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The title compound, C23H18N4O, cyrstallizes as a discrete mol­ecular species with an intra­molecular N—H...O hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807015322/hg2205sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807015322/hg2205Isup2.hkl
Contains datablock I

CCDC reference: 647230

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.036
  • wR factor = 0.102
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1994); data reduction: XPREP (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.

2-{[Tris(2-pyridyl)methyl]iminomethyl}phenol top
Crystal data top
C23H18N4OZ = 2
Mr = 366.41F(000) = 384
Triclinic, P1Dx = 1.299 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.6327 (1) ÅCell parameters from 3689 reflections
b = 10.6779 (2) Åθ = 3.2–25.0°
c = 10.8432 (2) ŵ = 0.08 mm1
α = 79.001 (1)°T = 298 K
β = 85.057 (1)°Block, yellow
γ = 72.838 (1)°0.30 × 0.20 × 0.12 mm
V = 936.99 (3) Å3
Data collection top
Siemens SMART CCD
diffractometer
3689 independent reflections
Radiation source: fine-focus sealed tube3297 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
ω scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.976, Tmax = 0.990k = 1313
4356 measured reflectionsl = 1313
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)] = 0.036H-atom parameters constrained
wR(F2) = 0.102 w = 1/[σ2(Fo2) + (0.0497P)2 + 0.1663P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
3689 reflectionsΔρmax = 0.18 e Å3
254 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.008 (2)
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
N40.16118 (11)0.48557 (9)0.75075 (9)0.0405 (2)
O10.41251 (11)0.32215 (9)0.85989 (10)0.0603 (3)
H10.34800.39470.83570.090*
C10.06511 (12)0.62554 (10)0.71900 (10)0.0371 (2)
C170.12520 (13)0.39008 (11)0.71737 (11)0.0426 (3)
H170.03310.40710.67120.051*
N10.23009 (12)0.65230 (10)0.87802 (10)0.0477 (2)
C70.11490 (12)0.64070 (11)0.70218 (11)0.0398 (2)
C20.14055 (12)0.69071 (11)0.59912 (10)0.0385 (2)
C120.08314 (13)0.69234 (11)0.82960 (10)0.0387 (2)
C230.36610 (14)0.22613 (12)0.82220 (11)0.0448 (3)
C180.22744 (14)0.25432 (11)0.75113 (10)0.0421 (3)
N20.12008 (12)0.82094 (10)0.58818 (10)0.0505 (3)
N30.18043 (12)0.71043 (13)0.59524 (10)0.0562 (3)
C80.20224 (15)0.58391 (13)0.79838 (13)0.0529 (3)
H80.15210.53430.87180.063*
C190.18693 (18)0.14893 (13)0.71567 (12)0.0558 (3)
H190.09560.16690.66840.067*
C130.04381 (16)0.78825 (13)0.87394 (13)0.0538 (3)
H130.14380.81690.83610.065*
C90.36530 (15)0.60232 (14)0.78332 (15)0.0611 (4)
H90.42660.56490.84640.073*
C220.45926 (16)0.09454 (13)0.85453 (13)0.0571 (3)
H220.55180.07500.90090.069*
C100.43493 (15)0.67620 (16)0.67454 (15)0.0639 (4)
H100.54480.69140.66260.077*
C160.25066 (18)0.70673 (14)0.97492 (13)0.0578 (3)
H160.35310.68071.00870.069*
C140.01975 (19)0.84071 (15)0.97511 (14)0.0644 (4)
H140.10400.90391.00750.077*
C210.4159 (2)0.00659 (14)0.81870 (14)0.0649 (4)
H210.47930.09400.84140.078*
C150.1295 (2)0.79855 (15)1.02705 (13)0.0640 (4)
H150.14840.83131.09610.077*
C200.2795 (2)0.01934 (14)0.74935 (14)0.0663 (4)
H200.25060.04990.72580.080*
C30.22411 (17)0.61873 (15)0.50936 (13)0.0562 (3)
H30.23650.52790.51910.067*
C60.18349 (17)0.88185 (15)0.48493 (13)0.0603 (3)
H60.16920.97290.47610.072*
C110.33988 (16)0.72724 (18)0.58382 (15)0.0695 (4)
H110.38790.77660.50960.083*
C50.26793 (18)0.81692 (17)0.39224 (13)0.0666 (4)
H50.31000.86270.32210.080*
C40.2892 (2)0.68386 (19)0.40465 (14)0.0714 (4)
H40.34710.63710.34320.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N40.0352 (5)0.0425 (5)0.0454 (5)0.0116 (4)0.0049 (4)0.0090 (4)
O10.0519 (5)0.0540 (5)0.0772 (6)0.0172 (4)0.0260 (5)0.0031 (5)
C10.0311 (5)0.0413 (6)0.0401 (5)0.0111 (4)0.0028 (4)0.0087 (4)
C170.0391 (6)0.0488 (6)0.0429 (6)0.0136 (5)0.0075 (4)0.0106 (5)
N10.0450 (5)0.0562 (6)0.0473 (5)0.0197 (4)0.0076 (4)0.0111 (4)
C70.0316 (5)0.0442 (6)0.0466 (6)0.0113 (4)0.0013 (4)0.0138 (5)
C20.0286 (5)0.0488 (6)0.0399 (6)0.0122 (4)0.0042 (4)0.0091 (5)
C120.0394 (5)0.0431 (6)0.0372 (5)0.0182 (4)0.0006 (4)0.0063 (4)
C230.0432 (6)0.0481 (6)0.0421 (6)0.0150 (5)0.0005 (5)0.0030 (5)
C180.0457 (6)0.0450 (6)0.0371 (5)0.0147 (5)0.0009 (4)0.0087 (4)
N20.0484 (6)0.0494 (6)0.0504 (6)0.0129 (4)0.0030 (4)0.0045 (4)
N30.0355 (5)0.0838 (8)0.0478 (6)0.0145 (5)0.0060 (4)0.0095 (5)
C80.0399 (6)0.0546 (7)0.0625 (8)0.0163 (5)0.0001 (5)0.0023 (6)
C190.0704 (8)0.0528 (7)0.0496 (7)0.0213 (6)0.0060 (6)0.0143 (6)
C130.0484 (7)0.0567 (7)0.0597 (8)0.0142 (6)0.0016 (6)0.0209 (6)
C90.0401 (6)0.0612 (8)0.0848 (10)0.0209 (6)0.0115 (6)0.0152 (7)
C220.0514 (7)0.0548 (7)0.0551 (7)0.0090 (6)0.0021 (6)0.0054 (6)
C100.0300 (6)0.0838 (10)0.0837 (10)0.0149 (6)0.0015 (6)0.0306 (8)
C160.0660 (8)0.0675 (8)0.0499 (7)0.0324 (7)0.0150 (6)0.0076 (6)
C140.0733 (9)0.0672 (9)0.0619 (8)0.0265 (7)0.0155 (7)0.0310 (7)
C210.0786 (10)0.0436 (7)0.0612 (8)0.0072 (6)0.0069 (7)0.0020 (6)
C150.0917 (11)0.0734 (9)0.0430 (7)0.0428 (8)0.0030 (7)0.0204 (6)
C200.0974 (11)0.0470 (7)0.0583 (8)0.0234 (7)0.0035 (8)0.0165 (6)
C30.0596 (8)0.0626 (8)0.0541 (7)0.0237 (6)0.0082 (6)0.0228 (6)
C60.0591 (8)0.0585 (8)0.0590 (8)0.0203 (6)0.0005 (6)0.0046 (6)
C110.0368 (6)0.1090 (12)0.0602 (8)0.0138 (7)0.0106 (6)0.0156 (8)
C50.0611 (8)0.0920 (11)0.0476 (7)0.0331 (8)0.0078 (6)0.0008 (7)
C40.0729 (10)0.0955 (12)0.0529 (8)0.0313 (9)0.0189 (7)0.0281 (8)
Geometric parameters (Å, º) top
N4—C171.2706 (14)C13—C141.3794 (19)
N4—C11.4702 (14)C13—H130.9300
O1—C231.3451 (15)C9—C101.365 (2)
O1—H10.8200C9—H90.9300
C1—C71.5374 (14)C22—C211.371 (2)
C1—C21.5409 (15)C22—H220.9300
C1—C121.5477 (14)C10—C111.363 (2)
C17—C181.4535 (16)C10—H100.9300
C17—H170.9300C16—C151.371 (2)
N1—C121.3329 (14)C16—H160.9300
N1—C161.3415 (16)C14—C151.366 (2)
C7—N31.3244 (16)C14—H140.9300
C7—C81.3846 (16)C21—C201.382 (2)
C2—N21.3322 (15)C21—H210.9300
C2—C31.3767 (17)C15—H150.9300
C12—C131.3841 (17)C20—H200.9300
C23—C221.3921 (17)C3—C41.381 (2)
C23—C181.4054 (16)C3—H30.9300
C18—C191.3989 (16)C6—C51.365 (2)
N2—C61.3427 (17)C6—H60.9300
N3—C111.3481 (16)C11—H110.9300
C8—C91.3823 (18)C5—C41.359 (2)
C8—H80.9300C5—H50.9300
C19—C201.375 (2)C4—H40.9300
C19—H190.9300
C17—N4—C1123.47 (9)C10—C9—H9120.5
C23—O1—H1109.5C8—C9—H9120.5
N4—C1—C7112.50 (8)C21—C22—C23120.63 (13)
N4—C1—C2108.57 (8)C21—C22—H22119.7
C7—C1—C2111.05 (8)C23—C22—H22119.7
N4—C1—C12105.89 (8)C11—C10—C9118.52 (12)
C7—C1—C12110.05 (8)C11—C10—H10120.7
C2—C1—C12108.58 (8)C9—C10—H10120.7
N4—C17—C18120.25 (10)N1—C16—C15123.80 (13)
N4—C17—H17119.9N1—C16—H16118.1
C18—C17—H17119.9C15—C16—H16118.1
C12—N1—C16117.26 (11)C15—C14—C13119.11 (13)
N3—C7—C8122.76 (10)C15—C14—H14120.4
N3—C7—C1117.65 (10)C13—C14—H14120.4
C8—C7—C1119.58 (10)C22—C21—C20121.02 (13)
N2—C2—C3122.23 (11)C22—C21—H21119.5
N2—C2—C1115.70 (9)C20—C21—H21119.5
C3—C2—C1122.07 (11)C14—C15—C16118.39 (12)
N1—C12—C13122.37 (11)C14—C15—H15120.8
N1—C12—C1115.29 (9)C16—C15—H15120.8
C13—C12—C1122.33 (10)C19—C20—C21119.06 (13)
O1—C23—C22118.67 (11)C19—C20—H20120.5
O1—C23—C18122.24 (11)C21—C20—H20120.5
C22—C23—C18119.08 (12)C2—C3—C4118.80 (13)
C19—C18—C23118.86 (11)C2—C3—H3120.6
C19—C18—C17120.30 (11)C4—C3—H3120.6
C23—C18—C17120.82 (10)N2—C6—C5123.32 (14)
C2—N2—C6117.68 (11)N2—C6—H6118.3
C7—N3—C11116.97 (12)C5—C6—H6118.3
C9—C8—C7118.80 (13)N3—C11—C10123.96 (14)
C9—C8—H8120.6N3—C11—H11118.0
C7—C8—H8120.6C10—C11—H11118.0
C20—C19—C18121.34 (13)C4—C5—C6118.58 (13)
C20—C19—H19119.3C4—C5—H5120.7
C18—C19—H19119.3C6—C5—H5120.7
C14—C13—C12119.00 (13)C5—C4—C3119.38 (13)
C14—C13—H13120.5C5—C4—H4120.3
C12—C13—H13120.5C3—C4—H4120.3
C10—C9—C8118.98 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N40.821.842.5638 (12)147
 

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