2,4-Difluoro­benzaldehyde benzoyl­hydrazone and 2,4-dichloro­benz­aldehyde benzoyl­hydrazone are isostructural at 120 K with Z′ = 2: complex sheets built from N—H⋯O, C—H⋯O and C—H⋯π(arene) hydrogen bonds

Wardell, S.M.S.V.; Lima Ferreira, M. de; Souza, M.V.N. de; Wardell, J.L.; Low, J.N.; Glidewell, C.

doi:10.1107/S0108270106001995

organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 62| Part 3| March 2006| Pages o118-o121

doi:10.1107/S0108270106001995

2,4-Difluorobenzaldehyde benzoylhydrazone and 2,4-dichlorobenzaldehyde benzoylhydrazone are isostructural at 120 K with Z′ = 2: complex sheets built from N—H⋯O, C—H⋯O and C—H⋯π(arene) hydrogen bonds

Solange M. S. V. Wardell,^a Marcelle de Lima Ferreira,^a Marcus V. N. de Souza,^a James L. Wardell,^b John N. Low ^c and Christopher Glidewell ^d ^*

^aInstituto de Tecnologia em Fármacos, Far-Manguinhos, FIOCRUZ, 21041-250 Rio de Janeiro, RJ, Brazil, ^bInstituto de Química, Departamento de Química Inorgânica, Universidade Federal do Rio de Janeiro, CP 68563, 21945-970 Rio de Janeiro, RJ, Brazil, ^cDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and ^dSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
^*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 16 January 2006; accepted 17 January 2006; online 11 February 2006)

At 120 K, 2,4-difluorobenzaldehyde benzoylhydrazone, C₁₄H₁₀F₂N₂O, (I), and 2,4-dichlorobenzaldehyde benzoylhydrazone, C₁₄H₁₀Cl₂N₂O, (II), are isomorphous and isostructural in P2₁/n with Z′ = 2. In each structure, eight independent hydrogen bonds, viz. two of N—H⋯O type, five of C—H⋯O type and one of C—H⋯π(arene) type, link the molecules into complex sheets, within which two independent one-dimensional substructures can be identified.

Comment

As part of our continuing studies of the supermolecular structures of imines and hydrazones, we now report the structures of the title compounds, (I) and (II) (Figs. 1 and 2, respectively). The title compounds were initially prepared as part of a programme to test and compare the bactericidal activities of aroyl and pyridinoyl benzenecarbaldehyde hydrazones, ArCH=NNHCOPh and ArCH=NNHCOC₅H₅N. The pyridinoyl compounds possessed such activities, but the benzoyl derivatives were found not to be active. While the influence of the pyridine N atom is clear, structural differences may also be of importance.

Compounds (I) and (II) both crystallize with Z′ = 2 in space group P2₁/n. The unit-cell dimensions and atomic coordinates indicate that the two compounds are isomorphous and isostructural. The structure of compound (II) has been reported very recently using diffraction data collected at 294 (2) K (Jing et al., 2005 ), and it is clear that no phase change occurs between 294 and 120 K. Although the N—H⋯O and C—H⋯O hydrogen bonds were identified in the structure of (II), a description of the supramolecular structure was not given.

In each compound, the molecules deviate only slightly from being fully planar, as shown by the values of the five torsion angles defining the conformation of each independent molecule (Table 1). In compound (I), none of these torsion angles deviates from 180° by more than 10° and the deviations indicate clearly that the two molecules selected to form the asymmetric unit of (I) are, in fact, approximately enantiomorphous. A careful search for possible additional crystallographic symmetry, however, revealed none. The precision of the structure determination for compound (II) is rather less good than that for compound (I), but the same conclusions apply. The bond lengths and angles present no unexpected values.

In each of (I) and (II), the molecules are linked into complex sheets by a total of eight independent hydrogen bonds (Tables 2 and 3), and the formation of the sheet is readily analysed in terms of two independent one-dimensional substructures. We discuss in detail here only the supramolecular structure of compound (I). Within the selected asymmetric unit (Fig. 1), the two molecules are linked by three hydrogen bonds, all utilizing atom O47 as the acceptor, and with atoms C17, N21 and C26 as the donors. In an entirely similar way, atoms C37, N41 and C46 at (x, y, z) all act as hydrogen-bond donors to atom O27 at (− $[{1\over 2}]$ + x, $[{1\over 2}]$ − y, − $[{1\over 2}]$ + z), hence forming a complex chain of rings running parallel to the [101] direction, as generated by the n-glide plane at y = $[{1 \over 4}]$ (Fig. 3). This chain contains two independent pairs of edge-fused R₂¹(6) and R₂¹(7) rings (Bernstein et al., 1995 ), and the corresponding pairs of hydrogen bonds generate three independent chains of C₂²(8), C₂²(10) and C₂²(12) types, where the donors are atoms N21 and N41, C26 and C46, and C17 and C37, respectively.

In the second one-dimensional substructure, the bimolecular aggregates (Fig. 1) are linked by a combination of one C—H⋯O hydrogen bond and one C—H⋯π(arene) hydrogen bond. Aryl atom C13 at (x, y, z) acts as donor to atom O27 at ( $[{1\over 2}]$ + x, $[{1\over 2}]$ − y, − $[{1\over 2}]$ + z), while atom C23 at (x, y, z) acts as donor to the fluorinated aryl ring C31–C36 at (− $[{1\over 2}]$ + x, $[{1\over 2}]$ − y, $[{1\over 2}]$ + z). The concerted action of these two hydrogen bonds, together with that of the hydrogen bonds within the asymmetric unit, produces a second chain of rings, this time running parallel to the [10 $[\overline{1}]$ ] direction, but again generated by the n-glide plane at y = $[{1 \over 4}]$ (Fig. 4). The combination of these two chains lying along [101] and [10 $[\overline{1}]$ ] and inclined to one another by ca 70° then generates a very complex sheet lying parallel to (010). Two such sheets, generated by the n-glide planes at y = $[{1 \over 4}]$ and y = $[{3 \over 4}]$ , respectively, and related to one another by inversion, pass through each unit cell, but there are no direction-specific interactions between adjacent sheets.

In compound (II), the N—H⋯O and C—H⋯O hydrogen bonds (Table 3) play exactly the same role as those in compound (I), but the C—H⋯π(arene) hydrogen bond in (II) reinforces the [101] chain, rather than the [10 $[\overline{1}]$ ] chain as in compound (I).

Figure 1
The two independent molecules of compound (I)

, showing the atom-labelling scheme and the three hydrogen bonds (dashed lines) within the selected asymmetric unit. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2
The two independent molecules of compound (II)

, showing the atom-labelling scheme and the three hydrogen bonds (dashed lines) within the selected asymmetric unit. Displacement ellipsoids are drawn at the 30% probability level.

Figure 3
A stereoview of part of the crystal structure of compound (I)

, showing the formation of a hydrogen-bonded chain of rings along [101]. For the sake of clarity, H atoms not involved in the hydrogen bonds shown have been omitted.

Figure 4
A stereoview of part of the crystal structure of compound (II)

, showing the formation of a hydrogen-bonded chain of rings along [10 $[\overline{1}]$ ]. For the sake of clarity, H atoms not involved in the hydrogen bonds shown have been omitted.

Experimental

A solution of benzohydrazide (PhCONHNH₂, 5 mmol) and the appropriate substituted benzaldehyde (5 mmol) in tetrahydrofuran (20 ml) was heated under reflux for 15–18 h under an atmosphere of dinitrogen. After the solution had been cooled, the solvent was removed under reduced pressure and the resulting solid was washed successively with propan-2-ol and diethyl ether. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of solutions in methanol–heptane [3:1 v/v for (I) and 2:1 v/v for (II)]. Analysis for compound (I): yield 78%, m.p. 461–463 K; MS, m/z 260, [M]⁺; ¹H NMR (DMSO-d₆,): δ 7.23 (1H, dd, J = 8.2 and 8.5 Hz, H5), 7.39 (1H, dd, J = 9.4 and 9.2 Hz, H6), 7.55 (2H, dd, J = 7.2 and 7.5 Hz, H3′ and H5′), 7.62 (1H, d, J = 7.2 Hz, H4′), 7.94 (2H, d, J = 7.5 Hz, H2′ and H6′), 8.02 (1H, dd, J = 8.2 and 15.0 Hz, H3′), 8.67 (1H, s, N=C—H), 12.02 (1H, s, NH); ¹³C NMR (DMSO-d₆): δ 104.5 (t, J = 25.0 Hz, C3), 112.7 (dd, J = 2.5 and 22.5 Hz, C5), 118.8 (dd, J = 2.5 and 10.0 Hz, C1), 127.5, 127.7, 128.6, 132.0, 133.2, 139.7 (C=N), 161.0 (dd, J = 12.4 and 250.9 Hz, C4), 163.2, 163.3 (dd, J = 12.2 and 248.2 Hz, C2); IR (KBr pellet, ν, cm⁻¹): 3177 (NH), 1654 (CO). Analysis for compound (II): yield 74%, m.p. 462–464 K; MS, m/z 293, [M]⁺; ¹H NMR (DMSO-d₆): δ 7.55 (1H, d, J = 8.5 Hz, H5), 7.56 (2H, J = 7.5 Hz, H3′ and H5′), 7.62 (1H, d, J = 7.5 Hz, H4′), 7.74 (1H, s, H3), 7.95 (2H, d, J = 7.5 Hz, H2′ and H6′), 8.04 (1H, d, J = 8.5 Hz, H6), 8.83 (1H, s, N=C—H), 12.16 (1H, s, NH); ¹³C NMR (DMSO-d₆): δ 127.5, 128.1, 128.6, 129.4, 130.8, 132.1, 133.0, 133.9, 135.1, 142.5, 166.4; IR (KBr pellet, ν, cm⁻¹): 3086 (NH), 1680 (CO).

Compound (I)

Crystal data

C₁₄H₁₀F₂N₂O
M_r = 260.24
Monoclinic, P 2₁ /n
a = 10.1310 (3) Å
b = 17.2172 (6) Å
c = 14.4288 (5) Å
β = 103.957 (2)°
V = 2442.48 (14) Å³
Z = 8
D_x = 1.415 Mg m⁻³
Mo Kα radiation
Cell parameters from 5577 reflections
θ = 3.0–27.5°
μ = 0.11 mm⁻¹
T = 120 (2) K
Lath, colourless
0.36 × 0.11 × 0.03 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan(SADABS; Sheldrick, 2003 )T_min = 0.973, T_max = 0.997
26932 measured reflections
5577 independent reflections
3589 reflections with I > 2σ(I)
R_int = 0.080
θ_max = 27.5°
h = −13 → 13
k = −21 → 22
l = −18 → 18

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.130
S = 1.04
5577 reflections
343 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0499P)² + 0.8675P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Selected torsion angles (°) for compounds (I) and (II)

Parameter	(I)		(II)
	x = 1, y = 2	x = 3, y = 4	x = 1, y = 2	x = 3, y = 4
Cx1—Cx7—Nx1—Ny1	177.66 (16)	−177.09 (17)	175.3 (3)	−174.9 (3)
Cx7—Nx1—Ny1—Cy7	−177.33 (17)	179.69 (19)	−179.4 (3)	177.3 (3)
Nx1—Ny1—Ny7—Cy1	172.31 (16)	−173.40 (17)	170.4 (3)	−168.8 (3)
Cx2—Cx1—Cx7—Nx1	176.80 (19)	−171.9 (2)	168.6 (4)	−166.3 (3)
Cy2—Cy1—Cy7—Ny1	177.65 (17)	−175.2 (2)	−176.6 (3)	−167.0 (3)

Table 2
Hydrogen-bond geometry (Å, °) for (I)

Cg1 is the centroid of the C31–C36 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N21—H21⋯O47	0.88	2.02	2.889 (2)	170
N41—H41⋯O27ⁱ	0.88	2.12	2.916 (2)	150
C13—H13⋯O27ⁱⁱ	0.95	2.37	3.286 (3)	162
C17—H17⋯O47	0.95	2.47	3.277 (2)	143
C26—H26⋯O47	0.95	2.41	3.340 (3)	167
C37—H37⋯O27ⁱ	0.95	2.50	3.251 (2)	136
C46—H46⋯O27ⁱ	0.95	2.47	3.402 (2)	165
C23—H23⋯Cg1ⁱⁱⁱ	0.95	2.91	3.859 (3)	174
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}},]$ $[z+{\script{1\over 2}}]$ .

Compound (II)

Crystal data

C₁₄H₁₀Cl₂N₂O
M_r = 293.14
Monoclinic, P 2₁ /n
a = 10.5093 (5) Å
b = 17.6499 (9) Å
c = 14.7982 (5) Å
β = 104.732 (2)°
V = 2654.7 (2) Å³
Z = 8
D_x = 1.467 Mg m⁻³
Mo Kα radiation
Cell parameters from 6060 reflections
θ = 3.0–27.5°
μ = 0.48 mm⁻¹
T = 120 (2) K
Needle, colourless
0.12 × 0.03 × 0.03 mm

Data collection

Bruker Nonius KappaCCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)T_min = 0.964, T_max = 0.986
38980 measured reflections
6060 independent reflections
3687 reflections with I > 2σ(I)
R_int = 0.102
θ_max = 27.5°
h = −13 → 13
k = −22 → 22
l = −19 → 19

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.155
S = 1.04
6060 reflections
343 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0527P)² + 3.4899P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.001
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.70 e Å⁻³

Table 3
Hydrogen-bond geometry (Å, °) for (II)

Cg2 is the centroid of the C41–C46 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N21—H21⋯O47	0.88	2.10	2.969 (3)	168
N41—H41⋯O27ⁱ	0.88	2.20	2.989 (4)	150
C13—H13⋯O27ⁱⁱ	0.95	2.47	3.425 (4)	179
C17—H17⋯O47	0.95	2.49	3.311 (4)	145
C26—H26⋯O47	0.95	2.41	3.354 (4)	171
C37—H37⋯O27ⁱ	0.95	2.59	3.300 (4)	131
C46—H46⋯O27ⁱ	0.95	2.44	3.381 (4)	170
C35—H35⋯Cg2ⁱⁱⁱ	0.95	2.88	3.480 (5)	122
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}},]$ $[ z+{\script{1\over 2}}]$ .

For both compounds, the space group P2₁/n was uniquely assigned from the systematic absences. All H atoms were located in difference maps and subsequently treated as riding atoms, with distances C—H = 0.95 Å and N—H = 0.88 Å, and with U_iso(H) = 1.2U_eq(C,N).

For both compounds, data collection: COLLECT (Nonius, 1999 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003 ) and SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I, II. DOI: 10.1107/S0108270106001995/sk1895sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270106001995/sk1895Isup2.hkl

Structure factors: contains datablock II. DOI: 10.1107/S0108270106001995/sk1895IIsup3.hkl

Comment top

As part of our continuing studies of the supermolecular structures of imines and hydrazones, we now report the structures of the title compounds, (I) and (II) (Figs. 1 and 2, respectively). The title compounds were initially prepared as part of a programme to test and compare the bactericidal activities of aroyl and pyridinoyl benzenecarboxaldehydehydrazones, ArCH═NNHCOPh and ArCH═ NNHCOC₅H₅N. The pyridinoyl compounds possessed such activities, but the benzoyl derivatives were found not to be active. While the influence of the pyridine N atom is clear, structural differences may also be of importance.

Compounds (I) and (II) both crystallize with Z' = 2 in space group P2₁/n. The unit-cell dimensions and atomic coordinates indicate that the two compounds are isomorphous and isostructural. The structure of compound (II) has been reported very recently using diffraction data collected at 294 (2) K (Jing et al., 2005), and it is clear that no phase change occurs between 294 and 120 K. Although those authors identified the N—H.·O and C—H.·O hydrogen bonds in the structure of (II), they did not give any description of the supramolecular structure, as provided here.

In each of (I) and (II), the molecules are linked into complex sheets by a total of eight independent hydrogen bonds (Tables 2 and 3), and the formation of the sheet is readily analysed in terms of two independent one-dimensional sub-structures. We discuss in detail here only the supramolecular structure of compound (I). Within the selected asymmetric unit (Fig. 1), the two molecules are linked by three hydrogen bonds, all utilizing atom O47 as the acceptor, and with atoms C17, N21 and C26 as the donors. In an entirely similar way, the atoms C37, N41 and C46 at (x, y, z) all act as hydrogen-bond donors to atom O27 at (−1/2 + x, 1/2 − y, −1/2 + z), hence forming a complex chain of rings running parallel to the [101] direction, as generated by the n-glide plane at y = 1/4 (Fig. 3). This chain contains two independent pairs of edge-fused R₂¹(6) and R₂¹(7) rings (Bernstein et al., 1995), and the corresponding pairs of hydrogen bonds generate three independent chains of C₂²(8), C₂²(10) and C₂²(12) types, where the donors are atoms N21 and N41, C26 and C46, and C17 and C37, respectively.

In the second one-dimensional sub-structure, the bimolecular aggregates (Fig. 1) are linked by a combination of one C—H···O hydrogen bond and one C—H..π(arene) hydrogen bond. Aryl atom C13 at (x, y, z) acts as donor to atom O27 at (1/2 + x, 1/2 − y, −1/2 + z), while atom C23 at (x, y, z) acts as donor to the fluorinated aryl ring C31–C36 at (−1/2 + x, 1/2 − y, 1/2 + z). The concerted action of these two hydrogen bonds, together with that of the hydrogen bonds within the asymmetric unit, produces a second chain of rings, this time running parallel to the [101] direction, but again generated by the n-glide plane at y = 1/4 (Fig. 4). The combination of these two chains lying along [101] and [101] and inclined to one another by ca 70° then generates a very complex sheet lying parallel to (010). Two such sheets, generated by the n-glide planes at y = 1/4 and y = 3/4, respectively, and related to one another by inversion, pass through each unit cell, but there are no direction-specific interactions between adjacent sheets.

In compound (II), the N—H···O and C—H.·O hydrogen bonds (Table 3) play exactly the same role as those in compound (I), but the C—H···π(arene) hydrogen bond in (II) reinforces the [101] chain, rather than the [101] chain as in compound (I).

Experimental top

A solution of benzhydrazide (PhCONHNH₂, 5 mmol) and the appropriate substituted benzaldehyde (5 mmol) in tetrahydrofuran (20 ml) was heated under reflux for 15–18 h in an atmosphere of dinitrogen. After the solution had been cooled, the solvent was removed under reduced pressure and the resulting solid was washed successively with propan-2-ol and ethyl [Diethyl?] ether. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of solutions in methanol–heptane [3:1 v/v for (I), and 2:1 v/v for (II)]. Analysis for compound (I): yield 78%, m.p. 461–463 K; MS, m/z 260, [M]⁺; ¹H NMR (DMSO-d₆, δ, p.p.m.): 7.23 (1H, dd, J = 8.2 and 8.5 Hz, H5), 7.39 (1H, dd, J = 9.4 and 9.2 Hz, H6), 7.55 (2H, dd, J = 7.2 and 7.5 Hz, H3' and H5'), 7.62 (1H, d, J = 7.2 Hz, H4'), 7.94 (2H, d, J = 7.5 Hz, H2' and H6'), 8.02 (1H, dd, J = 8.2 and 15.0 Hz, H3'), 8.67 (1H, s, N═C—H), 12.02 (1H, s, NH); ¹³C NMR (DMSO-d₆, δ, p.p.m.): 104.5 (t, J = 25.0 Hz, C3), 112.7 (dd, J = 2.5 and 22.5 Hz, C5), 118.8 (dd, J = 2.5 and 10.0 Hz, C1), 127.5, 127.7, 128.6, 132.0, 133.2, 139.7 (C═N), 161.0 (dd, J = 12.4 and 250.9 Hz, C4), 163.2, 163.3 (dd, J = 12.2 and 248.2 Hz, C2); IR (KBr pellet, ν, cm⁻¹): 3177 (NH), 1654 (CO). Analysis for compound (II): yield 74%, m.p. 462–464 K; MS, m/z 293, [M]⁺; ¹H NMR (DMSO-d₆, δ, p.p.m.): 7.55 (1H, d, J = 8.5 Hz, H5), 7.56 (2H, J = 7.5 Hz, H3' and H5'), 7.62 (1H, d, J = 7.5 Hz, H4'), 7.74 (1H, s, H3), 7.95 (2H, d, J = 7.5 Hz, H2' and H6'), 8.04 (1H, d, J = 8.5 Hz, H6), 8.83 (1H, s, N═C—H), 12.16 (1H, s, NH); ¹³C NMR (DMSO-d₆, δ, p.p.m.): 127.5, 128.1, 128.6, 129.4, 130.8, 132.1, 133.0, 133.9, 135.1, 142.5, 166.4; IR (KBr pellet, ν, cm⁻¹): 3086 (NH), 1680 (CO).

Computing details top

For both compounds, data collection: COLLECT (Nonius, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top

	Fig. 1. The two independent molecules of compound (I), showing the atom-labelling scheme and the three hydrogen bonds (dashed lines) within the selected asymmetric unit. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The two independent molecules of compound (II), showing the atom-labelling scheme and the three hydrogen bonds (dashed lines) within the selected asymmetric unit. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 3. A stereoview of part of the crystal structure of compound (I), showing the formation of a hydrogen-bonded chain of rings along [101]. For the sake of clarity, H atoms not involved in the hydrogen bonds shown have been omitted.
	Fig. 4. A stereoview of part of the crystal structure of compound (I), showing the formation of a hydrogen-bonded chain of rings along [101]. For the sake of clarity, H atoms not involved in the hydrogen bonds shown have been omitted.

(I) 2,4-difluorobenzaldehyde benzoylhydrazone top

Crystal data top

C₁₄H₁₀F₂N₂O	F(000) = 1072
M_r = 260.24	D_x = 1.415 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5577 reflections
a = 10.1310 (3) Å	θ = 3.0–27.5°
b = 17.2172 (6) Å	µ = 0.11 mm⁻¹
c = 14.4288 (5) Å	T = 120 K
β = 103.957 (2)°	Lath, colourless
V = 2442.48 (14) Å³	0.36 × 0.11 × 0.03 mm
Z = 8

Data collection top

Bruker Nonius KappaCCD area-detector diffractometer	5577 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	3589 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.080
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ϕ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −21→22
T_min = 0.973, T_max = 0.997	l = −18→18
26932 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0499P)² + 0.8675P] where P = (F_o² + 2F_c²)/3
5577 reflections	(Δ/σ)_max < 0.001
343 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₄H₁₀F₂N₂O	V = 2442.48 (14) Å³
M_r = 260.24	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.1310 (3) Å	µ = 0.11 mm⁻¹
b = 17.2172 (6) Å	T = 120 K
c = 14.4288 (5) Å	0.36 × 0.11 × 0.03 mm
β = 103.957 (2)°

Data collection top

Bruker Nonius KappaCCD area-detector diffractometer	5577 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	3589 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.997	R_int = 0.080
26932 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.04	Δρ_max = 0.20 e Å⁻³
5577 reflections	Δρ_min = −0.29 e Å⁻³
343 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C11	0.99764 (19)	0.27524 (11)	0.42068 (15)	0.0239 (4)
C12	1.0390 (2)	0.25610 (12)	0.33871 (15)	0.0265 (5)
F12	0.94624 (12)	0.25951 (8)	0.25303 (9)	0.0423 (4)
C13	1.1691 (2)	0.23343 (12)	0.33807 (15)	0.0294 (5)
C14	1.26080 (19)	0.23045 (12)	0.42535 (16)	0.0279 (5)
F14	1.39040 (12)	0.20814 (8)	0.42768 (10)	0.0419 (4)
C15	1.2284 (2)	0.24928 (11)	0.50982 (16)	0.0277 (5)
C16	1.09665 (19)	0.27149 (12)	0.50665 (15)	0.0259 (5)
C17	0.85690 (19)	0.29890 (11)	0.41486 (15)	0.0253 (5)
N11	0.81731 (15)	0.31313 (9)	0.49087 (12)	0.0236 (4)
N21	0.68381 (15)	0.33782 (9)	0.47659 (12)	0.0246 (4)
C27	0.63571 (19)	0.35462 (11)	0.55360 (15)	0.0224 (4)
O27	0.70367 (13)	0.34086 (8)	0.63547 (10)	0.0281 (3)
C21	0.49811 (18)	0.39067 (11)	0.53653 (15)	0.0231 (4)
C22	0.4473 (2)	0.40510 (12)	0.61610 (16)	0.0295 (5)
C23	0.3216 (2)	0.44082 (13)	0.60593 (18)	0.0374 (6)
C24	0.2462 (2)	0.46161 (13)	0.51643 (18)	0.0372 (6)
C25	0.2953 (2)	0.44722 (12)	0.43656 (17)	0.0329 (5)
C26	0.42156 (19)	0.41249 (11)	0.44662 (16)	0.0268 (5)
C31	0.61992 (18)	0.07412 (11)	0.28898 (15)	0.0235 (4)
C32	0.61079 (19)	−0.00380 (12)	0.26511 (16)	0.0278 (5)
F32	0.51203 (13)	−0.02688 (7)	0.18904 (11)	0.0494 (4)
C33	0.6983 (2)	−0.05991 (12)	0.31253 (17)	0.0314 (5)
C34	0.8001 (2)	−0.03505 (12)	0.38748 (16)	0.0318 (5)
F34	0.88836 (13)	−0.08888 (7)	0.43573 (10)	0.0469 (4)
C35	0.8163 (2)	0.04103 (13)	0.41593 (17)	0.0387 (6)
C36	0.7253 (2)	0.09501 (12)	0.36670 (16)	0.0321 (5)
C37	0.52320 (19)	0.13100 (12)	0.23681 (15)	0.0257 (5)
N31	0.54556 (15)	0.20317 (10)	0.25460 (12)	0.0247 (4)
N41	0.44667 (15)	0.25306 (9)	0.20581 (12)	0.0246 (4)
C47	0.46447 (19)	0.33006 (12)	0.22207 (14)	0.0243 (4)
O47	0.56955 (13)	0.35678 (8)	0.27418 (10)	0.0277 (3)
C41	0.34917 (19)	0.38236 (11)	0.17673 (14)	0.0243 (4)
C42	0.3717 (2)	0.46184 (12)	0.18762 (16)	0.0335 (5)
C43	0.2679 (2)	0.51418 (13)	0.15371 (17)	0.0405 (6)
C44	0.1399 (2)	0.48801 (13)	0.10782 (17)	0.0360 (6)
C45	0.1168 (2)	0.40922 (13)	0.09610 (17)	0.0352 (6)
C46	0.2200 (2)	0.35639 (12)	0.12975 (15)	0.0301 (5)
H13	1.1941	0.2206	0.2806	0.035*
H15	1.2950	0.2470	0.5687	0.033*
H16	1.0726	0.2846	0.5644	0.031*
H17	0.7947	0.3037	0.3543	0.030*
H21	0.6404	0.3456	0.4167	0.030*
H22	0.4988	0.3905	0.6777	0.035*
H23	0.2876	0.4509	0.6606	0.045*
H24	0.1602	0.4859	0.5096	0.045*
H25	0.2427	0.4611	0.3750	0.039*
H26	0.4560	0.4035	0.3919	0.032*
H33	0.6886	−0.1130	0.2943	0.038*
H35	0.8882	0.0562	0.4682	0.046*
H36	0.7346	0.1478	0.3862	0.039*
H37	0.4448	0.1146	0.1903	0.031*
H41	0.3719	0.2359	0.1665	0.030*
H42	0.4595	0.4804	0.2188	0.040*
H43	0.2846	0.5683	0.1620	0.049*
H44	0.0684	0.5239	0.0845	0.043*
H45	0.0289	0.3911	0.0645	0.042*
H46	0.2029	0.3023	0.1208	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.0253 (10)	0.0206 (10)	0.0251 (12)	0.0019 (8)	0.0043 (9)	0.0016 (9)
C12	0.0297 (10)	0.0279 (11)	0.0199 (11)	0.0048 (9)	0.0020 (9)	−0.0008 (9)
F12	0.0417 (7)	0.0572 (9)	0.0245 (7)	0.0154 (6)	0.0013 (6)	−0.0036 (6)
C13	0.0352 (11)	0.0310 (11)	0.0251 (12)	0.0070 (9)	0.0137 (10)	0.0013 (9)
C14	0.0232 (10)	0.0262 (11)	0.0358 (13)	0.0049 (8)	0.0103 (9)	0.0025 (10)
F14	0.0285 (6)	0.0514 (8)	0.0481 (9)	0.0108 (6)	0.0138 (6)	0.0014 (7)
C15	0.0256 (10)	0.0291 (11)	0.0271 (12)	−0.0001 (9)	0.0038 (9)	0.0025 (9)
C16	0.0258 (10)	0.0278 (11)	0.0245 (12)	0.0002 (9)	0.0069 (9)	−0.0002 (9)
C17	0.0257 (10)	0.0261 (11)	0.0223 (12)	0.0014 (8)	0.0026 (9)	0.0001 (9)
N11	0.0187 (8)	0.0264 (9)	0.0246 (10)	0.0022 (7)	0.0029 (7)	0.0008 (7)
N21	0.0195 (8)	0.0303 (9)	0.0220 (10)	0.0046 (7)	0.0012 (7)	0.0013 (7)
C27	0.0230 (9)	0.0191 (10)	0.0240 (12)	−0.0017 (8)	0.0037 (9)	−0.0011 (8)
O27	0.0271 (7)	0.0347 (8)	0.0217 (8)	0.0035 (6)	0.0040 (6)	0.0044 (6)
C21	0.0197 (9)	0.0203 (10)	0.0287 (12)	−0.0014 (8)	0.0050 (9)	−0.0010 (9)
C22	0.0282 (10)	0.0304 (11)	0.0309 (13)	0.0012 (9)	0.0087 (9)	0.0004 (10)
C23	0.0318 (11)	0.0405 (13)	0.0448 (15)	0.0035 (10)	0.0188 (11)	−0.0039 (11)
C24	0.0229 (10)	0.0325 (12)	0.0565 (17)	0.0045 (9)	0.0100 (11)	0.0014 (11)
C25	0.0250 (10)	0.0323 (12)	0.0393 (14)	0.0066 (9)	0.0039 (10)	0.0035 (10)
C26	0.0257 (10)	0.0257 (10)	0.0287 (12)	0.0014 (8)	0.0062 (9)	0.0000 (9)
C31	0.0214 (9)	0.0255 (10)	0.0239 (12)	−0.0012 (8)	0.0059 (8)	0.0001 (9)
C32	0.0193 (9)	0.0322 (11)	0.0298 (12)	−0.0031 (9)	0.0016 (9)	−0.0054 (10)
F32	0.0393 (7)	0.0364 (8)	0.0587 (10)	0.0018 (6)	−0.0154 (7)	−0.0141 (7)
C33	0.0299 (11)	0.0242 (10)	0.0406 (14)	−0.0003 (9)	0.0093 (10)	−0.0008 (10)
C34	0.0287 (11)	0.0285 (11)	0.0356 (14)	0.0042 (9)	0.0028 (10)	0.0062 (10)
F34	0.0449 (8)	0.0322 (7)	0.0542 (9)	0.0083 (6)	−0.0066 (7)	0.0099 (6)
C35	0.0392 (12)	0.0315 (12)	0.0370 (14)	−0.0003 (10)	−0.0070 (11)	0.0032 (10)
C36	0.0370 (12)	0.0239 (11)	0.0319 (13)	−0.0011 (9)	0.0013 (10)	−0.0023 (9)
C37	0.0224 (10)	0.0279 (11)	0.0257 (12)	−0.0003 (8)	0.0037 (9)	−0.0010 (9)
N31	0.0221 (8)	0.0285 (9)	0.0228 (10)	0.0040 (7)	0.0037 (7)	0.0024 (7)
N41	0.0201 (8)	0.0251 (9)	0.0248 (10)	0.0027 (7)	−0.0022 (7)	−0.0002 (7)
C47	0.0242 (10)	0.0294 (11)	0.0190 (11)	0.0003 (8)	0.0049 (9)	0.0001 (9)
O47	0.0248 (7)	0.0293 (8)	0.0246 (8)	−0.0028 (6)	−0.0027 (6)	−0.0019 (6)
C41	0.0275 (10)	0.0252 (10)	0.0190 (11)	0.0020 (8)	0.0032 (8)	0.0016 (9)
C42	0.0323 (11)	0.0278 (11)	0.0357 (14)	0.0003 (9)	−0.0008 (10)	−0.0014 (10)
C43	0.0490 (14)	0.0259 (11)	0.0410 (15)	0.0045 (10)	−0.0003 (12)	−0.0017 (11)
C44	0.0374 (12)	0.0347 (13)	0.0333 (14)	0.0121 (10)	0.0033 (10)	0.0042 (10)
C45	0.0264 (11)	0.0399 (13)	0.0354 (14)	0.0029 (10)	−0.0002 (10)	0.0053 (11)
C46	0.0281 (10)	0.0296 (11)	0.0301 (13)	0.0015 (9)	0.0019 (9)	0.0034 (10)

Geometric parameters (Å, º) top

C11—C12	1.386 (3)	C31—C32	1.383 (3)
C11—C16	1.396 (3)	C31—C36	1.396 (3)
C11—C17	1.466 (3)	C31—C37	1.459 (3)
C12—F12	1.362 (2)	C32—F32	1.354 (2)
C12—C13	1.378 (3)	C32—C33	1.376 (3)
C13—C14	1.374 (3)	C33—C34	1.371 (3)
C13—H13	0.95	C33—H33	0.95
C14—F14	1.361 (2)	C34—F34	1.358 (2)
C14—C15	1.375 (3)	C34—C35	1.371 (3)
C15—C16	1.379 (3)	C35—C36	1.379 (3)
C15—H15	0.95	C35—H35	0.95
C16—H16	0.95	C36—H36	0.95
C17—N11	1.279 (3)	C37—N31	1.278 (3)
C17—H17	0.95	C37—H37	0.95
N11—N21	1.385 (2)	N31—N41	1.377 (2)
N21—C27	1.348 (3)	N41—C47	1.351 (3)
N21—H21	0.88	N41—H41	0.88
C27—O27	1.238 (2)	C47—O47	1.235 (2)
C27—C21	1.491 (3)	C47—C41	1.495 (3)
C21—C22	1.389 (3)	C41—C42	1.390 (3)
C21—C26	1.393 (3)	C41—C46	1.394 (3)
C22—C23	1.390 (3)	C42—C43	1.381 (3)
C22—H22	0.95	C42—H42	0.95
C23—C24	1.380 (3)	C43—C44	1.382 (3)
C23—H23	0.95	C43—H43	0.95
C24—C25	1.383 (3)	C44—C45	1.380 (3)
C24—H24	0.95	C44—H44	0.95
C25—C26	1.388 (3)	C45—C46	1.383 (3)
C25—H25	0.95	C45—H45	0.95
C26—H26	0.95	C46—H46	0.95

C12—C11—C16	116.55 (18)	C32—C31—C36	116.25 (18)
C12—C11—C17	120.46 (18)	C32—C31—C37	121.76 (18)
C16—C11—C17	122.98 (19)	C36—C31—C37	121.98 (18)
F12—C12—C13	117.26 (19)	F32—C32—C33	117.27 (18)
F12—C12—C11	118.71 (17)	F32—C32—C31	118.59 (18)
C13—C12—C11	124.03 (19)	C33—C32—C31	124.12 (19)
C14—C13—C12	116.2 (2)	C34—C33—C32	116.42 (19)
C14—C13—H13	121.9	C34—C33—H33	121.8
C12—C13—H13	121.9	C32—C33—H33	121.8
F14—C14—C13	117.92 (19)	F34—C34—C35	118.84 (19)
F14—C14—C15	118.66 (18)	F34—C34—C33	117.96 (19)
C13—C14—C15	123.42 (18)	C35—C34—C33	123.20 (19)
C14—C15—C16	118.16 (19)	C34—C35—C36	118.2 (2)
C14—C15—H15	120.9	C34—C35—H35	120.9
C16—C15—H15	120.9	C36—C35—H35	120.9
C15—C16—C11	121.7 (2)	C35—C36—C31	121.8 (2)
C15—C16—H16	119.2	C35—C36—H36	119.1
C11—C16—H16	119.2	C31—C36—H36	119.1
N11—C17—C11	120.40 (18)	N31—C37—C31	118.97 (18)
N11—C17—H17	119.8	N31—C37—H37	120.5
C11—C17—H17	119.8	C31—C37—H37	120.5
C17—N11—N21	115.35 (16)	C37—N31—N41	115.59 (16)
C27—N21—N11	118.51 (16)	C47—N41—N31	118.24 (16)
C27—N21—H21	125.6	C47—N41—H41	120.0
N11—N21—H21	115.6	N31—N41—H41	121.8
O27—C27—N21	121.13 (18)	O47—C47—N41	122.07 (18)
O27—C27—C21	121.32 (19)	O47—C47—C41	120.66 (18)
N21—C27—C21	117.55 (17)	N41—C47—C41	117.24 (16)
C22—C21—C26	119.18 (18)	C42—C41—C46	118.67 (18)
C22—C21—C27	117.11 (18)	C42—C41—C47	117.00 (17)
C26—C21—C27	123.67 (19)	C46—C41—C47	124.22 (18)
C21—C22—C23	120.3 (2)	C43—C42—C41	120.8 (2)
C21—C22—H22	119.8	C43—C42—H42	119.6
C23—C22—H22	119.8	C41—C42—H42	119.6
C24—C23—C22	120.0 (2)	C42—C43—C44	120.2 (2)
C24—C23—H23	120.0	C42—C43—H43	119.9
C22—C23—H23	120.0	C44—C43—H43	119.9
C23—C24—C25	120.3 (2)	C45—C44—C43	119.4 (2)
C23—C24—H24	119.9	C45—C44—H44	120.3
C25—C24—H24	119.9	C43—C44—H44	120.3
C24—C25—C26	119.8 (2)	C44—C45—C46	120.8 (2)
C24—C25—H25	120.1	C44—C45—H45	119.6
C26—C25—H25	120.1	C46—C45—H45	119.6
C25—C26—C21	120.4 (2)	C45—C46—C41	120.1 (2)
C25—C26—H26	119.8	C45—C46—H46	119.9
C21—C26—H26	119.8	C41—C46—H46	119.9

C16—C11—C12—F12	−179.48 (18)	C36—C31—C32—F32	−178.66 (19)
C17—C11—C12—F12	−0.2 (3)	C37—C31—C32—F32	2.4 (3)
C16—C11—C12—C13	0.7 (3)	C36—C31—C32—C33	−0.3 (3)
C17—C11—C12—C13	179.93 (19)	C37—C31—C32—C33	−179.2 (2)
F12—C12—C13—C14	180.00 (18)	F32—C32—C33—C34	178.0 (2)
C11—C12—C13—C14	−0.1 (3)	C31—C32—C33—C34	−0.3 (3)
C12—C13—C14—F14	179.87 (18)	C32—C33—C34—F34	−179.87 (19)
C12—C13—C14—C15	−0.6 (3)	C32—C33—C34—C35	0.4 (4)
F14—C14—C15—C16	−179.74 (17)	F34—C34—C35—C36	−179.6 (2)
C13—C14—C15—C16	0.7 (3)	C33—C34—C35—C36	0.1 (4)
C14—C15—C16—C11	−0.1 (3)	C34—C35—C36—C31	−0.8 (4)
C12—C11—C16—C15	−0.5 (3)	C32—C31—C36—C35	0.9 (3)
C17—C11—C16—C15	−179.76 (18)	C37—C31—C36—C35	179.8 (2)
C12—C11—C17—N11	176.80 (19)	C32—C31—C37—N31	−171.9 (2)
C16—C11—C17—N11	−4.0 (3)	C36—C31—C37—N31	9.2 (3)
C11—C17—N11—N21	177.66 (16)	C31—C37—N31—N41	−177.09 (17)
C17—N11—N21—C27	−179.33 (17)	C37—N31—N41—C47	179.69 (19)
N11—N21—C27—O27	−7.4 (3)	N31—N41—C47—O47	4.6 (3)
N11—N21—C27—C21	172.31 (16)	N31—N41—C47—C41	−173.40 (17)
O27—C27—C21—C22	−2.6 (3)	O47—C47—C41—C42	6.7 (3)
N21—C27—C21—C22	177.65 (17)	N41—C47—C41—C42	−175.2 (2)
O27—C27—C21—C26	175.21 (18)	O47—C47—C41—C46	−169.4 (2)
N21—C27—C21—C26	−4.5 (3)	N41—C47—C41—C46	8.7 (3)
C26—C21—C22—C23	0.0 (3)	C46—C41—C42—C43	0.8 (3)
C27—C21—C22—C23	177.97 (19)	C47—C41—C42—C43	−175.5 (2)
C21—C22—C23—C24	0.5 (3)	C41—C42—C43—C44	−0.3 (4)
C22—C23—C24—C25	−0.1 (3)	C42—C43—C44—C45	−0.1 (4)
C23—C24—C25—C26	−0.7 (3)	C43—C44—C45—C46	0.1 (4)
C24—C25—C26—C21	1.2 (3)	C44—C45—C46—C41	0.4 (4)
C22—C21—C26—C25	−0.9 (3)	C42—C41—C46—C45	−0.8 (3)
C27—C21—C26—C25	−178.67 (19)	C47—C41—C46—C45	175.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···O47	0.88	2.02	2.889 (2)	170
N41—H41···O27ⁱ	0.88	2.12	2.916 (2)	150
C13—H13···O27ⁱⁱ	0.95	2.37	3.286 (3)	162
C17—H17···O47	0.95	2.47	3.277 (2)	143
C26—H26···O47	0.95	2.41	3.340 (3)	167
C37—H37···O27ⁱ	0.95	2.50	3.251 (2)	136
C46—H46···O27ⁱ	0.95	2.47	3.402 (2)	165
C23—H23···Cg1ⁱⁱⁱ	0.95	2.91	3.859 (3)	174

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

(II) 2,4-dichlorobenzaldehyde benzoylhydrazone top

Crystal data top

C₁₄H₁₀Cl₂N₂O	F(000) = 1200
M_r = 293.14	D_x = 1.467 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6060 reflections
a = 10.5093 (5) Å	θ = 3.0–27.5°
b = 17.6499 (9) Å	µ = 0.48 mm⁻¹
c = 14.7982 (5) Å	T = 120 K
β = 104.732 (2)°	Needle, colourless
V = 2654.7 (2) Å³	0.12 × 0.03 × 0.03 mm
Z = 8

Data collection top

Bruker Nonius KappaCCD area-detector diffractometer	6060 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	3687 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.102
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ϕ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −22→22
T_min = 0.964, T_max = 0.986	l = −19→19
38980 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.155	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0527P)² + 3.4899P] where P = (F_o² + 2F_c²)/3
6060 reflections	(Δ/σ)_max = 0.001
343 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.70 e Å⁻³

Crystal data top

C₁₄H₁₀Cl₂N₂O	V = 2654.7 (2) Å³
M_r = 293.14	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.5093 (5) Å	µ = 0.48 mm⁻¹
b = 17.6499 (9) Å	T = 120 K
c = 14.7982 (5) Å	0.12 × 0.03 × 0.03 mm
β = 104.732 (2)°

Data collection top

Bruker Nonius KappaCCD area-detector diffractometer	6060 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	3687 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.986	R_int = 0.102
38980 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.155	H-atom parameters constrained
S = 1.04	Δρ_max = 0.53 e Å⁻³
6060 reflections	Δρ_min = −0.70 e Å⁻³
343 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C11	0.9744 (3)	0.2791 (2)	0.4130 (2)	0.0297 (8)
C12	1.0069 (4)	0.2530 (2)	0.3333 (2)	0.0366 (9)
Cl12	0.88367 (11)	0.24508 (8)	0.22962 (7)	0.0652 (4)
C13	1.1341 (4)	0.2319 (2)	0.3322 (2)	0.0373 (9)
C14	1.2304 (3)	0.2401 (2)	0.4129 (2)	0.0316 (8)
Cl14	1.38988 (9)	0.21204 (6)	0.41435 (7)	0.0436 (3)
C15	1.2047 (3)	0.2684 (2)	0.4935 (2)	0.0378 (9)
C16	1.0782 (3)	0.2879 (2)	0.4932 (2)	0.0345 (8)
C17	0.8401 (3)	0.30026 (19)	0.4129 (2)	0.0299 (8)
N11	0.8088 (2)	0.31225 (16)	0.48924 (18)	0.0276 (6)
N21	0.6809 (2)	0.33750 (15)	0.47809 (18)	0.0269 (6)
C27	0.6388 (3)	0.35245 (19)	0.5553 (2)	0.0272 (7)
O27	0.7063 (2)	0.33619 (14)	0.63429 (15)	0.0317 (5)
C21	0.5089 (3)	0.39111 (19)	0.5402 (2)	0.0273 (7)
C22	0.4681 (3)	0.4105 (2)	0.6196 (2)	0.0342 (8)
C23	0.3509 (3)	0.4491 (2)	0.6110 (3)	0.0405 (9)
C24	0.2736 (3)	0.4686 (2)	0.5233 (3)	0.0380 (9)
C25	0.3138 (3)	0.4495 (2)	0.4452 (3)	0.0374 (9)
C26	0.4316 (3)	0.4117 (2)	0.4533 (2)	0.0307 (8)
C31	0.6153 (3)	0.08524 (19)	0.2827 (2)	0.0282 (7)
C32	0.6209 (3)	0.0106 (2)	0.2537 (2)	0.0319 (8)
Cl32	0.52231 (9)	−0.01937 (6)	0.14709 (7)	0.0473 (3)
C33	0.7043 (3)	−0.0421 (2)	0.3072 (3)	0.0365 (8)
C34	0.7821 (4)	−0.0205 (2)	0.3925 (3)	0.0386 (9)
Cl34	0.88383 (11)	−0.08745 (6)	0.46080 (8)	0.0576 (3)
C35	0.7790 (4)	0.0525 (2)	0.4258 (3)	0.0393 (9)
C36	0.6955 (3)	0.1049 (2)	0.3702 (2)	0.0349 (8)
C37	0.5242 (3)	0.1414 (2)	0.2283 (2)	0.0298 (8)
N31	0.5423 (3)	0.21111 (16)	0.24940 (18)	0.0282 (6)
N41	0.4467 (3)	0.25948 (16)	0.20021 (18)	0.0292 (6)
C47	0.4585 (3)	0.3342 (2)	0.2229 (2)	0.0286 (7)
O47	0.5583 (2)	0.36061 (14)	0.27595 (15)	0.0336 (6)
C41	0.3420 (3)	0.3832 (2)	0.1820 (2)	0.0300 (8)
C42	0.3613 (4)	0.4617 (2)	0.1883 (2)	0.0383 (9)
C43	0.2562 (4)	0.5106 (2)	0.1570 (3)	0.0461 (10)
C44	0.1312 (4)	0.4825 (2)	0.1200 (3)	0.0433 (10)
C45	0.1109 (4)	0.4053 (2)	0.1131 (3)	0.0439 (10)
C46	0.2154 (3)	0.3552 (2)	0.1441 (2)	0.0356 (8)
H13	1.1531	0.2124	0.2772	0.045*
H15	1.2738	0.2742	0.5486	0.045*
H16	1.0607	0.3078	0.5484	0.041*
H17	0.7754	0.3051	0.3552	0.036*
H21	0.6384	0.3498	0.4207	0.032*
H22	0.5206	0.3971	0.6797	0.041*
H23	0.3234	0.4623	0.6653	0.049*
H24	0.1932	0.4950	0.5176	0.046*
H25	0.2605	0.4622	0.3851	0.045*
H26	0.4596	0.3999	0.3987	0.037*
H33	0.7078	−0.0925	0.2853	0.044*
H35	0.8326	0.0666	0.4853	0.047*
H36	0.6929	0.1552	0.3923	0.042*
H37	0.4530	0.1260	0.1781	0.036*
H41	0.3745	0.2418	0.1621	0.035*
H42	0.4469	0.4814	0.2142	0.046*
H43	0.2703	0.5638	0.1610	0.055*
H44	0.0592	0.5162	0.0994	0.052*
H45	0.0250	0.3861	0.0870	0.053*
H46	0.2006	0.3021	0.1395	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.0274 (17)	0.035 (2)	0.0250 (16)	0.0012 (15)	0.0034 (13)	−0.0004 (14)
C12	0.037 (2)	0.042 (2)	0.0278 (18)	0.0082 (17)	0.0027 (15)	−0.0017 (16)
Cl12	0.0516 (6)	0.0989 (10)	0.0353 (5)	0.0291 (6)	−0.0069 (4)	−0.0224 (6)
C13	0.044 (2)	0.042 (2)	0.0285 (18)	0.0037 (17)	0.0144 (16)	−0.0002 (15)
C14	0.0282 (17)	0.0290 (19)	0.040 (2)	−0.0011 (15)	0.0136 (15)	−0.0014 (15)
Cl14	0.0308 (5)	0.0503 (6)	0.0515 (6)	−0.0003 (4)	0.0140 (4)	−0.0079 (4)
C15	0.0288 (19)	0.051 (2)	0.0312 (18)	−0.0039 (17)	0.0031 (15)	−0.0051 (16)
C16	0.0344 (19)	0.041 (2)	0.0276 (17)	−0.0023 (16)	0.0069 (15)	−0.0041 (15)
C17	0.0277 (17)	0.0313 (19)	0.0269 (17)	0.0037 (15)	0.0000 (14)	−0.0016 (14)
N11	0.0212 (13)	0.0323 (16)	0.0274 (14)	0.0037 (12)	0.0028 (11)	0.0031 (12)
N21	0.0213 (13)	0.0320 (16)	0.0250 (14)	0.0067 (12)	0.0015 (11)	0.0008 (12)
C27	0.0238 (16)	0.0250 (18)	0.0316 (18)	−0.0047 (14)	0.0051 (14)	0.0002 (14)
O27	0.0241 (12)	0.0443 (15)	0.0252 (12)	0.0040 (11)	0.0033 (9)	0.0036 (10)
C21	0.0206 (16)	0.0271 (18)	0.0330 (17)	−0.0018 (13)	0.0047 (13)	−0.0004 (14)
C22	0.0272 (18)	0.040 (2)	0.0345 (19)	−0.0001 (16)	0.0068 (15)	−0.0025 (16)
C23	0.0311 (19)	0.044 (2)	0.049 (2)	0.0006 (17)	0.0131 (17)	−0.0094 (18)
C24	0.0252 (18)	0.037 (2)	0.051 (2)	0.0029 (16)	0.0086 (16)	−0.0020 (17)
C25	0.0293 (19)	0.037 (2)	0.042 (2)	0.0051 (16)	0.0036 (16)	0.0031 (17)
C26	0.0266 (17)	0.031 (2)	0.0330 (18)	0.0016 (15)	0.0054 (14)	0.0009 (15)
C31	0.0218 (16)	0.0309 (19)	0.0323 (18)	−0.0019 (14)	0.0079 (13)	0.0016 (14)
C32	0.0254 (17)	0.034 (2)	0.0379 (19)	−0.0045 (15)	0.0118 (15)	−0.0026 (15)
Cl32	0.0376 (5)	0.0474 (6)	0.0522 (6)	−0.0016 (4)	0.0026 (4)	−0.0182 (5)
C33	0.0326 (19)	0.030 (2)	0.051 (2)	−0.0012 (16)	0.0180 (17)	0.0008 (17)
C34	0.036 (2)	0.036 (2)	0.045 (2)	0.0055 (17)	0.0138 (17)	0.0137 (17)
Cl34	0.0626 (7)	0.0435 (6)	0.0636 (7)	0.0166 (5)	0.0102 (5)	0.0225 (5)
C35	0.039 (2)	0.040 (2)	0.0336 (19)	0.0021 (17)	−0.0001 (16)	0.0049 (16)
C36	0.0356 (19)	0.032 (2)	0.0345 (19)	0.0024 (16)	0.0040 (16)	0.0035 (15)
C37	0.0237 (17)	0.039 (2)	0.0267 (17)	−0.0008 (15)	0.0065 (13)	0.0000 (15)
N31	0.0239 (14)	0.0315 (17)	0.0281 (14)	0.0044 (12)	0.0043 (11)	0.0026 (12)
N41	0.0226 (14)	0.0341 (17)	0.0256 (14)	0.0022 (12)	−0.0037 (11)	−0.0008 (12)
C47	0.0283 (18)	0.037 (2)	0.0202 (15)	0.0035 (15)	0.0050 (13)	0.0023 (14)
O47	0.0279 (12)	0.0373 (14)	0.0287 (12)	0.0006 (11)	−0.0056 (10)	−0.0025 (10)
C41	0.0301 (18)	0.034 (2)	0.0236 (16)	0.0050 (15)	0.0033 (14)	−0.0011 (14)
C42	0.037 (2)	0.036 (2)	0.036 (2)	0.0019 (16)	−0.0017 (16)	−0.0049 (16)
C43	0.052 (2)	0.034 (2)	0.046 (2)	0.0134 (19)	0.0010 (19)	−0.0039 (18)
C44	0.040 (2)	0.046 (3)	0.040 (2)	0.0192 (19)	0.0042 (17)	0.0006 (18)
C45	0.0302 (19)	0.054 (3)	0.044 (2)	0.0072 (18)	0.0039 (17)	−0.0017 (19)
C46	0.0302 (18)	0.037 (2)	0.0361 (19)	0.0039 (16)	0.0021 (15)	0.0016 (16)

Geometric parameters (Å, º) top

C11—C12	1.387 (5)	C31—C32	1.391 (5)
C11—C16	1.401 (4)	C31—C36	1.397 (5)
C11—C17	1.459 (5)	C31—C37	1.468 (5)
C12—C13	1.392 (5)	C32—C33	1.382 (5)
C12—Cl12	1.744 (3)	C32—Cl32	1.735 (3)
C13—C14	1.362 (5)	C33—C34	1.372 (5)
C13—H13	0.95	C33—H33	0.95
C14—C15	1.382 (5)	C34—C35	1.383 (5)
C14—Cl14	1.743 (3)	C34—Cl34	1.735 (4)
C15—C16	1.372 (5)	C35—C36	1.391 (5)
C15—H15	0.95	C35—H35	0.95
C16—H16	0.95	C36—H36	0.95
C17—N11	1.273 (4)	C37—N31	1.271 (4)
C17—H17	0.95	C37—H37	0.95
N11—N21	1.386 (4)	N31—N41	1.377 (4)
N21—C27	1.352 (4)	N41—C47	1.360 (4)
N21—H21	0.88	N41—H41	0.88
C27—O27	1.236 (4)	C47—O47	1.230 (4)
C27—C21	1.492 (4)	C47—C41	1.496 (4)
C21—C26	1.384 (4)	C41—C46	1.396 (5)
C21—C22	1.392 (5)	C41—C42	1.398 (5)
C22—C23	1.385 (5)	C42—C43	1.386 (5)
C22—H22	0.95	C42—H42	0.95
C23—C24	1.387 (5)	C43—C44	1.381 (6)
C23—H23	0.95	C43—H43	0.95
C24—C25	1.371 (5)	C44—C45	1.377 (6)
C24—H24	0.95	C44—H44	0.95
C25—C26	1.384 (5)	C45—C46	1.394 (5)
C25—H25	0.95	C45—H45	0.95
C26—H26	0.95	C46—H46	0.95

C12—C11—C16	116.7 (3)	C32—C31—C36	117.3 (3)
C12—C11—C17	122.1 (3)	C32—C31—C37	122.9 (3)
C16—C11—C17	121.2 (3)	C36—C31—C37	119.8 (3)
C11—C12—C13	123.0 (3)	C33—C32—C31	122.1 (3)
C11—C12—Cl12	119.1 (3)	C33—C32—Cl32	117.4 (3)
C13—C12—Cl12	117.9 (3)	C31—C32—Cl32	120.5 (3)
C14—C13—C12	117.6 (3)	C34—C33—C32	118.8 (3)
C14—C13—H13	121.2	C34—C33—H33	120.6
C12—C13—H13	121.2	C32—C33—H33	120.6
C13—C14—C15	122.0 (3)	C33—C34—C35	121.6 (3)
C13—C14—Cl14	118.6 (3)	C33—C34—Cl34	118.7 (3)
C15—C14—Cl14	119.4 (3)	C35—C34—Cl34	119.6 (3)
C16—C15—C14	119.3 (3)	C34—C35—C36	118.5 (3)
C16—C15—H15	120.3	C34—C35—H35	120.7
C14—C15—H15	120.3	C36—C35—H35	120.7
C15—C16—C11	121.3 (3)	C35—C36—C31	121.6 (3)
C15—C16—H16	119.3	C35—C36—H36	119.2
C11—C16—H16	119.3	C31—C36—H36	119.2
N11—C17—C11	120.6 (3)	N31—C37—C31	118.9 (3)
N11—C17—H17	119.7	N31—C37—H37	120.6
C11—C17—H17	119.7	C31—C37—H37	120.6
C17—N11—N21	114.2 (3)	C37—N31—N41	115.3 (3)
C27—N21—N11	118.5 (2)	C47—N41—N31	117.6 (3)
C27—N21—H21	124.9	C47—N41—H41	120.9
N11—N21—H21	115.7	N31—N41—H41	120.9
O27—C27—N21	121.4 (3)	O47—C47—N41	122.3 (3)
O27—C27—C21	122.1 (3)	O47—C47—C41	121.1 (3)
N21—C27—C21	116.5 (3)	N41—C47—C41	116.6 (3)
C26—C21—C22	119.1 (3)	C46—C41—C42	119.0 (3)
C26—C21—C27	123.9 (3)	C46—C41—C47	123.8 (3)
C22—C21—C27	116.9 (3)	C42—C41—C47	117.1 (3)
C23—C22—C21	120.0 (3)	C43—C42—C41	120.3 (3)
C23—C22—H22	120.0	C43—C42—H42	119.8
C21—C22—H22	120.0	C41—C42—H42	119.8
C22—C23—C24	120.3 (4)	C44—C43—C42	120.3 (4)
C22—C23—H23	119.9	C44—C43—H43	119.8
C24—C23—H23	119.9	C42—C43—H43	119.8
C25—C24—C23	119.6 (3)	C45—C44—C43	119.9 (3)
C25—C24—H24	120.2	C45—C44—H44	120.0
C23—C24—H24	120.2	C43—C44—H44	120.1
C24—C25—C26	120.4 (3)	C44—C45—C46	120.6 (4)
C24—C25—H25	119.8	C44—C45—H45	119.7
C26—C25—H25	119.8	C46—C45—H45	119.7
C25—C26—C21	120.5 (3)	C45—C46—C41	119.9 (4)
C25—C26—H26	119.8	C45—C46—H46	120.1
C21—C26—H26	119.8	C41—C46—H46	120.1

C16—C11—C12—C13	3.8 (6)	C36—C31—C32—C33	−1.7 (5)
C17—C11—C12—C13	−179.3 (4)	C37—C31—C32—C33	−177.9 (3)
C16—C11—C12—Cl12	−177.0 (3)	C36—C31—C32—Cl32	178.7 (3)
C17—C11—C12—Cl12	−0.1 (5)	C37—C31—C32—Cl32	2.5 (5)
C11—C12—C13—C14	−2.4 (6)	C31—C32—C33—C34	1.4 (5)
Cl12—C12—C13—C14	178.3 (3)	Cl32—C32—C33—C34	−179.0 (3)
C12—C13—C14—C15	0.0 (6)	C32—C33—C34—C35	−0.1 (6)
C12—C13—C14—Cl14	178.5 (3)	C32—C33—C34—Cl34	178.4 (3)
C13—C14—C15—C16	0.9 (6)	C33—C34—C35—C36	−0.7 (6)
Cl14—C14—C15—C16	−177.6 (3)	Cl34—C34—C35—C36	−179.2 (3)
C14—C15—C16—C11	0.6 (6)	C34—C35—C36—C31	0.3 (6)
C12—C11—C16—C15	−2.8 (5)	C32—C31—C36—C35	0.9 (5)
C17—C11—C16—C15	−179.7 (3)	C37—C31—C36—C35	177.2 (3)
C12—C11—C17—N11	168.6 (4)	C32—C31—C37—N31	−166.3 (3)
C16—C11—C17—N11	−14.6 (5)	C36—C31—C37—N31	17.7 (5)
C11—C17—N11—N21	175.3 (3)	C31—C37—N31—N41	−174.9 (3)
C17—N11—N21—C27	−179.4 (3)	C37—N31—N41—C47	177.3 (3)
N11—N21—C27—O27	−8.1 (5)	N31—N41—C47—O47	9.6 (5)
N11—N21—C27—C21	170.4 (3)	N31—N41—C47—C41	−168.8 (3)
O27—C27—C21—C26	178.6 (3)	O47—C47—C41—C46	−161.1 (3)
N21—C27—C21—C26	0.0 (5)	N41—C47—C41—C46	17.3 (5)
O27—C27—C21—C22	2.0 (5)	O47—C47—C41—C42	14.6 (5)
N21—C27—C21—C22	−176.6 (3)	N41—C47—C41—C42	−167.0 (3)
C26—C21—C22—C23	0.7 (5)	C46—C41—C42—C43	−0.2 (5)
C27—C21—C22—C23	177.5 (3)	C47—C41—C42—C43	−176.1 (3)
C21—C22—C23—C24	0.1 (6)	C41—C42—C43—C44	0.6 (6)
C22—C23—C24—C25	−0.1 (6)	C42—C43—C44—C45	−0.8 (6)
C23—C24—C25—C26	−0.8 (6)	C43—C44—C45—C46	0.7 (6)
C24—C25—C26—C21	1.6 (6)	C44—C45—C46—C41	−0.4 (6)
C22—C21—C26—C25	−1.5 (5)	C42—C41—C46—C45	0.1 (5)
C27—C21—C26—C25	−178.1 (3)	C47—C41—C46—C45	175.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···O47	0.88	2.10	2.969 (3)	168
N41—H41···O27ⁱ	0.88	2.20	2.989 (4)	150
C13—H13···O27ⁱⁱ	0.95	2.47	3.425 (4)	179
C17—H17···O47	0.95	2.49	3.311 (4)	145
C26—H26···O47	0.95	2.41	3.354 (4)	171
C37—H37···O27ⁱ	0.95	2.59	3.300 (4)	131
C46—H46···O27ⁱ	0.95	2.44	3.381 (4)	170
C35—H35···Cg2ⁱⁱⁱ	0.95	2.88	3.480 (5)	122

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

Experimental details

	(I)	(II)
Crystal data
Chemical formula	C₁₄H₁₀F₂N₂O	C₁₄H₁₀Cl₂N₂O
M_r	260.24	293.14
Crystal system, space group	Monoclinic, P2₁/n	Monoclinic, P2₁/n
Temperature (K)	120	120
a, b, c (Å)	10.1310 (3), 17.2172 (6), 14.4288 (5)	10.5093 (5), 17.6499 (9), 14.7982 (5)
β (°)	103.957 (2)	104.732 (2)
V (Å³)	2442.48 (14)	2654.7 (2)
Z	8	8
Radiation type	Mo Kα	Mo Kα
µ (mm⁻¹)	0.11	0.48
Crystal size (mm)	0.36 × 0.11 × 0.03	0.12 × 0.03 × 0.03

Data collection
Diffractometer	Bruker Nonius KappaCCD area-detector diffractometer	Bruker Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.973, 0.997	0.964, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	26932, 5577, 3589	38980, 6060, 3687
R_int	0.080	0.102
(sin θ/λ)_max (Å⁻¹)	0.649	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.130, 1.04	0.061, 0.155, 1.04
No. of reflections	5577	6060
No. of parameters	343	343
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.29	0.53, −0.70

Computer programs: COLLECT (Nonius, 1999), DENZO (Otwinowski & Minor, 1997) and COLLECT, DENZO and COLLECT, OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997), OSCAIL and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Hydrogen-bond geometry (Å, º) for (I) top

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···O47	0.88	2.02	2.889 (2)	170
N41—H41···O27ⁱ	0.88	2.12	2.916 (2)	150
C13—H13···O27ⁱⁱ	0.95	2.37	3.286 (3)	162
C17—H17···O47	0.95	2.47	3.277 (2)	143
C26—H26···O47	0.95	2.41	3.340 (3)	167
C37—H37···O27ⁱ	0.95	2.50	3.251 (2)	136
C46—H46···O27ⁱ	0.95	2.47	3.402 (2)	165
C23—H23···Cg1ⁱⁱⁱ	0.95	2.91	3.859 (3)	174

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

Hydrogen-bond geometry (Å, º) for (II) top

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···O47	0.88	2.10	2.969 (3)	168
N41—H41···O27ⁱ	0.88	2.20	2.989 (4)	150
C13—H13···O27ⁱⁱ	0.95	2.47	3.425 (4)	179
C17—H17···O47	0.95	2.49	3.311 (4)	145
C26—H26···O47	0.95	2.41	3.354 (4)	171
C37—H37···O27ⁱ	0.95	2.59	3.300 (4)	131
C46—H46···O27ⁱ	0.95	2.44	3.381 (4)	170
C35—H35···Cg2ⁱⁱⁱ	0.95	2.88	3.480 (5)	122

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

Selected torsion angles (°) for compounds (I) and (II) top

Parameter	(I)		(II)
	x = 1, y = 2	x = 3, y = 4	x = 1, y = 2	x = 3, y = 4
Cx1-Cx7-Nx1-Ny1	177.66 (16)	-177.09 (17)	175.3 (3)	-174.9 (3)
Cx7-Nx1-Ny1-Cy7	-177.33 (17)	179.69 (19)	-179.4 (3)	177.3 (3)
Nx1-Ny1-Ny7-Cy1	172.31 (16)	-173.40 (17)	170.4 (3)	-168.8 (3)
Cx2-Cx1-Cx7-Nx1	176.80 (19)	-171.9 (2)	168.6 (4)	-166.3 (3)
Cn2-Cy1-Cy7-Ny1	177.65 (17)	-175.2 (2)	-176.6 (3)	-167.0 (3)

Acknowledgements

The X-ray data were collected at the EPSRC X-ray Crystallographic Service, University of Southampton; the authors thank the staff of the Service for all their help and advice. JLW thanks CNPq and FAPERJ for financial support.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada. Google Scholar
Jing, Z.-L., Wang, X.-Y., Chen, X. & Deng, Q.-L. (2005). Acta Cryst. E61, o4316–o4317. Web of Science CSD CrossRef IUCr Journals Google Scholar
McArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland. Google Scholar
Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2053-2296

Volume 62| Part 3| March 2006| Pages o118-o121

doi:10.1107/S0108270106001995

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2,4-Di­fluoro­benzaldehyde benzoyl­hydrazone and 2,4-di­chloro­benz­aldehyde benzoyl­hydrazone are isostructural at 120 K with Z′ = 2: complex sheets built from N—H⋯O, C—H⋯O and C—H⋯π(arene) hydrogen bonds

Comment

Experimental

Compound (I)

Crystal data

Data collection

Refinement

Compound (II)

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,4-Difluorobenzaldehyde benzoylhydrazone and 2,4-dichlorobenzaldehyde benzoylhydrazone are isostructural at 120 K with Z′ = 2: complex sheets built from N—H⋯O, C—H⋯O and C—H⋯π(arene) hydrogen bonds