (15)0.0348 (19)0.0076 (12)0.0048 (15)0.0022 (13)
C5250.039 (2)0.0164 (15)0.0294 (18)0.0032 (13)0.0126 (15)0.0045 (12)
C5260.0274 (17)0.0192 (15)0.0293 (17)0.0004 (12)0.0151 (14)0.0016 (12)
Geometric parameters (Å, º) top
N1—C51.365 (4)C431—C4361.403 (4)
N1—N21.393 (3)C432—C4331.394 (4)
N1—C111.439 (4)C432—H4320.9500
N2—C31.327 (4)C433—C4341.400 (4)
C3—C41.432 (4)C433—H4330.9500
C3—C311.499 (4)C434—C4351.385 (4)
C4—C51.408 (4)C434—Br441.900 (3)
C4—C411.447 (4)C435—C4361.392 (4)
C5—N511.399 (4)C435—H4350.9500
C11—C161.384 (5)C436—H4360.9500
C11—C121.402 (4)N51—C511.473 (4)
C12—C131.396 (4)N51—C521.473 (4)
C12—H120.9500C51—H51A0.9800
C13—C141.388 (5)C51—H51B0.9800
C13—H130.9500C51—H51C0.9800
C14—C151.395 (5)C52—C5211.523 (4)
C14—H140.9500C52—H52A0.9900
C15—C161.389 (4)C52—H52B0.9900
C15—H150.9500C521—C5221.391 (5)
C16—H160.9500C521—C5261.394 (4)
C31—H31A0.9800C522—C5231.395 (4)
C31—H31B0.9800C522—H5220.9500
C31—H31C0.9800C523—C5241.396 (5)
C41—C421.355 (4)C523—H5230.9500
C41—H410.9500C524—C5251.380 (5)
C42—C431.475 (4)C524—H5240.9500
C42—H420.9500C525—C5261.404 (4)
C43—O431.231 (3)C525—H5250.9500
C43—C4311.505 (4)C526—H5260.9500
C431—C4321.397 (4)
C5—N1—N2112.1 (2)C433—C432—C431121.7 (3)
C5—N1—C11127.4 (2)C433—C432—H432119.1
N2—N1—C11119.5 (2)C431—C432—H432119.1
C3—N2—N1104.6 (2)C432—C433—C434118.1 (3)
N2—C3—C4112.4 (2)C432—C433—H433121.0
N2—C3—C31120.8 (2)C434—C433—H433121.0
C4—C3—C31126.9 (3)C435—C434—C433121.6 (3)
C5—C4—C3104.3 (2)C435—C434—Br44118.7 (2)
C5—C4—C41129.8 (3)C433—C434—Br44119.7 (2)
C3—C4—C41125.6 (3)C434—C435—C436119.3 (3)
N1—C5—N51125.5 (3)C434—C435—H435120.4
N1—C5—C4106.6 (2)C436—C435—H435120.4
N51—C5—C4127.8 (3)C435—C436—C431120.9 (3)
C16—C11—C12120.8 (3)C435—C436—H436119.6
C16—C11—N1119.5 (3)C431—C436—H436119.6
C12—C11—N1119.7 (3)C5—N51—C51115.7 (2)
C13—C12—C11118.9 (3)C5—N51—C52119.6 (2)
C13—C12—H12120.6C51—N51—C52114.8 (2)
C11—C12—H12120.6N51—C51—H51A109.5
C14—C13—C12120.4 (3)N51—C51—H51B109.5
C14—C13—H13119.8H51A—C51—H51B109.5
C12—C13—H13119.8N51—C51—H51C109.5
C13—C14—C15120.2 (3)H51A—C51—H51C109.5
C13—C14—H14119.9H51B—C51—H51C109.5
C15—C14—H14119.9N51—C52—C521110.5 (2)
C16—C15—C14119.8 (3)N51—C52—H52A109.5
C16—C15—H15120.1C521—C52—H52A109.5
C14—C15—H15120.1N51—C52—H52B109.5
C11—C16—C15119.9 (3)C521—C52—H52B109.5
C11—C16—H16120.0H52A—C52—H52B108.1
C15—C16—H16120.0C522—C521—C526119.3 (3)
C3—C31—H31A109.5C522—C521—C52121.0 (3)
C3—C31—H31B109.5C526—C521—C52119.7 (3)
H31A—C31—H31B109.5C521—C522—C523120.7 (3)
C3—C31—H31C109.5C521—C522—H522119.6
H31A—C31—H31C109.5C523—C522—H522119.6
H31B—C31—H31C109.5C522—C523—C524119.7 (3)
C42—C41—C4127.7 (3)C522—C523—H523120.1
C42—C41—H41116.2C524—C523—H523120.1
C4—C41—H41116.2C525—C524—C523120.0 (3)
C41—C42—C43120.7 (3)C525—C524—H524120.0
C41—C42—H42119.6C523—C524—H524120.0
C43—C42—H42119.6C524—C525—C526120.3 (3)
O43—C43—C42122.3 (3)C524—C525—H525119.9
O43—C43—C431119.6 (3)C526—C525—H525119.9
C42—C43—C431118.1 (2)C521—C526—C525120.0 (3)
C432—C431—C436118.4 (3)C521—C526—H526120.0
C432—C431—C43118.9 (3)C525—C526—H526120.0
C436—C431—C43122.7 (3)
C5—N1—N2—C31.1 (3)C41—C42—C43—C431161.2 (3)
C11—N1—N2—C3168.1 (3)O43—C43—C431—C43214.7 (4)
N1—N2—C3—C41.5 (3)C42—C43—C431—C432165.3 (3)
N1—N2—C3—C31177.9 (3)O43—C43—C431—C436163.2 (3)
N2—C3—C4—C51.3 (3)C42—C43—C431—C43616.9 (4)
C31—C3—C4—C5178.0 (3)C436—C431—C432—C4331.5 (5)
N2—C3—C4—C41172.4 (3)C43—C431—C432—C433179.4 (3)
C31—C3—C4—C418.3 (5)C431—C432—C433—C4340.9 (5)
N2—N1—C5—N51178.4 (3)C432—C433—C434—C4350.4 (5)
C11—N1—C5—N5113.4 (5)C432—C433—C434—Br44179.3 (2)
N2—N1—C5—C40.4 (3)C433—C434—C435—C4361.1 (5)
C11—N1—C5—C4167.8 (3)Br44—C434—C435—C436178.6 (2)
C3—C4—C5—N10.5 (3)C434—C435—C436—C4310.5 (5)
C41—C4—C5—N1172.8 (3)C432—C431—C436—C4350.8 (5)
C3—C4—C5—N51179.2 (3)C43—C431—C436—C435178.6 (3)
C41—C4—C5—N516.0 (5)N1—C5—N51—C51112.2 (3)
C5—N1—C11—C1656.2 (4)C4—C5—N51—C5169.3 (4)
N2—N1—C11—C16111.3 (3)N1—C5—N51—C5231.7 (4)
C5—N1—C11—C12123.3 (3)C4—C5—N51—C52146.8 (3)
N2—N1—C11—C1269.2 (3)C5—N51—C52—C521152.0 (3)
C16—C11—C12—C132.1 (4)C51—N51—C52—C52163.8 (4)
N1—C11—C12—C13177.4 (2)N51—C52—C521—C52257.3 (4)
C11—C12—C13—C140.2 (4)N51—C52—C521—C526122.8 (3)
C12—C13—C14—C151.9 (4)C526—C521—C522—C5230.7 (5)
C13—C14—C15—C161.2 (5)C52—C521—C522—C523179.2 (3)
C12—C11—C16—C152.8 (4)C521—C522—C523—C5240.9 (5)
N1—C11—C16—C15176.7 (3)C522—C523—C524—C5250.6 (5)
C14—C15—C16—C111.1 (5)C523—C524—C525—C5260.1 (5)
C5—C4—C41—C425.4 (5)C522—C521—C526—C5250.3 (5)
C3—C4—C41—C42166.5 (3)C52—C521—C526—C525179.7 (3)
C4—C41—C42—C43178.0 (3)C524—C525—C526—C5210.1 (5)
C41—C42—C43—O4318.8 (5)
(3RS)-5'-[Benzyl(methyl)amino]-3'-methyl-1',5-diphenyl-3,4-dihydro-1'H,2H-[3,4'-bipyrazole]-2-carbaldehyde (III) top
Crystal data top
C28H27N5OF(000) = 952
Mr = 449.55Dx = 1.292 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.321 (5) ÅCell parameters from 5340 reflections
b = 21.572 (13) Åθ = 2.4–27.6°
c = 9.550 (5) ŵ = 0.08 mm1
β = 97.711 (18)°T = 100 K
V = 2311 (2) Å3Block, colourless
Z = 40.15 × 0.12 × 0.10 mm
Data collection top
Bruker D8 Venture
diffractometer
5340 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube4632 reflections with I > 2σ(I)
Multilayer mirror monochromatorRint = 0.044
φ and ω scansθmax = 27.6°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS-2016/2; Bruker, 2016)
h = 1414
Tmin = 0.958, Tmax = 0.992k = 2828
55209 measured reflectionsl = 1212
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.0445P)2 + 1.086P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
5340 reflectionsΔρmax = 0.30 e Å3
309 parametersΔρmin = 0.29 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.80264 (8)0.37886 (4)0.45145 (10)0.01130 (19)
N20.89302 (8)0.40971 (5)0.39852 (10)0.0131 (2)
C30.84320 (10)0.43370 (5)0.27671 (12)0.0124 (2)
C40.72041 (10)0.41987 (5)0.25019 (11)0.0112 (2)
C50.69607 (9)0.38489 (5)0.36443 (11)0.0106 (2)
C110.83393 (9)0.34601 (5)0.58063 (11)0.0117 (2)
C120.91643 (10)0.37292 (6)0.68399 (12)0.0157 (2)
H120.94450.41380.67150.019*
C130.95754 (11)0.33982 (6)0.80550 (13)0.0211 (3)
H131.01440.35790.87590.025*
C140.91545 (11)0.28030 (7)0.82398 (14)0.0237 (3)
H140.94430.25740.90650.028*
C150.83127 (11)0.25443 (6)0.72181 (14)0.0215 (3)
H150.80140.21410.73580.026*
C160.79004 (10)0.28685 (5)0.59898 (12)0.0150 (2)
H160.73280.26880.52890.018*
C310.91846 (10)0.47178 (6)0.19176 (13)0.0175 (2)
H31A1.00030.47340.24030.026*
H31C0.88610.51390.18110.026*
H31B0.91810.45300.09830.026*
N410.70245 (9)0.48378 (5)0.07521 (10)0.0148 (2)
N420.66402 (9)0.43154 (4)0.00832 (10)0.0140 (2)
C420.66466 (11)0.37542 (5)0.07026 (12)0.0159 (2)
H420.69510.37220.15790.019*
O420.62793 (8)0.32863 (4)0.01887 (10)0.0210 (2)
C430.63066 (10)0.44466 (5)0.13454 (11)0.0121 (2)
H430.54990.42740.14270.015*
C440.62607 (10)0.51618 (5)0.13055 (12)0.0136 (2)
H44A0.54290.53140.12070.016*
H44B0.67140.53430.21670.016*
C450.68405 (10)0.53129 (5)0.00081 (12)0.0133 (2)
C4510.72318 (10)0.59351 (5)0.03545 (12)0.0151 (2)
C4520.80060 (11)0.60095 (6)0.13649 (13)0.0186 (2)
H4520.82540.56560.18430.022*
C4530.84159 (12)0.65907 (6)0.16787 (14)0.0231 (3)
H4530.89360.66370.23740.028*
C4540.80620 (12)0.71070 (6)0.09689 (14)0.0244 (3)
H4540.83510.75060.11700.029*
C4550.72883 (13)0.70409 (6)0.00313 (14)0.0238 (3)
H4550.70440.73960.05080.029*
C4560.68696 (12)0.64578 (6)0.03389 (13)0.0194 (3)
H4560.63370.64150.10210.023*
N510.58691 (8)0.36254 (5)0.39252 (10)0.0136 (2)
C510.52849 (10)0.31290 (6)0.30513 (13)0.0165 (2)
H51C0.55770.31270.21310.025*
H51B0.44210.31970.29160.025*
H51A0.54640.27290.35210.025*
C520.55016 (10)0.36967 (6)0.53234 (12)0.0151 (2)
H52A0.60430.39920.58830.018*
H52B0.55690.32920.58170.018*
C5210.42311 (10)0.39300 (5)0.52380 (12)0.0135 (2)
C5220.38815 (11)0.44714 (6)0.44973 (13)0.0172 (2)
H5220.44350.46860.40100.021*
C5230.27323 (11)0.46987 (6)0.44673 (13)0.0190 (3)
H5230.25090.50740.39800.023*
C5240.19055 (11)0.43807 (6)0.51468 (13)0.0197 (3)
H5240.11180.45360.51230.024*
C5250.22356 (11)0.38368 (6)0.58575 (14)0.0191 (3)
H5250.16700.36140.63100.023*
C5260.33977 (10)0.36144 (5)0.59120 (13)0.0154 (2)
H5260.36220.32430.64150.018*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0079 (4)0.0134 (4)0.0125 (4)0.0015 (3)0.0012 (3)0.0018 (4)
N20.0097 (4)0.0147 (5)0.0151 (5)0.0014 (4)0.0023 (4)0.0023 (4)
C30.0116 (5)0.0119 (5)0.0136 (5)0.0010 (4)0.0017 (4)0.0000 (4)
C40.0107 (5)0.0110 (5)0.0115 (5)0.0007 (4)0.0006 (4)0.0011 (4)
C50.0091 (5)0.0110 (5)0.0115 (5)0.0001 (4)0.0003 (4)0.0023 (4)
C110.0091 (5)0.0148 (5)0.0112 (5)0.0027 (4)0.0022 (4)0.0013 (4)
C120.0121 (5)0.0191 (6)0.0156 (5)0.0023 (4)0.0013 (4)0.0007 (4)
C130.0137 (5)0.0338 (7)0.0148 (6)0.0018 (5)0.0016 (4)0.0036 (5)
C140.0176 (6)0.0346 (7)0.0184 (6)0.0019 (5)0.0010 (5)0.0137 (5)
C150.0177 (6)0.0225 (6)0.0248 (6)0.0007 (5)0.0048 (5)0.0100 (5)
C160.0119 (5)0.0160 (5)0.0170 (6)0.0003 (4)0.0021 (4)0.0013 (4)
C310.0127 (5)0.0214 (6)0.0183 (6)0.0018 (4)0.0019 (4)0.0055 (5)
N410.0167 (5)0.0142 (5)0.0128 (5)0.0015 (4)0.0003 (4)0.0019 (4)
N420.0178 (5)0.0130 (5)0.0109 (4)0.0011 (4)0.0012 (4)0.0004 (4)
C420.0169 (6)0.0161 (6)0.0139 (5)0.0036 (4)0.0004 (4)0.0024 (4)
O420.0266 (5)0.0142 (4)0.0223 (5)0.0004 (3)0.0035 (4)0.0015 (3)
C430.0113 (5)0.0138 (5)0.0110 (5)0.0019 (4)0.0005 (4)0.0009 (4)
C440.0138 (5)0.0130 (5)0.0134 (5)0.0031 (4)0.0001 (4)0.0001 (4)
C450.0122 (5)0.0154 (5)0.0113 (5)0.0030 (4)0.0024 (4)0.0012 (4)
C4510.0154 (5)0.0150 (5)0.0134 (5)0.0019 (4)0.0036 (4)0.0014 (4)
C4520.0174 (6)0.0188 (6)0.0190 (6)0.0002 (5)0.0005 (5)0.0005 (5)
C4530.0214 (6)0.0249 (7)0.0227 (6)0.0028 (5)0.0020 (5)0.0047 (5)
C4540.0278 (7)0.0170 (6)0.0265 (7)0.0032 (5)0.0034 (5)0.0068 (5)
C4550.0331 (7)0.0144 (6)0.0224 (6)0.0043 (5)0.0019 (5)0.0007 (5)
C4560.0249 (6)0.0169 (6)0.0157 (6)0.0039 (5)0.0007 (5)0.0022 (5)
N510.0097 (4)0.0189 (5)0.0126 (5)0.0042 (4)0.0027 (4)0.0031 (4)
C510.0140 (5)0.0168 (6)0.0185 (6)0.0045 (4)0.0013 (4)0.0029 (4)
C520.0114 (5)0.0219 (6)0.0122 (5)0.0007 (4)0.0021 (4)0.0000 (4)
C5210.0110 (5)0.0172 (5)0.0123 (5)0.0020 (4)0.0013 (4)0.0045 (4)
C5220.0154 (5)0.0192 (6)0.0170 (6)0.0041 (4)0.0017 (4)0.0003 (5)
C5230.0183 (6)0.0176 (6)0.0200 (6)0.0012 (5)0.0021 (5)0.0024 (5)
C5240.0122 (5)0.0239 (6)0.0226 (6)0.0012 (5)0.0009 (5)0.0103 (5)
C5250.0147 (6)0.0206 (6)0.0236 (6)0.0048 (5)0.0082 (5)0.0066 (5)
C5260.0155 (5)0.0142 (5)0.0172 (5)0.0025 (4)0.0049 (4)0.0035 (4)
Geometric parameters (Å, º) top
N1—N21.3726 (14)C44—H44B0.9900
N1—C51.3762 (15)C45—C4511.4691 (18)
N1—C111.4256 (15)C451—C4561.3968 (18)
N2—C31.3279 (16)C451—C4521.3972 (18)
C3—C41.4111 (16)C452—C4531.3835 (19)
C3—C311.4981 (16)C452—H4520.9500
C4—C51.3844 (16)C453—C4541.390 (2)
C4—C431.4957 (16)C453—H4530.9500
C5—N511.3859 (15)C454—C4551.387 (2)
C11—C161.3890 (17)C454—H4540.9500
C11—C121.3915 (17)C455—C4561.3895 (19)
C12—C131.3886 (18)C455—H4550.9500
C12—H120.9500C456—H4560.9500
C13—C141.389 (2)N51—C521.4591 (16)
C13—H130.9500N51—C511.4604 (16)
C14—C151.386 (2)C51—H51C0.9800
C14—H140.9500C51—H51B0.9800
C15—C161.3914 (18)C51—H51A0.9800
C15—H150.9500C52—C5211.5156 (17)
C16—H160.9500C52—H52A0.9900
C31—H31A0.9800C52—H52B0.9900
C31—H31C0.9800C521—C5261.3895 (17)
C31—H31B0.9800C521—C5221.3950 (18)
N41—C451.2890 (16)C522—C5231.3871 (18)
N41—N421.3934 (15)C522—H5220.9500
N42—C421.3480 (16)C523—C5241.3895 (19)
N42—C431.4908 (16)C523—H5230.9500
C42—O421.2195 (16)C524—C5251.382 (2)
C42—H420.9500C524—H5240.9500
C43—C441.5440 (18)C525—C5261.3947 (18)
C43—H431.0000C525—H5250.9500
C44—C451.5135 (17)C526—H5260.9500
C44—H44A0.9900
N2—N1—C5111.60 (9)H44A—C44—H44B109.2
N2—N1—C11116.66 (9)N41—C45—C451121.14 (11)
C5—N1—C11131.72 (9)N41—C45—C44114.23 (11)
C3—N2—N1105.17 (9)C451—C45—C44124.56 (10)
N2—C3—C4111.54 (10)C456—C451—C452119.07 (12)
N2—C3—C31118.85 (10)C456—C451—C45120.58 (11)
C4—C3—C31129.56 (10)C452—C451—C45120.31 (11)
C5—C4—C3105.62 (10)C453—C452—C451120.90 (12)
C5—C4—C43126.12 (10)C453—C452—H452119.6
C3—C4—C43127.75 (10)C451—C452—H452119.6
N1—C5—C4106.04 (10)C452—C453—C454119.56 (13)
N1—C5—N51125.63 (10)C452—C453—H453120.2
C4—C5—N51128.25 (10)C454—C453—H453120.2
C16—C11—C12120.74 (11)C455—C454—C453120.21 (12)
C16—C11—N1120.95 (10)C455—C454—H454119.9
C12—C11—N1118.14 (11)C453—C454—H454119.9
C13—C12—C11119.73 (12)C454—C455—C456120.22 (12)
C13—C12—H12120.1C454—C455—H455119.9
C11—C12—H12120.1C456—C455—H455119.9
C12—C13—C14119.96 (12)C455—C456—C451120.03 (12)
C12—C13—H13120.0C455—C456—H456120.0
C14—C13—H13120.0C451—C456—H456120.0
C15—C14—C13119.85 (12)C5—N51—C52120.77 (9)
C15—C14—H14120.1C5—N51—C51119.46 (9)
C13—C14—H14120.1C52—N51—C51115.94 (9)
C14—C15—C16120.80 (12)N51—C51—H51C109.5
C14—C15—H15119.6N51—C51—H51B109.5
C16—C15—H15119.6H51C—C51—H51B109.5
C11—C16—C15118.88 (11)N51—C51—H51A109.5
C11—C16—H16120.6H51C—C51—H51A109.5
C15—C16—H16120.6H51B—C51—H51A109.5
C3—C31—H31A109.5N51—C52—C521111.77 (10)
C3—C31—H31C109.5N51—C52—H52A109.3
H31A—C31—H31C109.5C521—C52—H52A109.3
C3—C31—H31B109.5N51—C52—H52B109.3
H31A—C31—H31B109.5C521—C52—H52B109.3
H31C—C31—H31B109.5H52A—C52—H52B107.9
C45—N41—N42107.51 (10)C526—C521—C522118.75 (11)
C42—N42—N41120.32 (10)C526—C521—C52120.73 (11)
C42—N42—C43126.09 (10)C522—C521—C52120.52 (10)
N41—N42—C43113.52 (9)C523—C522—C521120.53 (11)
O42—C42—N42122.99 (12)C523—C522—H522119.7
O42—C42—H42118.5C521—C522—H522119.7
N42—C42—H42118.5C522—C523—C524120.30 (12)
N42—C43—C4112.18 (9)C522—C523—H523119.8
N42—C43—C44100.30 (9)C524—C523—H523119.8
C4—C43—C44113.13 (9)C525—C524—C523119.59 (11)
N42—C43—H43110.3C525—C524—H524120.2
C4—C43—H43110.3C523—C524—H524120.2
C44—C43—H43110.3C524—C525—C526120.14 (11)
C45—C44—C43102.63 (9)C524—C525—H525119.9
C45—C44—H44A111.2C526—C525—H525119.9
C43—C44—H44A111.2C521—C526—C525120.66 (12)
C45—C44—H44B111.2C521—C526—H526119.7
C43—C44—H44B111.2C525—C526—H526119.7
C5—N1—N2—C31.47 (12)C3—C4—C43—N4257.71 (15)
C11—N1—N2—C3177.20 (9)C5—C4—C43—C44115.77 (12)
N1—N2—C3—C41.05 (12)C3—C4—C43—C4454.88 (15)
N1—N2—C3—C31178.99 (10)N42—C43—C44—C4512.20 (10)
N2—C3—C4—C50.29 (13)C4—C43—C44—C45107.47 (11)
C31—C3—C4—C5177.94 (11)N42—N41—C45—C451175.48 (10)
N2—C3—C4—C43171.88 (10)N42—N41—C45—C441.53 (13)
C31—C3—C4—C435.77 (19)C43—C44—C45—N419.44 (13)
N2—N1—C5—C41.31 (12)C43—C44—C45—C451167.45 (10)
C11—N1—C5—C4177.10 (11)N41—C45—C451—C456170.03 (11)
N2—N1—C5—N51175.71 (10)C44—C45—C451—C45613.28 (17)
C11—N1—C5—N515.89 (19)N41—C45—C451—C45212.20 (17)
C3—C4—C5—N10.60 (12)C44—C45—C451—C452164.49 (11)
C43—C4—C5—N1172.94 (10)C456—C451—C452—C4530.19 (18)
C3—C4—C5—N51176.31 (11)C45—C451—C452—C453177.61 (11)
C43—C4—C5—N513.97 (19)C451—C452—C453—C4540.64 (19)
N2—N1—C11—C16136.73 (11)C452—C453—C454—C4551.0 (2)
C5—N1—C11—C1641.61 (17)C453—C454—C455—C4560.5 (2)
N2—N1—C11—C1238.68 (14)C454—C455—C456—C4510.31 (19)
C5—N1—C11—C12142.99 (12)C452—C451—C456—C4550.66 (18)
C16—C11—C12—C131.50 (17)C45—C451—C456—C455177.13 (11)
N1—C11—C12—C13173.92 (10)N1—C5—N51—C5243.55 (16)
C11—C12—C13—C140.60 (18)C4—C5—N51—C52132.80 (13)
C12—C13—C14—C150.84 (19)N1—C5—N51—C51113.52 (13)
C13—C14—C15—C161.4 (2)C4—C5—N51—C5170.13 (16)
C12—C11—C16—C150.94 (17)C5—N51—C52—C521133.46 (11)
N1—C11—C16—C15174.34 (10)C51—N51—C52—C52168.70 (13)
C14—C15—C16—C110.51 (18)N51—C52—C521—C526126.73 (12)
C45—N41—N42—C42175.13 (10)N51—C52—C521—C52254.22 (15)
C45—N41—N42—C437.81 (13)C526—C521—C522—C5231.72 (17)
N41—N42—C42—O42177.22 (11)C52—C521—C522—C523177.35 (11)
C43—N42—C42—O426.11 (19)C521—C522—C523—C5241.62 (18)
C42—N42—C43—C469.45 (14)C522—C523—C524—C5250.19 (18)
N41—N42—C43—C4107.41 (11)C523—C524—C525—C5261.09 (18)
C42—N42—C43—C44170.20 (11)C522—C521—C526—C5250.43 (17)
N41—N42—C43—C4412.94 (11)C52—C521—C526—C525178.63 (11)
C5—C4—C43—N42131.64 (12)C524—C525—C526—C5210.97 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···O42i0.952.433.207 (2)139
C44—H44A···N42ii0.992.573.520 (3)161
C44—H44B···Cg2iii0.992.733.646 (3)154
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y+1, z; (iii) x+1, y+1, z+1.
(3RS)-2-acetyl-5'-[Benzyl(methyl)amino]- 5-(4-methoxyphenyl)-3'-methyl-1'-phenyl-3,4-dihydro-1'H,2H-[3,4'-bipyrazole] ethanol 0.945-solvate (IV) top
Crystal data top
C30H31N5O2·0.945C2H6OF(000) = 1146.3
Mr = 537.13Dx = 1.262 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 9.363 (6) ÅCell parameters from 6555 reflections
b = 28.238 (18) Åθ = 2.3–27.6°
c = 10.775 (7) ŵ = 0.08 mm1
β = 97.04 (2)°T = 100 K
V = 2827 (3) Å3Plate, colourless
Z = 40.42 × 0.28 × 0.21 mm
Data collection top
Bruker D8 Venture
diffractometer
6550 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube5518 reflections with I > 2σ(I)
Multilayer mirror monochromatorRint = 0.047
φ and ω scansθmax = 27.6°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS-2016/2; Bruker, 2016)
h = 1212
Tmin = 0.940, Tmax = 0.983k = 3636
65713 measured reflectionsl = 1413
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.104 w = 1/[σ2(Fo2) + (0.043P)2 + 1.4625P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
6550 reflectionsΔρmax = 0.39 e Å3
370 parametersΔρmin = 0.31 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.45887 (11)0.66068 (4)0.55283 (10)0.0118 (2)
N20.60332 (11)0.65210 (4)0.57673 (10)0.0131 (2)
C30.61856 (13)0.62404 (4)0.67664 (11)0.0120 (2)
C40.48428 (13)0.61354 (4)0.71737 (11)0.0117 (2)
C50.38381 (13)0.63719 (4)0.63553 (11)0.0113 (2)
C110.40917 (13)0.69361 (4)0.45724 (11)0.0120 (2)
C120.47304 (14)0.69383 (4)0.34750 (12)0.0160 (3)
H120.54460.67110.33500.019*
C130.43171 (15)0.72751 (5)0.25611 (13)0.0198 (3)
H130.47620.72810.18150.024*
C140.32558 (15)0.76031 (5)0.27366 (13)0.0193 (3)
H140.29710.78320.21090.023*
C150.26125 (14)0.75956 (4)0.38278 (13)0.0168 (3)
H150.18800.78180.39420.020*
C160.30301 (13)0.72644 (4)0.47576 (12)0.0141 (2)
H160.25960.72620.55100.017*
C310.76666 (13)0.60815 (5)0.72900 (12)0.0162 (3)
H31A0.83550.61740.67180.024*
H31B0.76760.57360.73880.024*
H31C0.79360.62310.81060.024*
N410.65277 (11)0.55646 (4)0.97537 (10)0.0141 (2)
N420.55980 (11)0.59324 (4)0.93773 (10)0.0139 (2)
C420.56746 (14)0.63518 (4)0.99967 (12)0.0152 (3)
O420.48177 (10)0.66698 (3)0.96734 (9)0.0198 (2)
C4210.68645 (16)0.63970 (5)1.10638 (13)0.0211 (3)
H42A0.68100.67081.14560.032*
H42B0.77970.63631.07470.032*
H42C0.67610.61491.16820.032*
C430.45776 (13)0.58227 (4)0.82489 (11)0.0129 (2)
H430.35650.58620.84370.015*
C440.49061 (13)0.52927 (4)0.80662 (12)0.0141 (2)
H44A0.40800.50920.82210.017*
H44B0.51500.52300.72130.017*
C450.61830 (13)0.52086 (4)0.90363 (11)0.0127 (2)
C4510.70203 (13)0.47705 (4)0.91853 (12)0.0133 (2)
C4520.83001 (14)0.47552 (4)1.00111 (12)0.0155 (3)
H4520.86220.50321.04640.019*
C4530.90954 (14)0.43456 (5)1.01745 (13)0.0174 (3)
H4530.99720.43431.07220.021*
C4540.86160 (14)0.39350 (4)0.95366 (13)0.0169 (3)
O4540.94401 (11)0.35436 (3)0.98203 (10)0.0232 (2)
C4570.88438 (18)0.31013 (5)0.93698 (17)0.0315 (4)
H47A0.78780.30650.96190.047*
H47B0.94590.28420.97250.047*
H47C0.87850.30930.84560.047*
C4550.73640 (14)0.39432 (4)0.86971 (13)0.0177 (3)
H4550.70470.36660.82460.021*
C4560.65808 (14)0.43616 (4)0.85248 (12)0.0152 (3)
H4560.57300.43680.79460.018*
N510.23382 (11)0.63971 (4)0.62052 (10)0.0137 (2)
C510.16379 (14)0.64632 (5)0.73287 (13)0.0184 (3)
H51A0.14380.61540.76800.028*
H51B0.07330.66360.71160.028*
H51C0.22720.66450.79450.028*
C520.16039 (14)0.60761 (5)0.52478 (12)0.0167 (3)
H52B0.19540.61460.44370.020*
H52A0.05600.61450.51550.020*
C5210.18179 (14)0.55537 (5)0.55248 (12)0.0164 (3)
C5220.28431 (15)0.52961 (5)0.49705 (13)0.0203 (3)
H5220.34190.54520.44290.024*
C5230.30349 (16)0.48159 (5)0.51976 (14)0.0248 (3)
H5230.37360.46460.48110.030*
C5240.22047 (17)0.45832 (5)0.59887 (14)0.0252 (3)
H5240.23320.42540.61430.030*
C5250.11873 (16)0.48346 (5)0.65534 (14)0.0241 (3)
H5250.06240.46780.71030.029*
C5260.09895 (15)0.53146 (5)0.63177 (13)0.0199 (3)
H5260.02810.54830.67010.024*
O610.83673 (12)0.66224 (4)0.43191 (11)0.0236 (3)0.945 (3)
H610.767 (2)0.6631 (7)0.473 (2)0.035*0.945 (3)
C610.89741 (19)0.70840 (6)0.43365 (16)0.0317 (4)0.945 (3)
H61A1.00310.70590.45400.038*0.945 (3)
H61B0.86060.72710.50070.038*0.945 (3)
C620.86449 (18)0.73404 (5)0.31345 (15)0.0253 (4)0.945 (3)
H62A0.89840.71540.24610.038*0.945 (3)
H62B0.91300.76490.31920.038*0.945 (3)
H62C0.76030.73880.29560.038*0.945 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0090 (5)0.0128 (5)0.0136 (5)0.0001 (4)0.0013 (4)0.0025 (4)
N20.0089 (5)0.0149 (5)0.0152 (5)0.0008 (4)0.0007 (4)0.0019 (4)
C30.0116 (6)0.0117 (5)0.0126 (6)0.0002 (4)0.0015 (4)0.0000 (4)
C40.0113 (6)0.0109 (5)0.0130 (6)0.0001 (4)0.0016 (4)0.0001 (4)
C50.0111 (6)0.0099 (5)0.0130 (6)0.0006 (4)0.0022 (4)0.0001 (4)
C110.0116 (6)0.0102 (5)0.0136 (6)0.0021 (4)0.0008 (5)0.0011 (4)
C120.0158 (6)0.0160 (6)0.0162 (6)0.0029 (5)0.0026 (5)0.0014 (5)
C130.0223 (7)0.0221 (7)0.0157 (6)0.0028 (5)0.0046 (5)0.0053 (5)
C140.0225 (7)0.0157 (6)0.0187 (6)0.0020 (5)0.0011 (5)0.0063 (5)
C150.0166 (6)0.0112 (6)0.0222 (7)0.0023 (5)0.0002 (5)0.0009 (5)
C160.0149 (6)0.0127 (6)0.0150 (6)0.0004 (5)0.0025 (5)0.0014 (5)
C310.0108 (6)0.0194 (6)0.0180 (6)0.0013 (5)0.0010 (5)0.0045 (5)
N410.0156 (5)0.0128 (5)0.0137 (5)0.0012 (4)0.0013 (4)0.0036 (4)
N420.0154 (5)0.0130 (5)0.0129 (5)0.0022 (4)0.0001 (4)0.0017 (4)
C420.0181 (6)0.0145 (6)0.0144 (6)0.0021 (5)0.0074 (5)0.0005 (5)
O420.0230 (5)0.0143 (4)0.0230 (5)0.0026 (4)0.0063 (4)0.0014 (4)
C4210.0253 (7)0.0192 (6)0.0183 (7)0.0013 (5)0.0011 (5)0.0048 (5)
C430.0118 (6)0.0139 (6)0.0129 (6)0.0009 (4)0.0012 (5)0.0022 (4)
C440.0151 (6)0.0125 (6)0.0143 (6)0.0007 (4)0.0002 (5)0.0023 (4)
C450.0134 (6)0.0128 (6)0.0123 (6)0.0019 (4)0.0029 (5)0.0034 (4)
C4510.0136 (6)0.0129 (6)0.0137 (6)0.0004 (5)0.0032 (5)0.0035 (4)
C4520.0153 (6)0.0133 (6)0.0177 (6)0.0022 (5)0.0007 (5)0.0025 (5)
C4530.0127 (6)0.0178 (6)0.0210 (7)0.0005 (5)0.0002 (5)0.0049 (5)
C4540.0157 (6)0.0139 (6)0.0219 (7)0.0030 (5)0.0062 (5)0.0045 (5)
O4540.0191 (5)0.0149 (5)0.0350 (6)0.0054 (4)0.0018 (4)0.0017 (4)
C4570.0303 (8)0.0144 (7)0.0486 (10)0.0068 (6)0.0002 (7)0.0032 (6)
C4550.0200 (6)0.0135 (6)0.0199 (6)0.0013 (5)0.0039 (5)0.0013 (5)
C4560.0146 (6)0.0163 (6)0.0144 (6)0.0010 (5)0.0007 (5)0.0019 (5)
N510.0086 (5)0.0152 (5)0.0172 (5)0.0001 (4)0.0009 (4)0.0015 (4)
C510.0130 (6)0.0185 (6)0.0248 (7)0.0001 (5)0.0065 (5)0.0012 (5)
C520.0113 (6)0.0199 (6)0.0181 (6)0.0021 (5)0.0021 (5)0.0024 (5)
C5210.0134 (6)0.0190 (6)0.0153 (6)0.0025 (5)0.0035 (5)0.0015 (5)
C5220.0170 (6)0.0265 (7)0.0170 (6)0.0006 (5)0.0002 (5)0.0034 (5)
C5230.0242 (7)0.0264 (7)0.0223 (7)0.0056 (6)0.0034 (6)0.0094 (6)
C5240.0318 (8)0.0164 (6)0.0241 (7)0.0002 (6)0.0093 (6)0.0040 (5)
C5250.0288 (8)0.0209 (7)0.0216 (7)0.0086 (6)0.0005 (6)0.0007 (5)
C5260.0192 (7)0.0197 (6)0.0208 (7)0.0039 (5)0.0024 (5)0.0036 (5)
O610.0191 (6)0.0207 (6)0.0333 (7)0.0006 (4)0.0125 (5)0.0068 (4)
C610.0342 (9)0.0342 (9)0.0248 (8)0.0177 (7)0.0048 (7)0.0063 (7)
C620.0276 (8)0.0189 (7)0.0277 (8)0.0060 (6)0.0031 (6)0.0013 (6)
Geometric parameters (Å, º) top
N1—N21.3671 (16)C452—C4531.3751 (19)
N1—C51.3716 (16)C452—H4520.9500
N1—C111.4228 (16)C453—C4541.394 (2)
N2—C31.3302 (17)C453—H4530.9500
C3—C41.4130 (18)C454—O4541.3610 (16)
C3—C311.5002 (19)C454—C4551.390 (2)
C4—C51.3803 (18)O454—C4571.4285 (19)
C4—C431.5014 (18)C457—H47A0.9800
C5—N511.3956 (18)C457—H47B0.9800
C11—C121.3889 (19)C457—H47C0.9800
C11—C161.3915 (18)C455—C4561.3909 (19)
C12—C131.3894 (19)C455—H4550.9500
C12—H120.9500C456—H4560.9500
C13—C141.388 (2)N51—C511.4578 (18)
C13—H130.9500N51—C521.4781 (18)
C14—C151.385 (2)C51—H51A0.9800
C14—H140.9500C51—H51B0.9800
C15—C161.3910 (19)C51—H51C0.9800
C15—H150.9500C52—C5211.513 (2)
C16—H160.9500C52—H52B0.9900
C31—H31A0.9800C52—H52A0.9900
C31—H31B0.9800C521—C5221.3956 (19)
C31—H31C0.9800C521—C5261.3965 (19)
N41—C451.2849 (17)C522—C5231.386 (2)
N41—N421.3836 (15)C522—H5220.9500
N42—C421.3569 (17)C523—C5241.387 (2)
N42—C431.4840 (18)C523—H5230.9500
C42—O421.2261 (17)C524—C5251.387 (2)
C42—C4211.505 (2)C524—H5240.9500
C421—H42A0.9800C525—C5261.387 (2)
C421—H42B0.9800C525—H5250.9500
C421—H42C0.9800C526—H5260.9500
C43—C441.5453 (19)O61—C611.421 (2)
C43—H431.0000O61—H610.83 (2)
C44—C451.5074 (19)C61—C621.483 (2)
C44—H44A0.9900C61—H61A0.9900
C44—H44B0.9900C61—H61B0.9900
C45—C4511.4629 (18)C62—H62A0.9800
C451—C4561.3918 (19)C62—H62B0.9800
C451—C4521.4028 (19)C62—H62C0.9800
N2—N1—C5111.46 (10)C453—C452—C451120.94 (12)
N2—N1—C11118.71 (10)C453—C452—H452119.5
C5—N1—C11129.65 (11)C451—C452—H452119.5
C3—N2—N1105.28 (10)C452—C453—C454119.99 (13)
N2—C3—C4111.41 (11)C452—C453—H453120.0
N2—C3—C31119.01 (11)C454—C453—H453120.0
C4—C3—C31129.57 (12)O454—C454—C455124.70 (12)
C5—C4—C3105.23 (11)O454—C454—C453115.17 (12)
C5—C4—C43127.83 (11)C455—C454—C453120.12 (12)
C3—C4—C43126.92 (11)C454—O454—C457116.51 (12)
N1—C5—C4106.60 (11)O454—C457—H47A109.5
N1—C5—N51119.24 (11)O454—C457—H47B109.5
C4—C5—N51134.10 (11)H47A—C457—H47B109.5
C12—C11—C16120.57 (11)O454—C457—H47C109.5
C12—C11—N1118.86 (11)H47A—C457—H47C109.5
C16—C11—N1120.51 (11)H47B—C457—H47C109.5
C11—C12—C13119.67 (12)C454—C455—C456119.32 (12)
C11—C12—H12120.2C454—C455—H455120.3
C13—C12—H12120.2C456—C455—H455120.3
C14—C13—C12120.13 (13)C455—C456—C451121.22 (13)
C14—C13—H13119.9C455—C456—H456119.4
C12—C13—H13119.9C451—C456—H456119.4
C15—C14—C13119.88 (12)C5—N51—C51117.32 (11)
C15—C14—H14120.1C5—N51—C52115.16 (10)
C13—C14—H14120.1C51—N51—C52116.11 (11)
C14—C15—C16120.56 (12)N51—C51—H51A109.5
C14—C15—H15119.7N51—C51—H51B109.5
C16—C15—H15119.7H51A—C51—H51B109.5
C15—C16—C11119.17 (12)N51—C51—H51C109.5
C15—C16—H16120.4H51A—C51—H51C109.5
C11—C16—H16120.4H51B—C51—H51C109.5
C3—C31—H31A109.5N51—C52—C521114.90 (11)
C3—C31—H31B109.5N51—C52—H52B108.5
H31A—C31—H31B109.5C521—C52—H52B108.5
C3—C31—H31C109.5N51—C52—H52A108.5
H31A—C31—H31C109.5C521—C52—H52A108.5
H31B—C31—H31C109.5H52B—C52—H52A107.5
C45—N41—N42107.95 (11)C522—C521—C526118.19 (13)
C42—N42—N41121.16 (11)C522—C521—C52120.33 (12)
C42—N42—C43125.10 (11)C526—C521—C52121.46 (12)
N41—N42—C43113.72 (10)C523—C522—C521121.03 (13)
O42—C42—N42120.42 (13)C523—C522—H522119.5
O42—C42—C421123.52 (12)C521—C522—H522119.5
N42—C42—C421116.06 (11)C522—C523—C524120.12 (14)
C42—C421—H42A109.5C522—C523—H523119.9
C42—C421—H42B109.5C524—C523—H523119.9
H42A—C421—H42B109.5C525—C524—C523119.58 (14)
C42—C421—H42C109.5C525—C524—H524120.2
H42A—C421—H42C109.5C523—C524—H524120.2
H42B—C421—H42C109.5C524—C525—C526120.22 (14)
N42—C43—C4111.02 (11)C524—C525—H525119.9
N42—C43—C44100.86 (9)C526—C525—H525119.9
C4—C43—C44114.64 (11)C525—C526—C521120.85 (13)
N42—C43—H43110.0C525—C526—H526119.6
C4—C43—H43110.0C521—C526—H526119.6
C44—C43—H43110.0C61—O61—H61107.7 (14)
C45—C44—C43102.56 (10)O61—C61—C62113.35 (13)
C45—C44—H44A111.3O61—C61—H61A108.9
C43—C44—H44A111.3C62—C61—H61A108.9
C45—C44—H44B111.3O61—C61—H61B108.9
C43—C44—H44B111.3C62—C61—H61B108.9
H44A—C44—H44B109.2H61A—C61—H61B107.7
N41—C45—C451120.26 (12)C61—C62—H62A109.5
N41—C45—C44114.42 (11)C61—C62—H62B109.5
C451—C45—C44125.32 (11)H62A—C62—H62B109.5
C456—C451—C452118.35 (11)C61—C62—H62C109.5
C456—C451—C45121.64 (12)H62A—C62—H62C109.5
C452—C451—C45120.01 (11)H62B—C62—H62C109.5
C5—N1—N2—C31.44 (13)C5—C4—C43—C44111.42 (14)
C11—N1—N2—C3174.15 (10)C3—C4—C43—C4466.88 (16)
N1—N2—C3—C40.91 (13)N42—C43—C44—C456.45 (11)
N1—N2—C3—C31179.33 (10)C4—C43—C44—C45112.88 (12)
N2—C3—C4—C50.08 (14)N42—N41—C45—C451177.77 (10)
C31—C3—C4—C5179.80 (12)N42—N41—C45—C441.31 (14)
N2—C3—C4—C43178.53 (11)C43—C44—C45—N415.28 (14)
C31—C3—C4—C431.2 (2)C43—C44—C45—C451173.74 (11)
N2—N1—C5—C41.42 (13)N41—C45—C451—C456172.45 (12)
C11—N1—C5—C4173.56 (11)C44—C45—C451—C4568.59 (18)
N2—N1—C5—N51176.32 (10)N41—C45—C451—C4527.49 (18)
C11—N1—C5—N518.70 (18)C44—C45—C451—C452171.47 (11)
C3—C4—C5—N10.79 (13)C456—C451—C452—C4530.61 (18)
C43—C4—C5—N1179.38 (11)C45—C451—C452—C453179.33 (12)
C3—C4—C5—N51176.46 (13)C451—C452—C453—C4541.47 (19)
C43—C4—C5—N512.1 (2)C452—C453—C454—O454176.38 (12)
N2—N1—C11—C1239.84 (16)C452—C453—C454—C4552.55 (19)
C5—N1—C11—C12145.49 (13)C455—C454—O454—C45710.30 (19)
N2—N1—C11—C16137.24 (12)C453—C454—O454—C457168.58 (13)
C5—N1—C11—C1637.43 (18)O454—C454—C455—C456177.30 (12)
C16—C11—C12—C130.77 (19)C453—C454—C455—C4561.52 (19)
N1—C11—C12—C13176.30 (12)C454—C455—C456—C4510.59 (19)
C11—C12—C13—C141.0 (2)C452—C451—C456—C4551.65 (18)
C12—C13—C14—C150.3 (2)C45—C451—C456—C455178.29 (12)
C13—C14—C15—C160.6 (2)N1—C5—N51—C51137.53 (12)
C14—C15—C16—C110.80 (19)C4—C5—N51—C5145.49 (19)
C12—C11—C16—C150.10 (18)N1—C5—N51—C5280.31 (14)
N1—C11—C16—C15177.13 (11)C4—C5—N51—C5296.67 (17)
C45—N41—N42—C42177.72 (11)C5—N51—C52—C52164.11 (14)
C45—N41—N42—C433.64 (14)C51—N51—C52—C52178.52 (14)
N41—N42—C42—O42177.97 (11)N51—C52—C521—C52298.83 (15)
C43—N42—C42—O423.55 (19)N51—C52—C521—C52682.24 (16)
N41—N42—C42—C4212.79 (17)C526—C521—C522—C5230.1 (2)
C43—N42—C42—C421175.69 (11)C52—C521—C522—C523178.88 (12)
C42—N42—C43—C463.24 (15)C521—C522—C523—C5240.2 (2)
N41—N42—C43—C4115.34 (12)C522—C523—C524—C5250.3 (2)
C42—N42—C43—C44174.86 (11)C523—C524—C525—C5260.7 (2)
N41—N42—C43—C446.57 (12)C524—C525—C526—C5210.8 (2)
C5—C4—C43—N42135.11 (13)C522—C521—C526—C5250.4 (2)
C3—C4—C43—N4246.59 (16)C52—C521—C526—C525179.34 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O61—H61···N20.83 (2)2.03 (2)2.851 (2)169.4 (19)
C52—H52A···O61i0.992.533.438 (3)153
C524—H524···O61ii0.952.593.456 (3)151
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1, z+1.
Selected geometric parameters (Å, °) for compounds (I)–(IV) top
Parameter(I)(II)(III)(IV)
N1-N21.3931 (15)1.393 (3)1.3726 (14)1.3671 (16)
N2-C31.3135 (16)1.327 (4)1.3279 (16)1.3302 (17)
C3-C41.4227 (17)1.432 (4)1.4111 (16)1.4130 (18)
C4-C51.4077 (17)1.408 (4)1.3844 (16)1.3803 (18)
C5-N11.3571 (16)1.365 (4)1.3762 (15)1.3716 (16)
C4-C411.4334 (16)1.447 (4)
C41-O411.2196 (16)
C41-C421.355 (4)
C42-C431.475 (4)
C43-O431.231 (3)
N41-N421.3934 (15)1.3836 (15)
N42-C421.3480 (16)1.3569 (17)
C42-O421.2195 (16)1.2261 (17)
C5-N511.3584 (16)1.399 (4)1.3859 (15)1.3956 (18)
C453-C454-O454115.17 (12)
C455-C454-O454124.70 (12)
N2-N1-C11-C1258.32 (15)69.2 (3)38.68 (14)39.84 (16)
N1-C5-N51-C52-134.32 (12)31.7 (4)43.55 (16)-137.53 (12)
C5-C4-C41-O41-6.0 (2)
C5-C4-C41-C425.4 (5)
C5-N51-C52-C52189.82 (13)152.0 (3)133.46 (11)64.11 (14)
N51-C52-C521-C522-87.50 (14)-57.3 (4)-54.22 (15)-98.83 (15)
N41-N42-C42-O42-177.22 (11)-177.97 (11)
N41-C45-C451-C452-12.20 (17)-7.49 (18)
C453-C454-O454-C457168.58 (13)
Hydrogen bond parameters(Å, °) for compounds (I)–(IV) top
CompoundD-H···AD-HH···AD···AD-H···A
(I)C52-H52A···N2i0.992.513,402 (2)150
C526-H526···Cg1i0.952.743.584 (2)148
(III)C16-H16···O42ii0.952.433.207 (2)139
C44-H44A···N42iii0.992.573.520 (3)161
C44-H44B···Cg2iv0.992.733.646 (3)154
(IV)O61-H61···N20.83 (2)2.03 (2)2.851 (2)169.4 (19)
C52-H52A···O61i0.992.533.438 (3)153
C524-H524···O61iv0.952.593.456 (3)151
Cg1 represents the centroid of the C11–C16 ring and Cg2 represents the centroid of the C521–C526 ring. Symmetry codes: (i) -1 + x, y, z; (ii) x, 0.5 - y, 0.5 + z; (iii) 1 - x, 1 - y, -z; (iv) 1 - x, 1 - y, 1 - z.
 

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