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In the title compound, C21H16FN3O2, the pyridine ring is nearly coplanar with the plane of the fused bicyclic ring system [dihedral angle = 4.1 (2)°], while the 4-fluoro­phenyl ring forms a dihedral angle of 67.7 (3)° with the fused bicyclic ring system.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806012153/tk2018sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806012153/tk2018Isup2.hkl
Contains datablock I

CCDC reference: 608506

Key indicators

  • Single-crystal X-ray study
  • T = 208 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.051
  • wR factor = 0.128
  • Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.76
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 1 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, 2005); cell refinement: SMART; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SIR2004 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2'-[2-(4-Fluorophenyl)chroman-4-ylidene]isonicotinohydrazide top
Crystal data top
C21H16FN3O2F(000) = 752
Mr = 361.37Dx = 1.449 Mg m3
Monoclinic, P21/cMelting point: 210 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 11.654 (5) ÅCell parameters from 4435 reflections
b = 5.471 (2) Åθ = 2.6–28.1°
c = 26.609 (10) ŵ = 0.10 mm1
β = 102.416 (6)°T = 208 K
V = 1656.9 (11) Å3Plate, yellow
Z = 40.20 × 0.20 × 0.07 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2933 independent reflections
Radiation source: fine-focus sealed tube2219 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.065
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1213
Tmin = 0.980, Tmax = 0.993k = 66
9130 measured reflectionsl = 3131
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0622P)2 + 0.1714P]
where P = (Fo2 + 2Fc2)/3
2933 reflections(Δ/σ)max < 0.001
244 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = 0.17 e Å3
Special details top

Experimental. 1H NMR (300 MHz, DMSO-d6): δ 11.11 (s, 1H), 8.75 (d, 2H, J = 6.0 Hz), 8.06 (d, 1H, J = 7.2 Hz), 7.78 (d, 2H, J = 5.4 Hz), 7.65–7.60 (m, 2H), 7.42–7.26 (m, 3H), 7.11–7.011 (m, 2H), 5.30 (dd, 1H, J1 = 12.3 Hz, J2 = 2.1 Hz), 3.48 (d, 1H, J = 14.4 Hz), 2.90 (dd, 1H, J1 = 12.6 Hz, J2 = 16.9 Hz).

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
C10.77866 (19)0.1949 (4)0.63397 (8)0.0389 (6)
H10.82550.07850.65490.047*
C20.7290 (2)0.3815 (5)0.65632 (8)0.0434 (6)
H2A0.74290.39340.69240.052*
C30.6588 (2)0.5522 (4)0.62611 (9)0.0402 (6)
H30.62590.68140.64160.048*
C40.6369 (2)0.5333 (4)0.57371 (8)0.0380 (5)
H40.58780.64760.55320.046*
C50.68711 (18)0.3464 (4)0.55093 (8)0.0309 (5)
C60.76051 (17)0.1752 (4)0.58037 (8)0.0292 (5)
C70.81877 (17)0.0115 (4)0.55473 (7)0.0277 (5)
C80.78476 (19)0.0158 (4)0.49727 (8)0.0354 (5)
H8A0.78120.18560.48530.042*
H8B0.84500.06870.48320.042*
C90.6682 (2)0.1041 (4)0.47746 (8)0.0395 (6)
H90.60790.00280.48870.047*
C100.63637 (18)0.1154 (4)0.41965 (8)0.0330 (5)
C110.5699 (2)0.0704 (4)0.39371 (8)0.0400 (6)
H110.54150.19370.41240.048*
C120.5440 (2)0.0796 (4)0.34067 (8)0.0416 (6)
H120.49930.20860.32310.050*
C130.5847 (2)0.1025 (4)0.31437 (8)0.0376 (5)
C140.6491 (2)0.2930 (4)0.33846 (9)0.0432 (6)
H140.67500.41830.31940.052*
C150.6755 (2)0.2975 (4)0.39174 (9)0.0412 (6)
H150.72070.42650.40910.049*
C161.01894 (18)0.5016 (4)0.58088 (8)0.0302 (5)
C171.05581 (18)0.5295 (4)0.63831 (7)0.0301 (5)
C181.0366 (2)0.3662 (4)0.67530 (8)0.0374 (5)
H180.99110.22490.66590.045*
C191.0854 (2)0.4148 (4)0.72638 (8)0.0409 (6)
H191.07250.30050.75100.049*
C201.1649 (2)0.7678 (4)0.70708 (8)0.0416 (6)
H201.20890.90980.71770.050*
C211.1210 (2)0.7356 (4)0.65516 (8)0.0369 (5)
H211.13530.85300.63140.044*
N10.89357 (15)0.1535 (3)0.58301 (6)0.0293 (4)
N20.94797 (15)0.3216 (3)0.55757 (6)0.0308 (4)
H20.93580.31120.52420.037*
N31.14906 (16)0.6104 (4)0.74327 (7)0.0404 (5)
O10.66208 (14)0.3399 (3)0.49802 (5)0.0404 (4)
O21.05759 (14)0.6471 (3)0.55330 (5)0.0418 (4)
F10.56160 (14)0.0931 (3)0.26227 (5)0.0606 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0358 (13)0.0485 (15)0.0301 (12)0.0097 (11)0.0023 (10)0.0062 (10)
C20.0412 (14)0.0587 (16)0.0296 (12)0.0040 (12)0.0062 (10)0.0143 (11)
C30.0391 (13)0.0382 (13)0.0460 (14)0.0014 (11)0.0147 (11)0.0117 (11)
C40.0379 (13)0.0338 (12)0.0437 (13)0.0054 (10)0.0118 (11)0.0010 (10)
C50.0329 (12)0.0313 (12)0.0295 (11)0.0012 (10)0.0092 (9)0.0023 (9)
C60.0238 (11)0.0315 (12)0.0320 (11)0.0009 (9)0.0055 (9)0.0038 (9)
C70.0239 (11)0.0299 (12)0.0290 (11)0.0002 (9)0.0054 (9)0.0011 (9)
C80.0346 (13)0.0405 (13)0.0306 (11)0.0091 (10)0.0061 (10)0.0028 (10)
C90.0421 (13)0.0397 (14)0.0346 (12)0.0059 (11)0.0037 (10)0.0017 (10)
C100.0320 (12)0.0363 (13)0.0299 (11)0.0131 (10)0.0051 (9)0.0024 (9)
C110.0500 (15)0.0343 (13)0.0362 (13)0.0007 (11)0.0107 (11)0.0032 (10)
C120.0474 (14)0.0403 (14)0.0340 (12)0.0047 (11)0.0015 (10)0.0039 (10)
C130.0434 (13)0.0426 (14)0.0249 (11)0.0062 (11)0.0033 (10)0.0013 (10)
C140.0493 (15)0.0403 (14)0.0413 (14)0.0014 (12)0.0127 (11)0.0104 (11)
C150.0382 (13)0.0391 (14)0.0434 (14)0.0012 (11)0.0021 (11)0.0068 (10)
C160.0283 (11)0.0332 (12)0.0284 (11)0.0019 (9)0.0043 (9)0.0003 (9)
C170.0290 (11)0.0319 (12)0.0292 (11)0.0023 (9)0.0056 (9)0.0023 (9)
C180.0384 (13)0.0413 (13)0.0308 (12)0.0075 (11)0.0033 (10)0.0009 (10)
C190.0441 (14)0.0476 (15)0.0303 (12)0.0038 (12)0.0063 (10)0.0033 (10)
C200.0499 (14)0.0392 (13)0.0352 (13)0.0084 (12)0.0079 (11)0.0100 (10)
C210.0443 (13)0.0332 (12)0.0339 (13)0.0029 (11)0.0095 (10)0.0022 (10)
N10.0286 (9)0.0317 (10)0.0278 (9)0.0030 (8)0.0061 (7)0.0038 (7)
N20.0328 (10)0.0378 (11)0.0214 (9)0.0081 (8)0.0045 (7)0.0010 (7)
N30.0414 (11)0.0487 (12)0.0304 (10)0.0033 (10)0.0060 (9)0.0065 (9)
O10.0535 (10)0.0362 (9)0.0306 (8)0.0151 (8)0.0073 (7)0.0002 (7)
O20.0517 (10)0.0443 (10)0.0294 (8)0.0196 (8)0.0086 (7)0.0011 (7)
F10.0868 (12)0.0648 (10)0.0265 (7)0.0040 (9)0.0042 (7)0.0044 (6)
Geometric parameters (Å, º) top
C1—C21.371 (3)C11—H110.9400
C1—C61.400 (3)C12—C131.360 (3)
C1—H10.9400C12—H120.9400
C2—C31.380 (3)C13—F11.355 (2)
C2—H2A0.9400C13—C141.361 (3)
C3—C41.366 (3)C14—C151.385 (3)
C3—H30.9400C14—H140.9400
C4—C51.381 (3)C15—H150.9400
C4—H40.9400C16—O21.232 (2)
C5—O11.375 (2)C16—N21.348 (3)
C5—C61.391 (3)C16—C171.504 (3)
C6—C71.473 (3)C17—C211.380 (3)
C7—N11.283 (3)C17—C181.383 (3)
C7—C81.495 (3)C18—C191.382 (3)
C8—C91.499 (3)C18—H180.9400
C8—H8A0.9800C19—N31.324 (3)
C8—H8B0.9800C19—H190.9400
C9—O11.409 (3)C20—N31.334 (3)
C9—C101.504 (3)C20—C211.377 (3)
C9—H90.9900C20—H200.9400
C10—C111.371 (3)C21—H210.9400
C10—C151.377 (3)N1—N21.375 (2)
C11—C121.379 (3)N2—H20.8700
C2—C1—C6120.9 (2)C12—C11—H11119.4
C2—C1—H1119.5C13—C12—C11118.4 (2)
C6—C1—H1119.5C13—C12—H12120.8
C1—C2—C3120.3 (2)C11—C12—H12120.8
C1—C2—H2A119.9F1—C13—C12119.0 (2)
C3—C2—H2A119.9F1—C13—C14118.6 (2)
C4—C3—C2120.0 (2)C12—C13—C14122.4 (2)
C4—C3—H3120.0C13—C14—C15118.3 (2)
C2—C3—H3120.0C13—C14—H14120.8
C3—C4—C5120.0 (2)C15—C14—H14120.8
C3—C4—H4120.0C10—C15—C14120.8 (2)
C5—C4—H4120.0C10—C15—H15119.6
O1—C5—C4116.85 (19)C14—C15—H15119.6
O1—C5—C6121.91 (17)O2—C16—N2117.69 (18)
C4—C5—C6121.23 (19)O2—C16—C17118.60 (19)
C5—C6—C1117.50 (18)N2—C16—C17123.69 (18)
C5—C6—C7119.67 (18)C21—C17—C18117.3 (2)
C1—C6—C7122.80 (19)C21—C17—C16115.50 (18)
N1—C7—C6118.07 (17)C18—C17—C16127.1 (2)
N1—C7—C8125.99 (18)C19—C18—C17118.7 (2)
C6—C7—C8115.94 (17)C19—C18—H18120.6
C7—C8—C9111.95 (17)C17—C18—H18120.6
C7—C8—H8A109.2N3—C19—C18124.8 (2)
C9—C8—H8A109.2N3—C19—H19117.6
C7—C8—H8B109.2C18—C19—H19117.6
C9—C8—H8B109.2N3—C20—C21124.2 (2)
H8A—C8—H8B107.9N3—C20—H20117.9
O1—C9—C8112.45 (19)C21—C20—H20117.9
O1—C9—C10109.73 (18)C20—C21—C17119.4 (2)
C8—C9—C10112.54 (17)C20—C21—H21120.3
O1—C9—H9107.3C17—C21—H21120.3
C8—C9—H9107.3C7—N1—N2116.29 (16)
C10—C9—H9107.3C16—N2—N1124.35 (17)
C11—C10—C15118.8 (2)C16—N2—H2117.8
C11—C10—C9118.2 (2)N1—N2—H2117.8
C15—C10—C9122.9 (2)C19—N3—C20115.53 (19)
C10—C11—C12121.2 (2)C5—O1—C9113.81 (16)
C10—C11—H11119.4
 

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