A monoamine oxidase B inhibitor: N-(2-amino­eth­yl)-p-chloro­benzamide (Ro16-6491) hydro­chloride

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

doi:10.1107/S1600536805019008

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A monoamine oxidase B inhibitor: N-(2-aminoethyl)-p-chlorobenzamide (Ro16-6491) hydrochloride

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

In the title compound, 2-(4-chlorobenzamido)ethanaminium chloride, C₉H₁₂ClN₂O⁺·Cl⁻, both independent cations have linearly extended conformations, with protonation occurring at the terminal N atom. The interplanar angles between the chlorobenzoyl rings and the planar amide groups are 137.6 (3) and 149.3 (5)° for cations A and B, respectively. The cations are N—H

O hydrogen-bonded in a head-to-head/tail-to-tail fashion, producing distinct hydrophobic and hydrophilic layers running parallel to [110]. The Cl⁻ anions are hydrogen-bonded to the terminal positively charged –NH₃⁺ groups. Weak C—H

Cl⁻ interactions further coordinate the Cl⁻ anions. Structural comparison with pargyline, an irreversible MAO-B inhibitor, is presented.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805019008/lh6450sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805019008/lh6450Isup2.hkl Contains datablock I

CCDC reference: 277726

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.017 Å
R factor = 0.076
wR factor = 0.206
Data-to-parameter ratio = 9.3

checkCIF/PLATON results

No syntax errors found



Alert level A
REFLT03_ALERT_3_A  Reflection count < 85% complete (theta max?)
           From the CIF: _diffrn_reflns_theta_max           64.99
           From the CIF: _diffrn_reflns_theta_full          64.99
           From the CIF: _reflns_number_total               2386
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         3879
           Completeness (_total/calc)             61.51%

Author Response: ...'see _exptl_special_details item'


PLAT022_ALERT_3_A Ratio Unique / Expected Reflections too Low ....       0.62

Author Response: ...'see _exptl_special_details item'

PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      64.99 Deg.

Author Response: ...'see _exptl_special_details item'

PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.62

Author Response: ...'see _exptl_special_details item'


Alert level B
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         17

Alert level C
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 10 for a
            centrosymmetric structure
            sine(theta)/lambda                0.5878
            Proportion of unique data used    1.0000
            Ratio reflections to parameters   9.2840
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].....      64.99 Deg.
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.28
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C2A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C2B
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          4
              Cl

   4 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   7 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   9 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: Picker Manual (Picker, 1967); cell refinement: Picker Manual; data reduction: DATRDN (Stewart, 1976); 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: SHELXL97.

2-(4-chlorobenzamido)ethanaminium chloride top

Crystal data top

C₉H₁₂ClN₂O⁺·Cl⁻	Z = 4
M_r = 235.11	F(000) = 488
Triclinic, P1	D_x = 1.363 Mg m⁻³
a = 6.726 (2) Å	Cu Kα radiation, λ = 1.54178 Å
b = 6.837 (2) Å	Cell parameters from 32 reflections
c = 25.267 (5) Å	θ = 19–37°
α = 83.57 (2)°	µ = 4.87 mm⁻¹
β = 83.03 (2)°	T = 294 K
γ = 88.03 (2)°	Prism, colorless
V = 1145.8 (5) Å³	0.29 × 0.17 × 0.15 mm

Data collection top

Picker FACS-1 four-circle diffractometer	1613 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.019
Ni filtered radiation monochromator	θ_max = 65.0°, θ_min = 1.8°
ω/2θ scans	h = 0→7
Absorption correction: ψ scan (North et al., 1968)	k = −8→8
T_min = 0.423, T_max = 0.480	l = −29→29
2628 measured reflections	3 standard reflections every 100 reflections
2386 independent reflections	intensity decay: 3.9%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.206	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0929P)² + 2.1584P] where P = (F_o² + 2F_c²)/3
2386 reflections	(Δ/σ)_max < 0.001
257 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Special details top

Experimental. Generally no observable reflections above θ = 55° due to poor quality and small size of the crystal and high anisotropic thermal displacement parameters. A number of visible reflections from the region θ = 55–65° were identified from a previous data set collected on a larger but much poorer quality crystal and duly collected. These measures were exercised to prolong the life of our only copper X-ray tube for the Picker diffractometer. There were no other plausible reasons for the checkCIF red A alerts beyond the above.

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
Cl2A	0.2515 (4)	1.0501 (3)	0.44186 (9)	0.0558 (8)
Cl1A	0.7836 (6)	0.4496 (5)	0.04422 (12)	0.1192 (13)
C2A	0.6343 (19)	0.4776 (15)	0.1027 (5)	0.069 (3)
C3A	0.433 (2)	0.5181 (15)	0.1017 (4)	0.079 (3)
H3A	0.3784	0.5298	0.0693	0.077 (7)*
C4A	0.3109 (15)	0.5411 (15)	0.1490 (4)	0.066 (3)
H4A	0.1746	0.5677	0.1483	0.077 (7)*
C5A	0.3912 (16)	0.5248 (12)	0.1968 (4)	0.047 (3)
C6A	0.5887 (18)	0.4833 (14)	0.1986 (4)	0.060 (3)
H6A	0.6429	0.4715	0.2310	0.077 (7)*
C7A	0.7092 (16)	0.4585 (14)	0.1506 (5)	0.070 (3)
H7A	0.8446	0.4280	0.1515	0.077 (7)*
C8A	0.2567 (18)	0.5495 (14)	0.2468 (5)	0.052 (3)
O9A	0.0859 (11)	0.4764 (9)	0.2567 (3)	0.076 (2)
N10A	0.3271 (12)	0.6529 (11)	0.2823 (4)	0.054 (3)
H10A	0.4434	0.7037	0.2738	0.077 (7)*
C11A	0.2214 (14)	0.6843 (12)	0.3338 (4)	0.048 (3)
H11A	0.0808	0.6559	0.3343	0.060 (7)*
H11B	0.2314	0.8210	0.3399	0.060 (7)*
C12A	0.3083 (14)	0.5537 (13)	0.3773 (4)	0.054 (3)
H12A	0.2886	0.4173	0.3724	0.060 (7)*
H12B	0.4514	0.5742	0.3743	0.060 (7)*
N13A	0.2173 (11)	0.5906 (10)	0.4318 (3)	0.059 (2)
H13A	0.2336	0.7159	0.4365	0.077 (7)*
H13B	0.2766	0.5128	0.4562	0.077 (7)*
H13C	0.0872	0.5652	0.4355	0.077 (7)*
Cl2B	−0.2498 (4)	0.5455 (3)	0.44286 (9)	0.0577 (8)
Cl1B	0.2670 (8)	0.0090 (6)	0.03904 (15)	0.1515 (18)
C2B	0.128 (3)	0.0053 (18)	0.1026 (5)	0.083 (4)
C3B	−0.063 (3)	−0.0490 (16)	0.1084 (5)	0.092 (5)
H3B	−0.1237	−0.0830	0.0795	0.077 (7)*
C4B	−0.1671 (18)	−0.0521 (14)	0.1587 (4)	0.074 (3)
H4B	−0.2994	−0.0921	0.1634	0.077 (7)*
C5B	−0.0872 (19)	0.0006 (14)	0.2033 (5)	0.057 (3)
C6B	0.1142 (17)	0.0489 (12)	0.1937 (4)	0.059 (3)
H6B	0.1772	0.0807	0.2223	0.077 (7)*
C7B	0.2276 (17)	0.0523 (14)	0.1432 (4)	0.074 (3)
H7B	0.3623	0.0846	0.1378	0.077 (7)*
C8B	−0.2082 (19)	0.0094 (17)	0.2554 (5)	0.054 (3)
O9B	−0.3527 (11)	−0.0968 (12)	0.2687 (3)	0.093 (3)
N10B	−0.1594 (12)	0.1447 (10)	0.2848 (3)	0.048 (2)
H10B	−0.0594	0.2185	0.2727	0.077 (7)*
C11B	−0.2678 (15)	0.1735 (13)	0.3367 (4)	0.050 (3)
H11C	−0.4081	0.1457	0.3365	0.060 (7)*
H11D	−0.2586	0.3099	0.3431	0.060 (7)*
C12B	−0.1873 (14)	0.0448 (13)	0.3804 (4)	0.050 (3)
H12C	−0.2103	−0.0915	0.3759	0.060 (7)*
H12D	−0.0438	0.0617	0.3778	0.060 (7)*
N13B	−0.2789 (10)	0.0866 (10)	0.4336 (3)	0.055 (2)
H13D	−0.2606	0.2121	0.4376	0.077 (7)*
H13E	−0.2222	0.0094	0.4586	0.077 (7)*
H13F	−0.4095	0.0636	0.4370	0.077 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl2A	0.056 (2)	0.0603 (17)	0.0518 (19)	−0.0029 (14)	−0.0106 (15)	−0.0043 (12)
Cl1A	0.157 (3)	0.121 (3)	0.065 (2)	0.007 (2)	0.048 (2)	−0.0162 (17)
C2A	0.078 (9)	0.051 (6)	0.070 (9)	−0.005 (5)	0.010 (7)	0.006 (5)
C3A	0.122 (10)	0.077 (8)	0.042 (6)	0.009 (7)	−0.010 (6)	−0.016 (5)
C4A	0.056 (6)	0.091 (8)	0.055 (6)	0.004 (5)	−0.011 (5)	−0.020 (5)
C5A	0.055 (7)	0.040 (5)	0.045 (7)	−0.013 (5)	0.001 (5)	−0.001 (4)
C6A	0.071 (8)	0.065 (6)	0.042 (6)	0.006 (5)	−0.005 (5)	0.003 (4)
C7A	0.065 (7)	0.064 (7)	0.080 (8)	0.001 (5)	−0.002 (6)	−0.002 (6)
C8A	0.070 (7)	0.034 (5)	0.052 (7)	−0.018 (5)	−0.007 (5)	0.003 (4)
O9A	0.066 (5)	0.074 (4)	0.090 (5)	−0.031 (4)	0.017 (4)	−0.027 (3)
N10A	0.054 (6)	0.062 (6)	0.044 (6)	−0.020 (5)	0.007 (5)	−0.004 (5)
C11A	0.047 (7)	0.048 (6)	0.048 (7)	−0.001 (5)	−0.009 (6)	0.002 (5)
C12A	0.059 (8)	0.055 (7)	0.046 (7)	0.004 (6)	−0.005 (6)	−0.004 (5)
N13A	0.066 (7)	0.066 (6)	0.046 (6)	−0.005 (5)	−0.015 (5)	0.001 (4)
Cl2B	0.056 (2)	0.0595 (17)	0.057 (2)	−0.0036 (14)	−0.0103 (15)	−0.0015 (13)
Cl1B	0.220 (5)	0.146 (3)	0.071 (2)	0.021 (3)	0.046 (3)	−0.012 (2)
C2B	0.128 (13)	0.064 (8)	0.053 (8)	0.028 (8)	0.013 (9)	−0.018 (6)
C3B	0.152 (14)	0.067 (8)	0.060 (8)	0.002 (8)	−0.029 (9)	0.002 (6)
C4B	0.098 (8)	0.064 (7)	0.061 (7)	−0.017 (6)	−0.016 (6)	0.002 (5)
C5B	0.079 (10)	0.054 (6)	0.041 (6)	−0.002 (6)	−0.009 (6)	−0.013 (5)
C6B	0.062 (7)	0.045 (5)	0.066 (7)	0.001 (5)	0.007 (5)	−0.010 (4)
C7B	0.075 (7)	0.068 (7)	0.073 (8)	0.002 (6)	0.015 (6)	−0.006 (6)
C8B	0.062 (7)	0.061 (7)	0.037 (6)	−0.008 (5)	0.000 (5)	0.004 (5)
O9B	0.084 (6)	0.093 (6)	0.103 (6)	−0.052 (5)	0.019 (4)	−0.029 (4)
N10B	0.060 (6)	0.045 (5)	0.042 (6)	−0.009 (5)	−0.003 (5)	−0.009 (4)
C11B	0.062 (8)	0.058 (7)	0.029 (6)	0.005 (5)	0.002 (6)	−0.010 (5)
C12B	0.057 (8)	0.059 (7)	0.035 (6)	0.009 (6)	−0.013 (6)	−0.006 (5)
N13B	0.058 (6)	0.066 (6)	0.038 (6)	−0.011 (5)	−0.004 (5)	0.000 (4)

Geometric parameters (Å, º) top

Cl1A—C2A	1.708 (12)	Cl1B—C2B	1.753 (12)
C2A—C7A	1.358 (13)	C2B—C3B	1.342 (16)
C2A—C3A	1.377 (14)	C2B—C7B	1.363 (15)
C3A—C4A	1.385 (12)	C3B—C4B	1.373 (15)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.375 (12)	C4B—C5B	1.393 (12)
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—C6A	1.354 (11)	C5B—C6B	1.392 (13)
C5A—C8A	1.484 (13)	C5B—C8B	1.467 (13)
C6A—C7A	1.398 (13)	C6B—C7B	1.404 (12)
C6A—H6A	0.9300	C6B—H6B	0.9300
C7A—H7A	0.9300	C7B—H7B	0.9300
C8A—O9A	1.254 (11)	C8B—O9B	1.224 (11)
C8A—N10A	1.342 (11)	C8B—N10B	1.322 (11)
N10A—C11A	1.438 (10)	N10B—C11B	1.450 (10)
N10A—H10A	0.8600	N10B—H10B	0.8600
C11A—C12A	1.500 (10)	C11B—C12B	1.477 (10)
C11A—H11A	0.9700	C11B—H11C	0.9700
C11A—H11B	0.9700	C11B—H11D	0.9700
C12A—N13A	1.482 (10)	C12B—N13B	1.464 (9)
C12A—H12A	0.9700	C12B—H12C	0.9700
C12A—H12B	0.9700	C12B—H12D	0.9700
N13A—H13A	0.8900	N13B—H13D	0.8900
N13A—H13B	0.8900	N13B—H13E	0.8900
N13A—H13C	0.8900	N13B—H13F	0.8900

C7A—C2A—C3A	118.8 (11)	C3B—C2B—C7B	124.6 (13)
C7A—C2A—Cl1A	121.5 (10)	C3B—C2B—Cl1B	118.6 (13)
C3A—C2A—Cl1A	119.7 (10)	C7B—C2B—Cl1B	116.8 (13)
C2A—C3A—C4A	120.0 (11)	C2B—C3B—C4B	117.1 (13)
C2A—C3A—H3A	120.0	C2B—C3B—H3B	121.5
C4A—C3A—H3A	120.0	C4B—C3B—H3B	121.5
C5A—C4A—C3A	120.1 (10)	C3B—C4B—C5B	124.4 (12)
C5A—C4A—H4A	120.0	C3B—C4B—H4B	117.8
C3A—C4A—H4A	120.0	C5B—C4B—H4B	117.8
C6A—C5A—C4A	120.8 (11)	C4B—C5B—C6B	114.3 (12)
C6A—C5A—C8A	120.4 (10)	C4B—C5B—C8B	122.4 (12)
C4A—C5A—C8A	118.8 (10)	C6B—C5B—C8B	123.3 (11)
C5A—C6A—C7A	118.4 (10)	C5B—C6B—C7B	123.5 (12)
C5A—C6A—H6A	120.8	C5B—C6B—H6B	118.2
C7A—C6A—H6A	120.8	C7B—C6B—H6B	118.2
C2A—C7A—C6A	121.9 (11)	C2B—C7B—C6B	116.0 (12)
C2A—C7A—H7A	119.0	C2B—C7B—H7B	122.0
C6A—C7A—H7A	119.0	C6B—C7B—H7B	122.0
O9A—C8A—N10A	120.3 (12)	O9B—C8B—N10B	122.9 (12)
O9A—C8A—C5A	122.9 (11)	O9B—C8B—C5B	120.6 (12)
N10A—C8A—C5A	116.8 (11)	N10B—C8B—C5B	116.4 (11)
C8A—N10A—C11A	124.4 (10)	C8B—N10B—C11B	122.6 (10)
C8A—N10A—H10A	117.8	C8B—N10B—H10B	118.7
C11A—N10A—H10A	117.8	C11B—N10B—H10B	118.7
N10A—C11A—C12A	110.1 (8)	N10B—C11B—C12B	111.6 (8)
N10A—C11A—H11A	109.6	N10B—C11B—H11C	109.3
C12A—C11A—H11A	109.6	C12B—C11B—H11C	109.3
N10A—C11A—H11B	109.6	N10B—C11B—H11D	109.3
C12A—C11A—H11B	109.6	C12B—C11B—H11D	109.3
H11A—C11A—H11B	108.2	H11C—C11B—H11D	108.0
N13A—C12A—C11A	112.9 (8)	N13B—C12B—C11B	112.7 (8)
N13A—C12A—H12A	109.0	N13B—C12B—H12C	109.1
C11A—C12A—H12A	109.0	C11B—C12B—H12C	109.1
N13A—C12A—H12B	109.0	N13B—C12B—H12D	109.1
C11A—C12A—H12B	109.0	C11B—C12B—H12D	109.1
H12A—C12A—H12B	107.8	H12C—C12B—H12D	107.8
C12A—N13A—H13A	109.5	C12B—N13B—H13D	109.5
C12A—N13A—H13B	109.5	C12B—N13B—H13E	109.5
H13A—N13A—H13B	109.5	H13D—N13B—H13E	109.5
C12A—N13A—H13C	109.5	C12B—N13B—H13F	109.5
H13A—N13A—H13C	109.5	H13D—N13B—H13F	109.5
H13B—N13A—H13C	109.5	H13E—N13B—H13F	109.5

C6A—C5A—C8A—N10A	42.3 (12)	C6B—C5B—C8B—N10B	31.1 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N10A—H10A···O9Bⁱ	0.86	1.95	2.762 (11)	157
N10B—H10B···O9A	0.86	2.02	2.826 (10)	155
N13A—H13A···Cl2A	0.89	2.31	3.198 (7)	174
N13A—H13B···Cl2Bⁱⁱ	0.89	2.52	3.231 (8)	137
N13A—H13C···Cl2B	0.89	2.26	3.143 (8)	172
N13B—H13D···Cl2B	0.89	2.30	3.187 (7)	173
N13B—H13E···Cl2Aⁱⁱ	0.89	2.49	3.206 (7)	138
N13B—H13F···Cl2Aⁱⁱⁱ	0.89	2.27	3.157 (7)	172
C12A—H12B···Cl2B^iv	0.97	2.80	3.569 (10)	137
C12B—H12D···Cl2A^v	0.97	2.70	3.501 (9)	140

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

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A monoamine oxidase B inhibitor: N-(2-amino­eth­yl)-p-chloro­benzamide (Ro16-6491) hydro­chloride

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Subscribe to Acta Crystallographica Section E: Crystallographic Communications

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A monoamine oxidase B inhibitor: N-(2-aminoethyl)-p-chlorobenzamide (Ro16-6491) hydrochloride