Supporting information
CCDC references: 134767; 134768; 134769; 134770
For all compounds, data collection: CAD4 (Enraf-Nonius, 1992); cell refinement: SET4 & CELDIM (Enraf-Nonius, 1992). Data reduction: DATRD2 in NRCVAX96 (Gabe et al., 1989) for (1), (3), (4); DATRD2 in NRCVAX96 (Gabe et al., 1989 1989) for (2). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: NRCVAX96 and SHELXL97 (Sheldrick, 1997b); molecular graphics: NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1998); software used to prepare material for publication: NRCVAX96, SHELXL97 and WORDPERFECT macro PRPCIF97 (Ferguson, 1997).
C12H10O2·C12H8N2 | ? #Insert any comments here. |
Mr = 366.40 | Dx = 1.315 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.7107 Å |
a = 13.0288 (17) Å | Cell parameters from 25 reflections |
b = 12.1865 (10) Å | θ = 9.8–18.8° |
c = 12.0778 (12) Å | µ = 0.09 mm−1 |
β = 105.199 (9)° | T = 294 K |
V = 1850.6 (3) Å3 | Lath, colorless |
Z = 4 | 0.42 × 0.31 × 0.12 mm |
F(000) = 768 |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.012 |
Radiation source: X-ray tube | θmax = 25.2°, θmin = 2.3° |
Graphite monochromator | h = −15→15 |
θ/2θ scans | k = 0→14 |
1748 measured reflections | l = 0→14 |
1678 independent reflections | 3 standard reflections every 120 min |
915 reflections with I > 2σ(I) | intensity decay: no decay, variation 0.5% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.099 | Calculated w = 1/[σ2(Fo2) + (0.0542P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max < 0.001 |
1678 reflections | Δρmax = 0.14 e Å−3 |
129 parameters | Δρmin = −0.13 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0049 (9) |
C12H10O2·C12H8N2 | V = 1850.6 (3) Å3 |
Mr = 366.40 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 13.0288 (17) Å | µ = 0.09 mm−1 |
b = 12.1865 (10) Å | T = 294 K |
c = 12.0778 (12) Å | 0.42 × 0.31 × 0.12 mm |
β = 105.199 (9)° |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.012 |
1748 measured reflections | 3 standard reflections every 120 min |
1678 independent reflections | intensity decay: no decay, variation 0.5% |
915 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.14 e Å−3 |
1678 reflections | Δρmin = −0.13 e Å−3 |
129 parameters |
Experimental. ? #Insert any special details here. |
Geometry. Mean plane data from last SHELXL run The site labelled as "INV" is the inversion centre at (1/4, 0.25 0.0) and the -0.0846 (14) Å displacement of this site from the mean plane of the phenolic ring shows that the two rings are "stepped" slightly (by 0.169 Å). Equivalent positions are: $1 1-X, Y, 0.5-Z $2 0.5-X, 0.5-Y, –Z Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 8.4764 (0.0079) x - 6.6901 (0.0053) y + 4.0560 (0.0079) z = 0.5312 (0.0037) * -0.0391 (0.0013) C11 * -0.0055 (0.0013) C12 * 0.0397 (0.0014) C13 * 0.0111 (0.0014) C14 * 0.0292 (0.0014) C15 * 0.0072 (0.0012) C16 * -0.0426 (0.0010) O14 - 0.1301 (0.0028) C11_$2 - 0.1637 (0.0032) C12_$2 - 0.2089 (0.0030) C13_$2 - 0.1803 (0.0029) C14_$2 - 0.1984 (0.0031) C15_$2 - 0.1764 (0.0031) C16_$2 - 0.1266 (0.0030) O14_$2 - 0.0846 (0.0014) INV Rms deviation of fitted atoms = 0.0292 8.4764 (0.0079) x - 6.6901 (0.0053) y + 4.0560 (0.0079) z = 0.3620 (0.0028) Angle to previous plane (with approximate e.s.d.) = 0.00 (0.12) * 0.0391 (0.0013) C11_$2 * 0.0055 (0.0013) C12_$2 * -0.0397 (0.0014) C13_$2 * -0.0111 (0.0014) C14_$2 * -0.0292 (0.0014) C15_$2 * -0.0072 (0.0012) C16_$2 * 0.0426 (0.0010) O14_$2 0.1301 (0.0028) C11 0.1637 (0.0032) C12 0.2089 (0.0030) C13 0.1803 (0.0029) C14 0.1984 (0.0031) C15 0.1764 (0.0031) C16 0.1266 (0.0030) O14 0.0846 (0.0014) INV Rms deviation of fitted atoms = 0.0292 12.5950 (0.0033) x - 0.0470 (0.0093) y - 6.0432 (0.0082) z = 4.7223 (0.0082) Angle to previous plane (with approximate e.s.d.) = 60.21 (0.05) * -0.0118 (0.0012) N1 * 0.0116 (0.0012) C2 * -0.0007 (0.0012) C3 * -0.0102 (0.0014) C4 * 0.0100 (0.0015) C5 * 0.0010 (0.0014) C6 - 0.0015 (0.0031) C7 0.0707 (0.0037) N1_$1 0.0381 (0.0034) C2_$1 0.0409 (0.0041) C3_$1 0.0506 (0.0043) C4_$1 0.0396 (0.0034) C5_$1 0.0576 (0.0041) C6_$1 0.0323 (0.0036) C7_$1 Rms deviation of fitted atoms = 0.0089 12.5950 (0.0033) x + 0.0470 (0.0093) y - 6.0432 (0.0082) z = 4.8511 (0.0089) Angle to previous plane (with approximate e.s.d.) = 0.44 (0.05) * 0.0118 (0.0012) N1_$1 * -0.0117 (0.0012) C2_$1 * 0.0007 (0.0012) C3_$1 * 0.0102 (0.0014) C4_$1 * -0.0100 (0.0015) C5_$1 * -0.0010 (0.0014) C6_$1 0.0015 (0.0031) C7_$1 - 0.0323 (0.0036) C7 - 0.0707 (0.0037) N1 - 0.0381 (0.0034) C2 - 0.0409 (0.0041) C3 - 0.0506 (0.0043) C4 - 0.0396 (0.0034) C5 - 0.0576 (0.0041) C6 Rms deviation of fitted atoms = 0.0089 |
x | y | z | Uiso*/Ueq | ||
N1 | 0.44259 (12) | 0.74375 (12) | 0.13717 (12) | 0.0563 (4) | |
C2 | 0.47035 (13) | 0.84112 (14) | 0.19040 (14) | 0.0481 (4) | |
C3 | 0.44280 (14) | 0.94214 (16) | 0.13423 (16) | 0.0568 (5) | |
C4 | 0.38652 (16) | 0.9395 (2) | 0.01853 (19) | 0.0703 (6) | |
C5 | 0.36177 (17) | 0.8425 (2) | −0.03565 (18) | 0.0744 (6) | |
C6 | 0.39058 (16) | 0.74627 (18) | 0.02664 (16) | 0.0684 (6) | |
C7 | 0.47228 (17) | 1.04284 (16) | 0.19502 (17) | 0.0722 (6) | |
C11 | 0.27194 (13) | 0.29537 (13) | 0.04021 (13) | 0.0426 (4) | |
C12 | 0.34504 (15) | 0.36973 (15) | 0.01837 (15) | 0.0558 (5) | |
C13 | 0.38423 (15) | 0.45618 (15) | 0.09022 (15) | 0.0576 (5) | |
C14 | 0.34859 (13) | 0.47393 (13) | 0.18692 (14) | 0.0468 (4) | |
C15 | 0.27948 (15) | 0.39957 (15) | 0.21315 (14) | 0.0534 (5) | |
C16 | 0.24227 (15) | 0.31224 (14) | 0.14145 (14) | 0.0526 (5) | |
O14 | 0.37876 (11) | 0.56258 (10) | 0.25684 (10) | 0.0604 (4) | |
H4 | 0.3661 | 1.0048 | −0.0211 | 0.084* | |
H5 | 0.3261 | 0.8400 | −0.1131 | 0.089* | |
H6 | 0.3724 | 0.6798 | −0.0112 | 0.082* | |
H7 | 0.4526 | 1.1092 | 0.1575 | 0.087* | |
H12 | 0.3684 | 0.3607 | −0.0475 | 0.067* | |
H13 | 0.4348 | 0.5028 | 0.0737 | 0.069* | |
H15 | 0.2575 | 0.4082 | 0.2800 | 0.064* | |
H16 | 0.1957 | 0.2629 | 0.1614 | 0.063* | |
H14 | 0.4119 | 0.6056 | 0.2270 | 0.091* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0546 (10) | 0.0565 (10) | 0.0546 (9) | −0.0030 (7) | 0.0087 (7) | −0.0013 (8) |
C2 | 0.0406 (10) | 0.0500 (11) | 0.0574 (10) | −0.0001 (8) | 0.0194 (8) | 0.0015 (9) |
C3 | 0.0491 (11) | 0.0567 (12) | 0.0699 (13) | 0.0070 (9) | 0.0250 (10) | 0.0130 (10) |
C4 | 0.0582 (13) | 0.0783 (16) | 0.0756 (15) | 0.0101 (11) | 0.0197 (11) | 0.0276 (13) |
C5 | 0.0633 (13) | 0.0963 (18) | 0.0585 (13) | 0.0013 (13) | 0.0070 (10) | 0.0201 (13) |
C6 | 0.0640 (13) | 0.0784 (15) | 0.0570 (12) | −0.0089 (11) | 0.0056 (10) | −0.0025 (11) |
C7 | 0.0861 (17) | 0.0481 (11) | 0.0932 (15) | 0.0081 (10) | 0.0430 (14) | 0.0108 (9) |
C11 | 0.0476 (10) | 0.0404 (9) | 0.0421 (9) | 0.0035 (7) | 0.0160 (8) | 0.0020 (7) |
C12 | 0.0650 (12) | 0.0560 (11) | 0.0551 (11) | −0.0083 (10) | 0.0314 (10) | −0.0111 (9) |
C13 | 0.0605 (12) | 0.0568 (12) | 0.0623 (12) | −0.0138 (9) | 0.0284 (10) | −0.0117 (9) |
C14 | 0.0483 (11) | 0.0464 (10) | 0.0433 (9) | 0.0014 (8) | 0.0077 (8) | −0.0061 (8) |
C15 | 0.0693 (13) | 0.0545 (11) | 0.0401 (10) | −0.0039 (10) | 0.0206 (9) | −0.0020 (8) |
C16 | 0.0668 (12) | 0.0492 (11) | 0.0458 (10) | −0.0075 (9) | 0.0218 (9) | 0.0031 (9) |
O14 | 0.0701 (9) | 0.0575 (8) | 0.0556 (8) | −0.0096 (7) | 0.0201 (6) | −0.0160 (7) |
N1—C2 | 1.353 (2) | C11—C11ii | 1.484 (3) |
N1—C6 | 1.330 (2) | C11—C12 | 1.389 (2) |
C2—C2i | 1.444 (3) | C11—C16 | 1.391 (2) |
C2—C3 | 1.406 (2) | C12—C13 | 1.375 (2) |
C3—C4 | 1.398 (3) | C13—C14 | 1.382 (2) |
C3—C7 | 1.430 (3) | C14—O14 | 1.3640 (19) |
C4—C5 | 1.349 (3) | C14—C15 | 1.372 (2) |
C5—C6 | 1.391 (3) | C15—C16 | 1.377 (2) |
C7—C7i | 1.335 (4) | ||
C6—N1—C2 | 117.34 (16) | C12—C11—C16 | 115.66 (15) |
N1—C2—C3 | 122.42 (16) | C12—C11—C11ii | 121.83 (18) |
N1—C2—C2i | 118.70 (9) | C16—C11—C11ii | 122.51 (19) |
C3—C2—C2i | 118.89 (11) | C13—C12—C11 | 122.65 (16) |
C4—C3—C2 | 117.59 (18) | C12—C13—C14 | 120.10 (17) |
C4—C3—C7 | 122.18 (18) | O14—C14—C15 | 118.71 (15) |
C2—C3—C7 | 120.23 (17) | O14—C14—C13 | 122.74 (16) |
C5—C4—C3 | 120.05 (19) | C15—C14—C13 | 118.55 (16) |
C4—C5—C6 | 118.7 (2) | C14—C15—C16 | 120.62 (15) |
N1—C6—C5 | 123.8 (2) | C15—C16—C11 | 122.26 (16) |
C7i—C7—C3 | 120.88 (11) | ||
C6—N1—C2—C3 | 2.4 (2) | C2—C3—C7—C7i | 1.1 (3) |
C6—N1—C2—C2i | −178.21 (19) | C16—C11—C12—C13 | −1.4 (3) |
N1—C2—C3—C4 | −1.3 (2) | C11ii—C11—C12—C13 | 178.07 (19) |
C2i—C2—C3—C4 | 179.26 (19) | C11—C12—C13—C14 | −2.0 (3) |
N1—C2—C3—C7 | 178.76 (17) | C12—C13—C14—O14 | −175.22 (16) |
C2i—C2—C3—C7 | −0.7 (3) | C12—C13—C14—C15 | 4.4 (3) |
C2—C3—C4—C5 | −0.9 (3) | O14—C14—C15—C16 | 176.33 (15) |
C7—C3—C4—C5 | 179.1 (2) | C13—C14—C15—C16 | −3.3 (3) |
C3—C4—C5—C6 | 1.8 (3) | C14—C15—C16—C11 | −0.3 (3) |
C2—N1—C6—C5 | −1.3 (3) | C12—C11—C16—C15 | 2.6 (3) |
C4—C5—C6—N1 | −0.8 (3) | C11ii—C11—C16—C15 | −176.92 (19) |
C4—C3—C7—C7i | −178.8 (2) |
Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+1/2, −y+1/2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O14—H14···N1 | 0.82 | 2.10 | 2.878 (2) | 159 |
C12—H12···O14iii | 0.93 | 2.58 | 3.403 (2) | 148 |
Symmetry code: (iii) x, −y+1, z−1/2. |
C12H10O2S·2(C12H8N2) | F(000) = 604 |
Mr = 578.69 | ? #Insert any comments here. |
Triclinic, P1 | Dx = 1.345 Mg m−3 |
a = 7.7342 (5) Å | Mo Kα radiation, λ = 0.7107 Å |
b = 13.3624 (14) Å | Cell parameters from 25 reflections |
c = 14.9843 (11) Å | θ = 9.6–18.6° |
α = 110.514 (6)° | µ = 0.16 mm−1 |
β = 95.195 (6)° | T = 294 K |
γ = 95.895 (7)° | Plate, colorless |
V = 1429.3 (2) Å3 | 0.42 × 0.35 × 0.22 mm |
Z = 2 |
Enraf-Nonius CAD-4 diffractometer | 3431 reflections with I > 2σ(I) |
Radiation source: X-ray tube | Rint = 0.000 |
Graphite monochromator | θmax = 25.2°, θmin = 2.0° |
θ/2θ scans | h = −9→9 |
Absorption correction: gaussian ABSORB in NRCVAX (Gabe et al., 1989) | k = 0→16 |
Tmin = 0.946, Tmax = 0.970 | l = −17→16 |
5184 measured reflections | 3 standard reflections every 120 min |
5184 independent reflections | intensity decay: no decay, variation 0.5% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.100 | Calculated w = 1/[σ2(Fo2) + (0.0561P)2 + 0.0505P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
5184 reflections | Δρmax = 0.20 e Å−3 |
391 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.030 (2) |
C12H10O2S·2(C12H8N2) | γ = 95.895 (7)° |
Mr = 578.69 | V = 1429.3 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.7342 (5) Å | Mo Kα radiation |
b = 13.3624 (14) Å | µ = 0.16 mm−1 |
c = 14.9843 (11) Å | T = 294 K |
α = 110.514 (6)° | 0.42 × 0.35 × 0.22 mm |
β = 95.195 (6)° |
Enraf-Nonius CAD-4 diffractometer | 3431 reflections with I > 2σ(I) |
Absorption correction: gaussian ABSORB in NRCVAX (Gabe et al., 1989) | Rint = 0.000 |
Tmin = 0.946, Tmax = 0.970 | 3 standard reflections every 120 min |
5184 measured reflections | intensity decay: no decay, variation 0.5% |
5184 independent reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.20 e Å−3 |
5184 reflections | Δρmin = −0.20 e Å−3 |
391 parameters |
Experimental. ? #Insert any special details here. |
Geometry. Mean-plane data ex last SHELXL refinement cycles: Equivalent position X, Y, 1+Z is represented by "_$1" Equivalent position 1+X, Y, 1+Z is represented by "_$2" Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 5.3694 (0.0057) x - 2.0612 (0.0154) y - 10.4299 (0.0094) z = 0.5325 (0.0031) * 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21 Rms deviation of fitted atoms = 0.0000 - 0.0967 (0.0045) x - 12.8590 (0.0031) y + 8.7118 (0.0077) z = 0.5712 (0.0016) Angle to previous plane (with approximate e.s.d.) = 83.97 (7) * -0.0637 (0.0013) C11 * -0.0553 (0.0013) C12 * -0.0315 (0.0013) C13 * 0.0114 (0.0014) C14 * -0.0263 (0.0014) C15 * -0.0656 (0.0013) C16 * 0.1323 (0.0008) S1 * 0.0986 (0.0010) O14 Rms deviation of fitted atoms = 0.0711 5.3694 (0.0057) x - 2.0612 (0.0154) y - 10.4299 (0.0094) z = 0.5325 (0.0031) Angle to previous plane (with approximate e.s.d.) = 83.97 (7) * 0.0000 (0.0000) S1 * 0.0000 (0.0000) C11 * 0.0000 (0.0000) C21 Rms deviation of fitted atoms = 0.0000 - 0.7552 (0.0050) x + 6.3615 (0.0039) y + 9.8018 (0.0043) z = 1.2464 (0.0015) Angle to previous plane (with approximate e.s.d.) = 42.73 (7) * 0.0529 (0.0013) C21 * 0.0373 (0.0012) C22 * -0.0245 (0.0013) C23 * -0.0242 (0.0014) C24 * -0.0046 (0.0013) C25 * 0.0121 (0.0013) C26 * -0.0501 (0.0008) S1 * 0.0010 (0.0011) O24 Rms deviation of fitted atoms = 0.0317 6.8549 (0.0015) x + 0.5658 (0.0029) y + 4.2342 (0.0048) z = 8.7640 (0.0025) Angle to previous plane (with approximate e.s.d.) = 68.56 (4) * -0.0111 (0.0012) N31 * -0.0050 (0.0013) C32 * 0.0041 (0.0014) C33 * 0.0178 (0.0016) C34 * 0.0040 (0.0016) C35 * -0.0110 (0.0015) C36 * 0.0057 (0.0014) C37 * 0.0024 (0.0012) N41 * -0.0070 (0.0013) C42 * -0.0114 (0.0014) C43 * -0.0148 (0.0014) C44 * 0.0093 (0.0015) C45 * 0.0204 (0.0014) C46 * -0.0031 (0.0014) C47 - 3.3465 (0.0020) N51_$1 - 3.3833 (0.0018) C52_$1 - 3.4187 (0.0018) C53_$1 - 3.4050 (0.0023) C54_$1 - 3.3891 (0.0026) C55_$1 - 3.3624 (0.0026) C56_$1 - 3.4999 (0.0019) C57_$1 - 3.3402 (0.0018) N61_$1 - 3.4134 (0.0017) C62_$1 - 3.5317 (0.0017) C63_$1 - 3.5990 (0.0021) C64_$1 - 3.5360 (0.0023) C65_$1 - 3.3971 (0.0024) C66_$1 - 3.5716 (0.0019) C67_$1 Rms deviation of fitted atoms = 0.0106 7.0177 (0.0014) x + 0.6706 (0.0039) y + 3.4781 (0.0057) z = 4.8711 (0.0032) Angle to previous plane (with approximate e.s.d.) = 3.08 (4) * -0.0094 (0.0013) N51_$1 * 0.0260 (0.0014) C52_$1 * 0.0365 (0.0015) C53_$1 * 0.0183 (0.0017) C54_$1 * -0.0382 (0.0018) C55_$1 * -0.0528 (0.0016) C56_$1 * 0.0307 (0.0015) C57_$1 * 0.0547 (0.0014) N61_$1 * 0.0269 (0.0014) C62_$1 * -0.0163 (0.0015) C63_$1 * -0.0556 (0.0017) C64_$1 * -0.0369 (0.0019) C65_$1 * 0.0282 (0.0017) C66_$1 * -0.0120 (0.0016) C67_$1 Rms deviation of fitted atoms = 0.0348 6.8549 (0.0015) x + 0.5658 (0.0029) y + 4.2342 (0.0048) z = 8.7640 (0.0025) Angle to previous plane (with approximate e.s.d.) = 3.08 (4) * -0.0111 (0.0012) N31 * -0.0050 (0.0013) C32 * 0.0041 (0.0014) C33 * 0.0178 (0.0016) C34 * 0.0040 (0.0016) C35 * -0.0110 (0.0015) C36 * 0.0057 (0.0014) C37 * 0.0024 (0.0012) N41 * -0.0070 (0.0013) C42 * -0.0114 (0.0014) C43 * -0.0148 (0.0014) C44 * 0.0093 (0.0015) C45 * 0.0204 (0.0014) C46 * -0.0031 (0.0014) C47 3.5084 (0.0015) N51_$2 3.4715 (0.0016) C52_$2 3.4362 (0.0018) C53_$2 3.4498 (0.0020) C54_$2 3.4658 (0.0022) C55_$2 3.4924 (0.0021) C56_$2 3.3550 (0.0021) C57_$2 3.5146 (0.0017) N61_$2 3.4415 (0.0017) C62_$2 3.3232 (0.0020) C63_$2 3.2559 (0.0024) C64_$2 3.3189 (0.0026) C65_$2 3.4577 (0.0024) C66_$2 3.2833 (0.0023) C67_$2 Rms deviation of fitted atoms = 0.0106 7.0177 (0.0014) x + 0.6706 (0.0039) y + 3.4781 (0.0057) z = 11.8888 (0.0026) Angle to previous plane (with approximate e.s.d.) = 3.08 (4) * -0.0094 (0.0013) N51_$2 * 0.0260 (0.0014) C52_$2 * 0.0365 (0.0015) C53_$2 * 0.0183 (0.0017) C54_$2 * -0.0382 (0.0018) C55_$2 * -0.0528 (0.0016) C56_$2 * 0.0307 (0.0015) C57_$2 * 0.0547 (0.0014) N61_$2 * 0.0269 (0.0014) C62_$2 * -0.0163 (0.0015) C63_$2 * -0.0556 (0.0017) C64_$2 * -0.0369 (0.0019) C65_$2 * 0.0282 (0.0017) C66_$2 * -0.0120 (0.0016) C67_$2 Rms deviation of fitted atoms = 0.0348 6.8795 (0.0026) x + 0.6269 (0.0093) y + 4.0923 (0.0095) z = 8.7025 (0.0043) Angle to previous plane (with approximate e.s.d.) = 2.55 (6) * 0.0027 (0.0011) N31 * 0.0007 (0.0010) C32 * -0.0041 (0.0011) C33 * 0.0044 (0.0013) C34 * -0.0011 (0.0013) C35 * -0.0026 (0.0013) C36 - 0.0106 (0.0025) C37 3.5069 (0.0021) N51_$2 3.4822 (0.0020) C52_$2 3.4585 (0.0026) C53_$2 3.4707 (0.0034) C54_$2 3.3898 (0.0030) C57_$2 3.5151 (0.0017) N61_$2 3.4533 (0.0018) C62_$2 3.3476 (0.0024) C63_$2 3.2810 (0.0030) C64_$2 3.3192 (0.0030) C67_$2 Rms deviation of fitted atoms = 0.0029 6.8271 (0.0024) x + 0.4814 (0.0086) y + 4.4012 (0.0091) z = 8.8110 (0.0041) Angle to previous plane (with approximate e.s.d.) = 1.24 (8) * -0.0059 (0.0010) N41 * 0.0008 (0.0010) C42 * 0.0053 (0.0011) C43 * -0.0066 (0.0012) C44 * 0.0016 (0.0012) C45 * 0.0049 (0.0012) C46 0.0304 (0.0025) C47 3.5316 (0.0022) N51_$2 3.4808 (0.0021) C52_$2 3.4309 (0.0019) C53_$2 3.4449 (0.0021) C54_$2 3.3354 (0.0025) C57_$2 3.5381 (0.0033) N61_$2 3.4508 (0.0028) C62_$2 3.3181 (0.0032) C63_$2 3.2514 (0.0040) C64_$2 3.2638 (0.0031) C67_$2 Rms deviation of fitted atoms = 0.0047 6.8795 (0.0026) x + 0.6269 (0.0093) y + 4.0923 (0.0095) z = 8.7025 (0.0043) Angle to previous plane (with approximate e.s.d.) = 1.24 (8) * 0.0027 (0.0011) N31 * 0.0007 (0.0010) C32 * -0.0041 (0.0011) C33 * 0.0044 (0.0013) C34 * -0.0011 (0.0013) C35 * -0.0026 (0.0013) C36 - 0.0106 (0.0025) C37 - 3.3726 (0.0040) N51_$1 - 3.3972 (0.0034) C52_$1 - 3.4210 (0.0037) C53_$1 - 3.4088 (0.0047) C54_$1 - 3.4897 (0.0035) C57_$1 - 3.3644 (0.0026) N61_$1 - 3.4262 (0.0026) C62_$1 - 3.5319 (0.0022) C63_$1 - 3.5985 (0.0022) C64_$1 - 3.5603 (0.0028) C67_$1 Rms deviation of fitted atoms = 0.0029 6.8271 (0.0024) x + 0.4814 (0.0086) y + 4.4012 (0.0091) z = 8.8110 (0.0041) Angle to previous plane (with approximate e.s.d.) = 1.24 (8) * -0.0059 (0.0010) N41 * 0.0008 (0.0010) C42 * 0.0053 (0.0011) C43 * -0.0066 (0.0012) C44 * 0.0016 (0.0012) C45 * 0.0049 (0.0012) C46 0.0304 (0.0025) C47 - 3.2955 (0.0032) N51_$1 - 3.3463 (0.0026) C52_$1 - 3.3962 (0.0023) C53_$1 - 3.3822 (0.0029) C54_$1 - 3.4917 (0.0020) C57_$1 - 3.2890 (0.0033) N61_$1 - 3.3763 (0.0026) C62_$1 - 3.5090 (0.0023) C63_$1 - 3.5758 (0.0030) C64_$1 - 3.5633 (0.0021) C67_$1 Rms deviation of fitted atoms = 0.0047 6.8795 (0.0026) x + 0.6269 (0.0093) y + 4.0923 (0.0095) z = 8.7025 (0.0043) Angle to previous plane (with approximate e.s.d.) = 1.24 (8) * 0.0027 (0.0011) N31 * 0.0007 (0.0010) C32 * -0.0041 (0.0011) C33 * 0.0044 (0.0013) C34 * -0.0011 (0.0013) C35 * -0.0026 (0.0013) C36 - 0.0106 (0.0025) C37 3.5069 (0.0021) N51_$2 3.4822 (0.0020) C52_$2 3.4585 (0.0026) C53_$2 3.4707 (0.0034) C54_$2 3.3898 (0.0030) C57_$2 3.5151 (0.0017) N61_$2 3.4533 (0.0018) C62_$2 3.3476 (0.0024) C63_$2 3.2810 (0.0030) C64_$2 3.3192 (0.0030) C67_$2 Rms deviation of fitted atoms = 0.0029 6.8271 (0.0024) x + 0.4814 (0.0086) y + 4.4012 (0.0091) z = 8.8110 (0.0041) Angle to previous plane (with approximate e.s.d.) = 1.24 (8) * -0.0059 (0.0010) N41 * 0.0008 (0.0010) C42 * 0.0053 (0.0011) C43 * -0.0066 (0.0012) C44 * 0.0016 (0.0012) C45 * 0.0049 (0.0012) C46 0.0304 (0.0025) C47 3.5316 (0.0022) N51_$2 3.4808 (0.0021) C52_$2 3.4309 (0.0019) C53_$2 3.4449 (0.0021) C54_$2 3.3354 (0.0025) C57_$2 3.5381 (0.0033) N61_$2 3.4508 (0.0028) C62_$2 3.3181 (0.0032) C63_$2 3.2514 (0.0040) C64_$2 3.2638 (0.0031) C67_$2 Rms deviation of fitted atoms = 0.0047 6.8271 (0.0024) x + 0.4814 (0.0086) y + 4.4012 (0.0091) z = 8.8110 (0.0041) Angle to previous plane (with approximate e.s.d.) = 0.0 * -0.0059 (0.0010) N41 * 0.0008 (0.0010) C42 * 0.0053 (0.0011) C43 * -0.0066 (0.0012) C44 * 0.0016 (0.0012) C45 * 0.0049 (0.0012) C46 0.0304 (0.0025) C47 Rms deviation of fitted atoms = 0.0047 6.9040 (0.0027) x + 0.7551 (0.0092) y + 3.8962 (0.0103) z = 1.3218 (0.0056) Angle to previous plane (with approximate e.s.d.) = 2.06 (8) * 0.0077 (0.0011) N51 * -0.0017 (0.0011) C52 * -0.0063 (0.0011) C53 * 0.0087 (0.0014) C54 * -0.0029 (0.0015) C55 * -0.0056 (0.0014) C56 - 0.0596 (0.0027) C57 Rms deviation of fitted atoms = 0.0060 7.1357 (0.0024) x + 0.6236 (0.0102) y + 2.9632 (0.0108) z = 1.5987 (0.0052) Angle to previous plane (with approximate e.s.d.) = 4.22 (8) * -0.0006 (0.0012) N61 * -0.0055 (0.0011) C62 * 0.0062 (0.0012) C63 * -0.0013 (0.0014) C64 * -0.0046 (0.0016) C65 * 0.0057 (0.0015) C66 0.0314 (0.0028) C67 Rms deviation of fitted atoms = 0.0045 |
x | y | z | Uiso*/Ueq | ||
S1 | 0.36375 (7) | 0.03072 (4) | 0.13013 (4) | 0.07258 (19) | |
O14 | 0.99514 (15) | 0.22322 (11) | 0.41741 (8) | 0.0663 (4) | |
O24 | 0.08412 (17) | 0.30651 (13) | −0.06518 (10) | 0.0772 (4) | |
C11 | 0.5529 (2) | 0.10110 (13) | 0.21361 (12) | 0.0538 (4) | |
C12 | 0.5377 (2) | 0.16396 (15) | 0.30720 (12) | 0.0591 (5) | |
C13 | 0.6831 (2) | 0.20743 (15) | 0.37570 (12) | 0.0575 (4) | |
C14 | 0.8485 (2) | 0.18691 (14) | 0.35218 (11) | 0.0515 (4) | |
C15 | 0.8649 (2) | 0.12613 (15) | 0.25832 (12) | 0.0618 (5) | |
C16 | 0.7188 (3) | 0.08397 (15) | 0.18996 (12) | 0.0620 (5) | |
C21 | 0.2941 (2) | 0.12155 (13) | 0.07634 (10) | 0.0483 (4) | |
C22 | 0.1162 (2) | 0.12248 (14) | 0.06042 (11) | 0.0549 (4) | |
C23 | 0.0488 (2) | 0.18181 (15) | 0.01042 (12) | 0.0575 (5) | |
C24 | 0.1594 (2) | 0.24503 (14) | −0.02205 (11) | 0.0531 (4) | |
C25 | 0.3385 (2) | 0.24510 (14) | −0.00630 (12) | 0.0551 (4) | |
C26 | 0.4046 (2) | 0.18255 (14) | 0.04110 (12) | 0.0536 (4) | |
N31 | 0.89380 (18) | 0.22912 (11) | 0.58957 (10) | 0.0525 (4) | |
C32 | 0.84012 (19) | 0.30006 (13) | 0.66846 (11) | 0.0449 (4) | |
C33 | 0.7962 (2) | 0.27033 (14) | 0.74569 (12) | 0.0521 (4) | |
C34 | 0.8110 (3) | 0.16413 (16) | 0.73920 (15) | 0.0684 (5) | |
C35 | 0.8638 (3) | 0.09403 (16) | 0.65972 (16) | 0.0727 (6) | |
C36 | 0.9037 (2) | 0.13053 (15) | 0.58673 (14) | 0.0647 (5) | |
C37 | 0.7403 (2) | 0.34799 (16) | 0.82617 (12) | 0.0598 (5) | |
N41 | 0.87423 (17) | 0.43519 (11) | 0.59691 (9) | 0.0510 (3) | |
C42 | 0.82876 (19) | 0.40831 (13) | 0.67189 (10) | 0.0437 (4) | |
C43 | 0.77184 (19) | 0.48229 (13) | 0.75312 (11) | 0.0480 (4) | |
C44 | 0.7622 (2) | 0.58675 (14) | 0.75393 (13) | 0.0578 (5) | |
C45 | 0.8095 (2) | 0.61360 (15) | 0.67954 (14) | 0.0618 (5) | |
C46 | 0.8647 (2) | 0.53572 (15) | 0.60317 (13) | 0.0576 (4) | |
C47 | 0.7284 (2) | 0.44886 (16) | 0.82991 (12) | 0.0582 (5) | |
N51 | 0.23204 (19) | 0.43628 (13) | −0.15447 (10) | 0.0608 (4) | |
C52 | 0.2832 (2) | 0.41071 (13) | −0.24258 (12) | 0.0487 (4) | |
C53 | 0.3006 (2) | 0.48535 (14) | −0.28915 (13) | 0.0558 (4) | |
C54 | 0.2639 (3) | 0.58927 (17) | −0.2404 (2) | 0.0781 (6) | |
C55 | 0.2102 (3) | 0.61362 (18) | −0.1529 (2) | 0.0868 (7) | |
C56 | 0.1955 (3) | 0.53514 (19) | −0.11229 (16) | 0.0777 (6) | |
C57 | 0.3494 (2) | 0.45268 (18) | −0.38288 (15) | 0.0684 (5) | |
N61 | 0.3047 (2) | 0.23299 (13) | −0.24347 (12) | 0.0657 (4) | |
C62 | 0.3178 (2) | 0.30195 (14) | −0.29116 (12) | 0.0504 (4) | |
C63 | 0.3610 (2) | 0.27259 (15) | −0.38517 (13) | 0.0579 (5) | |
C64 | 0.3883 (3) | 0.16648 (19) | −0.43103 (17) | 0.0796 (6) | |
C65 | 0.3748 (3) | 0.09661 (19) | −0.3850 (2) | 0.0900 (7) | |
C66 | 0.3342 (3) | 0.13232 (18) | −0.2912 (2) | 0.0868 (7) | |
C67 | 0.3761 (2) | 0.35096 (19) | −0.42946 (14) | 0.0698 (5) | |
H14 | 0.9676 | 0.2467 | 0.4717 | 0.099* | |
H24 | 0.1575 | 0.3326 | −0.0901 | 0.116* | |
H12 | 0.4272 | 0.1771 | 0.3242 | 0.071* | |
H13 | 0.6703 | 0.2507 | 0.4380 | 0.069* | |
H15 | 0.9754 | 0.1135 | 0.2411 | 0.074* | |
H16 | 0.7320 | 0.0434 | 0.1270 | 0.074* | |
H22 | 0.0402 | 0.0822 | 0.0839 | 0.066* | |
H23 | −0.0720 | 0.1792 | −0.0015 | 0.069* | |
H25 | 0.4146 | 0.2875 | −0.0278 | 0.066* | |
H26 | 0.5249 | 0.1814 | 0.0495 | 0.064* | |
H34 | 0.7846 | 0.1418 | 0.7893 | 0.082* | |
H35 | 0.8731 | 0.0234 | 0.6543 | 0.087* | |
H36 | 0.9396 | 0.0821 | 0.5325 | 0.078* | |
H37 | 0.7114 | 0.3284 | 0.8773 | 0.072* | |
H44 | 0.7234 | 0.6376 | 0.8055 | 0.069* | |
H45 | 0.8050 | 0.6829 | 0.6797 | 0.074* | |
H46 | 0.8974 | 0.5555 | 0.5527 | 0.069* | |
H47 | 0.6912 | 0.4977 | 0.8834 | 0.070* | |
H54 | 0.2764 | 0.6415 | −0.2681 | 0.094* | |
H55 | 0.1834 | 0.6822 | −0.1203 | 0.104* | |
H56 | 0.1579 | 0.5529 | −0.0521 | 0.093* | |
H57 | 0.3631 | 0.5029 | −0.4127 | 0.082* | |
H64 | 0.4158 | 0.1439 | −0.4935 | 0.095* | |
H65 | 0.3924 | 0.0254 | −0.4153 | 0.108* | |
H66 | 0.3272 | 0.0833 | −0.2600 | 0.104* | |
H67 | 0.4049 | 0.3313 | −0.4916 | 0.084* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0902 (4) | 0.0529 (3) | 0.0697 (3) | −0.0112 (2) | −0.0169 (3) | 0.0289 (2) |
O14 | 0.0625 (8) | 0.0841 (9) | 0.0474 (7) | 0.0028 (7) | 0.0056 (6) | 0.0203 (7) |
O24 | 0.0680 (8) | 0.1062 (11) | 0.0761 (9) | 0.0238 (8) | 0.0078 (7) | 0.0536 (8) |
C11 | 0.0704 (11) | 0.0466 (10) | 0.0471 (9) | 0.0026 (8) | 0.0007 (8) | 0.0236 (8) |
C12 | 0.0641 (11) | 0.0640 (12) | 0.0545 (11) | 0.0191 (9) | 0.0082 (9) | 0.0253 (9) |
C13 | 0.0704 (12) | 0.0613 (11) | 0.0405 (9) | 0.0175 (9) | 0.0081 (8) | 0.0156 (8) |
C14 | 0.0602 (10) | 0.0551 (10) | 0.0438 (9) | 0.0034 (8) | 0.0071 (8) | 0.0250 (8) |
C15 | 0.0639 (11) | 0.0757 (13) | 0.0461 (10) | 0.0062 (9) | 0.0163 (8) | 0.0215 (9) |
C16 | 0.0816 (13) | 0.0619 (12) | 0.0400 (9) | 0.0045 (10) | 0.0129 (9) | 0.0161 (8) |
C21 | 0.0597 (10) | 0.0439 (9) | 0.0334 (8) | −0.0011 (7) | 0.0026 (7) | 0.0078 (7) |
C22 | 0.0598 (11) | 0.0570 (11) | 0.0417 (9) | −0.0046 (8) | 0.0136 (8) | 0.0122 (8) |
C23 | 0.0460 (9) | 0.0733 (12) | 0.0471 (10) | 0.0057 (9) | 0.0086 (8) | 0.0146 (9) |
C24 | 0.0555 (10) | 0.0642 (11) | 0.0381 (8) | 0.0109 (8) | 0.0053 (7) | 0.0162 (8) |
C25 | 0.0521 (10) | 0.0656 (11) | 0.0522 (10) | 0.0029 (8) | 0.0101 (8) | 0.0279 (9) |
C26 | 0.0478 (9) | 0.0601 (11) | 0.0513 (10) | 0.0043 (8) | 0.0035 (7) | 0.0201 (8) |
N31 | 0.0577 (8) | 0.0472 (9) | 0.0487 (8) | 0.0141 (7) | 0.0004 (6) | 0.0125 (7) |
C32 | 0.0398 (8) | 0.0505 (10) | 0.0393 (8) | 0.0039 (7) | −0.0054 (6) | 0.0133 (7) |
C33 | 0.0485 (9) | 0.0584 (11) | 0.0474 (9) | 0.0002 (8) | −0.0060 (7) | 0.0219 (8) |
C34 | 0.0718 (12) | 0.0699 (13) | 0.0692 (13) | −0.0017 (10) | −0.0071 (10) | 0.0394 (11) |
C35 | 0.0819 (14) | 0.0515 (12) | 0.0836 (15) | 0.0099 (10) | −0.0077 (11) | 0.0278 (11) |
C36 | 0.0710 (12) | 0.0535 (12) | 0.0652 (12) | 0.0153 (9) | −0.0011 (9) | 0.0169 (9) |
C37 | 0.0597 (11) | 0.0762 (13) | 0.0429 (9) | −0.0017 (9) | 0.0025 (8) | 0.0249 (9) |
N41 | 0.0569 (8) | 0.0538 (9) | 0.0434 (8) | 0.0110 (7) | 0.0040 (6) | 0.0190 (6) |
C42 | 0.0389 (8) | 0.0513 (9) | 0.0369 (8) | 0.0054 (7) | −0.0031 (6) | 0.0133 (7) |
C43 | 0.0418 (9) | 0.0525 (10) | 0.0407 (9) | 0.0044 (7) | −0.0016 (7) | 0.0084 (7) |
C44 | 0.0550 (10) | 0.0500 (11) | 0.0567 (11) | 0.0099 (8) | 0.0042 (8) | 0.0054 (8) |
C45 | 0.0643 (11) | 0.0503 (11) | 0.0693 (12) | 0.0109 (9) | 0.0039 (9) | 0.0204 (10) |
C46 | 0.0636 (11) | 0.0593 (12) | 0.0544 (10) | 0.0104 (9) | 0.0037 (8) | 0.0268 (9) |
C47 | 0.0544 (10) | 0.0727 (13) | 0.0392 (9) | 0.0061 (9) | 0.0053 (7) | 0.0113 (8) |
N51 | 0.0583 (9) | 0.0650 (10) | 0.0517 (9) | 0.0088 (7) | 0.0004 (7) | 0.0141 (8) |
C52 | 0.0404 (9) | 0.0520 (10) | 0.0510 (10) | 0.0043 (7) | −0.0051 (7) | 0.0185 (8) |
C53 | 0.0443 (9) | 0.0531 (11) | 0.0714 (12) | 0.0042 (8) | −0.0051 (8) | 0.0283 (9) |
C54 | 0.0597 (12) | 0.0585 (13) | 0.1169 (19) | 0.0059 (10) | −0.0052 (12) | 0.0377 (13) |
C55 | 0.0708 (14) | 0.0538 (13) | 0.115 (2) | 0.0098 (10) | 0.0047 (13) | 0.0069 (14) |
C56 | 0.0671 (13) | 0.0764 (15) | 0.0657 (13) | 0.0090 (11) | 0.0017 (10) | −0.0015 (12) |
C57 | 0.0601 (12) | 0.0847 (15) | 0.0745 (13) | 0.0052 (10) | 0.0011 (10) | 0.0494 (12) |
N61 | 0.0647 (10) | 0.0595 (10) | 0.0823 (11) | 0.0081 (8) | 0.0040 (8) | 0.0390 (9) |
C62 | 0.0413 (9) | 0.0531 (10) | 0.0569 (10) | 0.0034 (7) | −0.0039 (7) | 0.0236 (8) |
C63 | 0.0447 (9) | 0.0633 (12) | 0.0578 (11) | 0.0082 (8) | 0.0005 (8) | 0.0136 (9) |
C64 | 0.0660 (13) | 0.0735 (15) | 0.0818 (15) | 0.0112 (11) | 0.0078 (11) | 0.0071 (12) |
C65 | 0.0713 (14) | 0.0582 (14) | 0.120 (2) | 0.0146 (11) | 0.0092 (14) | 0.0075 (14) |
C66 | 0.0745 (14) | 0.0609 (14) | 0.136 (2) | 0.0083 (11) | 0.0023 (14) | 0.0531 (15) |
C67 | 0.0608 (12) | 0.0975 (17) | 0.0549 (11) | 0.0085 (11) | 0.0070 (9) | 0.0332 (12) |
O14—C14 | 1.353 (2) | C37—C47 | 1.342 (3) |
S1—C11 | 1.7751 (18) | N41—C42 | 1.358 (2) |
O24—C24 | 1.354 (2) | N41—C46 | 1.324 (2) |
S1—C21 | 1.7760 (17) | C42—C43 | 1.413 (2) |
C11—C12 | 1.382 (2) | C43—C44 | 1.401 (2) |
C11—C16 | 1.382 (3) | C43—C47 | 1.427 (2) |
C12—C13 | 1.376 (2) | C44—C45 | 1.353 (3) |
C13—C14 | 1.387 (2) | C45—C46 | 1.386 (2) |
C14—C15 | 1.381 (2) | N51—C52 | 1.350 (2) |
C15—C16 | 1.378 (2) | N51—C56 | 1.322 (3) |
C21—C22 | 1.377 (2) | C52—C53 | 1.406 (2) |
C21—C26 | 1.383 (2) | C52—C62 | 1.445 (2) |
C22—C23 | 1.375 (2) | C53—C54 | 1.396 (3) |
C23—C24 | 1.377 (2) | C53—C57 | 1.416 (3) |
C24—C25 | 1.384 (2) | C54—C55 | 1.352 (3) |
C25—C26 | 1.379 (2) | C55—C56 | 1.385 (3) |
N31—C32 | 1.361 (2) | C57—C67 | 1.340 (3) |
N31—C36 | 1.314 (2) | N61—C62 | 1.351 (2) |
C32—C33 | 1.406 (2) | N61—C66 | 1.339 (3) |
C32—C42 | 1.441 (2) | C62—C63 | 1.405 (2) |
C33—C34 | 1.405 (3) | C63—C64 | 1.390 (3) |
C33—C37 | 1.424 (2) | C63—C67 | 1.424 (3) |
C34—C35 | 1.359 (3) | C64—C65 | 1.342 (3) |
C35—C36 | 1.390 (3) | C65—C66 | 1.394 (3) |
C11—S1—C21 | 106.28 (8) | N41—C42—C32 | 118.52 (14) |
O14—C14—C13 | 122.87 (15) | N41—C42—C43 | 122.63 (15) |
O14—C14—C15 | 118.34 (16) | C32—C42—C43 | 118.85 (14) |
O24—C24—C23 | 116.95 (15) | C42—C43—C44 | 117.27 (16) |
O24—C24—C25 | 124.04 (16) | C42—C43—C47 | 119.60 (16) |
S1—C11—C12 | 120.75 (15) | C44—C43—C47 | 123.12 (16) |
S1—C11—C16 | 120.57 (14) | C43—C44—C45 | 119.93 (17) |
C16—C11—C12 | 118.22 (16) | C44—C45—C46 | 118.68 (17) |
C11—C12—C13 | 121.21 (17) | N41—C46—C45 | 124.61 (17) |
C12—C13—C14 | 120.21 (16) | C37—C47—C43 | 121.04 (16) |
C13—C14—C15 | 118.78 (16) | C52—N51—C56 | 117.74 (17) |
C14—C15—C16 | 120.57 (17) | N51—C52—C53 | 122.40 (16) |
C11—C16—C15 | 120.95 (16) | N51—C52—C62 | 118.49 (15) |
S1—C21—C22 | 117.08 (12) | C53—C52—C62 | 119.10 (16) |
S1—C21—C26 | 124.31 (14) | C52—C53—C54 | 117.43 (19) |
C22—C21—C26 | 118.27 (15) | C52—C53—C57 | 119.76 (17) |
C21—C22—C23 | 121.27 (15) | C54—C53—C57 | 122.80 (19) |
C22—C23—C24 | 120.32 (16) | C53—C54—C55 | 119.7 (2) |
C23—C24—C25 | 118.98 (16) | C54—C55—C56 | 119.2 (2) |
C24—C25—C26 | 120.29 (16) | N51—C56—C55 | 123.5 (2) |
C21—C26—C25 | 120.80 (16) | C53—C57—C67 | 121.36 (18) |
C32—N31—C36 | 118.18 (15) | C62—N61—C66 | 116.15 (18) |
N31—C32—C33 | 121.79 (15) | N61—C62—C52 | 117.69 (16) |
N31—C32—C42 | 118.42 (14) | N61—C62—C63 | 123.30 (17) |
C33—C32—C42 | 119.79 (15) | C52—C62—C63 | 119.01 (15) |
C32—C33—C34 | 117.57 (17) | C62—C63—C64 | 117.61 (19) |
C32—C33—C37 | 119.24 (16) | C62—C63—C67 | 119.73 (17) |
C34—C33—C37 | 123.19 (17) | C64—C63—C67 | 122.7 (2) |
C33—C34—C35 | 119.96 (18) | C63—C64—C65 | 119.9 (2) |
C34—C35—C36 | 118.41 (18) | C64—C65—C66 | 119.1 (2) |
N31—C36—C35 | 124.08 (19) | N61—C66—C65 | 123.9 (2) |
C33—C37—C47 | 121.48 (16) | C57—C67—C63 | 120.99 (18) |
C42—N41—C46 | 116.86 (14) | ||
C11—S1—C21—C22 | −139.81 (13) | N41—C42—C43—C44 | 0.4 (2) |
C11—S1—C21—C26 | 46.95 (16) | C32—C42—C43—C44 | −179.93 (13) |
C21—S1—C11—C12 | 88.13 (15) | N41—C42—C43—C47 | −179.16 (14) |
C21—S1—C11—C16 | −99.74 (15) | C32—C42—C43—C47 | 0.5 (2) |
C16—C11—C12—C13 | −0.9 (3) | C42—C43—C44—C45 | −1.1 (2) |
S1—C11—C12—C13 | 171.46 (13) | C47—C43—C44—C45 | 178.43 (16) |
C11—C12—C13—C14 | −1.3 (3) | C43—C44—C45—C46 | 0.8 (3) |
C12—C13—C14—O14 | −176.86 (15) | C42—N41—C46—C45 | −1.0 (2) |
C12—C13—C14—C15 | 2.6 (3) | C44—C45—C46—N41 | 0.3 (3) |
O14—C14—C15—C16 | 177.62 (16) | C33—C37—C47—C43 | −0.1 (3) |
C13—C14—C15—C16 | −1.9 (3) | C44—C43—C47—C37 | −179.71 (16) |
C14—C15—C16—C11 | −0.2 (3) | C42—C43—C47—C37 | −0.2 (2) |
C12—C11—C16—C15 | 1.6 (3) | C56—N51—C52—C53 | 0.9 (2) |
S1—C11—C16—C15 | −170.73 (14) | C56—N51—C52—C62 | −177.89 (15) |
C26—C21—C22—C23 | 0.3 (2) | N51—C52—C53—C54 | 0.4 (2) |
S1—C21—C22—C23 | −173.31 (13) | C62—C52—C53—C54 | 179.21 (15) |
C21—C22—C23—C24 | −2.3 (3) | N51—C52—C53—C57 | −177.97 (15) |
C22—C23—C24—O24 | −175.82 (16) | C62—C52—C53—C57 | 0.8 (2) |
C22—C23—C24—C25 | 2.1 (2) | C52—C53—C54—C55 | −1.5 (3) |
O24—C24—C25—C26 | 177.83 (17) | C57—C53—C54—C55 | 176.91 (18) |
C23—C24—C25—C26 | 0.1 (3) | C53—C54—C55—C56 | 1.1 (3) |
C24—C25—C26—C21 | −2.1 (3) | C52—N51—C56—C55 | −1.3 (3) |
C22—C21—C26—C25 | 1.8 (2) | C54—C55—C56—N51 | 0.3 (3) |
S1—C21—C26—C25 | 175.01 (13) | C54—C53—C57—C67 | −176.96 (17) |
C36—N31—C32—C33 | 0.1 (2) | C52—C53—C57—C67 | 1.4 (3) |
C36—N31—C32—C42 | −179.91 (14) | C66—N61—C62—C63 | −0.5 (2) |
N31—C32—C33—C34 | 0.5 (2) | C66—N61—C62—C52 | 178.73 (16) |
C42—C32—C33—C34 | −179.45 (14) | N51—C52—C62—N61 | −3.0 (2) |
N31—C32—C33—C37 | −179.79 (14) | C53—C52—C62—N61 | 178.18 (14) |
C42—C32—C33—C37 | 0.3 (2) | N51—C52—C62—C63 | 176.27 (14) |
C32—C33—C34—C35 | −0.9 (3) | C53—C52—C62—C63 | −2.5 (2) |
C37—C33—C34—C35 | 179.45 (16) | N61—C62—C63—C64 | 1.2 (2) |
C33—C34—C35—C36 | 0.6 (3) | C52—C62—C63—C64 | −178.07 (15) |
C32—N31—C36—C35 | −0.4 (3) | N61—C62—C63—C67 | −178.54 (15) |
C34—C35—C36—N31 | 0.1 (3) | C52—C62—C63—C67 | 2.2 (2) |
C34—C33—C37—C47 | 179.77 (17) | C62—C63—C64—C65 | −0.7 (3) |
C32—C33—C37—C47 | 0.1 (2) | C67—C63—C64—C65 | 178.98 (19) |
C46—N41—C42—C43 | 0.6 (2) | C63—C64—C65—C66 | −0.3 (3) |
C46—N41—C42—C32 | −179.02 (14) | C62—N61—C66—C65 | −0.6 (3) |
N31—C32—C42—N41 | −0.8 (2) | C64—C65—C66—N61 | 1.0 (3) |
C33—C32—C42—N41 | 179.13 (13) | C53—C57—C67—C63 | −1.7 (3) |
N31—C32—C42—C43 | 179.50 (13) | C64—C63—C67—C57 | −179.78 (18) |
C33—C32—C42—C43 | −0.5 (2) | C62—C63—C67—C57 | −0.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O14—H14···N31 | 0.82 | 1.99 | 2.741 (2) | 153 |
O24—H24···N51 | 0.82 | 2.01 | 2.757 (2) | 151 |
2(C12H10O4S)·3(C12H8N2) | ? #Insert any comments here. |
Mr = 1041.13 | Dx = 1.398 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.7107 Å |
a = 15.8692 (16) Å | Cell parameters from 25 reflections |
b = 24.3728 (17) Å | θ = 10.2–18.3° |
c = 13.0952 (9) Å | µ = 0.18 mm−1 |
β = 102.362 (8)° | T = 294 K |
V = 4947.5 (7) Å3 | Plate, colorless |
Z = 4 | 0.42 × 0.38 × 0.10 mm |
F(000) = 2168 |
Enraf-Nonius CAD-4 diffractometer | 3182 reflections with I > 2σ(I) |
Radiation source: X-ray tube | Rint = 0.006 |
Graphite monochromator | θmax = 25.1°, θmin = 2.0° |
θ/2θ scans | h = −18→18 |
Absorption correction: gaussian ABSORB in NRCVAX (Gabe et al., 1989) | k = 0→29 |
Tmin = 0.937, Tmax = 0.983 | l = 0→15 |
4636 measured reflections | 3 standard reflections every 120 min |
4434 independent reflections | intensity decay: 1.7% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.104 | Calculated w = 1/[σ2(Fo2) + (0.0534P)2 + 1.3074P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
4434 reflections | Δρmax = 0.22 e Å−3 |
346 parameters | Δρmin = −0.30 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00124 (18) |
2(C12H10O4S)·3(C12H8N2) | V = 4947.5 (7) Å3 |
Mr = 1041.13 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 15.8692 (16) Å | µ = 0.18 mm−1 |
b = 24.3728 (17) Å | T = 294 K |
c = 13.0952 (9) Å | 0.42 × 0.38 × 0.10 mm |
β = 102.362 (8)° |
Enraf-Nonius CAD-4 diffractometer | 3182 reflections with I > 2σ(I) |
Absorption correction: gaussian ABSORB in NRCVAX (Gabe et al., 1989) | Rint = 0.006 |
Tmin = 0.937, Tmax = 0.983 | 3 standard reflections every 120 min |
4636 measured reflections | intensity decay: 1.7% |
4434 independent reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.22 e Å−3 |
4434 reflections | Δρmin = −0.30 e Å−3 |
346 parameters |
Experimental. ? #Insert any special details here. |
Geometry. Mean-plane data ex SHELXL refinement cycles. Equivalent position denoted by "$1" is at 1 - x, y, 0.5 - z Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 4.2301 (0.0181) x + 22.4954 (0.0088) y + 4.2984 (0.0152) z = 10.6931 (0.0078) * 0.0000 (0.0000) S1 * 0.0000 (0.0000) O11 * 0.0000 (0.0000) O12 Rms deviation of fitted atoms = 0.0000 0.7156 (0.0116) x + 5.2728 (0.0130) y + 12.3489 (0.0041) z = 3.9077 (0.0092) Angle to previous plane (with approximate e.s.d.) = 62.72 (8) * 0.0453 (0.0016) C11 * 0.0550 (0.0015) C12 * 0.0347 (0.0015) C13 * -0.0222 (0.0018) C14 * 0.0281 (0.0016) C15 * 0.0640 (0.0016) C16 * -0.1180 (0.0009) S1 * -0.0868 (0.0012) O14 Rms deviation of fitted atoms = 0.0643 - 4.2301 (0.0181) x + 22.4954 (0.0088) y + 4.2984 (0.0152) z = 10.6931 (0.0078) Angle to previous plane (with approximate e.s.d.) = 62.72 (8) * 0.0000 (0.0000) S1 * 0.0000 (0.0000) O11 * 0.0000 (0.0000) O12 Rms deviation of fitted atoms = 0.0000 - 14.2444 (0.0068) x + 9.2758 (0.0154) y - 0.3281 (0.0100) z = 0.4586 (0.0098) Angle to previous plane (with approximate e.s.d.) = 58.08 (8) * -0.0213 (0.0016) C21 * -0.0261 (0.0017) C22 * -0.0086 (0.0019) C23 * 0.0110 (0.0020) C24 * -0.0029 (0.0017) C25 * -0.0291 (0.0016) C26 * 0.0485 (0.0011) S1 * 0.0284 (0.0016) O24 Rms deviation of fitted atoms = 0.0258 12.4411 (0.0099) x - 1.7307 (0.0224) y - 10.0866 (0.0085) z = 3.4231 (0.0064) Angle to previous plane (with approximate e.s.d.) = 53.59 (6) * 0.0011 (0.0015) N31 * -0.0177 (0.0015) C32 * 0.0170 (0.0015) C33 * -0.0008 (0.0017) C34 * -0.0155 (0.0018) C35 * 0.0160 (0.0018) C36 0.1085 (0.0039) C37 - 0.0419 (0.0043) C32_$1 0.1811 (0.0045) C37_$1 Rms deviation of fitted atoms = 0.0135 12.4411 (0.0099) x + 1.7307 (0.0224) y - 10.0866 (0.0085) z = 3.9747 (0.0100) Angle to previous plane (with approximate e.s.d.) = 8.14 (12) * -0.0011 (0.0015) N31_$1 * 0.0177 (0.0015) C32_$1 * -0.0170 (0.0015) C33_$1 * 0.0008 (0.0017) C34_$1 * 0.0155 (0.0018) C35_$1 * -0.0160 (0.0018) C36_$1 - 0.1085 (0.0039) C37_$1 Rms deviation of fitted atoms = 0.0135 11.5438 (0.0114) x + 0.0924 (0.0234) y - 10.8165 (0.0078) z = 1.4284 (0.0215) Angle to previous plane (with approximate e.s.d.) = 6.42 (13) * 0.0016 (0.0017) N41 * 0.0078 (0.0015) C42 * -0.0124 (0.0015) C43 * 0.0084 (0.0017) C44 * 0.0008 (0.0019) C45 * -0.0062 (0.0019) C46 - 0.0592 (0.0037) C47 Rms deviation of fitted atoms = 0.0074 11.9984 (0.0105) x + 1.0322 (0.0246) y - 10.4739 (0.0079) z = 2.5886 (0.0216) Angle to previous plane (with approximate e.s.d.) = 3.34 (13) * 0.0030 (0.0017) N51 * -0.0084 (0.0016) C52 * 0.0066 (0.0016) C53 * 0.0000 (0.0018) C54 * -0.0051 (0.0020) C55 * 0.0038 (0.0020) C56 0.0139 (0.0038) C57 Rms deviation of fitted atoms = 0.0052 |
x | y | z | Uiso*/Ueq | ||
S1 | 0.30076 (3) | 0.51893 (2) | 0.06788 (4) | 0.03971 (16) | |
O11 | 0.21571 (9) | 0.50137 (6) | 0.07611 (13) | 0.0542 (4) | |
O12 | 0.31144 (10) | 0.53995 (6) | −0.03161 (11) | 0.0537 (4) | |
O14 | 0.52449 (9) | 0.32527 (6) | 0.14013 (13) | 0.0519 (4) | |
O24 | 0.40470 (15) | 0.68772 (7) | 0.38834 (14) | 0.0788 (6) | |
C11 | 0.36983 (12) | 0.46251 (7) | 0.10120 (15) | 0.0348 (4) | |
C12 | 0.33602 (13) | 0.41287 (8) | 0.12514 (15) | 0.0366 (5) | |
C13 | 0.38733 (13) | 0.36666 (8) | 0.14025 (16) | 0.0410 (5) | |
C14 | 0.47214 (13) | 0.36959 (8) | 0.12947 (16) | 0.0400 (5) | |
C15 | 0.50681 (14) | 0.41987 (8) | 0.11007 (17) | 0.0438 (5) | |
C16 | 0.45568 (14) | 0.46615 (8) | 0.09618 (16) | 0.0419 (5) | |
C21 | 0.33627 (12) | 0.56929 (7) | 0.16260 (16) | 0.0373 (5) | |
C22 | 0.32840 (15) | 0.56028 (8) | 0.26461 (18) | 0.0486 (6) | |
C23 | 0.35180 (16) | 0.60072 (9) | 0.33827 (18) | 0.0545 (6) | |
C24 | 0.38339 (15) | 0.65037 (8) | 0.31102 (18) | 0.0500 (6) | |
C25 | 0.39243 (14) | 0.65918 (8) | 0.20995 (18) | 0.0464 (5) | |
C26 | 0.36950 (13) | 0.61855 (8) | 0.13610 (17) | 0.0427 (5) | |
N31 | 0.43551 (11) | 0.22495 (6) | 0.15909 (14) | 0.0454 (5) | |
C32 | 0.46443 (12) | 0.17660 (7) | 0.20493 (16) | 0.0366 (5) | |
C33 | 0.42827 (13) | 0.12595 (8) | 0.16557 (17) | 0.0435 (5) | |
C34 | 0.35779 (14) | 0.12676 (9) | 0.08027 (19) | 0.0525 (6) | |
C35 | 0.32814 (15) | 0.17518 (10) | 0.0368 (2) | 0.0594 (7) | |
C36 | 0.37003 (15) | 0.22315 (9) | 0.07717 (19) | 0.0571 (6) | |
C37 | 0.46525 (16) | 0.07569 (8) | 0.21074 (19) | 0.0561 (6) | |
N41 | 0.39058 (13) | 0.79510 (7) | 0.29143 (16) | 0.0587 (5) | |
C42 | 0.43405 (14) | 0.83940 (8) | 0.33762 (17) | 0.0432 (5) | |
C43 | 0.40639 (13) | 0.89354 (8) | 0.31043 (17) | 0.0430 (5) | |
C44 | 0.33280 (15) | 0.90033 (10) | 0.23003 (19) | 0.0543 (6) | |
C45 | 0.28969 (16) | 0.85595 (11) | 0.1843 (2) | 0.0650 (7) | |
C46 | 0.32111 (17) | 0.80426 (11) | 0.2181 (2) | 0.0696 (7) | |
C47 | 0.45315 (15) | 0.93845 (9) | 0.36505 (19) | 0.0509 (6) | |
N51 | 0.53579 (13) | 0.77841 (7) | 0.44305 (17) | 0.0573 (5) | |
C52 | 0.50987 (13) | 0.83069 (8) | 0.41960 (17) | 0.0437 (5) | |
C53 | 0.55290 (13) | 0.87631 (8) | 0.47196 (18) | 0.0453 (5) | |
C54 | 0.62420 (15) | 0.86635 (10) | 0.5533 (2) | 0.0585 (6) | |
C55 | 0.64958 (16) | 0.81401 (11) | 0.5777 (2) | 0.0700 (8) | |
C56 | 0.60375 (17) | 0.77131 (10) | 0.5201 (2) | 0.0696 (8) | |
C57 | 0.52271 (15) | 0.93050 (9) | 0.44202 (19) | 0.0521 (6) | |
H14 | 0.4977 | 0.2981 | 0.1519 | 0.078* | |
H24 | 0.4147 | 0.7173 | 0.3635 | 0.118* | |
H12 | 0.2787 | 0.4107 | 0.1310 | 0.044* | |
H13 | 0.3650 | 0.3335 | 0.1577 | 0.049* | |
H15 | 0.5646 | 0.4223 | 0.1064 | 0.053* | |
H16 | 0.4790 | 0.4998 | 0.0834 | 0.050* | |
H22 | 0.3073 | 0.5270 | 0.2831 | 0.058* | |
H23 | 0.3464 | 0.5947 | 0.4067 | 0.065* | |
H25 | 0.4139 | 0.6924 | 0.1917 | 0.056* | |
H26 | 0.3764 | 0.6242 | 0.0681 | 0.051* | |
H34 | 0.3316 | 0.0941 | 0.0537 | 0.063* | |
H35 | 0.2807 | 0.1765 | −0.0189 | 0.071* | |
H36 | 0.3508 | 0.2561 | 0.0445 | 0.069* | |
H37 | 0.4406 | 0.0425 | 0.1851 | 0.067* | |
H44 | 0.3138 | 0.9354 | 0.2083 | 0.065* | |
H45 | 0.2403 | 0.8598 | 0.1318 | 0.078* | |
H46 | 0.2908 | 0.7739 | 0.1865 | 0.083* | |
H47 | 0.4350 | 0.9741 | 0.3468 | 0.061* | |
H54 | 0.6540 | 0.8955 | 0.5904 | 0.070* | |
H55 | 0.6967 | 0.8067 | 0.6318 | 0.084* | |
H56 | 0.6222 | 0.7356 | 0.5371 | 0.084* | |
H57 | 0.5517 | 0.9606 | 0.4764 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0414 (3) | 0.0326 (3) | 0.0410 (3) | 0.0001 (2) | −0.0006 (2) | −0.0005 (2) |
O11 | 0.0388 (8) | 0.0420 (8) | 0.0766 (12) | −0.0023 (7) | 0.0010 (7) | −0.0023 (8) |
O12 | 0.0722 (10) | 0.0470 (9) | 0.0366 (9) | 0.0024 (7) | −0.0001 (7) | 0.0064 (7) |
O14 | 0.0527 (9) | 0.0367 (8) | 0.0617 (11) | 0.0067 (7) | 0.0017 (8) | −0.0053 (8) |
O24 | 0.1305 (17) | 0.0460 (10) | 0.0591 (12) | −0.0276 (11) | 0.0183 (11) | −0.0170 (9) |
C11 | 0.0391 (11) | 0.0315 (10) | 0.0314 (11) | −0.0018 (8) | 0.0019 (8) | −0.0023 (8) |
C12 | 0.0370 (11) | 0.0362 (11) | 0.0350 (12) | −0.0033 (8) | 0.0041 (9) | −0.0001 (9) |
C13 | 0.0479 (12) | 0.0313 (10) | 0.0404 (12) | −0.0068 (9) | 0.0020 (9) | 0.0010 (9) |
C14 | 0.0450 (12) | 0.0352 (10) | 0.0361 (12) | 0.0038 (9) | 0.0003 (9) | −0.0042 (9) |
C15 | 0.0391 (11) | 0.0461 (12) | 0.0460 (13) | 0.0005 (9) | 0.0090 (10) | −0.0008 (10) |
C16 | 0.0485 (12) | 0.0348 (11) | 0.0422 (12) | −0.0066 (9) | 0.0091 (10) | 0.0017 (9) |
C21 | 0.0397 (11) | 0.0300 (10) | 0.0402 (12) | 0.0022 (8) | 0.0042 (9) | 0.0004 (9) |
C22 | 0.0637 (14) | 0.0320 (11) | 0.0500 (14) | −0.0088 (10) | 0.0118 (11) | 0.0027 (10) |
C23 | 0.0807 (17) | 0.0419 (12) | 0.0413 (13) | −0.0106 (12) | 0.0137 (12) | −0.0018 (10) |
C24 | 0.0618 (14) | 0.0356 (11) | 0.0487 (14) | −0.0047 (10) | 0.0034 (11) | −0.0069 (10) |
C25 | 0.0547 (13) | 0.0300 (11) | 0.0520 (14) | −0.0051 (9) | 0.0060 (11) | 0.0067 (10) |
C26 | 0.0487 (12) | 0.0366 (11) | 0.0413 (12) | −0.0025 (9) | 0.0064 (10) | 0.0038 (9) |
N31 | 0.0465 (10) | 0.0316 (9) | 0.0516 (11) | 0.0020 (7) | −0.0038 (9) | −0.0004 (8) |
C32 | 0.0403 (11) | 0.0278 (10) | 0.0416 (12) | 0.0011 (8) | 0.0085 (9) | −0.0011 (9) |
C33 | 0.0489 (12) | 0.0347 (11) | 0.0465 (13) | −0.0044 (9) | 0.0096 (10) | −0.0045 (9) |
C34 | 0.0501 (13) | 0.0454 (13) | 0.0577 (15) | −0.0101 (10) | 0.0020 (11) | −0.0098 (11) |
C35 | 0.0508 (14) | 0.0544 (14) | 0.0619 (16) | −0.0010 (11) | −0.0128 (12) | −0.0085 (12) |
C36 | 0.0556 (14) | 0.0451 (13) | 0.0603 (16) | 0.0066 (11) | −0.0108 (12) | 0.0005 (11) |
C37 | 0.0767 (17) | 0.0264 (10) | 0.0609 (16) | −0.0073 (10) | 0.0055 (12) | −0.0030 (10) |
N41 | 0.0599 (12) | 0.0434 (11) | 0.0673 (14) | −0.0075 (9) | 0.0014 (11) | −0.0071 (10) |
C42 | 0.0479 (12) | 0.0352 (11) | 0.0479 (13) | −0.0031 (9) | 0.0132 (10) | −0.0027 (9) |
C43 | 0.0458 (12) | 0.0402 (11) | 0.0463 (13) | 0.0041 (9) | 0.0168 (10) | 0.0030 (10) |
C44 | 0.0547 (14) | 0.0569 (14) | 0.0517 (15) | 0.0106 (11) | 0.0124 (11) | 0.0066 (12) |
C45 | 0.0531 (15) | 0.0798 (19) | 0.0560 (16) | 0.0043 (13) | −0.0016 (12) | −0.0030 (14) |
C46 | 0.0638 (16) | 0.0644 (17) | 0.0720 (19) | −0.0140 (13) | −0.0044 (14) | −0.0117 (14) |
C47 | 0.0588 (14) | 0.0311 (11) | 0.0658 (16) | 0.0044 (10) | 0.0197 (12) | 0.0041 (11) |
N51 | 0.0591 (12) | 0.0361 (10) | 0.0745 (15) | 0.0017 (9) | 0.0093 (11) | 0.0089 (10) |
C52 | 0.0454 (12) | 0.0343 (11) | 0.0525 (14) | −0.0013 (9) | 0.0128 (10) | 0.0030 (10) |
C53 | 0.0424 (12) | 0.0418 (12) | 0.0523 (14) | −0.0049 (9) | 0.0115 (10) | 0.0008 (10) |
C54 | 0.0468 (13) | 0.0615 (15) | 0.0642 (17) | −0.0138 (11) | 0.0056 (12) | −0.0003 (13) |
C55 | 0.0476 (14) | 0.0744 (18) | 0.081 (2) | −0.0006 (13) | −0.0023 (13) | 0.0232 (15) |
C56 | 0.0624 (16) | 0.0514 (15) | 0.092 (2) | 0.0076 (12) | 0.0096 (15) | 0.0245 (14) |
C57 | 0.0571 (14) | 0.0364 (12) | 0.0631 (16) | −0.0073 (10) | 0.0136 (12) | −0.0077 (11) |
O14—C14 | 1.352 (2) | C33—C34 | 1.401 (3) |
S1—C11 | 1.755 (2) | C33—C37 | 1.431 (3) |
S1—O11 | 1.4417 (15) | C34—C35 | 1.350 (3) |
O24—C24 | 1.350 (3) | C35—C36 | 1.392 (3) |
S1—C21 | 1.750 (2) | C37—C37i | 1.337 (5) |
S1—O12 | 1.4433 (15) | N41—C42 | 1.352 (3) |
C11—C12 | 1.386 (3) | N41—C46 | 1.317 (3) |
C11—C16 | 1.381 (3) | C42—C43 | 1.412 (3) |
C12—C13 | 1.379 (3) | C42—C52 | 1.446 (3) |
C13—C14 | 1.385 (3) | C43—C44 | 1.405 (3) |
C14—C15 | 1.389 (3) | C43—C47 | 1.426 (3) |
C15—C16 | 1.379 (3) | C44—C45 | 1.349 (3) |
C21—C22 | 1.386 (3) | C45—C46 | 1.392 (3) |
C21—C26 | 1.385 (3) | C47—C57 | 1.340 (3) |
C22—C23 | 1.373 (3) | N51—C52 | 1.354 (3) |
C23—C24 | 1.386 (3) | N51—C56 | 1.321 (3) |
C24—C25 | 1.378 (3) | C52—C53 | 1.404 (3) |
C25—C26 | 1.378 (3) | C53—C54 | 1.399 (3) |
N31—C32 | 1.357 (2) | C53—C57 | 1.431 (3) |
N31—C36 | 1.325 (3) | C54—C55 | 1.355 (3) |
C32—C32i | 1.448 (4) | C55—C56 | 1.395 (4) |
C32—C33 | 1.411 (3) | ||
C11—S1—C21 | 106.51 (9) | C32—C33—C34 | 118.13 (19) |
O14—C14—C13 | 122.51 (18) | C32—C33—C37 | 119.95 (19) |
O14—C14—C15 | 117.73 (19) | C34—C33—C37 | 121.90 (19) |
O11—S1—O12 | 117.75 (10) | C33—C34—C35 | 119.7 (2) |
O24—C24—C23 | 116.2 (2) | C34—C35—C36 | 118.6 (2) |
O24—C24—C25 | 123.7 (2) | N31—C36—C35 | 124.3 (2) |
O11—S1—C11 | 107.07 (9) | C37i—C37—C33 | 121.05 (12) |
O11—S1—C21 | 108.65 (10) | C42—N41—C46 | 117.3 (2) |
O12—S1—C11 | 108.35 (9) | N41—C42—C43 | 122.2 (2) |
O12—S1—C21 | 107.98 (9) | N41—C42—C52 | 118.58 (18) |
S1—C11—C12 | 119.27 (15) | C43—C42—C52 | 119.25 (18) |
S1—C11—C16 | 120.53 (15) | C42—C43—C44 | 117.6 (2) |
C12—C11—C16 | 120.02 (18) | C42—C43—C47 | 119.4 (2) |
C11—C12—C13 | 120.00 (18) | C44—C43—C47 | 123.0 (2) |
C12—C13—C14 | 120.01 (18) | C43—C44—C45 | 119.9 (2) |
C13—C14—C15 | 119.73 (18) | C44—C45—C46 | 118.1 (2) |
C14—C15—C16 | 120.1 (2) | N41—C46—C45 | 124.9 (2) |
C11—C16—C15 | 120.00 (19) | C43—C47—C57 | 121.5 (2) |
S1—C21—C22 | 119.36 (15) | C52—N51—C56 | 117.1 (2) |
S1—C21—C26 | 120.83 (16) | N51—C52—C42 | 118.07 (19) |
C22—C21—C26 | 119.78 (19) | N51—C52—C53 | 122.8 (2) |
C21—C22—C23 | 119.79 (19) | C42—C52—C53 | 119.11 (18) |
C22—C23—C24 | 120.3 (2) | C52—C53—C54 | 117.6 (2) |
C23—C24—C25 | 120.1 (2) | C52—C53—C57 | 119.8 (2) |
C24—C25—C26 | 119.74 (19) | C54—C53—C57 | 122.5 (2) |
C21—C26—C25 | 120.3 (2) | C53—C54—C55 | 119.6 (2) |
C32—N31—C36 | 117.49 (18) | C54—C55—C56 | 118.7 (2) |
N31—C32—C32i | 119.43 (11) | N51—C56—C55 | 124.1 (2) |
N31—C32—C33 | 121.69 (18) | C47—C57—C53 | 120.9 (2) |
C33—C32—C32i | 118.87 (12) | ||
O11—S1—C11—C12 | 2.0 (2) | C32—C33—C34—C35 | 1.7 (3) |
C11—S1—C21—C22 | −67.3 (2) | C37—C33—C34—C35 | −176.4 (2) |
C11—S1—C21—C26 | 114.8 (2) | C33—C34—C35—C36 | 1.3 (4) |
O12—S1—C21—C26 | −1.4 (2) | C32—N31—C36—C35 | 1.4 (4) |
C21—S1—C11—C12 | 118.1 (2) | C34—C35—C36—N31 | −3.1 (4) |
C21—S1—C11—C16 | −66.7 (2) | C34—C33—C37—C37i | 177.1 (3) |
O11—S1—C11—C16 | 177.22 (16) | C32—C33—C37—C37i | −0.9 (4) |
O12—S1—C11—C16 | 49.27 (18) | C46—N41—C42—C43 | 0.9 (3) |
O12—S1—C11—C12 | −125.93 (16) | C46—N41—C42—C52 | 179.1 (2) |
C16—C11—C12—C13 | −2.3 (3) | N41—C42—C43—C44 | −2.2 (3) |
S1—C11—C12—C13 | 172.89 (15) | C52—C42—C43—C44 | 179.6 (2) |
C11—C12—C13—C14 | −1.3 (3) | N41—C42—C43—C47 | 177.5 (2) |
C12—C13—C14—O14 | −177.87 (19) | C52—C42—C43—C47 | −0.7 (3) |
C12—C13—C14—C15 | 4.1 (3) | C42—C43—C44—C45 | 2.2 (3) |
O14—C14—C15—C16 | 178.52 (19) | C47—C43—C44—C45 | −177.4 (2) |
C13—C14—C15—C16 | −3.4 (3) | C43—C44—C45—C46 | −1.0 (4) |
C14—C15—C16—C11 | −0.2 (3) | C42—N41—C46—C45 | 0.5 (4) |
C12—C11—C16—C15 | 3.1 (3) | C44—C45—C46—N41 | −0.4 (4) |
S1—C11—C16—C15 | −172.08 (16) | C44—C43—C47—C57 | 179.4 (2) |
O11—S1—C21—C26 | −130.19 (17) | C42—C43—C47—C57 | −0.2 (3) |
O11—S1—C21—C22 | 47.77 (19) | C56—N51—C52—C53 | 1.2 (3) |
O12—S1—C21—C22 | 176.53 (17) | C56—N51—C52—C42 | −178.2 (2) |
C26—C21—C22—C23 | 1.4 (3) | N41—C42—C52—N51 | 2.8 (3) |
S1—C21—C22—C23 | −176.53 (18) | C43—C42—C52—N51 | −179.00 (19) |
C21—C22—C23—C24 | −0.1 (4) | N41—C42—C52—C53 | −176.7 (2) |
C22—C23—C24—O24 | 180.0 (2) | C43—C42—C52—C53 | 1.6 (3) |
C22—C23—C24—C25 | −0.8 (4) | N51—C52—C53—C54 | −1.6 (3) |
O24—C24—C25—C26 | 179.6 (2) | C42—C52—C53—C54 | 177.8 (2) |
C23—C24—C25—C26 | 0.3 (3) | N51—C52—C53—C57 | 179.0 (2) |
C24—C25—C26—C21 | 1.0 (3) | C42—C52—C53—C57 | −1.6 (3) |
C22—C21—C26—C25 | −1.9 (3) | C52—C53—C54—C55 | 0.7 (3) |
S1—C21—C26—C25 | 176.08 (16) | C57—C53—C54—C55 | −179.9 (2) |
C36—N31—C32—C33 | 1.8 (3) | C53—C54—C55—C56 | 0.3 (4) |
C36—N31—C32—C32i | −179.7 (2) | C52—N51—C56—C55 | −0.1 (4) |
N31—C32—C33—C34 | −3.4 (3) | C54—C55—C56—N51 | −0.7 (4) |
C32i—C32—C33—C34 | 178.1 (2) | C43—C47—C57—C53 | 0.3 (4) |
N31—C32—C33—C37 | 174.8 (2) | C54—C53—C57—C47 | −178.7 (2) |
C32i—C32—C33—C37 | −3.7 (4) | C52—C53—C57—C47 | 0.6 (3) |
Symmetry code: (i) −x+1, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O14—H14···N31 | 0.82 | 2.05 | 2.861 (2) | 171 |
O24—H24···N41 | 0.82 | 2.12 | 2.896 (2) | 159 |
O24—H24···N51 | 0.82 | 2.48 | 3.015 (3) | 124 |
C12—H12···O11 | 0.93 | 2.47 | 2.861 (3) | 106 |
C15—H15···O12ii | 0.93 | 2.55 | 3.406 (3) | 153 |
C26—H26···O12 | 0.93 | 2.53 | 2.911 (3) | 105 |
Symmetry code: (ii) −x+1, −y+1, −z. |
C20H18O3·C12H8N2·CH4O | ? #Insert any comments here. |
Mr = 518.59 | Dx = 1.270 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 25 reflections |
a = 22.811 (3) Å | θ = 9.9–15.7° |
b = 22.029 (3) Å | µ = 0.08 mm−1 |
c = 10.7965 (10) Å | T = 294 K |
V = 5425.3 (12) Å3 | Plate, colorless |
Z = 8 | 0.42 × 0.42 × 0.14 mm |
F(000) = 2192 |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.008 |
Radiation source: X-ray tube | θmax = 25.2°, θmin = 2.0° |
Graphite monochromator | h = 0→27 |
θ/2θ scans | k = 0→26 |
5200 measured reflections | l = 0→12 |
4861 independent reflections | 3 standard reflections every 120 min |
2178 reflections with I > 2σ(I) | intensity decay: 1.6% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.108 | Calculated w = 1/[σ2(Fo2) + (0.058P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.87 | (Δ/σ)max < 0.001 |
4861 reflections | Δρmax = 0.16 e Å−3 |
358 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0025 (3) |
C20H18O3·C12H8N2·CH4O | V = 5425.3 (12) Å3 |
Mr = 518.59 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 22.811 (3) Å | µ = 0.08 mm−1 |
b = 22.029 (3) Å | T = 294 K |
c = 10.7965 (10) Å | 0.42 × 0.42 × 0.14 mm |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.008 |
5200 measured reflections | 3 standard reflections every 120 min |
4861 independent reflections | intensity decay: 1.6% |
2178 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 0.87 | Δρmax = 0.16 e Å−3 |
4861 reflections | Δρmin = −0.14 e Å−3 |
358 parameters |
Experimental. ? #Insert any special details here. |
Geometry. Mean plane data ex last SHELXL run Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 0.7510 (0.0630) x + 5.6997 (0.0266) y + 10.4228 (0.0040) z = 5.5646 (0.0090) * 0.0000 (0.0000) C1 * 0.0000 (0.0000) C2 * 0.0000 (0.0000) C11 Rms deviation of fitted atoms = 0.0000 - 15.8689 (0.0101) x + 7.8947 (0.0125) y - 6.7217 (0.0072) z = 0.6987 (0.0060) Angle to previous plane (with approximate e.s.d.) = 60.96 (13) * 0.0067 (0.0013) C1 * -0.0019 (0.0016) C11 * -0.0018 (0.0015) C12 * -0.0030 (0.0016) C13 * -0.0048 (0.0019) C14 * 0.0102 (0.0015) O14 * -0.0052 (0.0017) C15 * -0.0003 (0.0016) C16 Rms deviation of fitted atoms = 0.0052 - 16.4518 (0.0182) x - 8.6530 (0.0500) y + 6.1601 (0.0157) z = 4.4005 (0.0122) * 0.0000 (0.0000) C1 * 0.0000 (0.0000) C2 * 0.0000 (0.0000) C21 Rms deviation of fitted atoms = 0.0000 - 19.2700 (0.0055) x + 3.8554 (0.0178) y + 5.4598 (0.0042) z = 6.2178 (0.0016) Angle to previous plane (with approximate e.s.d.) = 34.00 (10) * 0.0004 (0.0013) C1 * -0.0092 (0.0016) C21 * 0.0030 (0.0015) C22 * 0.0045 (0.0016) C23 * -0.0044 (0.0017) C24 * -0.0016 (0.0013) O24 * 0.0020 (0.0015) C25 * 0.0054 (0.0016) C26 Rms deviation of fitted atoms = 0.0046 15.3348 (0.0187) x + 13.9865 (0.0335) y + 4.1106 (0.0242) z = 1.1091 (0.0106) * 0.0000 (0.0000) C1 * 0.0000 (0.0000) C2 * 0.0000 (0.0000) C31 Rms deviation of fitted atoms = 0.0000 6.6356 (0.0169) x + 21.0757 (0.0059) y + 0.0834 (0.0072) z = 1.7333 (0.0037) Angle to previous plane (with approximate e.s.d.) = 36.30 (13) * -0.0258 (0.0013) C1 * -0.0158 (0.0016) C31 * 0.0114 (0.0017) C32 * 0.0274 (0.0017) C33 * 0.0042 (0.0018) C34 * -0.0432 (0.0014) O34 * 0.0237 (0.0018) C35 * 0.0181 (0.0018) C36 Rms deviation of fitted atoms = 0.0239 13.1477 (0.0061) x + 13.8758 (0.0079) y - 5.6207 (0.0046) z = 2.4056 (0.0060) * -0.0078 (0.0017) N41 * -0.0214 (0.0021) C42 * -0.0141 (0.0026) C43 * 0.0072 (0.0026) C44 * 0.0100 (0.0022) C45 * 0.0189 (0.0024) C46 * -0.0041 (0.0025) C47 * -0.0056 (0.0022) C48 * -0.0277 (0.0026) C49 * -0.0188 (0.0027) C410 * 0.0156 (0.0021) C411 * 0.0294 (0.0017) N412 * 0.0111 (0.0019) C413 * 0.0073 (0.0019) C414 Rms deviation of fitted atoms = 0.0162 |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | −0.16889 (7) | 0.13242 (8) | 0.44931 (19) | 0.0420 (5) | |
C2 | −0.12824 (9) | 0.07829 (9) | 0.4818 (2) | 0.0595 (6) | |
C11 | −0.12945 (7) | 0.18741 (8) | 0.42207 (19) | 0.0402 (5) | |
C12 | −0.13105 (8) | 0.24074 (9) | 0.48848 (19) | 0.0471 (5) | |
C13 | −0.09496 (9) | 0.28919 (9) | 0.4603 (2) | 0.0514 (5) | |
C14 | −0.05624 (9) | 0.28508 (9) | 0.3644 (2) | 0.0526 (6) | |
O14 | −0.01994 (9) | 0.33235 (8) | 0.33196 (16) | 0.0879 (6) | |
C15 | −0.05346 (9) | 0.23247 (10) | 0.2961 (2) | 0.0583 (6) | |
C16 | −0.08960 (9) | 0.18476 (9) | 0.3246 (2) | 0.0533 (6) | |
C21 | −0.20458 (8) | 0.11707 (8) | 0.33243 (19) | 0.0420 (5) | |
C22 | −0.22405 (9) | 0.05840 (9) | 0.3074 (2) | 0.0521 (6) | |
C23 | −0.25645 (9) | 0.04520 (10) | 0.2026 (2) | 0.0574 (6) | |
C24 | −0.27059 (8) | 0.09013 (10) | 0.1193 (2) | 0.0506 (6) | |
O24 | −0.30283 (7) | 0.07455 (7) | 0.01706 (14) | 0.0709 (5) | |
C25 | −0.25273 (8) | 0.14858 (9) | 0.14228 (19) | 0.0513 (5) | |
C26 | −0.22046 (9) | 0.16144 (9) | 0.2477 (2) | 0.0491 (5) | |
C31 | −0.21001 (8) | 0.14540 (8) | 0.55852 (19) | 0.0425 (5) | |
C32 | −0.26691 (8) | 0.16467 (10) | 0.5431 (2) | 0.0558 (6) | |
C33 | −0.30353 (9) | 0.17657 (10) | 0.6424 (2) | 0.0591 (6) | |
C34 | −0.28382 (9) | 0.16879 (9) | 0.7608 (2) | 0.0510 (6) | |
O34 | −0.31872 (6) | 0.17712 (8) | 0.86381 (14) | 0.0723 (5) | |
C35 | −0.22688 (9) | 0.15172 (11) | 0.7795 (2) | 0.0665 (7) | |
C36 | −0.19098 (9) | 0.14054 (10) | 0.6794 (2) | 0.0630 (7) | |
N41 | 0.02443 (9) | 0.37652 (10) | 0.56006 (19) | 0.0681 (6) | |
C42 | 0.07088 (13) | 0.34605 (14) | 0.5959 (3) | 0.0935 (9) | |
C43 | 0.10249 (14) | 0.3596 (2) | 0.7021 (4) | 0.1140 (13) | |
C44 | 0.08533 (15) | 0.4065 (2) | 0.7739 (3) | 0.1087 (12) | |
C45 | 0.03554 (13) | 0.44034 (14) | 0.7404 (3) | 0.0792 (8) | |
C46 | 0.01375 (17) | 0.49021 (17) | 0.8110 (3) | 0.1045 (12) | |
C47 | −0.03415 (19) | 0.51962 (15) | 0.7756 (4) | 0.1081 (12) | |
C48 | −0.06523 (14) | 0.50418 (12) | 0.6651 (3) | 0.0791 (8) | |
C49 | −0.11577 (18) | 0.53446 (14) | 0.6256 (4) | 0.1081 (12) | |
C410 | −0.14212 (15) | 0.51726 (19) | 0.5199 (5) | 0.1152 (14) | |
C411 | −0.11815 (14) | 0.47019 (15) | 0.4536 (3) | 0.0954 (10) | |
N412 | −0.07091 (9) | 0.43950 (9) | 0.4859 (2) | 0.0711 (6) | |
C413 | −0.04475 (10) | 0.45656 (10) | 0.5925 (2) | 0.0591 (6) | |
C414 | 0.00641 (10) | 0.42342 (11) | 0.6310 (2) | 0.0590 (6) | |
O51 | 0.06663 (7) | 0.31812 (10) | 0.16278 (16) | 0.0862 (6) | |
C51 | 0.03656 (12) | 0.32226 (14) | 0.0494 (3) | 0.0935 (9) | |
H2A | −0.1015 | 0.0902 | 0.5460 | 0.089* | |
H2B | −0.1066 | 0.0664 | 0.4096 | 0.089* | |
H2C | −0.1515 | 0.0447 | 0.5101 | 0.089* | |
H12 | −0.1572 | 0.2443 | 0.5542 | 0.057* | |
H13 | −0.0971 | 0.3246 | 0.5069 | 0.062* | |
H14 | −0.0159 | 0.3552 | 0.3913 | 0.132* | |
H15 | −0.0271 | 0.2293 | 0.2307 | 0.070* | |
H16 | −0.0874 | 0.1495 | 0.2774 | 0.064* | |
H22 | −0.2150 | 0.0273 | 0.3625 | 0.062* | |
H23 | −0.2688 | 0.0056 | 0.1883 | 0.069* | |
H24 | −0.3113 | 0.1053 | −0.0219 | 0.106* | |
H25 | −0.2623 | 0.1795 | 0.0871 | 0.062* | |
H26 | −0.2090 | 0.2013 | 0.2623 | 0.059* | |
H32 | −0.2813 | 0.1699 | 0.4632 | 0.067* | |
H33 | −0.3417 | 0.1899 | 0.6285 | 0.071* | |
H34 | −0.3530 | 0.1804 | 0.8422 | 0.108* | |
H35 | −0.2124 | 0.1476 | 0.8596 | 0.080* | |
H36 | −0.1523 | 0.1293 | 0.6939 | 0.076* | |
H42 | 0.0833 | 0.3136 | 0.5475 | 0.112* | |
H43 | 0.1352 | 0.3367 | 0.7235 | 0.137* | |
H44 | 0.1063 | 0.4164 | 0.8450 | 0.130* | |
H46 | 0.0333 | 0.5022 | 0.8825 | 0.125* | |
H47 | −0.0480 | 0.5513 | 0.8244 | 0.130* | |
H49 | −0.1310 | 0.5663 | 0.6721 | 0.130* | |
H410 | −0.1758 | 0.5368 | 0.4923 | 0.138* | |
H411 | −0.1367 | 0.4591 | 0.3803 | 0.114* | |
H51 | 0.0431 | 0.3206 | 0.2201 | 0.129* | |
H51A | 0.0576 | 0.3000 | −0.0130 | 0.130* | 0.50 |
H51B | −0.0020 | 0.3055 | 0.0582 | 0.130* | 0.50 |
H51C | 0.0336 | 0.3640 | 0.0249 | 0.130* | 0.50 |
H51D | 0.0258 | 0.2823 | 0.0218 | 0.130* | 0.50 |
H51E | 0.0019 | 0.3463 | 0.0597 | 0.130* | 0.50 |
H51F | 0.0615 | 0.3408 | −0.0115 | 0.130* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0434 (11) | 0.0421 (11) | 0.0405 (13) | 0.0008 (9) | −0.0022 (10) | 0.0013 (10) |
C2 | 0.0634 (13) | 0.0551 (13) | 0.0601 (17) | 0.0066 (11) | −0.0050 (12) | 0.0053 (12) |
C11 | 0.0398 (11) | 0.0459 (11) | 0.0348 (13) | 0.0001 (9) | 0.0002 (10) | 0.0000 (10) |
C12 | 0.0490 (11) | 0.0558 (13) | 0.0365 (13) | −0.0018 (10) | 0.0088 (10) | −0.0021 (11) |
C13 | 0.0619 (13) | 0.0483 (12) | 0.0438 (14) | −0.0100 (11) | 0.0080 (12) | −0.0058 (11) |
C14 | 0.0575 (13) | 0.0612 (14) | 0.0391 (14) | −0.0198 (11) | 0.0062 (12) | −0.0030 (12) |
O14 | 0.1103 (13) | 0.0897 (12) | 0.0636 (13) | −0.0553 (10) | 0.0359 (11) | −0.0190 (10) |
C15 | 0.0549 (13) | 0.0776 (16) | 0.0425 (14) | −0.0150 (11) | 0.0172 (11) | −0.0090 (13) |
C16 | 0.0544 (12) | 0.0571 (13) | 0.0483 (15) | −0.0084 (11) | 0.0129 (12) | −0.0130 (11) |
C21 | 0.0467 (11) | 0.0419 (11) | 0.0376 (13) | −0.0009 (9) | 0.0056 (10) | 0.0008 (11) |
C22 | 0.0630 (13) | 0.0441 (12) | 0.0491 (15) | −0.0061 (10) | 0.0011 (12) | 0.0030 (11) |
C23 | 0.0665 (14) | 0.0485 (13) | 0.0572 (16) | −0.0142 (11) | 0.0021 (13) | −0.0060 (12) |
C24 | 0.0539 (13) | 0.0614 (14) | 0.0366 (14) | −0.0117 (11) | 0.0041 (11) | −0.0098 (12) |
O24 | 0.0859 (11) | 0.0816 (11) | 0.0453 (11) | −0.0203 (10) | −0.0076 (9) | −0.0106 (9) |
C25 | 0.0622 (13) | 0.0547 (13) | 0.0370 (13) | −0.0078 (11) | −0.0013 (12) | 0.0035 (11) |
C26 | 0.0591 (13) | 0.0440 (12) | 0.0442 (14) | −0.0097 (10) | 0.0001 (11) | −0.0031 (11) |
C31 | 0.0433 (11) | 0.0473 (12) | 0.0368 (14) | −0.0051 (9) | −0.0003 (10) | 0.0059 (10) |
C32 | 0.0545 (13) | 0.0795 (15) | 0.0335 (13) | 0.0103 (11) | −0.0033 (11) | 0.0045 (12) |
C33 | 0.0487 (12) | 0.0856 (16) | 0.0429 (15) | 0.0137 (11) | −0.0037 (12) | −0.0004 (13) |
C34 | 0.0479 (13) | 0.0663 (14) | 0.0388 (15) | −0.0057 (11) | 0.0026 (11) | 0.0001 (12) |
O34 | 0.0544 (9) | 0.1226 (13) | 0.0398 (10) | 0.0026 (10) | 0.0050 (8) | −0.0052 (9) |
C35 | 0.0514 (13) | 0.115 (2) | 0.0334 (14) | −0.0043 (13) | −0.0048 (12) | 0.0093 (14) |
C36 | 0.0424 (12) | 0.1016 (19) | 0.0449 (16) | 0.0021 (12) | −0.0022 (12) | 0.0135 (14) |
N41 | 0.0611 (12) | 0.0741 (13) | 0.0691 (15) | −0.0114 (10) | 0.0048 (12) | 0.0067 (13) |
C42 | 0.0723 (18) | 0.105 (2) | 0.104 (3) | −0.0053 (18) | 0.016 (2) | 0.020 (2) |
C43 | 0.069 (2) | 0.159 (4) | 0.114 (3) | −0.009 (2) | −0.002 (2) | 0.056 (3) |
C44 | 0.078 (2) | 0.175 (4) | 0.073 (3) | −0.048 (2) | −0.016 (2) | 0.038 (3) |
C45 | 0.0784 (19) | 0.105 (2) | 0.0546 (19) | −0.0466 (17) | −0.0034 (16) | 0.0126 (18) |
C46 | 0.134 (3) | 0.121 (3) | 0.058 (2) | −0.071 (2) | 0.007 (2) | −0.017 (2) |
C47 | 0.150 (3) | 0.082 (2) | 0.093 (3) | −0.045 (2) | 0.045 (3) | −0.023 (2) |
C48 | 0.096 (2) | 0.0594 (16) | 0.082 (2) | −0.0229 (16) | 0.0248 (19) | 0.0002 (17) |
C49 | 0.110 (3) | 0.070 (2) | 0.144 (4) | 0.006 (2) | 0.044 (3) | 0.021 (2) |
C410 | 0.085 (2) | 0.099 (3) | 0.162 (4) | −0.003 (2) | 0.013 (3) | 0.050 (3) |
C411 | 0.087 (2) | 0.089 (2) | 0.110 (3) | −0.0259 (18) | −0.022 (2) | 0.034 (2) |
N412 | 0.0746 (14) | 0.0687 (13) | 0.0700 (17) | −0.0213 (11) | −0.0152 (12) | 0.0103 (12) |
C413 | 0.0658 (15) | 0.0523 (14) | 0.0593 (17) | −0.0238 (12) | 0.0076 (14) | 0.0080 (14) |
C414 | 0.0629 (15) | 0.0635 (14) | 0.0505 (16) | −0.0288 (13) | 0.0021 (13) | 0.0051 (13) |
O51 | 0.0582 (9) | 0.1455 (16) | 0.0548 (12) | −0.0236 (11) | −0.0002 (9) | −0.0008 (12) |
C51 | 0.097 (2) | 0.124 (2) | 0.060 (2) | −0.0228 (17) | −0.0107 (17) | 0.0039 (17) |
C14—O14 | 1.376 (2) | C32—C33 | 1.385 (3) |
C34—O34 | 1.380 (2) | C33—C34 | 1.365 (3) |
C1—C2 | 1.551 (2) | C34—C35 | 1.367 (3) |
C1—C11 | 1.537 (2) | C35—C36 | 1.378 (3) |
C1—C21 | 1.539 (3) | N41—C42 | 1.313 (3) |
C1—C31 | 1.534 (3) | N41—C414 | 1.350 (3) |
C11—C12 | 1.377 (3) | C42—C43 | 1.387 (4) |
C11—C16 | 1.392 (3) | C43—C44 | 1.350 (5) |
C12—C13 | 1.382 (3) | C44—C45 | 1.405 (4) |
C13—C14 | 1.365 (3) | C45—C414 | 1.406 (3) |
C14—C15 | 1.375 (3) | C45—C46 | 1.426 (4) |
C15—C16 | 1.371 (3) | C46—C47 | 1.326 (4) |
C21—C22 | 1.393 (3) | C47—C48 | 1.429 (4) |
C21—C26 | 1.387 (3) | C48—C49 | 1.399 (4) |
C22—C23 | 1.382 (3) | C48—C413 | 1.391 (3) |
C23—C24 | 1.376 (3) | C49—C410 | 1.344 (4) |
C24—O24 | 1.370 (2) | C410—C411 | 1.373 (4) |
C24—C25 | 1.373 (3) | C411—N412 | 1.319 (3) |
C25—C26 | 1.385 (3) | N412—C413 | 1.350 (3) |
C31—C32 | 1.376 (3) | C413—C414 | 1.438 (3) |
C31—C36 | 1.379 (3) | O51—C51 | 1.406 (3) |
C13—C14—O14 | 122.2 (2) | C1—C31—C36 | 121.36 (17) |
C23—C24—O24 | 118.2 (2) | C32—C31—C36 | 115.8 (2) |
C33—C34—O34 | 123.2 (2) | C31—C32—C33 | 122.3 (2) |
O14—C14—C15 | 118.3 (2) | C32—C33—C34 | 120.17 (19) |
O24—C24—C25 | 122.6 (2) | C33—C34—C35 | 119.0 (2) |
O34—C34—C35 | 117.7 (2) | C35—C36—C31 | 122.75 (19) |
C2—C1—C11 | 107.42 (14) | C34—C35—C36 | 119.9 (2) |
C2—C1—C21 | 109.45 (16) | C42—N41—C414 | 118.0 (3) |
C2—C1—C31 | 109.57 (16) | N41—C42—C43 | 123.6 (3) |
C11—C1—C21 | 109.02 (15) | C42—C43—C44 | 119.3 (3) |
C11—C1—C31 | 110.97 (15) | C43—C44—C45 | 119.5 (3) |
C1—C11—C12 | 123.87 (17) | C44—C45—C46 | 123.5 (3) |
C1—C11—C16 | 119.59 (17) | C44—C45—C414 | 117.2 (3) |
C21—C1—C31 | 110.35 (14) | C46—C45—C414 | 119.2 (3) |
C12—C11—C16 | 116.53 (17) | C45—C46—C47 | 120.6 (3) |
C11—C12—C13 | 121.93 (18) | C46—C47—C48 | 122.2 (3) |
C12—C13—C14 | 120.09 (19) | C47—C48—C49 | 123.4 (4) |
C13—C14—C15 | 119.53 (18) | C47—C48—C413 | 118.9 (3) |
C14—C15—C16 | 119.86 (19) | C49—C48—C413 | 117.7 (3) |
C11—C16—C15 | 122.06 (19) | C48—C49—C410 | 119.6 (4) |
C1—C21—C22 | 122.12 (18) | C49—C410—C411 | 118.5 (4) |
C1—C21—C26 | 121.60 (16) | N412—C411—C410 | 125.1 (3) |
C22—C21—C26 | 116.26 (19) | C411—N412—C413 | 116.3 (3) |
C21—C22—C23 | 121.7 (2) | N412—C413—C48 | 122.8 (3) |
C22—C23—C24 | 120.60 (19) | N412—C413—C414 | 117.7 (2) |
C23—C24—C25 | 119.2 (2) | C48—C413—C414 | 119.5 (3) |
C24—C25—C26 | 119.9 (2) | N41—C414—C45 | 122.4 (3) |
C21—C26—C25 | 122.46 (18) | N41—C414—C413 | 118.1 (2) |
C1—C31—C32 | 122.78 (19) | C45—C414—C413 | 119.5 (3) |
C2—C1—C11—C12 | −119.3 (2) | C31—C32—C33—C34 | −0.6 (3) |
C2—C1—C21—C22 | 34.8 (2) | C32—C33—C34—C35 | 2.8 (3) |
C2—C1—C31—C32 | −144.8 (2) | C32—C33—C34—O34 | −177.0 (2) |
C2—C1—C11—C16 | 61.2 (2) | C32—C31—C36—C35 | 2.6 (3) |
C2—C1—C21—C26 | −146.9 (2) | C1—C31—C36—C35 | −179.80 (19) |
C2—C1—C31—C36 | 37.7 (2) | C33—C34—C35—C36 | −2.3 (3) |
C31—C1—C11—C12 | 0.5 (2) | O34—C34—C35—C36 | 177.5 (2) |
C21—C1—C11—C12 | 122.2 (2) | C31—C36—C35—C34 | −0.4 (4) |
C31—C1—C11—C16 | −179.03 (17) | C414—N41—C42—C43 | −0.3 (4) |
C21—C1—C11—C16 | −57.3 (2) | N41—C42—C43—C44 | 0.0 (5) |
C16—C11—C12—C13 | −0.1 (3) | C42—C43—C44—C45 | 0.5 (5) |
C1—C11—C12—C13 | −179.67 (17) | C43—C44—C45—C414 | −0.8 (4) |
C11—C12—C13—C14 | 0.0 (3) | C43—C44—C45—C46 | 179.4 (3) |
C12—C13—C14—C15 | 0.0 (3) | C44—C45—C46—C47 | −178.7 (3) |
C12—C13—C14—O14 | 179.2 (2) | C414—C45—C46—C47 | 1.4 (4) |
C13—C14—C15—C16 | 0.2 (3) | C45—C46—C47—C48 | −1.6 (5) |
O14—C14—C15—C16 | −179.1 (2) | C46—C47—C48—C413 | 0.3 (4) |
C14—C15—C16—C11 | −0.3 (3) | C46—C47—C48—C49 | −179.9 (3) |
C12—C11—C16—C15 | 0.3 (3) | C413—C48—C49—C410 | −0.6 (4) |
C1—C11—C16—C15 | 179.88 (19) | C47—C48—C49—C410 | 179.6 (3) |
C31—C1—C21—C26 | 92.4 (2) | C48—C49—C410—C411 | −0.2 (5) |
C11—C1—C21—C26 | −29.7 (2) | C49—C410—C411—N412 | 0.6 (5) |
C31—C1—C21—C22 | −85.8 (2) | C410—C411—N412—C413 | −0.2 (4) |
C11—C1—C21—C22 | 152.04 (17) | C411—N412—C413—C48 | −0.7 (3) |
C26—C21—C22—C23 | 1.2 (3) | C411—N412—C413—C414 | 179.18 (19) |
C1—C21—C22—C23 | 179.50 (18) | C49—C48—C413—N412 | 1.1 (3) |
C21—C22—C23—C24 | −0.1 (3) | C47—C48—C413—N412 | −179.1 (2) |
C22—C23—C24—O24 | −179.96 (18) | C49—C48—C413—C414 | −178.8 (2) |
C22—C23—C24—C25 | −0.8 (3) | C47—C48—C413—C414 | 1.0 (3) |
O24—C24—C25—C26 | 179.68 (19) | C42—N41—C414—C45 | 0.1 (3) |
C23—C24—C25—C26 | 0.6 (3) | C42—N41—C414—C413 | −179.5 (2) |
C24—C25—C26—C21 | 0.6 (3) | C44—C45—C414—N41 | 0.5 (3) |
C22—C21—C26—C25 | −1.4 (3) | C46—C45—C414—N41 | −179.7 (2) |
C1—C21—C26—C25 | −179.76 (18) | C44—C45—C414—C413 | −179.9 (2) |
C11—C1—C31—C32 | 96.7 (2) | C46—C45—C414—C413 | −0.1 (3) |
C21—C1—C31—C32 | −24.2 (2) | N412—C413—C414—N41 | −1.4 (3) |
C11—C1—C31—C36 | −80.7 (2) | C48—C413—C414—N41 | 178.47 (19) |
C21—C1—C31—C36 | 158.30 (19) | N412—C413—C414—C45 | 178.99 (19) |
C36—C31—C32—C33 | −2.0 (3) | C48—C413—C414—C45 | −1.1 (3) |
C1—C31—C32—C33 | −179.64 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O14—H14···N41 | 0.82 | 2.09 | 2.835 (3) | 150 |
O14—H14···N412 | 0.82 | 2.46 | 3.112 (3) | 137 |
O24—H24···O34i | 0.82 | 2.01 | 2.824 (2) | 169 |
O34—H34···O51ii | 0.82 | 1.83 | 2.633 (2) | 165 |
O51—H51···O14 | 0.82 | 1.90 | 2.708 (3) | 170 |
C13—H13···N412 | 0.93 | 2.61 | 3.368 (3) | 139 |
C44—H44···O24iii | 0.93 | 2.56 | 3.432 (4) | 156 |
Symmetry codes: (i) x, y, z−1; (ii) x−1/2, −y+1/2, −z+1; (iii) x+1/2, −y+1/2, −z+1. |
Experimental details
(1) | (2) | (3) | (4) | |
Crystal data | ||||
Chemical formula | C12H10O2·C12H8N2 | C12H10O2S·2(C12H8N2) | 2(C12H10O4S)·3(C12H8N2) | C20H18O3·C12H8N2·CH4O |
Mr | 366.40 | 578.69 | 1041.13 | 518.59 |
Crystal system, space group | Monoclinic, C2/c | Triclinic, P1 | Monoclinic, C2/c | Orthorhombic, Pbca |
Temperature (K) | 294 | 294 | 294 | 294 |
a, b, c (Å) | 13.0288 (17), 12.1865 (10), 12.0778 (12) | 7.7342 (5), 13.3624 (14), 14.9843 (11) | 15.8692 (16), 24.3728 (17), 13.0952 (9) | 22.811 (3), 22.029 (3), 10.7965 (10) |
α, β, γ (°) | 90, 105.199 (9), 90 | 110.514 (6), 95.195 (6), 95.895 (7) | 90, 102.362 (8), 90 | 90, 90, 90 |
V (Å3) | 1850.6 (3) | 1429.3 (2) | 4947.5 (7) | 5425.3 (12) |
Z | 4 | 2 | 4 | 8 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.09 | 0.16 | 0.18 | 0.08 |
Crystal size (mm) | 0.42 × 0.31 × 0.12 | 0.42 × 0.35 × 0.22 | 0.42 × 0.38 × 0.10 | 0.42 × 0.42 × 0.14 |
Data collection | ||||
Diffractometer | Enraf-Nonius CAD-4 diffractometer | Enraf-Nonius CAD-4 diffractometer | Enraf-Nonius CAD-4 diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | – | Gaussian ABSORB in NRCVAX (Gabe et al., 1989) | Gaussian ABSORB in NRCVAX (Gabe et al., 1989) | – |
Tmin, Tmax | – | 0.946, 0.970 | 0.937, 0.983 | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1748, 1678, 915 | 5184, 5184, 3431 | 4636, 4434, 3182 | 5200, 4861, 2178 |
Rint | 0.012 | 0.000 | 0.006 | 0.008 |
(sin θ/λ)max (Å−1) | 0.599 | 0.599 | 0.598 | 0.598 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.099, 0.98 | 0.035, 0.100, 1.04 | 0.041, 0.104, 1.03 | 0.039, 0.108, 0.87 |
No. of reflections | 1678 | 5184 | 4434 | 4861 |
No. of parameters | 129 | 391 | 346 | 358 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.13 | 0.20, −0.20 | 0.22, −0.30 | 0.16, −0.14 |
Computer programs: CAD4 (Enraf-Nonius, 1992), SET4 & CELDIM (Enraf-Nonius, 1992), DATRD2 in NRCVAX96 (Gabe et al., 1989), DATRD2 in NRCVAX96 (Gabe et al., 1989 1989), SHELXS97 (Sheldrick, 1997a), NRCVAX96 and SHELXL97 (Sheldrick, 1997b), NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1998), NRCVAX96, SHELXL97 and WORDPERFECT macro PRPCIF97 (Ferguson, 1997).
(1) | |||
O14···N1 | 2.878 (2) | O14—H14···N1 | 159 |
C12···O14i | 3.403 (2) | C12—H12···O14i | 148 |
(2) | |||
O14···N31 | 2.741 (2) | O14—H14···N31 | 153 |
O24···N51 | 2.757 (2) | O24—H24···N51 | 151 |
(3) | |||
O14···N31 | 2.861 (2) | O14—H14···N31 | 171 |
O24···N41 | 2.896 (2) | O24—H24···N41 | 159 |
O24···N51 | 3.015 (3) | O24—H24···N51 | 124 |
C15···O12ii | 3.406 (3) | C15—H15···O12ii | 153 |
(4) | |||
O51···O14 | 2.708 (3) | O51—H51···O14 | 170 |
O24···O34iii | 2.824 (2) | O24—H24···O34iii | 169 |
O34···O51iv | 2.633 (2) | O34—H34···O51iv | 165 |
O14···N41 | 2.835 (3) | O14—H14···N41 | 150 |
O14···N412 | 3.112 (3) | O14—H14···N412 | 137 |
C44···O24v | 3.432 (4) | C44—H44···O24v | 156 |
(i) x, 1-y, -1/2+z; (ii) 1-x, 1-y, -z; (iii) x, y, -1+z; (iv) -1/2+x, 1/2-y, 1-z; (v) 1/2+x, 1/2-y, 1-z. |