6-Chloro-N′-(2-hydr­oxy-1-naphthyl­methyl­ene)nicotinohydrazide

The title compound, C₁₇H₁₂ClN₃O₂, was synthesized by the Schiff base condensation reaction of 2-hydr­oxy-1-naphthaldehyde with 6-chloro­nicotinic acid hydrazide in a methanol solution. The mol­ecule displays a trans configuration with respect to the C=N and C—N bonds. The dihedral angle between the naphthyl ring system and the pyridine ring is 7.6 (4)°. There is an intra­molecular O—H...N hydrogen bond. The crystal structure is stabilized by inter­molecular N—H...O and C—H...O hydrogen bonds, forming chains running along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.056
• wR factor = 0.109
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.49
           From the CIF: _reflns_number_total               2980
           Count of symmetry unique reflns         1533
           Completeness (_total/calc)            194.39%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1447
           Fraction of Friedel pairs measured     0.944
           Are heavy atom types Z>Si present        yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Schiff base compounds have been widely investigated over a century (Fan et al., 2007; Kim et al., 2005; Nimitsiriwat et al., 2004). Some of the compounds have been found to have pharmacological and antibacterial activity (Chen et al., 1997; Ren et al., 2002). In this paper, the crystal structure of a new Schiff base compound derived from the condensation reaction of 2-hydroxy-1-naphthaldehyde with 6-chloronicotinic acid hydrazide is reported.

The Schiff base molecule of the compound displays a trans configuration with respect to the C?N and C—N bonds (Fig. 1). The dihedral angle between the C8—C17 naphthyl ring and the C1—C5/N1 pyridine ring is 7.6 (4)°. All the bond lengths are within normal ranges (Allen et al., 1987). There is an intramolecular O–H···N hydrogen bond in the molecule (Table 1). The crystal structure is stabilized by intermolecular N–H···O and C–H···O hydrogen bonds (Table 1), forming chains running along the b axis (Fig. 2).

Related literature

For related literature, see: Allen et al. (1987); Chen et al. (1997); Fan et al. (2007); Kim et al. (2005); Nimitsiriwat et al. (2004); Ren et al. (2002).

S2. Experimental

2-Hydroxy-1-naphthaldehyde (0.1 mmol, 17.2 mg) and 6-chloronicotinic acid hydrazide (0.1 mmol, 17.1 mg) were dissolved in a methanol solution (10 ml). The mixture was stirred at room temperature to give a clear yellow solution. Crystals of the title compound were formed by gradual evaporation of the solvent for two days at room temperature.

S3. Refinement

Atom H2B was located from a difference Fourier map and refined isotropically, with N–H distance restrained to 0.90 (1) Å. Other H atoms were constrained to ideal geometries, with C–H = 0.93 Å, O–H = 0.82 Å, and with U_iso(H) set to 1.2U_eq(C) and 1.5U_eq(O).

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures

	Fig. 1. The structure of (I) at the 30% probability level.
	Fig. 2. Molecular packing of (I), viewed along the a axis. Intermolecular hydrogen bonds are shown as dashed lines.

6-Chloro-N'-(2-hydroxy-1-naphthylmethylene)nicotinohydrazide

Crystal data

C17H12ClN3O2	F(000) = 336
Mr = 325.75	Dx = 1.466 Mg m^−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
a = 4.7450 (9) Å	Cell parameters from 790 reflections
b = 6.0420 (12) Å	θ = 2.4–24.3°
c = 25.752 (5) Å	µ = 0.27 mm^−1
β = 91.93 (3)°	T = 293 K
V = 737.9 (2) Å^3	Block, yellow
Z = 2	0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2980 independent reflections
Radiation source: fine-focus sealed tube	1948 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
ω scan	θmax = 26.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→5
Tmin = 0.937, Tmax = 0.940	k = −7→7
5692 measured reflections	l = −32→32

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0375P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max < 0.001
2980 reflections	Δρmax = 0.15 e Å^−3
212 parameters	Δρmin = −0.18 e Å^−3
3 restraints	Absolute structure: Flack (1983), 1447 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.11 (10)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.0611 (3)	1.5001 (2)	−0.11216 (6)	0.0788 (4)
O1	−0.4774 (5)	0.7030 (4)	0.02688 (11)	0.0494 (7)
O2	−0.3951 (6)	0.1598 (5)	0.10628 (11)	0.0515 (7)
H2	−0.3567	0.2788	0.0929	0.077*
N1	−0.2165 (8)	1.1504 (6)	−0.08492 (13)	0.0577 (10)
N2	−0.0394 (6)	0.6927 (6)	0.06381 (12)	0.0380 (8)
N3	−0.1179 (6)	0.5186 (5)	0.09455 (13)	0.0416 (8)
C1	−0.0145 (9)	1.2884 (7)	−0.06934 (16)	0.0484 (11)
C2	0.1344 (8)	1.2758 (6)	−0.02279 (15)	0.0472 (10)
H2A	0.2741	1.3785	−0.0141	0.057*
C3	0.0704 (8)	1.1058 (6)	0.01076 (16)	0.0390 (9)
H3	0.1677	1.0913	0.0425	0.047*
C4	−0.1420 (8)	0.9566 (6)	−0.00370 (16)	0.0375 (10)
C5	−0.2731 (9)	0.9895 (7)	−0.05108 (17)	0.0525 (12)
H5	−0.4155	0.8905	−0.0608	0.063*
C6	−0.2328 (8)	0.7734 (6)	0.02998 (14)	0.0367 (9)
C7	0.0501 (10)	0.4617 (6)	0.13256 (18)	0.0401 (9)
H7	0.2148	0.5417	0.1391	0.048*
C8	−0.0149 (7)	0.2745 (6)	0.16510 (15)	0.0376 (9)
C9	−0.2276 (8)	0.1283 (7)	0.14941 (16)	0.0432 (10)
C10	−0.2774 (9)	−0.0650 (7)	0.17726 (19)	0.0555 (13)
H10	−0.4147	−0.1643	0.1654	0.067*
C11	−0.1272 (9)	−0.1079 (7)	0.22124 (18)	0.0569 (13)
H11	−0.1638	−0.2377	0.2392	0.068*
C12	0.0845 (9)	0.0363 (7)	0.24135 (17)	0.0485 (12)
C13	0.2286 (11)	−0.0050 (10)	0.28798 (17)	0.0631 (15)
H13	0.1877	−0.1323	0.3066	0.076*
C14	0.4314 (10)	0.1389 (9)	0.30741 (18)	0.0651 (14)
H14	0.5319	0.1062	0.3381	0.078*
C15	0.4840 (9)	0.3345 (8)	0.28043 (16)	0.0596 (13)
H15	0.6164	0.4348	0.2938	0.072*
C16	0.3413 (8)	0.3798 (7)	0.23432 (15)	0.0460 (10)
H16	0.3789	0.5106	0.2168	0.055*
C17	0.1391 (8)	0.2315 (7)	0.21308 (15)	0.0384 (10)
H2B	0.142 (3)	0.733 (7)	0.0613 (17)	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1123 (10)	0.0589 (7)	0.0659 (7)	−0.0054 (7)	0.0137 (6)	0.0212 (6)
O1	0.0287 (14)	0.0529 (18)	0.0662 (19)	−0.0089 (14)	−0.0033 (13)	0.0008 (15)
O2	0.0416 (15)	0.057 (2)	0.0557 (18)	−0.0132 (14)	0.0021 (14)	−0.0051 (15)
N1	0.073 (3)	0.055 (3)	0.044 (2)	−0.001 (2)	−0.005 (2)	0.0076 (19)
N2	0.0300 (17)	0.0427 (19)	0.0414 (18)	−0.0028 (15)	0.0004 (16)	0.0072 (16)
N3	0.040 (2)	0.041 (2)	0.0444 (19)	−0.0037 (17)	0.0083 (16)	0.0022 (17)
C1	0.059 (3)	0.043 (3)	0.044 (3)	−0.002 (2)	0.010 (2)	0.005 (2)
C2	0.046 (2)	0.042 (3)	0.053 (3)	−0.006 (2)	0.004 (2)	−0.005 (2)
C3	0.037 (2)	0.040 (2)	0.040 (2)	−0.004 (2)	−0.0024 (18)	0.000 (2)
C4	0.036 (2)	0.041 (3)	0.036 (2)	0.0013 (19)	0.0026 (18)	−0.0020 (19)
C5	0.048 (3)	0.053 (3)	0.056 (3)	−0.007 (2)	−0.001 (2)	−0.011 (2)
C6	0.033 (2)	0.039 (2)	0.038 (2)	−0.0016 (19)	0.0035 (18)	−0.0067 (18)
C7	0.035 (2)	0.041 (2)	0.045 (2)	0.000 (2)	0.0052 (17)	0.003 (2)
C8	0.033 (2)	0.035 (2)	0.045 (2)	−0.0019 (18)	0.0092 (18)	−0.0023 (18)
C9	0.038 (2)	0.045 (3)	0.047 (3)	0.002 (2)	0.006 (2)	−0.002 (2)
C10	0.055 (3)	0.042 (3)	0.071 (3)	−0.014 (2)	0.019 (3)	−0.010 (3)
C11	0.063 (3)	0.041 (3)	0.068 (3)	−0.007 (2)	0.016 (3)	0.007 (2)
C12	0.056 (3)	0.037 (3)	0.053 (3)	0.007 (2)	0.016 (2)	0.006 (2)
C13	0.076 (4)	0.071 (4)	0.043 (3)	0.016 (3)	0.014 (3)	0.022 (3)
C14	0.068 (3)	0.088 (4)	0.040 (3)	0.028 (3)	0.006 (2)	0.010 (3)
C15	0.066 (3)	0.065 (3)	0.047 (3)	0.005 (3)	−0.002 (2)	0.002 (2)
C16	0.043 (3)	0.046 (3)	0.049 (3)	−0.003 (2)	0.002 (2)	0.003 (2)
C17	0.038 (2)	0.039 (3)	0.038 (2)	0.0033 (19)	0.0086 (19)	−0.0006 (19)

Geometric parameters (Å, º)

Cl1—C1	1.734 (4)	C7—H7	0.9300
O1—C6	1.236 (4)	C8—C9	1.391 (5)
O2—C9	1.357 (4)	C8—C17	1.438 (5)
O2—H2	0.8200	C9—C10	1.395 (6)
N1—C1	1.323 (5)	C10—C11	1.343 (6)
N1—C5	1.339 (5)	C10—H10	0.9300
N2—C6	1.336 (4)	C11—C12	1.415 (6)
N2—N3	1.375 (4)	C11—H11	0.9300
N2—H2B	0.900 (10)	C12—C13	1.385 (6)
N3—C7	1.288 (5)	C12—C17	1.414 (5)
C1—C2	1.373 (5)	C13—C14	1.378 (7)
C2—C3	1.382 (5)	C13—H13	0.9300
C2—H2A	0.9300	C14—C15	1.398 (6)
C3—C4	1.393 (5)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.374 (5)
C4—C5	1.365 (5)	C15—H15	0.9300
C4—C6	1.479 (5)	C16—C17	1.410 (5)
C5—H5	0.9300	C16—H16	0.9300
C7—C8	1.447 (5)
C9—O2—H2	109.5	C17—C8—C7	121.8 (4)
C1—N1—C5	114.8 (4)	O2—C9—C8	123.2 (4)
C6—N2—N3	117.5 (3)	O2—C9—C10	115.7 (4)
C6—N2—H2B	120 (3)	C8—C9—C10	121.1 (4)
N3—N2—H2B	122 (3)	C11—C10—C9	120.1 (4)
C7—N3—N2	118.0 (3)	C11—C10—H10	120.0
N1—C1—C2	125.2 (4)	C9—C10—H10	120.0
N1—C1—Cl1	115.8 (3)	C10—C11—C12	122.7 (4)
C2—C1—Cl1	119.0 (3)	C10—C11—H11	118.7
C1—C2—C3	118.0 (4)	C12—C11—H11	118.7
C1—C2—H2A	121.0	C13—C12—C17	120.2 (4)
C3—C2—H2A	121.0	C13—C12—C11	122.0 (4)
C2—C3—C4	119.0 (4)	C17—C12—C11	117.7 (4)
C2—C3—H3	120.5	C14—C13—C12	121.3 (5)
C4—C3—H3	120.5	C14—C13—H13	119.3
C5—C4—C3	116.7 (4)	C12—C13—H13	119.3
C5—C4—C6	120.0 (4)	C13—C14—C15	119.1 (5)
C3—C4—C6	123.3 (4)	C13—C14—H14	120.4
N1—C5—C4	126.3 (4)	C15—C14—H14	120.4
N1—C5—H5	116.9	C16—C15—C14	120.4 (5)
C4—C5—H5	116.9	C16—C15—H15	119.8
O1—C6—N2	122.6 (3)	C14—C15—H15	119.8
O1—C6—C4	120.7 (4)	C15—C16—C17	121.2 (4)
N2—C6—C4	116.6 (3)	C15—C16—H16	119.4
N3—C7—C8	120.7 (4)	C17—C16—H16	119.4
N3—C7—H7	119.7	C16—C17—C12	117.7 (4)
C8—C7—H7	119.7	C16—C17—C8	122.6 (3)
C9—C8—C17	118.5 (3)	C12—C17—C8	119.8 (4)
C9—C8—C7	119.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N3	0.82	1.84	2.559 (4)	146
N2—H2B···O1^i	0.90 (1)	2.05 (2)	2.862 (4)	150 (4)
C2—H2A···O1^ii	0.93	2.50	3.396 (4)	161

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