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In the title compound, C26H18F2N2O4, the dihedral angle between the amide groups is 57.1 (3)°. The crystal structure is stabilized by N—H...O hydrogen bonds and C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806024342/ob2033sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806024342/ob2033Isup2.hkl
Contains datablock I

CCDC reference: 613793

Key indicators

  • Single-crystal X-ray study
  • T = 290 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.098
  • wR factor = 0.197
  • Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 5.16 Ratio
Author Response: The carbon atoms of the phenyl ring C15-C20 and C21-C26 have large thermal parameters compared to the riding hydrogens and hence the ratio Ueq(max)/Ueq(min) has a large value.
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.97 Ratio
Author Response: The carbon atoms of the phenyl ring C15-C20 and C21-C26 have large thermal parameters compared to the riding hydrogens and hence the ratio Ueq(max)/Ueq(min) has a large value.

Alert level B PLAT331_ALERT_2_B Small Average Phenyl C-C Dist. C15 -C20 1.36 Ang.
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C19 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C23 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C21 -C26 1.37 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C26 H18 F2 N2 O4
2 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).

4-fluoro-N'-(4-fluoro-3-phenoxybenzoyl)-3-phenoxybenzohydrazide top
Crystal data top
C26H18F2N2O4F(000) = 952
Mr = 460.42Dx = 1.387 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 963 reflections
a = 18.375 (4) Åθ = 1.4–25.2°
b = 18.236 (4) ŵ = 0.11 mm1
c = 6.5954 (15) ÅT = 290 K
β = 93.680 (5)°Plate, colourless
V = 2205.5 (8) Å30.25 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3865 independent reflections
Radiation source: fine-focus sealed tube2556 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.082
φ and ω scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2021
Tmin = 0.940, Tmax = 0.990k = 2021
15717 measured reflectionsl = 77
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)] = 0.098Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.197H atoms treated by a mixture of independent and constrained refinement
S = 1.29 w = 1/[σ2(Fo2) + (0.0504P)2 + 0.9271P]
where P = (Fo2 + 2Fc2)/3
3865 reflections(Δ/σ)max < 0.001
315 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.21 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
F10.27051 (16)0.30472 (17)0.7141 (4)0.0692 (10)
F20.72283 (18)0.46088 (18)0.8405 (4)0.0761 (10)
O10.2084 (2)0.3548 (2)0.3743 (6)0.0697 (12)
O20.43013 (17)0.44754 (17)0.0003 (4)0.0424 (9)
O30.56499 (17)0.27593 (17)0.1942 (4)0.0401 (8)
O40.7534 (2)0.3212 (2)0.7226 (5)0.0637 (11)
N10.5601 (2)0.3867 (2)0.0488 (5)0.0360 (10)
N20.5135 (2)0.3622 (2)0.0940 (6)0.0369 (10)
C10.7055 (3)0.3637 (3)0.6167 (7)0.0432 (13)
C20.6890 (3)0.4342 (3)0.6804 (7)0.0457 (14)
C30.6388 (3)0.4754 (3)0.5902 (7)0.0472 (14)
C40.6049 (3)0.4465 (2)0.4287 (6)0.0371 (12)
C50.6200 (2)0.3761 (2)0.3603 (6)0.0304 (11)
C60.6713 (2)0.3347 (3)0.4562 (7)0.0404 (12)
C70.5795 (2)0.3415 (3)0.1955 (6)0.0299 (11)
C80.4492 (3)0.3956 (2)0.1101 (6)0.0313 (11)
C90.4037 (2)0.3674 (2)0.2732 (6)0.0281 (11)
C100.4333 (3)0.3369 (2)0.4510 (6)0.0354 (12)
C110.3885 (3)0.3161 (2)0.6011 (7)0.0415 (13)
C120.3148 (3)0.3239 (2)0.5684 (7)0.0418 (13)
C130.2825 (3)0.3529 (3)0.3885 (7)0.0427 (13)
C140.3282 (3)0.3754 (2)0.2424 (7)0.0392 (12)
C150.1736 (3)0.3840 (4)0.1989 (10)0.0590 (16)
C160.1542 (4)0.3392 (4)0.0415 (11)0.084 (2)
C170.1171 (5)0.3679 (6)0.1287 (13)0.116 (3)
C180.0992 (5)0.4403 (8)0.1355 (17)0.131 (4)
C190.1202 (5)0.4839 (6)0.022 (2)0.145 (5)
C200.1574 (4)0.4559 (4)0.1923 (14)0.102 (3)
C210.8270 (3)0.3381 (3)0.6990 (10)0.0621 (17)
C220.8677 (4)0.3151 (4)0.8540 (12)0.096 (2)
C230.9418 (6)0.3257 (5)0.8361 (19)0.133 (4)
C240.9737 (5)0.3598 (6)0.674 (2)0.139 (4)
C250.9332 (4)0.3829 (5)0.5196 (15)0.119 (3)
C260.8581 (4)0.3716 (4)0.5321 (11)0.082 (2)
H1N0.565 (2)0.434 (3)0.053 (7)0.049 (16)*
H2N0.528 (2)0.325 (2)0.156 (6)0.029 (14)*
H30.62760.52240.63700.057*
H40.57110.47480.36420.045*
H60.68240.28740.41160.048*
H100.48340.33030.46980.043*
H110.40840.29700.72310.050*
H140.30850.39610.12220.047*
H160.16580.28960.04780.100*
H170.10420.33770.23890.139*
H180.07260.45940.24800.157*
H190.10960.53380.01500.173*
H200.17100.48630.30150.122*
H220.84560.29280.96890.116*
H230.97030.30890.93810.159*
H241.02380.36770.66580.167*
H250.95570.40610.40660.143*
H260.82990.38690.42780.099*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.073 (2)0.082 (2)0.0568 (18)0.0057 (18)0.0340 (17)0.0193 (17)
F20.086 (3)0.087 (3)0.059 (2)0.013 (2)0.0320 (18)0.0172 (18)
O10.037 (2)0.109 (3)0.065 (3)0.004 (2)0.0159 (19)0.025 (2)
O20.047 (2)0.041 (2)0.0400 (18)0.0043 (17)0.0059 (16)0.0132 (16)
O30.054 (2)0.0275 (19)0.0401 (18)0.0041 (17)0.0110 (16)0.0004 (15)
O40.057 (3)0.062 (3)0.075 (3)0.010 (2)0.036 (2)0.021 (2)
N10.044 (3)0.029 (2)0.036 (2)0.004 (2)0.014 (2)0.0021 (19)
N20.043 (3)0.036 (3)0.032 (2)0.006 (2)0.0121 (19)0.011 (2)
C10.042 (3)0.044 (3)0.045 (3)0.011 (3)0.017 (3)0.006 (3)
C20.049 (4)0.055 (4)0.035 (3)0.017 (3)0.014 (3)0.010 (3)
C30.057 (4)0.044 (3)0.041 (3)0.001 (3)0.006 (3)0.012 (2)
C40.044 (3)0.035 (3)0.034 (2)0.001 (2)0.008 (2)0.003 (2)
C50.026 (3)0.032 (3)0.033 (2)0.006 (2)0.001 (2)0.004 (2)
C60.036 (3)0.039 (3)0.046 (3)0.001 (2)0.003 (2)0.001 (2)
C70.032 (3)0.030 (3)0.028 (2)0.004 (2)0.000 (2)0.003 (2)
C80.038 (3)0.030 (3)0.026 (2)0.000 (2)0.001 (2)0.004 (2)
C90.030 (3)0.026 (3)0.029 (2)0.001 (2)0.007 (2)0.0073 (19)
C100.045 (3)0.036 (3)0.025 (2)0.003 (2)0.001 (2)0.003 (2)
C110.057 (4)0.037 (3)0.032 (3)0.003 (3)0.008 (3)0.005 (2)
C120.053 (4)0.034 (3)0.041 (3)0.006 (3)0.017 (3)0.002 (2)
C130.032 (3)0.050 (3)0.048 (3)0.006 (3)0.015 (2)0.002 (3)
C140.046 (3)0.036 (3)0.036 (3)0.000 (2)0.003 (2)0.003 (2)
C150.031 (3)0.081 (5)0.067 (4)0.005 (3)0.018 (3)0.018 (4)
C160.069 (5)0.103 (6)0.080 (5)0.027 (4)0.019 (4)0.004 (5)
C170.087 (7)0.174 (10)0.087 (6)0.011 (7)0.002 (5)0.005 (6)
C180.059 (6)0.198 (14)0.133 (9)0.005 (7)0.012 (6)0.078 (9)
C190.099 (8)0.104 (8)0.227 (14)0.003 (6)0.020 (8)0.083 (9)
C200.083 (6)0.069 (6)0.151 (8)0.008 (4)0.011 (5)0.016 (5)
C210.057 (4)0.047 (4)0.088 (5)0.004 (3)0.046 (4)0.009 (3)
C220.084 (6)0.079 (5)0.133 (6)0.001 (4)0.066 (5)0.005 (5)
C230.099 (9)0.109 (8)0.201 (12)0.015 (6)0.089 (8)0.003 (7)
C240.057 (6)0.118 (9)0.247 (15)0.010 (6)0.059 (8)0.032 (8)
C250.055 (6)0.132 (8)0.169 (9)0.007 (5)0.000 (6)0.007 (6)
C260.060 (5)0.088 (5)0.100 (5)0.002 (4)0.017 (4)0.009 (4)
Geometric parameters (Å, º) top
F1—C121.345 (5)C1—O41.393 (5)
O2—C81.232 (5)C12—C131.396 (7)
C7—O31.225 (5)C3—C21.356 (7)
C7—N11.336 (5)C3—H30.9300
C7—C51.496 (6)C15—C201.345 (8)
F2—C21.350 (5)C15—C161.351 (8)
N1—N21.387 (5)C16—C171.379 (10)
N1—H1N0.87 (4)C16—H160.9300
C8—N21.339 (6)C20—C191.376 (12)
C8—C91.495 (6)C20—H200.9300
C9—C101.377 (6)C19—C181.344 (13)
C9—C141.397 (6)C19—H190.9300
N2—H2N0.83 (4)C18—C171.361 (12)
C5—C41.384 (6)C18—H180.9300
C5—C61.391 (6)C17—H170.9300
C11—C121.365 (6)O4—C211.387 (7)
C11—C101.380 (6)C21—C261.354 (8)
C11—H110.9300C21—C221.371 (8)
C10—H100.9300C22—C231.372 (11)
C4—C31.374 (6)C22—H220.9300
C4—H40.9300C26—C251.392 (9)
C14—C131.381 (6)C26—H260.9300
C14—H140.9300C23—C241.342 (12)
C6—C11.371 (6)C23—H230.9300
C6—H60.9300C24—C251.364 (12)
O1—C131.359 (6)C24—H240.9300
O1—C151.391 (6)C25—H250.9300
C1—C21.381 (7)
O3—C7—N1121.9 (4)C2—C3—C4118.9 (5)
O3—C7—C5122.3 (4)C2—C3—H3120.6
N1—C7—C5115.8 (4)C4—C3—H3120.6
C7—N1—N2119.9 (4)F2—C2—C3120.3 (5)
C7—N1—H1N124 (3)F2—C2—C1118.1 (5)
N2—N1—H1N115 (3)C3—C2—C1121.6 (4)
O2—C8—N2121.5 (4)C20—C15—C16121.2 (7)
O2—C8—C9122.6 (4)C20—C15—O1119.3 (7)
N2—C8—C9115.9 (4)C16—C15—O1119.5 (6)
C10—C9—C14120.0 (4)C15—C16—C17119.2 (8)
C10—C9—C8122.9 (4)C15—C16—H16120.4
C14—C9—C8117.1 (4)C17—C16—H16120.4
C8—N2—N1119.6 (4)C15—C20—C19119.1 (9)
C8—N2—H2N126 (3)C15—C20—H20120.5
N1—N2—H2N114 (3)C19—C20—H20120.5
C4—C5—C6118.9 (4)C18—C19—C20120.9 (10)
C4—C5—C7121.9 (4)C18—C19—H19119.6
C6—C5—C7119.0 (4)C20—C19—H19119.6
C12—C11—C10119.3 (4)C19—C18—C17119.5 (10)
C12—C11—H11120.4C19—C18—H18120.3
C10—C11—H11120.4C17—C18—H18120.3
C9—C10—C11120.1 (5)C18—C17—C16120.1 (9)
C9—C10—H10120.0C18—C17—H17120.0
C11—C10—H10120.0C16—C17—H17120.0
C3—C4—C5121.1 (5)C21—O4—C1117.6 (4)
C3—C4—H4119.4C26—C21—C22121.5 (7)
C5—C4—H4119.4C26—C21—O4123.4 (5)
C13—C14—C9120.7 (4)C22—C21—O4115.1 (7)
C13—C14—H14119.6C23—C22—C21118.6 (8)
C9—C14—H14119.6C23—C22—H22120.7
C1—C6—C5119.9 (5)C21—C22—H22120.7
C1—C6—H6120.0C21—C26—C25118.7 (7)
C5—C6—H6120.0C21—C26—H26120.7
C13—O1—C15118.2 (4)C25—C26—H26120.7
C6—C1—C2119.5 (5)C24—C23—C22120.9 (10)
C6—C1—O4120.5 (5)C24—C23—H23119.5
C2—C1—O4119.9 (4)C22—C23—H23119.5
F1—C12—C11120.0 (4)C23—C24—C25120.5 (10)
F1—C12—C13117.4 (5)C23—C24—H24119.8
C11—C12—C13122.5 (4)C25—C24—H24119.8
O1—C13—C14126.6 (5)C24—C25—C26119.8 (9)
O1—C13—C12116.0 (4)C24—C25—H25120.1
C14—C13—C12117.4 (5)C26—C25—H25120.1
O3—C7—N1—N29.5 (7)F1—C12—C13—C14177.4 (4)
C5—C7—N1—N2170.7 (4)C11—C12—C13—C141.3 (7)
O2—C8—C9—C10148.4 (4)C5—C4—C3—C21.3 (7)
N2—C8—C9—C1029.8 (6)C4—C3—C2—F2179.4 (4)
O2—C8—C9—C1429.3 (6)C4—C3—C2—C11.4 (8)
N2—C8—C9—C14152.4 (4)C6—C1—C2—F2179.1 (4)
O2—C8—N2—N10.5 (7)O4—C1—C2—F22.7 (7)
C9—C8—N2—N1177.8 (4)C6—C1—C2—C31.1 (8)
C7—N1—N2—C8119.3 (5)O4—C1—C2—C3175.3 (5)
O3—C7—C5—C4144.8 (4)C13—O1—C15—C2091.1 (7)
N1—C7—C5—C435.4 (6)C13—O1—C15—C1691.4 (6)
O3—C7—C5—C631.1 (6)C20—C15—C16—C170.1 (10)
N1—C7—C5—C6148.7 (4)O1—C15—C16—C17177.4 (6)
C14—C9—C10—C111.8 (6)C16—C15—C20—C190.1 (11)
C8—C9—C10—C11175.9 (4)O1—C15—C20—C19177.4 (7)
C12—C11—C10—C92.1 (7)C15—C20—C19—C181.1 (15)
C6—C5—C4—C30.8 (7)C20—C19—C18—C172.4 (17)
C7—C5—C4—C3175.1 (4)C19—C18—C17—C162.3 (15)
C10—C9—C14—C130.1 (7)C15—C16—C17—C181.1 (12)
C8—C9—C14—C13177.9 (4)C6—C1—O4—C21109.6 (5)
C4—C5—C6—C10.4 (7)C2—C1—O4—C2174.1 (6)
C7—C5—C6—C1175.6 (4)C1—O4—C21—C2625.8 (8)
C5—C6—C1—C20.5 (7)C1—O4—C21—C22157.2 (5)
C5—C6—C1—O4175.8 (4)C26—C21—C22—C231.0 (11)
C10—C11—C12—F1179.2 (4)O4—C21—C22—C23176.0 (6)
C10—C11—C12—C130.5 (7)C22—C21—C26—C250.2 (10)
C15—O1—C13—C142.0 (8)O4—C21—C26—C25176.9 (6)
C15—O1—C13—C12179.3 (5)C21—C22—C23—C242.0 (14)
C9—C14—C13—O1177.2 (4)C22—C23—C24—C251.8 (17)
C9—C14—C13—C121.6 (7)C23—C24—C25—C260.6 (16)
F1—C12—C13—O13.7 (6)C21—C26—C25—C240.4 (12)
C11—C12—C13—O1177.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.87 (5)2.19 (5)3.047 (6)168 (5)
N2—H2N···O3ii0.84 (4)2.17 (4)3.003 (5)178 (4)
C3—H3···Cg1iii0.932.803.451 (6)128
Symmetry codes: (i) x+1, y+1, z; (ii) x, y+1/2, z+1/2; (iii) x+1, y, z+1.
 

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