

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520613022129/gp5066sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2052520613022129/gp50661sup2.hkl |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2052520613022129/gp50662sup3.hkl |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2052520613022129/gp50663sup4.hkl |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2052520613022129/gp50664sup5.hkl |
CCDC references: 985000; 985001; 985002; 985003
For all compounds, data collection: Bruker SMART, Bruker (1998); cell refinement: Bruker SAINT+, Bruker (1999); data reduction: Bruker SAINT+; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009).
C7H5Cl1.46F0.54NO | F(000) = 733.2 |
Mr = 181.07 | Dx = 1.605 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 5727 reflections |
a = 8.5220 (2) Å | θ = 2.9–28.4° |
b = 12.2910 (3) Å | µ = 0.61 mm−1 |
c = 14.3090 (4) Å | T = 173 K |
V = 1498.78 (7) Å3 | Block, colourless |
Z = 8 | 0.45 × 0.19 × 0.18 mm |
Bruker SMART 1K CCD area detector diffractometer | 1706 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
ω scans | θmax = 28°, θmin = 2.9° |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | h = −10→11 |
Tmin = 0.765, Tmax = 0.895 | k = −16→15 |
17793 measured reflections | l = −18→18 |
1811 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.090 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.25 | w = 1/[σ2(Fo2) + (0.0212P)2 + 1.2505P] where P = (Fo2 + 2Fc2)/3 |
1811 reflections | (Δ/σ)max < 0.001 |
122 parameters | Δρmax = 0.22 e Å−3 |
26 restraints | Δρmin = −0.22 e Å−3 |
C7H5Cl1.46F0.54NO | V = 1498.78 (7) Å3 |
Mr = 181.07 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 8.5220 (2) Å | µ = 0.61 mm−1 |
b = 12.2910 (3) Å | T = 173 K |
c = 14.3090 (4) Å | 0.45 × 0.19 × 0.18 mm |
Bruker SMART 1K CCD area detector diffractometer | 1811 independent reflections |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | 1706 reflections with I > 2σ(I) |
Tmin = 0.765, Tmax = 0.895 | Rint = 0.052 |
17793 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 26 restraints |
wR(F2) = 0.090 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.25 | Δρmax = 0.22 e Å−3 |
1811 reflections | Δρmin = −0.22 e Å−3 |
122 parameters |
Experimental. Absorption corrections were made using the program SADABS (Sheldrick, 1996). |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.55412 (18) | 0.41372 (14) | 0.65058 (12) | 0.0238 (4) | |
C2 | 0.56802 (18) | 0.36432 (14) | 0.56340 (13) | 0.0264 (4) | |
C3 | 0.6658 (2) | 0.40402 (18) | 0.49453 (14) | 0.0350 (5) | |
H3 | 0.6718 | 0.369 | 0.4354 | 0.042* | |
C4 | 0.7549 (3) | 0.4955 (2) | 0.51292 (15) | 0.0392 (5) | |
H4 | 0.823 | 0.5235 | 0.4662 | 0.047* | |
C5 | 0.7456 (2) | 0.54661 (18) | 0.59882 (15) | 0.0368 (5) | |
H5 | 0.8084 | 0.6087 | 0.6116 | 0.044* | |
C6 | 0.6446 (2) | 0.50675 (16) | 0.66595 (13) | 0.0294 (4) | |
C7 | 0.4956 (2) | 0.33346 (17) | 0.80107 (13) | 0.0295 (4) | |
H7 | 0.4162 | 0.3066 | 0.8416 | 0.035* | |
O1 | 0.63083 (16) | 0.32872 (14) | 0.82907 (10) | 0.0367 (4) | |
Cl1 | 0.45573 (16) | 0.25127 (11) | 0.53968 (7) | 0.0273 (2) | 0.728 (4) |
Cl2 | 0.62585 (16) | 0.57954 (10) | 0.76865 (9) | 0.0347 (3) | 0.728 (4) |
F1 | 0.4829 (10) | 0.2728 (5) | 0.5474 (6) | 0.062 (4) | 0.272 (4) |
F2 | 0.6341 (11) | 0.5535 (7) | 0.7512 (4) | 0.065 (4) | 0.272 (4) |
N1 | 0.44897 (18) | 0.37314 (14) | 0.71833 (11) | 0.0263 (3) | |
H1 | 0.351 (3) | 0.3664 (19) | 0.7027 (16) | 0.032* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0172 (7) | 0.0292 (9) | 0.0249 (8) | 0.0031 (7) | −0.0025 (6) | 0.0017 (7) |
C2 | 0.0212 (8) | 0.0301 (9) | 0.0280 (9) | 0.0028 (7) | −0.0026 (7) | 0.0008 (7) |
C3 | 0.0305 (10) | 0.0492 (12) | 0.0252 (9) | 0.0062 (9) | 0.0015 (8) | 0.0038 (8) |
C4 | 0.0293 (9) | 0.0522 (13) | 0.0362 (10) | −0.0005 (9) | 0.0023 (9) | 0.0165 (10) |
C5 | 0.0283 (9) | 0.0368 (11) | 0.0453 (11) | −0.0060 (8) | −0.0062 (9) | 0.0110 (9) |
C6 | 0.0267 (9) | 0.0311 (9) | 0.0303 (9) | 0.0009 (7) | −0.0052 (7) | 0.0017 (8) |
C7 | 0.0218 (9) | 0.0407 (11) | 0.0262 (9) | −0.0048 (8) | 0.0024 (7) | −0.0007 (8) |
O1 | 0.0210 (6) | 0.0572 (10) | 0.0318 (7) | −0.0045 (6) | −0.0021 (5) | 0.0101 (7) |
Cl1 | 0.0287 (4) | 0.0277 (4) | 0.0255 (4) | −0.0023 (4) | −0.0007 (3) | −0.0052 (3) |
Cl2 | 0.0423 (5) | 0.0302 (4) | 0.0317 (5) | −0.0033 (3) | −0.0041 (3) | −0.0080 (4) |
F1 | 0.056 (6) | 0.062 (7) | 0.068 (6) | −0.006 (4) | −0.013 (4) | −0.010 (4) |
F2 | 0.054 (4) | 0.084 (8) | 0.057 (5) | 0.007 (4) | 0.002 (3) | −0.032 (4) |
N1 | 0.0162 (7) | 0.0373 (9) | 0.0255 (7) | −0.0017 (6) | −0.0005 (6) | −0.0026 (6) |
C1—C2 | 1.392 (2) | C4—H4 | 0.95 |
C1—C6 | 1.396 (3) | C5—C6 | 1.380 (3) |
C1—N1 | 1.411 (2) | C5—H5 | 0.95 |
C2—F1 | 1.358 (5) | C6—F2 | 1.351 (5) |
C2—C3 | 1.380 (3) | C6—Cl2 | 1.728 (2) |
C2—Cl1 | 1.721 (2) | C7—O1 | 1.222 (2) |
C3—C4 | 1.382 (3) | C7—N1 | 1.341 (2) |
C3—H3 | 0.95 | C7—H7 | 0.95 |
C4—C5 | 1.382 (3) | N1—H1 | 0.87 (3) |
C2—C1—C6 | 116.82 (17) | C6—C5—C4 | 119.6 (2) |
C2—C1—N1 | 121.02 (16) | C6—C5—H5 | 120.2 |
C6—C1—N1 | 122.12 (16) | C4—C5—H5 | 120.2 |
F1—C2—C3 | 119.7 (4) | F2—C6—C5 | 121.2 (4) |
F1—C2—C1 | 117.8 (4) | F2—C6—C1 | 117.0 (4) |
C3—C2—C1 | 122.48 (18) | C5—C6—C1 | 121.70 (18) |
C3—C2—Cl1 | 118.72 (16) | C5—C6—Cl2 | 117.76 (16) |
C1—C2—Cl1 | 118.78 (15) | C1—C6—Cl2 | 120.47 (15) |
C2—C3—C4 | 118.92 (19) | O1—C7—N1 | 125.91 (18) |
C2—C3—H3 | 120.5 | O1—C7—H7 | 117 |
C4—C3—H3 | 120.5 | N1—C7—H7 | 117 |
C3—C4—C5 | 120.48 (19) | C7—N1—C1 | 123.17 (15) |
C3—C4—H4 | 119.8 | C7—N1—H1 | 118.5 (15) |
C5—C4—H4 | 119.8 | C1—N1—H1 | 117.9 (15) |
C6—C1—C2—F1 | 179.1 (5) | C4—C5—C6—C1 | 1.9 (3) |
N1—C1—C2—F1 | −3.2 (5) | C4—C5—C6—Cl2 | −175.03 (17) |
C6—C1—C2—C3 | 0.03 (16) | C2—C1—C6—F2 | −178.5 (5) |
N1—C1—C2—C3 | 177.82 (16) | N1—C1—C6—F2 | 3.7 (5) |
C6—C1—C2—Cl1 | −178.47 (14) | C2—C1—C6—C5 | −1.4 (2) |
N1—C1—C2—Cl1 | −0.69 (18) | N1—C1—C6—C5 | −179.16 (17) |
F1—C2—C3—C4 | −178.2 (5) | C2—C1—C6—Cl2 | 175.49 (12) |
C1—C2—C3—C4 | 0.77 (19) | N1—C1—C6—Cl2 | −2.3 (2) |
Cl1—C2—C3—C4 | 179.27 (16) | O1—C7—N1—C1 | 1.3 (3) |
C2—C3—C4—C5 | −0.2 (3) | C2—C1—N1—C7 | 116.98 (18) |
C3—C4—C5—C6 | −1.1 (3) | C6—C1—N1—C7 | −65.4 (2) |
C4—C5—C6—F2 | 178.9 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.87 (3) | 1.98 (3) | 2.848 (2) | 172 (2) |
C4—H4···O1ii | 0.95 | 2.70 | 3.540 (3) | 148 |
Symmetry codes: (i) x−1/2, y, −z+3/2; (ii) −x+3/2, −y+1, z−1/2. |
C8.03H8.10Cl0.97NO | F(000) = 702.0 |
Mr = 168.95 | Dx = 1.395 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 1886 reflections |
a = 8.5073 (12) Å | θ = 2.8–24.7° |
b = 13.093 (2) Å | µ = 0.40 mm−1 |
c = 14.448 (2) Å | T = 293 K |
V = 1609.3 (4) Å3 | Block, colourless |
Z = 8 | 0.36 × 0.25 × 0.15 mm |
Bruker SMART 1K CCD area detector diffractometer | 972 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
ω scans | θmax = 25.5°, θmin = 2.8° |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | h = −3→10 |
Tmin = 0.89, Tmax = 0.94 | k = −15→15 |
7672 measured reflections | l = −17→17 |
1475 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.154 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.86 | w = 1/[σ2(Fo2) + (0.0849P)2 + 1.8237P] where P = (Fo2 + 2Fc2)/3 |
1475 reflections | (Δ/σ)max < 0.001 |
124 parameters | Δρmax = 0.16 e Å−3 |
26 restraints | Δρmin = −0.20 e Å−3 |
C8.03H8.10Cl0.97NO | V = 1609.3 (4) Å3 |
Mr = 168.95 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 8.5073 (12) Å | µ = 0.40 mm−1 |
b = 13.093 (2) Å | T = 293 K |
c = 14.448 (2) Å | 0.36 × 0.25 × 0.15 mm |
Bruker SMART 1K CCD area detector diffractometer | 1475 independent reflections |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | 972 reflections with I > 2σ(I) |
Tmin = 0.89, Tmax = 0.94 | Rint = 0.043 |
7672 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 26 restraints |
wR(F2) = 0.154 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.86 | Δρmax = 0.16 e Å−3 |
1475 reflections | Δρmin = −0.20 e Å−3 |
124 parameters |
Experimental. absorption corrections were made using the program SADABS (Sheldrick, 1996). |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.4461 (3) | 0.4211 (2) | 0.64854 (18) | 0.0422 (7) | |
C2 | 0.3610 (3) | 0.5098 (2) | 0.66262 (19) | 0.0504 (8) | |
C3 | 0.2593 (3) | 0.5452 (3) | 0.5950 (2) | 0.0656 (10) | |
H3 | 0.2015 | 0.6045 | 0.6049 | 0.079* | |
C4 | 0.2440 (4) | 0.4924 (3) | 0.5131 (2) | 0.0707 (11) | |
H4 | 0.1753 | 0.5161 | 0.4679 | 0.085* | |
C5 | 0.3294 (4) | 0.4051 (3) | 0.4977 (2) | 0.0626 (10) | |
H5 | 0.32 | 0.3707 | 0.4416 | 0.075* | |
C6 | 0.4295 (3) | 0.3681 (2) | 0.5655 (2) | 0.0472 (8) | |
C7 | 0.5081 (3) | 0.3470 (3) | 0.7984 (2) | 0.0529 (8) | |
H7 | 0.5873 | 0.3225 | 0.8368 | 0.063* | |
N1 | 0.5513 (3) | 0.3835 (2) | 0.71673 (17) | 0.0472 (7) | |
H1 | 0.645 (4) | 0.376 (2) | 0.700 (2) | 0.057* | |
O1 | 0.3740 (2) | 0.3425 (2) | 0.82761 (15) | 0.0710 (8) | |
Cl1 | 0.3873 (6) | 0.5805 (3) | 0.7605 (3) | 0.0717 (14) | 0.484 (6) |
Cl2 | 0.5368 (4) | 0.2580 (3) | 0.5438 (3) | 0.0604 (10) | 0.484 (6) |
C8 | 0.3797 (18) | 0.5706 (11) | 0.7505 (6) | 0.075 (7) | 0.516 (6) |
H8A | 0.4893 | 0.5827 | 0.7619 | 0.113* | 0.516 (6) |
H8B | 0.3355 | 0.5332 | 0.8014 | 0.113* | 0.516 (6) |
H8C | 0.3261 | 0.6348 | 0.7443 | 0.113* | 0.516 (6) |
C9 | 0.5223 (14) | 0.2716 (6) | 0.5499 (11) | 0.085 (8) | 0.516 (6) |
H9A | 0.5124 | 0.228 | 0.6031 | 0.127* | 0.516 (6) |
H9B | 0.631 | 0.2884 | 0.5406 | 0.127* | 0.516 (6) |
H9C | 0.4826 | 0.2368 | 0.4963 | 0.127* | 0.516 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0314 (13) | 0.0570 (18) | 0.0382 (15) | −0.0030 (13) | 0.0032 (11) | 0.0049 (13) |
C2 | 0.0417 (15) | 0.0596 (19) | 0.0500 (17) | −0.0023 (14) | 0.0051 (13) | 0.0079 (14) |
C3 | 0.0507 (18) | 0.075 (2) | 0.071 (2) | 0.0102 (17) | 0.0103 (18) | 0.028 (2) |
C4 | 0.0510 (18) | 0.105 (3) | 0.056 (2) | −0.003 (2) | −0.0088 (17) | 0.033 (2) |
C5 | 0.0517 (17) | 0.093 (3) | 0.0432 (17) | −0.0184 (19) | −0.0058 (15) | 0.0094 (18) |
C6 | 0.0411 (15) | 0.0582 (19) | 0.0422 (16) | −0.0113 (14) | 0.0031 (13) | 0.0028 (14) |
C7 | 0.0403 (15) | 0.075 (2) | 0.0435 (17) | 0.0089 (14) | −0.0066 (14) | 0.0028 (15) |
N1 | 0.0316 (11) | 0.0666 (17) | 0.0434 (14) | 0.0028 (12) | 0.0003 (11) | −0.0007 (12) |
O1 | 0.0417 (12) | 0.116 (2) | 0.0559 (14) | 0.0112 (12) | 0.0059 (10) | 0.0242 (13) |
Cl1 | 0.083 (3) | 0.068 (2) | 0.064 (2) | 0.012 (2) | 0.0043 (19) | −0.0125 (16) |
Cl2 | 0.0648 (17) | 0.0609 (17) | 0.055 (2) | −0.0034 (14) | 0.0019 (14) | −0.0089 (14) |
C8 | 0.072 (11) | 0.059 (9) | 0.095 (13) | 0.003 (7) | 0.017 (8) | −0.037 (8) |
C9 | 0.114 (14) | 0.080 (12) | 0.060 (10) | −0.019 (8) | 0.026 (8) | −0.026 (7) |
C1—C2 | 1.384 (4) | C6—C9 | 1.507 (5) |
C1—C6 | 1.394 (4) | C6—Cl2 | 1.735 (5) |
C1—N1 | 1.419 (4) | C7—O1 | 1.218 (4) |
C2—C3 | 1.385 (4) | C7—N1 | 1.325 (4) |
C2—C8 | 1.507 (5) | C7—H7 | 0.93 |
C2—Cl1 | 1.705 (5) | N1—H1 | 0.84 (4) |
C3—C4 | 1.376 (5) | C8—H8A | 0.96 |
C3—H3 | 0.93 | C8—H8B | 0.96 |
C4—C5 | 1.373 (5) | C8—H8C | 0.96 |
C4—H4 | 0.93 | C9—H9A | 0.96 |
C5—C6 | 1.385 (4) | C9—H9B | 0.96 |
C5—H5 | 0.93 | C9—H9C | 0.96 |
C2—C1—C6 | 119.4 (3) | C5—C6—Cl2 | 119.1 (3) |
C2—C1—N1 | 121.2 (3) | C1—C6—Cl2 | 121.1 (3) |
C6—C1—N1 | 119.3 (3) | O1—C7—N1 | 125.9 (3) |
C1—C2—C3 | 120.2 (3) | O1—C7—H7 | 117.1 |
C1—C2—C8 | 120.8 (7) | N1—C7—H7 | 117.1 |
C3—C2—C8 | 118.9 (7) | C7—N1—C1 | 124.6 (2) |
C1—C2—Cl1 | 120.6 (3) | C7—N1—H1 | 119 (2) |
C3—C2—Cl1 | 119.1 (3) | C1—N1—H1 | 116 (2) |
C4—C3—C2 | 119.9 (3) | C2—C8—H8A | 109.5 |
C4—C3—H3 | 120.1 | C2—C8—H8B | 109.5 |
C2—C3—H3 | 120.1 | H8A—C8—H8B | 109.5 |
C5—C4—C3 | 120.5 (3) | C2—C8—H8C | 109.5 |
C5—C4—H4 | 119.7 | H8A—C8—H8C | 109.5 |
C3—C4—H4 | 119.7 | H8B—C8—H8C | 109.5 |
C4—C5—C6 | 120.1 (3) | C6—C9—H9A | 109.5 |
C4—C5—H5 | 119.9 | C6—C9—H9B | 109.5 |
C6—C5—H5 | 119.9 | H9A—C9—H9B | 109.5 |
C5—C6—C1 | 119.8 (3) | C6—C9—H9C | 109.5 |
C5—C6—C9 | 120.7 (7) | H9A—C9—H9C | 109.5 |
C1—C6—C9 | 119.5 (7) | H9B—C9—H9C | 109.5 |
C6—C1—C2—C3 | 0.5 (2) | C4—C5—C6—C9 | 179.2 (6) |
N1—C1—C2—C3 | 179.8 (2) | C4—C5—C6—Cl2 | −179.6 (3) |
C6—C1—C2—C8 | −178.2 (6) | C2—C1—C6—C5 | 0.6 (3) |
N1—C1—C2—C8 | 1.1 (6) | N1—C1—C6—C5 | −178.7 (2) |
C6—C1—C2—Cl1 | −176.1 (3) | C2—C1—C6—C9 | 179.9 (5) |
N1—C1—C2—Cl1 | 3.2 (3) | N1—C1—C6—C9 | 0.5 (6) |
C1—C2—C3—C4 | −0.6 (2) | C2—C1—C6—Cl2 | 178.6 (2) |
C8—C2—C3—C4 | 178.1 (6) | N1—C1—C6—Cl2 | −0.7 (3) |
Cl1—C2—C3—C4 | 176.0 (3) | O1—C7—N1—C1 | −1.9 (5) |
C2—C3—C4—C5 | −0.3 (4) | C2—C1—N1—C7 | 67.7 (4) |
C3—C4—C5—C6 | 1.4 (5) | C6—C1—N1—C7 | −113.0 (3) |
C4—C5—C6—C1 | −1.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.84 (4) | 2.03 (4) | 2.870 (3) | 172 (3) |
C4—H4···O1ii | 0.93 | 2.78 | 3.586 (4) | 146 |
Symmetry codes: (i) x+1/2, y, −z+3/2; (ii) −x+1/2, −y+1, z−1/2. |
C8.78H10.35Cl0.22NS | F(000) = 718.0 |
Mr = 169.71 | Dx = 1.275 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 8770 reflections |
a = 9.2080 (1) Å | θ = 2.8–28.3° |
b = 13.1420 (2) Å | µ = 0.37 mm−1 |
c = 14.6170 (3) Å | T = 123 K |
V = 1768.83 (5) Å3 | Block, colourless |
Z = 8 | 0.37 × 0.17 × 0.14 mm |
Bruker SMART 1K CCD area detector diffractometer | 1755 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.064 |
ω scans | θmax = 28.0°, θmin = 2.8° |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | h = −11→12 |
Tmin = 0.673, Tmax = 0.854 | k = −17→17 |
21156 measured reflections | l = −19→17 |
2133 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0542P)2 + 0.3573P] where P = (Fo2 + 2Fc2)/3 |
2133 reflections | (Δ/σ)max = 0.001 |
124 parameters | Δρmax = 0.35 e Å−3 |
26 restraints | Δρmin = −0.23 e Å−3 |
C8.78H10.35Cl0.22NS | V = 1768.83 (5) Å3 |
Mr = 169.71 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 9.2080 (1) Å | µ = 0.37 mm−1 |
b = 13.1420 (2) Å | T = 123 K |
c = 14.6170 (3) Å | 0.37 × 0.17 × 0.14 mm |
Bruker SMART 1K CCD area detector diffractometer | 2133 independent reflections |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | 1755 reflections with I > 2σ(I) |
Tmin = 0.673, Tmax = 0.854 | Rint = 0.064 |
21156 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 26 restraints |
wR(F2) = 0.097 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.35 e Å−3 |
2133 reflections | Δρmin = −0.23 e Å−3 |
124 parameters |
Experimental. absorption corrections were made using the program SADABS (Sheldrick, 1996). |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.55804 (13) | 0.55512 (9) | 0.64640 (9) | 0.0252 (3) | |
C2 | 0.64515 (15) | 0.46993 (10) | 0.66053 (10) | 0.0329 (3) | |
C3 | 0.75280 (16) | 0.45029 (12) | 0.59583 (12) | 0.0439 (4) | |
H3 | 0.814 | 0.3927 | 0.6032 | 0.053* | |
C4 | 0.77186 (17) | 0.51311 (14) | 0.52130 (11) | 0.0471 (4) | |
H4 | 0.8466 | 0.4987 | 0.4784 | 0.057* | |
C5 | 0.68401 (16) | 0.59646 (12) | 0.50818 (10) | 0.0392 (4) | |
H5 | 0.6978 | 0.6387 | 0.4562 | 0.047* | |
C6 | 0.57488 (14) | 0.61907 (10) | 0.57098 (9) | 0.0273 (3) | |
C7 | 0.46278 (13) | 0.62695 (10) | 0.78809 (9) | 0.0253 (3) | |
H7 | 0.3771 | 0.6428 | 0.8214 | 0.03* | |
N1 | 0.44466 (11) | 0.57881 (8) | 0.71005 (8) | 0.0253 (3) | |
H1 | 0.3577 (18) | 0.5705 (12) | 0.6904 (11) | 0.03* | |
S1 | 0.61767 (3) | 0.66288 (3) | 0.83460 (2) | 0.02916 (14) | |
C8 | 0.6217 (4) | 0.4031 (3) | 0.7421 (2) | 0.0393 (9) | 0.891 (2) |
H8A | 0.6959 | 0.3497 | 0.7432 | 0.059* | 0.891 (2) |
H8B | 0.5252 | 0.3719 | 0.7385 | 0.059* | 0.891 (2) |
H8C | 0.6286 | 0.444 | 0.798 | 0.059* | 0.891 (2) |
C9 | 0.4758 (5) | 0.7093 (3) | 0.5580 (3) | 0.0376 (9) | 0.891 (2) |
H9A | 0.5101 | 0.7502 | 0.5063 | 0.056* | 0.891 (2) |
H9B | 0.4759 | 0.7509 | 0.6137 | 0.056* | 0.891 (2) |
H9C | 0.3769 | 0.6854 | 0.5457 | 0.056* | 0.891 (2) |
Cl1 | 0.6193 (11) | 0.3934 (6) | 0.7553 (5) | 0.053 (3) | 0.109 (2) |
Cl2 | 0.4636 (9) | 0.7248 (5) | 0.5563 (7) | 0.036 (2) | 0.109 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0192 (6) | 0.0264 (6) | 0.0301 (7) | −0.0056 (5) | −0.0032 (5) | −0.0057 (5) |
C2 | 0.0268 (7) | 0.0283 (7) | 0.0437 (9) | −0.0022 (5) | −0.0100 (6) | −0.0113 (6) |
C3 | 0.0326 (8) | 0.0410 (8) | 0.0580 (11) | 0.0077 (6) | −0.0116 (7) | −0.0280 (8) |
C4 | 0.0348 (8) | 0.0667 (11) | 0.0398 (9) | −0.0031 (8) | 0.0037 (7) | −0.0309 (9) |
C5 | 0.0363 (8) | 0.0534 (9) | 0.0279 (8) | −0.0109 (7) | 0.0050 (6) | −0.0151 (7) |
C6 | 0.0249 (6) | 0.0321 (7) | 0.0250 (7) | −0.0085 (5) | −0.0014 (5) | −0.0073 (6) |
C7 | 0.0191 (6) | 0.0288 (6) | 0.0279 (7) | 0.0043 (5) | 0.0055 (5) | 0.0104 (5) |
N1 | 0.0146 (5) | 0.0295 (6) | 0.0317 (6) | −0.0040 (4) | −0.0016 (4) | 0.0077 (5) |
S1 | 0.0217 (2) | 0.0388 (2) | 0.0270 (2) | 0.00552 (13) | −0.00093 (12) | −0.00606 (14) |
C8 | 0.0338 (16) | 0.0179 (13) | 0.066 (2) | 0.0010 (11) | −0.0140 (14) | 0.0100 (13) |
C9 | 0.052 (2) | 0.0414 (16) | 0.0198 (16) | −0.0185 (12) | 0.0011 (13) | 0.0060 (12) |
Cl1 | 0.066 (5) | 0.027 (3) | 0.065 (4) | 0.003 (3) | −0.020 (3) | 0.016 (3) |
Cl2 | 0.040 (3) | 0.027 (2) | 0.042 (4) | −0.006 (2) | −0.001 (3) | 0.012 (2) |
C1—C2 | 1.3926 (19) | C6—C9 | 1.508 (3) |
C1—C6 | 1.3949 (19) | C6—Cl2 | 1.740 (4) |
C1—N1 | 1.4326 (17) | C7—N1 | 1.3151 (18) |
C2—C3 | 1.394 (2) | C7—S1 | 1.6490 (13) |
C2—C8 | 1.497 (3) | C7—H7 | 0.95 |
C2—Cl1 | 1.729 (4) | N1—H1 | 0.858 (16) |
C3—C4 | 1.378 (3) | C8—H8A | 0.98 |
C3—H3 | 0.95 | C8—H8B | 0.98 |
C4—C5 | 1.375 (2) | C8—H8C | 0.98 |
C4—H4 | 0.95 | C9—H9A | 0.98 |
C5—C6 | 1.3931 (19) | C9—H9B | 0.98 |
C5—H5 | 0.95 | C9—H9C | 0.98 |
C2—C1—C6 | 122.52 (13) | C5—C6—C1 | 118.19 (13) |
C2—C1—N1 | 119.87 (12) | C5—C6—C9 | 121.4 (2) |
C6—C1—N1 | 117.60 (11) | C1—C6—C9 | 120.4 (2) |
C1—C2—C3 | 117.24 (14) | C5—C6—Cl2 | 120.9 (3) |
C1—C2—C8 | 120.4 (2) | C1—C6—Cl2 | 120.9 (3) |
C3—C2—C8 | 122.3 (2) | N1—C7—S1 | 127.23 (10) |
C1—C2—Cl1 | 120.5 (3) | N1—C7—H7 | 116.4 |
C3—C2—Cl1 | 122.3 (3) | S1—C7—H7 | 116.4 |
C4—C3—C2 | 121.06 (15) | C7—N1—C1 | 125.13 (10) |
C4—C3—H3 | 119.5 | C7—N1—H1 | 118.0 (11) |
C2—C3—H3 | 119.5 | C1—N1—H1 | 115.8 (11) |
C5—C4—C3 | 120.83 (15) | C2—C8—H8A | 109.5 |
C5—C4—H4 | 119.6 | C2—C8—H8B | 109.5 |
C3—C4—H4 | 119.6 | C2—C8—H8C | 109.5 |
C4—C5—C6 | 120.16 (15) | C6—C9—H9A | 109.5 |
C4—C5—H5 | 119.9 | C6—C9—H9B | 109.5 |
C6—C5—H5 | 119.9 | C6—C9—H9C | 109.5 |
C6—C1—C2—C3 | 0.37 (13) | C4—C5—C6—C9 | −179.4 (2) |
N1—C1—C2—C3 | 179.43 (11) | C4—C5—C6—Cl2 | 179.4 (4) |
C6—C1—C2—C8 | −179.4 (2) | C2—C1—C6—C5 | −0.44 (17) |
N1—C1—C2—C8 | −0.3 (2) | N1—C1—C6—C5 | −179.51 (11) |
C6—C1—C2—Cl1 | 180.0 (4) | C2—C1—C6—C9 | 178.9 (2) |
N1—C1—C2—Cl1 | −1.0 (4) | N1—C1—C6—C9 | −0.2 (3) |
C1—C2—C3—C4 | 0.20 (15) | C2—C1—C6—Cl2 | −179.9 (4) |
C8—C2—C3—C4 | 179.9 (2) | N1—C1—C6—Cl2 | 1.0 (4) |
Cl1—C2—C3—C4 | −179.4 (4) | S1—C7—N1—C1 | −5.15 (19) |
C2—C3—C4—C5 | −0.7 (2) | C2—C1—N1—C7 | 81.77 (15) |
C3—C4—C5—C6 | 0.6 (2) | C6—C1—N1—C7 | −99.13 (15) |
C4—C5—C6—C1 | −0.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···S1i | 0.858 (16) | 2.548 (17) | 3.2730 (11) | 142.9 (14) |
Symmetry code: (i) x−1/2, y, −z+3/2. |
C13H19NO0.54S0.46 | F(000) = 464 |
Mr = 213.32 | Dx = 1.119 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 886 reflections |
a = 9.022 (1) Å | θ = 2.6–24.7° |
b = 9.0030 (9) Å | µ = 0.15 mm−1 |
c = 16.0050 (16) Å | T = 173 K |
β = 103.170 (5)° | Block, colourless |
V = 1265.8 (2) Å3 | 0.43 × 0.18 × 0.14 mm |
Z = 4 |
Bruker SMART 1K CCD area detector diffractometer | 1775 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.095 |
ω scans | θmax = 28°, θmin = 2.3° |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | h = −8→11 |
Tmin = 0.940, Tmax = 0.980 | k = −11→11 |
15410 measured reflections | l = −21→20 |
3055 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.200 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0912P)2 + 0.2341P] where P = (Fo2 + 2Fc2)/3 |
3055 reflections | (Δ/σ)max = 0.005 |
144 parameters | Δρmax = 0.55 e Å−3 |
4 restraints | Δρmin = −0.61 e Å−3 |
C13H19NO0.54S0.46 | V = 1265.8 (2) Å3 |
Mr = 213.32 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.022 (1) Å | µ = 0.15 mm−1 |
b = 9.0030 (9) Å | T = 173 K |
c = 16.0050 (16) Å | 0.43 × 0.18 × 0.14 mm |
β = 103.170 (5)° |
Bruker SMART 1K CCD area detector diffractometer | 3055 independent reflections |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | 1775 reflections with I > 2σ(I) |
Tmin = 0.940, Tmax = 0.980 | Rint = 0.095 |
15410 measured reflections |
R[F2 > 2σ(F2)] = 0.065 | 4 restraints |
wR(F2) = 0.200 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | Δρmax = 0.55 e Å−3 |
3055 reflections | Δρmin = −0.61 e Å−3 |
144 parameters |
Experimental. absorption corrections were made using the program SADABS (Sheldrick, 1996). |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.4452 (3) | 0.6580 (2) | 0.33206 (13) | 0.0334 (5) | |
C2 | 0.5503 (2) | 0.7077 (2) | 0.40549 (13) | 0.0324 (5) | |
C3 | 0.4944 (3) | 0.7971 (2) | 0.46274 (13) | 0.0379 (6) | |
H3 | 0.5623 | 0.8322 | 0.5132 | 0.046* | |
C4 | 0.3418 (3) | 0.8355 (2) | 0.44724 (15) | 0.0410 (6) | |
H4 | 0.3064 | 0.8972 | 0.4868 | 0.049* | |
C5 | 0.2408 (3) | 0.7847 (2) | 0.37475 (15) | 0.0402 (6) | |
H5 | 0.1364 | 0.8113 | 0.3652 | 0.048* | |
C6 | 0.2898 (3) | 0.6950 (2) | 0.31531 (14) | 0.0381 (5) | |
C7 | 0.5694 (3) | 0.5958 (3) | 0.21717 (15) | 0.0580 (7) | |
H7 | 0.5947 | 0.5163 | 0.184 | 0.07* | |
C8 | 0.7169 (3) | 0.6614 (3) | 0.42630 (14) | 0.0386 (5) | |
H8 | 0.737 | 0.6077 | 0.3753 | 0.046* | |
C9 | 0.1786 (3) | 0.6403 (3) | 0.23433 (17) | 0.0546 (7) | |
H9 | 0.2146 | 0.5403 | 0.2203 | 0.066* | |
C10 | 0.8247 (3) | 0.7948 (3) | 0.44432 (19) | 0.0565 (7) | |
H10A | 0.9303 | 0.7598 | 0.4573 | 0.085* | |
H10B | 0.8058 | 0.8505 | 0.4935 | 0.085* | |
H10C | 0.807 | 0.8594 | 0.3938 | 0.085* | |
C11 | 0.7507 (3) | 0.5547 (3) | 0.5024 (2) | 0.0687 (9) | |
H11A | 0.8583 | 0.5262 | 0.5147 | 0.103* | |
H11B | 0.6871 | 0.4659 | 0.4887 | 0.103* | |
H11C | 0.7284 | 0.6037 | 0.5529 | 0.103* | |
C12 | 0.0164 (4) | 0.6213 (4) | 0.2460 (2) | 0.0974 (13) | |
H12A | 0.0171 | 0.5555 | 0.2948 | 0.146* | |
H12B | −0.0473 | 0.5778 | 0.1939 | 0.146* | |
H12C | −0.0247 | 0.7184 | 0.2567 | 0.146* | |
C13 | 0.1813 (4) | 0.7421 (4) | 0.15842 (18) | 0.0696 (9) | |
H13A | 0.1096 | 0.705 | 0.1072 | 0.104* | |
H13B | 0.2841 | 0.744 | 0.148 | 0.104* | |
H13C | 0.1518 | 0.8428 | 0.1713 | 0.104* | |
O1 | 0.6117 (5) | 0.7179 (3) | 0.2009 (3) | 0.0324 (12)* | 0.536 (6) |
S1 | 0.6322 (3) | 0.7584 (3) | 0.19902 (13) | 0.0522 (7) | 0.464 (6) |
N1 | 0.4957 (2) | 0.5608 (2) | 0.27287 (12) | 0.0440 (5) | |
H1 | 0.471 (3) | 0.469 (3) | 0.2750 (16) | 0.053* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0420 (13) | 0.0245 (10) | 0.0340 (11) | −0.0007 (9) | 0.0096 (9) | −0.0021 (8) |
C2 | 0.0407 (12) | 0.0269 (10) | 0.0303 (10) | −0.0033 (9) | 0.0098 (9) | 0.0013 (8) |
C3 | 0.0512 (14) | 0.0373 (12) | 0.0275 (11) | −0.0042 (11) | 0.0136 (10) | −0.0019 (9) |
C4 | 0.0582 (15) | 0.0306 (12) | 0.0421 (13) | 0.0011 (11) | 0.0279 (11) | 0.0017 (10) |
C5 | 0.0399 (13) | 0.0326 (12) | 0.0520 (14) | 0.0026 (10) | 0.0185 (11) | 0.0080 (10) |
C6 | 0.0423 (13) | 0.0272 (11) | 0.0437 (12) | −0.0040 (10) | 0.0073 (10) | 0.0026 (9) |
C7 | 0.0557 (16) | 0.0728 (19) | 0.0419 (13) | 0.0153 (15) | 0.0037 (12) | −0.0172 (14) |
C8 | 0.0416 (13) | 0.0425 (13) | 0.0311 (11) | 0.0019 (11) | 0.0074 (9) | −0.0024 (9) |
C9 | 0.0483 (16) | 0.0427 (14) | 0.0638 (17) | 0.0010 (12) | −0.0063 (12) | −0.0115 (12) |
C10 | 0.0435 (15) | 0.0529 (16) | 0.0699 (18) | −0.0066 (13) | 0.0060 (13) | 0.0079 (13) |
C11 | 0.0613 (18) | 0.0608 (18) | 0.084 (2) | 0.0162 (15) | 0.0175 (15) | 0.0348 (16) |
C12 | 0.068 (2) | 0.110 (3) | 0.105 (3) | −0.050 (2) | 0.001 (2) | −0.006 (2) |
C13 | 0.0585 (18) | 0.095 (2) | 0.0464 (15) | 0.0023 (17) | −0.0063 (13) | −0.0071 (16) |
S1 | 0.0771 (14) | 0.0321 (11) | 0.0495 (10) | −0.0104 (9) | 0.0190 (8) | 0.0099 (8) |
N1 | 0.0528 (13) | 0.0393 (11) | 0.0376 (11) | 0.0082 (10) | 0.0052 (9) | −0.0142 (9) |
C1—C2 | 1.405 (3) | C8—H8 | 1 |
C1—C6 | 1.406 (3) | C9—C12 | 1.526 (4) |
C1—N1 | 1.438 (3) | C9—C13 | 1.527 (4) |
C2—C3 | 1.397 (3) | C9—H9 | 1 |
C2—C8 | 1.522 (3) | C10—H10A | 0.98 |
C3—C4 | 1.386 (3) | C10—H10B | 0.98 |
C3—H3 | 0.95 | C10—H10C | 0.98 |
C4—C5 | 1.380 (3) | C11—H11A | 0.98 |
C4—H4 | 0.95 | C11—H11B | 0.98 |
C5—C6 | 1.394 (3) | C11—H11C | 0.98 |
C5—H5 | 0.95 | C12—H12A | 0.98 |
C6—C9 | 1.528 (3) | C12—H12B | 0.98 |
C7—O1 | 1.2111 (5) | C12—H12C | 0.98 |
C7—N1 | 1.267 (3) | C13—H13A | 0.98 |
C7—S1 | 1.6196 (2) | C13—H13B | 0.98 |
C7—H7 | 0.95 | C13—H13C | 0.98 |
C8—C11 | 1.527 (3) | N1—H1 | 0.86 (3) |
C8—C10 | 1.531 (3) | ||
C2—C1—C6 | 122.55 (19) | C13—C9—C6 | 110.8 (2) |
C2—C1—N1 | 119.34 (19) | C12—C9—H9 | 107.3 |
C6—C1—N1 | 118.06 (18) | C13—C9—H9 | 107.3 |
C3—C2—C1 | 117.1 (2) | C6—C9—H9 | 107.3 |
C3—C2—C8 | 120.02 (19) | C8—C10—H10A | 109.5 |
C1—C2—C8 | 122.74 (18) | C8—C10—H10B | 109.5 |
C4—C3—C2 | 121.2 (2) | H10A—C10—H10B | 109.5 |
C4—C3—H3 | 119.4 | C8—C10—H10C | 109.5 |
C2—C3—H3 | 119.4 | H10A—C10—H10C | 109.5 |
C5—C4—C3 | 120.4 (2) | H10B—C10—H10C | 109.5 |
C5—C4—H4 | 119.8 | C8—C11—H11A | 109.5 |
C3—C4—H4 | 119.8 | C8—C11—H11B | 109.5 |
C4—C5—C6 | 121.0 (2) | H11A—C11—H11B | 109.5 |
C4—C5—H5 | 119.5 | C8—C11—H11C | 109.5 |
C6—C5—H5 | 119.5 | H11A—C11—H11C | 109.5 |
C5—C6—C1 | 117.6 (2) | H11B—C11—H11C | 109.5 |
C5—C6—C9 | 121.1 (2) | C9—C12—H12A | 109.5 |
C1—C6—C9 | 121.2 (2) | C9—C12—H12B | 109.5 |
O1—C7—N1 | 128.2 (3) | H12A—C12—H12B | 109.5 |
O1—C7—S1 | 2.5 (3) | C9—C12—H12C | 109.5 |
N1—C7—S1 | 127.7 (2) | H12A—C12—H12C | 109.5 |
O1—C7—H7 | 115.9 | H12B—C12—H12C | 109.5 |
N1—C7—H7 | 115.9 | C9—C13—H13A | 109.5 |
S1—C7—H7 | 116.3 | C9—C13—H13B | 109.5 |
C2—C8—C11 | 110.8 (2) | H13A—C13—H13B | 109.5 |
C2—C8—C10 | 112.32 (19) | C9—C13—H13C | 109.5 |
C11—C8—C10 | 109.9 (2) | H13A—C13—H13C | 109.5 |
C2—C8—H8 | 107.9 | H13B—C13—H13C | 109.5 |
C11—C8—H8 | 107.9 | C7—N1—C1 | 127.4 (2) |
C10—C8—H8 | 107.9 | C7—N1—H1 | 116.8 (18) |
C12—C9—C13 | 110.7 (3) | C1—N1—H1 | 115.7 (18) |
C12—C9—C6 | 113.3 (2) | ||
C6—C1—C2—C3 | 0.0 (3) | N1—C1—C6—C9 | −3.1 (3) |
N1—C1—C2—C3 | −177.52 (19) | C3—C2—C8—C11 | 68.1 (3) |
C6—C1—C2—C8 | 176.67 (19) | C1—C2—C8—C11 | −108.5 (3) |
N1—C1—C2—C8 | −0.8 (3) | C3—C2—C8—C10 | −55.2 (3) |
C1—C2—C3—C4 | −0.3 (3) | C1—C2—C8—C10 | 128.2 (2) |
C8—C2—C3—C4 | −177.1 (2) | C5—C6—C9—C12 | −29.6 (4) |
C2—C3—C4—C5 | 0.6 (3) | C1—C6—C9—C12 | 151.1 (3) |
C3—C4—C5—C6 | −0.5 (3) | C5—C6—C9—C13 | 95.5 (3) |
C4—C5—C6—C1 | 0.2 (3) | C1—C6—C9—C13 | −83.8 (3) |
C4—C5—C6—C9 | −179.1 (2) | O1—C7—N1—C1 | −0.9 (4) |
C2—C1—C6—C5 | 0.1 (3) | S1—C7—N1—C1 | 2.2 (3) |
N1—C1—C6—C5 | 177.6 (2) | C2—C1—N1—C7 | −77.4 (3) |
C2—C1—C6—C9 | 179.4 (2) | C6—C1—N1—C7 | 105.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···S1i | 0.86 (3) | 2.19 (3) | 3.030 (3) | 165 (3) |
N1—H1···O1i | 0.86 (3) | 2.43 (3) | 3.291 (4) | 172 (2) |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |
Experimental details
(1) | (2) | (3) | (4) | |
Crystal data | ||||
Chemical formula | C7H5Cl1.46F0.54NO | C8.03H8.10Cl0.97NO | C8.78H10.35Cl0.22NS | C13H19NO0.54S0.46 |
Mr | 181.07 | 168.95 | 169.71 | 213.32 |
Crystal system, space group | Orthorhombic, Pbca | Orthorhombic, Pbca | Orthorhombic, Pbca | Monoclinic, P21/c |
Temperature (K) | 173 | 293 | 123 | 173 |
a, b, c (Å) | 8.5220 (2), 12.2910 (3), 14.3090 (4) | 8.5073 (12), 13.093 (2), 14.448 (2) | 9.2080 (1), 13.1420 (2), 14.6170 (3) | 9.022 (1), 9.0030 (9), 16.0050 (16) |
α, β, γ (°) | 90, 90, 90 | 90, 90, 90 | 90, 90, 90 | 90, 103.170 (5), 90 |
V (Å3) | 1498.78 (7) | 1609.3 (4) | 1768.83 (5) | 1265.8 (2) |
Z | 8 | 8 | 8 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.61 | 0.40 | 0.37 | 0.15 |
Crystal size (mm) | 0.45 × 0.19 × 0.18 | 0.36 × 0.25 × 0.15 | 0.37 × 0.17 × 0.14 | 0.43 × 0.18 × 0.14 |
Data collection | ||||
Diffractometer | Bruker SMART 1K CCD area detector diffractometer | Bruker SMART 1K CCD area detector diffractometer | Bruker SMART 1K CCD area detector diffractometer | Bruker SMART 1K CCD area detector diffractometer |
Absorption correction | Multi-scan SADABS (Sheldrick, 1996) | Multi-scan SADABS (Sheldrick, 1996) | Multi-scan SADABS (Sheldrick, 1996) | Multi-scan SADABS (Sheldrick, 1996) |
Tmin, Tmax | 0.765, 0.895 | 0.89, 0.94 | 0.673, 0.854 | 0.940, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17793, 1811, 1706 | 7672, 1475, 972 | 21156, 2133, 1755 | 15410, 3055, 1775 |
Rint | 0.052 | 0.043 | 0.064 | 0.095 |
(sin θ/λ)max (Å−1) | 0.661 | 0.606 | 0.660 | 0.661 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.090, 1.25 | 0.045, 0.154, 0.86 | 0.035, 0.097, 1.07 | 0.065, 0.200, 1.12 |
No. of reflections | 1811 | 1475 | 2133 | 3055 |
No. of parameters | 122 | 124 | 124 | 144 |
No. of restraints | 26 | 26 | 26 | 4 |
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) | 0.22, −0.22 | 0.16, −0.20 | 0.35, −0.23 | 0.55, −0.61 |
Computer programs: Bruker SMART, Bruker (1998), Bruker SAINT+, Bruker (1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999), WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.87 (3) | 1.98 (3) | 2.848 (2) | 172 (2) |
C4—H4···O1ii | 0.95 | 2.70 | 3.540 (3) | 148 |
Symmetry codes: (i) x−1/2, y, −z+3/2; (ii) −x+3/2, −y+1, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.84 (4) | 2.03 (4) | 2.870 (3) | 172 (3) |
C4—H4···O1ii | 0.93 | 2.78 | 3.586 (4) | 146 |
Symmetry codes: (i) x+1/2, y, −z+3/2; (ii) −x+1/2, −y+1, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···S1i | 0.858 (16) | 2.548 (17) | 3.2730 (11) | 142.9 (14) |
Symmetry code: (i) x−1/2, y, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···S1i | 0.86 (3) | 2.19 (3) | 3.030 (3) | 165 (3) |
N1—H1···O1i | 0.86 (3) | 2.43 (3) | 3.291 (4) | 172 (2) |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |