Nafimidone monohydrate: an imidazole anticonvulsant

Hempel, A.; Camerman, N.; Camerman, A.; Mastropaolo, D.

doi:10.1107/S1600536805011487

Nafimidone monohydrate: an imidazole anticonvulsant

A. Hempel, N. Camerman, A. Camerman and D. Mastropaolo

In the crystal structure of 2-(1H-imidazol-1-yl)-1-(2-naphthyl)ethanone monohydrate, C₁₅H₁₂N₂O·H₂O, the naphthalene and imidazole rings are essentially planar and the angle between their planes is 77.05 (11)°. The water molecule connects two nafimidone molecules through O—H

N and O—H

O hydrogen bonds [H

N 1.83 (5) and H

O = 2.14 (6) Å], creating centrosymmetric dimer clusters. Weak non-standard hydrogen bonds of the type C—H

O [H

O 2.53–2.60 Å] also contribute to the crystal packing.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805011487/lh6406sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805011487/lh6406Isup2.hkl Contains datablock I

CCDC reference: 272044

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.004 Å
R factor = 0.055
wR factor = 0.174
Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      65.00 Deg.

Author Response: ...'see _exptl_special_details'


Alert level C
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5878
PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6].....      65.00 Deg.
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O19    -   H192   ...       1.03 Ang.

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

   0 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
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: Picker Operating Manual (Picker, 1967); cell refinement: Picker Operating Manual; data reduction: DATRDN in the XRAY System (Stewart, 1978); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELX97.

2-(1H-imidazol-1-yl)-1-(2-naphthyl)ethanone monohydrate top

Crystal data top

C₁₅H₁₂N₂O·H₂O	F(000) = 536
M_r = 254.28	D_x = 1.309 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 11.597 (3) Å	Cell parameters from 32 reflections
b = 14.213 (3) Å	θ = 28–49°
c = 7.827 (2) Å	µ = 0.72 mm⁻¹
β = 90.15 (2)°	T = 294 K
V = 1290.1 (5) Å³	Needle, colorless
Z = 4	0.47 × 0.10 × 0.06 mm

Data collection top

Picker FACS-1 four-circle diffractometer	1328 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.008
Ni-filtered radiation monochromator	θ_max = 65.0°, θ_min = 3.8°
θ/2θ scans	h = 0→13
Absorption correction: ψ scan (North et al., 1968)	k = −16→0
T_min = 0.911, T_max = 0.961	l = −9→9
2310 measured reflections	3 standard reflections every 100 reflections
2197 independent reflections	intensity decay: 0.9%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.174	w = 1/[σ²(F_o²) + (0.0477P)²] where P = (F_o² + 2F_c²)/3
S = 0.92	(Δ/σ)_max < 0.001
2197 reflections	Δρ_max = 0.17 e Å⁻³
181 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0035 (8)

Special details top

Experimental. PICKER FACS-1 mechanical limit does not allow for data collection above θ = 65°. Data were collected on a crystal with dimensions 0.47 x 0.10 x 0.06 mm mounted along its long axis.

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.4132 (2)	0.62187 (19)	−0.0803 (3)	0.0556 (7)
H1	0.3480	0.6143	−0.1485	0.080 (3)*
C2	0.4002 (2)	0.64163 (19)	0.0896 (3)	0.0548 (7)
C3	0.4995 (3)	0.6556 (2)	0.1930 (4)	0.0609 (8)
H3	0.4911	0.6706	0.3080	0.080 (3)*
C4	0.6067 (2)	0.6473 (2)	0.1250 (4)	0.0622 (8)
H4	0.6709	0.6556	0.1948	0.080 (3)*
C5	0.7327 (3)	0.6173 (2)	−0.1247 (4)	0.0705 (9)
H5	0.7984	0.6249	−0.0577	0.080 (3)*
C6	0.7436 (3)	0.5977 (2)	−0.2936 (4)	0.0742 (9)
H6	0.8167	0.5929	−0.3413	0.080 (3)*
C7	0.6461 (3)	0.5847 (2)	−0.3969 (4)	0.0735 (9)
H7	0.6548	0.5712	−0.5125	0.080 (3)*
C8	0.5390 (3)	0.5918 (2)	−0.3286 (4)	0.0657 (8)
H8	0.4747	0.5828	−0.3979	0.080 (3)*
C9	0.5239 (2)	0.61274 (18)	−0.1542 (3)	0.0529 (7)
C10	0.6224 (2)	0.62625 (19)	−0.0492 (4)	0.0564 (7)
N11	0.0735 (2)	0.64095 (18)	0.1539 (3)	0.0608 (7)
C12	0.0173 (3)	0.5630 (2)	0.2030 (4)	0.0737 (9)
H12	0.0403	0.5025	0.1734	0.080 (3)*
N13	−0.0729 (2)	0.5812 (2)	0.2969 (4)	0.0777 (8)
C14	−0.0748 (3)	0.6760 (3)	0.3081 (4)	0.0735 (9)
H14	−0.1300	0.7102	0.3677	0.080 (3)*
C15	0.0137 (3)	0.7145 (2)	0.2218 (4)	0.0689 (9)
H15	0.0306	0.7781	0.2108	0.080 (3)*
C16	0.2854 (2)	0.64984 (19)	0.1712 (3)	0.0556 (7)
C17	0.1795 (3)	0.6448 (3)	0.0574 (4)	0.0720 (9)
H17A	0.1779	0.6995	−0.0166	0.080 (3)*
H17B	0.1847	0.5893	−0.0145	0.080 (3)*
O18	0.27471 (18)	0.66121 (15)	0.3234 (2)	0.0735 (7)
O19	0.1823 (3)	0.5938 (2)	0.6438 (3)	0.0899 (9)
H191	0.196 (5)	0.608 (4)	0.550 (7)	0.161 (15)*
H192	0.148 (4)	0.527 (4)	0.644 (6)	0.161 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0561 (17)	0.0543 (17)	0.0563 (16)	−0.0026 (13)	−0.0003 (13)	0.0029 (12)
C2	0.0562 (17)	0.0543 (16)	0.0538 (16)	−0.0064 (13)	0.0042 (13)	0.0037 (12)
C3	0.0630 (18)	0.0660 (19)	0.0538 (16)	−0.0038 (15)	−0.0024 (13)	−0.0035 (14)
C4	0.0497 (17)	0.075 (2)	0.0621 (17)	−0.0041 (14)	−0.0036 (13)	0.0017 (15)
C5	0.0562 (18)	0.080 (2)	0.075 (2)	−0.0006 (16)	0.0016 (15)	0.0101 (16)
C6	0.071 (2)	0.078 (2)	0.074 (2)	0.0057 (17)	0.0225 (17)	0.0112 (17)
C7	0.076 (2)	0.087 (2)	0.0576 (18)	0.0083 (18)	0.0121 (17)	−0.0004 (15)
C8	0.0650 (19)	0.075 (2)	0.0573 (17)	0.0005 (15)	0.0075 (15)	−0.0032 (14)
C9	0.0538 (16)	0.0498 (16)	0.0551 (16)	−0.0036 (12)	0.0030 (13)	0.0029 (11)
C10	0.0560 (17)	0.0540 (16)	0.0592 (16)	−0.0054 (13)	0.0038 (13)	0.0071 (13)
N11	0.0522 (14)	0.0758 (17)	0.0543 (14)	0.0006 (12)	0.0057 (11)	−0.0020 (12)
C12	0.062 (2)	0.069 (2)	0.090 (2)	0.0033 (17)	0.0062 (18)	0.0025 (18)
N13	0.0606 (17)	0.083 (2)	0.089 (2)	−0.0008 (15)	0.0150 (14)	0.0070 (15)
C14	0.0598 (19)	0.087 (2)	0.073 (2)	0.0096 (18)	0.0079 (16)	−0.0027 (18)
C15	0.068 (2)	0.066 (2)	0.073 (2)	0.0049 (16)	0.0059 (16)	−0.0014 (15)
C16	0.0585 (17)	0.0568 (18)	0.0514 (16)	−0.0047 (13)	0.0088 (13)	−0.0015 (13)
C17	0.0577 (18)	0.099 (3)	0.0593 (17)	0.0001 (17)	0.0093 (14)	−0.0019 (16)
O18	0.0743 (14)	0.0938 (17)	0.0524 (12)	−0.0030 (12)	0.0075 (10)	−0.0040 (11)
O19	0.108 (2)	0.095 (2)	0.0672 (15)	−0.0197 (16)	0.0179 (14)	−0.0077 (13)

Geometric parameters (Å, º) top

C1—C2	1.367 (4)	C9—C10	1.418 (4)
C1—C9	1.416 (4)	N11—C12	1.342 (4)
C1—H1	0.9300	N11—C15	1.363 (4)
C2—C3	1.420 (4)	N11—C17	1.446 (3)
C2—C16	1.482 (4)	C12—N13	1.307 (4)
C3—C4	1.359 (4)	C12—H12	0.9300
C3—H3	0.9300	N13—C14	1.351 (4)
C4—C10	1.408 (4)	C14—C15	1.346 (4)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.357 (4)	C15—H15	0.9300
C5—C10	1.416 (4)	C16—O18	1.209 (3)
C5—H5	0.9300	C16—O18	1.209 (3)
C6—C7	1.401 (5)	C16—C17	1.517 (4)
C6—H6	0.9300	C17—H17A	0.9700
C7—C8	1.358 (4)	C17—H17B	0.9700
C7—H7	0.9300	O19—H191	0.78 (6)
C8—C9	1.408 (4)	O19—H192	1.02 (5)
C8—H8	0.9300

C2—C1—C9	121.2 (3)	C4—C10—C9	118.9 (3)
C2—C1—H1	119.4	C5—C10—C9	118.3 (3)
C9—C1—H1	119.4	C12—N11—C15	105.9 (3)
C1—C2—C3	119.4 (3)	C12—N11—C17	126.5 (3)
C1—C2—C16	122.4 (3)	C15—N11—C17	127.5 (3)
C3—C2—C16	118.1 (2)	N13—C12—N11	112.9 (3)
C4—C3—C2	120.4 (3)	N13—C12—H12	123.6
C4—C3—H3	119.8	N11—C12—H12	123.6
C2—C3—H3	119.8	C12—N13—C14	104.3 (3)
C3—C4—C10	121.3 (3)	C15—C14—N13	111.1 (3)
C3—C4—H4	119.4	C15—C14—H14	124.4
C10—C4—H4	119.4	N13—C14—H14	124.4
C6—C5—C10	120.7 (3)	C14—C15—N11	105.9 (3)
C6—C5—H5	119.6	C14—C15—H15	127.1
C10—C5—H5	119.6	N11—C15—H15	127.1
C5—C6—C7	120.8 (3)	O18—C16—C2	122.0 (3)
C5—C6—H6	119.6	O18—C16—C2	122.0 (3)
C7—C6—H6	119.6	O18—C16—C17	120.0 (3)
C8—C7—C6	120.0 (3)	O18—C16—C17	120.0 (3)
C8—C7—H7	120.0	C2—C16—C17	118.0 (2)
C6—C7—H7	120.0	N11—C17—C16	112.6 (2)
C7—C8—C9	120.9 (3)	N11—C17—H17A	109.1
C7—C8—H8	119.5	C16—C17—H17A	109.1
C9—C8—H8	119.5	N11—C17—H17B	109.1
C8—C9—C1	122.0 (3)	C16—C17—H17B	109.1
C8—C9—C10	119.2 (3)	H17A—C17—H17B	107.8
C1—C9—C10	118.8 (2)	H191—O19—H192	109 (5)
C4—C10—C5	122.8 (3)

C9—C1—C2—C3	1.6 (4)	C15—N11—C12—N13	−0.2 (4)
C9—C1—C2—C16	−178.8 (3)	C17—N11—C12—N13	176.5 (3)
C1—C2—C3—C4	−1.6 (4)	N11—C12—N13—C14	0.1 (4)
C16—C2—C3—C4	178.9 (3)	C12—N13—C14—C15	−0.1 (4)
C2—C3—C4—C10	1.1 (4)	N13—C14—C15—N11	0.0 (4)
C10—C5—C6—C7	−0.8 (5)	C12—N11—C15—C14	0.1 (3)
C5—C6—C7—C8	0.2 (5)	C17—N11—C15—C14	−176.5 (3)
C6—C7—C8—C9	0.3 (5)	C1—C2—C16—O18	175.1 (3)
C7—C8—C9—C1	179.1 (3)	C3—C2—C16—O18	−5.4 (4)
C7—C8—C9—C10	−0.1 (4)	C1—C2—C16—O18	175.1 (3)
C2—C1—C9—C8	179.6 (3)	C3—C2—C16—O18	−5.4 (4)
C2—C1—C9—C10	−1.2 (4)	C1—C2—C16—C17	−5.7 (4)
C3—C4—C10—C5	179.8 (3)	C3—C2—C16—C17	173.9 (3)
C3—C4—C10—C9	−0.7 (4)	C12—N11—C17—C16	−92.7 (4)
C6—C5—C10—C4	−179.5 (3)	C15—N11—C17—C16	83.2 (4)
C6—C5—C10—C9	1.0 (4)	O18—C16—C17—N11	−8.5 (4)
C8—C9—C10—C4	179.9 (3)	O18—C16—C17—N11	−8.5 (4)
C1—C9—C10—C4	0.7 (4)	C2—C16—C17—N11	172.2 (3)
C8—C9—C10—C5	−0.5 (4)	C2—C16—O18—O18	0.0 (17)
C1—C9—C10—C5	−179.8 (3)	C17—C16—O18—O18	0.0 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O19—H191···O18	0.78 (6)	2.13 (6)	2.893 (3)	165 (6)
O19—H192···N13ⁱ	1.02 (5)	1.83 (5)	2.830 (4)	164 (4)
C1—H1···O19ⁱⁱ	0.93	2.53	3.458 (4)	175
C15—H15···O19ⁱⁱⁱ	0.93	2.59	3.411 (5)	148
C17—H17A···O18ⁱⁱⁱ	0.97	2.60	3.491 (4)	153

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y, z−1; (iii) x, −y+3/2, z−1/2.

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