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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.
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
Crystal data, data collection and structure refinement details are summarized
in Table 1.
S2. Results and discussion
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).
Crystal data top
C11H16NO2·Cl | F(000) = 488 |
Mr = 229.71 | Dx = 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 | Rint = 0.033 |
ϕ & ω scans | θmax = 27.1°, θmin = 2.2° |
Absorption correction: multi-scan SADABS (Siemens, 1996) | h = −12→12 |
Tmin = 0.83, Tmax = 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(Fo2,0) + 2Fc2)/3 |
wR(F2) = 0.080 | (Δ/σ)max = 0.009 |
S = 1.01 | Δρmax = 0.18 e Å−3 |
2628 reflections | Δρmin = −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 |
Mr = 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) |
Tmin = 0.83, Tmax = 0.97 | Rint = 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 | Δρmax = 0.18 e Å−3 |
S = 1.01 | Δρmin = −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 | Uiso*/Ueq | 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. |
Crystal data top
C11H16NO2·Cl | F(000) = 488 |
Mr = 229.71 | Dx = 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 | Rint = 0.033 |
ω scans | θmax = 23.3°, θmin = 3.7° |
Absorption correction: multi-scan SADABS (Siemens, 1996) | h = −9→9 |
Tmin = 0.87, Tmax = 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(Fo2,0) + 2Fc2)/3 |
wR(F2) = 0.081 | (Δ/σ)max = 0.002 |
S = 1.04 | Δρmax = 0.61 e Å−3 |
1023 reflections | Δρmin = −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 |
Mr = 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) |
Tmin = 0.87, Tmax = 0.98 | Rint = 0.033 |
5069 measured reflections | θmax = 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 | Δρmax = 0.61 e Å−3 |
S = 1.04 | Δρmin = −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 | Uiso*/Ueq | 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. |
Crystal data top
C11H16NO2·Cl | F(000) = 488.000 |
Mr = 229.71 | Dx = 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 | Rint = 0.038 |
ω scans | θmax = 23.3°, θmin = 2.9° |
Absorption correction: multi-scan SADABS (Siemens, 1996) | h = −9→9 |
Tmin = 0.87, Tmax = 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(Fo2,0) + 2Fc2)/3 |
wR(F2) = 0.071 | (Δ/σ)max = 0.001 |
S = 1.02 | Δρmax = 0.23 e Å−3 |
567 reflections | Δρmin = −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 |
Mr = 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) |
Tmin = 0.87, Tmax = 0.98 | Rint = 0.038 |
4833 measured reflections | θmax = 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 | Δρmax = 0.23 e Å−3 |
S = 1.02 | Δρmin = −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 | Uiso*/Ueq | 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. |
Crystal data top
C11H16NO2·Cl | F(000) = 488 |
Mr = 229.71 | Dx = 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 | Rint = 0.032 |
ω scans | θmax = 23.2°, θmin = 3.0° |
Absorption correction: multi-scan SADABS (Siemens, 1996) | h = −9→9 |
Tmin = 0.89, Tmax = 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(Fo2,0) + 2Fc2)/3 |
wR(F2) = 0.062 | (Δ/σ)max = 0.003 |
S = 0.97 | Δρmax = 0.14 e Å−3 |
518 reflections | Δρmin = −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 |
Mr = 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) |
Tmin = 0.89, Tmax = 0.96 | Rint = 0.032 |
4431 measured reflections | θmax = 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 | Δρmax = 0.14 e Å−3 |
S = 0.97 | Δρmin = −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 | Uiso*/Ueq | 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. |
Crystal data top
C11H16NO2·Cl | F(000) = 488 |
Mr = 229.71 | Dx = 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 | Rint = 0.033 |
ω scans | θmax = 23.2°, θmin = 3.8° |
Absorption correction: multi-scan SADABS (Siemens, 1996) | h = −9→9 |
Tmin = 0.91, Tmax = 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(Fo2,0) + 2Fc2)/3 |
wR(F2) = 0.055 | (Δ/σ)max = 0.0003 |
S = 1.02 | Δρmax = 0.20 e Å−3 |
489 reflections | Δρmin = −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 |
Mr = 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) |
Tmin = 0.91, Tmax = 0.96 | Rint = 0.033 |
4206 measured reflections | θmax = 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 | Δρmax = 0.20 e Å−3 |
S = 1.02 | Δρmin = −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 | Uiso*/Ueq | 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. |
Crystal data top
C11H16NO2·Cl | F(000) = 488 |
Mr = 229.71 | Dx = 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 | Rint = 0.036 |
ω scans | θmax = 23.3°, θmin = 3.9° |
Absorption correction: multi-scan SADABS (Siemens, 1996) | h = −9→9 |
Tmin = 0.92, Tmax = 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(Fo2,0) + 2Fc2)/3 |
wR(F2) = 0.058 | (Δ/σ)max = 0.002 |
S = 1.02 | Δρmax = 0.22 e Å−3 |
478 reflections | Δρmin = −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 |
Mr = 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) |
Tmin = 0.92, Tmax = 0.96 | Rint = 0.036 |
4137 measured reflections | θmax = 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 | Δρmax = 0.22 e Å−3 |
S = 1.02 | Δρmin = −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 | Uiso*/Ueq | 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. |
Crystal data top
C11H16NO2·Cl | F(000) = 488 |
Mr = 229.71 | Dx = 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 | Rint = 0.042 |
ω scans | θmax = 23.3°, θmin = 4.9° |
Absorption correction: multi-scan SADABS (Siemens, 1996) | h = −9→9 |
Tmin = 0.77, Tmax = 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(Fo2,0) + 2Fc2)/3 |
wR(F2) = 0.106 | (Δ/σ)max = 0.003 |
S = 1.01 | Δρmax = 0.47 e Å−3 |
507 reflections | Δρmin = −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 |
Mr = 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) |
Tmin = 0.77, Tmax = 0.98 | Rint = 0.042 |
2043 measured reflections | θmax = 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 | Δρmax = 0.47 e Å−3 |
S = 1.01 | Δρmin = −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 | Uiso*/Ueq | 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 |
Mr | 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) |
Tmin, Tmax | 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 |
Rint | 0.033 | 0.033 | 0.038 | 0.032 |
θmax (°) | 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 |
Δρmax, Δρmin (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 |
Mr | 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) |
Tmin, Tmax | 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 |
Rint | 0.033 | 0.036 | 0.042 |
θmax (°) | 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 |
Δρmax, Δρmin (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) |
Selected geometric parameters (Å, º) for (1) topC1—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) topC1—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) topC1—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) topC1—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) topC1—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) topC1—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) topC1—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. |
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