The ecstasy and the agony; compression studies of 3,4-methylenedioxymethamphetamine (MDMA)

Connor, L.E.; Delori, A.; Hutchison, I.B.; Nic Daeid, N.; Sutcliffe, O.B.; Oswald, I.D.H.

doi:10.1107/S2052520614026389

The ecstasy and the agony; compression studies of 3,4-methylenedioxymethamphetamine (MDMA)

L. E. Connor, A. Delori, I. B. Hutchison, N. Nic Daeid, O. B. Sutcliffe and I. D. H. Oswald

MDMA (3,4-methylenedioxymethamphetamine) is a Class A substance that is usually found in a tableted form. It is only observed in one orthorhombic polymorph under ambient conditions. It shows slight positional disorder around the methlyenedioxy ring which persists during compression up to 6.66 GPa. The crystal quality deteriorates above 6.66 GPa where the hydrostatic limit of the pressure-transmitting medium is exceeded. The structure undergoes anisotropic compression with the a-axis compressing the greatest (12% cf. 4 and 10% for the b- and c-axes, respectively). This is due to the pattern of the hydrogen bonding which acts like a spring and allows the compression along this direction.

Keywords: ecstasy; MDMA; compression; entactogen.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520614026389/ps5039sup1.cif Contains datablocks global1, global2, global3, global4, global5, global6, global7, 1, 2, 3, 4, 5, 6, 7
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520614026389/ps50391sup2.hkl Contains datablock 1
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520614026389/ps50392sup3.hkl Contains datablock 2
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520614026389/ps50393sup4.hkl Contains datablock 3
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520614026389/ps50394sup5.hkl Contains datablock 4
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520614026389/ps50395sup6.hkl Contains datablock 5
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520614026389/ps50396sup7.hkl Contains datablock 6
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520614026389/ps50397sup8.hkl Contains datablock 7

CCDC references: 1036952; 1036953; 1036954; 1036955; 1036956; 1036957; 1036958

Experimental top

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1.

Results and discussion top

Computing details top

For all compounds, data collection: Apex2 (Bruker AXS, 2006); cell refinement: Apex2 (Bruker AXS, 2006); data reduction: Apex2 (Bruker AXS, 2006); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

Figures top

(1) top

Crystal data top

C₁₁H₁₆NO₂·Cl	F(000) = 488
M_r = 229.71	D_x = 1.253 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 9646 reflections
a = 9.4272 (2) Å	θ = 3–27°
b = 7.0774 (2) Å	µ = 0.30 mm⁻¹
c = 18.2519 (4) Å	T = 293 K
V = 1217.77 (3) Å³	Block, colourless
Z = 4	0.35 × 0.22 × 0.10 mm

Data collection top

Bruker Kappa Apex2 diffractometer	2603 reflections with I > 2.0σ(I)
Graphite monochromator	R_int = 0.033
ϕ & ω scans	θ_max = 27.1°, θ_min = 2.2°
Absorption correction: multi-scan SADABS (Siemens, 1996)	h = −12→12
T_min = 0.83, T_max = 0.97	k = −9→9
26105 measured reflections	l = −23→21
2636 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.027	Method = Modified Sheldrick w = 1/[σ²(F²) + ( 0.06P)² + 0.09P] , where P = (max(F_o²,0) + 2F_c²)/3
wR(F²) = 0.080	(Δ/σ)_max = 0.009
S = 1.01	Δρ_max = 0.18 e Å⁻³
2628 reflections	Δρ_min = −0.10 e Å⁻³
171 parameters	Absolute structure: Flack (1983), 1254 Friedel-pairs
158 restraints	Absolute structure parameter: 0.04 (5)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₁H₁₆NO₂·Cl	V = 1217.77 (3) Å³
M_r = 229.71	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 9.4272 (2) Å	µ = 0.30 mm⁻¹
b = 7.0774 (2) Å	T = 293 K
c = 18.2519 (4) Å	0.35 × 0.22 × 0.10 mm

Data collection top

Bruker Kappa Apex2 diffractometer	2636 independent reflections
Absorption correction: multi-scan SADABS (Siemens, 1996)	2603 reflections with I > 2.0σ(I)
T_min = 0.83, T_max = 0.97	R_int = 0.033
26105 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.080	Δρ_max = 0.18 e Å⁻³
S = 1.01	Δρ_min = −0.10 e Å⁻³
2628 reflections	Absolute structure: Flack (1983), 1254 Friedel-pairs
171 parameters	Absolute structure parameter: 0.04 (5)
158 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.46884 (17)	−0.0934 (2)	0.56988 (14)	0.0515
C2	0.52169 (19)	0.0843 (2)	0.58072 (15)	0.0608
C3	0.49604 (18)	0.1650 (2)	0.64918 (16)	0.0559
C4	0.42239 (14)	0.07054 (19)	0.70375 (14)	0.0455
C5	0.37103 (16)	−0.1112 (2)	0.69111 (15)	0.0501
C6	0.39546 (18)	−0.1878 (2)	0.62345 (15)	0.0511
C70	0.4116 (8)	−0.3789 (9)	0.5264 (4)	0.0809	0.82 (2)
C71	0.4027 (15)	−0.366 (3)	0.5238 (8)	0.0494	0.18 (2)
C8	0.39360 (15)	0.1602 (2)	0.77726 (15)	0.0514
C9	0.23673 (13)	0.21343 (18)	0.78510 (14)	0.0426
C10	0.1900 (2)	0.3672 (2)	0.73245 (15)	0.0589
C11	0.2240 (2)	0.1351 (2)	0.91961 (15)	0.0628
O20	0.3447 (11)	−0.3585 (6)	0.5969 (3)	0.0734	0.82 (2)
O21	0.394 (2)	−0.3744 (13)	0.6025 (7)	0.0490	0.18 (2)
O10	0.4718 (9)	−0.1993 (6)	0.5059 (2)	0.0662	0.82 (2)
O11	0.509 (2)	−0.224 (2)	0.5177 (9)	0.0574	0.18 (2)
N1	0.20781 (13)	0.27940 (15)	0.86126 (13)	0.0453
Cl1	0.38749 (3)	0.64748 (5)	0.88572 (12)	0.0537
H21	0.5767	0.1520	0.5449	0.0729*
H31	0.5333	0.2873	0.6590	0.0667*
H51	0.3254	−0.1811	0.7283	0.0614*
H701	0.4857	−0.4783	0.5287	0.0959*	0.82 (2)
H702	0.3346	−0.4154	0.4926	0.0954*	0.82 (2)
H711	0.4345	−0.4845	0.5022	0.0570*	0.18 (2)
H712	0.3140	−0.3288	0.5018	0.0570*	0.18 (2)
H81	0.4135	0.0684	0.8133	0.0616*
H82	0.4539	0.2703	0.7869	0.0621*
H91	0.1795	0.0991	0.7794	0.0525*
H103	0.0910	0.3990	0.7394	0.0889*
H102	0.2476	0.4801	0.7444	0.0896*
H101	0.2068	0.3338	0.6816	0.0887*
H111	0.1849	0.1767	0.9645	0.0956*
H112	0.3205	0.1016	0.9236	0.0953*
H113	0.1732	0.0301	0.9016	0.0954*
H11	0.2646 (18)	0.381 (2)	0.8711 (9)	0.0681*
H12	0.1157 (16)	0.316 (2)	0.8628 (9)	0.0667*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0574 (9)	0.0525 (7)	0.0447 (7)	0.0048 (6)	0.0021 (6)	−0.0005 (6)
C2	0.0672 (10)	0.0595 (8)	0.0556 (8)	−0.0123 (7)	0.0105 (7)	0.0036 (7)
C3	0.0505 (8)	0.0506 (8)	0.0666 (9)	−0.0104 (6)	0.0046 (7)	−0.0050 (6)
C4	0.0382 (6)	0.0466 (6)	0.0518 (7)	0.0053 (5)	−0.0035 (6)	−0.0051 (6)
C5	0.0591 (8)	0.0407 (6)	0.0506 (8)	0.0011 (5)	0.0092 (6)	0.0019 (5)
C6	0.0642 (9)	0.0372 (6)	0.0520 (7)	0.0015 (5)	0.0034 (6)	−0.0012 (5)
C70	0.121 (4)	0.062 (2)	0.060 (2)	−0.010 (2)	0.017 (2)	−0.0145 (15)
C71	0.046 (6)	0.050 (5)	0.052 (4)	0.020 (4)	−0.017 (5)	−0.011 (4)
C8	0.0419 (7)	0.0594 (9)	0.0528 (8)	0.0026 (5)	−0.0034 (6)	−0.0126 (6)
C9	0.0411 (6)	0.0363 (6)	0.0505 (7)	−0.0027 (5)	−0.0026 (5)	−0.0036 (5)
C10	0.0612 (9)	0.0594 (8)	0.0561 (9)	0.0074 (7)	−0.0058 (7)	0.0098 (7)
C11	0.0659 (10)	0.0661 (10)	0.0562 (9)	0.0122 (7)	0.0042 (8)	0.0115 (7)
O20	0.102 (4)	0.0455 (11)	0.0722 (15)	−0.0127 (14)	0.0227 (19)	−0.0153 (9)
O21	0.058 (7)	0.032 (3)	0.057 (4)	0.002 (3)	0.015 (4)	−0.002 (3)
O10	0.091 (3)	0.0622 (12)	0.0458 (13)	0.0004 (13)	0.0024 (13)	−0.0052 (10)
O11	0.065 (7)	0.079 (7)	0.029 (5)	0.001 (4)	0.004 (4)	0.002 (4)
N1	0.0431 (5)	0.0386 (5)	0.0541 (6)	−0.0012 (4)	0.0034 (5)	−0.0028 (4)
Cl1	0.04745 (17)	0.04743 (18)	0.0661 (2)	−0.00972 (12)	0.00585 (18)	−0.00432 (16)

Geometric parameters (Å, º) top

C1—C2	1.368 (2)	C71—H711	0.973
C1—C6	1.372 (2)	C71—H712	0.964
C1—O10	1.388 (3)	C8—C9	1.5329 (19)
C2—C3	1.395 (3)	C8—H81	0.943
C2—H21	0.963	C8—H82	0.980
C3—C4	1.386 (2)	C9—C10	1.517 (2)
C3—H31	0.951	C9—N1	1.4915 (19)
C4—C5	1.393 (2)	C9—H91	0.978
C4—C8	1.509 (2)	C10—H103	0.968
C5—C6	1.368 (2)	C10—H102	0.991
C5—H51	0.943	C10—H101	0.972
C6—O20	1.387 (3)	C11—N1	1.483 (2)
C70—O20	1.440 (5)	C11—H111	0.945
C70—O10	1.441 (4)	C11—H112	0.943
C70—H701	0.992	C11—H113	0.943
C70—H702	0.987	N1—H11	0.916 (14)
C71—O21	1.439 (9)	N1—H12	0.907 (15)
C71—O11	1.428 (9)

C2—C1—C6	121.92 (14)	C9—C8—H81	107.2
C2—C1—O10	127.7 (2)	C4—C8—H82	112.9
C6—C1—O10	110.3 (2)	C9—C8—H82	110.3
C1—C2—C3	116.30 (14)	H81—C8—H82	107.8
C1—C2—H21	123.7	C8—C9—C10	113.43 (13)
C3—C2—H21	119.9	C8—C9—N1	109.89 (12)
C2—C3—C4	122.22 (14)	C10—C9—N1	108.22 (11)
C2—C3—H31	118.5	C8—C9—H91	108.6
C4—C3—H31	119.2	C10—C9—H91	111.5
C3—C4—C5	120.01 (14)	N1—C9—H91	104.9
C3—C4—C8	121.76 (13)	C9—C10—H103	111.4
C5—C4—C8	118.23 (14)	C9—C10—H102	106.2
C4—C5—C6	117.19 (14)	H103—C10—H102	108.2
C4—C5—H51	121.6	C9—C10—H101	112.6
C6—C5—H51	121.2	H103—C10—H101	109.8
C1—C6—C5	122.35 (14)	H102—C10—H101	108.5
C1—C6—O20	110.5 (2)	N1—C11—H111	111.5
C5—C6—O20	127.1 (2)	N1—C11—H112	109.2
O20—C70—O10	108.5 (4)	H111—C11—H112	112.8
O20—C70—H701	110.0	N1—C11—H113	103.9
O10—C70—H701	111.1	H111—C11—H113	110.4
O20—C70—H702	105.2	H112—C11—H113	108.6
O10—C70—H702	110.9	C70—O20—C6	104.4 (4)
H701—C70—H702	111.0	C71—O21—C6	103.8 (12)
O21—C71—O11	98.4 (16)	C70—O10—C1	104.4 (4)
O21—C71—H711	112.8	C71—O11—C1	102.8 (13)
O11—C71—H711	111.0	C9—N1—C11	115.78 (11)
O21—C71—H712	112.3	C9—N1—H12	107.1 (11)
O11—C71—H712	112.5	C11—N1—H12	105.9 (11)
H711—C71—H712	109.5	C9—N1—H11	108.8 (10)
C4—C8—C9	111.09 (12)	C11—N1—H11	110.0 (10)
C4—C8—H81	107.1	H12—N1—H11	109.1 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H112···O10ⁱ	0.94	2.56	3.303 (5)	136 (1)
C11—H112···O11ⁱ	0.94	2.50	3.149 (5)	126 (1)

Symmetry code: (i) −x+1, −y, z+1/2.

(2) top

Crystal data top

C₁₁H₁₆NO₂·Cl	F(000) = 488
M_r = 229.71	D_x = 1.351 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2684 reflections
a = 9.1478 (3) Å	θ = 4–23°
b = 6.9826 (3) Å	µ = 0.32 mm⁻¹
c = 17.6799 (4) Å	T = 293 K
V = 1129.31 (3) Å³	Block, colourless
Z = 4	0.20 × 0.10 × 0.05 mm

Data collection top

Bruker Kappa Apex2 diffractometer	977 reflections with I > 2.0σ(I)
Graphite monochromator	R_int = 0.033
ω scans	θ_max = 23.3°, θ_min = 3.7°
Absorption correction: multi-scan SADABS (Siemens, 1996)	h = −9→9
T_min = 0.87, T_max = 0.98	k = −6→6
5069 measured reflections	l = −19→19
1027 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.035	Method = Modified Sheldrick w = 1/[σ²(F²) + ( 0.03P)² + 0.9P] , where P = (max(F_o²,0) + 2F_c²)/3
wR(F²) = 0.081	(Δ/σ)_max = 0.002
S = 1.04	Δρ_max = 0.61 e Å⁻³
1023 reflections	Δρ_min = −0.57 e Å⁻³
86 parameters	Absolute structure: Flack (1983), 355 Friedel-pairs
56 restraints	Absolute structure parameter: 0.07 (11)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₁H₁₆NO₂·Cl	V = 1129.31 (3) Å³
M_r = 229.71	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 9.1478 (3) Å	µ = 0.32 mm⁻¹
b = 6.9826 (3) Å	T = 293 K
c = 17.6799 (4) Å	0.20 × 0.10 × 0.05 mm

Data collection top

Bruker Kappa Apex2 diffractometer	1027 independent reflections
Absorption correction: multi-scan SADABS (Siemens, 1996)	977 reflections with I > 2.0σ(I)
T_min = 0.87, T_max = 0.98	R_int = 0.033
5069 measured reflections	θ_max = 23.3°

Refinement top

R[F² > 2σ(F²)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.081	Δρ_max = 0.61 e Å⁻³
S = 1.04	Δρ_min = −0.57 e Å⁻³
1023 reflections	Absolute structure: Flack (1983), 355 Friedel-pairs
86 parameters	Absolute structure parameter: 0.07 (11)
56 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.4840 (4)	−0.1067 (7)	0.5663 (2)	0.0404 (8)*
C2	0.5395 (5)	0.0729 (7)	0.5766 (2)	0.0432 (8)*
C3	0.5106 (5)	0.1607 (7)	0.6457 (2)	0.0425 (9)*
C4	0.4309 (4)	0.0697 (7)	0.7015 (2)	0.0367 (7)*
C5	0.3755 (4)	−0.1115 (7)	0.6890 (2)	0.0405 (8)*
C6	0.4039 (5)	−0.1966 (7)	0.6209 (2)	0.0407 (8)*
C71	0.4110 (13)	−0.3862 (18)	0.5203 (5)	0.0451 (17)*	0.49 (2)
C70	0.4407 (13)	−0.4017 (14)	0.5273 (6)	0.0446 (15)*	0.51 (2)
C8	0.3976 (4)	0.1664 (7)	0.7762 (2)	0.0405 (8)*
C9	0.2357 (4)	0.2157 (7)	0.7833 (2)	0.0390 (8)*
C10	0.1907 (5)	0.3747 (7)	0.7304 (2)	0.0469 (10)*
C11	0.2093 (5)	0.1243 (8)	0.9195 (2)	0.0474 (10)*
O20	0.3422 (11)	−0.3618 (11)	0.5902 (4)	0.0426 (13)*	0.51 (2)
O21	0.3833 (13)	−0.3852 (10)	0.6022 (4)	0.0445 (18)*	0.49 (2)
O10	0.4755 (12)	−0.2136 (11)	0.4999 (3)	0.0419 (13)*	0.51 (2)
O11	0.5175 (12)	−0.2334 (11)	0.5074 (4)	0.0436 (18)*	0.49 (2)
N1	0.2002 (4)	0.2734 (5)	0.86214 (18)	0.0410 (7)*
Cl1	0.37173 (11)	0.65593 (17)	0.88476 (10)	0.0456
H21	0.5962	0.1336	0.5397	0.0504*
H31	0.5449	0.2838	0.6545	0.0492*
H51	0.3197	−0.1732	0.7254	0.0492*
H711	0.4565	−0.5075	0.5070	0.0513*	0.49 (2)
H712	0.3233	−0.3675	0.4906	0.0510*	0.49 (2)
H701	0.5284	−0.4640	0.5450	0.0531*	0.51 (2)
H702	0.3936	−0.4793	0.4882	0.0533*	0.51 (2)
H81	0.4238	0.0816	0.8175	0.0477*
H82	0.4537	0.2845	0.7801	0.0480*
H91	0.1766	0.1009	0.7718	0.0481*
H103	0.0886	0.4015	0.7367	0.0689*
H102	0.2459	0.4891	0.7404	0.0687*
H101	0.2073	0.3378	0.6795	0.0686*
H111	0.1699	0.1715	0.9662	0.0702*
H112	0.3092	0.0906	0.9273	0.0700*
H113	0.1549	0.0155	0.9021	0.0699*
H11	0.256 (3)	0.373 (3)	0.8761 (12)	0.0617*
H12	0.114 (2)	0.325 (4)	0.8620 (12)	0.0625*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0409 (7)	0.0401 (9)	0.0558 (5)	−0.0069 (5)	0.0028 (5)	−0.0021 (6)

Geometric parameters (Å, º) top

C1—C2	1.365 (6)	C70—H701	0.965
C1—C6	1.366 (6)	C70—H702	0.978
C1—O10	1.394 (6)	C8—C9	1.525 (5)
C2—C3	1.392 (5)	C8—H81	0.970
C2—H21	0.934	C8—H82	0.973
C3—C4	1.381 (6)	C9—C10	1.509 (6)
C3—H31	0.928	C9—N1	1.487 (5)
C4—C5	1.381 (6)	C9—H91	0.988
C4—C8	1.515 (5)	C10—H103	0.959
C5—C6	1.367 (6)	C10—H102	0.961
C5—H51	0.927	C10—H101	0.948
C6—O20	1.394 (7)	C11—N1	1.456 (5)
C71—O21	1.470 (8)	C11—H111	0.960
C71—O11	1.462 (8)	C11—H112	0.953
C71—H711	0.973	C11—H113	0.959
C71—H712	0.968	N1—H11	0.896 (19)
C70—O20	1.459 (8)	N1—H12	0.871 (19)
C70—O10	1.436 (8)

C2—C1—C6	121.8 (4)	C9—C8—H81	108.4
C2—C1—O10	128.7 (4)	C4—C8—H82	109.5
C6—C1—O10	108.6 (5)	C9—C8—H82	108.4
C1—C2—C3	116.8 (4)	H81—C8—H82	109.4
C1—C2—H21	122.0	C8—C9—C10	112.3 (3)
C3—C2—H21	121.2	C8—C9—N1	110.6 (3)
C2—C3—C4	121.6 (4)	C10—C9—N1	108.8 (3)
C2—C3—H31	119.4	C8—C9—H91	109.3
C4—C3—H31	119.0	C10—C9—H91	108.6
C3—C4—C5	120.1 (4)	N1—C9—H91	107.1
C3—C4—C8	121.6 (4)	C9—C10—H103	109.7
C5—C4—C8	118.3 (4)	C9—C10—H102	110.7
C4—C5—C6	118.0 (4)	H103—C10—H102	109.1
C4—C5—H51	121.1	C9—C10—H101	110.2
C6—C5—H51	120.9	H103—C10—H101	108.6
C5—C6—C1	121.7 (4)	H102—C10—H101	108.5
C5—C6—O20	128.7 (5)	N1—C11—H111	109.4
C1—C6—O20	108.8 (4)	N1—C11—H112	109.4
O21—C71—O11	105.4 (7)	H111—C11—H112	108.7
O21—C71—H711	108.4	N1—C11—H113	108.3
O11—C71—H711	108.2	H111—C11—H113	110.7
O21—C71—H712	113.0	H112—C11—H113	110.4
O11—C71—H712	111.7	C70—O20—C6	101.8 (7)
H711—C71—H712	109.9	C71—O21—C6	102.7 (7)
O20—C70—O10	102.7 (7)	C70—O10—C1	102.6 (7)
O20—C70—H701	110.6	C71—O11—C1	101.5 (7)
O10—C70—H701	109.7	C9—N1—C11	116.5 (4)
O20—C70—H702	111.9	C9—N1—H11	110.0 (15)
O10—C70—H702	111.5	C11—N1—H11	109.2 (15)
H701—C70—H702	110.2	C9—N1—H12	108.0 (15)
C4—C8—C9	111.6 (3)	C11—N1—H12	110.6 (15)
C4—C8—H81	109.6	H11—N1—H12	101.4 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H112···O10ⁱ	0.95	2.50	3.275 (8)	138 (1)
C11—H112···O11ⁱ	0.95	2.35	3.040 (8)	129 (1)

Symmetry code: (i) −x+1, −y, z+1/2.

(3) top

Crystal data top

C₁₁H₁₆NO₂·Cl	F(000) = 488.000
M_r = 229.71	D_x = 1.449 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2309 reflections
a = 8.8661 (5) Å	θ = 3–23°
b = 6.9379 (4) Å	µ = 0.34 mm⁻¹
c = 17.120 (3) Å	T = 293 K
V = 1053.08 (17) Å³	Block, colourless
Z = 4	0.20 × 0.10 × 0.05 mm

Data collection top

Bruker Kappa Apex2 diffractometer	530 reflections with I > 2.0σ(I)
Graphite monochromator	R_int = 0.038
ω scans	θ_max = 23.3°, θ_min = 2.9°
Absorption correction: multi-scan SADABS (Siemens, 1996)	h = −9→9
T_min = 0.87, T_max = 0.98	k = −7→7
4833 measured reflections	l = −5→5
572 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.031	Method = Modified Sheldrick w = 1/[σ²(F²) + ( 0.02P)² + 1.18P] , where P = (max(F_o²,0) + 2F_c²)/3
wR(F²) = 0.071	(Δ/σ)_max = 0.001
S = 1.02	Δρ_max = 0.23 e Å⁻³
567 reflections	Δρ_min = −0.22 e Å⁻³
86 parameters	Absolute structure: Flack (1983), 455 Friedel-pairs
56 restraints	Absolute structure parameter: 0.19 (16)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₁H₁₆NO₂·Cl	V = 1053.08 (17) Å³
M_r = 229.71	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 8.8661 (5) Å	µ = 0.34 mm⁻¹
b = 6.9379 (4) Å	T = 293 K
c = 17.120 (3) Å	0.20 × 0.10 × 0.05 mm

Data collection top

Bruker Kappa Apex2 diffractometer	572 independent reflections
Absorption correction: multi-scan SADABS (Siemens, 1996)	530 reflections with I > 2.0σ(I)
T_min = 0.87, T_max = 0.98	R_int = 0.038
4833 measured reflections	θ_max = 23.3°

Refinement top

R[F² > 2σ(F²)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.071	Δρ_max = 0.23 e Å⁻³
S = 1.02	Δρ_min = −0.22 e Å⁻³
567 reflections	Absolute structure: Flack (1983), 455 Friedel-pairs
86 parameters	Absolute structure parameter: 0.19 (16)
56 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.4972 (5)	−0.1158 (7)	0.5578 (6)	0.0322 (9)*
C2	0.5542 (5)	0.0698 (7)	0.5680 (9)	0.0336 (10)*
C3	0.5192 (5)	0.1575 (7)	0.6375 (8)	0.0306 (10)*
C4	0.4342 (5)	0.0717 (7)	0.6956 (8)	0.0297 (9)*
C5	0.3787 (5)	−0.1159 (7)	0.6844 (8)	0.0316 (10)*
C6	0.4123 (5)	−0.1995 (6)	0.6129 (8)	0.0299 (9)*
C70	0.4608 (16)	−0.4129 (17)	0.5267 (14)	0.0338 (16)*	0.50 (3)
C71	0.4283 (15)	−0.4054 (19)	0.5124 (12)	0.0311 (19)*	0.50 (3)
C8	0.4028 (5)	0.1669 (7)	0.7719 (9)	0.0340 (10)*
C9	0.2327 (5)	0.2171 (7)	0.7757 (10)	0.0322 (9)*
C10	0.1892 (5)	0.3796 (7)	0.7217 (8)	0.0348 (11)*
C11	0.1962 (5)	0.1166 (7)	0.9177 (8)	0.0381 (11)*
O20	0.3472 (14)	−0.3704 (12)	0.5847 (11)	0.0307 (14)*	0.50 (3)
O21	0.3866 (15)	−0.3908 (10)	0.5935 (11)	0.027 (2)*	0.50 (3)
O10	0.4899 (17)	−0.2259 (12)	0.4918 (7)	0.0333 (15)*	0.50 (3)
O11	0.5327 (15)	−0.2457 (13)	0.5001 (9)	0.032 (2)*	0.50 (3)
N1	0.1936 (4)	0.2741 (5)	0.8597 (8)	0.0327 (9)*
Cl1	0.35506 (12)	0.66293 (14)	0.8798 (3)	0.0396
H21	0.6112	0.1381	0.5331	0.0729*
H31	0.5516	0.2822	0.6472	0.0667*
H51	0.3310	−0.1858	0.7208	0.0614*
H701	0.5374	−0.5084	0.5322	0.0959*	0.50 (3)
H702	0.3888	−0.4554	0.4909	0.0954*	0.50 (3)
H81	0.4214	0.0784	0.8095	0.0616*
H82	0.4586	0.2806	0.7822	0.0621*
H91	0.1797	0.0995	0.7695	0.0525*
H103	0.0886	0.4068	0.7253	0.0889*
H102	0.2420	0.4962	0.7342	0.0896*
H101	0.2128	0.3440	0.6717	0.0887*
H111	0.1508	0.1589	0.9609	0.0956*
H112	0.2932	0.0883	0.9250	0.0953*
H113	0.1507	0.0079	0.8993	0.0954*
H11	0.254 (3)	0.372 (3)	0.8754 (17)	0.0681*
H12	0.102 (2)	0.326 (4)	0.8601 (18)	0.0667*
H711	0.5050	−0.5009	0.5179	0.0512*	0.50 (3)
H712	0.3563	−0.4480	0.4767	0.0512*	0.50 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0386 (6)	0.0306 (5)	0.049 (6)	−0.0062 (5)	0.0010 (15)	−0.0022 (14)

Geometric parameters (Å, º) top

C1—C2	1.394 (7)	C71—H711	0.954
C1—C6	1.341 (13)	C71—H712	0.932
C1—O10	1.366 (9)	C8—C9	1.549 (7)
C2—C3	1.373 (19)	C8—H81	0.904
C2—H21	0.914	C8—H82	0.948
C3—C4	1.382 (14)	C9—C10	1.509 (15)
C3—H31	0.927	C9—N1	1.532 (19)
C4—C5	1.405 (7)	C9—H91	0.948
C4—C8	1.490 (18)	C10—H103	0.914
C5—C6	1.386 (17)	C10—H102	0.959
C5—H51	0.897	C10—H101	0.915
C6—O20	1.404 (8)	C11—N1	1.477 (13)
C70—O20	1.445 (9)	C11—H111	0.892
C70—O10	1.451 (9)	C11—H112	0.891
C70—H701	0.954	C11—H113	0.911
C70—H702	0.932	N1—H11	0.905 (19)
C71—O21	1.440 (10)	N1—H12	0.889 (19)
C71—O11	1.459 (8)

C2—C1—C6	121.1 (9)	C9—C8—H81	107.5
C2—C1—O10	129.6 (10)	C4—C8—H82	115.7
C6—C1—O10	108.3 (6)	C9—C8—H82	108.3
C1—C2—C3	115.8 (9)	H81—C8—H82	109.7
C1—C2—H21	126.6	C8—C9—C10	113.0 (8)
C3—C2—H21	117.5	C8—C9—N1	108.5 (10)
C2—C3—C4	123.8 (6)	C10—C9—N1	108.9 (7)
C2—C3—H31	119.9	C8—C9—H91	106.5
C4—C3—H31	116.3	C10—C9—H91	116.6
C3—C4—C5	119.4 (10)	N1—C9—H91	102.4
C3—C4—C8	122.8 (6)	C9—C10—H103	111.3
C5—C4—C8	117.7 (9)	C9—C10—H102	111.7
C4—C5—C6	115.7 (9)	H103—C10—H102	106.7
C4—C5—H51	124.8	C9—C10—H101	108.2
C6—C5—H51	119.3	H103—C10—H101	110.0
C5—C6—C1	124.1 (5)	H102—C10—H101	109.0
C5—C6—O20	124.7 (9)	N1—C11—H111	107.9
C1—C6—O20	110.8 (10)	N1—C11—H112	105.8
O20—C70—O10	103.0 (11)	H111—C11—H112	113.1
O20—C70—H701	124.7	N1—C11—H113	111.9
O10—C70—H701	122.3	H111—C11—H113	111.1
O20—C70—H702	92.2	H112—C11—H113	107.1
O10—C70—H702	97.8	C70—O20—C6	97.0 (12)
H701—C70—H702	109.5	C71—O21—C6	104.9 (13)
O21—C71—O11	104.3 (13)	C70—O10—C1	99.7 (12)
O21—C71—H711	97.8	C71—O11—C1	104.5 (10)
O11—C71—H711	95.2	C9—N1—C11	115.9 (6)
O21—C71—H712	118.6	C9—N1—H11	109.9 (16)
O11—C71—H712	125.5	C11—N1—H11	110.4 (16)
H711—C71—H712	109.5	C9—N1—H12	108.6 (17)
C4—C8—C9	108.6 (9)	C11—N1—H12	107.9 (16)
C4—C8—H81	106.8	H11—N1—H12	103.4 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H112···O10ⁱ	0.89	2.43	3.150 (13)	138 (1)
C11—H112···O11ⁱ	0.89	2.29	2.928 (13)	129 (1)
C11—H113···O10ⁱⁱ	0.91	2.59	3.159 (13)	121 (1)

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

(4) top

Crystal data top

C₁₁H₁₆NO₂·Cl	F(000) = 488
M_r = 229.71	D_x = 1.572 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2595 reflections
a = 8.4895 (2) Å	θ = 3–23°
b = 6.8759 (2) Å	µ = 0.37 mm⁻¹
c = 16.6225 (14) Å	T = 293 K
V = 970.30 (8) Å³	Block, colourless
Z = 4	0.2 × 0.1 × 0.05 mm

Data collection top

Bruker Kappa Apex2 diffractometer	498 reflections with I > 2.0σ(I)
Graphite monochromator	R_int = 0.032
ω scans	θ_max = 23.2°, θ_min = 3.0°
Absorption correction: multi-scan SADABS (Siemens, 1996)	h = −9→9
T_min = 0.89, T_max = 0.96	k = −7→7
4431 measured reflections	l = −5→5
522 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.027	Method = Modified Sheldrick w = 1/[σ²(F²) + ( 0.02P)² + 1.4P] , where P = (max(F_o²,0) + 2F_c²)/3
wR(F²) = 0.062	(Δ/σ)_max = 0.003
S = 0.97	Δρ_max = 0.14 e Å⁻³
518 reflections	Δρ_min = −0.12 e Å⁻³
86 parameters	Absolute structure: Flack (1983), 50 Friedel-pairs
56 restraints	Absolute structure parameter: −0.02 (15)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₁H₁₆NO₂·Cl	V = 970.30 (8) Å³
M_r = 229.71	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 8.4895 (2) Å	µ = 0.37 mm⁻¹
b = 6.8759 (2) Å	T = 293 K
c = 16.6225 (14) Å	0.2 × 0.1 × 0.05 mm

Data collection top

Bruker Kappa Apex2 diffractometer	522 independent reflections
Absorption correction: multi-scan SADABS (Siemens, 1996)	498 reflections with I > 2.0σ(I)
T_min = 0.89, T_max = 0.96	R_int = 0.032
4431 measured reflections	θ_max = 23.2°

Refinement top

R[F² > 2σ(F²)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.062	Δρ_max = 0.14 e Å⁻³
S = 0.97	Δρ_min = −0.12 e Å⁻³
518 reflections	Absolute structure: Flack (1983), 50 Friedel-pairs
86 parameters	Absolute structure parameter: −0.02 (15)
56 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.5100 (5)	−0.1215 (6)	0.5556 (5)	0.0243 (8)*
C2	0.5685 (5)	0.0663 (6)	0.5647 (7)	0.0264 (9)*
C3	0.5287 (5)	0.1598 (6)	0.6342 (8)	0.0235 (9)*
C4	0.4407 (5)	0.0739 (6)	0.6955 (7)	0.0220 (9)*
C5	0.3832 (5)	−0.1155 (7)	0.6853 (8)	0.0235 (9)*
C6	0.4189 (5)	−0.2033 (5)	0.6132 (7)	0.0222 (9)*
C70	0.4747 (16)	−0.4242 (16)	0.5241 (15)	0.0245 (15)*	0.51 (4)
C71	0.4456 (18)	−0.4235 (19)	0.5124 (12)	0.0243 (18)*	0.49 (4)
C8	0.4059 (5)	0.1720 (6)	0.7730 (8)	0.0267 (9)*
C9	0.2299 (5)	0.2222 (6)	0.7772 (9)	0.0267 (9)*
C10	0.1866 (4)	0.3874 (6)	0.7192 (8)	0.0280 (10)*
C11	0.1832 (5)	0.1150 (6)	0.9168 (8)	0.0294 (10)*
O20	0.3592 (14)	−0.3788 (12)	0.5844 (11)	0.0222 (14)*	0.51 (4)
O21	0.3899 (17)	−0.3958 (12)	0.5929 (12)	0.0229 (19)*	0.49 (4)
O10	0.5080 (19)	−0.2359 (12)	0.4882 (7)	0.0243 (14)*	0.51 (4)
O11	0.5452 (17)	−0.2535 (14)	0.4955 (9)	0.0232 (19)*	0.49 (4)
N1	0.1850 (4)	0.2763 (4)	0.8623 (8)	0.0268 (8)*
Cl1	0.33369 (11)	0.67223 (12)	0.8790 (3)	0.0353
H21	0.6299	0.1272	0.5258	0.0398*
H31	0.5634	0.2864	0.6420	0.0370*
H51	0.3238	−0.1797	0.7243	0.0381*
H701	0.5692	−0.4722	0.5505	0.0400*	0.51 (4)
H702	0.4382	−0.5182	0.4847	0.0401*	0.51 (4)
H711	0.5039	−0.5434	0.5046	0.0361*	0.49 (4)
H712	0.3558	−0.4203	0.4763	0.0360*	0.49 (4)
H81	0.4332	0.0893	0.8181	0.0401*
H82	0.4681	0.2911	0.7768	0.0399*
H91	0.1728	0.1047	0.7622	0.0390*
H102	0.0744	0.4089	0.7206	0.0521*
H101	0.2394	0.5035	0.7359	0.0519*
H103	0.2187	0.3554	0.6655	0.0520*
H112	0.1855	0.1696	0.9700	0.0560*
H113	0.2740	0.0347	0.9088	0.0560*
H111	0.0909	0.0355	0.9111	0.0560*
H11	0.252 (3)	0.369 (3)	0.8805 (17)	0.0402*
H12	0.090 (2)	0.325 (3)	0.8611 (18)	0.0402*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0324 (5)	0.0233 (5)	0.050 (5)	−0.0052 (4)	−0.0003 (13)	−0.0016 (13)

Geometric parameters (Å, º) top

C1—C2	1.392 (6)	C71—H711	0.970
C1—C6	1.353 (11)	C71—H712	0.970
C1—O10	1.370 (9)	C8—C9	1.535 (6)
C2—C3	1.364 (16)	C8—H81	0.969
C2—H21	0.930	C8—H82	0.977
C3—C4	1.394 (13)	C9—C10	1.534 (14)
C3—H31	0.928	C9—N1	1.512 (18)
C4—C5	1.401 (7)	C9—H91	0.975
C4—C8	1.484 (15)	C10—H102	0.964
C5—C6	1.375 (16)	C10—H101	0.957
C5—H51	0.933	C10—H103	0.959
C6—O20	1.394 (8)	C11—N1	1.431 (12)
C70—O20	1.437 (9)	C11—H112	0.961
C70—O10	1.453 (8)	C11—H113	0.957
C70—H701	0.973	C11—H111	0.960
C70—H702	0.971	N1—H11	0.904 (18)
C71—O21	1.432 (9)	N1—H12	0.873 (18)
C71—O11	1.469 (8)

C2—C1—C6	120.9 (8)	C9—C8—H81	109.2
C2—C1—O10	128.7 (8)	C4—C8—H82	109.3
C6—C1—O10	109.5 (6)	C9—C8—H82	109.6
C1—C2—C3	116.1 (8)	H81—C8—H82	108.2
C1—C2—H21	122.9	C8—C9—C10	111.8 (8)
C3—C2—H21	121.0	C8—C9—N1	110.1 (10)
C2—C3—C4	123.5 (5)	C10—C9—N1	110.2 (6)
C2—C3—H31	118.8	C8—C9—H91	106.6
C4—C3—H31	117.7	C10—C9—H91	109.5
C3—C4—C5	119.5 (9)	N1—C9—H91	108.5
C3—C4—C8	123.3 (5)	C9—C10—H102	109.6
C5—C4—C8	117.3 (9)	C9—C10—H101	108.8
C4—C5—C6	115.9 (8)	H102—C10—H101	109.2
C4—C5—H51	123.0	C9—C10—H103	110.3
C6—C5—H51	121.1	H102—C10—H103	109.8
C5—C6—C1	124.0 (4)	H101—C10—H103	109.2
C5—C6—O20	126.8 (8)	N1—C11—H112	106.2
C1—C6—O20	108.9 (9)	N1—C11—H113	110.6
O20—C70—O10	103.1 (11)	H112—C11—H113	109.6
O20—C70—H701	108.7	N1—C11—H111	112.8
O10—C70—H701	109.1	H112—C11—H111	109.2
O20—C70—H702	113.4	H113—C11—H111	108.4
O10—C70—H702	112.3	C70—O20—C6	100.4 (11)
H701—C70—H702	110.0	C71—O21—C6	107.2 (13)
O21—C71—O11	105.2 (13)	C70—O10—C1	100.3 (12)
O21—C71—H711	113.9	C71—O11—C1	105.1 (10)
O11—C71—H711	110.9	C9—N1—C11	113.8 (6)
O21—C71—H712	108.4	C9—N1—H11	109.2 (16)
O11—C71—H712	108.5	C11—N1—H11	110.0 (15)
H711—C71—H712	109.7	C9—N1—H12	107.7 (17)
C4—C8—C9	109.6 (8)	C11—N1—H12	107.8 (15)
C4—C8—H81	110.9	H11—N1—H12	108.1 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H91···C4ⁱ	0.98	2.57	3.467 (12)	152 (1)
C11—H111···O10ⁱⁱ	0.96	2.42	3.141 (12)	132 (1)

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

(5) top

Crystal data top

C₁₁H₁₆NO₂·Cl	F(000) = 488
M_r = 229.71	D_x = 1.602 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2286 reflections
a = 8.4043 (2) Å	θ = 4–23°
b = 6.8578 (2) Å	µ = 0.38 mm⁻¹
c = 16.5271 (12) Å	T = 293 K
V = 952.54 (7) Å³	Block, colourless
Z = 4	0.2 × 0.1 × 0.05 mm

Data collection top

Bruker Kappa Apex2 diffractometer	459 reflections with I > 2.0σ(I)
Graphite monochromator	R_int = 0.033
ω scans	θ_max = 23.2°, θ_min = 3.8°
Absorption correction: multi-scan SADABS (Siemens, 1996)	h = −9→9
T_min = 0.91, T_max = 0.96	k = −7→7
4206 measured reflections	l = −5→5
493 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.022	Method = Modified Sheldrick w = 1/[σ²(F²) + ( 0.01P)² + 0.9P] , where P = (max(F_o²,0) + 2F_c²)/3
wR(F²) = 0.055	(Δ/σ)_max = 0.0003
S = 1.02	Δρ_max = 0.20 e Å⁻³
489 reflections	Δρ_min = −0.22 e Å⁻³
86 parameters	Absolute structure: Flack (1983), 29 Friedel-pairs
56 restraints	Absolute structure parameter: 0.04 (13)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₁H₁₆NO₂·Cl	V = 952.54 (7) Å³
M_r = 229.71	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 8.4043 (2) Å	µ = 0.38 mm⁻¹
b = 6.8578 (2) Å	T = 293 K
c = 16.5271 (12) Å	0.2 × 0.1 × 0.05 mm

Data collection top

Bruker Kappa Apex2 diffractometer	493 independent reflections
Absorption correction: multi-scan SADABS (Siemens, 1996)	459 reflections with I > 2.0σ(I)
T_min = 0.91, T_max = 0.96	R_int = 0.033
4206 measured reflections	θ_max = 23.2°

Refinement top

R[F² > 2σ(F²)] = 0.022	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.055	Δρ_max = 0.20 e Å⁻³
S = 1.02	Δρ_min = −0.22 e Å⁻³
489 reflections	Absolute structure: Flack (1983), 29 Friedel-pairs
86 parameters	Absolute structure parameter: 0.04 (13)
56 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.5122 (4)	−0.1223 (6)	0.5551 (5)	0.0229 (8)*
C2	0.5720 (4)	0.0659 (6)	0.5640 (6)	0.0246 (9)*
C3	0.5310 (4)	0.1598 (6)	0.6341 (7)	0.0225 (9)*
C4	0.4426 (4)	0.0747 (5)	0.6957 (7)	0.0206 (8)*
C5	0.3840 (4)	−0.1166 (6)	0.6856 (7)	0.0235 (8)*
C6	0.4205 (4)	−0.2048 (6)	0.6141 (7)	0.0213 (8)*
C71	0.4500 (16)	−0.4244 (17)	0.5139 (12)	0.0226 (18)*	0.48 (4)
C70	0.4783 (15)	−0.4270 (14)	0.5230 (13)	0.0231 (15)*	0.52 (4)
C8	0.4073 (4)	0.1726 (6)	0.7752 (7)	0.0251 (8)*
C9	0.2296 (4)	0.2224 (6)	0.7772 (8)	0.0243 (8)*
C10	0.1868 (4)	0.3886 (6)	0.7208 (7)	0.0270 (9)*
C11	0.1805 (4)	0.1155 (5)	0.9174 (7)	0.0277 (10)*
O20	0.3619 (13)	−0.3800 (12)	0.5840 (10)	0.0218 (13)*	0.52 (4)
O21	0.3903 (15)	−0.3975 (12)	0.5945 (12)	0.0216 (19)*	0.48 (4)
O10	0.5109 (17)	−0.2381 (11)	0.4870 (6)	0.0229 (13)*	0.52 (4)
O11	0.5480 (16)	−0.2548 (13)	0.4944 (8)	0.0218 (19)*	0.48 (4)
N1	0.1838 (4)	0.2773 (4)	0.8618 (7)	0.0247 (7)*
Cl1	0.32908 (9)	0.67432 (12)	0.8792 (3)	0.0358
H21	0.6365	0.1245	0.5247	0.0292*
H31	0.5645	0.2889	0.6407	0.0276*
H51	0.3237	−0.1773	0.7252	0.0282*
H711	0.5186	−0.5396	0.5123	0.0282*	0.48 (4)
H712	0.3626	−0.4371	0.4763	0.0278*	0.48 (4)
H701	0.5741	−0.4829	0.5466	0.0257*	0.52 (4)
H702	0.4304	−0.5159	0.4838	0.0262*	0.52 (4)
H81	0.4260	0.0814	0.8192	0.0295*
H82	0.4719	0.2897	0.7819	0.0303*
H91	0.1683	0.1062	0.7601	0.0289*
H102	0.0758	0.4067	0.7201	0.0390*
H101	0.2367	0.5048	0.7400	0.0388*
H103	0.2245	0.3618	0.6667	0.0386*
H112	0.1800	0.1659	0.9727	0.0414*
H113	0.2710	0.0344	0.9084	0.0408*
H111	0.0834	0.0418	0.9085	0.0411*
H11	0.252 (2)	0.369 (3)	0.8804 (16)	0.0296*
H12	0.088 (2)	0.323 (3)	0.8604 (17)	0.0296*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0301 (4)	0.0231 (5)	0.054 (5)	−0.0054 (4)	0.0006 (10)	−0.0008 (12)

Geometric parameters (Å, º) top

C1—C2	1.392 (6)	C70—H701	0.974
C1—C6	1.366 (11)	C70—H702	0.976
C1—O10	1.377 (8)	C8—C9	1.532 (5)
C2—C3	1.369 (14)	C8—H81	0.972
C2—H21	0.936	C8—H82	0.975
C3—C4	1.390 (12)	C9—C10	1.516 (12)
C3—H31	0.935	C9—N1	1.498 (15)
C4—C5	1.411 (6)	C9—H91	0.990
C4—C8	1.505 (13)	C10—H102	0.941
C5—C6	1.362 (14)	C10—H101	0.955
C5—H51	0.927	C10—H103	0.967
C6—O20	1.391 (7)	C11—N1	1.441 (11)
C71—O21	1.435 (9)	C11—H112	0.976
C71—O11	1.461 (8)	C11—H113	0.954
C71—H711	0.978	C11—H111	0.972
C71—H712	0.967	N1—H11	0.904 (17)
C70—O20	1.441 (9)	N1—H12	0.866 (17)
C70—O10	1.452 (8)

C2—C1—C6	120.8 (7)	C9—C8—H81	106.6
C2—C1—O10	128.6 (7)	C4—C8—H82	110.9
C6—C1—O10	109.9 (6)	C9—C8—H82	110.9
C1—C2—C3	115.8 (7)	H81—C8—H82	110.8
C1—C2—H21	122.2	C8—C9—C10	112.6 (7)
C3—C2—H21	122.0	C8—C9—N1	109.1 (9)
C2—C3—C4	123.8 (5)	C10—C9—N1	108.9 (5)
C2—C3—H31	118.0	C8—C9—H91	108.8
C4—C3—H31	118.2	C10—C9—H91	107.8
C3—C4—C5	119.3 (9)	N1—C9—H91	109.6
C3—C4—C8	123.9 (5)	C9—C10—H102	110.0
C5—C4—C8	116.7 (8)	C9—C10—H101	108.6
C4—C5—C6	116.0 (8)	H102—C10—H101	109.2
C4—C5—H51	121.6	C9—C10—H103	110.4
C6—C5—H51	122.5	H102—C10—H103	109.8
C1—C6—C5	124.2 (4)	H101—C10—H103	108.8
C1—C6—O20	107.6 (9)	N1—C11—H112	108.9
C5—C6—O20	127.9 (8)	N1—C11—H113	109.5
O21—C71—O11	107.5 (12)	H112—C11—H113	110.8
O21—C71—H711	109.6	N1—C11—H111	108.6
O11—C71—H711	107.7	H112—C11—H111	108.8
O21—C71—H712	110.1	H113—C11—H111	110.1
O11—C71—H712	111.0	C70—O20—C6	101.7 (10)
H711—C71—H712	110.9	C71—O21—C6	106.0 (13)
O20—C70—O10	102.5 (10)	C70—O10—C1	100.4 (10)
O20—C70—H701	111.7	C71—O11—C1	103.9 (10)
O10—C70—H701	111.1	C9—N1—C11	114.0 (5)
O20—C70—H702	108.9	C9—N1—H11	109.1 (15)
O10—C70—H702	111.3	C11—N1—H11	109.3 (15)
H701—C70—H702	111.2	C9—N1—H12	107.9 (16)
C4—C8—C9	108.1 (8)	C11—N1—H12	106.2 (14)
C4—C8—H81	109.5	H11—N1—H12	110.3 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H91···C4ⁱ	0.99	2.50	3.433 (11)	156 (1)
C10—H102···O21ⁱ	0.94	2.60	3.252 (11)	127 (1)
C10—H103···O20ⁱⁱ	0.97	2.52	3.130 (11)	121 (1)
C10—H103···O21ⁱⁱ	0.97	2.47	3.071 (11)	120 (1)
C11—H111···O10ⁱⁱⁱ	0.97	2.45	3.129 (11)	127 (1)

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

(6) top

Crystal data top

C₁₁H₁₆NO₂·Cl	F(000) = 488
M_r = 229.71	D_x = 1.629 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2087 reflections
a = 8.3242 (4) Å	θ = 4–23°
b = 6.8403 (3) Å	µ = 0.38 mm⁻¹
c = 16.447 (2) Å	T = 293 K
V = 936.48 (13) Å³	Block, colourless
Z = 4	0.20 × 0.10 × 0.05 mm

Data collection top

Bruker Kappa Apex2 diffractometer	441 reflections with I > 2.0σ(I)
Graphite monochromator	R_int = 0.036
ω scans	θ_max = 23.3°, θ_min = 3.9°
Absorption correction: multi-scan SADABS (Siemens, 1996)	h = −9→9
T_min = 0.92, T_max = 0.96	k = −7→7
4137 measured reflections	l = −5→6
486 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.026	Method = Modified Sheldrick w = 1/[σ²(F²) + ( 0.02P)² + 0.99P] , where P = (max(F_o²,0) + 2F_c²)/3
wR(F²) = 0.058	(Δ/σ)_max = 0.002
S = 1.02	Δρ_max = 0.22 e Å⁻³
478 reflections	Δρ_min = −0.21 e Å⁻³
86 parameters	Absolute structure: Flack (1983), 7 Friedel-pairs
56 restraints	Absolute structure parameter: −0.10 (14)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₁H₁₆NO₂·Cl	V = 936.48 (13) Å³
M_r = 229.71	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 8.3242 (4) Å	µ = 0.38 mm⁻¹
b = 6.8403 (3) Å	T = 293 K
c = 16.447 (2) Å	0.20 × 0.10 × 0.05 mm

Data collection top

Bruker Kappa Apex2 diffractometer	486 independent reflections
Absorption correction: multi-scan SADABS (Siemens, 1996)	441 reflections with I > 2.0σ(I)
T_min = 0.92, T_max = 0.96	R_int = 0.036
4137 measured reflections	θ_max = 23.3°

Refinement top

R[F² > 2σ(F²)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.058	Δρ_max = 0.22 e Å⁻³
S = 1.02	Δρ_min = −0.21 e Å⁻³
478 reflections	Absolute structure: Flack (1983), 7 Friedel-pairs
86 parameters	Absolute structure parameter: −0.10 (14)
56 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.5144 (5)	−0.1222 (7)	0.5535 (5)	0.0211 (8)*
C2	0.5733 (5)	0.0659 (6)	0.5622 (7)	0.0229 (9)*
C3	0.5325 (4)	0.1603 (6)	0.6338 (8)	0.0213 (9)*
C4	0.4433 (4)	0.0760 (6)	0.6955 (7)	0.0198 (8)*
C5	0.3844 (4)	−0.1180 (7)	0.6843 (8)	0.0211 (9)*
C6	0.4222 (4)	−0.2056 (6)	0.6139 (7)	0.0199 (8)*
C71	0.455 (2)	−0.430 (2)	0.5132 (14)	0.0194 (19)*	0.45 (4)
C70	0.4792 (15)	−0.4264 (17)	0.5239 (14)	0.0229 (15)*	0.55 (4)
C8	0.4084 (4)	0.1739 (6)	0.7748 (8)	0.0237 (9)*
C9	0.2284 (5)	0.2229 (6)	0.7744 (9)	0.0232 (8)*
C10	0.1869 (4)	0.3889 (6)	0.7203 (8)	0.0252 (10)*
C11	0.1800 (5)	0.1161 (6)	0.9201 (8)	0.0260 (10)*
O20	0.3634 (14)	−0.3836 (11)	0.5865 (10)	0.0203 (13)*	0.55 (4)
O21	0.3922 (18)	−0.3982 (12)	0.5933 (13)	0.016 (2)*	0.45 (4)
O10	0.5136 (18)	−0.2399 (12)	0.4860 (7)	0.0222 (13)*	0.55 (4)
O11	0.5499 (19)	−0.2569 (14)	0.4939 (9)	0.018 (2)*	0.45 (4)
N1	0.1829 (4)	0.2777 (5)	0.8631 (7)	0.0239 (8)*
Cl1	0.32488 (11)	0.67632 (13)	0.8795 (3)	0.0289
H21	0.6386	0.1265	0.5221	0.0276*
H31	0.5670	0.2916	0.6408	0.0253*
H51	0.3208	−0.1819	0.7242	0.0251*
H711	0.5200	−0.5443	0.5120	0.0238*	0.45 (4)
H712	0.3698	−0.4430	0.4754	0.0238*	0.45 (4)
H701	0.5737	−0.4813	0.5469	0.0270*	0.55 (4)
H702	0.4355	−0.5146	0.4852	0.0270*	0.55 (4)
H81	0.4333	0.0887	0.8186	0.0287*
H82	0.4700	0.2902	0.7795	0.0287*
H91	0.1693	0.1104	0.7586	0.0282*
H101	0.0746	0.4130	0.7228	0.0301*
H102	0.2435	0.5027	0.7368	0.0301*
H103	0.2161	0.3563	0.6662	0.0301*
H111	0.1509	0.1631	0.9724	0.0309*
H112	0.2830	0.0567	0.9227	0.0309*
H113	0.1032	0.0226	0.9024	0.0309*
H11	0.251 (3)	0.373 (3)	0.8812 (17)	0.0285*
H12	0.087 (2)	0.329 (3)	0.8624 (17)	0.0285*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0296 (5)	0.0218 (5)	0.035 (5)	−0.0049 (4)	0.0006 (11)	0.0005 (12)

Geometric parameters (Å, º) top

C1—C2	1.385 (6)	C70—H701	0.950
C1—C6	1.379 (12)	C70—H702	0.950
C1—O10	1.371 (9)	C8—C9	1.536 (5)
C2—C3	1.385 (15)	C8—H81	0.950
C2—H21	0.950	C8—H82	0.950
C3—C4	1.383 (13)	C9—C10	1.483 (13)
C3—H31	0.950	C9—N1	1.552 (16)
C4—C5	1.427 (7)	C9—H91	0.950
C4—C8	1.494 (14)	C10—H101	0.950
C5—C6	1.341 (16)	C10—H102	0.950
C5—H51	0.950	C10—H103	0.950
C6—O20	1.387 (7)	C11—N1	1.449 (12)
C71—O21	1.434 (9)	C11—H111	0.950
C71—O11	1.456 (8)	C11—H112	0.950
C71—H711	0.950	C11—H113	0.950
C71—H712	0.950	N1—H11	0.911 (17)
C70—O20	1.440 (9)	N1—H12	0.874 (17)
C70—O10	1.449 (8)

C2—C1—C6	120.5 (7)	C9—C8—H81	110.4
C2—C1—O10	129.1 (8)	C4—C8—H82	110.0
C6—C1—O10	109.7 (6)	C9—C8—H82	110.1
C1—C2—C3	115.7 (7)	H81—C8—H82	109.5
C1—C2—H21	122.4	C8—C9—C10	113.4 (7)
C3—C2—H21	121.8	C8—C9—N1	106.7 (9)
C2—C3—C4	124.1 (5)	C10—C9—N1	108.8 (5)
C2—C3—H31	118.0	C8—C9—H91	109.2
C4—C3—H31	117.8	C10—C9—H91	109.5
C3—C4—C5	118.5 (10)	N1—C9—H91	109.1
C3—C4—C8	123.9 (5)	C9—C10—H101	109.7
C5—C4—C8	117.6 (9)	C9—C10—H102	109.9
C4—C5—C6	116.5 (9)	H101—C10—H102	109.5
C4—C5—H51	122.0	C9—C10—H103	108.9
C6—C5—H51	121.5	H101—C10—H103	109.5
C1—C6—C5	124.6 (5)	H102—C10—H103	109.5
C1—C6—O20	109.0 (9)	N1—C11—H111	109.4
C5—C6—O20	126.2 (8)	N1—C11—H112	110.0
O21—C71—O11	106.0 (14)	H111—C11—H112	109.5
O21—C71—H711	110.7	N1—C11—H113	109.1
O11—C71—H711	111.0	H111—C11—H113	109.5
O21—C71—H712	109.9	H112—C11—H113	109.5
O11—C71—H712	109.8	C70—O20—C6	100.1 (12)
H711—C71—H712	109.5	C71—O21—C6	107.7 (15)
O20—C70—O10	105.1 (10)	C70—O10—C1	99.8 (12)
O20—C70—H701	110.5	C71—O11—C1	105.8 (11)
O10—C70—H701	110.9	C9—N1—C11	115.3 (6)
O20—C70—H702	110.6	C9—N1—H11	109.2 (15)
O10—C70—H702	110.3	C11—N1—H11	110.0 (15)
H701—C70—H702	109.5	C9—N1—H12	107.9 (16)
C4—C8—C9	106.5 (8)	C11—N1—H12	107.4 (14)
C4—C8—H81	110.2	H11—N1—H12	106.6 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H91···C4ⁱ	0.95	2.50	3.391 (12)	157 (1)
C11—H111···C2ⁱⁱ	0.95	2.47	3.167 (12)	130 (1)
C11—H113···O10ⁱⁱ	0.95	2.46	3.115 (12)	126 (1)

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

(7) top

Crystal data top

C₁₁H₁₆NO₂·Cl	F(000) = 488
M_r = 229.71	D_x = 1.634 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1011 reflections
a = 8.3325 (8) Å	θ = 5–23°
b = 6.814 (2) Å	µ = 0.39 mm⁻¹
c = 16.4416 (16) Å	T = 293 K
V = 933.50 (9) Å³	Block, colourless
Z = 4	0.20 × 0.10 × 0.05 mm

Data collection top

Bruker Kappa Apex2 diffractometer	472 reflections with I > 2.0σ(I)
Graphite monochromator	R_int = 0.042
ω scans	θ_max = 23.3°, θ_min = 4.9°
Absorption correction: multi-scan SADABS (Siemens, 1996)	h = −9→9
T_min = 0.77, T_max = 0.98	k = −2→2
2043 measured reflections	l = −18→18
510 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.043	Method = Modified Sheldrick w = 1/[σ²(F²) + ( 0.06P)² + 1.24P] , where P = (max(F_o²,0) + 2F_c²)/3
wR(F²) = 0.106	(Δ/σ)_max = 0.003
S = 1.01	Δρ_max = 0.47 e Å⁻³
507 reflections	Δρ_min = −0.50 e Å⁻³
86 parameters	Absolute structure: Flack (1983), 24 Friedel-pairs
56 restraints	Absolute structure parameter: 0.21 (19)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₁H₁₆NO₂·Cl	V = 933.50 (9) Å³
M_r = 229.71	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 8.3325 (8) Å	µ = 0.39 mm⁻¹
b = 6.814 (2) Å	T = 293 K
c = 16.4416 (16) Å	0.20 × 0.10 × 0.05 mm

Data collection top

Bruker Kappa Apex2 diffractometer	510 independent reflections
Absorption correction: multi-scan SADABS (Siemens, 1996)	472 reflections with I > 2.0σ(I)
T_min = 0.77, T_max = 0.98	R_int = 0.042
2043 measured reflections	θ_max = 23.3°

Refinement top

R[F² > 2σ(F²)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.106	Δρ_max = 0.47 e Å⁻³
S = 1.01	Δρ_min = −0.50 e Å⁻³
507 reflections	Absolute structure: Flack (1983), 24 Friedel-pairs
86 parameters	Absolute structure parameter: 0.21 (19)
56 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.5153 (8)	−0.120 (2)	0.5549 (4)	0.0242 (10)*
C2	0.5719 (7)	0.061 (3)	0.5638 (4)	0.0253 (11)*
C3	0.5338 (6)	0.164 (3)	0.6361 (4)	0.0258 (11)*
C4	0.4451 (7)	0.070 (3)	0.6969 (4)	0.0239 (10)*
C5	0.3871 (7)	−0.113 (3)	0.6847 (4)	0.0248 (11)*
C6	0.4224 (7)	−0.2067 (16)	0.6139 (5)	0.0254 (10)*
C71	0.446 (4)	−0.417 (6)	0.5154 (10)	0.024 (2)*	0.34 (6)
C70	0.480 (2)	−0.430 (3)	0.5204 (9)	0.0239 (15)*	0.66 (6)
C8	0.4074 (7)	0.176 (2)	0.7748 (4)	0.0257 (11)*
C9	0.2312 (7)	0.219 (2)	0.7799 (4)	0.0277 (11)*
C10	0.1878 (6)	0.394 (3)	0.7211 (4)	0.0308 (13)*
C11	0.1804 (7)	0.110 (3)	0.9200 (4)	0.0270 (13)*
O20	0.3687 (14)	−0.385 (2)	0.5851 (7)	0.0250 (13)*	0.66 (6)
O21	0.392 (3)	−0.402 (2)	0.5977 (12)	0.024 (3)*	0.34 (6)
O10	0.519 (2)	−0.242 (2)	0.4875 (5)	0.0238 (14)*	0.66 (6)
O11	0.554 (4)	−0.260 (3)	0.4967 (12)	0.023 (3)*	0.34 (6)
N1	0.1819 (6)	0.275 (2)	0.8620 (3)	0.0274 (11)*
Cl1	0.32505 (17)	0.6773 (6)	0.8794 (2)	0.0327
H21	0.6362	0.1193	0.5243	0.0314*
H31	0.5681	0.2932	0.6433	0.0310*
H51	0.3247	−0.1729	0.7236	0.0301*
H711	0.5033	−0.5400	0.5102	0.0301*	0.34 (6)
H712	0.3548	−0.4166	0.4787	0.0300*	0.34 (6)
H701	0.5741	−0.4960	0.5416	0.0290*	0.66 (6)
H702	0.4269	−0.5130	0.4800	0.0291*	0.66 (6)
H81	0.4297	0.0898	0.8203	0.0295*
H82	0.4706	0.2956	0.7791	0.0303*
H91	0.1721	0.1016	0.7632	0.0328*
H102	0.0743	0.4166	0.7219	0.0457*
H101	0.2428	0.5103	0.7375	0.0456*
H103	0.2180	0.3623	0.6664	0.0457*
H112	0.1689	0.1611	0.9747	0.0410*
H113	0.2804	0.0374	0.9178	0.0411*
H111	0.0915	0.0234	0.9083	0.0408*
H11	0.243 (4)	0.371 (4)	0.8807 (14)	0.0325*
H12	0.085 (3)	0.328 (5)	0.8593 (14)	0.0325*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0337 (8)	0.031 (7)	0.0335 (7)	−0.0058 (14)	0.0004 (6)	0.0020 (19)

Geometric parameters (Å, º) top

C1—C2	1.33 (2)	C70—H701	0.971
C1—C6	1.372 (12)	C70—H702	0.975
C1—O10	1.384 (9)	C8—C9	1.499 (9)
C2—C3	1.415 (16)	C8—H81	0.969
C2—H21	0.930	C8—H82	0.973
C3—C4	1.397 (15)	C9—C10	1.58 (2)
C3—H31	0.934	C9—N1	1.463 (9)
C4—C5	1.35 (3)	C9—H91	0.977
C4—C8	1.504 (14)	C10—H102	0.958
C5—C6	1.361 (13)	C10—H101	0.955
C5—H51	0.922	C10—H103	0.958
C6—O20	1.380 (9)	C11—N1	1.473 (19)
C71—O21	1.431 (9)	C11—H112	0.967
C71—O11	1.435 (9)	C11—H113	0.971
C71—H711	0.966	C11—H111	0.968
C71—H712	0.968	N1—H11	0.886 (19)
C70—O20	1.442 (8)	N1—H12	0.883 (19)
C70—O10	1.431 (9)

C2—C1—C6	121.3 (7)	C9—C8—H81	105.3
C2—C1—O10	129.4 (9)	C4—C8—H82	110.5
C6—C1—O10	108.9 (10)	C9—C8—H82	111.3
C1—C2—C3	118.1 (10)	H81—C8—H82	110.3
C1—C2—H21	121.5	C8—C9—C10	109.8 (8)
C3—C2—H21	120.5	C8—C9—N1	112.2 (6)
C2—C3—C4	119.6 (16)	C10—C9—N1	107.6 (11)
C2—C3—H31	120.2	C8—C9—H91	108.6
C4—C3—H31	120.2	C10—C9—H91	109.3
C3—C4—C5	120.3 (11)	N1—C9—H91	109.3
C3—C4—C8	120.1 (15)	C9—C10—H102	109.9
C5—C4—C8	119.6 (9)	C9—C10—H101	110.2
C4—C5—C6	119.0 (9)	H102—C10—H101	109.5
C4—C5—H51	120.7	C9—C10—H103	110.2
C6—C5—H51	120.4	H102—C10—H103	108.0
C1—C6—C5	121.6 (10)	H101—C10—H103	109.0
C1—C6—O20	108.5 (8)	N1—C11—H112	109.3
C5—C6—O20	129.7 (9)	N1—C11—H113	111.0
O21—C71—O11	110.1 (16)	H112—C11—H113	107.7
O21—C71—H711	107.7	N1—C11—H111	110.0
O11—C71—H711	108.4	H112—C11—H111	109.2
O21—C71—H712	110.0	H113—C11—H111	109.6
O11—C71—H712	110.7	C70—O20—C6	103.5 (11)
H711—C71—H712	109.8	C71—O21—C6	101 (2)
O20—C70—O10	103.6 (11)	C70—O10—C1	103.2 (12)
O20—C70—H701	110.7	C71—O11—C1	103 (2)
O10—C70—H701	111.1	C11—N1—C9	113.6 (11)
O20—C70—H702	109.7	C11—N1—H11	110.0 (16)
O10—C70—H702	111.4	C9—N1—H11	110.5 (16)
H701—C70—H702	110.1	C11—N1—H12	109.8 (16)
C4—C8—C9	110.2 (6)	C9—N1—H12	108.5 (16)
C4—C8—H81	109.1	H11—N1—H12	104.0 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C71—H702···N1ⁱ	0.89	2.58	3.447 (17)	165 (3)
C70—H702···N1ⁱ	0.98	2.58	3.552 (17)	173 (1)
C9—H91···C4ⁱⁱ	0.98	2.48	3.379 (17)	153 (1)
C10—H102···O21ⁱⁱ	0.96	2.55	3.195 (17)	125 (1)
C11—H112···C2ⁱⁱⁱ	0.97	2.58	3.180 (17)	121 (1)
C11—H111···O10ⁱⁱⁱ	0.97	2.41	3.126 (17)	130 (1)

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

Experimental details

	(1)	(2)	(3)	(4)
Crystal data
Chemical formula	C₁₁H₁₆NO₂·Cl	C₁₁H₁₆NO₂·Cl	C₁₁H₁₆NO₂·Cl	C₁₁H₁₆NO₂·Cl
M_r	229.71	229.71	229.71	229.71
Crystal system, space group	Orthorhombic, Pca2₁	Orthorhombic, Pca2₁	Orthorhombic, Pca2₁	Orthorhombic, Pca2₁
Temperature (K)	293	293	293	293
a, b, c (Å)	9.4272 (2), 7.0774 (2), 18.2519 (4)	9.1478 (3), 6.9826 (3), 17.6799 (4)	8.8661 (5), 6.9379 (4), 17.120 (3)	8.4895 (2), 6.8759 (2), 16.6225 (14)
V (Å³)	1217.77 (3)	1129.31 (3)	1053.08 (17)	970.30 (8)
Z	4	4	4	4
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.30	0.32	0.34	0.37
Crystal size (mm)	0.35 × 0.22 × 0.10	0.20 × 0.10 × 0.05	0.20 × 0.10 × 0.05	0.2 × 0.1 × 0.05

Data collection
Diffractometer	Bruker Kappa Apex2 diffractometer	Bruker Kappa Apex2 diffractometer	Bruker Kappa Apex2 diffractometer	Bruker Kappa Apex2 diffractometer
Absorption correction	Multi-scan SADABS (Siemens, 1996)	Multi-scan SADABS (Siemens, 1996)	Multi-scan SADABS (Siemens, 1996)	Multi-scan SADABS (Siemens, 1996)
T_min, T_max	0.83, 0.97	0.87, 0.98	0.87, 0.98	0.89, 0.96
No. of measured, independent and observed [I > 2.0σ(I)] reflections	26105, 2636, 2603	5069, 1027, 977	4833, 572, 530	4431, 522, 498
R_int	0.033	0.033	0.038	0.032
θ_max (°)	27.1	23.3	23.3	23.2
(sin θ/λ)_max (Å⁻¹)	0.641	0.557	0.556	0.555

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.080, 1.01	0.035, 0.081, 1.04	0.031, 0.071, 1.02	0.027, 0.062, 0.97
No. of reflections	2628	1023	567	518
No. of parameters	171	86	86	86
No. of restraints	158	56	56	56
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.10	0.61, −0.57	0.23, −0.22	0.14, −0.12
Absolute structure	Flack (1983), 1254 Friedel-pairs	Flack (1983), 355 Friedel-pairs	Flack (1983), 455 Friedel-pairs	Flack (1983), 50 Friedel-pairs
Absolute structure parameter	0.04 (5)	0.07 (11)	0.19 (16)	−0.02 (15)

	(5)	(6)	(7)
Crystal data
Chemical formula	C₁₁H₁₆NO₂·Cl	C₁₁H₁₆NO₂·Cl	C₁₁H₁₆NO₂·Cl
M_r	229.71	229.71	229.71
Crystal system, space group	Orthorhombic, Pca2₁	Orthorhombic, Pca2₁	Orthorhombic, Pca2₁
Temperature (K)	293	293	293
a, b, c (Å)	8.4043 (2), 6.8578 (2), 16.5271 (12)	8.3242 (4), 6.8403 (3), 16.447 (2)	8.3325 (8), 6.814 (2), 16.4416 (16)
V (Å³)	952.54 (7)	936.48 (13)	933.50 (9)
Z	4	4	4
Radiation type	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.38	0.38	0.39
Crystal size (mm)	0.2 × 0.1 × 0.05	0.20 × 0.10 × 0.05	0.20 × 0.10 × 0.05

Data collection
Diffractometer	Bruker Kappa Apex2 diffractometer	Bruker Kappa Apex2 diffractometer	Bruker Kappa Apex2 diffractometer
Absorption correction	Multi-scan SADABS (Siemens, 1996)	Multi-scan SADABS (Siemens, 1996)	Multi-scan SADABS (Siemens, 1996)
T_min, T_max	0.91, 0.96	0.92, 0.96	0.77, 0.98
No. of measured, independent and observed [I > 2.0σ(I)] reflections	4206, 493, 459	4137, 486, 441	2043, 510, 472
R_int	0.033	0.036	0.042
θ_max (°)	23.2	23.3	23.3
(sin θ/λ)_max (Å⁻¹)	0.555	0.557	0.556

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.055, 1.02	0.026, 0.058, 1.02	0.043, 0.106, 1.01
No. of reflections	489	478	507
No. of parameters	86	86	86
No. of restraints	56	56	56
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.22	0.22, −0.21	0.47, −0.50
Absolute structure	Flack (1983), 29 Friedel-pairs	Flack (1983), 7 Friedel-pairs	Flack (1983), 24 Friedel-pairs
Absolute structure parameter	0.04 (13)	−0.10 (14)	0.21 (19)

Computer programs: Apex2 (Bruker AXS, 2006), SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), CAMERON (Watkin et al., 1996).

Selected geometric parameters (Å, º) for (1) top

C1—C2	1.368 (2)	C70—O20	1.440 (5)
C1—C6	1.372 (2)	C70—O10	1.441 (4)
C1—O10	1.388 (3)	C71—O21	1.439 (9)
C2—C3	1.395 (3)	C71—O11	1.428 (9)
C3—C4	1.386 (2)	C8—C9	1.5329 (19)
C4—C5	1.393 (2)	C9—C10	1.517 (2)
C4—C8	1.509 (2)	C9—N1	1.4915 (19)
C5—C6	1.368 (2)	C11—N1	1.483 (2)
C6—O20	1.387 (3)

C2—C1—C6	121.92 (14)	O20—C70—O10	108.5 (4)
C2—C1—O10	127.7 (2)	O21—C71—O11	98.4 (16)
C6—C1—O10	110.3 (2)	C4—C8—C9	111.09 (12)
C1—C2—C3	116.30 (14)	C8—C9—C10	113.43 (13)
C2—C3—C4	122.22 (14)	C8—C9—N1	109.89 (12)
C3—C4—C5	120.01 (14)	C10—C9—N1	108.22 (11)
C3—C4—C8	121.76 (13)	C70—O20—C6	104.4 (4)
C5—C4—C8	118.23 (14)	C71—O21—C6	103.8 (12)
C4—C5—C6	117.19 (14)	C70—O10—C1	104.4 (4)
C1—C6—C5	122.35 (14)	C71—O11—C1	102.8 (13)
C1—C6—O20	110.5 (2)	C9—N1—C11	115.78 (11)
C5—C6—O20	127.1 (2)

Hydrogen-bond geometry (Å, º) for (1) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H112···O10ⁱ	0.943	2.562	3.303 (5)	135.64 (19)
C11—H112···O11ⁱ	0.943	2.503	3.149 (5)	125.8 (6)

Symmetry code: (i) −x+1, −y, z+1/2.

Selected geometric parameters (Å, º) for (2) top

C1—C2	1.365 (6)	C71—O21	1.470 (8)
C1—C6	1.366 (6)	C71—O11	1.462 (8)
C1—O10	1.394 (6)	C70—O20	1.459 (8)
C2—C3	1.392 (5)	C70—O10	1.436 (8)
C3—C4	1.381 (6)	C8—C9	1.525 (5)
C4—C5	1.381 (6)	C9—C10	1.509 (6)
C4—C8	1.515 (5)	C9—N1	1.487 (5)
C5—C6	1.367 (6)	C11—N1	1.456 (5)
C6—O20	1.394 (7)

C2—C1—C6	121.8 (4)	O21—C71—O11	105.4 (7)
C2—C1—O10	128.7 (4)	O20—C70—O10	102.7 (7)
C6—C1—O10	108.6 (5)	C4—C8—C9	111.6 (3)
C1—C2—C3	116.8 (4)	C8—C9—C10	112.3 (3)
C2—C3—C4	121.6 (4)	C8—C9—N1	110.6 (3)
C3—C4—C5	120.1 (4)	C10—C9—N1	108.8 (3)
C3—C4—C8	121.6 (4)	C70—O20—C6	101.8 (7)
C5—C4—C8	118.3 (4)	C71—O21—C6	102.7 (7)
C4—C5—C6	118.0 (4)	C70—O10—C1	102.6 (7)
C5—C6—C1	121.7 (4)	C71—O11—C1	101.5 (7)
C5—C6—O20	128.7 (5)	C9—N1—C11	116.5 (4)
C1—C6—O20	108.8 (4)

Hydrogen-bond geometry (Å, º) for (2) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H112···O10ⁱ	0.953	2.503	3.275 (8)	138.1 (3)
C11—H112···O11ⁱ	0.953	2.348	3.040 (8)	129.0 (3)

Symmetry code: (i) −x+1, −y, z+1/2.

Selected geometric parameters (Å, º) for (3) top

C1—C2	1.394 (7)	C70—O20	1.445 (9)
C1—C6	1.341 (13)	C70—O10	1.451 (9)
C1—O10	1.366 (9)	C71—O21	1.440 (10)
C2—C3	1.373 (19)	C71—O11	1.459 (8)
C3—C4	1.382 (14)	C8—C9	1.549 (7)
C4—C5	1.405 (7)	C9—C10	1.509 (15)
C4—C8	1.490 (18)	C9—N1	1.532 (19)
C5—C6	1.386 (17)	C11—N1	1.477 (13)
C6—O20	1.404 (8)

C2—C1—C6	121.1 (9)	O20—C70—O10	103.0 (11)
C2—C1—O10	129.6 (10)	O21—C71—O11	104.3 (13)
C6—C1—O10	108.3 (6)	C4—C8—C9	108.6 (9)
C1—C2—C3	115.8 (9)	C8—C9—C10	113.0 (8)
C2—C3—C4	123.8 (6)	C8—C9—N1	108.5 (10)
C3—C4—C5	119.4 (10)	C10—C9—N1	108.9 (7)
C3—C4—C8	122.8 (6)	C70—O20—C6	97.0 (12)
C5—C4—C8	117.7 (9)	C71—O21—C6	104.9 (13)
C4—C5—C6	115.7 (9)	C70—O10—C1	99.7 (12)
C5—C6—C1	124.1 (5)	C71—O11—C1	104.5 (10)
C5—C6—O20	124.7 (9)	C9—N1—C11	115.9 (6)
C1—C6—O20	110.8 (10)

Hydrogen-bond geometry (Å, º) for (3) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H112···O10ⁱ	0.891	2.432	3.150 (13)	137.9 (3)
C11—H112···O11ⁱ	0.891	2.287	2.928 (13)	128.7 (4)
C11—H113···O10ⁱⁱ	0.911	2.587	3.159 (13)	121.4 (3)

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

Selected geometric parameters (Å, º) for (4) top

C1—C2	1.392 (6)	C70—O20	1.437 (9)
C1—C6	1.353 (11)	C70—O10	1.453 (8)
C1—O10	1.370 (9)	C71—O21	1.432 (9)
C2—C3	1.364 (16)	C71—O11	1.469 (8)
C3—C4	1.394 (13)	C8—C9	1.535 (6)
C4—C5	1.401 (7)	C9—C10	1.534 (14)
C4—C8	1.484 (15)	C9—N1	1.512 (18)
C5—C6	1.375 (16)	C11—N1	1.431 (12)
C6—O20	1.394 (8)

C2—C1—C6	120.9 (8)	O20—C70—O10	103.1 (11)
C2—C1—O10	128.7 (8)	O21—C71—O11	105.2 (13)
C6—C1—O10	109.5 (6)	C4—C8—C9	109.6 (8)
C1—C2—C3	116.1 (8)	C8—C9—C10	111.8 (8)
C2—C3—C4	123.5 (5)	C8—C9—N1	110.1 (10)
C3—C4—C5	119.5 (9)	C10—C9—N1	110.2 (6)
C3—C4—C8	123.3 (5)	C70—O20—C6	100.4 (11)
C5—C4—C8	117.3 (9)	C71—O21—C6	107.2 (13)
C4—C5—C6	115.9 (8)	C70—O10—C1	100.3 (12)
C5—C6—C1	124.0 (4)	C71—O11—C1	105.1 (10)
C5—C6—O20	126.8 (8)	C9—N1—C11	113.8 (6)
C1—C6—O20	108.9 (9)

Hydrogen-bond geometry (Å, º) for (4) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H91···C4ⁱ	0.975	2.573	3.467 (12)	152.43 (17)
C11—H111···O10ⁱⁱ	0.960	2.415	3.141 (12)	132.2 (4)

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

Selected geometric parameters (Å, º) for (5) top

C1—C2	1.392 (6)	C71—O21	1.435 (9)
C1—C6	1.366 (11)	C71—O11	1.461 (8)
C1—O10	1.377 (8)	C70—O20	1.441 (9)
C2—C3	1.369 (14)	C70—O10	1.452 (8)
C3—C4	1.390 (12)	C8—C9	1.532 (5)
C4—C5	1.411 (6)	C9—C10	1.516 (12)
C4—C8	1.505 (13)	C9—N1	1.498 (15)
C5—C6	1.362 (14)	C11—N1	1.441 (11)
C6—O20	1.391 (7)

C2—C1—C6	120.8 (7)	O21—C71—O11	107.5 (12)
C2—C1—O10	128.6 (7)	O20—C70—O10	102.5 (10)
C6—C1—O10	109.9 (6)	C4—C8—C9	108.1 (8)
C1—C2—C3	115.8 (7)	C8—C9—C10	112.6 (7)
C2—C3—C4	123.8 (5)	C8—C9—N1	109.1 (9)
C3—C4—C5	119.3 (9)	C10—C9—N1	108.9 (5)
C3—C4—C8	123.9 (5)	C70—O20—C6	101.7 (10)
C5—C4—C8	116.7 (8)	C71—O21—C6	106.0 (13)
C4—C5—C6	116.0 (8)	C70—O10—C1	100.4 (10)
C1—C6—C5	124.2 (4)	C71—O11—C1	103.9 (10)
C1—C6—O20	107.6 (9)	C9—N1—C11	114.0 (5)
C5—C6—O20	127.9 (8)

Hydrogen-bond geometry (Å, º) for (5) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H91···C4ⁱ	0.990	2.504	3.433 (11)	156.14 (16)
C10—H102···O21ⁱ	0.941	2.597	3.252 (11)	127.0 (4)
C10—H103···O20ⁱⁱ	0.967	2.516	3.130 (11)	121.3 (3)
C10—H103···O21ⁱⁱ	0.967	2.467	3.071 (11)	120.4 (4)
C11—H111···O10ⁱⁱⁱ	0.972	2.448	3.129 (11)	126.8 (3)

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

Selected geometric parameters (Å, º) for (6) top

C1—C2	1.385 (6)	C71—O21	1.434 (9)
C1—C6	1.379 (12)	C71—O11	1.456 (8)
C1—O10	1.371 (9)	C70—O20	1.440 (9)
C2—C3	1.385 (15)	C70—O10	1.449 (8)
C3—C4	1.383 (13)	C8—C9	1.536 (5)
C4—C5	1.427 (7)	C9—C10	1.483 (13)
C4—C8	1.494 (14)	C9—N1	1.552 (16)
C5—C6	1.341 (16)	C11—N1	1.449 (12)
C6—O20	1.387 (7)

C2—C1—C6	120.5 (7)	O21—C71—O11	106.0 (14)
C2—C1—O10	129.1 (8)	O20—C70—O10	105.1 (10)
C6—C1—O10	109.7 (6)	C4—C8—C9	106.5 (8)
C1—C2—C3	115.7 (7)	C8—C9—C10	113.4 (7)
C2—C3—C4	124.1 (5)	C8—C9—N1	106.7 (9)
C3—C4—C5	118.5 (10)	C10—C9—N1	108.8 (5)
C3—C4—C8	123.9 (5)	C70—O20—C6	100.1 (12)
C5—C4—C8	117.6 (9)	C71—O21—C6	107.7 (15)
C4—C5—C6	116.5 (9)	C70—O10—C1	99.8 (12)
C1—C6—C5	124.6 (5)	C71—O11—C1	105.8 (11)
C1—C6—O20	109.0 (9)	C9—N1—C11	115.3 (6)
C5—C6—O20	126.2 (8)

Hydrogen-bond geometry (Å, º) for (6) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H91···C4ⁱ	0.950	2.498	3.391 (12)	156.59 (18)
C11—H111···C2ⁱⁱ	0.950	2.472	3.167 (12)	130.0 (3)
C11—H113···O10ⁱⁱ	0.950	2.462	3.115 (12)	125.9 (3)

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

Selected geometric parameters (Å, º) for (7) top

C1—C2	1.33 (2)	C71—O21	1.431 (9)
C1—C6	1.372 (12)	C71—O11	1.435 (9)
C1—O10	1.384 (9)	C70—O20	1.442 (8)
C2—C3	1.415 (16)	C70—O10	1.431 (9)
C3—C4	1.397 (15)	C8—C9	1.499 (9)
C4—C5	1.35 (3)	C9—C10	1.58 (2)
C4—C8	1.504 (14)	C9—N1	1.463 (9)
C5—C6	1.361 (13)	C11—N1	1.473 (19)
C6—O20	1.380 (9)

C2—C1—C6	121.3 (7)	O21—C71—O11	110.1 (16)
C2—C1—O10	129.4 (9)	O20—C70—O10	103.6 (11)
C6—C1—O10	108.9 (10)	C4—C8—C9	110.2 (6)
C1—C2—C3	118.1 (10)	C8—C9—C10	109.8 (8)
C2—C3—C4	119.6 (16)	C8—C9—N1	112.2 (6)
C3—C4—C5	120.3 (11)	C10—C9—N1	107.6 (11)
C3—C4—C8	120.1 (15)	C70—O20—C6	103.5 (11)
C5—C4—C8	119.6 (9)	C71—O21—C6	101 (2)
C4—C5—C6	119.0 (9)	C70—O10—C1	103.2 (12)
C1—C6—C5	121.6 (10)	C71—O11—C1	103 (2)
C1—C6—O20	108.5 (8)	C11—N1—C9	113.6 (11)
C5—C6—O20	129.7 (9)

Hydrogen-bond geometry (Å, º) for (7) top

D—H···A	D—H	H···A	D···A	D—H···A
C71—H702···N1ⁱ	0.887	2.583	3.447 (17)	165 (3)
C70—H702···N1ⁱ	0.975	2.583	3.552 (17)	172.9 (3)
C9—H91···C4ⁱⁱ	0.977	2.477	3.379 (17)	153.4 (6)
C10—H102···O21ⁱⁱ	0.958	2.549	3.195 (17)	124.8 (4)
C11—H112···C2ⁱⁱⁱ	0.967	2.575	3.180 (17)	120.7 (4)
C11—H111···O10ⁱⁱⁱ	0.968	2.413	3.126 (17)	130.1 (3)

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

Format		BIBTeX
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Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text