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The title compound, C31H31N3O, was obtained by the reaction of 4-dibenzyl­amino-3-oxo-5-phenyl­penta­nenitrile with 2-methyl­pyridinylmagnesium chloride. The crystal structure involves inter­molecular N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806003795/rz6168sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806003795/rz6168Isup2.hkl
Contains datablock I

CCDC reference: 601235

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.064
  • wR factor = 0.178
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C27 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C1 -C6 1.36 Ang. PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C9 -C14 1.37 Ang. PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C17 -C22 1.36 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); 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) and ViewerPro (Accelrys, 2001); software used to prepare material for publication: SHELXL97.

(Z)-2-Amino-5-dibenzylamino-6-phenyl-1-(2-pyridyl)hex-2-en-3-one top
Crystal data top
C31H31N3OZ = 2
Mr = 461.59F(000) = 492
Triclinic, P1Dx = 1.229 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.003 (3) ÅCell parameters from 2165 reflections
b = 10.892 (4) Åθ = 2.4–25.6°
c = 13.802 (5) ŵ = 0.08 mm1
α = 76.427 (6)°T = 273 K
β = 71.484 (6)°Block, yellow
γ = 84.656 (7)°0.56 × 0.34 × 0.21 mm
V = 1247.2 (8) Å3
Data collection top
Bruker APEX area-detector
diffractometer
4319 independent reflections
Radiation source: fine-focus sealed tube3386 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1010
Tmin = 0.959, Tmax = 0.984k = 1212
6380 measured reflectionsl = 1516
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0812P)2 + 0.1595P]
where P = (Fo2 + 2Fc2)/3
4319 reflections(Δ/σ)max < 0.001
316 parametersΔρmax = 0.19 e Å3
19 restraintsΔρmin = 0.19 e Å3
Special details top

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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.0706 (2)0.52032 (16)0.09477 (12)0.0670 (5)
C150.1609 (2)0.59698 (19)0.21393 (15)0.0444 (5)
H15A0.25460.56010.23220.053*
C230.1775 (3)0.57049 (19)0.10723 (16)0.0470 (5)
C90.3266 (2)0.72021 (18)0.32215 (16)0.0437 (5)
C250.3456 (3)0.60131 (19)0.07408 (17)0.0505 (6)
C140.4661 (3)0.7042 (2)0.24900 (17)0.0516 (6)
H14A0.47090.71880.17890.062*
C160.0216 (3)0.5303 (2)0.29939 (17)0.0528 (6)
H16A0.01240.57560.35560.063*
H16B0.06440.53190.27100.063*
C240.3161 (3)0.6087 (2)0.02686 (16)0.0515 (5)
H24A0.39370.64150.04420.062*
C170.0601 (3)0.3968 (2)0.34238 (16)0.0498 (5)
C80.1823 (3)0.7699 (2)0.29289 (17)0.0523 (6)
H8A0.09120.74060.35200.063*
H8B0.18110.86140.27970.063*
C100.3230 (3)0.6955 (2)0.42514 (18)0.0565 (6)
H10A0.22890.70380.47660.068*
C270.4636 (3)0.7703 (2)0.22811 (17)0.0539 (6)
C70.0466 (3)0.8063 (2)0.16528 (19)0.0543 (6)
H7A0.04880.80390.22360.065*
H7B0.02530.76880.11400.065*
C60.0924 (2)0.9405 (2)0.11711 (17)0.0525 (6)
C260.4931 (3)0.6522 (3)0.15612 (18)0.0669 (7)
H26A0.56620.66910.12240.080*
H26B0.54090.58900.19640.080*
C130.5996 (3)0.6670 (2)0.2771 (2)0.0632 (7)
H13A0.69400.65770.22610.076*
C110.4562 (4)0.6586 (2)0.4530 (2)0.0690 (7)
H11A0.45230.64360.52290.083*
C280.5033 (4)0.8864 (3)0.2235 (2)0.0822 (9)
H28A0.55120.89470.17490.099*
C120.5939 (3)0.6438 (3)0.3786 (2)0.0716 (7)
H12A0.68400.61780.39770.086*
C180.1452 (3)0.3697 (2)0.41209 (18)0.0632 (7)
H18A0.17740.43550.43260.076*
C220.0161 (3)0.2981 (3)0.3145 (2)0.0685 (7)
H22A0.04060.31350.26700.082*
C310.3648 (4)0.8605 (3)0.3601 (2)0.0797 (8)
H31A0.31570.85120.40790.096*
C50.0107 (4)1.0382 (2)0.1347 (2)0.0770 (8)
H5A0.11251.02140.17840.092*
C190.1829 (4)0.2491 (3)0.4514 (2)0.0761 (8)
H19A0.24130.23340.49800.091*
C200.1373 (4)0.1517 (3)0.4240 (2)0.0786 (8)
H20A0.16260.06910.45190.094*
C10.2398 (3)0.9687 (2)0.0506 (2)0.0803 (8)
H1A0.31210.90350.03630.096*
C300.4009 (4)0.9762 (3)0.3611 (3)0.0900 (10)
H30A0.37801.04550.40840.108*
C210.0533 (4)0.1758 (3)0.3547 (2)0.0824 (9)
H21A0.02120.10940.33480.099*
C290.4705 (4)0.9910 (3)0.2929 (3)0.0958 (11)
H29A0.49691.07120.29200.115*
C30.1789 (5)1.1864 (3)0.0249 (3)0.0985 (11)
H3A0.20871.26960.00560.118*
C40.0320 (5)1.1605 (3)0.0893 (3)0.0996 (11)
H4A0.04011.22610.10290.120*
C20.2824 (4)1.0903 (3)0.0051 (3)0.1005 (11)
H2A0.38331.10750.03980.121*
N10.1686 (2)0.73285 (15)0.20208 (13)0.0447 (4)
N30.2474 (3)0.55393 (18)0.10781 (15)0.0649 (6)
H3B0.15910.52550.06490.078*
H3C0.27150.55130.17280.078*
N20.3943 (3)0.75754 (18)0.29557 (15)0.0634 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0780 (12)0.0731 (11)0.0525 (9)0.0330 (10)0.0177 (8)0.0098 (8)
C150.0395 (12)0.0474 (12)0.0437 (11)0.0029 (9)0.0098 (9)0.0083 (9)
C230.0517 (13)0.0428 (11)0.0460 (12)0.0020 (10)0.0145 (10)0.0089 (9)
C90.0462 (12)0.0400 (11)0.0457 (11)0.0070 (9)0.0118 (9)0.0117 (9)
C250.0566 (14)0.0418 (11)0.0473 (12)0.0104 (10)0.0125 (11)0.0079 (9)
C140.0516 (14)0.0589 (13)0.0470 (12)0.0067 (11)0.0136 (10)0.0164 (10)
C160.0433 (13)0.0623 (14)0.0475 (12)0.0031 (10)0.0061 (10)0.0117 (10)
C240.0484 (13)0.0581 (13)0.0461 (12)0.0005 (10)0.0128 (10)0.0102 (10)
C170.0443 (12)0.0590 (13)0.0374 (11)0.0118 (10)0.0012 (9)0.0052 (10)
C80.0486 (13)0.0572 (13)0.0519 (13)0.0016 (10)0.0121 (10)0.0185 (10)
C100.0625 (15)0.0598 (14)0.0458 (12)0.0076 (12)0.0124 (11)0.0122 (10)
C270.0494 (14)0.0619 (14)0.0422 (12)0.0055 (11)0.0012 (10)0.0149 (10)
C70.0427 (13)0.0596 (14)0.0613 (14)0.0035 (11)0.0181 (11)0.0133 (11)
C60.0568 (14)0.0532 (13)0.0537 (13)0.0100 (11)0.0266 (11)0.0143 (10)
C260.0566 (15)0.0835 (17)0.0477 (13)0.0139 (13)0.0063 (11)0.0086 (12)
C130.0483 (14)0.0719 (16)0.0766 (17)0.0010 (12)0.0194 (12)0.0296 (13)
C110.087 (2)0.0709 (16)0.0561 (15)0.0021 (15)0.0345 (15)0.0122 (12)
C280.083 (2)0.094 (2)0.0697 (17)0.0281 (17)0.0064 (15)0.0322 (16)
C120.0696 (18)0.0759 (17)0.085 (2)0.0133 (14)0.0411 (16)0.0285 (15)
C180.0674 (16)0.0690 (16)0.0530 (14)0.0143 (13)0.0192 (12)0.0064 (12)
C220.0756 (18)0.0680 (16)0.0655 (15)0.0158 (14)0.0292 (14)0.0051 (13)
C310.095 (2)0.078 (2)0.0594 (16)0.0004 (16)0.0231 (15)0.0035 (14)
C50.088 (2)0.0756 (18)0.0656 (16)0.0309 (15)0.0254 (15)0.0228 (14)
C190.0790 (19)0.0802 (19)0.0657 (17)0.0097 (16)0.0280 (15)0.0022 (14)
C200.081 (2)0.0641 (17)0.0729 (18)0.0003 (15)0.0140 (15)0.0065 (14)
C10.0677 (18)0.0584 (16)0.096 (2)0.0054 (13)0.0142 (16)0.0009 (14)
C300.100 (3)0.067 (2)0.076 (2)0.0014 (17)0.0024 (18)0.0023 (15)
C210.099 (2)0.0604 (17)0.088 (2)0.0148 (16)0.0272 (18)0.0151 (15)
C290.109 (3)0.0549 (17)0.103 (3)0.0278 (17)0.003 (2)0.0165 (17)
C30.162 (4)0.0564 (17)0.091 (2)0.006 (2)0.067 (2)0.0018 (16)
C40.159 (3)0.0649 (19)0.085 (2)0.047 (2)0.056 (2)0.0288 (17)
C20.103 (2)0.067 (2)0.113 (3)0.0160 (18)0.029 (2)0.0178 (17)
N10.0423 (10)0.0462 (10)0.0465 (10)0.0013 (8)0.0152 (8)0.0107 (8)
N30.0899 (16)0.0575 (12)0.0466 (11)0.0094 (11)0.0143 (11)0.0163 (9)
N20.0796 (15)0.0560 (12)0.0527 (11)0.0049 (10)0.0190 (11)0.0086 (9)
Geometric parameters (Å, º) top
O1—C231.225 (3)C26—H26B0.9700
C15—N11.456 (3)C13—C121.349 (4)
C15—C161.523 (3)C13—H13A0.9300
C15—C231.525 (3)C11—C121.360 (4)
C15—H15A0.9800C11—H11A0.9300
C23—C241.401 (3)C28—C291.382 (5)
C9—C141.365 (3)C28—H28A0.9300
C9—C101.373 (3)C12—H12A0.9300
C9—C81.498 (3)C18—C191.355 (4)
C25—N31.313 (3)C18—H18A0.9300
C25—C241.353 (3)C22—C211.372 (4)
C25—C261.497 (3)C22—H22A0.9300
C14—C131.376 (3)C31—N21.322 (3)
C14—H14A0.9300C31—C301.327 (4)
C16—C171.489 (3)C31—H31A0.9300
C16—H16A0.9700C5—C41.366 (3)
C16—H16B0.9700C5—H5A0.9300
C24—H24A0.9300C19—C201.343 (4)
C17—C221.353 (3)C19—H19A0.9300
C17—C181.376 (3)C20—C211.364 (4)
C8—N11.446 (3)C20—H20A0.9300
C8—H8A0.9700C1—C21.359 (3)
C8—H8B0.9700C1—H1A0.9300
C10—C111.370 (4)C30—C291.329 (5)
C10—H10A0.9300C30—H30A0.9300
C27—N21.312 (3)C21—H21A0.9300
C27—C281.366 (4)C29—H29A0.9300
C27—C261.489 (3)C3—C41.351 (4)
C7—N11.451 (3)C3—C21.352 (4)
C7—C61.493 (3)C3—H3A0.9300
C7—H7A0.9700C4—H4A0.9300
C7—H7B0.9700C2—H2A0.9300
C6—C51.359 (3)N3—H3B0.8600
C6—C11.366 (3)N3—H3C0.8600
C26—H26A0.9700
N1—C15—C16116.91 (18)C12—C13—H13A120.0
N1—C15—C23108.31 (16)C14—C13—H13A120.0
C16—C15—C23112.17 (17)C12—C11—C10120.1 (2)
N1—C15—H15A106.3C12—C11—H11A119.9
C16—C15—H15A106.3C10—C11—H11A119.9
C23—C15—H15A106.3C27—C28—C29118.3 (3)
O1—C23—C24123.3 (2)C27—C28—H28A120.8
O1—C23—C15119.79 (19)C29—C28—H28A120.8
C24—C23—C15116.90 (19)C13—C12—C11119.9 (2)
C14—C9—C10117.9 (2)C13—C12—H12A120.1
C14—C9—C8122.21 (19)C11—C12—H12A120.1
C10—C9—C8119.8 (2)C19—C18—C17121.3 (2)
N3—C25—C24123.4 (2)C19—C18—H18A119.3
N3—C25—C26115.4 (2)C17—C18—H18A119.3
C24—C25—C26121.1 (2)C17—C22—C21121.6 (3)
C9—C14—C13121.2 (2)C17—C22—H22A119.2
C9—C14—H14A119.4C21—C22—H22A119.2
C13—C14—H14A119.4N2—C31—C30124.1 (3)
C17—C16—C15112.24 (18)N2—C31—H31A118.0
C17—C16—H16A109.2C30—C31—H31A118.0
C15—C16—H16A109.2C6—C5—C4121.4 (3)
C17—C16—H16B109.2C6—C5—H5A119.3
C15—C16—H16B109.2C4—C5—H5A119.3
H16A—C16—H16B107.9C20—C19—C18120.9 (3)
C25—C24—C23124.9 (2)C20—C19—H19A119.5
C25—C24—H24A117.6C18—C19—H19A119.5
C23—C24—H24A117.6C19—C20—C21119.0 (3)
C22—C17—C18117.2 (2)C19—C20—H20A120.5
C22—C17—C16122.5 (2)C21—C20—H20A120.5
C18—C17—C16120.3 (2)C2—C1—C6121.1 (3)
N1—C8—C9114.62 (18)C2—C1—H1A119.4
N1—C8—H8A108.6C6—C1—H1A119.4
C9—C8—H8A108.6C31—C30—C29118.7 (3)
N1—C8—H8B108.6C31—C30—H30A120.7
C9—C8—H8B108.6C29—C30—H30A120.7
H8A—C8—H8B107.6C20—C21—C22119.9 (3)
C11—C10—C9120.9 (2)C20—C21—H21A120.0
C11—C10—H10A119.6C22—C21—H21A120.0
C9—C10—H10A119.6C30—C29—C28119.5 (3)
N2—C27—C28121.4 (2)C30—C29—H29A120.3
N2—C27—C26116.4 (2)C28—C29—H29A120.3
C28—C27—C26122.3 (3)C4—C3—C2119.4 (3)
N1—C7—C6111.69 (17)C4—C3—H3A120.3
N1—C7—H7A109.3C2—C3—H3A120.3
C6—C7—H7A109.3C3—C4—C5120.0 (3)
N1—C7—H7B109.3C3—C4—H4A120.0
C6—C7—H7B109.3C5—C4—H4A120.0
H7A—C7—H7B107.9C3—C2—C1120.4 (3)
C5—C6—C1117.6 (2)C3—C2—H2A119.8
C5—C6—C7121.8 (2)C1—C2—H2A119.8
C1—C6—C7120.5 (2)C8—N1—C7110.99 (17)
C27—C26—C25112.0 (2)C8—N1—C15114.11 (16)
C27—C26—H26A109.2C7—N1—C15114.71 (16)
C25—C26—H26A109.2C25—N3—H3B120.0
C27—C26—H26B109.2C25—N3—H3C120.0
C25—C26—H26B109.2H3B—N3—H3C120.0
H26A—C26—H26B107.9C27—N2—C31118.1 (2)
C12—C13—C14120.1 (2)
N1—C15—C23—O1118.3 (2)C22—C17—C18—C190.2 (4)
C16—C15—C23—O112.2 (3)C16—C17—C18—C19179.3 (2)
N1—C15—C23—C2460.2 (2)C18—C17—C22—C210.6 (4)
C16—C15—C23—C24169.25 (19)C16—C17—C22—C21179.7 (2)
C10—C9—C14—C131.3 (3)C1—C6—C5—C41.4 (4)
C8—C9—C14—C13175.4 (2)C7—C6—C5—C4179.3 (2)
N1—C15—C16—C17150.55 (18)C17—C18—C19—C200.5 (4)
C23—C15—C16—C1783.5 (2)C18—C19—C20—C210.7 (5)
N3—C25—C24—C231.8 (4)C5—C6—C1—C21.1 (4)
C26—C25—C24—C23176.0 (2)C7—C6—C1—C2179.1 (3)
O1—C23—C24—C253.7 (4)N2—C31—C30—C290.3 (5)
C15—C23—C24—C25174.84 (19)C19—C20—C21—C220.3 (5)
C15—C16—C17—C22101.8 (3)C17—C22—C21—C200.4 (5)
C15—C16—C17—C1877.2 (3)C31—C30—C29—C280.1 (5)
C14—C9—C8—N133.9 (3)C27—C28—C29—C300.5 (5)
C10—C9—C8—N1149.52 (19)C2—C3—C4—C50.5 (5)
C14—C9—C10—C111.4 (3)C6—C5—C4—C30.6 (5)
C8—C9—C10—C11175.3 (2)C4—C3—C2—C10.8 (5)
N1—C7—C6—C5138.7 (2)C6—C1—C2—C30.1 (5)
N1—C7—C6—C143.4 (3)C9—C8—N1—C7167.25 (17)
N2—C27—C26—C2572.9 (3)C9—C8—N1—C1561.3 (2)
C28—C27—C26—C25105.9 (3)C6—C7—N1—C870.4 (2)
N3—C25—C26—C2770.2 (3)C6—C7—N1—C15158.48 (17)
C24—C25—C26—C27107.7 (3)C16—C15—N1—C862.5 (2)
C9—C14—C13—C120.9 (4)C23—C15—N1—C8169.63 (17)
C9—C10—C11—C121.2 (4)C16—C15—N1—C767.1 (2)
N2—C27—C28—C290.8 (4)C23—C15—N1—C760.7 (2)
C26—C27—C28—C29179.6 (2)C28—C27—N2—C310.5 (4)
C14—C13—C12—C110.7 (4)C26—C27—N2—C31179.4 (2)
C10—C11—C12—C130.8 (4)C30—C31—N2—C270.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3B···O1i0.862.352.987 (3)131
Symmetry code: (i) x, y+1, z.
 

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