Crystallographic characterization of three cathinone hydro­chlorides new on the NPS market: 1-(4-methyl­phen­yl)-2-(pyrrolidin-1-yl)hexan-1-one (4-MPHP), 4-methyl-1-phenyl-2-(pyrrolidin-1-yl)pentan-1-one (α-PiHP) and 2-(methyl­amino)-1-(4-methyl­phen­yl)pentan-1-one (4-MPD)

Cathinones belong to a group of com­pounds of great inter­est in the new psycho­active substances (NPS) market. Constant changes to the chemical struc­ture made by the producers of these com­pounds require a quick reaction from analytical laboratories in ascertaining their characteristics. In this article, three cathinone derivatives were characterized by X-ray crystallography. The investigated com­pounds were confirmed as: 1-[1-(4-methyl­phen­yl)-1-oxo­hexan-2-yl]pyrrolidin-1-ium chloride (1, C₁₇H₂₆NO⁺·Cl⁻, the hydro­chloride of 4-MPHP), 1-(4-methyl-1-oxo-1-phenyl­pentan-2-yl)pyrrolidin-1-ium chloride (2; C₁₆H₂₄NO⁺·Cl⁻, the hydro­chloride of α-PiHP) and meth­yl[1-(4-methyl­phen­yl)-1-oxo­pentan-2-yl]aza­nium chloride (3; C₁₃H₂₀NO⁺·Cl⁻, the hydro­chloride of 4-MPD). All the salts crystallize in a monoclinic space group: 1 and 2 in P2₁/c, and 3 in P2₁/n. To the best of our knowledge, this study provides the first detailed and com­prehensive crystallographic data on salts 1–3.

Computing details

For all structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015).

1-[1-(4-Methylphenyl)-1-oxohexan-2-yl]pyrrolidin-1-ium chloride (ch20_pk1269)

Crystal data

C17H26NO^+·Cl^−	F(000) = 640
Mr = 295.84	Dx = 1.151 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 17.0494 (9) Å	Cell parameters from 2886 reflections
b = 6.9334 (3) Å	θ = 5.4–73.6°
c = 15.241 (1) Å	µ = 1.94 mm^−1
β = 108.635 (7)°	T = 294 K
V = 1707.19 (17) Å^3	Polyhedron, colorless
Z = 4	0.08 × 0.08 × 0.04 mm

Data collection

Agilent SuperNova diffractometer with an Atlas detector	3400 independent reflections
Radiation source: micro-focus sealed X-ray tube	2207 reflections with I > 2σ(I)
Detector resolution: 10.4498 pixels mm^-1	Rint = 0.047
ω scans	θmax = 74.3°, θmin = 5.5°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −21→16
Tmin = 0.480, Tmax = 1.000	k = −8→8
11711 measured reflections	l = −18→18

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.050	w = 1/[σ^2(Fo^2) + (0.0618P)^2 + 0.260P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.143	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.20 e Å^−3
3400 reflections	Δρmin = −0.16 e Å^−3
184 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0019 (3)

Special details

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

Refinement. The single-crystal X-ray experiments were performed at room temperature. The data were collected using a SuperNova kappa diffractometer with Atlas CCD detector (Agilent Technologies, Santa Clara, CA, USA). For the integration of the collected data, the CrysAlis PRO software (version 1.171.38.41q, 2015; Rigaku Oxford Diffraction, Rigaku, Tokyo, Japan) was used. The structures were solved using direct methods with the SHELXS2013 software and the solutions were refined using SHELXL2018/3 program (Sheldrick, 2015).

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

	x	y	z	Uiso*/Ueq
Cl1	0.61628 (4)	0.21454 (8)	0.18970 (5)	0.0621 (2)
O1	0.78864 (13)	0.5776 (3)	0.21150 (16)	0.0775 (6)
C1	0.85218 (15)	0.8538 (4)	0.29481 (19)	0.0528 (6)
C2	0.84184 (17)	1.0456 (4)	0.3143 (2)	0.0702 (8)
H2	0.788906	1.096729	0.301281	0.084*
C3	0.91037 (18)	1.1609 (5)	0.3530 (3)	0.0789 (9)
H3	0.902740	1.289614	0.365389	0.095*
C4	0.98949 (17)	1.0901 (5)	0.3736 (2)	0.0696 (8)
C5	0.99912 (18)	0.9007 (5)	0.3519 (2)	0.0785 (9)
H5	1.052157	0.850882	0.363885	0.094*
C6	0.93187 (16)	0.7839 (4)	0.3128 (2)	0.0686 (8)
H6	0.939955	0.656695	0.298373	0.082*
C7	0.78160 (15)	0.7207 (4)	0.25425 (19)	0.0536 (6)
C8	0.70078 (14)	0.7615 (3)	0.27361 (18)	0.0484 (6)
H8	0.688691	0.899563	0.264428	0.058*
N1	0.63213 (11)	0.6520 (3)	0.20618 (14)	0.0464 (5)
H1	0.646988	0.514934	0.212087	0.056*
C9	0.61602 (19)	0.7095 (4)	0.10622 (19)	0.0698 (8)
H9A	0.629238	0.604290	0.071400	0.084*
H9B	0.649002	0.820988	0.102048	0.084*
C10	0.5243 (2)	0.7569 (5)	0.0696 (2)	0.0929 (12)
H10A	0.515502	0.894662	0.072396	0.111*
H10B	0.500605	0.714370	0.005961	0.111*
C11	0.48658 (18)	0.6512 (5)	0.1310 (2)	0.0776 (9)
H11A	0.477739	0.516410	0.113569	0.093*
H11B	0.434327	0.708661	0.129621	0.093*
C12	0.55060 (15)	0.6738 (4)	0.2243 (2)	0.0596 (7)
H12A	0.544286	0.575216	0.266684	0.072*
H12B	0.546496	0.799652	0.250288	0.072*
C13	0.71033 (15)	0.7113 (4)	0.37435 (17)	0.0523 (6)
H13A	0.750494	0.798606	0.414410	0.063*
H13B	0.657781	0.733874	0.384584	0.063*
C14	0.73739 (17)	0.5056 (4)	0.40294 (18)	0.0589 (7)
H14A	0.702604	0.418251	0.357157	0.071*
H14B	0.793801	0.489106	0.402652	0.071*
C15	0.7334 (2)	0.4492 (5)	0.4974 (2)	0.0711 (8)
H15A	0.768370	0.535813	0.543392	0.085*
H15B	0.677029	0.465355	0.497886	0.085*
C16	0.7600 (3)	0.2468 (6)	0.5238 (3)	0.1066 (13)
H16A	0.725128	0.159849	0.479130	0.160*
H16B	0.755754	0.219516	0.583829	0.160*
H16C	0.816398	0.230562	0.525367	0.160*
C17	1.0640 (2)	1.2168 (6)	0.4200 (3)	0.0996 (12)
H17A	1.078255	1.205163	0.485982	0.149*
H17B	1.050735	1.348696	0.402216	0.149*
H17C	1.109971	1.176513	0.400987	0.149*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0698 (4)	0.0326 (3)	0.0768 (5)	0.0022 (3)	0.0135 (3)	−0.0021 (3)
O1	0.0762 (13)	0.0633 (12)	0.1053 (17)	−0.0081 (10)	0.0463 (12)	−0.0286 (12)
C1	0.0487 (13)	0.0505 (13)	0.0602 (15)	−0.0016 (11)	0.0188 (11)	0.0001 (12)
C2	0.0499 (14)	0.0529 (16)	0.108 (3)	−0.0041 (12)	0.0251 (15)	−0.0080 (16)
C3	0.0607 (17)	0.0615 (18)	0.114 (3)	−0.0131 (13)	0.0276 (17)	−0.0149 (18)
C4	0.0553 (16)	0.086 (2)	0.0664 (18)	−0.0167 (14)	0.0179 (14)	−0.0018 (16)
C5	0.0469 (15)	0.095 (3)	0.088 (2)	0.0052 (15)	0.0144 (15)	0.0022 (19)
C6	0.0554 (15)	0.0667 (17)	0.084 (2)	0.0064 (13)	0.0224 (14)	−0.0010 (16)
C7	0.0599 (14)	0.0435 (13)	0.0606 (15)	0.0006 (11)	0.0238 (12)	−0.0003 (12)
C8	0.0472 (12)	0.0342 (11)	0.0621 (15)	−0.0016 (9)	0.0151 (11)	−0.0043 (10)
N1	0.0505 (11)	0.0318 (9)	0.0539 (12)	0.0006 (7)	0.0127 (9)	0.0018 (8)
C9	0.091 (2)	0.0595 (16)	0.0535 (16)	−0.0123 (15)	0.0160 (15)	0.0080 (13)
C10	0.108 (3)	0.066 (2)	0.072 (2)	0.0056 (18)	−0.0191 (19)	0.0051 (16)
C11	0.0610 (17)	0.0709 (19)	0.086 (2)	0.0076 (14)	0.0019 (16)	−0.0114 (17)
C12	0.0455 (13)	0.0559 (16)	0.0729 (18)	0.0052 (11)	0.0125 (12)	−0.0050 (13)
C13	0.0516 (13)	0.0485 (13)	0.0562 (15)	−0.0006 (11)	0.0164 (11)	−0.0128 (12)
C14	0.0636 (15)	0.0561 (15)	0.0559 (15)	0.0095 (12)	0.0176 (13)	0.0012 (12)
C15	0.0793 (19)	0.079 (2)	0.0570 (17)	−0.0020 (15)	0.0239 (15)	0.0016 (15)
C16	0.119 (3)	0.111 (3)	0.096 (3)	0.035 (2)	0.043 (2)	0.047 (2)
C17	0.0670 (19)	0.130 (3)	0.095 (3)	−0.035 (2)	0.0172 (18)	−0.017 (2)

Geometric parameters (Å, º)

O1—C7	1.214 (3)	C10—C11	1.487 (5)
C1—C6	1.385 (4)	C10—H10A	0.9700
C1—C2	1.386 (4)	C10—H10B	0.9700
C1—C7	1.485 (3)	C11—C12	1.499 (4)
C2—C3	1.383 (4)	C11—H11A	0.9700
C2—H2	0.9300	C11—H11B	0.9700
C3—C4	1.374 (4)	C12—H12A	0.9700
C3—H3	0.9300	C12—H12B	0.9700
C4—C5	1.376 (4)	C13—C14	1.519 (4)
C4—C17	1.520 (4)	C13—H13A	0.9700
C5—C6	1.374 (4)	C13—H13B	0.9700
C5—H5	0.9300	C14—C15	1.514 (4)
C6—H6	0.9300	C14—H14A	0.9700
C7—C8	1.525 (3)	C14—H14B	0.9700
C8—N1	1.495 (3)	C15—C16	1.491 (5)
C8—C13	1.531 (4)	C15—H15A	0.9700
C8—H8	0.9800	C15—H15B	0.9700
N1—C12	1.509 (3)	C16—H16A	0.9600
N1—C9	1.513 (3)	C16—H16B	0.9600
N1—H1	0.9800	C16—H16C	0.9600
C9—C10	1.518 (5)	C17—H17A	0.9600
C9—H9A	0.9700	C17—H17B	0.9600
C9—H9B	0.9700	C17—H17C	0.9600
C6—C1—C2	118.5 (2)	H10A—C10—H10B	108.8
C6—C1—C7	118.6 (2)	C10—C11—C12	102.4 (2)
C2—C1—C7	122.9 (2)	C10—C11—H11A	111.3
C3—C2—C1	119.9 (3)	C12—C11—H11A	111.3
C3—C2—H2	120.1	C10—C11—H11B	111.3
C1—C2—H2	120.1	C12—C11—H11B	111.3
C4—C3—C2	121.7 (3)	H11A—C11—H11B	109.2
C4—C3—H3	119.2	C11—C12—N1	104.5 (2)
C2—C3—H3	119.2	C11—C12—H12A	110.9
C3—C4—C5	118.0 (3)	N1—C12—H12A	110.9
C3—C4—C17	120.9 (3)	C11—C12—H12B	110.9
C5—C4—C17	121.1 (3)	N1—C12—H12B	110.9
C6—C5—C4	121.3 (3)	H12A—C12—H12B	108.9
C6—C5—H5	119.4	C14—C13—C8	115.2 (2)
C4—C5—H5	119.4	C14—C13—H13A	108.5
C5—C6—C1	120.6 (3)	C8—C13—H13A	108.5
C5—C6—H6	119.7	C14—C13—H13B	108.5
C1—C6—H6	119.7	C8—C13—H13B	108.5
O1—C7—C1	121.7 (2)	H13A—C13—H13B	107.5
O1—C7—C8	120.4 (2)	C15—C14—C13	114.4 (2)
C1—C7—C8	117.8 (2)	C15—C14—H14A	108.7
N1—C8—C7	109.29 (19)	C13—C14—H14A	108.7
N1—C8—C13	112.52 (19)	C15—C14—H14B	108.7
C7—C8—C13	109.8 (2)	C13—C14—H14B	108.7
N1—C8—H8	108.4	H14A—C14—H14B	107.6
C7—C8—H8	108.4	C16—C15—C14	113.4 (3)
C13—C8—H8	108.4	C16—C15—H15A	108.9
C8—N1—C12	112.83 (19)	C14—C15—H15A	108.9
C8—N1—C9	114.14 (19)	C16—C15—H15B	108.9
C12—N1—C9	106.0 (2)	C14—C15—H15B	108.9
C8—N1—H1	107.9	H15A—C15—H15B	107.7
C12—N1—H1	107.9	C15—C16—H16A	109.5
C9—N1—H1	107.9	C15—C16—H16B	109.5
N1—C9—C10	105.2 (3)	H16A—C16—H16B	109.5
N1—C9—H9A	110.7	C15—C16—H16C	109.5
C10—C9—H9A	110.7	H16A—C16—H16C	109.5
N1—C9—H9B	110.7	H16B—C16—H16C	109.5
C10—C9—H9B	110.7	C4—C17—H17A	109.5
H9A—C9—H9B	108.8	C4—C17—H17B	109.5
C11—C10—C9	105.3 (2)	H17A—C17—H17B	109.5
C11—C10—H10A	110.7	C4—C17—H17C	109.5
C9—C10—H10A	110.7	H17A—C17—H17C	109.5
C11—C10—H10B	110.7	H17B—C17—H17C	109.5
C9—C10—H10B	110.7

1-(4-Methyl-1-oxo-1-phenylpentan-2-yl)pyrrolidin-1-ium chloride (ch20_pk1270)

Crystal data

C16H24NO^+·Cl^−	F(000) = 608
Mr = 281.81	Dx = 1.139 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 14.0379 (13) Å	Cell parameters from 1846 reflections
b = 10.3133 (5) Å	θ = 5.3–69.3°
c = 11.4344 (7) Å	µ = 1.99 mm^−1
β = 96.829 (7)°	T = 294 K
V = 1643.7 (2) Å^3	Parallelepiped, colorless
Z = 4	0.17 × 0.08 × 0.04 mm

Data collection

Agilent SuperNova diffractometer with an Atlas detector	2938 independent reflections
Radiation source: micro-focus sealed X-ray tube	1541 reflections with I > 2σ(I)
Detector resolution: 10.4498 pixels mm^-1	Rint = 0.047
ω scans	θmax = 73.5°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −17→16
Tmin = 0.633, Tmax = 1.000	k = −12→12
7563 measured reflections	l = −9→14

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.064	w = 1/[σ^2(Fo^2) + (0.0959P)^2 + 1.2724P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.245	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.30 e Å^−3
2938 reflections	Δρmin = −0.42 e Å^−3
175 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0033 (7)

Special details

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

Refinement. The single-crystal X-ray experiments were performed at room temperature. The data were collected using a SuperNova kappa diffractometer with Atlas CCD detector (Agilent Technologies, Santa Clara, CA, USA). For the integration of the collected data, the CrysAlis PRO software (version 1.171.38.41q, 2015; Rigaku Oxford Diffraction, Rigaku, Tokyo, Japan) was used. The structures were solved using direct methods with the SHELXS2013 software and the solutions were refined using SHELXL2018/3 program (Sheldrick, 2015).

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

	x	y	z	Uiso*/Ueq
Cl1	0.63520 (11)	0.06947 (12)	0.15315 (10)	0.0782 (5)
O1	0.2540 (3)	0.8958 (4)	0.3051 (3)	0.0909 (13)
N1	0.3639 (3)	0.7638 (3)	0.1508 (3)	0.0537 (9)
H1	0.351636	0.714736	0.220908	0.064*
C1	0.2412 (3)	1.0750 (5)	0.1768 (4)	0.0602 (12)
C2	0.2739 (4)	1.1340 (4)	0.0811 (4)	0.0658 (13)
H2	0.302599	1.084303	0.027163	0.079*
C3	0.2646 (4)	1.2648 (5)	0.0648 (5)	0.0775 (15)
H3	0.288000	1.304273	0.000818	0.093*
C4	0.2206 (4)	1.3378 (5)	0.1434 (6)	0.0854 (17)
H4	0.214854	1.427015	0.132957	0.103*
C5	0.1851 (5)	1.2801 (6)	0.2366 (5)	0.0870 (17)
H5	0.153511	1.329683	0.287970	0.104*
C6	0.1961 (4)	1.1491 (5)	0.2548 (5)	0.0741 (14)
H6	0.173231	1.110280	0.319351	0.089*
C7	0.2566 (3)	0.9351 (4)	0.2058 (4)	0.0589 (12)
C8	0.2746 (3)	0.8385 (4)	0.1095 (4)	0.0580 (11)
H8	0.282879	0.884964	0.036598	0.070*
C9	0.4504 (3)	0.8451 (5)	0.1838 (5)	0.0719 (14)
H9A	0.452305	0.917364	0.129811	0.086*
H9B	0.451146	0.878614	0.263154	0.086*
C10	0.5327 (4)	0.7561 (6)	0.1758 (6)	0.0900 (17)
H10A	0.544935	0.703117	0.246123	0.108*
H10B	0.590375	0.804048	0.164814	0.108*
C11	0.5005 (5)	0.6751 (7)	0.0708 (6)	0.099 (2)
H11A	0.528009	0.588945	0.080002	0.119*
H11B	0.520335	0.714062	0.000404	0.119*
C12	0.3927 (4)	0.6682 (5)	0.0617 (4)	0.0666 (13)
H12A	0.372036	0.581353	0.079500	0.080*
H12B	0.364199	0.691348	−0.016952	0.080*
C13	0.1898 (4)	0.7458 (5)	0.0881 (4)	0.0678 (13)
H13A	0.203710	0.682122	0.030049	0.081*
H13B	0.183685	0.699713	0.160821	0.081*
C14	0.0949 (4)	0.8087 (7)	0.0464 (5)	0.0909 (18)
H14	0.083972	0.877490	0.102432	0.109*
C15	0.0937 (5)	0.8701 (8)	−0.0740 (6)	0.120 (3)
H15A	0.135085	0.944462	−0.068498	0.180*
H15B	0.029448	0.896410	−0.102272	0.180*
H15C	0.115686	0.808340	−0.127577	0.180*
C16	0.0147 (5)	0.7099 (10)	0.0476 (7)	0.144 (3)
H16A	0.028265	0.635831	0.001474	0.215*
H16B	−0.044905	0.748144	0.014863	0.215*
H16C	0.010124	0.683291	0.127182	0.215*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1122 (12)	0.0652 (7)	0.0596 (7)	−0.0108 (7)	0.0204 (7)	−0.0078 (5)
O1	0.137 (4)	0.085 (2)	0.053 (2)	0.022 (2)	0.022 (2)	0.0133 (18)
N1	0.057 (2)	0.058 (2)	0.0457 (18)	−0.0032 (17)	0.0056 (16)	−0.0022 (15)
C1	0.060 (3)	0.069 (3)	0.049 (2)	0.001 (2)	−0.002 (2)	−0.005 (2)
C2	0.082 (4)	0.055 (3)	0.060 (3)	0.005 (2)	0.006 (2)	−0.002 (2)
C3	0.081 (4)	0.070 (3)	0.079 (3)	−0.006 (3)	−0.001 (3)	0.001 (3)
C4	0.093 (4)	0.057 (3)	0.102 (4)	−0.004 (3)	−0.009 (3)	−0.009 (3)
C5	0.100 (5)	0.074 (4)	0.087 (4)	0.004 (3)	0.013 (3)	−0.020 (3)
C6	0.091 (4)	0.066 (3)	0.066 (3)	−0.002 (3)	0.011 (3)	−0.012 (2)
C7	0.072 (3)	0.054 (2)	0.051 (2)	0.005 (2)	0.007 (2)	0.003 (2)
C8	0.057 (3)	0.061 (2)	0.055 (2)	0.004 (2)	0.000 (2)	0.006 (2)
C9	0.057 (3)	0.068 (3)	0.088 (4)	−0.002 (2)	−0.003 (3)	−0.008 (3)
C10	0.059 (4)	0.090 (4)	0.118 (5)	0.004 (3)	−0.002 (3)	0.000 (4)
C11	0.079 (4)	0.119 (5)	0.100 (4)	0.007 (4)	0.016 (3)	−0.021 (4)
C12	0.078 (4)	0.067 (3)	0.055 (3)	0.001 (3)	0.008 (2)	−0.009 (2)
C13	0.061 (3)	0.078 (3)	0.063 (3)	−0.001 (3)	0.005 (2)	−0.005 (2)
C14	0.062 (4)	0.121 (5)	0.088 (4)	0.007 (4)	0.000 (3)	−0.015 (4)
C15	0.091 (5)	0.152 (7)	0.109 (5)	0.020 (5)	−0.022 (4)	0.014 (5)
C16	0.073 (5)	0.219 (10)	0.138 (7)	−0.034 (6)	0.008 (4)	0.001 (6)

Geometric parameters (Å, º)

O1—C7	1.210 (5)	C9—H9B	0.9700
N1—C9	1.487 (6)	C10—C11	1.488 (8)
N1—C8	1.499 (5)	C10—H10A	0.9700
N1—C12	1.507 (5)	C10—H10B	0.9700
N1—H1	0.9800	C11—C12	1.506 (8)
C1—C2	1.378 (6)	C11—H11A	0.9700
C1—C6	1.383 (7)	C11—H11B	0.9700
C1—C7	1.491 (6)	C12—H12A	0.9700
C2—C3	1.366 (7)	C12—H12B	0.9700
C2—H2	0.9300	C13—C14	1.507 (7)
C3—C4	1.374 (8)	C13—H13A	0.9700
C3—H3	0.9300	C13—H13B	0.9700
C4—C5	1.366 (8)	C14—C15	1.514 (8)
C4—H4	0.9300	C14—C16	1.520 (10)
C5—C6	1.373 (7)	C14—H14	0.9800
C5—H5	0.9300	C15—H15A	0.9600
C6—H6	0.9300	C15—H15B	0.9600
C7—C8	1.528 (6)	C15—H15C	0.9600
C8—C13	1.524 (7)	C16—H16A	0.9600
C8—H8	0.9800	C16—H16B	0.9600
C9—C10	1.487 (7)	C16—H16C	0.9600
C9—H9A	0.9700
C9—N1—C8	114.7 (4)	C11—C10—H10A	111.1
C9—N1—C12	105.3 (4)	C9—C10—H10B	111.1
C8—N1—C12	113.8 (3)	C11—C10—H10B	111.1
C9—N1—H1	107.6	H10A—C10—H10B	109.0
C8—N1—H1	107.6	C10—C11—C12	106.8 (5)
C12—N1—H1	107.6	C10—C11—H11A	110.4
C2—C1—C6	119.3 (5)	C12—C11—H11A	110.4
C2—C1—C7	123.4 (4)	C10—C11—H11B	110.4
C6—C1—C7	117.2 (4)	C12—C11—H11B	110.4
C3—C2—C1	120.6 (5)	H11A—C11—H11B	108.6
C3—C2—H2	119.7	C11—C12—N1	105.7 (4)
C1—C2—H2	119.7	C11—C12—H12A	110.6
C2—C3—C4	119.6 (6)	N1—C12—H12A	110.6
C2—C3—H3	120.2	C11—C12—H12B	110.6
C4—C3—H3	120.2	N1—C12—H12B	110.6
C5—C4—C3	120.4 (5)	H12A—C12—H12B	108.7
C5—C4—H4	119.8	C14—C13—C8	115.1 (5)
C3—C4—H4	119.8	C14—C13—H13A	108.5
C4—C5—C6	120.1 (6)	C8—C13—H13A	108.5
C4—C5—H5	119.9	C14—C13—H13B	108.5
C6—C5—H5	119.9	C8—C13—H13B	108.5
C5—C6—C1	119.9 (5)	H13A—C13—H13B	107.5
C5—C6—H6	120.1	C13—C14—C15	112.5 (5)
C1—C6—H6	120.1	C13—C14—C16	109.6 (6)
O1—C7—C1	120.8 (4)	C15—C14—C16	111.1 (6)
O1—C7—C8	118.9 (4)	C13—C14—H14	107.8
C1—C7—C8	120.2 (4)	C15—C14—H14	107.8
N1—C8—C13	109.7 (4)	C16—C14—H14	107.8
N1—C8—C7	108.1 (3)	C14—C15—H15A	109.5
C13—C8—C7	109.3 (4)	C14—C15—H15B	109.5
N1—C8—H8	109.9	H15A—C15—H15B	109.5
C13—C8—H8	109.9	C14—C15—H15C	109.5
C7—C8—H8	109.9	H15A—C15—H15C	109.5
C10—C9—N1	104.7 (4)	H15B—C15—H15C	109.5
C10—C9—H9A	110.8	C14—C16—H16A	109.5
N1—C9—H9A	110.8	C14—C16—H16B	109.5
C10—C9—H9B	110.8	H16A—C16—H16B	109.5
N1—C9—H9B	110.8	C14—C16—H16C	109.5
H9A—C9—H9B	108.9	H16A—C16—H16C	109.5
C9—C10—C11	103.4 (5)	H16B—C16—H16C	109.5
C9—C10—H10A	111.1
C6—C1—C2—C3	1.9 (7)	O1—C7—C8—N1	−52.9 (6)
C7—C1—C2—C3	−174.5 (5)	C1—C7—C8—N1	127.9 (4)
C1—C2—C3—C4	−1.3 (8)	O1—C7—C8—C13	66.5 (6)
C2—C3—C4—C5	−0.8 (8)	C1—C7—C8—C13	−112.8 (5)
C3—C4—C5—C6	2.1 (9)	C8—N1—C9—C10	−158.7 (4)
C4—C5—C6—C1	−1.5 (9)	C12—N1—C9—C10	−32.7 (5)
C2—C1—C6—C5	−0.5 (8)	N1—C9—C10—C11	38.1 (6)
C7—C1—C6—C5	176.1 (5)	C9—C10—C11—C12	−28.9 (7)
C2—C1—C7—O1	157.2 (5)	C10—C11—C12—N1	9.0 (6)
C6—C1—C7—O1	−19.3 (7)	C9—N1—C12—C11	14.5 (5)
C2—C1—C7—C8	−23.6 (7)	C8—N1—C12—C11	140.9 (5)
C6—C1—C7—C8	160.0 (4)	N1—C8—C13—C14	179.8 (4)
C9—N1—C8—C13	−175.4 (4)	C7—C8—C13—C14	61.4 (5)
C12—N1—C8—C13	63.3 (5)	C8—C13—C14—C15	64.9 (7)
C9—N1—C8—C7	−56.3 (5)	C8—C13—C14—C16	−170.9 (5)
C12—N1—C8—C7	−177.6 (4)

Methyl[1-(4-methylphenyl)-1-oxopentan-2-yl]azanium chloride (ch20_pk1271)

Crystal data

C13H20NO^+·Cl^−	F(000) = 520
Mr = 241.75	Dx = 1.140 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 7.1747 (2) Å	Cell parameters from 6458 reflections
b = 7.8832 (2) Å	θ = 5.8–73.6°
c = 24.9469 (6) Å	µ = 2.24 mm^−1
β = 93.765 (2)°	T = 294 K
V = 1407.94 (6) Å^3	Polyhedron, colorless
Z = 4	0.38 × 0.33 × 0.08 mm

Data collection

Agilent SuperNova diffractometer with an Atlas detector	2799 independent reflections
Radiation source: micro-focus sealed X-ray tube	2694 reflections with I > 2σ(I)
Detector resolution: 10.4498 pixels mm^-1	Rint = 0.016
ω scans	θmax = 73.5°, θmin = 3.6°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −8→6
Tmin = 0.600, Tmax = 1.000	k = −8→9
9319 measured reflections	l = −29→30

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.128	w = 1/[σ^2(Fo^2) + (0.0731P)^2 + 0.3144P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
2799 reflections	Δρmax = 0.41 e Å^−3
148 parameters	Δρmin = −0.26 e Å^−3

Special details

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

Refinement. The single-crystal X-ray experiments were performed at room temperature. The data were collected using a SuperNova kappa diffractometer with Atlas CCD detector (Agilent Technologies, Santa Clara, CA, USA). For the integration of the collected data, the CrysAlis PRO software (version 1.171.38.41q, 2015; Rigaku Oxford Diffraction, Rigaku, Tokyo, Japan) was used. The structures were solved using direct methods with the SHELXS2013 software and the solutions were refined using SHELXL2018/3 program (Sheldrick, 2015).

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

	x	y	z	Uiso*/Ueq
Cl1	0.98520 (5)	0.13609 (5)	0.23702 (2)	0.05579 (17)
O1	0.63367 (17)	−0.12727 (16)	0.14209 (5)	0.0611 (3)
N1	0.56633 (17)	0.01840 (16)	0.23441 (5)	0.0485 (3)
H14A	0.576783	−0.091220	0.242590	0.058*
H14B	0.675937	0.052917	0.223654	0.058*
C1	0.3264 (2)	−0.12105 (19)	0.10155 (6)	0.0495 (4)
C2	0.1371 (3)	−0.1186 (2)	0.11019 (7)	0.0587 (4)
H2	0.097612	−0.082260	0.143057	0.070*
C3	0.0070 (3)	−0.1699 (3)	0.07003 (8)	0.0685 (5)
H3	−0.119017	−0.170254	0.076715	0.082*
C4	0.0597 (3)	−0.2205 (2)	0.02051 (8)	0.0670 (5)
C5	0.2473 (3)	−0.2187 (3)	0.01155 (7)	0.0743 (6)
H5	0.285158	−0.249441	−0.022041	0.089*
C6	0.3809 (3)	−0.1719 (3)	0.05155 (7)	0.0646 (5)
H6	0.506895	−0.174461	0.044910	0.077*
C7	0.4736 (2)	−0.07816 (19)	0.14386 (6)	0.0473 (3)
C8	0.4223 (2)	0.03854 (19)	0.18908 (6)	0.0476 (3)
H8	0.301161	0.003000	0.201248	0.057*
C9	0.5251 (3)	0.1140 (3)	0.28359 (8)	0.0663 (5)
H9A	0.531281	0.233577	0.276579	0.099*
H9B	0.615171	0.084950	0.312274	0.099*
H9C	0.402158	0.085362	0.293691	0.099*
C10	0.4045 (3)	0.2197 (2)	0.16777 (7)	0.0600 (4)
H10A	0.294877	0.226186	0.142936	0.072*
H10B	0.383968	0.294841	0.197619	0.072*
C11	0.5703 (4)	0.2836 (3)	0.13969 (10)	0.0822 (6)
H11A	0.598673	0.204151	0.111682	0.099*
H11B	0.677954	0.289277	0.165253	0.099*
C12	0.5352 (5)	0.4574 (3)	0.11506 (11)	0.0999 (9)
H12A	0.437293	0.449836	0.087018	0.150*
H12B	0.647292	0.497751	0.100354	0.150*
H12C	0.498711	0.534689	0.142209	0.150*
C13	−0.0843 (4)	−0.2748 (3)	−0.02325 (10)	0.0945 (8)
H13A	−0.159547	−0.364419	−0.010068	0.142*
H13B	−0.022123	−0.314483	−0.053783	0.142*
H13C	−0.162519	−0.180013	−0.033631	0.142*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0426 (2)	0.0505 (3)	0.0748 (3)	0.00148 (14)	0.00800 (18)	−0.01062 (16)
O1	0.0526 (7)	0.0611 (7)	0.0700 (7)	0.0078 (5)	0.0063 (6)	−0.0106 (5)
N1	0.0457 (7)	0.0453 (7)	0.0544 (7)	0.0014 (5)	0.0027 (5)	−0.0009 (5)
C1	0.0562 (9)	0.0417 (8)	0.0508 (8)	0.0015 (6)	0.0044 (7)	0.0011 (6)
C2	0.0573 (10)	0.0629 (10)	0.0560 (9)	−0.0028 (7)	0.0050 (7)	−0.0018 (7)
C3	0.0606 (11)	0.0742 (12)	0.0696 (11)	−0.0063 (9)	−0.0039 (8)	−0.0022 (9)
C4	0.0776 (12)	0.0564 (10)	0.0651 (10)	−0.0003 (9)	−0.0114 (9)	0.0000 (8)
C5	0.0920 (15)	0.0789 (13)	0.0515 (9)	0.0068 (11)	0.0012 (9)	−0.0102 (9)
C6	0.0663 (11)	0.0706 (11)	0.0574 (9)	0.0054 (9)	0.0088 (8)	−0.0063 (8)
C7	0.0492 (8)	0.0392 (7)	0.0540 (8)	0.0023 (6)	0.0074 (6)	0.0021 (6)
C8	0.0456 (8)	0.0449 (8)	0.0523 (8)	0.0032 (6)	0.0028 (6)	−0.0017 (6)
C9	0.0643 (11)	0.0773 (13)	0.0569 (10)	0.0032 (9)	0.0009 (8)	−0.0151 (9)
C10	0.0713 (11)	0.0439 (8)	0.0638 (10)	0.0100 (7)	−0.0034 (8)	−0.0024 (7)
C11	0.1015 (17)	0.0564 (11)	0.0892 (14)	−0.0018 (11)	0.0090 (12)	0.0174 (10)
C12	0.161 (3)	0.0510 (11)	0.0849 (15)	−0.0130 (14)	−0.0136 (16)	0.0133 (11)
C13	0.113 (2)	0.0822 (15)	0.0828 (14)	−0.0043 (14)	−0.0348 (14)	−0.0086 (12)

Geometric parameters (Å, º)

O1—C7	1.2158 (19)	C8—C10	1.527 (2)
N1—C9	1.486 (2)	C8—H8	0.9800
N1—C8	1.4894 (19)	C9—H9A	0.9600
N1—H14A	0.8900	C9—H9B	0.9600
N1—H14B	0.8900	C9—H9C	0.9600
C1—C2	1.390 (2)	C10—C11	1.506 (3)
C1—C6	1.390 (2)	C10—H10A	0.9700
C1—C7	1.482 (2)	C10—H10B	0.9700
C2—C3	1.384 (3)	C11—C12	1.516 (3)
C2—H2	0.9300	C11—H11A	0.9700
C3—C4	1.375 (3)	C11—H11B	0.9700
C3—H3	0.9300	C12—H12A	0.9600
C4—C5	1.379 (3)	C12—H12B	0.9600
C4—C13	1.515 (3)	C12—H12C	0.9600
C5—C6	1.387 (3)	C13—H13A	0.9600
C5—H5	0.9300	C13—H13B	0.9600
C6—H6	0.9300	C13—H13C	0.9600
C7—C8	1.520 (2)
C9—N1—C8	114.00 (12)	C10—C8—H8	108.6
C9—N1—H14A	108.8	N1—C9—H9A	109.5
C8—N1—H14A	108.8	N1—C9—H9B	109.5
C9—N1—H14B	108.8	H9A—C9—H9B	109.5
C8—N1—H14B	108.8	N1—C9—H9C	109.5
H14A—N1—H14B	107.6	H9A—C9—H9C	109.5
C2—C1—C6	118.58 (16)	H9B—C9—H9C	109.5
C2—C1—C7	122.97 (15)	C11—C10—C8	115.10 (15)
C6—C1—C7	118.41 (15)	C11—C10—H10A	108.5
C3—C2—C1	120.22 (18)	C8—C10—H10A	108.5
C3—C2—H2	119.9	C11—C10—H10B	108.5
C1—C2—H2	119.9	C8—C10—H10B	108.5
C4—C3—C2	121.55 (19)	H10A—C10—H10B	107.5
C4—C3—H3	119.2	C10—C11—C12	112.1 (2)
C2—C3—H3	119.2	C10—C11—H11A	109.2
C3—C4—C5	118.13 (18)	C12—C11—H11A	109.2
C3—C4—C13	121.0 (2)	C10—C11—H11B	109.2
C5—C4—C13	120.9 (2)	C12—C11—H11B	109.2
C4—C5—C6	121.46 (18)	H11A—C11—H11B	107.9
C4—C5—H5	119.3	C11—C12—H12A	109.5
C6—C5—H5	119.3	C11—C12—H12B	109.5
C5—C6—C1	120.03 (18)	H12A—C12—H12B	109.5
C5—C6—H6	120.0	C11—C12—H12C	109.5
C1—C6—H6	120.0	H12A—C12—H12C	109.5
O1—C7—C1	122.14 (15)	H12B—C12—H12C	109.5
O1—C7—C8	119.68 (14)	C4—C13—H13A	109.5
C1—C7—C8	118.11 (13)	C4—C13—H13B	109.5
N1—C8—C7	108.02 (12)	H13A—C13—H13B	109.5
N1—C8—C10	113.71 (13)	C4—C13—H13C	109.5
C7—C8—C10	109.07 (13)	H13A—C13—H13C	109.5
N1—C8—H8	108.6	H13B—C13—H13C	109.5
C7—C8—H8	108.6
C6—C1—C2—C3	1.6 (3)	C2—C1—C7—C8	−25.7 (2)
C7—C1—C2—C3	−176.03 (16)	C6—C1—C7—C8	156.66 (15)
C1—C2—C3—C4	−1.6 (3)	C9—N1—C8—C7	−174.85 (14)
C2—C3—C4—C5	−0.1 (3)	C9—N1—C8—C10	63.95 (18)
C2—C3—C4—C13	−179.40 (19)	O1—C7—C8—N1	−21.3 (2)
C3—C4—C5—C6	1.8 (3)	C1—C7—C8—N1	161.81 (13)
C13—C4—C5—C6	−178.9 (2)	O1—C7—C8—C10	102.75 (17)
C4—C5—C6—C1	−1.7 (3)	C1—C7—C8—C10	−74.14 (17)
C2—C1—C6—C5	0.0 (3)	N1—C8—C10—C11	67.9 (2)
C7—C1—C6—C5	177.76 (17)	C7—C8—C10—C11	−52.7 (2)
C2—C1—C7—O1	157.51 (16)	C8—C10—C11—C12	174.53 (18)
C6—C1—C7—O1	−20.1 (2)