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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2845–o2846.
Published online 2009 October 23. doi:  10.1107/S1600536809043141
PMCID: PMC2971404

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

Abstract

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

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Object name is e-65-o2845-scheme1.jpg

Experimental

Crystal data

  • C17H14N2O3
  • M r = 294.30
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2845-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.130
  • S = 0.99
  • 11199 reflections
  • 624 parameters
  • 7 restraints
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.16 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043141/hb5157Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

The disorder in one of the 5-methylfuran was detected through higher values of thermal parameters and from residual peaks. To overcome the large or small bond distances DFIX was utilized during refinement. The group containing lower occupancy factor was refined using EADP.

The H-atoms were positioned geometrically (O–H = 0.82 Å, N–H = 0.86 Å, C–H = 0.93–0.96 Å) and refined as riding with Uiso(H) = 1.2Ueq(carrier) or 1.5Ueq(methyl C).

Figures

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.

Crystal data

C17H14N2O3Z = 6
Mr = 294.30F(000) = 924
Triclinic, P1Dx = 1.326 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.604 (4) ÅCell parameters from 5268 reflections
b = 12.321 (5) Åθ = 2.4–28.7°
c = 18.615 (3) ŵ = 0.09 mm1
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

Bruker Kappa APEXII CCD diffractometer11199 independent reflections
Radiation source: fine-focus sealed tube5268 reflections with I > 2σ(I)
graphiteRint = 0.044
Detector resolution: 7.40 pixels mm-1θmax = 28.7°, θmin = 2.4°
ω scansh = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −16→16
Tmin = 0.975, Tmax = 0.985l = −24→24
48594 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H-atom parameters constrained
S = 0.99w = 1/[σ2(Fo2) + (0.0516P)2 + 0.1613P] where P = (Fo2 + 2Fc2)/3
11199 reflections(Δ/σ)max = 0.001
624 parametersΔρmax = 0.16 e Å3
7 restraintsΔρmin = −0.16 e Å3

Special details

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)

xyzUiso*/UeqOcc. (<1)
O1A0.9959 (4)0.1541 (3)0.4542 (3)0.0562 (9)0.747 (3)
O20.65580 (14)0.43845 (9)0.24178 (8)0.0631 (5)
O30.47122 (17)0.46866 (13)0.16900 (11)0.0921 (7)
N10.80165 (15)0.29221 (12)0.32581 (9)0.0531 (6)
N20.73255 (15)0.25872 (12)0.28429 (8)0.0510 (5)
C1A0.9445 (6)0.2436 (3)0.4053 (3)0.0483 (11)0.747 (3)
C2A0.9913 (5)0.3407 (4)0.4028 (3)0.0636 (16)0.747 (3)
C3A1.0743 (4)0.3126 (4)0.4533 (4)0.0673 (16)0.747 (3)
C4A1.0758 (8)0.1983 (6)0.4837 (4)0.0562 (11)0.747 (3)
C5A1.1352 (3)0.1156 (3)0.54123 (18)0.0815 (12)0.747 (3)
C60.86051 (19)0.21126 (16)0.36670 (11)0.0541 (7)
C70.66876 (18)0.33839 (14)0.23901 (10)0.0476 (6)
C80.61847 (17)0.30478 (13)0.18306 (10)0.0454 (6)
C90.52377 (19)0.37537 (15)0.14756 (12)0.0569 (7)
C100.4845 (2)0.35028 (16)0.09087 (12)0.0631 (8)
C110.53739 (18)0.25684 (15)0.06467 (11)0.0540 (7)
C120.5025 (2)0.23053 (19)0.00403 (12)0.0708 (8)
C130.5589 (3)0.1406 (2)−0.02024 (13)0.0818 (10)
C140.6522 (3)0.07105 (19)0.01321 (13)0.0792 (10)
C150.6889 (2)0.09305 (16)0.07126 (12)0.0636 (8)
C160.63285 (18)0.18610 (14)0.09851 (10)0.0472 (6)
C170.67088 (17)0.21241 (13)0.15727 (10)0.0469 (6)
C1B0.947 (3)0.2146 (16)0.4118 (16)0.086 (3)0.253 (3)
C2B1.014 (3)0.141 (2)0.4568 (17)0.086 (3)0.253 (3)
C3B1.071 (3)0.205 (2)0.4924 (18)0.086 (3)0.253 (3)
C4B1.035 (2)0.3134 (17)0.4682 (16)0.086 (3)0.253 (3)
C5B1.0541 (8)0.4178 (3)0.4832 (5)0.086 (3)0.253 (3)
O1B0.9529 (14)0.3203 (12)0.4215 (9)0.086 (3)0.253 (3)
O40.65494 (13)0.67372 (10)0.43795 (7)0.0614 (5)
O50.84414 (14)0.82850 (10)0.14400 (8)0.0702 (5)
O60.95849 (17)0.89165 (10)−0.00598 (9)0.0790 (6)
N30.76595 (14)0.66539 (12)0.28104 (9)0.0485 (5)
N40.80070 (15)0.64348 (11)0.20930 (9)0.0515 (6)
C180.69926 (19)0.57430 (15)0.42005 (12)0.0550 (7)
C190.6813 (2)0.48682 (18)0.48745 (13)0.0751 (9)
C200.6243 (2)0.5319 (2)0.54963 (13)0.0788 (9)
C210.6085 (2)0.6441 (2)0.51818 (13)0.0687 (9)
C220.5512 (3)0.7378 (2)0.55129 (15)0.1067 (11)
C230.74565 (19)0.57470 (15)0.34036 (12)0.0554 (7)
C240.83427 (17)0.73040 (14)0.14223 (11)0.0474 (6)
C250.85989 (16)0.70440 (13)0.06697 (10)0.0442 (6)
C260.92304 (18)0.78819 (14)−0.00429 (12)0.0527 (7)
C270.95030 (19)0.76484 (15)−0.07400 (12)0.0586 (7)
C280.91602 (18)0.66060 (15)−0.07890 (11)0.0510 (7)
C290.9420 (2)0.63507 (18)−0.15087 (12)0.0663 (8)
C300.9066 (2)0.53385 (19)−0.15254 (13)0.0698 (9)
C310.8445 (2)0.45044 (18)−0.08347 (13)0.0650 (8)
C320.81850 (19)0.47160 (15)−0.01349 (11)0.0548 (7)
C330.85240 (17)0.57673 (14)−0.00917 (10)0.0446 (6)
C340.82635 (17)0.60206 (14)0.06213 (10)0.0461 (6)
O7−0.09686 (12)−0.07040 (10)0.73469 (7)0.0568 (5)
O80.38574 (13)−0.03678 (10)0.64992 (8)0.0619 (5)
O90.61823 (14)0.03617 (13)0.56670 (9)0.0758 (6)
N50.14612 (15)0.01505 (11)0.72496 (9)0.0499 (5)
N60.25674 (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)
C400.0380 (2)0.05329 (15)0.76010 (11)0.0515 (7)
C410.37427 (18)0.04222 (13)0.67934 (10)0.0453 (6)
C420.48957 (17)0.10614 (13)0.67331 (10)0.0439 (6)
C430.60845 (19)0.09994 (14)0.61589 (11)0.0527 (7)
C440.7161 (2)0.15844 (16)0.60846 (11)0.0598 (7)
C450.71458 (19)0.22425 (14)0.65804 (11)0.0533 (7)
C460.8259 (2)0.28335 (17)0.65383 (13)0.0716 (8)
C470.8210 (2)0.34244 (17)0.70435 (15)0.0785 (10)
C480.7061 (2)0.34898 (17)0.76139 (14)0.0731 (9)
C490.5965 (2)0.29390 (15)0.76774 (12)0.0604 (7)
C500.59774 (18)0.22941 (13)0.71683 (11)0.0477 (6)
C510.48799 (18)0.16903 (13)0.72286 (10)0.0462 (6)
H5B1.196600.067800.515960.1222*0.747 (3)
H5C1.067830.069040.582430.1222*0.747 (3)
H100.421220.396350.069190.0758*
H120.440270.27554−0.019270.0849*
H130.534850.12481−0.060210.0980*
H140.689450.00942−0.004280.0950*
H150.751470.046450.093330.0764*
H170.733410.166190.179630.0563*
H60.849850.135030.371470.0649*
H2A0.972610.413950.373190.0759*0.747 (3)
H2N0.730330.187770.287340.0613*
H3A1.119890.363980.463720.0806*0.747 (3)
H3O0.509680.479940.198480.1381*
H5A1.180230.155690.563100.1222*0.747 (3)
H2B1.021850.062760.464230.1030*0.253 (3)
H3B1.124560.174770.526350.1030*0.253 (3)
H5D1.114520.465930.438250.1288*0.253 (3)
H5E1.088780.399620.528170.1288*0.253 (3)
H5F0.971340.457200.493290.1288*0.253 (3)
H4N0.800730.574430.207800.0618*
H6O0.941240.895220.038990.1186*
H190.702700.410310.491930.0901*
H200.601830.491060.602870.0945*
H22A0.526750.708630.607630.1597*
H22B0.474790.768500.533260.1597*
H22C0.614760.797220.534480.1597*
H230.762310.504360.330770.0664*
H270.992980.81971−0.119790.0703*
H290.984050.68880−0.197490.0795*
H300.923720.51929−0.200430.0838*
H310.821210.38089−0.085500.0780*
H320.777660.415860.032350.0658*
H340.784530.547240.108220.0553*
H6N0.249820.128860.737050.0606*
H9O0.549820.001090.578820.1136*
H36−0.225060.075660.846060.0782*
H37−0.38499−0.048050.831160.0831*
H39A−0.35821−0.185350.736880.1295*
H39B−0.22443−0.251440.739040.1295*
H39C−0.23452−0.147930.665300.1295*
H400.040780.114050.779060.0618*
H440.792380.154810.569650.0717*
H460.903630.281320.615590.0859*
H470.895760.379390.700930.0940*
H480.704070.391000.795260.0877*
H490.519890.298730.806030.0724*
H510.411360.171540.761720.0554*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.062 (2)0.0574 (15)0.0452 (13)−0.0028 (14)−0.0083 (13)−0.0145 (12)
O20.0890 (10)0.0427 (7)0.0647 (9)−0.0060 (6)−0.0230 (8)−0.0220 (6)
O30.1054 (13)0.0801 (10)0.1190 (14)0.0425 (9)−0.0531 (11)−0.0613 (10)
N10.0606 (10)0.0534 (9)0.0515 (10)−0.0088 (8)−0.0150 (9)−0.0219 (8)
N20.0667 (10)0.0432 (8)0.0508 (10)−0.0109 (7)−0.0196 (8)−0.0180 (7)
C1A0.0464 (18)0.057 (2)0.0424 (18)0.0036 (18)−0.0095 (14)−0.0197 (19)
C2A0.071 (3)0.059 (2)0.074 (3)0.0093 (19)−0.039 (3)−0.024 (2)
C3A0.073 (3)0.066 (2)0.076 (3)0.004 (2)−0.035 (3)−0.0274 (19)
C4A0.0472 (19)0.075 (2)0.047 (2)0.0022 (16)−0.0127 (18)−0.0199 (18)
C5A0.083 (2)0.095 (2)0.064 (2)0.0103 (18)−0.0319 (18)−0.0133 (18)
C60.0601 (13)0.0591 (11)0.0469 (12)−0.0063 (10)−0.0103 (10)−0.0230 (10)
C70.0553 (12)0.0408 (9)0.0439 (11)−0.0110 (8)−0.0042 (9)−0.0136 (8)
C80.0510 (11)0.0414 (9)0.0422 (11)−0.0067 (8)−0.0070 (9)−0.0132 (8)
C90.0569 (13)0.0492 (10)0.0654 (14)0.0074 (9)−0.0131 (11)−0.0237 (10)
C100.0599 (13)0.0643 (12)0.0713 (15)0.0098 (10)−0.0285 (12)−0.0224 (11)
C110.0554 (12)0.0556 (10)0.0511 (12)−0.0067 (9)−0.0145 (10)−0.0143 (9)
C120.0808 (16)0.0804 (14)0.0614 (14)−0.0020 (12)−0.0337 (12)−0.0224 (12)
C130.109 (2)0.0920 (16)0.0615 (15)−0.0052 (15)−0.0349 (15)−0.0346 (13)
C140.1039 (19)0.0793 (15)0.0710 (16)0.0092 (14)−0.0291 (15)−0.0432 (13)
C150.0791 (15)0.0613 (11)0.0597 (14)0.0085 (10)−0.0227 (12)−0.0299 (10)
C160.0510 (12)0.0468 (9)0.0431 (11)−0.0055 (8)−0.0102 (9)−0.0134 (8)
C170.0526 (12)0.0421 (9)0.0461 (11)−0.0031 (8)−0.0133 (9)−0.0124 (8)
C1B0.095 (5)0.092 (4)0.096 (5)0.001 (3)−0.040 (4)−0.049 (4)
C2B0.095 (5)0.092 (4)0.096 (5)0.001 (3)−0.040 (4)−0.049 (4)
C3B0.095 (5)0.092 (4)0.096 (5)0.001 (3)−0.040 (4)−0.049 (4)
C4B0.095 (5)0.092 (4)0.096 (5)0.001 (3)−0.040 (4)−0.049 (4)
C5B0.095 (5)0.092 (4)0.096 (5)0.001 (3)−0.040 (4)−0.049 (4)
O1B0.095 (5)0.092 (4)0.096 (5)0.001 (3)−0.040 (4)−0.049 (4)
O40.0708 (9)0.0619 (8)0.0501 (9)0.0040 (7)−0.0119 (7)−0.0201 (7)
O50.0981 (11)0.0463 (7)0.0701 (10)−0.0098 (7)−0.0129 (8)−0.0283 (7)
O60.1093 (12)0.0463 (7)0.0755 (10)−0.0209 (7)−0.0129 (10)−0.0145 (7)
N30.0586 (10)0.0450 (8)0.0495 (10)0.0013 (7)−0.0179 (8)−0.0221 (8)
N40.0728 (11)0.0406 (8)0.0486 (10)0.0017 (7)−0.0177 (8)−0.0232 (8)
C180.0678 (14)0.0488 (10)0.0531 (13)−0.0021 (9)−0.0245 (11)−0.0140 (10)
C190.1016 (19)0.0621 (13)0.0624 (15)−0.0051 (12)−0.0329 (14)−0.0090 (12)
C200.0849 (17)0.0909 (17)0.0506 (14)−0.0115 (14)−0.0202 (13)−0.0028 (13)
C210.0616 (14)0.0959 (17)0.0458 (14)−0.0006 (12)−0.0091 (11)−0.0224 (12)
C220.109 (2)0.133 (2)0.0724 (17)0.0223 (18)0.0000 (16)−0.0515 (17)
C230.0738 (14)0.0473 (10)0.0560 (13)0.0033 (9)−0.0280 (11)−0.0224 (10)
C240.0484 (11)0.0426 (9)0.0566 (12)0.0022 (8)−0.0160 (9)−0.0214 (9)
C250.0449 (11)0.0400 (9)0.0487 (11)0.0030 (8)−0.0137 (9)−0.0147 (8)
C260.0566 (12)0.0407 (9)0.0578 (13)0.0002 (8)−0.0142 (10)−0.0120 (9)
C270.0638 (14)0.0494 (10)0.0489 (13)−0.0021 (9)−0.0083 (10)−0.0018 (9)
C280.0512 (12)0.0539 (10)0.0460 (12)0.0078 (9)−0.0147 (10)−0.0137 (9)
C290.0742 (15)0.0729 (14)0.0434 (13)0.0049 (11)−0.0108 (11)−0.0123 (10)
C300.0820 (16)0.0849 (15)0.0491 (14)0.0121 (13)−0.0179 (12)−0.0326 (12)
C310.0743 (15)0.0703 (13)0.0625 (15)0.0044 (11)−0.0229 (12)−0.0341 (12)
C320.0632 (13)0.0554 (10)0.0490 (12)−0.0049 (9)−0.0131 (10)−0.0204 (9)
C330.0430 (11)0.0478 (9)0.0423 (11)0.0023 (8)−0.0115 (9)−0.0136 (9)
C340.0503 (11)0.0440 (9)0.0415 (11)−0.0043 (8)−0.0090 (9)−0.0112 (8)
O70.0468 (8)0.0645 (8)0.0599 (9)−0.0066 (6)−0.0104 (7)−0.0213 (7)
O80.0701 (9)0.0503 (7)0.0711 (9)−0.0062 (6)−0.0075 (7)−0.0344 (7)
O90.0750 (10)0.0908 (10)0.0713 (10)−0.0099 (8)0.0016 (8)−0.0534 (9)
N50.0502 (10)0.0474 (8)0.0564 (10)−0.0027 (7)−0.0155 (8)−0.0196 (7)
N60.0520 (10)0.0456 (8)0.0614 (10)−0.0039 (7)−0.0140 (8)−0.0262 (8)
C350.0531 (13)0.0500 (10)0.0484 (12)0.0015 (9)−0.0134 (10)−0.0144 (9)
C360.0641 (15)0.0645 (12)0.0592 (14)0.0064 (11)−0.0083 (12)−0.0172 (10)
C370.0468 (13)0.0766 (14)0.0680 (15)−0.0013 (11)−0.0059 (11)−0.0076 (12)
C380.0462 (13)0.0684 (12)0.0628 (14)−0.0086 (10)−0.0141 (11)−0.0078 (11)
C390.0676 (16)0.0980 (17)0.0987 (19)−0.0230 (13)−0.0252 (14)−0.0277 (15)
C400.0569 (13)0.0490 (10)0.0517 (12)0.0027 (9)−0.0185 (10)−0.0169 (9)
C410.0540 (12)0.0379 (8)0.0441 (11)0.0003 (8)−0.0119 (9)−0.0137 (8)
C420.0512 (12)0.0373 (8)0.0436 (11)0.0018 (8)−0.0119 (9)−0.0139 (8)
C430.0604 (13)0.0510 (10)0.0471 (12)−0.0013 (9)−0.0068 (10)−0.0215 (9)
C440.0560 (13)0.0648 (12)0.0518 (13)−0.0074 (10)0.0017 (10)−0.0204 (10)
C450.0546 (13)0.0463 (10)0.0537 (12)−0.0045 (9)−0.0103 (10)−0.0103 (9)
C460.0600 (14)0.0670 (13)0.0816 (16)−0.0117 (11)−0.0075 (12)−0.0207 (12)
C470.0704 (17)0.0668 (13)0.109 (2)−0.0104 (11)−0.0305 (15)−0.0327 (14)
C480.0719 (16)0.0707 (13)0.0986 (19)0.0059 (12)−0.0352 (15)−0.0466 (13)
C490.0590 (13)0.0609 (11)0.0733 (14)0.0073 (10)−0.0225 (11)−0.0347 (11)
C500.0530 (12)0.0401 (9)0.0531 (12)0.0035 (8)−0.0186 (10)−0.0156 (8)
C510.0471 (11)0.0446 (9)0.0474 (11)0.0065 (8)−0.0113 (9)−0.0179 (8)

Geometric parameters (Å, °)

O1A—C1A1.363 (7)C12—H120.9300
O1A—C4A1.364 (9)C13—H130.9300
O1B—C1B1.38 (3)C14—H140.9300
O1B—C4B1.37 (3)C15—H150.9300
O2—C71.243 (2)C17—H170.9300
O3—C91.354 (3)C18—C191.347 (3)
O3—H3O0.8200C18—C231.425 (3)
O4—C211.372 (3)C19—C201.402 (3)
O4—C181.375 (2)C20—C211.332 (4)
O5—C241.235 (2)C21—C221.479 (4)
O6—C261.353 (2)C24—C251.482 (3)
O6—H6O0.8200C25—C261.428 (3)
O7—C351.369 (2)C25—C341.380 (3)
O7—C381.378 (3)C26—C271.365 (3)
O8—C411.242 (2)C27—C281.406 (3)
O9—C431.363 (3)C28—C291.420 (3)
O9—H9O0.8200C28—C331.414 (3)
N1—N21.373 (2)C29—C301.350 (3)
N1—C61.273 (3)C30—C311.400 (3)
N2—C71.338 (2)C31—C321.358 (3)
N2—H2N0.8600C32—C331.410 (3)
N3—C231.281 (3)C33—C341.406 (3)
N3—N41.388 (2)C19—H190.9300
N4—C241.343 (2)C20—H200.9300
N4—H4N0.8600C22—H22C0.9600
N5—C401.278 (3)C22—H22B0.9600
N5—N61.387 (2)C22—H22A0.9600
N6—C411.337 (3)C23—H230.9300
N6—H6N0.8600C27—H270.9300
C1A—C61.442 (6)C29—H290.9300
C1A—C2A1.323 (7)C30—H300.9300
C1B—C2B1.32 (4)C31—H310.9300
C1B—C61.42 (3)C32—H320.9300
C2A—C3A1.405 (8)C34—H340.9300
C2B—C3B1.44 (4)C35—C401.423 (3)
C3A—C4A1.340 (9)C35—C361.346 (3)
C3B—C4B1.32 (4)C36—C371.411 (3)
C4A—C5A1.461 (8)C37—C381.336 (3)
C4B—C5B1.45 (2)C38—C391.476 (3)
C7—C81.474 (3)C41—C421.479 (3)
C8—C91.425 (3)C42—C431.420 (3)
C8—C171.382 (2)C42—C511.377 (2)
C9—C101.365 (3)C43—C441.362 (3)
C10—C111.398 (3)C44—C451.406 (3)
C11—C161.418 (3)C45—C501.417 (3)
C11—C121.417 (3)C45—C461.419 (3)
C12—C131.351 (4)C46—C471.349 (3)
C13—C141.391 (4)C47—C481.389 (3)
C14—C151.355 (3)C48—C491.362 (3)
C15—C161.412 (3)C49—C501.415 (3)
C16—C171.401 (3)C50—C511.402 (3)
C2A—H2A0.9300C36—H360.9300
C2B—H2B0.9300C37—H370.9300
C3A—H3A0.9300C39—H39A0.9600
C3B—H3B0.9300C39—H39B0.9600
C5A—H5B0.9600C39—H39C0.9600
C5A—H5A0.9600C40—H400.9300
C5A—H5C0.9600C44—H440.9300
C5B—H5D0.9600C46—H460.9300
C5B—H5E0.9600C47—H470.9300
C5B—H5F0.9600C48—H480.9300
C6—H60.9300C49—H490.9300
C10—H100.9300C51—H510.9300
C1A—O1A—C4A107.6 (5)N3—C23—C18124.41 (18)
C1B—O1B—C4B109.4 (19)O5—C24—C25121.60 (17)
C9—O3—H3O109.00O5—C24—N4120.42 (17)
C18—O4—C21106.72 (16)N4—C24—C25117.98 (16)
C26—O6—H6O109.00C24—C25—C26119.01 (16)
C35—O7—C38106.53 (15)C26—C25—C34117.86 (16)
C43—O9—H9O109.00C24—C25—C34123.13 (16)
N2—N1—C6114.76 (16)C25—C26—C27119.91 (17)
N1—N2—C7118.84 (15)O6—C26—C27117.64 (18)
C7—N2—H2N121.00O6—C26—C25122.46 (17)
N1—N2—H2N121.00C26—C27—C28122.19 (18)
N4—N3—C23113.59 (15)C29—C28—C33117.99 (18)
N3—N4—C24119.83 (15)C27—C28—C29123.13 (18)
C24—N4—H4N120.00C27—C28—C33118.88 (17)
N3—N4—H4N120.00C28—C29—C30120.89 (19)
N6—N5—C40114.51 (15)C29—C30—C31121.2 (2)
N5—N6—C41119.07 (14)C30—C31—C32119.6 (2)
N5—N6—H6N120.00C31—C32—C33121.08 (18)
C41—N6—H6N120.00C28—C33—C32119.25 (16)
C2A—C1A—C6135.8 (5)C28—C33—C34118.02 (17)
O1A—C1A—C6114.8 (4)C32—C33—C34122.73 (16)
O1A—C1A—C2A109.3 (5)C25—C34—C33123.12 (16)
C2B—C1B—C6138 (2)C18—C19—H19126.00
O1B—C1B—C6114 (2)C20—C19—H19126.00
O1B—C1B—C2B108 (2)C19—C20—H20126.00
C1A—C2A—C3A107.2 (5)C21—C20—H20126.00
C1B—C2B—C3B107 (2)H22A—C22—H22C109.00
C2A—C3A—C4A107.5 (5)C21—C22—H22A110.00
C2B—C3B—C4B108 (3)C21—C22—H22B109.00
C3A—C4A—C5A135.6 (7)H22A—C22—H22B109.00
O1A—C4A—C3A108.3 (6)H22B—C22—H22C109.00
O1A—C4A—C5A116.0 (6)C21—C22—H22C110.00
C3B—C4B—C5B136 (2)N3—C23—H23118.00
O1B—C4B—C5B116.6 (18)C18—C23—H23118.00
O1B—C4B—C3B107 (2)C26—C27—H27119.00
N1—C6—C1B130.3 (9)C28—C27—H27119.00
N1—C6—C1A116.7 (2)C28—C29—H29120.00
N2—C7—C8117.68 (16)C30—C29—H29120.00
O2—C7—N2121.55 (17)C29—C30—H30119.00
O2—C7—C8120.73 (17)C31—C30—H30119.00
C9—C8—C17118.17 (16)C32—C31—H31120.00
C7—C8—C9119.94 (16)C30—C31—H31120.00
C7—C8—C17121.53 (17)C33—C32—H32119.00
O3—C9—C10118.59 (19)C31—C32—H32119.00
O3—C9—C8120.92 (18)C25—C34—H34118.00
C8—C9—C10120.49 (18)C33—C34—H34118.00
C9—C10—C11121.44 (19)O7—C35—C40120.29 (17)
C12—C11—C16117.87 (18)C36—C35—C40130.21 (18)
C10—C11—C12123.03 (19)O7—C35—C36109.49 (18)
C10—C11—C16119.08 (18)C35—C36—C37107.10 (19)
C11—C12—C13120.6 (2)C36—C37—C38107.2 (2)
C12—C13—C14121.5 (2)O7—C38—C37109.63 (19)
C13—C14—C15120.1 (2)O7—C38—C39116.42 (18)
C14—C15—C16120.5 (2)C37—C38—C39133.9 (2)
C11—C16—C17118.68 (16)N5—C40—C35122.94 (18)
C11—C16—C15119.50 (17)N6—C41—C42117.24 (15)
C15—C16—C17121.81 (18)O8—C41—N6121.25 (18)
C8—C17—C16122.13 (17)O8—C41—C42121.51 (17)
C3A—C2A—H2A126.00C41—C42—C43119.03 (15)
C1A—C2A—H2A126.00C41—C42—C51122.69 (16)
C3B—C2B—H2B127.00C43—C42—C51118.25 (17)
C1B—C2B—H2B126.00C42—C43—C44120.47 (17)
C2A—C3A—H3A126.00O9—C43—C42121.35 (18)
C4A—C3A—H3A126.00O9—C43—C44118.18 (18)
C2B—C3B—H3B126.00C43—C44—C45121.56 (19)
C4B—C3B—H3B126.00C44—C45—C46123.23 (19)
C4A—C5A—H5C109.00C44—C45—C50118.78 (18)
H5B—C5A—H5C110.00C46—C45—C50117.97 (17)
H5A—C5A—H5C109.00C45—C46—C47121.1 (2)
C4A—C5A—H5A109.00C46—C47—C48121.1 (2)
H5A—C5A—H5B109.00C47—C48—C49120.0 (2)
C4A—C5A—H5B109.00C48—C49—C50120.8 (2)
C4B—C5B—H5E110.00C45—C50—C49118.96 (18)
H5D—C5B—H5E110.00C45—C50—C51118.52 (16)
C4B—C5B—H5D110.00C49—C50—C51122.52 (18)
H5E—C5B—H5F109.00C42—C51—C50122.39 (17)
C4B—C5B—H5F109.00C35—C36—H36126.00
H5D—C5B—H5F109.00C37—C36—H36126.00
C1A—C6—H6122.00C36—C37—H37126.00
N1—C6—H6122.00C38—C37—H37126.00
C1B—C6—H6108.00C38—C39—H39A109.00
C11—C10—H10119.00C38—C39—H39B109.00
C9—C10—H10119.00C38—C39—H39C109.00
C13—C12—H12120.00H39A—C39—H39B109.00
C11—C12—H12120.00H39A—C39—H39C109.00
C14—C13—H13119.00H39B—C39—H39C110.00
C12—C13—H13119.00N5—C40—H40119.00
C15—C14—H14120.00C35—C40—H40119.00
C13—C14—H14120.00C43—C44—H44119.00
C14—C15—H15120.00C45—C44—H44119.00
C16—C15—H15120.00C45—C46—H46119.00
C8—C17—H17119.00C47—C46—H46119.00
C16—C17—H17119.00C46—C47—H47119.00
O4—C18—C23120.66 (17)C48—C47—H47119.00
C19—C18—C23130.56 (19)C47—C48—H48120.00
O4—C18—C19108.63 (18)C49—C48—H48120.00
C18—C19—C20107.7 (2)C48—C49—H49120.00
C19—C20—C21107.2 (2)C50—C49—H49120.00
O4—C21—C22116.5 (2)C42—C51—H51119.00
O4—C21—C20109.8 (2)C50—C51—H51119.00
C20—C21—C22133.7 (2)
C4A—O1A—C1A—C2A0.9 (7)C19—C20—C21—O4−0.9 (3)
C4A—O1A—C1A—C6177.9 (5)C19—C20—C21—C22177.8 (3)
C1A—O1A—C4A—C3A−0.3 (7)N4—C24—C25—C3413.2 (3)
C1A—O1A—C4A—C5A176.8 (5)O5—C24—C25—C2613.1 (3)
C21—O4—C18—C19−0.5 (2)O5—C24—C25—C34−167.32 (19)
C21—O4—C18—C23175.60 (19)N4—C24—C25—C26−166.32 (17)
C18—O4—C21—C200.9 (2)C24—C25—C26—C27178.46 (18)
C18—O4—C21—C22−178.1 (2)C34—C25—C26—O6179.23 (18)
C35—O7—C38—C37−0.9 (2)C34—C25—C26—C27−1.1 (3)
C35—O7—C38—C39177.11 (18)C24—C25—C34—C33−179.04 (18)
C38—O7—C35—C360.2 (2)C26—C25—C34—C330.5 (3)
C38—O7—C35—C40179.94 (18)C24—C25—C26—O6−1.2 (3)
N2—N1—C6—C1A174.2 (3)O6—C26—C27—C28−179.11 (19)
C6—N1—N2—C7−179.29 (17)C25—C26—C27—C281.2 (3)
N1—N2—C7—C8167.77 (15)C26—C27—C28—C29179.2 (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—C300.2 (3)
N3—N4—C24—O55.5 (3)C27—C28—C33—C32−179.56 (19)
N3—N4—C24—C25−175.01 (16)C27—C28—C33—C340.0 (3)
C40—N5—N6—C41−177.91 (17)C29—C28—C33—C320.6 (3)
N6—N5—C40—C35178.16 (17)C29—C28—C33—C34−179.85 (18)
N5—N6—C41—O80.9 (3)C28—C29—C30—C31−0.7 (3)
N5—N6—C41—C42−179.52 (15)C29—C30—C31—C320.4 (3)
O1A—C1A—C2A—C3A−1.1 (6)C30—C31—C32—C330.4 (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—C34179.6 (2)
O1A—C1A—C6—N1174.2 (4)C28—C33—C34—C250.0 (3)
C1A—C2A—C3A—C4A0.9 (7)C32—C33—C34—C25179.59 (19)
C2A—C3A—C4A—C5A−176.6 (7)O7—C35—C36—C370.5 (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—N5170.0 (2)
N2—C7—C8—C9164.73 (17)C35—C36—C37—C38−1.0 (3)
O2—C7—C8—C17155.33 (18)C36—C37—C38—O71.2 (2)
C7—C8—C9—O3−5.2 (3)C36—C37—C38—C39−176.3 (2)
C7—C8—C9—C10174.57 (18)O8—C41—C42—C4317.5 (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—C101.4 (3)N6—C41—C42—C5120.0 (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—C44179.53 (17)
O3—C9—C10—C11178.38 (19)C51—C42—C43—O9177.80 (17)
C9—C10—C11—C12−177.7 (2)C51—C42—C43—C44−2.5 (3)
C9—C10—C11—C160.7 (3)C41—C42—C51—C50179.96 (17)
C12—C11—C16—C17178.51 (18)C43—C42—C51—C502.0 (3)
C10—C11—C16—C15−178.63 (19)O9—C43—C44—C45−178.71 (18)
C10—C11—C16—C170.0 (3)C42—C43—C44—C451.5 (3)
C12—C11—C16—C15−0.2 (3)C43—C44—C45—C46177.9 (2)
C16—C11—C12—C130.1 (3)C43—C44—C45—C50−0.1 (3)
C10—C11—C12—C13178.5 (2)C44—C45—C46—C47−177.8 (2)
C11—C12—C13—C140.1 (4)C50—C45—C46—C470.2 (3)
C12—C13—C14—C15−0.3 (4)C44—C45—C50—C49178.90 (18)
C13—C14—C15—C160.2 (4)C44—C45—C50—C51−0.3 (3)
C14—C15—C16—C17−178.6 (2)C46—C45—C50—C490.8 (3)
C14—C15—C16—C110.0 (3)C46—C45—C50—C51−178.44 (18)
C11—C16—C17—C80.0 (3)C45—C46—C47—C48−1.1 (4)
C15—C16—C17—C8178.60 (18)C46—C47—C48—C490.9 (4)
C23—C18—C19—C20−175.6 (2)C47—C48—C49—C500.1 (3)
O4—C18—C23—N39.4 (3)C48—C49—C50—C45−1.0 (3)
O4—C18—C19—C20−0.1 (2)C48—C49—C50—C51178.27 (19)
C19—C18—C23—N3−175.5 (2)C45—C50—C51—C42−0.7 (3)
C18—C19—C20—C210.6 (3)C49—C50—C51—C42−179.87 (18)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2N···O8i0.862.152.869 (2)142
N4—H4N···O20.862.202.896 (2)137
N6—H6N···O5ii0.862.363.074 (2)140
N6—H6N···N3ii0.862.443.212 (2)149
O3—H3O···O20.821.892.612 (3)145
O6—H6O···O50.821.892.603 (2)145
O9—H9O···O80.821.862.588 (2)147
C34—H34···O20.932.483.398 (3)167
C40—H40···O5ii0.932.423.185 (3)140
C44—H44···O1A0.932.593.514 (5)176
C48—H48···O3ii0.932.513.149 (3)126

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5157).

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