1-[(4-Formyl­phen­yl)hydrazono]naphthalen-2(1H)-one–2-naphthol (1/1)

The crystal structure of the title compound, C₁₇H₁₂N₂O₂·C₁₀H₈O, shows that the mol­ecules are effectively planar in the solid state and the compound exists in the hydrazone form and not the azo form. The hydrazone H atom and carbonyl O atom are linked by an intra­molecular N—H...O hydrogen bond. The 2-naphthol molecules are disordered over inversion centres, the asymmetric unit containing half each of two such molecules. The packing can be described as a polymeric arrangement of mol­ecules linked through O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.055
• wR factor = 0.191
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.29
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.59
PLAT301_ALERT_3_C Main Residue  Disorder .........................       4.00 Perc.
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........         O3
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........         O4
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C18    -   C19    ...       1.35 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C23    -   C24    ...       1.34 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C24    -   C25    ...       1.39 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       2.90 Deg.
              O3   -C19  -H19A    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       4.00 Deg.
              O4   -C24  -H24A    1.555   1.555   1.555

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

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

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Computing details

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

1-[(4-formylphenyl)hydrazono]naphthalen-2(1H)-one–2-naphthol (1/1)

Crystal data

C17H12N2O2·C10H8O	Z = 2
Mr = 420.45	F(000) = 440
Triclinic, P1	Dx = 1.346 Mg m^−3
Hall symbol: -P 1	Melting point: 410(1) K
a = 7.9088 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.7469 (16) Å	Cell parameters from 1881 reflections
c = 12.3067 (19) Å	θ = 2.6–26.2°
α = 86.421 (3)°	µ = 0.09 mm^−1
β = 89.184 (3)°	T = 293 K
γ = 83.715 (3)°	Block, red
V = 1037.7 (3) Å^3	0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4168 independent reflections
Radiation source: fine-focus sealed tube	2436 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
φ and ω scans	θmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −9→9
Tmin = 0.976, Tmax = 0.984	k = −9→13
5880 measured reflections	l = −15→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.055	w = 1/[σ^2(Fo^2) + (0.0904P)^2 + 0.3211P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.191	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.59 e Å^−3
4168 reflections	Δρmin = −0.26 e Å^−3
303 parameters

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 > 2σ(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	Occ. (<1)
N1	0.3434 (2)	0.50515 (19)	0.40980 (15)	0.0479 (5)
N2	0.2751 (2)	0.6010 (2)	0.46135 (16)	0.0519 (5)
H2	0.289 (4)	0.679 (3)	0.432 (2)	0.080 (9)*
O1	0.4007 (3)	0.7432 (2)	0.31120 (18)	0.0900 (7)
O2	−0.1270 (3)	0.4370 (2)	0.89404 (16)	0.0832 (7)
C1	0.4294 (3)	0.5225 (2)	0.31792 (18)	0.0487 (6)
C2	0.4554 (3)	0.6449 (3)	0.2673 (2)	0.0619 (7)
C3	0.5456 (3)	0.6480 (3)	0.1647 (2)	0.0687 (8)
H3	0.5602	0.7250	0.1291	0.082*
C4	0.6087 (3)	0.5428 (3)	0.1198 (2)	0.0639 (7)
H4	0.6672	0.5492	0.0540	0.077*
C5	0.5904 (3)	0.4204 (3)	0.16836 (19)	0.0547 (6)
C6	0.4992 (3)	0.4093 (2)	0.26695 (18)	0.0490 (6)
C7	0.4819 (3)	0.2895 (3)	0.3130 (2)	0.0585 (7)
H7	0.4202	0.2804	0.3774	0.070*
C8	0.5547 (4)	0.1847 (3)	0.2648 (2)	0.0683 (8)
H8	0.5426	0.1056	0.2972	0.082*
C9	0.6462 (4)	0.1955 (3)	0.1681 (2)	0.0723 (8)
H9	0.6962	0.1242	0.1362	0.087*
C10	0.6622 (3)	0.3119 (3)	0.1202 (2)	0.0675 (8)
H10	0.7215	0.3192	0.0547	0.081*
C11	0.1791 (3)	0.5810 (2)	0.55579 (17)	0.0441 (5)
C12	0.1043 (3)	0.6856 (2)	0.6061 (2)	0.0545 (6)
H12	0.1177	0.7657	0.5767	0.065*
C13	0.0101 (3)	0.6699 (2)	0.6999 (2)	0.0545 (6)
H13	−0.0408	0.7398	0.7334	0.065*
C14	−0.0096 (3)	0.5509 (2)	0.74492 (18)	0.0463 (5)
C15	0.0644 (3)	0.4473 (2)	0.69288 (18)	0.0478 (6)
H15	0.0501	0.3673	0.7222	0.057*
C16	0.1580 (3)	0.4607 (2)	0.59915 (18)	0.0467 (5)
H16	0.2068	0.3905	0.5650	0.056*
C17	−0.1049 (3)	0.5354 (3)	0.8472 (2)	0.0601 (7)
H17	−0.1523	0.6079	0.8784	0.072*
C18	0.8446 (4)	1.0972 (2)	0.9089 (2)	0.0607 (7)
H18	0.8291	1.1773	0.8748	0.073*
C19	0.7280 (4)	1.0168 (3)	0.8958 (2)	0.0648 (7)
H19A	0.6347	1.0409	0.8512	0.078*	0.50
C20	0.7468 (4)	0.8965 (3)	0.9492 (2)	0.0721 (8)
H20	0.6640	0.8427	0.9413	0.087*
C21	0.8847 (4)	0.8580 (3)	1.0125 (2)	0.0668 (7)
H21	0.8959	0.7779	1.0467	0.080*
C22	1.0103 (3)	0.9384 (2)	1.02654 (18)	0.0546 (6)
O3	0.6013 (5)	1.0485 (3)	0.8288 (3)	0.0664 (10)	0.50
H3A	0.6182	1.1126	0.7926	0.100*	0.50
O4	0.7492 (9)	0.8641 (6)	0.3000 (6)	0.141 (2)	0.50
H4A	0.6483	0.8444	0.3073	0.169*	0.50
C23	0.9748 (6)	0.9409 (3)	0.3636 (3)	0.0955 (12)
H23	1.0344	0.9309	0.2985	0.115*
C24	0.8175 (7)	0.9060 (4)	0.3755 (4)	0.1079 (14)
H24A	0.7727	0.8713	0.3163	0.130*	0.50
C25	0.7151 (6)	0.9168 (3)	0.4678 (4)	0.1136 (15)
H25	0.6064	0.8913	0.4718	0.136*
C26	0.7874 (5)	0.9682 (3)	0.5524 (3)	0.0974 (12)
H26	0.7243	0.9779	0.6163	0.117*
C27	0.9516 (5)	1.0071 (3)	0.5482 (3)	0.0807 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0424 (10)	0.0612 (12)	0.0385 (10)	−0.0022 (9)	−0.0002 (8)	0.0039 (9)
N2	0.0495 (12)	0.0551 (13)	0.0477 (12)	0.0018 (10)	0.0053 (9)	0.0104 (10)
O1	0.1070 (17)	0.0630 (13)	0.0897 (15)	0.0148 (11)	0.0387 (13)	0.0247 (11)
O2	0.0990 (16)	0.0822 (15)	0.0661 (13)	−0.0109 (12)	0.0289 (11)	0.0085 (11)
C1	0.0388 (12)	0.0658 (15)	0.0394 (12)	−0.0034 (11)	−0.0018 (10)	0.0104 (11)
C2	0.0534 (15)	0.0688 (18)	0.0572 (15)	0.0085 (13)	0.0043 (12)	0.0176 (13)
C3	0.0612 (16)	0.0805 (19)	0.0590 (16)	−0.0029 (14)	0.0075 (13)	0.0288 (14)
C4	0.0529 (15)	0.095 (2)	0.0418 (13)	−0.0086 (14)	0.0057 (11)	0.0127 (14)
C5	0.0455 (13)	0.0816 (18)	0.0378 (12)	−0.0136 (12)	−0.0005 (10)	0.0013 (12)
C6	0.0400 (12)	0.0685 (16)	0.0385 (12)	−0.0087 (11)	−0.0012 (9)	0.0012 (11)
C7	0.0592 (15)	0.0709 (17)	0.0470 (14)	−0.0158 (13)	0.0100 (11)	−0.0046 (12)
C8	0.0750 (19)	0.0698 (18)	0.0640 (17)	−0.0221 (15)	0.0123 (14)	−0.0125 (14)
C9	0.0739 (19)	0.084 (2)	0.0642 (18)	−0.0232 (16)	0.0152 (15)	−0.0245 (16)
C10	0.0606 (16)	0.100 (2)	0.0455 (14)	−0.0187 (16)	0.0105 (12)	−0.0157 (15)
C11	0.0389 (11)	0.0515 (13)	0.0400 (12)	−0.0007 (10)	−0.0028 (9)	0.0055 (10)
C12	0.0541 (14)	0.0473 (13)	0.0588 (15)	0.0016 (11)	0.0030 (12)	0.0091 (11)
C13	0.0547 (14)	0.0493 (14)	0.0568 (15)	0.0059 (11)	0.0046 (11)	−0.0039 (11)
C14	0.0410 (12)	0.0529 (13)	0.0444 (12)	−0.0033 (10)	0.0004 (10)	−0.0022 (10)
C15	0.0501 (13)	0.0463 (13)	0.0466 (13)	−0.0070 (10)	0.0004 (10)	0.0031 (10)
C16	0.0464 (13)	0.0493 (13)	0.0436 (12)	−0.0013 (10)	0.0004 (10)	−0.0035 (10)
C17	0.0594 (16)	0.0675 (17)	0.0527 (15)	−0.0046 (13)	0.0078 (12)	−0.0051 (13)
C18	0.0785 (18)	0.0528 (15)	0.0472 (14)	0.0084 (14)	0.0002 (13)	−0.0010 (11)
C19	0.0748 (19)	0.0624 (17)	0.0533 (15)	0.0098 (15)	−0.0036 (14)	−0.0035 (12)
C20	0.079 (2)	0.0670 (18)	0.0705 (18)	−0.0088 (15)	−0.0030 (16)	−0.0034 (14)
C21	0.083 (2)	0.0530 (15)	0.0632 (17)	−0.0054 (14)	−0.0009 (15)	0.0034 (12)
C22	0.0698 (16)	0.0516 (14)	0.0387 (12)	0.0080 (12)	0.0112 (11)	−0.0035 (10)
O3	0.068 (2)	0.054 (2)	0.077 (3)	−0.0092 (17)	−0.013 (2)	0.0060 (18)
O4	0.155 (6)	0.108 (5)	0.158 (6)	−0.006 (4)	0.028 (5)	−0.008 (4)
C23	0.120 (3)	0.070 (2)	0.088 (3)	0.016 (2)	0.045 (2)	0.0081 (18)
C24	0.138 (4)	0.068 (2)	0.114 (4)	0.007 (2)	−0.004 (3)	−0.001 (2)
C25	0.147 (4)	0.070 (2)	0.111 (3)	0.028 (2)	0.043 (3)	0.019 (2)
C26	0.105 (3)	0.075 (2)	0.102 (3)	0.018 (2)	0.054 (2)	0.018 (2)
C27	0.104 (3)	0.0472 (15)	0.081 (2)	0.0203 (15)	0.0468 (19)	0.0170 (15)

Geometric parameters (Å, º)

N1—N2	1.306 (3)	C15—C16	1.370 (3)
N1—C1	1.325 (3)	C15—H15	0.9300
N2—C11	1.397 (3)	C16—H16	0.9300
N2—H2	0.91 (3)	C17—H17	0.9300
O1—C2	1.250 (3)	C18—C19	1.349 (4)
O2—C17	1.200 (3)	C18—C22^i	1.410 (4)
C1—C2	1.454 (4)	C18—H18	0.9300
C1—C6	1.455 (3)	C19—O3	1.309 (4)
C2—C3	1.441 (4)	C19—C20	1.407 (4)
C3—C4	1.334 (4)	C19—H19A	0.9300
C3—H3	0.9300	C20—C21	1.361 (4)
C4—C5	1.431 (4)	C20—H20	0.9300
C4—H4	0.9300	C21—C22	1.405 (4)
C5—C10	1.402 (4)	C21—H21	0.9300
C5—C6	1.408 (3)	C22—C18^i	1.410 (4)
C6—C7	1.394 (4)	C22—C22^i	1.433 (5)
C7—C8	1.372 (4)	O3—H3A	0.8200
C7—H7	0.9300	O4—C24	1.215 (7)
C8—C9	1.390 (4)	O4—H4A	0.8500
C8—H8	0.9300	C23—C24	1.342 (6)
C9—C10	1.367 (4)	C23—C27^ii	1.412 (5)
C9—H9	0.9300	C23—H23	0.9300
C10—H10	0.9300	C24—C25	1.390 (6)
C11—C12	1.388 (3)	C24—H24A	0.9300
C11—C16	1.394 (3)	C25—C26	1.369 (6)
C12—C13	1.376 (3)	C25—H25	0.9300
C12—H12	0.9300	C26—C27	1.407 (5)
C13—C14	1.385 (3)	C26—H26	0.9300
C13—H13	0.9300	C27—C27^ii	1.411 (6)
C14—C15	1.388 (3)	C27—C23^ii	1.412 (5)
C14—C17	1.468 (3)
N2—N1—C1	120.5 (2)	C16—C15—H15	119.3
N1—N2—C11	119.7 (2)	C14—C15—H15	119.3
N1—N2—H2	118.0 (19)	C15—C16—C11	119.0 (2)
C11—N2—H2	122.2 (19)	C15—C16—H16	120.5
N1—C1—C2	124.2 (2)	C11—C16—H16	120.5
N1—C1—C6	115.9 (2)	O2—C17—C14	125.6 (3)
C2—C1—C6	119.9 (2)	O2—C17—H17	117.2
O1—C2—C3	121.6 (3)	C14—C17—H17	117.2
O1—C2—C1	120.9 (2)	C19—C18—C22^i	120.9 (2)
C3—C2—C1	117.5 (3)	C19—C18—H18	119.5
C4—C3—C2	121.4 (3)	C22^i—C18—H18	119.5
C4—C3—H3	119.3	O3—C19—C18	119.8 (3)
C2—C3—H3	119.3	O3—C19—C20	119.8 (3)
C3—C4—C5	123.0 (2)	C18—C19—C20	120.4 (3)
C3—C4—H4	118.5	O3—C19—H19A	2.9
C5—C4—H4	118.5	C18—C19—H19A	119.8
C10—C5—C6	119.5 (3)	C20—C19—H19A	119.8
C10—C5—C4	121.4 (2)	C21—C20—C19	120.8 (3)
C6—C5—C4	119.1 (2)	C21—C20—H20	119.6
C7—C6—C5	118.4 (2)	C19—C20—H20	119.6
C7—C6—C1	122.5 (2)	C20—C21—C22	120.5 (3)
C5—C6—C1	119.1 (2)	C20—C21—H21	119.8
C8—C7—C6	121.0 (2)	C22—C21—H21	119.8
C8—C7—H7	119.5	C21—C22—C18^i	122.5 (2)
C6—C7—H7	119.5	C21—C22—C22^i	118.7 (3)
C7—C8—C9	120.7 (3)	C18^i—C22—C22^i	118.7 (3)
C7—C8—H8	119.7	C19—O3—H3A	109.5
C9—C8—H8	119.7	C24—O4—H4A	119.9
C10—C9—C8	119.5 (3)	C24—C23—C27^ii	118.9 (4)
C10—C9—H9	120.3	C24—C23—H23	120.6
C8—C9—H9	120.3	C27^ii—C23—H23	120.6
C9—C10—C5	120.9 (2)	O4—C24—C23	120.3 (6)
C9—C10—H10	119.5	O4—C24—C25	113.5 (6)
C5—C10—H10	119.5	C23—C24—C25	126.2 (5)
C12—C11—C16	120.4 (2)	O4—C24—H24A	4.0
C12—C11—N2	117.8 (2)	C23—C24—H24A	116.9
C16—C11—N2	121.8 (2)	C25—C24—H24A	116.9
C13—C12—C11	119.6 (2)	C26—C25—C24	114.4 (5)
C13—C12—H12	120.2	C26—C25—H25	122.8
C11—C12—H12	120.2	C24—C25—H25	122.8
C12—C13—C14	120.7 (2)	C25—C26—C27	123.7 (4)
C12—C13—H13	119.7	C25—C26—H26	118.1
C14—C13—H13	119.7	C27—C26—H26	118.1
C13—C14—C15	119.0 (2)	C26—C27—C27^ii	118.7 (5)
C13—C14—C17	120.2 (2)	C26—C27—C23^ii	123.2 (3)
C15—C14—C17	120.8 (2)	C27^ii—C27—C23^ii	118.2 (5)
C16—C15—C14	121.3 (2)
C1—N1—N2—C11	177.44 (19)	N1—N2—C11—C16	2.0 (3)
N2—N1—C1—C2	0.0 (3)	C16—C11—C12—C13	0.6 (3)
N2—N1—C1—C6	−179.60 (19)	N2—C11—C12—C13	−179.4 (2)
N1—C1—C2—O1	2.4 (4)	C11—C12—C13—C14	0.5 (4)
C6—C1—C2—O1	−178.0 (2)	C12—C13—C14—C15	−1.2 (4)
N1—C1—C2—C3	−177.3 (2)	C12—C13—C14—C17	177.7 (2)
C6—C1—C2—C3	2.3 (3)	C13—C14—C15—C16	0.9 (3)
O1—C2—C3—C4	177.8 (3)	C17—C14—C15—C16	−178.0 (2)
C1—C2—C3—C4	−2.5 (4)	C14—C15—C16—C11	0.1 (3)
C2—C3—C4—C5	0.8 (4)	C12—C11—C16—C15	−0.8 (3)
C3—C4—C5—C10	−178.3 (3)	N2—C11—C16—C15	179.1 (2)
C3—C4—C5—C6	1.2 (4)	C13—C14—C17—O2	−178.6 (3)
C10—C5—C6—C7	−0.7 (3)	C15—C14—C17—O2	0.3 (4)
C4—C5—C6—C7	179.8 (2)	C22^i—C18—C19—O3	−174.7 (3)
C10—C5—C6—C1	178.2 (2)	C22^i—C18—C19—C20	1.9 (4)
C4—C5—C6—C1	−1.3 (3)	O3—C19—C20—C21	174.8 (3)
N1—C1—C6—C7	−1.9 (3)	C18—C19—C20—C21	−1.8 (4)
C2—C1—C6—C7	178.4 (2)	C19—C20—C21—C22	0.7 (4)
N1—C1—C6—C5	179.23 (19)	C20—C21—C22—C18^i	−179.9 (3)
C2—C1—C6—C5	−0.4 (3)	C20—C21—C22—C22^i	0.3 (4)
C5—C6—C7—C8	1.2 (4)	C27^ii—C23—C24—O4	178.0 (5)
C1—C6—C7—C8	−177.6 (2)	C27^ii—C23—C24—C25	0.6 (6)
C6—C7—C8—C9	−0.6 (4)	O4—C24—C25—C26	−177.7 (5)
C7—C8—C9—C10	−0.7 (4)	C23—C24—C25—C26	−0.1 (6)
C8—C9—C10—C5	1.3 (4)	C24—C25—C26—C27	−0.2 (5)
C6—C5—C10—C9	−0.6 (4)	C25—C26—C27—C27^ii	0.1 (5)
C4—C5—C10—C9	179.0 (3)	C25—C26—C27—C23^ii	−179.6 (3)
N1—N2—C11—C12	−178.04 (19)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.91 (3)	1.86 (3)	2.582 (3)	135 (3)
O3—H3A···O1^iii	0.82	1.94	2.737 (4)	164
O4—H4A···O1	0.85	2.34	3.171 (8)	166

Symmetry code: (iii) −x+1, −y+2, −z+1.