4-Fluoro-N′-(4-fluoro-3-phenoxy­benzo­yl)-3-phenoxy­benzohydrazide

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.

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

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

Crystal data

C26H18F2N2O4	F(000) = 952
Mr = 460.42	Dx = 1.387 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 963 reflections
a = 18.375 (4) Å	θ = 1.4–25.2°
b = 18.236 (4) Å	µ = 0.11 mm^−1
c = 6.5954 (15) Å	T = 290 K
β = 93.680 (5)°	Plate, colourless
V = 2205.5 (8) Å^3	0.25 × 0.20 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3865 independent reflections
Radiation source: fine-focus sealed tube	2556 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.082
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→21
Tmin = 0.940, Tmax = 0.990	k = −20→21
15717 measured reflections	l = −7→7

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.098	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.197	H atoms treated by a mixture of independent and constrained refinement
S = 1.29	w = 1/[σ^2(Fo^2) + (0.0504P)^2 + 0.9271P] where P = (Fo^2 + 2Fc^2)/3
3865 reflections	(Δ/σ)max < 0.001
315 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
F1	0.27051 (16)	0.30472 (17)	0.7141 (4)	0.0692 (10)
F2	0.72283 (18)	0.46088 (18)	−0.8405 (4)	0.0761 (10)
O1	0.2084 (2)	0.3548 (2)	0.3743 (6)	0.0697 (12)
O2	0.43013 (17)	0.44754 (17)	−0.0003 (4)	0.0424 (9)
O3	0.56499 (17)	0.27593 (17)	−0.1942 (4)	0.0401 (8)
O4	0.7534 (2)	0.3212 (2)	−0.7226 (5)	0.0637 (11)
N1	0.5601 (2)	0.3867 (2)	−0.0488 (5)	0.0360 (10)
N2	0.5135 (2)	0.3622 (2)	0.0940 (6)	0.0369 (10)
C1	0.7055 (3)	0.3637 (3)	−0.6167 (7)	0.0432 (13)
C2	0.6890 (3)	0.4342 (3)	−0.6804 (7)	0.0457 (14)
C3	0.6388 (3)	0.4754 (3)	−0.5902 (7)	0.0472 (14)
C4	0.6049 (3)	0.4465 (2)	−0.4287 (6)	0.0371 (12)
C5	0.6200 (2)	0.3761 (2)	−0.3603 (6)	0.0304 (11)
C6	0.6713 (2)	0.3347 (3)	−0.4562 (7)	0.0404 (12)
C7	0.5795 (2)	0.3415 (3)	−0.1955 (6)	0.0299 (11)
C8	0.4492 (3)	0.3956 (2)	0.1101 (6)	0.0313 (11)
C9	0.4037 (2)	0.3674 (2)	0.2732 (6)	0.0281 (11)
C10	0.4333 (3)	0.3369 (2)	0.4510 (6)	0.0354 (12)
C11	0.3885 (3)	0.3161 (2)	0.6011 (7)	0.0415 (13)
C12	0.3148 (3)	0.3239 (2)	0.5684 (7)	0.0418 (13)
C13	0.2825 (3)	0.3529 (3)	0.3885 (7)	0.0427 (13)
C14	0.3282 (3)	0.3754 (2)	0.2424 (7)	0.0392 (12)
C15	0.1736 (3)	0.3840 (4)	0.1989 (10)	0.0590 (16)
C16	0.1542 (4)	0.3392 (4)	0.0415 (11)	0.084 (2)
C17	0.1171 (5)	0.3679 (6)	−0.1287 (13)	0.116 (3)
C18	0.0992 (5)	0.4403 (8)	−0.1355 (17)	0.131 (4)
C19	0.1202 (5)	0.4839 (6)	0.022 (2)	0.145 (5)
C20	0.1574 (4)	0.4559 (4)	0.1923 (14)	0.102 (3)
C21	0.8270 (3)	0.3381 (3)	−0.6990 (10)	0.0621 (17)
C22	0.8677 (4)	0.3151 (4)	−0.8540 (12)	0.096 (2)
C23	0.9418 (6)	0.3257 (5)	−0.8361 (19)	0.133 (4)
C24	0.9737 (5)	0.3598 (6)	−0.674 (2)	0.139 (4)
C25	0.9332 (4)	0.3829 (5)	−0.5196 (15)	0.119 (3)
C26	0.8581 (4)	0.3716 (4)	−0.5321 (11)	0.082 (2)
H1N	0.565 (2)	0.434 (3)	−0.053 (7)	0.049 (16)*
H2N	0.528 (2)	0.325 (2)	0.156 (6)	0.029 (14)*
H3	0.6276	0.5224	−0.6370	0.057*
H4	0.5711	0.4748	−0.3642	0.045*
H6	0.6824	0.2874	−0.4116	0.048*
H10	0.4834	0.3303	0.4698	0.043*
H11	0.4084	0.2970	0.7231	0.050*
H14	0.3085	0.3961	0.1222	0.047*
H16	0.1658	0.2896	0.0478	0.100*
H17	0.1042	0.3377	−0.2389	0.139*
H18	0.0726	0.4594	−0.2480	0.157*
H19	0.1096	0.5338	0.0150	0.173*
H20	0.1710	0.4863	0.3015	0.122*
H22	0.8456	0.2928	−0.9689	0.116*
H23	0.9703	0.3089	−0.9381	0.159*
H24	1.0238	0.3677	−0.6658	0.167*
H25	0.9557	0.4061	−0.4066	0.143*
H26	0.8299	0.3869	−0.4278	0.099*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.073 (2)	0.082 (2)	0.0568 (18)	−0.0057 (18)	0.0340 (17)	0.0193 (17)
F2	0.086 (3)	0.087 (3)	0.059 (2)	−0.013 (2)	0.0320 (18)	0.0172 (18)
O1	0.037 (2)	0.109 (3)	0.065 (3)	−0.004 (2)	0.0159 (19)	0.025 (2)
O2	0.047 (2)	0.041 (2)	0.0400 (18)	0.0043 (17)	0.0059 (16)	0.0132 (16)
O3	0.054 (2)	0.0275 (19)	0.0401 (18)	−0.0041 (17)	0.0110 (16)	−0.0004 (15)
O4	0.057 (3)	0.062 (3)	0.075 (3)	−0.010 (2)	0.036 (2)	−0.021 (2)
N1	0.044 (3)	0.029 (2)	0.036 (2)	−0.004 (2)	0.014 (2)	0.0021 (19)
N2	0.043 (3)	0.036 (3)	0.032 (2)	0.006 (2)	0.0121 (19)	0.011 (2)
C1	0.042 (3)	0.044 (3)	0.045 (3)	−0.011 (3)	0.017 (3)	−0.006 (3)
C2	0.049 (4)	0.055 (4)	0.035 (3)	−0.017 (3)	0.014 (3)	0.010 (3)
C3	0.057 (4)	0.044 (3)	0.041 (3)	−0.001 (3)	0.006 (3)	0.012 (2)
C4	0.044 (3)	0.035 (3)	0.034 (2)	−0.001 (2)	0.008 (2)	−0.003 (2)
C5	0.026 (3)	0.032 (3)	0.033 (2)	−0.006 (2)	0.001 (2)	−0.004 (2)
C6	0.036 (3)	0.039 (3)	0.046 (3)	−0.001 (2)	0.003 (2)	−0.001 (2)
C7	0.032 (3)	0.030 (3)	0.028 (2)	0.004 (2)	0.000 (2)	0.003 (2)
C8	0.038 (3)	0.030 (3)	0.026 (2)	0.000 (2)	0.001 (2)	−0.004 (2)
C9	0.030 (3)	0.026 (3)	0.029 (2)	−0.001 (2)	0.007 (2)	−0.0073 (19)
C10	0.045 (3)	0.036 (3)	0.025 (2)	0.003 (2)	−0.001 (2)	−0.003 (2)
C11	0.057 (4)	0.037 (3)	0.032 (3)	0.003 (3)	0.008 (3)	0.005 (2)
C12	0.053 (4)	0.034 (3)	0.041 (3)	−0.006 (3)	0.017 (3)	0.002 (2)
C13	0.032 (3)	0.050 (3)	0.048 (3)	−0.006 (3)	0.015 (2)	−0.002 (3)
C14	0.046 (3)	0.036 (3)	0.036 (3)	0.000 (2)	0.003 (2)	0.003 (2)
C15	0.031 (3)	0.081 (5)	0.067 (4)	0.005 (3)	0.018 (3)	0.018 (4)
C16	0.069 (5)	0.103 (6)	0.080 (5)	0.027 (4)	0.019 (4)	0.004 (5)
C17	0.087 (7)	0.174 (10)	0.087 (6)	0.011 (7)	0.002 (5)	−0.005 (6)
C18	0.059 (6)	0.198 (14)	0.133 (9)	−0.005 (7)	−0.012 (6)	0.078 (9)
C19	0.099 (8)	0.104 (8)	0.227 (14)	−0.003 (6)	−0.020 (8)	0.083 (9)
C20	0.083 (6)	0.069 (6)	0.151 (8)	−0.008 (4)	−0.011 (5)	0.016 (5)
C21	0.057 (4)	0.047 (4)	0.088 (5)	0.004 (3)	0.046 (4)	0.009 (3)
C22	0.084 (6)	0.079 (5)	0.133 (6)	0.001 (4)	0.066 (5)	−0.005 (5)
C23	0.099 (9)	0.109 (8)	0.201 (12)	0.015 (6)	0.089 (8)	−0.003 (7)
C24	0.057 (6)	0.118 (9)	0.247 (15)	0.010 (6)	0.059 (8)	0.032 (8)
C25	0.055 (6)	0.132 (8)	0.169 (9)	−0.007 (5)	0.000 (6)	0.007 (6)
C26	0.060 (5)	0.088 (5)	0.100 (5)	−0.002 (4)	0.017 (4)	−0.009 (4)

Geometric parameters (Å, º)

F1—C12	1.345 (5)	C1—O4	1.393 (5)
O2—C8	1.232 (5)	C12—C13	1.396 (7)
C7—O3	1.225 (5)	C3—C2	1.356 (7)
C7—N1	1.336 (5)	C3—H3	0.9300
C7—C5	1.496 (6)	C15—C20	1.345 (8)
F2—C2	1.350 (5)	C15—C16	1.351 (8)
N1—N2	1.387 (5)	C16—C17	1.379 (10)
N1—H1N	0.87 (4)	C16—H16	0.9300
C8—N2	1.339 (6)	C20—C19	1.376 (12)
C8—C9	1.495 (6)	C20—H20	0.9300
C9—C10	1.377 (6)	C19—C18	1.344 (13)
C9—C14	1.397 (6)	C19—H19	0.9300
N2—H2N	0.83 (4)	C18—C17	1.361 (12)
C5—C4	1.384 (6)	C18—H18	0.9300
C5—C6	1.391 (6)	C17—H17	0.9300
C11—C12	1.365 (6)	O4—C21	1.387 (7)
C11—C10	1.380 (6)	C21—C26	1.354 (8)
C11—H11	0.9300	C21—C22	1.371 (8)
C10—H10	0.9300	C22—C23	1.372 (11)
C4—C3	1.374 (6)	C22—H22	0.9300
C4—H4	0.9300	C26—C25	1.392 (9)
C14—C13	1.381 (6)	C26—H26	0.9300
C14—H14	0.9300	C23—C24	1.342 (12)
C6—C1	1.371 (6)	C23—H23	0.9300
C6—H6	0.9300	C24—C25	1.364 (12)
O1—C13	1.359 (6)	C24—H24	0.9300
O1—C15	1.391 (6)	C25—H25	0.9300
C1—C2	1.381 (7)
O3—C7—N1	121.9 (4)	C2—C3—C4	118.9 (5)
O3—C7—C5	122.3 (4)	C2—C3—H3	120.6
N1—C7—C5	115.8 (4)	C4—C3—H3	120.6
C7—N1—N2	119.9 (4)	F2—C2—C3	120.3 (5)
C7—N1—H1N	124 (3)	F2—C2—C1	118.1 (5)
N2—N1—H1N	115 (3)	C3—C2—C1	121.6 (4)
O2—C8—N2	121.5 (4)	C20—C15—C16	121.2 (7)
O2—C8—C9	122.6 (4)	C20—C15—O1	119.3 (7)
N2—C8—C9	115.9 (4)	C16—C15—O1	119.5 (6)
C10—C9—C14	120.0 (4)	C15—C16—C17	119.2 (8)
C10—C9—C8	122.9 (4)	C15—C16—H16	120.4
C14—C9—C8	117.1 (4)	C17—C16—H16	120.4
C8—N2—N1	119.6 (4)	C15—C20—C19	119.1 (9)
C8—N2—H2N	126 (3)	C15—C20—H20	120.5
N1—N2—H2N	114 (3)	C19—C20—H20	120.5
C4—C5—C6	118.9 (4)	C18—C19—C20	120.9 (10)
C4—C5—C7	121.9 (4)	C18—C19—H19	119.6
C6—C5—C7	119.0 (4)	C20—C19—H19	119.6
C12—C11—C10	119.3 (4)	C19—C18—C17	119.5 (10)
C12—C11—H11	120.4	C19—C18—H18	120.3
C10—C11—H11	120.4	C17—C18—H18	120.3
C9—C10—C11	120.1 (5)	C18—C17—C16	120.1 (9)
C9—C10—H10	120.0	C18—C17—H17	120.0
C11—C10—H10	120.0	C16—C17—H17	120.0
C3—C4—C5	121.1 (5)	C21—O4—C1	117.6 (4)
C3—C4—H4	119.4	C26—C21—C22	121.5 (7)
C5—C4—H4	119.4	C26—C21—O4	123.4 (5)
C13—C14—C9	120.7 (4)	C22—C21—O4	115.1 (7)
C13—C14—H14	119.6	C23—C22—C21	118.6 (8)
C9—C14—H14	119.6	C23—C22—H22	120.7
C1—C6—C5	119.9 (5)	C21—C22—H22	120.7
C1—C6—H6	120.0	C21—C26—C25	118.7 (7)
C5—C6—H6	120.0	C21—C26—H26	120.7
C13—O1—C15	118.2 (4)	C25—C26—H26	120.7
C6—C1—C2	119.5 (5)	C24—C23—C22	120.9 (10)
C6—C1—O4	120.5 (5)	C24—C23—H23	119.5
C2—C1—O4	119.9 (4)	C22—C23—H23	119.5
F1—C12—C11	120.0 (4)	C23—C24—C25	120.5 (10)
F1—C12—C13	117.4 (5)	C23—C24—H24	119.8
C11—C12—C13	122.5 (4)	C25—C24—H24	119.8
O1—C13—C14	126.6 (5)	C24—C25—C26	119.8 (9)
O1—C13—C12	116.0 (4)	C24—C25—H25	120.1
C14—C13—C12	117.4 (5)	C26—C25—H25	120.1
O3—C7—N1—N2	−9.5 (7)	F1—C12—C13—C14	177.4 (4)
C5—C7—N1—N2	170.7 (4)	C11—C12—C13—C14	−1.3 (7)
O2—C8—C9—C10	−148.4 (4)	C5—C4—C3—C2	−1.3 (7)
N2—C8—C9—C10	29.8 (6)	C4—C3—C2—F2	179.4 (4)
O2—C8—C9—C14	29.3 (6)	C4—C3—C2—C1	1.4 (8)
N2—C8—C9—C14	−152.4 (4)	C6—C1—C2—F2	−179.1 (4)
O2—C8—N2—N1	0.5 (7)	O4—C1—C2—F2	−2.7 (7)
C9—C8—N2—N1	−177.8 (4)	C6—C1—C2—C3	−1.1 (8)
C7—N1—N2—C8	−119.3 (5)	O4—C1—C2—C3	175.3 (5)
O3—C7—C5—C4	144.8 (4)	C13—O1—C15—C20	−91.1 (7)
N1—C7—C5—C4	−35.4 (6)	C13—O1—C15—C16	91.4 (6)
O3—C7—C5—C6	−31.1 (6)	C20—C15—C16—C17	−0.1 (10)
N1—C7—C5—C6	148.7 (4)	O1—C15—C16—C17	177.4 (6)
C14—C9—C10—C11	−1.8 (6)	C16—C15—C20—C19	0.1 (11)
C8—C9—C10—C11	175.9 (4)	O1—C15—C20—C19	−177.4 (7)
C12—C11—C10—C9	2.1 (7)	C15—C20—C19—C18	1.1 (15)
C6—C5—C4—C3	0.8 (7)	C20—C19—C18—C17	−2.4 (17)
C7—C5—C4—C3	−175.1 (4)	C19—C18—C17—C16	2.3 (15)
C10—C9—C14—C13	−0.1 (7)	C15—C16—C17—C18	−1.1 (12)
C8—C9—C14—C13	−177.9 (4)	C6—C1—O4—C21	−109.6 (5)
C4—C5—C6—C1	−0.4 (7)	C2—C1—O4—C21	74.1 (6)
C7—C5—C6—C1	175.6 (4)	C1—O4—C21—C26	25.8 (8)
C5—C6—C1—C2	0.5 (7)	C1—O4—C21—C22	−157.2 (5)
C5—C6—C1—O4	−175.8 (4)	C26—C21—C22—C23	1.0 (11)
C10—C11—C12—F1	−179.2 (4)	O4—C21—C22—C23	−176.0 (6)
C10—C11—C12—C13	−0.5 (7)	C22—C21—C26—C25	0.2 (10)
C15—O1—C13—C14	−2.0 (8)	O4—C21—C26—C25	176.9 (6)
C15—O1—C13—C12	179.3 (5)	C21—C22—C23—C24	−2.0 (14)
C9—C14—C13—O1	−177.2 (4)	C22—C23—C24—C25	1.8 (17)
C9—C14—C13—C12	1.6 (7)	C23—C24—C25—C26	−0.6 (16)
F1—C12—C13—O1	−3.7 (6)	C21—C26—C25—C24	−0.4 (12)
C11—C12—C13—O1	177.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2^i	0.87 (5)	2.19 (5)	3.047 (6)	168 (5)
N2—H2N···O3^ii	0.84 (4)	2.17 (4)	3.003 (5)	178 (4)
C3—H3···Cg1^iii	0.93	2.80	3.451 (6)	128

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, −y+1/2, z+1/2; (iii) −x+1, −y, −z+1.