3-Hydr­oxy-N′-[(Z)-(5-methyl-2-fur­yl)methyl­idene]naphthalene-2-carbo­hydrazide

Shafiq, Z.; Yaqub, M.; Tahir, M.N.; Nawaz, M.H.; Iqbal, M.S.

doi:10.1107/S1600536809043141

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Pages o2845-o2846

https://doi.org/10.1107/S1600536809043141

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3-Hydroxy-N′-[(Z)-(5-methyl-2-furyl)methylidene]naphthalene-2-carbohydrazide

Zahid Shafiq,^a Muhammad Yaqub,^a M. Nawaz Tahir,^b ^* Mian Hasnain Nawaz ^a and M. Saeed Iqbal ^c

^aDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan, ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^cDepartment of Chemistry, Government College University, Lahore, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 19 October 2009; accepted 20 October 2009; online 23 October 2009)

The asymmetric unit of title compound, C₁₇H₁₄N₂O₃, contains three independent molecules. In one of these molecules, the 5-methyl-2-furyl group is disordered over two sets of sites with an occupancy ratio of 0.747 (3):0.253 (3). In the two ordered molecules, the furan and naphthalene rings are oriented at dihedral angles of 11.05 (12) and 32.2 (5)°. In the disordered molecule, the furan rings with major and minor occupancies are oriented at dihedral angles of 41.4 (2) and 26.6 (13)°, respectively, with the corresponding naphthalene ring. An intramolecular O—H⋯O hydrogen bond occurs within each molecule. In the crystal, molecules are linked by N—H⋯O, N—H⋯(N,O) and C—H⋯O interactions.

Related literature

For related structures, see: Bai & Jing (2007 ); Huang (2009 ); Liu & Li (2004 ); Shafiq et al. (2009a ,b ); Yao & Jing (2007 ). For graph-set motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₇H₁₄N₂O₃
M_r = 294.30
Triclinic, $[P \overline 1]$
a = 10.604 (4) Å
b = 12.321 (5) Å
c = 18.615 (3) Å
α = 71.351 (5)°
β = 73.742 (4)°
γ = 84.280 (5)°
V = 2212.1 (13) Å³
Z = 6
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.25 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.975, T_max = 0.985
48594 measured reflections
11199 independent reflections
5268 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.130
S = 0.99
11199 reflections
624 parameters
7 restraints
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O8ⁱ	0.86	2.15	2.869 (2)	142
N4—H4N⋯O2	0.86	2.20	2.896 (2)	137
N6—H6N⋯O5ⁱⁱ	0.86	2.36	3.074 (2)	140
N6—H6N⋯N3ⁱⁱ	0.86	2.44	3.212 (2)	149
O3—H3O⋯O2	0.82	1.89	2.612 (3)	145
O6—H6O⋯O5	0.82	1.89	2.603 (2)	145
O9—H9O⋯O8	0.82	1.86	2.588 (2)	147
C34—H34⋯O2	0.93	2.48	3.398 (3)	167
C40—H40⋯O5ⁱⁱ	0.93	2.42	3.185 (3)	140
C44—H44⋯O1A	0.93	2.59	3.514 (5)	176
C48—H48⋯O3ⁱⁱ	0.93	2.51	3.149 (3)	126
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809043141/hb5157sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809043141/hb5157Isup2.hkl

checkCIF report

Comment top

In continuation to the formation of different hydrazide derivatives (Shafiq et al., 2009a, 2009b), the title compound (I, Fig. 1), has been prepared and being reported.

The crystal structures of (II) 2-Hydroxyacetophenone 3-hydroxy-2-naphthoylhydrazone (Liu & Li, 2004), (III) N'-[4-(Dimethylamino)benzylidene]-3-hydroxy-2-naphthohydrazide (Huang, 2009), (IV) (E)-N'-((5-Methylfuran-2-yl)methylene)furan-2-carbohydrazide (Yao & Jing, 2007) and (V) (E)-4-Bromo-N'-((5-methylfuran-2-yl)methylene)benzohydrazide (Bai & Jing, 2007) have been published which contain both of the moieties involved in (I).

There are three molecules of (I) in the asymmetric unit of title compound. All differ from one another. This difference is observed from the dihedral angles between the rings and also from disorder. In the disordered molecule the furan and naphthalene group A (C1A–C4A/O1A) and B (C8–C17), respectively are oriented at a dihedral angle of 41.4 (2)°. In the molecule containing O4, the groups C (C18–C22/O4) and D (C25–C34) make a dihedral angle of 32.2 (5)°. Similarly in the remaining molecule, the groups E (C35–C38/O7) and F (C42–C51) are oriented at a dihedral angle of 11.05 (12)°. The dihedral angle between the disordered rings [A (C1A–C4A/O1A) and G (C1B–C4B/O1B)] of furan is 15 (2)°. The molecules are stabilized in the form of infinite one dimensional polymeric chains extending along the crystallographic b axis and also there exists various ring motifs (Fig. 2) (Bernstein et al., 1995).

Related literature top

For related structures, see: Bai & Jing (2007); Huang (2009); Liu & Li (2004); Shafiq et al. (2009a,b); Yao & Jing (2007). For graph-set motifs, see: Bernstein et al. (1995).

Experimental top

To a hot stirred solution of 3-hydroxy-2-naphthoichydrazide (1.5 g, 7.4 mmol) in ethanol (35 ml) and 1,4-dioxan (2 ml) was added 5-methylfurfural (0.736 ml, 7.4 mmol). The resultant mixture was then heated under reflux. After 30 minutes solid product began to form. The reaction mixture was refluxed about 1.5 h for the sake of completion of reaction which was monitored through TLC. The mixture was cooled to room temperature and the solid was collected by suction filtration. The precipitates were washed with 1,4-dioxan, filtered and dried. Yellow prisms of (I) were obtained by recrystallization of the crude product in 1,4-dioxan after five days.

Structure description top

In continuation to the formation of different hydrazide derivatives (Shafiq et al., 2009a, 2009b), the title compound (I, Fig. 1), has been prepared and being reported.

For related structures, see: Bai & Jing (2007); Huang (2009); Liu & Li (2004); Shafiq et al. (2009a,b); Yao & Jing (2007). For graph-set motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of (I) with the atom numbering scheme for atoms of greater occupancy. The displacement ellipsoids are drawn at the 30% probability level. H-atoms are shown by small circles of arbitrary radii.
	Fig. 2. View of (I) with the atom numbering scheme for atoms of smaller occupancy ratio. The displacement ellipsoids are drawn at the 30% probability level. H-atoms are shown by small circles of arbitrary radii.
	Fig. 3. The partial packing for (I), which shows that molecules form polymeric chains and have different ring motifs. H-atoms not involved in H-bondings have been omitted for clarity.

3-Hydroxy-N'-[(Z)-(5-methyl-2-furyl)methylidene]naphthalene- 2-carbohydrazide top

Crystal data top

C₁₇H₁₄N₂O₃	Z = 6
M_r = 294.30	F(000) = 924
Triclinic, P1	D_x = 1.326 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.604 (4) Å	Cell parameters from 5268 reflections
b = 12.321 (5) Å	θ = 2.4–28.7°
c = 18.615 (3) Å	µ = 0.09 mm⁻¹
α = 71.351 (5)°	T = 296 K
β = 73.742 (4)°	Prisms, yellow
γ = 84.280 (5)°	0.25 × 0.20 × 0.18 mm
V = 2212.1 (13) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	11199 independent reflections
Radiation source: fine-focus sealed tube	5268 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
Detector resolution: 7.40 pixels mm^-1	θ_max = 28.7°, θ_min = 2.4°
ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −16→16
T_min = 0.975, T_max = 0.985	l = −24→24
48594 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0516P)² + 0.1613P] where P = (F_o² + 2F_c²)/3
11199 reflections	(Δ/σ)_max = 0.001
624 parameters	Δρ_max = 0.16 e Å⁻³
7 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₇H₁₄N₂O₃	γ = 84.280 (5)°
M_r = 294.30	V = 2212.1 (13) Å³
Triclinic, P1	Z = 6
a = 10.604 (4) Å	Mo Kα radiation
b = 12.321 (5) Å	µ = 0.09 mm⁻¹
c = 18.615 (3) Å	T = 296 K
α = 71.351 (5)°	0.25 × 0.20 × 0.18 mm
β = 73.742 (4)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	11199 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	5268 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.985	R_int = 0.044
48594 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	7 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 0.99	Δρ_max = 0.16 e Å⁻³
11199 reflections	Δρ_min = −0.16 e Å⁻³
624 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1A	0.9959 (4)	0.1541 (3)	0.4542 (3)	0.0562 (9)	0.747 (3)
O2	0.65580 (14)	0.43845 (9)	0.24178 (8)	0.0631 (5)
O3	0.47122 (17)	0.46866 (13)	0.16900 (11)	0.0921 (7)
N1	0.80165 (15)	0.29221 (12)	0.32581 (9)	0.0531 (6)
N2	0.73255 (15)	0.25872 (12)	0.28429 (8)	0.0510 (5)
C1A	0.9445 (6)	0.2436 (3)	0.4053 (3)	0.0483 (11)	0.747 (3)
C2A	0.9913 (5)	0.3407 (4)	0.4028 (3)	0.0636 (16)	0.747 (3)
C3A	1.0743 (4)	0.3126 (4)	0.4533 (4)	0.0673 (16)	0.747 (3)
C4A	1.0758 (8)	0.1983 (6)	0.4837 (4)	0.0562 (11)	0.747 (3)
C5A	1.1352 (3)	0.1156 (3)	0.54123 (18)	0.0815 (12)	0.747 (3)
C6	0.86051 (19)	0.21126 (16)	0.36670 (11)	0.0541 (7)
C7	0.66876 (18)	0.33839 (14)	0.23901 (10)	0.0476 (6)
C8	0.61847 (17)	0.30478 (13)	0.18306 (10)	0.0454 (6)
C9	0.52377 (19)	0.37537 (15)	0.14756 (12)	0.0569 (7)
C10	0.4845 (2)	0.35028 (16)	0.09087 (12)	0.0631 (8)
C11	0.53739 (18)	0.25684 (15)	0.06467 (11)	0.0540 (7)
C12	0.5025 (2)	0.23053 (19)	0.00403 (12)	0.0708 (8)
C13	0.5589 (3)	0.1406 (2)	−0.02024 (13)	0.0818 (10)
C14	0.6522 (3)	0.07105 (19)	0.01321 (13)	0.0792 (10)
C15	0.6889 (2)	0.09305 (16)	0.07126 (12)	0.0636 (8)
C16	0.63285 (18)	0.18610 (14)	0.09851 (10)	0.0472 (6)
C17	0.67088 (17)	0.21241 (13)	0.15727 (10)	0.0469 (6)
C1B	0.947 (3)	0.2146 (16)	0.4118 (16)	0.086 (3)	0.253 (3)
C2B	1.014 (3)	0.141 (2)	0.4568 (17)	0.086 (3)	0.253 (3)
C3B	1.071 (3)	0.205 (2)	0.4924 (18)	0.086 (3)	0.253 (3)
C4B	1.035 (2)	0.3134 (17)	0.4682 (16)	0.086 (3)	0.253 (3)
C5B	1.0541 (8)	0.4178 (3)	0.4832 (5)	0.086 (3)	0.253 (3)
O1B	0.9529 (14)	0.3203 (12)	0.4215 (9)	0.086 (3)	0.253 (3)
O4	0.65494 (13)	0.67372 (10)	0.43795 (7)	0.0614 (5)
O5	0.84414 (14)	0.82850 (10)	0.14400 (8)	0.0702 (5)
O6	0.95849 (17)	0.89165 (10)	−0.00598 (9)	0.0790 (6)
N3	0.76595 (14)	0.66539 (12)	0.28104 (9)	0.0485 (5)
N4	0.80070 (15)	0.64348 (11)	0.20930 (9)	0.0515 (6)
C18	0.69926 (19)	0.57430 (15)	0.42005 (12)	0.0550 (7)
C19	0.6813 (2)	0.48682 (18)	0.48745 (13)	0.0751 (9)
C20	0.6243 (2)	0.5319 (2)	0.54963 (13)	0.0788 (9)
C21	0.6085 (2)	0.6441 (2)	0.51818 (13)	0.0687 (9)
C22	0.5512 (3)	0.7378 (2)	0.55129 (15)	0.1067 (11)
C23	0.74565 (19)	0.57470 (15)	0.34036 (12)	0.0554 (7)
C24	0.83427 (17)	0.73040 (14)	0.14223 (11)	0.0474 (6)
C25	0.85989 (16)	0.70440 (13)	0.06697 (10)	0.0442 (6)
C26	0.92304 (18)	0.78819 (14)	−0.00429 (12)	0.0527 (7)
C27	0.95030 (19)	0.76484 (15)	−0.07400 (12)	0.0586 (7)
C28	0.91602 (18)	0.66060 (15)	−0.07890 (11)	0.0510 (7)
C29	0.9420 (2)	0.63507 (18)	−0.15087 (12)	0.0663 (8)
C30	0.9066 (2)	0.53385 (19)	−0.15254 (13)	0.0698 (9)
C31	0.8445 (2)	0.45044 (18)	−0.08347 (13)	0.0650 (8)
C32	0.81850 (19)	0.47160 (15)	−0.01349 (11)	0.0548 (7)
C33	0.85240 (17)	0.57673 (14)	−0.00917 (10)	0.0446 (6)
C34	0.82635 (17)	0.60206 (14)	0.06213 (10)	0.0461 (6)
O7	−0.09686 (12)	−0.07040 (10)	0.73469 (7)	0.0568 (5)
O8	0.38574 (13)	−0.03678 (10)	0.64992 (8)	0.0619 (5)
O9	0.61823 (14)	0.03617 (13)	0.56670 (9)	0.0758 (6)
N5	0.14612 (15)	0.01505 (11)	0.72496 (9)	0.0499 (5)
N6	0.25674 (15)	0.07340 (11)	0.71746 (9)	0.0505 (5)
C35	−0.08637 (19)	0.00704 (14)	0.77153 (11)	0.0508 (7)
C36	−0.2056 (2)	0.02625 (17)	0.81559 (12)	0.0652 (8)
C37	−0.2954 (2)	−0.04267 (18)	0.80687 (13)	0.0693 (8)
C38	−0.2277 (2)	−0.09876 (17)	0.75726 (13)	0.0616 (8)
C39	−0.2644 (2)	−0.1778 (2)	0.72150 (15)	0.0864 (10)
C40	0.0380 (2)	0.05329 (15)	0.76010 (11)	0.0515 (7)
C41	0.37427 (18)	0.04222 (13)	0.67934 (10)	0.0453 (6)
C42	0.48957 (17)	0.10614 (13)	0.67331 (10)	0.0439 (6)
C43	0.60845 (19)	0.09994 (14)	0.61589 (11)	0.0527 (7)
C44	0.7161 (2)	0.15844 (16)	0.60846 (11)	0.0598 (7)
C45	0.71458 (19)	0.22425 (14)	0.65804 (11)	0.0533 (7)
C46	0.8259 (2)	0.28335 (17)	0.65383 (13)	0.0716 (8)
C47	0.8210 (2)	0.34244 (17)	0.70435 (15)	0.0785 (10)
C48	0.7061 (2)	0.34898 (17)	0.76139 (14)	0.0731 (9)
C49	0.5965 (2)	0.29390 (15)	0.76774 (12)	0.0604 (7)
C50	0.59774 (18)	0.22941 (13)	0.71683 (11)	0.0477 (6)
C51	0.48799 (18)	0.16903 (13)	0.72286 (10)	0.0462 (6)
H5B	1.19660	0.06780	0.51596	0.1222*	0.747 (3)
H5C	1.06783	0.06904	0.58243	0.1222*	0.747 (3)
H10	0.42122	0.39635	0.06919	0.0758*
H12	0.44027	0.27554	−0.01927	0.0849*
H13	0.53485	0.12481	−0.06021	0.0980*
H14	0.68945	0.00942	−0.00428	0.0950*
H15	0.75147	0.04645	0.09333	0.0764*
H17	0.73341	0.16619	0.17963	0.0563*
H6	0.84985	0.13503	0.37147	0.0649*
H2A	0.97261	0.41395	0.37319	0.0759*	0.747 (3)
H2N	0.73033	0.18777	0.28734	0.0613*
H3A	1.11989	0.36398	0.46372	0.0806*	0.747 (3)
H3O	0.50968	0.47994	0.19848	0.1381*
H5A	1.18023	0.15569	0.56310	0.1222*	0.747 (3)
H2B	1.02185	0.06276	0.46423	0.1030*	0.253 (3)
H3B	1.12456	0.17477	0.52635	0.1030*	0.253 (3)
H5D	1.11452	0.46593	0.43825	0.1288*	0.253 (3)
H5E	1.08878	0.39962	0.52817	0.1288*	0.253 (3)
H5F	0.97134	0.45720	0.49329	0.1288*	0.253 (3)
H4N	0.80073	0.57443	0.20780	0.0618*
H6O	0.94124	0.89522	0.03899	0.1186*
H19	0.70270	0.41031	0.49193	0.0901*
H20	0.60183	0.49106	0.60287	0.0945*
H22A	0.52675	0.70863	0.60763	0.1597*
H22B	0.47479	0.76850	0.53326	0.1597*
H22C	0.61476	0.79722	0.53448	0.1597*
H23	0.76231	0.50436	0.33077	0.0664*
H27	0.99298	0.81971	−0.11979	0.0703*
H29	0.98405	0.68880	−0.19749	0.0795*
H30	0.92372	0.51929	−0.20043	0.0838*
H31	0.82121	0.38089	−0.08550	0.0780*
H32	0.77766	0.41586	0.03235	0.0658*
H34	0.78453	0.54724	0.10822	0.0553*
H6N	0.24982	0.12886	0.73705	0.0606*
H9O	0.54982	0.00109	0.57882	0.1136*
H36	−0.22506	0.07566	0.84606	0.0782*
H37	−0.38499	−0.04805	0.83116	0.0831*
H39A	−0.35821	−0.18535	0.73688	0.1295*
H39B	−0.22443	−0.25144	0.73904	0.1295*
H39C	−0.23452	−0.14793	0.66530	0.1295*
H40	0.04078	0.11405	0.77906	0.0618*
H44	0.79238	0.15481	0.56965	0.0717*
H46	0.90363	0.28132	0.61559	0.0859*
H47	0.89576	0.37939	0.70093	0.0940*
H48	0.70407	0.39100	0.79526	0.0877*
H49	0.51989	0.29873	0.80603	0.0724*
H51	0.41136	0.17154	0.76172	0.0554*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.062 (2)	0.0574 (15)	0.0452 (13)	−0.0028 (14)	−0.0083 (13)	−0.0145 (12)
O2	0.0890 (10)	0.0427 (7)	0.0647 (9)	−0.0060 (6)	−0.0230 (8)	−0.0220 (6)
O3	0.1054 (13)	0.0801 (10)	0.1190 (14)	0.0425 (9)	−0.0531 (11)	−0.0613 (10)
N1	0.0606 (10)	0.0534 (9)	0.0515 (10)	−0.0088 (8)	−0.0150 (9)	−0.0219 (8)
N2	0.0667 (10)	0.0432 (8)	0.0508 (10)	−0.0109 (7)	−0.0196 (8)	−0.0180 (7)
C1A	0.0464 (18)	0.057 (2)	0.0424 (18)	0.0036 (18)	−0.0095 (14)	−0.0197 (19)
C2A	0.071 (3)	0.059 (2)	0.074 (3)	0.0093 (19)	−0.039 (3)	−0.024 (2)
C3A	0.073 (3)	0.066 (2)	0.076 (3)	0.004 (2)	−0.035 (3)	−0.0274 (19)
C4A	0.0472 (19)	0.075 (2)	0.047 (2)	0.0022 (16)	−0.0127 (18)	−0.0199 (18)
C5A	0.083 (2)	0.095 (2)	0.064 (2)	0.0103 (18)	−0.0319 (18)	−0.0133 (18)
C6	0.0601 (13)	0.0591 (11)	0.0469 (12)	−0.0063 (10)	−0.0103 (10)	−0.0230 (10)
C7	0.0553 (12)	0.0408 (9)	0.0439 (11)	−0.0110 (8)	−0.0042 (9)	−0.0136 (8)
C8	0.0510 (11)	0.0414 (9)	0.0422 (11)	−0.0067 (8)	−0.0070 (9)	−0.0132 (8)
C9	0.0569 (13)	0.0492 (10)	0.0654 (14)	0.0074 (9)	−0.0131 (11)	−0.0237 (10)
C10	0.0599 (13)	0.0643 (12)	0.0713 (15)	0.0098 (10)	−0.0285 (12)	−0.0224 (11)
C11	0.0554 (12)	0.0556 (10)	0.0511 (12)	−0.0067 (9)	−0.0145 (10)	−0.0143 (9)
C12	0.0808 (16)	0.0804 (14)	0.0614 (14)	−0.0020 (12)	−0.0337 (12)	−0.0224 (12)
C13	0.109 (2)	0.0920 (16)	0.0615 (15)	−0.0052 (15)	−0.0349 (15)	−0.0346 (13)
C14	0.1039 (19)	0.0793 (15)	0.0710 (16)	0.0092 (14)	−0.0291 (15)	−0.0432 (13)
C15	0.0791 (15)	0.0613 (11)	0.0597 (14)	0.0085 (10)	−0.0227 (12)	−0.0299 (10)
C16	0.0510 (12)	0.0468 (9)	0.0431 (11)	−0.0055 (8)	−0.0102 (9)	−0.0134 (8)
C17	0.0526 (12)	0.0421 (9)	0.0461 (11)	−0.0031 (8)	−0.0133 (9)	−0.0124 (8)
C1B	0.095 (5)	0.092 (4)	0.096 (5)	0.001 (3)	−0.040 (4)	−0.049 (4)
C2B	0.095 (5)	0.092 (4)	0.096 (5)	0.001 (3)	−0.040 (4)	−0.049 (4)
C3B	0.095 (5)	0.092 (4)	0.096 (5)	0.001 (3)	−0.040 (4)	−0.049 (4)
C4B	0.095 (5)	0.092 (4)	0.096 (5)	0.001 (3)	−0.040 (4)	−0.049 (4)
C5B	0.095 (5)	0.092 (4)	0.096 (5)	0.001 (3)	−0.040 (4)	−0.049 (4)
O1B	0.095 (5)	0.092 (4)	0.096 (5)	0.001 (3)	−0.040 (4)	−0.049 (4)
O4	0.0708 (9)	0.0619 (8)	0.0501 (9)	0.0040 (7)	−0.0119 (7)	−0.0201 (7)
O5	0.0981 (11)	0.0463 (7)	0.0701 (10)	−0.0098 (7)	−0.0129 (8)	−0.0283 (7)
O6	0.1093 (12)	0.0463 (7)	0.0755 (10)	−0.0209 (7)	−0.0129 (10)	−0.0145 (7)
N3	0.0586 (10)	0.0450 (8)	0.0495 (10)	0.0013 (7)	−0.0179 (8)	−0.0221 (8)
N4	0.0728 (11)	0.0406 (8)	0.0486 (10)	0.0017 (7)	−0.0177 (8)	−0.0232 (8)
C18	0.0678 (14)	0.0488 (10)	0.0531 (13)	−0.0021 (9)	−0.0245 (11)	−0.0140 (10)
C19	0.1016 (19)	0.0621 (13)	0.0624 (15)	−0.0051 (12)	−0.0329 (14)	−0.0090 (12)
C20	0.0849 (17)	0.0909 (17)	0.0506 (14)	−0.0115 (14)	−0.0202 (13)	−0.0028 (13)
C21	0.0616 (14)	0.0959 (17)	0.0458 (14)	−0.0006 (12)	−0.0091 (11)	−0.0224 (12)
C22	0.109 (2)	0.133 (2)	0.0724 (17)	0.0223 (18)	0.0000 (16)	−0.0515 (17)
C23	0.0738 (14)	0.0473 (10)	0.0560 (13)	0.0033 (9)	−0.0280 (11)	−0.0224 (10)
C24	0.0484 (11)	0.0426 (9)	0.0566 (12)	0.0022 (8)	−0.0160 (9)	−0.0214 (9)
C25	0.0449 (11)	0.0400 (9)	0.0487 (11)	0.0030 (8)	−0.0137 (9)	−0.0147 (8)
C26	0.0566 (12)	0.0407 (9)	0.0578 (13)	0.0002 (8)	−0.0142 (10)	−0.0120 (9)
C27	0.0638 (14)	0.0494 (10)	0.0489 (13)	−0.0021 (9)	−0.0083 (10)	−0.0018 (9)
C28	0.0512 (12)	0.0539 (10)	0.0460 (12)	0.0078 (9)	−0.0147 (10)	−0.0137 (9)
C29	0.0742 (15)	0.0729 (14)	0.0434 (13)	0.0049 (11)	−0.0108 (11)	−0.0123 (10)
C30	0.0820 (16)	0.0849 (15)	0.0491 (14)	0.0121 (13)	−0.0179 (12)	−0.0326 (12)
C31	0.0743 (15)	0.0703 (13)	0.0625 (15)	0.0044 (11)	−0.0229 (12)	−0.0341 (12)
C32	0.0632 (13)	0.0554 (10)	0.0490 (12)	−0.0049 (9)	−0.0131 (10)	−0.0204 (9)
C33	0.0430 (11)	0.0478 (9)	0.0423 (11)	0.0023 (8)	−0.0115 (9)	−0.0136 (9)
C34	0.0503 (11)	0.0440 (9)	0.0415 (11)	−0.0043 (8)	−0.0090 (9)	−0.0112 (8)
O7	0.0468 (8)	0.0645 (8)	0.0599 (9)	−0.0066 (6)	−0.0104 (7)	−0.0213 (7)
O8	0.0701 (9)	0.0503 (7)	0.0711 (9)	−0.0062 (6)	−0.0075 (7)	−0.0344 (7)
O9	0.0750 (10)	0.0908 (10)	0.0713 (10)	−0.0099 (8)	0.0016 (8)	−0.0534 (9)
N5	0.0502 (10)	0.0474 (8)	0.0564 (10)	−0.0027 (7)	−0.0155 (8)	−0.0196 (7)
N6	0.0520 (10)	0.0456 (8)	0.0614 (10)	−0.0039 (7)	−0.0140 (8)	−0.0262 (8)
C35	0.0531 (13)	0.0500 (10)	0.0484 (12)	0.0015 (9)	−0.0134 (10)	−0.0144 (9)
C36	0.0641 (15)	0.0645 (12)	0.0592 (14)	0.0064 (11)	−0.0083 (12)	−0.0172 (10)
C37	0.0468 (13)	0.0766 (14)	0.0680 (15)	−0.0013 (11)	−0.0059 (11)	−0.0076 (12)
C38	0.0462 (13)	0.0684 (12)	0.0628 (14)	−0.0086 (10)	−0.0141 (11)	−0.0078 (11)
C39	0.0676 (16)	0.0980 (17)	0.0987 (19)	−0.0230 (13)	−0.0252 (14)	−0.0277 (15)
C40	0.0569 (13)	0.0490 (10)	0.0517 (12)	0.0027 (9)	−0.0185 (10)	−0.0169 (9)
C41	0.0540 (12)	0.0379 (8)	0.0441 (11)	0.0003 (8)	−0.0119 (9)	−0.0137 (8)
C42	0.0512 (12)	0.0373 (8)	0.0436 (11)	0.0018 (8)	−0.0119 (9)	−0.0139 (8)
C43	0.0604 (13)	0.0510 (10)	0.0471 (12)	−0.0013 (9)	−0.0068 (10)	−0.0215 (9)
C44	0.0560 (13)	0.0648 (12)	0.0518 (13)	−0.0074 (10)	0.0017 (10)	−0.0204 (10)
C45	0.0546 (13)	0.0463 (10)	0.0537 (12)	−0.0045 (9)	−0.0103 (10)	−0.0103 (9)
C46	0.0600 (14)	0.0670 (13)	0.0816 (16)	−0.0117 (11)	−0.0075 (12)	−0.0207 (12)
C47	0.0704 (17)	0.0668 (13)	0.109 (2)	−0.0104 (11)	−0.0305 (15)	−0.0327 (14)
C48	0.0719 (16)	0.0707 (13)	0.0986 (19)	0.0059 (12)	−0.0352 (15)	−0.0466 (13)
C49	0.0590 (13)	0.0609 (11)	0.0733 (14)	0.0073 (10)	−0.0225 (11)	−0.0347 (11)
C50	0.0530 (12)	0.0401 (9)	0.0531 (12)	0.0035 (8)	−0.0186 (10)	−0.0156 (8)
C51	0.0471 (11)	0.0446 (9)	0.0474 (11)	0.0065 (8)	−0.0113 (9)	−0.0179 (8)

Geometric parameters (Å, º) top

O1A—C1A	1.363 (7)	C12—H12	0.9300
O1A—C4A	1.364 (9)	C13—H13	0.9300
O1B—C1B	1.38 (3)	C14—H14	0.9300
O1B—C4B	1.37 (3)	C15—H15	0.9300
O2—C7	1.243 (2)	C17—H17	0.9300
O3—C9	1.354 (3)	C18—C19	1.347 (3)
O3—H3O	0.8200	C18—C23	1.425 (3)
O4—C21	1.372 (3)	C19—C20	1.402 (3)
O4—C18	1.375 (2)	C20—C21	1.332 (4)
O5—C24	1.235 (2)	C21—C22	1.479 (4)
O6—C26	1.353 (2)	C24—C25	1.482 (3)
O6—H6O	0.8200	C25—C26	1.428 (3)
O7—C35	1.369 (2)	C25—C34	1.380 (3)
O7—C38	1.378 (3)	C26—C27	1.365 (3)
O8—C41	1.242 (2)	C27—C28	1.406 (3)
O9—C43	1.363 (3)	C28—C29	1.420 (3)
O9—H9O	0.8200	C28—C33	1.414 (3)
N1—N2	1.373 (2)	C29—C30	1.350 (3)
N1—C6	1.273 (3)	C30—C31	1.400 (3)
N2—C7	1.338 (2)	C31—C32	1.358 (3)
N2—H2N	0.8600	C32—C33	1.410 (3)
N3—C23	1.281 (3)	C33—C34	1.406 (3)
N3—N4	1.388 (2)	C19—H19	0.9300
N4—C24	1.343 (2)	C20—H20	0.9300
N4—H4N	0.8600	C22—H22C	0.9600
N5—C40	1.278 (3)	C22—H22B	0.9600
N5—N6	1.387 (2)	C22—H22A	0.9600
N6—C41	1.337 (3)	C23—H23	0.9300
N6—H6N	0.8600	C27—H27	0.9300
C1A—C6	1.442 (6)	C29—H29	0.9300
C1A—C2A	1.323 (7)	C30—H30	0.9300
C1B—C2B	1.32 (4)	C31—H31	0.9300
C1B—C6	1.42 (3)	C32—H32	0.9300
C2A—C3A	1.405 (8)	C34—H34	0.9300
C2B—C3B	1.44 (4)	C35—C40	1.423 (3)
C3A—C4A	1.340 (9)	C35—C36	1.346 (3)
C3B—C4B	1.32 (4)	C36—C37	1.411 (3)
C4A—C5A	1.461 (8)	C37—C38	1.336 (3)
C4B—C5B	1.45 (2)	C38—C39	1.476 (3)
C7—C8	1.474 (3)	C41—C42	1.479 (3)
C8—C9	1.425 (3)	C42—C43	1.420 (3)
C8—C17	1.382 (2)	C42—C51	1.377 (2)
C9—C10	1.365 (3)	C43—C44	1.362 (3)
C10—C11	1.398 (3)	C44—C45	1.406 (3)
C11—C16	1.418 (3)	C45—C50	1.417 (3)
C11—C12	1.417 (3)	C45—C46	1.419 (3)
C12—C13	1.351 (4)	C46—C47	1.349 (3)
C13—C14	1.391 (4)	C47—C48	1.389 (3)
C14—C15	1.355 (3)	C48—C49	1.362 (3)
C15—C16	1.412 (3)	C49—C50	1.415 (3)
C16—C17	1.401 (3)	C50—C51	1.402 (3)
C2A—H2A	0.9300	C36—H36	0.9300
C2B—H2B	0.9300	C37—H37	0.9300
C3A—H3A	0.9300	C39—H39A	0.9600
C3B—H3B	0.9300	C39—H39B	0.9600
C5A—H5B	0.9600	C39—H39C	0.9600
C5A—H5A	0.9600	C40—H40	0.9300
C5A—H5C	0.9600	C44—H44	0.9300
C5B—H5D	0.9600	C46—H46	0.9300
C5B—H5E	0.9600	C47—H47	0.9300
C5B—H5F	0.9600	C48—H48	0.9300
C6—H6	0.9300	C49—H49	0.9300
C10—H10	0.9300	C51—H51	0.9300

C1A—O1A—C4A	107.6 (5)	N3—C23—C18	124.41 (18)
C1B—O1B—C4B	109.4 (19)	O5—C24—C25	121.60 (17)
C9—O3—H3O	109.00	O5—C24—N4	120.42 (17)
C18—O4—C21	106.72 (16)	N4—C24—C25	117.98 (16)
C26—O6—H6O	109.00	C24—C25—C26	119.01 (16)
C35—O7—C38	106.53 (15)	C26—C25—C34	117.86 (16)
C43—O9—H9O	109.00	C24—C25—C34	123.13 (16)
N2—N1—C6	114.76 (16)	C25—C26—C27	119.91 (17)
N1—N2—C7	118.84 (15)	O6—C26—C27	117.64 (18)
C7—N2—H2N	121.00	O6—C26—C25	122.46 (17)
N1—N2—H2N	121.00	C26—C27—C28	122.19 (18)
N4—N3—C23	113.59 (15)	C29—C28—C33	117.99 (18)
N3—N4—C24	119.83 (15)	C27—C28—C29	123.13 (18)
C24—N4—H4N	120.00	C27—C28—C33	118.88 (17)
N3—N4—H4N	120.00	C28—C29—C30	120.89 (19)
N6—N5—C40	114.51 (15)	C29—C30—C31	121.2 (2)
N5—N6—C41	119.07 (14)	C30—C31—C32	119.6 (2)
N5—N6—H6N	120.00	C31—C32—C33	121.08 (18)
C41—N6—H6N	120.00	C28—C33—C32	119.25 (16)
C2A—C1A—C6	135.8 (5)	C28—C33—C34	118.02 (17)
O1A—C1A—C6	114.8 (4)	C32—C33—C34	122.73 (16)
O1A—C1A—C2A	109.3 (5)	C25—C34—C33	123.12 (16)
C2B—C1B—C6	138 (2)	C18—C19—H19	126.00
O1B—C1B—C6	114 (2)	C20—C19—H19	126.00
O1B—C1B—C2B	108 (2)	C19—C20—H20	126.00
C1A—C2A—C3A	107.2 (5)	C21—C20—H20	126.00
C1B—C2B—C3B	107 (2)	H22A—C22—H22C	109.00
C2A—C3A—C4A	107.5 (5)	C21—C22—H22A	110.00
C2B—C3B—C4B	108 (3)	C21—C22—H22B	109.00
C3A—C4A—C5A	135.6 (7)	H22A—C22—H22B	109.00
O1A—C4A—C3A	108.3 (6)	H22B—C22—H22C	109.00
O1A—C4A—C5A	116.0 (6)	C21—C22—H22C	110.00
C3B—C4B—C5B	136 (2)	N3—C23—H23	118.00
O1B—C4B—C5B	116.6 (18)	C18—C23—H23	118.00
O1B—C4B—C3B	107 (2)	C26—C27—H27	119.00
N1—C6—C1B	130.3 (9)	C28—C27—H27	119.00
N1—C6—C1A	116.7 (2)	C28—C29—H29	120.00
N2—C7—C8	117.68 (16)	C30—C29—H29	120.00
O2—C7—N2	121.55 (17)	C29—C30—H30	119.00
O2—C7—C8	120.73 (17)	C31—C30—H30	119.00
C9—C8—C17	118.17 (16)	C32—C31—H31	120.00
C7—C8—C9	119.94 (16)	C30—C31—H31	120.00
C7—C8—C17	121.53 (17)	C33—C32—H32	119.00
O3—C9—C10	118.59 (19)	C31—C32—H32	119.00
O3—C9—C8	120.92 (18)	C25—C34—H34	118.00
C8—C9—C10	120.49 (18)	C33—C34—H34	118.00
C9—C10—C11	121.44 (19)	O7—C35—C40	120.29 (17)
C12—C11—C16	117.87 (18)	C36—C35—C40	130.21 (18)
C10—C11—C12	123.03 (19)	O7—C35—C36	109.49 (18)
C10—C11—C16	119.08 (18)	C35—C36—C37	107.10 (19)
C11—C12—C13	120.6 (2)	C36—C37—C38	107.2 (2)
C12—C13—C14	121.5 (2)	O7—C38—C37	109.63 (19)
C13—C14—C15	120.1 (2)	O7—C38—C39	116.42 (18)
C14—C15—C16	120.5 (2)	C37—C38—C39	133.9 (2)
C11—C16—C17	118.68 (16)	N5—C40—C35	122.94 (18)
C11—C16—C15	119.50 (17)	N6—C41—C42	117.24 (15)
C15—C16—C17	121.81 (18)	O8—C41—N6	121.25 (18)
C8—C17—C16	122.13 (17)	O8—C41—C42	121.51 (17)
C3A—C2A—H2A	126.00	C41—C42—C43	119.03 (15)
C1A—C2A—H2A	126.00	C41—C42—C51	122.69 (16)
C3B—C2B—H2B	127.00	C43—C42—C51	118.25 (17)
C1B—C2B—H2B	126.00	C42—C43—C44	120.47 (17)
C2A—C3A—H3A	126.00	O9—C43—C42	121.35 (18)
C4A—C3A—H3A	126.00	O9—C43—C44	118.18 (18)
C2B—C3B—H3B	126.00	C43—C44—C45	121.56 (19)
C4B—C3B—H3B	126.00	C44—C45—C46	123.23 (19)
C4A—C5A—H5C	109.00	C44—C45—C50	118.78 (18)
H5B—C5A—H5C	110.00	C46—C45—C50	117.97 (17)
H5A—C5A—H5C	109.00	C45—C46—C47	121.1 (2)
C4A—C5A—H5A	109.00	C46—C47—C48	121.1 (2)
H5A—C5A—H5B	109.00	C47—C48—C49	120.0 (2)
C4A—C5A—H5B	109.00	C48—C49—C50	120.8 (2)
C4B—C5B—H5E	110.00	C45—C50—C49	118.96 (18)
H5D—C5B—H5E	110.00	C45—C50—C51	118.52 (16)
C4B—C5B—H5D	110.00	C49—C50—C51	122.52 (18)
H5E—C5B—H5F	109.00	C42—C51—C50	122.39 (17)
C4B—C5B—H5F	109.00	C35—C36—H36	126.00
H5D—C5B—H5F	109.00	C37—C36—H36	126.00
C1A—C6—H6	122.00	C36—C37—H37	126.00
N1—C6—H6	122.00	C38—C37—H37	126.00
C1B—C6—H6	108.00	C38—C39—H39A	109.00
C11—C10—H10	119.00	C38—C39—H39B	109.00
C9—C10—H10	119.00	C38—C39—H39C	109.00
C13—C12—H12	120.00	H39A—C39—H39B	109.00
C11—C12—H12	120.00	H39A—C39—H39C	109.00
C14—C13—H13	119.00	H39B—C39—H39C	110.00
C12—C13—H13	119.00	N5—C40—H40	119.00
C15—C14—H14	120.00	C35—C40—H40	119.00
C13—C14—H14	120.00	C43—C44—H44	119.00
C14—C15—H15	120.00	C45—C44—H44	119.00
C16—C15—H15	120.00	C45—C46—H46	119.00
C8—C17—H17	119.00	C47—C46—H46	119.00
C16—C17—H17	119.00	C46—C47—H47	119.00
O4—C18—C23	120.66 (17)	C48—C47—H47	119.00
C19—C18—C23	130.56 (19)	C47—C48—H48	120.00
O4—C18—C19	108.63 (18)	C49—C48—H48	120.00
C18—C19—C20	107.7 (2)	C48—C49—H49	120.00
C19—C20—C21	107.2 (2)	C50—C49—H49	120.00
O4—C21—C22	116.5 (2)	C42—C51—H51	119.00
O4—C21—C20	109.8 (2)	C50—C51—H51	119.00
C20—C21—C22	133.7 (2)

C4A—O1A—C1A—C2A	0.9 (7)	C19—C20—C21—O4	−0.9 (3)
C4A—O1A—C1A—C6	177.9 (5)	C19—C20—C21—C22	177.8 (3)
C1A—O1A—C4A—C3A	−0.3 (7)	N4—C24—C25—C34	13.2 (3)
C1A—O1A—C4A—C5A	176.8 (5)	O5—C24—C25—C26	13.1 (3)
C21—O4—C18—C19	−0.5 (2)	O5—C24—C25—C34	−167.32 (19)
C21—O4—C18—C23	175.60 (19)	N4—C24—C25—C26	−166.32 (17)
C18—O4—C21—C20	0.9 (2)	C24—C25—C26—C27	178.46 (18)
C18—O4—C21—C22	−178.1 (2)	C34—C25—C26—O6	179.23 (18)
C35—O7—C38—C37	−0.9 (2)	C34—C25—C26—C27	−1.1 (3)
C35—O7—C38—C39	177.11 (18)	C24—C25—C34—C33	−179.04 (18)
C38—O7—C35—C36	0.2 (2)	C26—C25—C34—C33	0.5 (3)
C38—O7—C35—C40	179.94 (18)	C24—C25—C26—O6	−1.2 (3)
N2—N1—C6—C1A	174.2 (3)	O6—C26—C27—C28	−179.11 (19)
C6—N1—N2—C7	−179.29 (17)	C25—C26—C27—C28	1.2 (3)
N1—N2—C7—C8	167.77 (15)	C26—C27—C28—C29	179.2 (2)
N1—N2—C7—O2	−9.9 (3)	C26—C27—C28—C33	−0.7 (3)
N4—N3—C23—C18	−174.98 (19)	C27—C28—C29—C30	−179.7 (2)
C23—N3—N4—C24	−175.09 (18)	C33—C28—C29—C30	0.2 (3)
N3—N4—C24—O5	5.5 (3)	C27—C28—C33—C32	−179.56 (19)
N3—N4—C24—C25	−175.01 (16)	C27—C28—C33—C34	0.0 (3)
C40—N5—N6—C41	−177.91 (17)	C29—C28—C33—C32	0.6 (3)
N6—N5—C40—C35	178.16 (17)	C29—C28—C33—C34	−179.85 (18)
N5—N6—C41—O8	0.9 (3)	C28—C29—C30—C31	−0.7 (3)
N5—N6—C41—C42	−179.52 (15)	C29—C30—C31—C32	0.4 (3)
O1A—C1A—C2A—C3A	−1.1 (6)	C30—C31—C32—C33	0.4 (3)
C6—C1A—C2A—C3A	−177.2 (6)	C31—C32—C33—C28	−0.8 (3)
C2A—C1A—C6—N1	−9.9 (8)	C31—C32—C33—C34	179.6 (2)
O1A—C1A—C6—N1	174.2 (4)	C28—C33—C34—C25	0.0 (3)
C1A—C2A—C3A—C4A	0.9 (7)	C32—C33—C34—C25	179.59 (19)
C2A—C3A—C4A—C5A	−176.6 (7)	O7—C35—C36—C37	0.5 (2)
C2A—C3A—C4A—O1A	−0.3 (8)	C40—C35—C36—C37	−179.2 (2)
O2—C7—C8—C9	−17.6 (3)	O7—C35—C40—N5	−9.8 (3)
N2—C7—C8—C17	−22.3 (3)	C36—C35—C40—N5	170.0 (2)
N2—C7—C8—C9	164.73 (17)	C35—C36—C37—C38	−1.0 (3)
O2—C7—C8—C17	155.33 (18)	C36—C37—C38—O7	1.2 (2)
C7—C8—C9—O3	−5.2 (3)	C36—C37—C38—C39	−176.3 (2)
C7—C8—C9—C10	174.57 (18)	O8—C41—C42—C43	17.5 (3)
C7—C8—C17—C16	−173.73 (17)	O8—C41—C42—C51	−160.42 (17)
C17—C8—C9—O3	−178.42 (18)	N6—C41—C42—C43	−162.12 (16)
C17—C8—C9—C10	1.4 (3)	N6—C41—C42—C51	20.0 (3)
C9—C8—C17—C16	−0.7 (3)	C41—C42—C43—O9	−0.2 (3)
C8—C9—C10—C11	−1.4 (3)	C41—C42—C43—C44	179.53 (17)
O3—C9—C10—C11	178.38 (19)	C51—C42—C43—O9	177.80 (17)
C9—C10—C11—C12	−177.7 (2)	C51—C42—C43—C44	−2.5 (3)
C9—C10—C11—C16	0.7 (3)	C41—C42—C51—C50	179.96 (17)
C12—C11—C16—C17	178.51 (18)	C43—C42—C51—C50	2.0 (3)
C10—C11—C16—C15	−178.63 (19)	O9—C43—C44—C45	−178.71 (18)
C10—C11—C16—C17	0.0 (3)	C42—C43—C44—C45	1.5 (3)
C12—C11—C16—C15	−0.2 (3)	C43—C44—C45—C46	177.9 (2)
C16—C11—C12—C13	0.1 (3)	C43—C44—C45—C50	−0.1 (3)
C10—C11—C12—C13	178.5 (2)	C44—C45—C46—C47	−177.8 (2)
C11—C12—C13—C14	0.1 (4)	C50—C45—C46—C47	0.2 (3)
C12—C13—C14—C15	−0.3 (4)	C44—C45—C50—C49	178.90 (18)
C13—C14—C15—C16	0.2 (4)	C44—C45—C50—C51	−0.3 (3)
C14—C15—C16—C17	−178.6 (2)	C46—C45—C50—C49	0.8 (3)
C14—C15—C16—C11	0.0 (3)	C46—C45—C50—C51	−178.44 (18)
C11—C16—C17—C8	0.0 (3)	C45—C46—C47—C48	−1.1 (4)
C15—C16—C17—C8	178.60 (18)	C46—C47—C48—C49	0.9 (4)
C23—C18—C19—C20	−175.6 (2)	C47—C48—C49—C50	0.1 (3)
O4—C18—C23—N3	9.4 (3)	C48—C49—C50—C45	−1.0 (3)
O4—C18—C19—C20	−0.1 (2)	C48—C49—C50—C51	178.27 (19)
C19—C18—C23—N3	−175.5 (2)	C45—C50—C51—C42	−0.7 (3)
C18—C19—C20—C21	0.6 (3)	C49—C50—C51—C42	−179.87 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O8ⁱ	0.86	2.15	2.869 (2)	142
N4—H4N···O2	0.86	2.20	2.896 (2)	137
N6—H6N···O5ⁱⁱ	0.86	2.36	3.074 (2)	140
N6—H6N···N3ⁱⁱ	0.86	2.44	3.212 (2)	149
O3—H3O···O2	0.82	1.89	2.612 (3)	145
O6—H6O···O5	0.82	1.89	2.603 (2)	145
O9—H9O···O8	0.82	1.86	2.588 (2)	147
C34—H34···O2	0.93	2.48	3.398 (3)	167
C40—H40···O5ⁱⁱ	0.93	2.42	3.185 (3)	140
C44—H44···O1A	0.93	2.59	3.514 (5)	176
C48—H48···O3ⁱⁱ	0.93	2.51	3.149 (3)	126

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄N₂O₃
M_r	294.30
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	10.604 (4), 12.321 (5), 18.615 (3)
α, β, γ (°)	71.351 (5), 73.742 (4), 84.280 (5)
V (Å³)	2212.1 (13)
Z	6
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.20 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.975, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	48594, 11199, 5268
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.676

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.130, 0.99
No. of reflections	11199
No. of parameters	624
No. of restraints	7
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.16

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O8ⁱ	0.86	2.15	2.869 (2)	142
N4—H4N···O2	0.86	2.20	2.896 (2)	137
N6—H6N···O5ⁱⁱ	0.86	2.36	3.074 (2)	140
N6—H6N···N3ⁱⁱ	0.86	2.44	3.212 (2)	149
O3—H3O···O2	0.82	1.89	2.612 (3)	145
O6—H6O···O5	0.82	1.89	2.603 (2)	145
O9—H9O···O8	0.82	1.86	2.588 (2)	147
C34—H34···O2	0.93	2.48	3.398 (3)	167
C40—H40···O5ⁱⁱ	0.93	2.42	3.185 (3)	140
C44—H44···O1A	0.93	2.59	3.514 (5)	176
C48—H48···O3ⁱⁱ	0.93	2.51	3.149 (3)	126

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

Acknowledgements

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan and Bana International, Karachi, Pakistan, for funding the purchase of the diffractometer at GCU, Lahore and for technical support, respectively.

References

Bai, Z.-C. & Jing, Z.-L. (2007). Acta Cryst. E63, o3822. Web of Science CSD CrossRef IUCr Journals Google Scholar
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
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
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Shafiq, Z., Yaqub, M., Tahir, M. N., Nawaz, M. H. & Iqbal, M. S. (2009b). Acta Cryst. E65, o2495. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 65| Part 11| November 2009| Pages o2845-o2846

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

3-Hydr­­oxy-N′-[(Z)-(5-methyl-2-fur­yl)methyl­­idene]naphthalene-2-carbo­hydrazide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-Hydroxy-N′-[(Z)-(5-methyl-2-furyl)methylidene]naphthalene-2-carbohydrazide