3-Chloro-N′-hydr­oxy-N-(1-naphth­yl)benzene­carboximidamide

The mol­ecule of the title compound, C₁₇H₁₃ClN₂O, adopts a cis configuration with respect to the C=N bond. The crystal structure features O—H...N hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.110
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?

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

   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).

3-Chloro-N'-hydroxy-N-(1-naphthyl)benzenecarboximidamide

Crystal data

C17H13ClN2O	V = 747.41 (7) Å^3
Mr = 296.74	Z = 2
Triclinic, P1	Dx = 1.319 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7217 (5) Å	Cell parameters from 85 reflections
b = 8.7039 (4) Å	θ = 4.9–21.5°
c = 11.9158 (4) Å	µ = 0.26 mm^−1
α = 104.099 (3)°	T = 298 K
β = 93.815 (4)°	Block, orange
γ = 103.869 (4)°	0.52 × 0.30 × 0.20 mm

Data collection

Bruker–Nonius KappaCCD diffractometer	Rint = 0.046
Radiation source: fine-focus sealed tube	θmax = 25.5°, θmin = 4.5°
φ and ω scans	h = −9→9
10909 measured reflections	k = −9→10
2764 independent reflections	l = −13→14
1796 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0431P)^2 + 0.1831P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
2764 reflections	Δρmax = 0.13 e Å^−3
190 parameters	Δρmin = −0.32 e Å^−3
0 restraints

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	1.09774 (11)	−0.22768 (10)	0.53081 (6)	0.0899 (3)
C17	0.4906 (3)	0.3541 (2)	0.83830 (16)	0.0428 (5)
C8	0.6410 (3)	0.2882 (2)	0.81859 (16)	0.0395 (5)
N2	0.6596 (2)	0.1654 (2)	0.87420 (14)	0.0484 (4)
O1	0.8583 (2)	0.1113 (2)	1.03249 (12)	0.0691 (5)
C7	0.7685 (3)	0.0629 (2)	0.84256 (16)	0.0408 (5)
C6	0.9170 (3)	−0.0693 (2)	0.68356 (17)	0.0452 (5)
N1	0.8650 (3)	0.0228 (2)	0.91684 (14)	0.0520 (5)
C5	0.7659 (3)	−0.0230 (2)	0.71904 (16)	0.0397 (5)
C16	0.3566 (3)	0.2966 (3)	0.9034 (2)	0.0567 (6)
C9	0.7651 (3)	0.3469 (2)	0.75335 (17)	0.0475 (5)
C4	0.6109 (3)	−0.0666 (2)	0.63978 (18)	0.0493 (5)
C12	0.4788 (3)	0.4863 (3)	0.79062 (19)	0.0553 (6)
C11	0.6098 (4)	0.5424 (3)	0.7234 (2)	0.0688 (7)
C3	0.6095 (3)	−0.1587 (3)	0.5274 (2)	0.0631 (7)
C1	0.9108 (3)	−0.1633 (3)	0.57183 (18)	0.0533 (6)
C2	0.7574 (4)	−0.2085 (3)	0.49319 (19)	0.0658 (7)
C15	0.2198 (3)	0.3699 (3)	0.9236 (2)	0.0769 (8)
C13	0.3334 (4)	0.5569 (3)	0.8139 (3)	0.0776 (8)
C10	0.7475 (4)	0.4738 (3)	0.7043 (2)	0.0639 (6)
C14	0.2090 (4)	0.5012 (4)	0.8784 (3)	0.0855 (10)
H2N	0.6615	0.2043	0.9560	0.058*
H1O	0.9478	0.0969	1.0751	0.083*
H6	1.0228	−0.0369	0.7353	0.054*
H16	0.3611	0.2079	0.9330	0.068*
H9	0.8626	0.3024	0.7411	0.057*
H4	0.4960	−0.0293	0.6669	0.059*
H11	0.6014	0.6283	0.6916	0.083*
H3	0.5061	−0.1874	0.4740	0.076*
H2	0.7541	−0.2721	0.4177	0.079*
H15	0.1330	0.3319	0.9680	0.092*
H13	0.3238	0.6440	0.7838	0.093*
H10	0.8317	0.5111	0.6581	0.077*
H14	0.1153	0.5503	0.8929	0.103*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0982 (6)	0.0961 (6)	0.0831 (5)	0.0450 (4)	0.0404 (4)	0.0117 (4)
C17	0.0418 (11)	0.0362 (11)	0.0439 (11)	0.0147 (9)	−0.0079 (9)	−0.0021 (9)
C8	0.0452 (11)	0.0340 (10)	0.0384 (10)	0.0147 (9)	−0.0036 (9)	0.0066 (8)
N2	0.0649 (12)	0.0520 (11)	0.0423 (9)	0.0353 (9)	0.0105 (8)	0.0181 (8)
O1	0.1089 (13)	0.0822 (11)	0.0346 (8)	0.0652 (10)	0.0037 (8)	0.0118 (7)
C7	0.0499 (12)	0.0374 (11)	0.0407 (11)	0.0191 (9)	0.0033 (9)	0.0140 (8)
C6	0.0544 (13)	0.0430 (12)	0.0402 (11)	0.0163 (10)	0.0020 (9)	0.0126 (9)
N1	0.0770 (13)	0.0548 (11)	0.0339 (9)	0.0381 (10)	0.0025 (8)	0.0109 (8)
C5	0.0504 (12)	0.0344 (10)	0.0377 (11)	0.0160 (9)	−0.0006 (9)	0.0128 (8)
C16	0.0489 (13)	0.0495 (13)	0.0654 (14)	0.0173 (11)	0.0030 (11)	0.0003 (11)
C9	0.0494 (12)	0.0404 (12)	0.0527 (12)	0.0148 (10)	0.0035 (10)	0.0105 (10)
C4	0.0546 (13)	0.0424 (12)	0.0509 (13)	0.0157 (10)	−0.0088 (10)	0.0141 (10)
C12	0.0627 (15)	0.0373 (12)	0.0596 (14)	0.0232 (11)	−0.0188 (11)	−0.0015 (10)
C11	0.100 (2)	0.0386 (13)	0.0716 (16)	0.0241 (14)	−0.0042 (15)	0.0212 (12)
C3	0.0756 (17)	0.0515 (14)	0.0536 (15)	0.0145 (13)	−0.0219 (12)	0.0088 (11)
C1	0.0709 (15)	0.0475 (13)	0.0456 (13)	0.0219 (11)	0.0125 (11)	0.0130 (10)
C2	0.098 (2)	0.0535 (14)	0.0391 (13)	0.0195 (14)	−0.0017 (13)	0.0037 (10)
C15	0.0461 (14)	0.0744 (19)	0.0897 (19)	0.0164 (13)	0.0051 (13)	−0.0155 (15)
C13	0.080 (2)	0.0568 (16)	0.090 (2)	0.0420 (15)	−0.0246 (16)	−0.0042 (14)
C10	0.0844 (18)	0.0439 (13)	0.0660 (16)	0.0147 (13)	0.0134 (13)	0.0212 (11)
C14	0.0546 (17)	0.072 (2)	0.109 (2)	0.0385 (15)	−0.0215 (16)	−0.0262 (17)

Geometric parameters (Å, º)

Cl1—C1	1.728 (2)	C11—C10	1.345 (3)
C17—C16	1.404 (3)	C3—C2	1.368 (3)
C17—C12	1.420 (3)	C1—C2	1.373 (3)
C17—C8	1.423 (3)	C15—C14	1.394 (4)
C8—C9	1.357 (3)	C13—C14	1.344 (4)
C8—N2	1.417 (2)	N2—H2N	0.9483
N2—C7	1.372 (2)	O1—H1O	0.8813
O1—N1	1.416 (2)	C6—H6	0.930
C7—N1	1.283 (2)	C16—H16	0.930
C7—C5	1.476 (3)	C9—H9	0.930
C6—C1	1.373 (3)	C4—H4	1.0590
C6—C5	1.382 (3)	C11—H11	0.930
C5—C4	1.388 (3)	C3—H3	0.930
C16—C15	1.365 (3)	C2—H2	0.930
C9—C10	1.399 (3)	C15—H15	0.930
C4—C3	1.381 (3)	C13—H13	0.930
C12—C11	1.402 (3)	C10—H10	0.930
C12—C13	1.416 (3)	C14—H14	0.930
C16—C17—C12	119.12 (19)	C14—C13—C12	121.6 (3)
C16—C17—C8	123.28 (19)	C11—C10—C9	120.6 (2)
C12—C17—C8	117.6 (2)	C13—C14—C15	120.2 (2)
C9—C8—N2	121.88 (17)	C7—N2—H2N	114.2
C9—C8—C17	120.77 (18)	C8—N2—H2N	110.4
N2—C8—C17	117.28 (17)	N1—O1—H1O	105.0
C7—N2—C8	123.85 (17)	C1—C6—H6	120.0
N1—C7—N2	123.14 (17)	C5—C6—H6	120.0
N1—C7—C5	115.47 (16)	C15—C16—H16	119.8
N2—C7—C5	121.07 (16)	C17—C16—H16	119.8
C1—C6—C5	119.9 (2)	C8—C9—H9	119.7
C7—N1—O1	111.18 (15)	C10—C9—H9	119.7
C6—C5—C4	119.55 (18)	C3—C4—H4	121.5
C6—C5—C7	119.36 (17)	C5—C4—H4	119.3
C4—C5—C7	120.97 (19)	C10—C11—H11	119.5
C15—C16—C17	120.4 (2)	C12—C11—H11	119.5
C8—C9—C10	120.5 (2)	C2—C3—H3	119.4
C3—C4—C5	119.2 (2)	C4—C3—H3	119.4
C11—C12—C13	122.5 (2)	C3—C2—H2	120.4
C11—C12—C17	119.6 (2)	C1—C2—H2	120.4
C13—C12—C17	117.9 (3)	C16—C15—H15	119.7
C10—C11—C12	120.9 (2)	C14—C15—H15	119.7
C2—C3—C4	121.2 (2)	C14—C13—H13	119.2
C2—C1—C6	120.9 (2)	C12—C13—H13	119.2
C2—C1—Cl1	119.76 (18)	C11—C10—H10	119.7
C6—C1—Cl1	119.35 (18)	C9—C10—H10	119.7
C3—C2—C1	119.1 (2)	C13—C14—H14	119.9
C16—C15—C14	120.7 (3)	C15—C14—H14	119.9

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1^i	0.88	1.98	2.768 (2)	147

Symmetry code: (i) −x+2, −y, −z+2.