Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768112037457/ps5015sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768112037457/ps5015Z2sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768112037457/ps5015Z4sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768112037457/ps5015Z6sup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768112037457/ps5015Z10sup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768112037457/ps5015Me2PAsup6.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108768112037457/ps5015sup7.pdf |
CCDC references: 906602; 906603; 906604; 906605; 906606
For all compounds, data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C8H8N2O2 | Z = 2 |
Mr = 164.16 | F(000) = 172 |
Triclinic, P1 | Dx = 1.424 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 3.9506 (12) Å | Cell parameters from 2363 reflections |
b = 8.264 (3) Å | θ = 2.5–27.4° |
c = 12.045 (4) Å | µ = 0.11 mm−1 |
α = 78.842 (4)° | T = 173 K |
β = 83.180 (4)° | Flat needle, pale yellow |
γ = 86.990 (4)° | 0.50 × 0.13 × 0.06 mm |
V = 382.9 (2) Å3 |
Bruker SMART 1K CCD area-detector diffractometer | 1713 independent reflections |
Radiation source: fine-focus sealed tube | 1379 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ω scans | θmax = 27.5°, θmin = 1.7° |
Absorption correction: multi-scan SADABS; Sheldrick, 2008; Blessing, 1995 | h = −5→5 |
Tmin = 0.94, Tmax = 0.99 | k = −10→10 |
4353 measured reflections | l = 0→15 |
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)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.156 | w = 1/[σ2(Fo2) + (0.077P)2 + 0.136P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.002 |
1713 reflections | Δρmax = 0.26 e Å−3 |
153 parameters | Δρmin = −0.22 e Å−3 |
32 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.036 (12) |
C8H8N2O2 | γ = 86.990 (4)° |
Mr = 164.16 | V = 382.9 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 3.9506 (12) Å | Mo Kα radiation |
b = 8.264 (3) Å | µ = 0.11 mm−1 |
c = 12.045 (4) Å | T = 173 K |
α = 78.842 (4)° | 0.50 × 0.13 × 0.06 mm |
β = 83.180 (4)° |
Bruker SMART 1K CCD area-detector diffractometer | 1713 independent reflections |
Absorption correction: multi-scan SADABS; Sheldrick, 2008; Blessing, 1995 | 1379 reflections with I > 2σ(I) |
Tmin = 0.94, Tmax = 0.99 | Rint = 0.031 |
4353 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 32 restraints |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.26 e Å−3 |
1713 reflections | Δρmin = −0.22 e Å−3 |
153 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.1496 (4) | 0.70009 (19) | 0.91155 (13) | 0.0498 (5) | 0.893 (2) |
O2 | −0.0065 (4) | 0.73775 (17) | 0.72944 (12) | 0.0408 (4) | 0.893 (2) |
N1 | 0.1523 (4) | 0.6406 (2) | 0.82482 (14) | 0.0355 (4) | 0.893 (2) |
N2 | 0.0245 (5) | 0.6514 (2) | 0.64120 (15) | 0.0379 (4) | 0.893 (2) |
C1 | 0.2734 (5) | 0.5024 (2) | 0.79133 (16) | 0.0287 (4) | 0.893 (2) |
C2 | 0.1939 (5) | 0.5115 (2) | 0.67857 (16) | 0.0293 (4) | 0.893 (2) |
C3 | 0.2905 (8) | 0.3783 (3) | 0.62238 (18) | 0.0299 (4) | 0.893 (2) |
H3 | 0.2387 | 0.3817 | 0.5469 | 0.036* | 0.893 (2) |
C4 | 0.4600 (9) | 0.2444 (3) | 0.67855 (19) | 0.0285 (4) | 0.893 (2) |
C5 | 0.5368 (6) | 0.2371 (2) | 0.79559 (19) | 0.0281 (4) | 0.893 (2) |
C6 | 0.4453 (6) | 0.3642 (2) | 0.85114 (16) | 0.0298 (4) | 0.893 (2) |
H6 | 0.4948 | 0.3602 | 0.9269 | 0.036* | 0.893 (2) |
C7 | 0.566 (2) | 0.1021 (5) | 0.6203 (3) | 0.0382 (5) | 0.893 (2) |
H7A | 0.4984 | 0.1262 | 0.5430 | 0.057* | 0.893 (2) |
H7B | 0.4545 | 0.0022 | 0.6632 | 0.057* | 0.893 (2) |
H7C | 0.8140 | 0.0848 | 0.6167 | 0.057* | 0.893 (2) |
C8 | 0.7154 (6) | 0.0834 (3) | 0.8546 (2) | 0.0340 (6) | 0.893 (2) |
H8A | 0.7486 | 0.0957 | 0.9318 | 0.051* | 0.893 (2) |
H8B | 0.9374 | 0.0675 | 0.8117 | 0.051* | 0.893 (2) |
H8C | 0.5756 | −0.0125 | 0.8585 | 0.051* | 0.893 (2) |
O1A | −0.081 (3) | 0.7371 (12) | 0.6150 (8) | 0.048 (4) | 0.107 (2) |
O2A | 0.056 (3) | 0.7230 (10) | 0.7976 (8) | 0.0408 (4) | 0.107 (2) |
N1A | 0.058 (3) | 0.6545 (11) | 0.6949 (7) | 0.0379 (4) | 0.107 (2) |
N2A | 0.222 (3) | 0.6131 (11) | 0.8764 (7) | 0.0355 (4) | 0.107 (2) |
C1A | 0.218 (4) | 0.5076 (11) | 0.7154 (8) | 0.0293 (4) | 0.107 (2) |
C2A | 0.306 (4) | 0.4820 (11) | 0.8283 (7) | 0.0287 (4) | 0.107 (2) |
C3A | 0.482 (5) | 0.3345 (14) | 0.8721 (11) | 0.0298 (4) | 0.107 (2) |
H3A | 0.5550 | 0.3175 | 0.9459 | 0.036* | 0.107 (2) |
C4A | 0.545 (4) | 0.2165 (11) | 0.8061 (12) | 0.0281 (4) | 0.107 (2) |
C5A | 0.466 (7) | 0.2488 (16) | 0.6878 (12) | 0.0285 (4) | 0.107 (2) |
C6A | 0.305 (7) | 0.3924 (18) | 0.6430 (11) | 0.0299 (4) | 0.107 (2) |
H6A | 0.2532 | 0.4142 | 0.5664 | 0.036* | 0.107 (2) |
C7A | 0.667 (7) | 0.0470 (13) | 0.8583 (16) | 0.0340 (6) | 0.107 (2) |
H7AA | 0.7131 | 0.0459 | 0.9366 | 0.051* | 0.107 (2) |
H7AB | 0.8764 | 0.0167 | 0.8137 | 0.051* | 0.107 (2) |
H7AC | 0.4910 | −0.0325 | 0.8587 | 0.051* | 0.107 (2) |
C8A | 0.549 (18) | 0.115 (4) | 0.618 (2) | 0.0382 (5) | 0.107 (2) |
H8AA | 0.4394 | 0.1434 | 0.5476 | 0.057* | 0.107 (2) |
H8AB | 0.4638 | 0.0097 | 0.6621 | 0.057* | 0.107 (2) |
H8AC | 0.7962 | 0.1053 | 0.5994 | 0.057* | 0.107 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0655 (10) | 0.0482 (9) | 0.0433 (9) | 0.0144 (7) | −0.0138 (7) | −0.0268 (7) |
O2 | 0.0485 (8) | 0.0325 (7) | 0.0430 (9) | 0.0107 (6) | −0.0129 (7) | −0.0096 (6) |
N1 | 0.0403 (9) | 0.0350 (9) | 0.0340 (10) | 0.0049 (7) | −0.0087 (7) | −0.0121 (8) |
N2 | 0.0432 (10) | 0.0373 (9) | 0.0339 (10) | 0.0063 (8) | −0.0092 (8) | −0.0076 (8) |
C1 | 0.0290 (9) | 0.0292 (9) | 0.0288 (11) | 0.0010 (7) | −0.0030 (8) | −0.0086 (8) |
C2 | 0.0280 (8) | 0.0323 (9) | 0.0270 (10) | 0.0000 (7) | −0.0024 (8) | −0.0045 (7) |
C3 | 0.0304 (9) | 0.0349 (10) | 0.0254 (10) | −0.0007 (7) | −0.0038 (8) | −0.0079 (7) |
C4 | 0.0254 (8) | 0.0333 (9) | 0.0276 (9) | −0.0014 (6) | −0.0004 (7) | −0.0091 (7) |
C5 | 0.0253 (8) | 0.0305 (9) | 0.0274 (9) | −0.0001 (7) | −0.0003 (6) | −0.0043 (7) |
C6 | 0.0304 (10) | 0.0359 (11) | 0.0237 (10) | 0.0003 (8) | −0.0047 (7) | −0.0061 (8) |
C7 | 0.0399 (14) | 0.0400 (12) | 0.0371 (10) | 0.0016 (9) | −0.0004 (7) | −0.0159 (9) |
C8 | 0.0325 (12) | 0.0313 (10) | 0.0361 (10) | −0.0007 (9) | −0.0042 (8) | −0.0010 (9) |
O1A | 0.051 (8) | 0.051 (8) | 0.038 (7) | 0.032 (6) | −0.026 (6) | 0.002 (6) |
O2A | 0.0485 (8) | 0.0325 (7) | 0.0430 (9) | 0.0107 (6) | −0.0129 (7) | −0.0096 (6) |
N1A | 0.0432 (10) | 0.0373 (9) | 0.0339 (10) | 0.0063 (8) | −0.0092 (8) | −0.0076 (8) |
N2A | 0.0403 (9) | 0.0350 (9) | 0.0340 (10) | 0.0049 (7) | −0.0087 (7) | −0.0121 (8) |
C1A | 0.0280 (8) | 0.0323 (9) | 0.0270 (10) | 0.0000 (7) | −0.0024 (8) | −0.0045 (7) |
C2A | 0.0290 (9) | 0.0292 (9) | 0.0288 (11) | 0.0010 (7) | −0.0030 (8) | −0.0086 (8) |
C3A | 0.0304 (10) | 0.0359 (11) | 0.0237 (10) | 0.0003 (8) | −0.0047 (7) | −0.0061 (8) |
C4A | 0.0253 (8) | 0.0305 (9) | 0.0274 (9) | −0.0001 (7) | −0.0003 (6) | −0.0043 (7) |
C5A | 0.0254 (8) | 0.0333 (9) | 0.0276 (9) | −0.0014 (6) | −0.0004 (7) | −0.0091 (7) |
C6A | 0.0304 (9) | 0.0349 (10) | 0.0254 (10) | −0.0007 (7) | −0.0038 (8) | −0.0079 (7) |
C7A | 0.0325 (12) | 0.0313 (10) | 0.0361 (10) | −0.0007 (9) | −0.0042 (8) | −0.0010 (9) |
C8A | 0.0399 (14) | 0.0400 (12) | 0.0371 (10) | 0.0016 (9) | −0.0004 (7) | −0.0159 (9) |
O1—N1 | 1.236 (2) | O1A—N1A | 1.236 (2) |
O2—N2 | 1.381 (2) | O2A—N2A | 1.381 (2) |
O2—N1 | 1.456 (2) | O2A—N1A | 1.456 (2) |
N1—C1 | 1.331 (2) | N1A—C1A | 1.331 (3) |
N2—C2 | 1.333 (3) | N2A—C2A | 1.333 (3) |
C1—C6 | 1.414 (2) | C1A—C6A | 1.414 (3) |
C1—C2 | 1.417 (3) | C1A—C2A | 1.418 (3) |
C2—C3 | 1.414 (3) | C2A—C3A | 1.414 (3) |
C3—C4 | 1.367 (3) | C3A—C4A | 1.368 (3) |
C3—H3 | 0.9500 | C3A—H3A | 0.9500 |
C4—C5 | 1.466 (2) | C4A—C5A | 1.467 (2) |
C4—C7 | 1.500 (3) | C4A—C7A | 1.500 (3) |
C5—C6 | 1.363 (3) | C5A—C6A | 1.363 (3) |
C5—C8 | 1.514 (3) | C5A—C8A | 1.514 (3) |
C6—H6 | 0.9500 | C6A—H6A | 0.9500 |
C7—H7A | 0.9800 | C7A—H7AA | 0.9800 |
C7—H7B | 0.9800 | C7A—H7AB | 0.9800 |
C7—H7C | 0.9800 | C7A—H7AC | 0.9800 |
C8—H8A | 0.9800 | C8A—H8AA | 0.9800 |
C8—H8B | 0.9800 | C8A—H8AB | 0.9800 |
C8—H8C | 0.9800 | C8A—H8AC | 0.9800 |
N2—O2—N1 | 109.06 (14) | N2A—O2A—N1A | 109.05 (15) |
O1—N1—C1 | 136.04 (18) | O1A—N1A—C1A | 136.0 (2) |
O1—N1—O2 | 117.78 (15) | O1A—N1A—O2A | 117.77 (18) |
C1—N1—O2 | 106.18 (14) | C1A—N1A—O2A | 106.17 (15) |
C2—N2—O2 | 105.57 (16) | C2A—N2A—O2A | 105.52 (17) |
N1—C1—C6 | 129.90 (17) | N1A—C1A—C6A | 129.92 (19) |
N1—C1—C2 | 107.42 (17) | N1A—C1A—C2A | 107.40 (18) |
C6—C1—C2 | 122.67 (17) | C6A—C1A—C2A | 122.65 (19) |
N2—C2—C3 | 128.95 (17) | N2A—C2A—C3A | 128.9 (2) |
N2—C2—C1 | 111.78 (17) | N2A—C2A—C1A | 111.73 (19) |
C3—C2—C1 | 119.26 (17) | C3A—C2A—C1A | 119.22 (19) |
C4—C3—C2 | 118.83 (16) | C4A—C3A—C2A | 118.75 (18) |
C4—C3—H3 | 120.6 | C4A—C3A—H3A | 120.6 |
C2—C3—H3 | 120.6 | C2A—C3A—H3A | 120.6 |
C3—C4—C5 | 120.97 (17) | C3A—C4A—C5A | 120.85 (19) |
C3—C4—C7 | 119.66 (17) | C3A—C4A—C7A | 119.6 (2) |
C5—C4—C7 | 119.37 (17) | C5A—C4A—C7A | 119.3 (2) |
C6—C5—C4 | 121.02 (17) | C6A—C5A—C4A | 120.98 (19) |
C6—C5—C8 | 120.44 (17) | C6A—C5A—C8A | 120.4 (2) |
C4—C5—C8 | 118.53 (17) | C4A—C5A—C8A | 118.5 (2) |
C5—C6—C1 | 117.25 (16) | C5A—C6A—C1A | 117.24 (18) |
C5—C6—H6 | 121.4 | C5A—C6A—H6A | 121.4 |
C1—C6—H6 | 121.4 | C1A—C6A—H6A | 121.4 |
C4—C7—H7A | 109.5 | C4A—C7A—H7AA | 109.5 |
C4—C7—H7B | 109.5 | C4A—C7A—H7AB | 109.5 |
H7A—C7—H7B | 109.5 | H7AA—C7A—H7AB | 109.5 |
C4—C7—H7C | 109.5 | C4A—C7A—H7AC | 109.5 |
H7A—C7—H7C | 109.5 | H7AA—C7A—H7AC | 109.5 |
H7B—C7—H7C | 109.5 | H7AB—C7A—H7AC | 109.5 |
C5—C8—H8A | 109.5 | C5A—C8A—H8AA | 109.5 |
C5—C8—H8B | 109.5 | C5A—C8A—H8AB | 109.5 |
H8A—C8—H8B | 109.5 | H8AA—C8A—H8AB | 109.5 |
C5—C8—H8C | 109.5 | C5A—C8A—H8AC | 109.5 |
H8A—C8—H8C | 109.5 | H8AA—C8A—H8AC | 109.5 |
H8B—C8—H8C | 109.5 | H8AB—C8A—H8AC | 109.5 |
N2—O2—N1—O1 | 179.62 (16) | N2A—O2A—N1A—O1A | 179.8 (14) |
N2—O2—N1—C1 | 0.4 (2) | N2A—O2A—N1A—C1A | 0.9 (16) |
N1—O2—N2—C2 | −0.6 (2) | N1A—O2A—N2A—C2A | −2.9 (16) |
O1—N1—C1—C6 | 2.3 (4) | O1A—N1A—C1A—C6A | 5 (4) |
O2—N1—C1—C6 | −178.7 (2) | O2A—N1A—C1A—C6A | −177 (2) |
O1—N1—C1—C2 | −179.0 (2) | O1A—N1A—C1A—C2A | −177.2 (19) |
O2—N1—C1—C2 | −0.1 (2) | O2A—N1A—C1A—C2A | 1.3 (17) |
O2—N2—C2—C3 | 179.3 (2) | O2A—N2A—C2A—C3A | 179.4 (18) |
O2—N2—C2—C1 | 0.6 (2) | O2A—N2A—C2A—C1A | 3.8 (17) |
N1—C1—C2—N2 | −0.3 (2) | N1A—C1A—C2A—N2A | −3.4 (18) |
C6—C1—C2—N2 | 178.4 (2) | C6A—C1A—C2A—N2A | 175 (2) |
N1—C1—C2—C3 | −179.2 (2) | N1A—C1A—C2A—C3A | −179.4 (16) |
C6—C1—C2—C3 | −0.4 (3) | C6A—C1A—C2A—C3A | −1 (3) |
N2—C2—C3—C4 | −178.9 (3) | N2A—C2A—C3A—C4A | −178.9 (16) |
C1—C2—C3—C4 | −0.3 (4) | C1A—C2A—C3A—C4A | −4 (2) |
C2—C3—C4—C5 | 0.9 (4) | C2A—C3A—C4A—C5A | 6.5 (18) |
C2—C3—C4—C7 | −179.8 (4) | C2A—C3A—C4A—C7A | −168 (2) |
C3—C4—C5—C6 | −0.8 (4) | C3A—C4A—C5A—C6A | −5 (2) |
C7—C4—C5—C6 | 179.8 (4) | C7A—C4A—C5A—C6A | 170 (3) |
C3—C4—C5—C8 | 178.1 (3) | C3A—C4A—C5A—C8A | 179 (3) |
C7—C4—C5—C8 | −1.2 (4) | C7A—C4A—C5A—C8A | −7 (3) |
C4—C5—C6—C1 | 0.1 (3) | C4A—C5A—C6A—C1A | 0 (3) |
C8—C5—C6—C1 | −178.8 (2) | C8A—C5A—C6A—C1A | 176 (4) |
N1—C1—C6—C5 | 179.0 (2) | N1A—C1A—C6A—C5A | −179 (2) |
C2—C1—C6—C5 | 0.5 (3) | C2A—C1A—C6A—C5A | 3 (3) |
C8H8N2O2 | Z = 4 |
Mr = 164.16 | F(000) = 344 |
Triclinic, P1 | Dx = 1.416 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.3643 (9) Å | Cell parameters from 3327 reflections |
b = 9.0332 (11) Å | θ = 2.8–27.3° |
c = 11.6675 (14) Å | µ = 0.11 mm−1 |
α = 89.264 (2)° | T = 173 K |
β = 83.419 (2)° | Prism, pale yellow |
γ = 87.027 (2)° | 0.35 × 0.30 × 0.25 mm |
V = 769.99 (16) Å3 |
Bruker SMART 1K CCD area-detector diffractometer | 3498 independent reflections |
Radiation source: fine-focus sealed tube | 2286 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ω scans | θmax = 27.5°, θmin = 1.8° |
Absorption correction: multi-scan SADABS; Sheldrick, 2008; Blessing, 1995 | h = −9→9 |
Tmin = 0.96, Tmax = 0.97 | k = −11→11 |
8977 measured reflections | l = 0→15 |
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)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.140 | w = 1/[σ2(Fo2) + (0.071P)2 + 0.076P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
3498 reflections | Δρmax = 0.19 e Å−3 |
304 parameters | Δρmin = −0.15 e Å−3 |
192 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.007 (2) |
C8H8N2O2 | γ = 87.027 (2)° |
Mr = 164.16 | V = 769.99 (16) Å3 |
Triclinic, P1 | Z = 4 |
a = 7.3643 (9) Å | Mo Kα radiation |
b = 9.0332 (11) Å | µ = 0.11 mm−1 |
c = 11.6675 (14) Å | T = 173 K |
α = 89.264 (2)° | 0.35 × 0.30 × 0.25 mm |
β = 83.419 (2)° |
Bruker SMART 1K CCD area-detector diffractometer | 3498 independent reflections |
Absorption correction: multi-scan SADABS; Sheldrick, 2008; Blessing, 1995 | 2286 reflections with I > 2σ(I) |
Tmin = 0.96, Tmax = 0.97 | Rint = 0.024 |
8977 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 192 restraints |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.19 e Å−3 |
3498 reflections | Δρmin = −0.15 e Å−3 |
304 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O11 | 0.8147 (2) | 0.79897 (19) | 0.00576 (14) | 0.0541 (5) | 0.5672 (12) |
O12 | 0.6189 (2) | 0.81070 (16) | 0.17525 (13) | 0.0483 (5) | 0.5672 (12) |
N11 | 0.7192 (3) | 0.7289 (2) | 0.08020 (16) | 0.0391 (5) | 0.5672 (12) |
N12 | 0.5183 (3) | 0.7141 (2) | 0.24628 (17) | 0.0430 (5) | 0.5672 (12) |
C11 | 0.6769 (7) | 0.5874 (3) | 0.0966 (3) | 0.0316 (6) | 0.5672 (12) |
C12 | 0.5557 (7) | 0.5803 (3) | 0.1980 (3) | 0.0316 (6) | 0.5672 (12) |
C13 | 0.4931 (12) | 0.4414 (4) | 0.2386 (5) | 0.0340 (6) | 0.5672 (12) |
H13 | 0.4085 | 0.4348 | 0.3061 | 0.041* | 0.5672 (12) |
C14 | 0.5574 (11) | 0.3164 (4) | 0.1781 (5) | 0.0301 (8) | 0.5672 (12) |
C15 | 0.6857 (11) | 0.3272 (4) | 0.0734 (5) | 0.0290 (9) | 0.5672 (12) |
C16 | 0.7410 (13) | 0.4605 (4) | 0.0320 (6) | 0.0336 (7) | 0.5672 (12) |
H16 | 0.8200 | 0.4681 | −0.0379 | 0.040* | 0.5672 (12) |
C17 | 0.4851 (19) | 0.1680 (5) | 0.2134 (9) | 0.0439 (6) | 0.5672 (12) |
H17A | 0.3956 | 0.1796 | 0.2821 | 0.066* | 0.5672 (12) |
H17B | 0.5865 | 0.1001 | 0.2310 | 0.066* | 0.5672 (12) |
H17C | 0.4261 | 0.1277 | 0.1503 | 0.066* | 0.5672 (12) |
C18 | 0.743 (2) | 0.1895 (5) | 0.0047 (10) | 0.0461 (12) | 0.5672 (12) |
H18A | 0.8344 | 0.2136 | −0.0600 | 0.069* | 0.5672 (12) |
H18B | 0.6365 | 0.1503 | −0.0251 | 0.069* | 0.5672 (12) |
H18C | 0.7970 | 0.1148 | 0.0543 | 0.069* | 0.5672 (12) |
O11A | 0.4893 (3) | 0.8068 (2) | 0.27788 (17) | 0.0566 (7) | 0.4328 (12) |
O12A | 0.6861 (3) | 0.8172 (2) | 0.10931 (17) | 0.0483 (5) | 0.4328 (12) |
N11A | 0.5751 (5) | 0.7360 (2) | 0.1967 (2) | 0.0430 (5) | 0.4328 (12) |
N12A | 0.7688 (4) | 0.7194 (3) | 0.0270 (2) | 0.0391 (5) | 0.4328 (12) |
C11A | 0.5949 (10) | 0.5936 (3) | 0.1654 (4) | 0.0316 (6) | 0.4328 (12) |
C12A | 0.7139 (10) | 0.5854 (3) | 0.0628 (5) | 0.0316 (6) | 0.4328 (12) |
C13A | 0.7539 (18) | 0.4470 (5) | 0.0074 (8) | 0.0336 (7) | 0.4328 (12) |
H13A | 0.8371 | 0.4390 | −0.0611 | 0.040* | 0.4328 (12) |
C14A | 0.6698 (15) | 0.3249 (5) | 0.0548 (7) | 0.0290 (9) | 0.4328 (12) |
C15A | 0.5494 (16) | 0.3363 (4) | 0.1633 (8) | 0.0301 (8) | 0.4328 (12) |
C16A | 0.5133 (17) | 0.4682 (5) | 0.2178 (7) | 0.0340 (6) | 0.4328 (12) |
H16A | 0.4359 | 0.4757 | 0.2886 | 0.041* | 0.4328 (12) |
C17A | 0.719 (3) | 0.1741 (6) | 0.0036 (14) | 0.0461 (12) | 0.4328 (12) |
H17D | 0.7943 | 0.1846 | −0.0705 | 0.069* | 0.4328 (12) |
H17E | 0.6066 | 0.1254 | −0.0083 | 0.069* | 0.4328 (12) |
H17F | 0.7871 | 0.1141 | 0.0564 | 0.069* | 0.4328 (12) |
C18A | 0.482 (3) | 0.1969 (6) | 0.2220 (11) | 0.0439 (6) | 0.4328 (12) |
H18D | 0.4102 | 0.2221 | 0.2958 | 0.066* | 0.4328 (12) |
H18E | 0.5868 | 0.1305 | 0.2358 | 0.066* | 0.4328 (12) |
H18F | 0.4051 | 0.1475 | 0.1726 | 0.066* | 0.4328 (12) |
O21 | −0.0409 (2) | 0.37167 (17) | 0.75642 (13) | 0.0532 (5) | 0.6307 (14) |
O22 | 0.1562 (2) | 0.36192 (15) | 0.58742 (12) | 0.0460 (4) | 0.6307 (14) |
N21 | 0.0502 (3) | 0.4431 (2) | 0.68069 (15) | 0.0378 (5) | 0.6307 (14) |
N22 | 0.2478 (3) | 0.4607 (2) | 0.51346 (16) | 0.0429 (5) | 0.6307 (14) |
C21 | 0.0812 (7) | 0.5863 (3) | 0.6608 (3) | 0.0306 (6) | 0.6307 (14) |
C22 | 0.2011 (6) | 0.5949 (3) | 0.5590 (3) | 0.0316 (5) | 0.6307 (14) |
C23 | 0.2554 (10) | 0.7352 (4) | 0.5161 (5) | 0.0349 (5) | 0.6307 (14) |
H23 | 0.3396 | 0.7430 | 0.4484 | 0.042* | 0.6307 (14) |
C24 | 0.1835 (11) | 0.8597 (3) | 0.5744 (5) | 0.0309 (7) | 0.6307 (14) |
C25 | 0.0575 (12) | 0.8471 (4) | 0.6800 (5) | 0.0307 (8) | 0.6307 (14) |
C26 | 0.0114 (13) | 0.7127 (4) | 0.7240 (6) | 0.0324 (5) | 0.6307 (14) |
H26 | −0.0651 | 0.7041 | 0.7948 | 0.039* | 0.6307 (14) |
C27 | 0.2451 (17) | 1.0103 (4) | 0.5360 (8) | 0.0436 (6) | 0.6307 (14) |
H27A | 0.3358 | 1.0001 | 0.4678 | 0.065* | 0.6307 (14) |
H27B | 0.3001 | 1.0565 | 0.5983 | 0.065* | 0.6307 (14) |
H27C | 0.1397 | 1.0724 | 0.5167 | 0.065* | 0.6307 (14) |
C28 | −0.011 (2) | 0.9852 (4) | 0.7455 (11) | 0.0438 (6) | 0.6307 (14) |
H28A | −0.0993 | 0.9593 | 0.8109 | 0.066* | 0.6307 (14) |
H28B | −0.0696 | 1.0546 | 0.6942 | 0.066* | 0.6307 (14) |
H28C | 0.0927 | 1.0317 | 0.7739 | 0.066* | 0.6307 (14) |
O21A | 0.2898 (4) | 0.3693 (3) | 0.4810 (2) | 0.0553 (9) | 0.3693 (14) |
O22A | 0.0941 (4) | 0.3529 (2) | 0.6496 (2) | 0.0460 (4) | 0.3693 (14) |
N21A | 0.1980 (6) | 0.4378 (3) | 0.5611 (3) | 0.0429 (5) | 0.3693 (14) |
N22A | 0.0035 (5) | 0.4486 (3) | 0.7307 (3) | 0.0378 (5) | 0.3693 (14) |
C21A | 0.1658 (12) | 0.5802 (3) | 0.5904 (5) | 0.0316 (5) | 0.3693 (14) |
C22A | 0.0466 (12) | 0.5848 (4) | 0.6930 (6) | 0.0306 (6) | 0.3693 (14) |
C23A | −0.009 (2) | 0.7231 (5) | 0.7451 (11) | 0.0324 (5) | 0.3693 (14) |
H23A | −0.0942 | 0.7287 | 0.8125 | 0.039* | 0.3693 (14) |
C24A | 0.064 (2) | 0.8489 (5) | 0.6960 (9) | 0.0307 (8) | 0.3693 (14) |
C25A | 0.1889 (19) | 0.8405 (4) | 0.5890 (9) | 0.0309 (7) | 0.3693 (14) |
C26A | 0.2345 (19) | 0.7090 (5) | 0.5356 (8) | 0.0349 (5) | 0.3693 (14) |
H26A | 0.3099 | 0.7040 | 0.4639 | 0.042* | 0.3693 (14) |
C27A | −0.001 (4) | 0.9988 (6) | 0.7434 (19) | 0.0438 (6) | 0.3693 (14) |
H27D | −0.0709 | 0.9869 | 0.8192 | 0.066* | 0.3693 (14) |
H27E | −0.0783 | 1.0494 | 0.6908 | 0.066* | 0.3693 (14) |
H27F | 0.1053 | 1.0579 | 0.7512 | 0.066* | 0.3693 (14) |
C28A | 0.249 (3) | 0.9819 (5) | 0.5302 (13) | 0.0436 (6) | 0.3693 (14) |
H28D | 0.3167 | 0.9589 | 0.4547 | 0.065* | 0.3693 (14) |
H28E | 0.3284 | 1.0319 | 0.5777 | 0.065* | 0.3693 (14) |
H28F | 0.1414 | 1.0470 | 0.5199 | 0.065* | 0.3693 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O11 | 0.0643 (12) | 0.0414 (12) | 0.0560 (11) | −0.0170 (9) | 0.0009 (9) | 0.0123 (9) |
O12 | 0.0594 (13) | 0.0357 (8) | 0.0498 (12) | −0.0037 (8) | −0.0054 (9) | −0.0053 (9) |
N11 | 0.0439 (14) | 0.0415 (10) | 0.0320 (15) | −0.0057 (10) | −0.0036 (11) | 0.0046 (13) |
N12 | 0.0473 (16) | 0.0411 (11) | 0.0398 (17) | −0.0010 (10) | −0.0010 (11) | −0.0066 (12) |
C11 | 0.029 (2) | 0.0335 (9) | 0.032 (3) | −0.0026 (8) | −0.0034 (14) | 0.0020 (10) |
C12 | 0.034 (2) | 0.0318 (10) | 0.029 (2) | −0.0002 (9) | −0.0029 (13) | −0.0019 (11) |
C13 | 0.0373 (19) | 0.0417 (15) | 0.022 (2) | 0.0021 (15) | −0.0011 (12) | 0.0040 (15) |
C14 | 0.0319 (9) | 0.0315 (11) | 0.0282 (16) | 0.0038 (12) | −0.0128 (12) | 0.0095 (11) |
C15 | 0.0301 (13) | 0.0369 (8) | 0.0227 (18) | 0.0014 (6) | −0.0153 (15) | −0.0039 (7) |
C16 | 0.0346 (13) | 0.0444 (11) | 0.021 (3) | −0.0025 (11) | −0.0018 (16) | −0.0013 (9) |
C17 | 0.0433 (9) | 0.0352 (16) | 0.0542 (15) | −0.005 (3) | −0.0088 (11) | 0.0070 (17) |
C18 | 0.047 (3) | 0.0397 (12) | 0.0521 (9) | 0.0028 (13) | −0.0082 (17) | −0.0139 (13) |
O11A | 0.0798 (18) | 0.0387 (15) | 0.0487 (15) | 0.0064 (13) | 0.0016 (13) | −0.0160 (12) |
O12A | 0.0594 (13) | 0.0357 (8) | 0.0498 (12) | −0.0037 (8) | −0.0054 (9) | −0.0053 (9) |
N11A | 0.0473 (16) | 0.0411 (11) | 0.0398 (17) | −0.0010 (10) | −0.0010 (11) | −0.0066 (12) |
N12A | 0.0439 (14) | 0.0415 (10) | 0.0320 (15) | −0.0057 (10) | −0.0036 (11) | 0.0046 (13) |
C11A | 0.034 (2) | 0.0318 (10) | 0.029 (2) | −0.0002 (9) | −0.0029 (13) | −0.0019 (11) |
C12A | 0.029 (2) | 0.0335 (9) | 0.032 (3) | −0.0026 (8) | −0.0034 (14) | 0.0020 (10) |
C13A | 0.0346 (13) | 0.0444 (11) | 0.021 (3) | −0.0025 (11) | −0.0018 (16) | −0.0013 (9) |
C14A | 0.0301 (13) | 0.0369 (8) | 0.0227 (18) | 0.0014 (6) | −0.0153 (15) | −0.0039 (7) |
C15A | 0.0319 (9) | 0.0315 (11) | 0.0282 (16) | 0.0038 (12) | −0.0128 (12) | 0.0095 (11) |
C16A | 0.0373 (19) | 0.0417 (15) | 0.022 (2) | 0.0021 (15) | −0.0011 (12) | 0.0040 (15) |
C17A | 0.047 (3) | 0.0397 (12) | 0.0521 (9) | 0.0028 (13) | −0.0082 (17) | −0.0139 (13) |
C18A | 0.0433 (9) | 0.0352 (16) | 0.0542 (15) | −0.005 (3) | −0.0088 (11) | 0.0070 (17) |
O21 | 0.0670 (11) | 0.0369 (10) | 0.0545 (10) | −0.0137 (8) | 0.0024 (8) | 0.0118 (8) |
O22 | 0.0565 (12) | 0.0331 (7) | 0.0482 (12) | 0.0032 (7) | −0.0062 (9) | −0.0073 (9) |
N21 | 0.0438 (13) | 0.0352 (9) | 0.0345 (14) | −0.0012 (9) | −0.0056 (10) | 0.0008 (12) |
N22 | 0.0472 (15) | 0.0391 (11) | 0.0410 (16) | 0.0036 (9) | −0.0014 (11) | −0.0076 (11) |
C21 | 0.031 (2) | 0.0303 (8) | 0.030 (2) | 0.0000 (7) | −0.0038 (12) | 0.0007 (9) |
C22 | 0.033 (2) | 0.0321 (9) | 0.029 (2) | 0.0017 (8) | −0.0033 (11) | −0.0021 (9) |
C23 | 0.0352 (18) | 0.0410 (13) | 0.0272 (19) | −0.0003 (14) | 0.0006 (11) | 0.0011 (12) |
C24 | 0.0330 (8) | 0.0314 (10) | 0.0290 (15) | 0.0035 (11) | −0.0095 (12) | 0.0066 (10) |
C25 | 0.0322 (9) | 0.0327 (7) | 0.0288 (17) | 0.0010 (5) | −0.0107 (14) | −0.0042 (6) |
C26 | 0.031 (2) | 0.0384 (9) | 0.027 (2) | 0.0004 (10) | 0.0000 (12) | −0.0023 (8) |
C27 | 0.0439 (10) | 0.0337 (14) | 0.0538 (11) | −0.004 (2) | −0.0073 (9) | 0.0058 (16) |
C28 | 0.0439 (17) | 0.0363 (10) | 0.0512 (10) | 0.0012 (13) | −0.0052 (9) | −0.0114 (13) |
O21A | 0.073 (2) | 0.0406 (18) | 0.0487 (17) | 0.0097 (15) | 0.0035 (15) | −0.0176 (14) |
O22A | 0.0565 (12) | 0.0331 (7) | 0.0482 (12) | 0.0032 (7) | −0.0062 (9) | −0.0073 (9) |
N21A | 0.0472 (15) | 0.0391 (11) | 0.0410 (16) | 0.0036 (9) | −0.0014 (11) | −0.0076 (11) |
N22A | 0.0438 (13) | 0.0352 (9) | 0.0345 (14) | −0.0012 (9) | −0.0056 (10) | 0.0008 (12) |
C21A | 0.033 (2) | 0.0321 (9) | 0.029 (2) | 0.0017 (8) | −0.0033 (11) | −0.0021 (9) |
C22A | 0.031 (2) | 0.0303 (8) | 0.030 (2) | 0.0000 (7) | −0.0038 (12) | 0.0007 (9) |
C23A | 0.031 (2) | 0.0384 (9) | 0.027 (2) | 0.0004 (10) | 0.0000 (12) | −0.0023 (8) |
C24A | 0.0322 (9) | 0.0327 (7) | 0.0288 (17) | 0.0010 (5) | −0.0107 (14) | −0.0042 (6) |
C25A | 0.0330 (8) | 0.0314 (10) | 0.0290 (15) | 0.0035 (11) | −0.0095 (12) | 0.0066 (10) |
C26A | 0.0352 (18) | 0.0410 (13) | 0.0272 (19) | −0.0003 (14) | 0.0006 (11) | 0.0011 (12) |
C27A | 0.0439 (17) | 0.0363 (10) | 0.0512 (10) | 0.0012 (13) | −0.0052 (9) | −0.0114 (13) |
C28A | 0.0439 (10) | 0.0337 (14) | 0.0538 (11) | −0.004 (2) | −0.0073 (9) | 0.0058 (16) |
O11—N11 | 1.2416 (18) | O21—N21 | 1.2415 (18) |
O12—N12 | 1.3801 (18) | O22—N22 | 1.3802 (18) |
O12—N11 | 1.4484 (17) | O22—N21 | 1.4482 (17) |
N11—C11 | 1.338 (3) | N21—C21 | 1.338 (3) |
N12—C12 | 1.342 (3) | N22—C22 | 1.342 (3) |
C11—C12 | 1.4008 (19) | C21—C22 | 1.4006 (19) |
C11—C16 | 1.409 (3) | C21—C26 | 1.409 (3) |
C12—C13 | 1.417 (3) | C22—C23 | 1.417 (3) |
C13—C14 | 1.373 (4) | C23—C24 | 1.373 (4) |
C13—H13 | 0.9500 | C23—H23 | 0.9500 |
C14—C15 | 1.4615 (15) | C24—C25 | 1.4616 (15) |
C14—C17 | 1.503 (5) | C24—C27 | 1.503 (5) |
C15—C16 | 1.357 (4) | C25—C26 | 1.356 (4) |
C15—C18 | 1.505 (4) | C25—C28 | 1.505 (4) |
C16—H16 | 0.9500 | C26—H26 | 0.9500 |
C17—H17A | 0.9800 | C27—H27A | 0.9800 |
C17—H17B | 0.9800 | C27—H27B | 0.9800 |
C17—H17C | 0.9800 | C27—H27C | 0.9800 |
C18—H18A | 0.9800 | C28—H28A | 0.9800 |
C18—H18B | 0.9800 | C28—H28B | 0.9800 |
C18—H18C | 0.9800 | C28—H28C | 0.9800 |
O11A—N11A | 1.2415 (19) | O21A—N21A | 1.2415 (19) |
O12A—N12A | 1.3801 (18) | O22A—N22A | 1.3801 (18) |
O12A—N11A | 1.4485 (18) | O22A—N21A | 1.4486 (18) |
N11A—C11A | 1.338 (3) | N21A—C21A | 1.337 (3) |
N12A—C12A | 1.342 (3) | N22A—C22A | 1.342 (3) |
C11A—C12A | 1.4008 (19) | C21A—C22A | 1.4008 (19) |
C11A—C16A | 1.409 (3) | C21A—C26A | 1.409 (3) |
C12A—C13A | 1.417 (3) | C22A—C23A | 1.417 (3) |
C13A—C14A | 1.373 (4) | C23A—C24A | 1.373 (4) |
C13A—H13A | 0.9500 | C23A—H23A | 0.9500 |
C14A—C15A | 1.4620 (15) | C24A—C25A | 1.4621 (16) |
C14A—C17A | 1.504 (5) | C24A—C27A | 1.504 (5) |
C15A—C16A | 1.356 (4) | C25A—C26A | 1.357 (4) |
C15A—C18A | 1.505 (4) | C25A—C28A | 1.505 (4) |
C16A—H16A | 0.9500 | C26A—H26A | 0.9500 |
C17A—H17D | 0.9800 | C27A—H27D | 0.9800 |
C17A—H17E | 0.9800 | C27A—H27E | 0.9800 |
C17A—H17F | 0.9800 | C27A—H27F | 0.9800 |
C18A—H18D | 0.9800 | C28A—H28D | 0.9800 |
C18A—H18E | 0.9800 | C28A—H28E | 0.9800 |
C18A—H18F | 0.9800 | C28A—H28F | 0.9800 |
N12—O12—N11 | 109.19 (12) | N22—O22—N21 | 109.16 (11) |
O11—N11—C11 | 135.69 (17) | O21—N21—C21 | 135.65 (17) |
O11—N11—O12 | 118.15 (14) | O21—N21—O22 | 118.19 (13) |
C11—N11—O12 | 106.13 (14) | C21—N21—O22 | 106.15 (14) |
C12—N12—O12 | 105.19 (14) | C22—N22—O22 | 105.21 (14) |
N11—C11—C12 | 107.5 (2) | N21—C21—C22 | 107.5 (2) |
N11—C11—C16 | 129.9 (2) | N21—C21—C26 | 129.9 (2) |
C12—C11—C16 | 122.6 (3) | C22—C21—C26 | 122.6 (3) |
N12—C12—C11 | 112.0 (2) | N22—C22—C21 | 112.0 (2) |
N12—C12—C13 | 128.35 (19) | N22—C22—C23 | 128.38 (19) |
C11—C12—C13 | 119.7 (3) | C21—C22—C23 | 119.6 (3) |
C14—C13—C12 | 118.5 (2) | C24—C23—C22 | 118.5 (2) |
C14—C13—H13 | 120.8 | C24—C23—H23 | 120.8 |
C12—C13—H13 | 120.8 | C22—C23—H23 | 120.8 |
C13—C14—C15 | 120.6 (3) | C23—C24—C25 | 120.6 (3) |
C13—C14—C17 | 120.3 (3) | C23—C24—C27 | 120.3 (3) |
C15—C14—C17 | 119.0 (3) | C25—C24—C27 | 119.0 (3) |
C16—C15—C14 | 121.1 (3) | C26—C25—C24 | 121.1 (3) |
C16—C15—C18 | 119.4 (3) | C26—C25—C28 | 119.5 (3) |
C14—C15—C18 | 119.2 (3) | C24—C25—C28 | 119.2 (3) |
C15—C16—C11 | 117.6 (2) | C25—C26—C21 | 117.5 (2) |
C15—C16—H16 | 121.2 | C25—C26—H26 | 121.2 |
C11—C16—H16 | 121.2 | C21—C26—H26 | 121.2 |
C14—C17—H17A | 109.5 | C24—C27—H27A | 109.5 |
C14—C17—H17B | 109.5 | C24—C27—H27B | 109.5 |
H17A—C17—H17B | 109.5 | H27A—C27—H27B | 109.5 |
C14—C17—H17C | 109.5 | C24—C27—H27C | 109.5 |
H17A—C17—H17C | 109.5 | H27A—C27—H27C | 109.5 |
H17B—C17—H17C | 109.5 | H27B—C27—H27C | 109.5 |
C15—C18—H18A | 109.5 | C25—C28—H28A | 109.5 |
C15—C18—H18B | 109.5 | C25—C28—H28B | 109.5 |
H18A—C18—H18B | 109.5 | H28A—C28—H28B | 109.5 |
C15—C18—H18C | 109.5 | C25—C28—H28C | 109.5 |
H18A—C18—H18C | 109.5 | H28A—C28—H28C | 109.5 |
H18B—C18—H18C | 109.5 | H28B—C28—H28C | 109.5 |
N12A—O12A—N11A | 109.18 (12) | N22A—O22A—N21A | 109.18 (12) |
O11A—N11A—C11A | 135.74 (18) | O21A—N21A—C21A | 135.78 (18) |
O11A—N11A—O12A | 118.12 (14) | O21A—N21A—O22A | 118.08 (14) |
C11A—N11A—O12A | 106.14 (14) | C21A—N21A—O22A | 106.13 (14) |
C12A—N12A—O12A | 105.19 (14) | C22A—N22A—O22A | 105.18 (14) |
N11A—C11A—C12A | 107.5 (2) | N21A—C21A—C22A | 107.5 (2) |
N11A—C11A—C16A | 129.9 (2) | N21A—C21A—C26A | 129.9 (2) |
C12A—C11A—C16A | 122.6 (3) | C22A—C21A—C26A | 122.5 (3) |
N12A—C12A—C11A | 112.0 (2) | N22A—C22A—C21A | 112.0 (2) |
N12A—C12A—C13A | 128.3 (2) | N22A—C22A—C23A | 128.4 (2) |
C11A—C12A—C13A | 119.6 (3) | C21A—C22A—C23A | 119.6 (3) |
C14A—C13A—C12A | 118.5 (2) | C24A—C23A—C22A | 118.5 (2) |
C14A—C13A—H13A | 120.8 | C24A—C23A—H23A | 120.8 |
C12A—C13A—H13A | 120.8 | C22A—C23A—H23A | 120.8 |
C13A—C14A—C15A | 120.5 (3) | C23A—C24A—C25A | 120.5 (3) |
C13A—C14A—C17A | 120.1 (3) | C23A—C24A—C27A | 120.2 (3) |
C15A—C14A—C17A | 118.9 (3) | C25A—C24A—C27A | 118.9 (3) |
C16A—C15A—C14A | 121.1 (3) | C26A—C25A—C24A | 121.1 (3) |
C16A—C15A—C18A | 119.4 (3) | C26A—C25A—C28A | 119.4 (3) |
C14A—C15A—C18A | 119.1 (3) | C24A—C25A—C28A | 119.1 (3) |
C15A—C16A—C11A | 117.6 (2) | C25A—C26A—C21A | 117.6 (2) |
C15A—C16A—H16A | 121.2 | C25A—C26A—H26A | 121.2 |
C11A—C16A—H16A | 121.2 | C21A—C26A—H26A | 121.2 |
C14A—C17A—H17D | 109.5 | C24A—C27A—H27D | 109.5 |
C14A—C17A—H17E | 109.5 | C24A—C27A—H27E | 109.5 |
H17D—C17A—H17E | 109.5 | H27D—C27A—H27E | 109.5 |
C14A—C17A—H17F | 109.5 | C24A—C27A—H27F | 109.5 |
H17D—C17A—H17F | 109.5 | H27D—C27A—H27F | 109.5 |
H17E—C17A—H17F | 109.5 | H27E—C27A—H27F | 109.5 |
C15A—C18A—H18D | 109.5 | C25A—C28A—H28D | 109.5 |
C15A—C18A—H18E | 109.5 | C25A—C28A—H28E | 109.5 |
H18D—C18A—H18E | 109.5 | H28D—C28A—H28E | 109.5 |
C15A—C18A—H18F | 109.5 | C25A—C28A—H28F | 109.5 |
H18D—C18A—H18F | 109.5 | H28D—C28A—H28F | 109.5 |
H18E—C18A—H18F | 109.5 | H28E—C28A—H28F | 109.5 |
N12—O12—N11—O11 | 178.5 (2) | N22—O22—N21—O21 | −179.6 (2) |
N12—O12—N11—C11 | −0.1 (4) | N22—O22—N21—C21 | −0.3 (4) |
N11—O12—N12—C12 | 0.4 (4) | N21—O22—N22—C22 | 0.2 (3) |
O11—N11—C11—C12 | −178.4 (4) | O21—N21—C21—C22 | 179.3 (4) |
O12—N11—C11—C12 | −0.2 (5) | O22—N21—C21—C22 | 0.2 (5) |
O11—N11—C11—C16 | 4.3 (10) | O21—N21—C21—C26 | −1.5 (10) |
O12—N11—C11—C16 | −177.6 (7) | O22—N21—C21—C26 | 179.4 (7) |
O12—N12—C12—C11 | −0.6 (6) | O22—N22—C22—C21 | −0.1 (5) |
O12—N12—C12—C13 | 177.5 (8) | O22—N22—C22—C23 | −179.0 (6) |
N11—C11—C12—N12 | 0.5 (7) | N21—C21—C22—N22 | −0.1 (6) |
C16—C11—C12—N12 | 178.1 (7) | C26—C21—C22—N22 | −179.4 (7) |
N11—C11—C12—C13 | −177.8 (7) | N21—C21—C22—C23 | 178.9 (6) |
C16—C11—C12—C13 | −0.2 (10) | C26—C21—C22—C23 | −0.3 (9) |
N12—C12—C13—C14 | −176.4 (7) | N22—C22—C23—C24 | 176.9 (6) |
C11—C12—C13—C14 | 1.6 (12) | C21—C22—C23—C24 | −2.0 (10) |
C12—C13—C14—C15 | −0.8 (12) | C22—C23—C24—C25 | 1.5 (10) |
C12—C13—C14—C17 | −175.9 (9) | C22—C23—C24—C27 | 176.6 (8) |
C13—C14—C15—C16 | −1.6 (10) | C23—C24—C25—C26 | 1.4 (9) |
C17—C14—C15—C16 | 173.6 (10) | C27—C24—C25—C26 | −173.8 (9) |
C13—C14—C15—C18 | −175.8 (11) | C23—C24—C25—C28 | 176.6 (10) |
C17—C14—C15—C18 | −0.6 (9) | C27—C24—C25—C28 | 1.5 (9) |
C14—C15—C16—C11 | 2.9 (11) | C24—C25—C26—C21 | −3.5 (11) |
C18—C15—C16—C11 | 177.2 (10) | C28—C25—C26—C21 | −178.8 (9) |
N11—C11—C16—C15 | 174.9 (7) | N21—C21—C26—C25 | −176.0 (7) |
C12—C11—C16—C15 | −2.1 (12) | C22—C21—C26—C25 | 3.1 (11) |
N12A—O12A—N11A—O11A | −179.7 (3) | N22A—O22A—N21A—O21A | 179.5 (4) |
N12A—O12A—N11A—C11A | 0.4 (6) | N22A—O22A—N21A—C21A | −0.6 (7) |
N11A—O12A—N12A—C12A | −0.9 (6) | N21A—O22A—N22A—C22A | 1.0 (7) |
O11A—N11A—C11A—C12A | −179.7 (6) | O21A—N21A—C21A—C22A | 179.8 (8) |
O12A—N11A—C11A—C12A | 0.2 (8) | O22A—N21A—C21A—C22A | 0.0 (10) |
O11A—N11A—C11A—C16A | 2.1 (16) | O21A—N21A—C21A—C26A | −1.3 (18) |
O12A—N11A—C11A—C16A | −178.0 (11) | O22A—N21A—C21A—C26A | 178.8 (12) |
O12A—N12A—C12A—C11A | 1.0 (8) | O22A—N22A—C22A—C21A | −1.1 (10) |
O12A—N12A—C12A—C13A | 177.4 (10) | O22A—N22A—C22A—C23A | −179.1 (13) |
N11A—C11A—C12A—N12A | −0.8 (10) | N21A—C21A—C22A—N22A | 0.7 (12) |
C16A—C11A—C12A—N12A | 177.6 (10) | C26A—C21A—C22A—N22A | −178.3 (11) |
N11A—C11A—C12A—C13A | −177.5 (9) | N21A—C21A—C22A—C23A | 178.9 (12) |
C16A—C11A—C12A—C13A | 0.8 (14) | C26A—C21A—C22A—C23A | 0.0 (18) |
N12A—C12A—C13A—C14A | −174.3 (10) | N22A—C22A—C23A—C24A | 174.6 (13) |
C11A—C12A—C13A—C14A | 1.8 (16) | C21A—C22A—C23A—C24A | −3 (2) |
C12A—C13A—C14A—C15A | −3.2 (16) | C22A—C23A—C24A—C25A | 3 (2) |
C12A—C13A—C14A—C17A | −175.5 (13) | C22A—C23A—C24A—C27A | 175.5 (17) |
C13A—C14A—C15A—C16A | 2.1 (13) | C23A—C24A—C25A—C26A | 0.3 (16) |
C17A—C14A—C15A—C16A | 174.5 (15) | C27A—C24A—C25A—C26A | −172.2 (18) |
C13A—C14A—C15A—C18A | −170.9 (14) | C23A—C24A—C25A—C28A | 172.9 (17) |
C17A—C14A—C15A—C18A | 1.5 (13) | C27A—C24A—C25A—C28A | 0.4 (15) |
C14A—C15A—C16A—C11A | 0.5 (16) | C24A—C25A—C26A—C21A | −3.5 (18) |
C18A—C15A—C16A—C11A | 173.5 (13) | C28A—C25A—C26A—C21A | −176.1 (15) |
N11A—C11A—C16A—C15A | 176.0 (10) | N21A—C21A—C26A—C25A | −175.3 (12) |
C12A—C11A—C16A—C15A | −2.0 (17) | C22A—C21A—C26A—C25A | 3.4 (19) |
C8H8N2O2 | Z = 6 |
Mr = 164.16 | F(000) = 516 |
Triclinic, P1 | Dx = 1.417 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.0070 (11) Å | Cell parameters from 2306 reflections |
b = 11.1331 (13) Å | θ = 2.3–27.2° |
c = 12.9526 (15) Å | µ = 0.11 mm−1 |
α = 65.173 (2)° | T = 173 K |
β = 80.629 (2)° | Prism, pale yellow |
γ = 79.862 (2)° | 0.35 × 0.25 × 0.20 mm |
V = 1154.6 (2) Å3 |
Bruker SMART 1K CCD area-detector diffractometer | 5157 independent reflections |
Radiation source: fine-focus sealed tube | 3457 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
ω scans | θmax = 27.5°, θmin = 1.7° |
Absorption correction: multi-scan SADABS: Sheldrick, 2008; Blessing, 1995 | h = −11→11 |
Tmin = 0.96, Tmax = 0.98 | k = −14→14 |
13249 measured reflections | l = −16→16 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.168 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.105P)2 + 0.077P] where P = (Fo2 + 2Fc2)/3 |
5157 reflections | (Δ/σ)max = 0.001 |
454 parameters | Δρmax = 0.40 e Å−3 |
480 restraints | Δρmin = −0.23 e Å−3 |
C8H8N2O2 | γ = 79.862 (2)° |
Mr = 164.16 | V = 1154.6 (2) Å3 |
Triclinic, P1 | Z = 6 |
a = 9.0070 (11) Å | Mo Kα radiation |
b = 11.1331 (13) Å | µ = 0.11 mm−1 |
c = 12.9526 (15) Å | T = 173 K |
α = 65.173 (2)° | 0.35 × 0.25 × 0.20 mm |
β = 80.629 (2)° |
Bruker SMART 1K CCD area-detector diffractometer | 5157 independent reflections |
Absorption correction: multi-scan SADABS: Sheldrick, 2008; Blessing, 1995 | 3457 reflections with I > 2σ(I) |
Tmin = 0.96, Tmax = 0.98 | Rint = 0.020 |
13249 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 480 restraints |
wR(F2) = 0.168 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.40 e Å−3 |
5157 reflections | Δρmin = −0.23 e Å−3 |
454 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O11 | 0.29681 (13) | 0.36876 (12) | 0.09403 (9) | 0.0475 (4) | 0.7656 (15) |
O12 | 0.28001 (11) | 0.20357 (11) | 0.27648 (9) | 0.0399 (3) | 0.7656 (15) |
N11 | 0.36324 (14) | 0.29627 (13) | 0.17970 (11) | 0.0342 (3) | 0.7656 (15) |
N12 | 0.37472 (15) | 0.13351 (14) | 0.36181 (11) | 0.0381 (4) | 0.7656 (15) |
C11 | 0.50350 (19) | 0.2803 (2) | 0.20875 (15) | 0.0291 (4) | 0.7656 (15) |
C12 | 0.50815 (18) | 0.1806 (2) | 0.31977 (14) | 0.0299 (4) | 0.7656 (15) |
C13 | 0.6449 (2) | 0.1425 (4) | 0.3723 (2) | 0.0326 (4) | 0.7656 (15) |
H13 | 0.6500 | 0.0761 | 0.4480 | 0.039* | 0.7656 (15) |
C14 | 0.7699 (2) | 0.2038 (4) | 0.3114 (3) | 0.0300 (4) | 0.7656 (15) |
C15 | 0.7615 (3) | 0.3079 (5) | 0.1958 (3) | 0.0305 (3) | 0.7656 (15) |
C16 | 0.6303 (3) | 0.3459 (4) | 0.1451 (3) | 0.0312 (4) | 0.7656 (15) |
H16 | 0.6242 | 0.4136 | 0.0701 | 0.037* | 0.7656 (15) |
C17 | 0.9165 (3) | 0.1668 (5) | 0.3641 (3) | 0.0394 (4) | 0.7656 (15) |
H17A | 0.9040 | 0.0971 | 0.4415 | 0.059* | 0.7656 (15) |
H17B | 0.9460 | 0.2455 | 0.3678 | 0.059* | 0.7656 (15) |
H17C | 0.9955 | 0.1338 | 0.3175 | 0.059* | 0.7656 (15) |
C18 | 0.9017 (3) | 0.3718 (5) | 0.1310 (3) | 0.0405 (7) | 0.7656 (15) |
H18A | 0.8781 | 0.4382 | 0.0552 | 0.061* | 0.7656 (15) |
H18B | 0.9816 | 0.3033 | 0.1228 | 0.061* | 0.7656 (15) |
H18C | 0.9366 | 0.4153 | 0.1730 | 0.061* | 0.7656 (15) |
O11A | 0.2817 (4) | 0.1009 (4) | 0.3965 (3) | 0.0479 (12) | 0.2344 (15) |
O12A | 0.2736 (3) | 0.2663 (4) | 0.2144 (3) | 0.0399 (3) | 0.2344 (15) |
N11A | 0.3524 (3) | 0.1810 (5) | 0.3130 (3) | 0.0381 (4) | 0.2344 (15) |
N12A | 0.3724 (4) | 0.3474 (4) | 0.1323 (3) | 0.0342 (3) | 0.2344 (15) |
C11A | 0.4947 (4) | 0.2116 (8) | 0.2880 (5) | 0.0299 (4) | 0.2344 (15) |
C12A | 0.5049 (5) | 0.3121 (8) | 0.1773 (5) | 0.0291 (4) | 0.2344 (15) |
C13A | 0.6430 (8) | 0.3676 (14) | 0.1302 (9) | 0.0312 (4) | 0.2344 (15) |
H13A | 0.6509 | 0.4385 | 0.0566 | 0.037* | 0.2344 (15) |
C14A | 0.7650 (8) | 0.3163 (15) | 0.1935 (10) | 0.0305 (3) | 0.2344 (15) |
C15A | 0.7507 (6) | 0.2120 (13) | 0.3092 (9) | 0.0300 (4) | 0.2344 (15) |
C16A | 0.6187 (7) | 0.1577 (13) | 0.3548 (7) | 0.0326 (4) | 0.2344 (15) |
H16A | 0.6103 | 0.0867 | 0.4282 | 0.039* | 0.2344 (15) |
C17A | 0.9118 (10) | 0.3749 (19) | 0.1481 (10) | 0.0405 (7) | 0.2344 (15) |
H17D | 0.9024 | 0.4461 | 0.0717 | 0.061* | 0.2344 (15) |
H17E | 0.9928 | 0.3053 | 0.1437 | 0.061* | 0.2344 (15) |
H17F | 0.9363 | 0.4115 | 0.1993 | 0.061* | 0.2344 (15) |
C18A | 0.8889 (9) | 0.1544 (19) | 0.3742 (11) | 0.0394 (4) | 0.2344 (15) |
H18D | 0.8624 | 0.0827 | 0.4480 | 0.059* | 0.2344 (15) |
H18E | 0.9256 | 0.2245 | 0.3869 | 0.059* | 0.2344 (15) |
H18F | 0.9686 | 0.1187 | 0.3298 | 0.059* | 0.2344 (15) |
O21 | 0.8196 (2) | 0.47227 (18) | 0.40535 (13) | 0.0513 (6) | 0.5019 (11) |
O22 | 0.83630 (17) | 0.63697 (18) | 0.22268 (13) | 0.0448 (4) | 0.5019 (11) |
N21 | 0.7532 (2) | 0.5444 (2) | 0.31958 (15) | 0.0380 (5) | 0.5019 (11) |
N22 | 0.7425 (2) | 0.7046 (2) | 0.13634 (15) | 0.0384 (5) | 0.5019 (11) |
C21 | 0.6130 (3) | 0.5600 (5) | 0.2905 (3) | 0.0288 (6) | 0.5019 (11) |
C22 | 0.6089 (3) | 0.6580 (5) | 0.1788 (3) | 0.0287 (5) | 0.5019 (11) |
C23 | 0.4727 (5) | 0.6945 (10) | 0.1257 (5) | 0.0319 (5) | 0.5019 (11) |
H23 | 0.4687 | 0.7579 | 0.0489 | 0.038* | 0.5019 (11) |
C24 | 0.3465 (5) | 0.6360 (11) | 0.1880 (6) | 0.0290 (8) | 0.5019 (11) |
C25 | 0.3531 (4) | 0.5368 (9) | 0.3056 (5) | 0.0276 (10) | 0.5019 (11) |
C26 | 0.4850 (4) | 0.4974 (9) | 0.3557 (5) | 0.0311 (9) | 0.5019 (11) |
H26 | 0.4908 | 0.4307 | 0.4311 | 0.037* | 0.5019 (11) |
C27 | 0.2017 (7) | 0.6684 (15) | 0.1337 (7) | 0.0404 (5) | 0.5019 (11) |
H27A | 0.2144 | 0.7371 | 0.0558 | 0.061* | 0.5019 (11) |
H27B | 0.1201 | 0.7013 | 0.1787 | 0.061* | 0.5019 (11) |
H27C | 0.1759 | 0.5879 | 0.1309 | 0.061* | 0.5019 (11) |
C28 | 0.2148 (7) | 0.4686 (16) | 0.3689 (8) | 0.0427 (12) | 0.5019 (11) |
H28A | 0.2377 | 0.4044 | 0.4456 | 0.064* | 0.5019 (11) |
H28B | 0.1859 | 0.4219 | 0.3271 | 0.064* | 0.5019 (11) |
H28C | 0.1310 | 0.5354 | 0.3749 | 0.064* | 0.5019 (11) |
O21A | 0.83450 (19) | 0.73783 (18) | 0.10587 (14) | 0.0529 (6) | 0.4981 (11) |
O22A | 0.84203 (18) | 0.57317 (18) | 0.28831 (13) | 0.0448 (4) | 0.4981 (11) |
N21A | 0.7639 (2) | 0.6573 (2) | 0.18902 (16) | 0.0384 (5) | 0.4981 (11) |
N22A | 0.7429 (2) | 0.4925 (2) | 0.37047 (15) | 0.0380 (5) | 0.4981 (11) |
C21A | 0.6224 (3) | 0.6248 (5) | 0.2130 (3) | 0.0287 (5) | 0.4981 (11) |
C22A | 0.6120 (3) | 0.5245 (5) | 0.3238 (3) | 0.0288 (6) | 0.4981 (11) |
C23A | 0.4741 (5) | 0.4686 (9) | 0.3705 (5) | 0.0311 (9) | 0.4981 (11) |
H23A | 0.4648 | 0.4004 | 0.4454 | 0.037* | 0.4981 (11) |
C24A | 0.3543 (5) | 0.5154 (9) | 0.3050 (5) | 0.0276 (10) | 0.4981 (11) |
C25A | 0.3673 (5) | 0.6225 (11) | 0.1907 (6) | 0.0290 (8) | 0.4981 (11) |
C26A | 0.4991 (5) | 0.6772 (10) | 0.1454 (5) | 0.0319 (5) | 0.4981 (11) |
H26A | 0.5079 | 0.7476 | 0.0715 | 0.038* | 0.4981 (11) |
C27A | 0.2033 (7) | 0.4658 (16) | 0.3546 (8) | 0.0427 (12) | 0.4981 (11) |
H27D | 0.2123 | 0.3952 | 0.4314 | 0.064* | 0.4981 (11) |
H27E | 0.1702 | 0.4303 | 0.3057 | 0.064* | 0.4981 (11) |
H27F | 0.1289 | 0.5395 | 0.3593 | 0.064* | 0.4981 (11) |
C28A | 0.2297 (7) | 0.6787 (15) | 0.1250 (8) | 0.0404 (5) | 0.4981 (11) |
H28D | 0.2569 | 0.7486 | 0.0503 | 0.061* | 0.4981 (11) |
H28E | 0.1500 | 0.7166 | 0.1679 | 0.061* | 0.4981 (11) |
H28F | 0.1926 | 0.6074 | 0.1144 | 0.061* | 0.4981 (11) |
O31 | 0.59509 (17) | 0.78582 (16) | 0.39978 (12) | 0.0485 (5) | 0.5661 (12) |
O32 | 0.60990 (15) | 0.94967 (16) | 0.21663 (12) | 0.0426 (4) | 0.5661 (12) |
N31 | 0.52650 (18) | 0.86047 (19) | 0.31575 (14) | 0.0345 (4) | 0.5661 (12) |
N32 | 0.5128 (2) | 1.0219 (2) | 0.13329 (14) | 0.0386 (5) | 0.5661 (12) |
C31 | 0.3837 (3) | 0.8808 (5) | 0.2902 (3) | 0.0276 (5) | 0.5661 (12) |
C32 | 0.3777 (2) | 0.9798 (5) | 0.1790 (3) | 0.0278 (5) | 0.5661 (12) |
C33 | 0.2378 (4) | 1.0232 (9) | 0.1302 (4) | 0.0325 (5) | 0.5661 (12) |
H33 | 0.2321 | 1.0877 | 0.0540 | 0.039* | 0.5661 (12) |
C34 | 0.1107 (3) | 0.9697 (8) | 0.1959 (5) | 0.0279 (9) | 0.5661 (12) |
C35 | 0.1202 (3) | 0.8674 (8) | 0.3122 (5) | 0.0268 (9) | 0.5661 (12) |
C36 | 0.2549 (4) | 0.8222 (7) | 0.3583 (4) | 0.0289 (7) | 0.5661 (12) |
H36 | 0.2622 | 0.7541 | 0.4330 | 0.035* | 0.5661 (12) |
C37 | −0.0376 (5) | 1.0069 (13) | 0.1453 (7) | 0.0399 (5) | 0.5661 (12) |
H37A | −0.0264 | 1.0766 | 0.0678 | 0.060* | 0.5661 (12) |
H37B | −0.1150 | 1.0399 | 0.1927 | 0.060* | 0.5661 (12) |
H37C | −0.0681 | 0.9283 | 0.1422 | 0.060* | 0.5661 (12) |
C38 | −0.0191 (6) | 0.8023 (17) | 0.3778 (9) | 0.0405 (6) | 0.5661 (12) |
H38A | 0.0054 | 0.7363 | 0.4536 | 0.061* | 0.5661 (12) |
H38B | −0.0537 | 0.7581 | 0.3362 | 0.061* | 0.5661 (12) |
H38C | −0.0996 | 0.8703 | 0.3862 | 0.061* | 0.5661 (12) |
O31A | 0.6029 (2) | 1.0540 (2) | 0.09597 (15) | 0.0518 (6) | 0.4339 (12) |
O32A | 0.6162 (2) | 0.8887 (2) | 0.27771 (15) | 0.0426 (4) | 0.4339 (12) |
N31A | 0.5335 (2) | 0.9758 (3) | 0.18167 (19) | 0.0386 (5) | 0.4339 (12) |
N32A | 0.5181 (3) | 0.8106 (3) | 0.36325 (18) | 0.0345 (4) | 0.4339 (12) |
C31A | 0.3903 (3) | 0.9475 (6) | 0.2107 (4) | 0.0278 (5) | 0.4339 (12) |
C32A | 0.3830 (3) | 0.8480 (7) | 0.3220 (4) | 0.0276 (5) | 0.4339 (12) |
C33A | 0.2441 (5) | 0.7959 (11) | 0.3736 (6) | 0.0289 (7) | 0.4339 (12) |
H33A | 0.2372 | 0.7270 | 0.4483 | 0.035* | 0.4339 (12) |
C34A | 0.1195 (4) | 0.8472 (10) | 0.3131 (6) | 0.0268 (9) | 0.4339 (12) |
C35A | 0.1302 (4) | 0.9518 (11) | 0.1973 (6) | 0.0279 (9) | 0.4339 (12) |
C36A | 0.2631 (5) | 1.0028 (12) | 0.1473 (6) | 0.0325 (5) | 0.4339 (12) |
H36A | 0.2701 | 1.0725 | 0.0731 | 0.039* | 0.4339 (12) |
C37A | −0.0331 (7) | 0.805 (2) | 0.3693 (11) | 0.0405 (6) | 0.4339 (12) |
H37D | −0.0221 | 0.7349 | 0.4459 | 0.061* | 0.4339 (12) |
H37E | −0.0767 | 0.7721 | 0.3234 | 0.061* | 0.4339 (12) |
H37F | −0.1001 | 0.8822 | 0.3755 | 0.061* | 0.4339 (12) |
C38A | −0.0119 (6) | 1.0138 (18) | 0.1376 (10) | 0.0399 (5) | 0.4339 (12) |
H38D | 0.0137 | 1.0817 | 0.0613 | 0.060* | 0.4339 (12) |
H38E | −0.0835 | 1.0552 | 0.1822 | 0.060* | 0.4339 (12) |
H38F | −0.0583 | 0.9447 | 0.1304 | 0.060* | 0.4339 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O11 | 0.0360 (7) | 0.0527 (8) | 0.0459 (7) | 0.0007 (6) | −0.0167 (6) | −0.0099 (6) |
O12 | 0.0297 (6) | 0.0394 (8) | 0.0461 (9) | −0.0095 (6) | −0.0002 (6) | −0.0121 (6) |
N11 | 0.0317 (7) | 0.0317 (9) | 0.0357 (9) | −0.0040 (7) | −0.0028 (7) | −0.0102 (7) |
N12 | 0.0355 (8) | 0.0348 (10) | 0.0366 (10) | −0.0084 (7) | 0.0016 (7) | −0.0075 (7) |
C11 | 0.0292 (7) | 0.0280 (13) | 0.0290 (12) | −0.0015 (6) | −0.0029 (7) | −0.0112 (8) |
C12 | 0.0315 (8) | 0.0259 (12) | 0.0298 (11) | −0.0043 (7) | 0.0001 (6) | −0.0094 (8) |
C13 | 0.0349 (10) | 0.0294 (11) | 0.0279 (10) | −0.0016 (10) | −0.0027 (6) | −0.0071 (7) |
C14 | 0.0281 (8) | 0.0304 (8) | 0.0310 (6) | 0.0019 (8) | −0.0027 (6) | −0.0143 (5) |
C15 | 0.0300 (6) | 0.0300 (9) | 0.0315 (6) | −0.0058 (5) | 0.0019 (5) | −0.0133 (6) |
C16 | 0.0345 (8) | 0.0263 (15) | 0.0278 (10) | −0.0048 (6) | −0.0009 (7) | −0.0064 (6) |
C17 | 0.0308 (12) | 0.0476 (13) | 0.0399 (10) | −0.0011 (11) | −0.0067 (11) | −0.0180 (8) |
C18 | 0.0347 (8) | 0.0487 (8) | 0.0395 (13) | −0.0157 (7) | 0.0024 (7) | −0.0170 (11) |
O11A | 0.036 (2) | 0.042 (2) | 0.051 (3) | −0.0165 (18) | 0.0069 (19) | −0.0040 (19) |
O12A | 0.0297 (6) | 0.0394 (8) | 0.0461 (9) | −0.0095 (6) | −0.0002 (6) | −0.0121 (6) |
N11A | 0.0355 (8) | 0.0348 (10) | 0.0366 (10) | −0.0084 (7) | 0.0016 (7) | −0.0075 (7) |
N12A | 0.0317 (7) | 0.0317 (9) | 0.0357 (9) | −0.0040 (7) | −0.0028 (7) | −0.0102 (7) |
C11A | 0.0315 (8) | 0.0259 (12) | 0.0298 (11) | −0.0043 (7) | 0.0001 (6) | −0.0094 (8) |
C12A | 0.0292 (7) | 0.0280 (13) | 0.0290 (12) | −0.0015 (6) | −0.0029 (7) | −0.0112 (8) |
C13A | 0.0345 (8) | 0.0263 (15) | 0.0278 (10) | −0.0048 (6) | −0.0009 (7) | −0.0064 (6) |
C14A | 0.0300 (6) | 0.0300 (9) | 0.0315 (6) | −0.0058 (5) | 0.0019 (5) | −0.0133 (6) |
C15A | 0.0281 (8) | 0.0304 (8) | 0.0310 (6) | 0.0019 (8) | −0.0027 (6) | −0.0143 (5) |
C16A | 0.0349 (10) | 0.0294 (11) | 0.0279 (10) | −0.0016 (10) | −0.0027 (6) | −0.0071 (7) |
C17A | 0.0347 (8) | 0.0487 (8) | 0.0395 (13) | −0.0157 (7) | 0.0024 (7) | −0.0170 (11) |
C18A | 0.0308 (12) | 0.0476 (13) | 0.0399 (10) | −0.0011 (11) | −0.0067 (11) | −0.0180 (8) |
O21 | 0.0425 (12) | 0.0566 (13) | 0.0468 (12) | 0.0022 (10) | −0.0208 (9) | −0.0103 (10) |
O22 | 0.0325 (7) | 0.0490 (12) | 0.0502 (11) | −0.0090 (8) | −0.0053 (9) | −0.0154 (8) |
N21 | 0.0414 (9) | 0.0349 (14) | 0.0341 (14) | 0.0019 (11) | −0.0129 (12) | −0.0096 (10) |
N22 | 0.0359 (10) | 0.0362 (14) | 0.0373 (14) | −0.0090 (10) | −0.0017 (11) | −0.0080 (10) |
C21 | 0.0316 (8) | 0.022 (3) | 0.029 (2) | −0.0010 (9) | −0.0056 (10) | −0.0073 (14) |
C22 | 0.0299 (9) | 0.021 (2) | 0.029 (2) | −0.0012 (11) | −0.0039 (9) | −0.0045 (14) |
C23 | 0.0347 (15) | 0.026 (2) | 0.0290 (17) | 0.0004 (19) | −0.0030 (8) | −0.0065 (12) |
C24 | 0.0252 (12) | 0.0263 (18) | 0.0356 (7) | 0.0058 (16) | −0.0033 (8) | −0.0158 (7) |
C25 | 0.0327 (7) | 0.019 (2) | 0.0354 (6) | −0.0043 (7) | 0.0024 (5) | −0.0163 (9) |
C26 | 0.0428 (9) | 0.016 (3) | 0.0312 (13) | −0.0041 (7) | −0.0051 (8) | −0.0051 (9) |
C27 | 0.0321 (19) | 0.0471 (18) | 0.0437 (12) | 0.0014 (19) | −0.0084 (16) | −0.0207 (9) |
C28 | 0.0369 (10) | 0.0489 (9) | 0.0468 (18) | −0.0181 (10) | 0.0061 (8) | −0.0222 (17) |
O21A | 0.0352 (11) | 0.0519 (12) | 0.0583 (13) | −0.0208 (9) | 0.0062 (9) | −0.0072 (10) |
O22A | 0.0325 (7) | 0.0490 (12) | 0.0502 (11) | −0.0090 (8) | −0.0053 (9) | −0.0154 (8) |
N21A | 0.0359 (10) | 0.0362 (14) | 0.0373 (14) | −0.0090 (10) | −0.0017 (11) | −0.0080 (10) |
N22A | 0.0414 (9) | 0.0349 (14) | 0.0341 (14) | 0.0019 (11) | −0.0129 (12) | −0.0096 (10) |
C21A | 0.0299 (9) | 0.021 (2) | 0.029 (2) | −0.0012 (11) | −0.0039 (9) | −0.0045 (14) |
C22A | 0.0316 (8) | 0.022 (3) | 0.029 (2) | −0.0010 (9) | −0.0056 (10) | −0.0073 (14) |
C23A | 0.0428 (9) | 0.016 (3) | 0.0312 (13) | −0.0041 (7) | −0.0051 (8) | −0.0051 (9) |
C24A | 0.0327 (7) | 0.019 (2) | 0.0354 (6) | −0.0043 (7) | 0.0024 (5) | −0.0163 (9) |
C25A | 0.0252 (12) | 0.0263 (18) | 0.0356 (7) | 0.0058 (16) | −0.0033 (8) | −0.0158 (7) |
C26A | 0.0347 (15) | 0.026 (2) | 0.0290 (17) | 0.0004 (19) | −0.0030 (8) | −0.0065 (12) |
C27A | 0.0369 (10) | 0.0489 (9) | 0.0468 (18) | −0.0181 (10) | 0.0061 (8) | −0.0222 (17) |
C28A | 0.0321 (19) | 0.0471 (18) | 0.0437 (12) | 0.0014 (19) | −0.0084 (16) | −0.0207 (9) |
O31 | 0.0326 (10) | 0.0538 (11) | 0.0506 (11) | 0.0022 (8) | −0.0176 (8) | −0.0108 (9) |
O32 | 0.0281 (6) | 0.0447 (11) | 0.0502 (12) | −0.0100 (8) | 0.0023 (8) | −0.0145 (8) |
N31 | 0.0307 (7) | 0.0306 (14) | 0.0378 (15) | −0.0034 (10) | −0.0039 (11) | −0.0094 (10) |
N32 | 0.0347 (10) | 0.0357 (15) | 0.0387 (15) | −0.0092 (10) | 0.0027 (11) | −0.0089 (11) |
C31 | 0.0269 (7) | 0.024 (2) | 0.0291 (19) | −0.0030 (7) | −0.0021 (8) | −0.0081 (13) |
C32 | 0.0274 (8) | 0.021 (2) | 0.0290 (18) | −0.0035 (10) | 0.0001 (8) | −0.0056 (12) |
C33 | 0.0338 (13) | 0.026 (2) | 0.0303 (15) | −0.0001 (18) | −0.0017 (8) | −0.0064 (10) |
C34 | 0.0256 (10) | 0.0246 (19) | 0.0340 (6) | 0.0059 (13) | −0.0024 (7) | −0.0160 (8) |
C35 | 0.0290 (6) | 0.022 (2) | 0.0348 (6) | −0.0071 (6) | 0.0020 (5) | −0.0173 (8) |
C36 | 0.0343 (8) | 0.020 (3) | 0.0297 (13) | −0.0074 (6) | −0.0022 (8) | −0.0056 (9) |
C37 | 0.0294 (14) | 0.0503 (13) | 0.0423 (12) | 0.0000 (19) | −0.0062 (15) | −0.0218 (9) |
C38 | 0.0319 (10) | 0.0509 (10) | 0.0415 (13) | −0.0154 (15) | 0.0045 (8) | −0.0203 (11) |
O31A | 0.0423 (14) | 0.0481 (13) | 0.0497 (14) | −0.0199 (11) | 0.0101 (11) | −0.0047 (11) |
O32A | 0.0281 (6) | 0.0447 (11) | 0.0502 (12) | −0.0100 (8) | 0.0023 (8) | −0.0145 (8) |
N31A | 0.0347 (10) | 0.0357 (15) | 0.0387 (15) | −0.0092 (10) | 0.0027 (11) | −0.0089 (11) |
N32A | 0.0307 (7) | 0.0306 (14) | 0.0378 (15) | −0.0034 (10) | −0.0039 (11) | −0.0094 (10) |
C31A | 0.0274 (8) | 0.021 (2) | 0.0290 (18) | −0.0035 (10) | 0.0001 (8) | −0.0056 (12) |
C32A | 0.0269 (7) | 0.024 (2) | 0.0291 (19) | −0.0030 (7) | −0.0021 (8) | −0.0081 (13) |
C33A | 0.0343 (8) | 0.020 (3) | 0.0297 (13) | −0.0074 (6) | −0.0022 (8) | −0.0056 (9) |
C34A | 0.0290 (6) | 0.022 (2) | 0.0348 (6) | −0.0071 (6) | 0.0020 (5) | −0.0173 (8) |
C35A | 0.0256 (10) | 0.0246 (19) | 0.0340 (6) | 0.0059 (13) | −0.0024 (7) | −0.0160 (8) |
C36A | 0.0338 (13) | 0.026 (2) | 0.0303 (15) | −0.0001 (18) | −0.0017 (8) | −0.0064 (10) |
C37A | 0.0319 (10) | 0.0509 (10) | 0.0415 (13) | −0.0154 (15) | 0.0045 (8) | −0.0203 (11) |
C38A | 0.0294 (14) | 0.0503 (13) | 0.0423 (12) | 0.0000 (19) | −0.0062 (15) | −0.0218 (9) |
O11—N11 | 1.2389 (14) | O21A—N21A | 1.2390 (14) |
O12—N12 | 1.3808 (14) | O22A—N22A | 1.3812 (14) |
O12—N11 | 1.4416 (14) | O22A—N21A | 1.4417 (14) |
N11—C11 | 1.3373 (19) | N21A—C21A | 1.3373 (19) |
N12—C12 | 1.3359 (18) | N22A—C22A | 1.3363 (19) |
C11—C12 | 1.4015 (15) | C21A—C22A | 1.4012 (16) |
C11—C16 | 1.414 (2) | C21A—C26A | 1.414 (2) |
C12—C13 | 1.417 (2) | C22A—C23A | 1.417 (2) |
C13—C14 | 1.373 (2) | C23A—C24A | 1.373 (2) |
C13—H13 | 0.9500 | C23A—H23A | 0.9500 |
C14—C15 | 1.4619 (12) | C24A—C25A | 1.4621 (13) |
C14—C17 | 1.499 (2) | C24A—C27A | 1.500 (2) |
C15—C16 | 1.361 (2) | C25A—C26A | 1.361 (2) |
C15—C18 | 1.508 (2) | C25A—C28A | 1.508 (2) |
C16—H16 | 0.9500 | C26A—H26A | 0.9500 |
C17—H17A | 0.9800 | C27A—H27D | 0.9800 |
C17—H17B | 0.9800 | C27A—H27E | 0.9800 |
C17—H17C | 0.9800 | C27A—H27F | 0.9800 |
C18—H18A | 0.9800 | C28A—H28D | 0.9800 |
C18—H18B | 0.9800 | C28A—H28E | 0.9800 |
C18—H18C | 0.9800 | C28A—H28F | 0.9800 |
O11A—N11A | 1.2390 (15) | O31—N31 | 1.2393 (14) |
O12A—N12A | 1.3809 (14) | O32—N32 | 1.3811 (14) |
O12A—N11A | 1.4413 (14) | O32—N31 | 1.4410 (14) |
N11A—C11A | 1.337 (2) | N31—C31 | 1.3374 (19) |
N12A—C12A | 1.3365 (19) | N32—C32 | 1.3361 (19) |
C11A—C12A | 1.4013 (16) | C31—C32 | 1.4014 (16) |
C11A—C16A | 1.414 (2) | C31—C36 | 1.414 (2) |
C12A—C13A | 1.417 (2) | C32—C33 | 1.417 (2) |
C13A—C14A | 1.373 (2) | C33—C34 | 1.373 (2) |
C13A—H13A | 0.9500 | C33—H33 | 0.9500 |
C14A—C15A | 1.4625 (13) | C34—C35 | 1.4626 (13) |
C14A—C17A | 1.499 (2) | C34—C37 | 1.500 (2) |
C15A—C16A | 1.361 (2) | C35—C36 | 1.360 (2) |
C15A—C18A | 1.509 (2) | C35—C38 | 1.509 (2) |
C16A—H16A | 0.9500 | C36—H36 | 0.9500 |
C17A—H17D | 0.9800 | C37—H37A | 0.9800 |
C17A—H17E | 0.9800 | C37—H37B | 0.9800 |
C17A—H17F | 0.9800 | C37—H37C | 0.9800 |
C18A—H18D | 0.9800 | C38—H38A | 0.9800 |
C18A—H18E | 0.9800 | C38—H38B | 0.9800 |
C18A—H18F | 0.9800 | C38—H38C | 0.9800 |
O21—N21 | 1.2390 (14) | O31A—N31A | 1.2391 (14) |
O22—N22 | 1.3810 (14) | O32A—N32A | 1.3809 (14) |
O22—N21 | 1.4414 (14) | O32A—N31A | 1.4413 (14) |
N21—C21 | 1.3375 (19) | N31A—C31A | 1.3373 (19) |
N22—C22 | 1.3363 (19) | N32A—C32A | 1.3366 (19) |
C21—C22 | 1.4012 (16) | C31A—C32A | 1.4013 (16) |
C21—C26 | 1.414 (2) | C31A—C36A | 1.414 (2) |
C22—C23 | 1.417 (2) | C32A—C33A | 1.417 (2) |
C23—C24 | 1.373 (2) | C33A—C34A | 1.373 (2) |
C23—H23 | 0.9500 | C33A—H33A | 0.9500 |
C24—C25 | 1.4619 (13) | C34A—C35A | 1.4626 (13) |
C24—C27 | 1.499 (2) | C34A—C37A | 1.500 (2) |
C25—C26 | 1.361 (2) | C35A—C36A | 1.361 (2) |
C25—C28 | 1.509 (2) | C35A—C38A | 1.509 (2) |
C26—H26 | 0.9500 | C36A—H36A | 0.9500 |
C27—H27A | 0.9800 | C37A—H37D | 0.9800 |
C27—H27B | 0.9800 | C37A—H37E | 0.9800 |
C27—H27C | 0.9800 | C37A—H37F | 0.9800 |
C28—H28A | 0.9800 | C38A—H38D | 0.9800 |
C28—H28B | 0.9800 | C38A—H38E | 0.9800 |
C28—H28C | 0.9800 | C38A—H38F | 0.9800 |
N12—O12—N11 | 109.02 (9) | N22A—O22A—N21A | 109.01 (9) |
O11—N11—C11 | 135.08 (13) | O21A—N21A—C21A | 135.13 (14) |
O11—N11—O12 | 118.57 (11) | O21A—N21A—O22A | 118.52 (11) |
C11—N11—O12 | 106.34 (10) | C21A—N21A—O22A | 106.34 (10) |
C12—N12—O12 | 105.41 (10) | C22A—N22A—O22A | 105.40 (11) |
N11—C11—C12 | 107.35 (14) | N21A—C21A—C22A | 107.37 (14) |
N11—C11—C16 | 129.64 (14) | N21A—C21A—C26A | 129.63 (15) |
C12—C11—C16 | 123.01 (16) | C22A—C21A—C26A | 122.99 (17) |
N12—C12—C11 | 111.87 (14) | N22A—C22A—C21A | 111.87 (15) |
N12—C12—C13 | 128.64 (13) | N22A—C22A—C23A | 128.62 (14) |
C11—C12—C13 | 119.49 (15) | C21A—C22A—C23A | 119.49 (16) |
C14—C13—C12 | 118.40 (13) | C24A—C23A—C22A | 118.41 (14) |
C14—C13—H13 | 120.8 | C24A—C23A—H23A | 120.8 |
C12—C13—H13 | 120.8 | C22A—C23A—H23A | 120.8 |
C13—C14—C15 | 120.92 (17) | C23A—C24A—C25A | 120.89 (19) |
C13—C14—C17 | 120.05 (16) | C23A—C24A—C27A | 119.89 (17) |
C15—C14—C17 | 119.01 (18) | C25A—C24A—C27A | 118.96 (19) |
C16—C15—C14 | 121.07 (17) | C26A—C25A—C24A | 121.05 (18) |
C16—C15—C18 | 119.56 (16) | C26A—C25A—C28A | 119.52 (18) |
C14—C15—C18 | 119.35 (18) | C24A—C25A—C28A | 119.32 (19) |
C15—C16—C11 | 117.12 (14) | C25A—C26A—C21A | 117.12 (15) |
C15—C16—H16 | 121.4 | C25A—C26A—H26A | 121.4 |
C11—C16—H16 | 121.4 | C21A—C26A—H26A | 121.4 |
C14—C17—H17A | 109.5 | C24A—C27A—H27D | 109.5 |
C14—C17—H17B | 109.5 | C24A—C27A—H27E | 109.5 |
H17A—C17—H17B | 109.5 | H27D—C27A—H27E | 109.5 |
C14—C17—H17C | 109.5 | C24A—C27A—H27F | 109.5 |
H17A—C17—H17C | 109.5 | H27D—C27A—H27F | 109.5 |
H17B—C17—H17C | 109.5 | H27E—C27A—H27F | 109.5 |
C15—C18—H18A | 109.5 | C25A—C28A—H28D | 109.5 |
C15—C18—H18B | 109.5 | C25A—C28A—H28E | 109.5 |
H18A—C18—H18B | 109.5 | H28D—C28A—H28E | 109.5 |
C15—C18—H18C | 109.5 | C25A—C28A—H28F | 109.5 |
H18A—C18—H18C | 109.5 | H28D—C28A—H28F | 109.5 |
H18B—C18—H18C | 109.5 | H28E—C28A—H28F | 109.5 |
N12A—O12A—N11A | 109.03 (9) | N32—O32—N31 | 109.01 (9) |
O11A—N11A—C11A | 135.09 (14) | O31—N31—C31 | 135.05 (13) |
O11A—N11A—O12A | 118.58 (12) | O31—N31—O32 | 118.59 (11) |
C11A—N11A—O12A | 106.33 (11) | C31—N31—O32 | 106.36 (10) |
C12A—N12A—O12A | 105.40 (11) | C32—N32—O32 | 105.43 (10) |
N11A—C11A—C12A | 107.38 (14) | N31—C31—C32 | 107.37 (14) |
N11A—C11A—C16A | 129.62 (15) | N31—C31—C36 | 129.61 (15) |
C12A—C11A—C16A | 123.00 (17) | C32—C31—C36 | 122.98 (17) |
N12A—C12A—C11A | 111.84 (15) | N32—C32—C31 | 111.84 (14) |
N12A—C12A—C13A | 128.59 (15) | N32—C32—C33 | 128.67 (14) |
C11A—C12A—C13A | 119.46 (17) | C31—C32—C33 | 119.49 (16) |
C14A—C13A—C12A | 118.40 (14) | C34—C33—C32 | 118.41 (14) |
C14A—C13A—H13A | 120.8 | C34—C33—H33 | 120.8 |
C12A—C13A—H13A | 120.8 | C32—C33—H33 | 120.8 |
C13A—C14A—C15A | 120.9 (2) | C33—C34—C35 | 120.87 (18) |
C13A—C14A—C17A | 120.00 (18) | C33—C34—C37 | 120.00 (17) |
C15A—C14A—C17A | 118.9 (2) | C35—C34—C37 | 118.91 (19) |
C16A—C15A—C14A | 121.0 (2) | C36—C35—C34 | 121.05 (18) |
C16A—C15A—C18A | 119.45 (18) | C36—C35—C38 | 119.46 (17) |
C14A—C15A—C18A | 119.3 (2) | C34—C35—C38 | 119.24 (19) |
C15A—C16A—C11A | 117.11 (15) | C35—C36—C31 | 117.15 (14) |
C15A—C16A—H16A | 121.4 | C35—C36—H36 | 121.4 |
C11A—C16A—H16A | 121.4 | C31—C36—H36 | 121.4 |
C14A—C17A—H17D | 109.5 | C34—C37—H37A | 109.5 |
C14A—C17A—H17E | 109.5 | C34—C37—H37B | 109.5 |
H17D—C17A—H17E | 109.5 | H37A—C37—H37B | 109.5 |
C14A—C17A—H17F | 109.5 | C34—C37—H37C | 109.5 |
H17D—C17A—H17F | 109.5 | H37A—C37—H37C | 109.5 |
H17E—C17A—H17F | 109.5 | H37B—C37—H37C | 109.5 |
C15A—C18A—H18D | 109.5 | C35—C38—H38A | 109.5 |
C15A—C18A—H18E | 109.5 | C35—C38—H38B | 109.5 |
H18D—C18A—H18E | 109.5 | H38A—C38—H38B | 109.5 |
C15A—C18A—H18F | 109.5 | C35—C38—H38C | 109.5 |
H18D—C18A—H18F | 109.5 | H38A—C38—H38C | 109.5 |
H18E—C18A—H18F | 109.5 | H38B—C38—H38C | 109.5 |
N22—O22—N21 | 109.01 (9) | N32A—O32A—N31A | 109.04 (9) |
O21—N21—C21 | 135.09 (14) | O31A—N31A—C31A | 135.14 (14) |
O21—N21—O22 | 118.58 (11) | O31A—N31A—O32A | 118.52 (12) |
C21—N21—O22 | 106.34 (10) | C31A—N31A—O32A | 106.34 (10) |
C22—N22—O22 | 105.41 (11) | C32A—N32A—O32A | 105.39 (11) |
N21—C21—C22 | 107.38 (14) | N31A—C31A—C32A | 107.37 (14) |
N21—C21—C26 | 129.60 (15) | N31A—C31A—C36A | 129.63 (15) |
C22—C21—C26 | 123.00 (17) | C32A—C31A—C36A | 123.00 (17) |
N22—C22—C21 | 111.85 (15) | N32A—C32A—C31A | 111.86 (15) |
N22—C22—C23 | 128.67 (14) | N32A—C32A—C33A | 128.60 (14) |
C21—C22—C23 | 119.49 (16) | C31A—C32A—C33A | 119.46 (16) |
C24—C23—C22 | 118.39 (14) | C34A—C33A—C32A | 118.44 (14) |
C24—C23—H23 | 120.8 | C34A—C33A—H33A | 120.8 |
C22—C23—H23 | 120.8 | C32A—C33A—H33A | 120.8 |
C23—C24—C25 | 120.88 (19) | C33A—C34A—C35A | 120.90 (19) |
C23—C24—C27 | 120.03 (17) | C33A—C34A—C37A | 119.96 (18) |
C25—C24—C27 | 119.02 (19) | C35A—C34A—C37A | 118.90 (19) |
C26—C25—C24 | 121.06 (18) | C36A—C35A—C34A | 121.02 (18) |
C26—C25—C28 | 119.41 (17) | C36A—C35A—C38A | 119.46 (18) |
C24—C25—C28 | 119.3 (2) | C34A—C35A—C38A | 119.2 (2) |
C25—C26—C21 | 117.11 (15) | C35A—C36A—C31A | 117.13 (15) |
C25—C26—H26 | 121.4 | C35A—C36A—H36A | 121.4 |
C21—C26—H26 | 121.4 | C31A—C36A—H36A | 121.4 |
C24—C27—H27A | 109.5 | C34A—C37A—H37D | 109.5 |
C24—C27—H27B | 109.5 | C34A—C37A—H37E | 109.5 |
H27A—C27—H27B | 109.5 | H37D—C37A—H37E | 109.5 |
C24—C27—H27C | 109.5 | C34A—C37A—H37F | 109.5 |
H27A—C27—H27C | 109.5 | H37D—C37A—H37F | 109.5 |
H27B—C27—H27C | 109.5 | H37E—C37A—H37F | 109.5 |
C25—C28—H28A | 109.5 | C35A—C38A—H38D | 109.5 |
C25—C28—H28B | 109.5 | C35A—C38A—H38E | 109.5 |
H28A—C28—H28B | 109.5 | H38D—C38A—H38E | 109.5 |
C25—C28—H28C | 109.5 | C35A—C38A—H38F | 109.5 |
H28A—C28—H28C | 109.5 | H38D—C38A—H38F | 109.5 |
H28B—C28—H28C | 109.5 | H38E—C38A—H38F | 109.5 |
N12—O12—N11—O11 | −179.91 (14) | N22A—O22A—N21A—O21A | 179.6 (3) |
N12—O12—N11—C11 | −0.1 (2) | N22A—O22A—N21A—C21A | −0.6 (4) |
N11—O12—N12—C12 | 0.0 (2) | N21A—O22A—N22A—C22A | 0.5 (4) |
O11—N11—C11—C12 | 179.9 (2) | O21A—N21A—C21A—C22A | −179.8 (4) |
O12—N11—C11—C12 | 0.2 (3) | O22A—N21A—C21A—C22A | 0.4 (6) |
O11—N11—C11—C16 | −0.6 (5) | O21A—N21A—C21A—C26A | −0.4 (13) |
O12—N11—C11—C16 | 179.7 (4) | O22A—N21A—C21A—C26A | 179.8 (9) |
O12—N12—C12—C11 | 0.1 (3) | O22A—N22A—C22A—C21A | −0.3 (6) |
O12—N12—C12—C13 | −179.8 (3) | O22A—N22A—C22A—C23A | 178.0 (9) |
N11—C11—C12—N12 | −0.2 (3) | N21A—C21A—C22A—N22A | −0.1 (7) |
C16—C11—C12—N12 | −179.8 (3) | C26A—C21A—C22A—N22A | −179.5 (9) |
N11—C11—C12—C13 | 179.7 (3) | N21A—C21A—C22A—C23A | −178.5 (8) |
C16—C11—C12—C13 | 0.1 (5) | C26A—C21A—C22A—C23A | 2.1 (13) |
N12—C12—C13—C14 | 178.9 (3) | N22A—C22A—C23A—C24A | −178.2 (8) |
C11—C12—C13—C14 | −1.0 (5) | C21A—C22A—C23A—C24A | −0.1 (14) |
C12—C13—C14—C15 | 1.3 (6) | C22A—C23A—C24A—C25A | −1.4 (14) |
C12—C13—C14—C17 | 179.7 (4) | C22A—C23A—C24A—C27A | −175.5 (12) |
C13—C14—C15—C16 | −0.7 (7) | C23A—C24A—C25A—C26A | 1.1 (14) |
C17—C14—C15—C16 | −179.2 (5) | C27A—C24A—C25A—C26A | 175.3 (14) |
C13—C14—C15—C18 | −179.3 (5) | C23A—C24A—C25A—C28A | −175.2 (13) |
C17—C14—C15—C18 | 2.3 (6) | C27A—C24A—C25A—C28A | −1.0 (13) |
C14—C15—C16—C11 | −0.1 (7) | C24A—C25A—C26A—C21A | 0.8 (16) |
C18—C15—C16—C11 | 178.4 (5) | C28A—C25A—C26A—C21A | 177.1 (12) |
N11—C11—C16—C15 | −179.1 (4) | N21A—C21A—C26A—C25A | 178.4 (9) |
C12—C11—C16—C15 | 0.4 (6) | C22A—C21A—C26A—C25A | −2.4 (15) |
N12A—O12A—N11A—O11A | 179.7 (5) | N32—O32—N31—O31 | 179.3 (2) |
N12A—O12A—N11A—C11A | −0.5 (8) | N32—O32—N31—C31 | 0.0 (4) |
N11A—O12A—N12A—C12A | 1.1 (8) | N31—O32—N32—C32 | 0.3 (4) |
O11A—N11A—C11A—C12A | 179.6 (8) | O31—N31—C31—C32 | −179.4 (4) |
O12A—N11A—C11A—C12A | −0.3 (10) | O32—N31—C31—C32 | −0.3 (5) |
O11A—N11A—C11A—C16A | 0 (2) | O31—N31—C31—C36 | 2.9 (11) |
O12A—N11A—C11A—C16A | −180.0 (13) | O32—N31—C31—C36 | −177.9 (7) |
O12A—N12A—C12A—C11A | −1.2 (11) | O32—N32—C32—C31 | −0.5 (6) |
O12A—N12A—C12A—C13A | −177.5 (13) | O32—N32—C32—C33 | 178.8 (8) |
N11A—C11A—C12A—N12A | 1.0 (13) | N31—C31—C32—N32 | 0.5 (7) |
C16A—C11A—C12A—N12A | −179.3 (12) | C36—C31—C32—N32 | 178.3 (7) |
N11A—C11A—C12A—C13A | 177.6 (12) | N31—C31—C32—C33 | −178.9 (7) |
C16A—C11A—C12A—C13A | −3 (2) | C36—C31—C32—C33 | −1.0 (11) |
N12A—C12A—C13A—C14A | 178.7 (14) | N32—C32—C33—C34 | −176.8 (7) |
C11A—C12A—C13A—C14A | 3 (2) | C31—C32—C33—C34 | 2.5 (13) |
C12A—C13A—C14A—C15A | −3 (2) | C32—C33—C34—C35 | −1.9 (12) |
C12A—C13A—C14A—C17A | −178.3 (17) | C32—C33—C34—C37 | −176.4 (10) |
C13A—C14A—C15A—C16A | 4 (2) | C33—C34—C35—C36 | −0.2 (11) |
C17A—C14A—C15A—C16A | 178.8 (17) | C37—C34—C35—C36 | 174.3 (10) |
C13A—C14A—C15A—C18A | 177.5 (17) | C33—C34—C35—C38 | −174.6 (11) |
C17A—C14A—C15A—C18A | −7 (2) | C37—C34—C35—C38 | 0.0 (10) |
C14A—C15A—C16A—C11A | −3 (2) | C34—C35—C36—C31 | 1.7 (12) |
C18A—C15A—C16A—C11A | −177.2 (15) | C38—C35—C36—C31 | 176.0 (11) |
N11A—C11A—C16A—C15A | −177.3 (13) | N31—C31—C36—C35 | 176.3 (7) |
C12A—C11A—C16A—C15A | 3 (2) | C32—C31—C36—C35 | −1.0 (12) |
N22—O22—N21—O21 | 178.6 (3) | N32A—O32A—N31A—O31A | 179.9 (3) |
N22—O22—N21—C21 | −1.1 (4) | N32A—O32A—N31A—C31A | −0.7 (6) |
N21—O22—N22—C22 | 1.1 (4) | N31A—O32A—N32A—C32A | −0.1 (6) |
O21—N21—C21—C22 | −179.0 (4) | O31A—N31A—C31A—C32A | −179.6 (6) |
O22—N21—C21—C22 | 0.6 (6) | O32A—N31A—C31A—C32A | 1.1 (8) |
O21—N21—C21—C26 | 2.9 (12) | O31A—N31A—C31A—C36A | −0.1 (16) |
O22—N21—C21—C26 | −177.4 (9) | O32A—N31A—C31A—C36A | −179.3 (11) |
O22—N22—C22—C21 | −0.7 (6) | O32A—N32A—C32A—C31A | 0.8 (8) |
O22—N22—C22—C23 | 179.5 (9) | O32A—N32A—C32A—C33A | 177.4 (10) |
N21—C21—C22—N22 | 0.0 (7) | N31A—C31A—C32A—N32A | −1.3 (9) |
C26—C21—C22—N22 | 178.3 (8) | C36A—C31A—C32A—N32A | 179.1 (10) |
N21—C21—C22—C23 | 179.8 (8) | N31A—C31A—C32A—C33A | −178.2 (10) |
C26—C21—C22—C23 | −2.0 (12) | C36A—C31A—C32A—C33A | 2.2 (15) |
N22—C22—C23—C24 | −177.6 (9) | N32A—C32A—C33A—C34A | −177.8 (10) |
C21—C22—C23—C24 | 2.7 (15) | C31A—C32A—C33A—C34A | −1.4 (16) |
C22—C23—C24—C25 | −1.0 (16) | C32A—C33A—C34A—C35A | 1.0 (16) |
C22—C23—C24—C27 | −177.8 (12) | C32A—C33A—C34A—C37A | −173.3 (15) |
C23—C24—C25—C26 | −1.5 (14) | C33A—C34A—C35A—C36A | −1.3 (14) |
C27—C24—C25—C26 | 175.3 (13) | C37A—C34A—C35A—C36A | 173.1 (15) |
C23—C24—C25—C28 | −176.3 (14) | C33A—C34A—C35A—C38A | −174.8 (13) |
C27—C24—C25—C28 | 0.6 (13) | C37A—C34A—C35A—C38A | −0.4 (14) |
C24—C25—C26—C21 | 2.2 (14) | C34A—C35A—C36A—C31A | 1.9 (17) |
C28—C25—C26—C21 | 177.0 (11) | C38A—C35A—C36A—C31A | 175.4 (13) |
N21—C21—C26—C25 | 177.3 (8) | N31A—C31A—C36A—C35A | 178.1 (10) |
C22—C21—C26—C25 | −0.5 (14) | C32A—C31A—C36A—C35A | −2.4 (18) |
C8H8N2O2 | Z = 10 |
Mr = 164.16 | F(000) = 860 |
Triclinic, P1 | Dx = 1.417 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.0136 (18) Å | Cell parameters from 2747 reflections |
b = 13.064 (3) Å | θ = 2.4–27.1° |
c = 16.567 (3) Å | µ = 0.11 mm−1 |
α = 95.055 (4)° | T = 173 K |
β = 97.969 (4)° | Prism, pale yellow |
γ = 90.742 (4)° | 0.40 × 0.35 × 0.20 mm |
V = 1923.9 (7) Å3 |
Bruker SMART 1K CCD area-detector diffractometer | 8722 independent reflections |
Radiation source: fine-focus sealed tube | 3791 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
ω scans | θmax = 27.5°, θmin = 1.6° |
Absorption correction: multi-scan SADABS: Sheldrick, 2008; Blessing, 1995 | h = −11→11 |
Tmin = 0.96, Tmax = 0.98 | k = −16→16 |
22419 measured reflections | l = −21→21 |
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)] = 0.114 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.338 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.198P)2] where P = (Fo2 + 2Fc2)/3 |
8722 reflections | (Δ/σ)max = 0.005 |
756 parameters | Δρmax = 1.18 e Å−3 |
1440 restraints | Δρmin = −0.39 e Å−3 |
C8H8N2O2 | γ = 90.742 (4)° |
Mr = 164.16 | V = 1923.9 (7) Å3 |
Triclinic, P1 | Z = 10 |
a = 9.0136 (18) Å | Mo Kα radiation |
b = 13.064 (3) Å | µ = 0.11 mm−1 |
c = 16.567 (3) Å | T = 173 K |
α = 95.055 (4)° | 0.40 × 0.35 × 0.20 mm |
β = 97.969 (4)° |
Bruker SMART 1K CCD area-detector diffractometer | 8722 independent reflections |
Absorption correction: multi-scan SADABS: Sheldrick, 2008; Blessing, 1995 | 3791 reflections with I > 2σ(I) |
Tmin = 0.96, Tmax = 0.98 | Rint = 0.054 |
22419 measured reflections |
R[F2 > 2σ(F2)] = 0.114 | 1440 restraints |
wR(F2) = 0.338 | H-atom parameters constrained |
S = 0.97 | Δρmax = 1.18 e Å−3 |
8722 reflections | Δρmin = −0.39 e Å−3 |
756 parameters |
Refinement. The data were collected from a crystal that was a combination of two polymorphs, this one was the major component. No other crystal of this polymorph could be found |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C11 | −0.0692 (5) | 0.4871 (2) | 0.1077 (9) | 0.0257 (10) | 0.546 (2) |
C12 | −0.0633 (5) | 0.3792 (2) | 0.1012 (9) | 0.0230 (10) | 0.546 (2) |
C13 | 0.0746 (6) | 0.3318 (3) | 0.0928 (15) | 0.0259 (11) | 0.546 (2) |
H13 | 0.0807 | 0.2590 | 0.0877 | 0.031* | 0.546 (2) |
C14 | 0.1986 (6) | 0.3927 (4) | 0.0922 (13) | 0.0237 (9) | 0.546 (2) |
C15 | 0.1888 (7) | 0.5049 (4) | 0.0961 (15) | 0.0238 (8) | 0.546 (2) |
C16 | 0.0565 (7) | 0.5517 (3) | 0.1053 (16) | 0.0264 (9) | 0.546 (2) |
H16 | 0.0496 | 0.6244 | 0.1099 | 0.032* | 0.546 (2) |
C17 | 0.3461 (9) | 0.3455 (5) | 0.081 (2) | 0.0348 (9) | 0.546 (2) |
H17A | 0.3356 | 0.2705 | 0.0790 | 0.052* | 0.546 (2) |
H17B | 0.4214 | 0.3701 | 0.1279 | 0.052* | 0.546 (2) |
H17C | 0.3778 | 0.3650 | 0.0306 | 0.052* | 0.546 (2) |
C18 | 0.3286 (11) | 0.5696 (5) | 0.096 (3) | 0.0372 (8) | 0.546 (2) |
H18A | 0.3036 | 0.6425 | 0.1001 | 0.056* | 0.546 (2) |
H18B | 0.3711 | 0.5520 | 0.0458 | 0.056* | 0.546 (2) |
H18C | 0.4020 | 0.5564 | 0.1436 | 0.056* | 0.546 (2) |
N11 | −0.2096 (3) | 0.51036 (18) | 0.1178 (3) | 0.0303 (9) | 0.546 (2) |
N12 | −0.1963 (4) | 0.33506 (19) | 0.1045 (3) | 0.0320 (10) | 0.546 (2) |
O11 | −0.2762 (3) | 0.59255 (18) | 0.1268 (2) | 0.0431 (10) | 0.546 (2) |
O12 | −0.2920 (3) | 0.41516 (18) | 0.1151 (2) | 0.0361 (8) | 0.546 (2) |
C31 | 0.1377 (4) | 0.3904 (2) | 0.3007 (8) | 0.0249 (9) | 0.598 (3) |
C32 | 0.1451 (4) | 0.2826 (2) | 0.2958 (7) | 0.0265 (10) | 0.598 (3) |
C33 | 0.2852 (4) | 0.2360 (3) | 0.2926 (11) | 0.0305 (12) | 0.598 (3) |
H33 | 0.2920 | 0.1633 | 0.2867 | 0.037* | 0.598 (3) |
C34 | 0.4104 (4) | 0.2976 (3) | 0.2981 (9) | 0.0270 (12) | 0.598 (3) |
C35 | 0.3998 (4) | 0.4098 (3) | 0.3022 (9) | 0.0270 (6) | 0.598 (3) |
C36 | 0.2645 (5) | 0.4557 (3) | 0.3032 (12) | 0.0263 (9) | 0.598 (3) |
H36 | 0.2562 | 0.5283 | 0.3055 | 0.032* | 0.598 (3) |
C37 | 0.5606 (5) | 0.2514 (4) | 0.2935 (14) | 0.0368 (14) | 0.598 (3) |
H37A | 0.5500 | 0.1763 | 0.2886 | 0.055* | 0.598 (3) |
H37B | 0.6291 | 0.2743 | 0.3433 | 0.055* | 0.598 (3) |
H37C | 0.6010 | 0.2734 | 0.2457 | 0.055* | 0.598 (3) |
C38 | 0.5383 (4) | 0.4747 (4) | 0.2997 (8) | 0.0316 (18) | 0.598 (3) |
H38A | 0.5139 | 0.5476 | 0.3057 | 0.047* | 0.598 (3) |
H38B | 0.5754 | 0.4587 | 0.2472 | 0.047* | 0.598 (3) |
H38C | 0.6158 | 0.4600 | 0.3445 | 0.047* | 0.598 (3) |
N31 | −0.0053 (3) | 0.41285 (18) | 0.3049 (3) | 0.0305 (9) | 0.598 (3) |
N32 | 0.0107 (3) | 0.23768 (19) | 0.2937 (3) | 0.0366 (11) | 0.598 (3) |
O31 | −0.0736 (3) | 0.49470 (18) | 0.3115 (2) | 0.0474 (10) | 0.598 (3) |
O32 | −0.0875 (3) | 0.31723 (17) | 0.2998 (2) | 0.0393 (9) | 0.598 (3) |
C51 | 0.9965 (3) | 0.21124 (18) | 0.4933 (3) | 0.0236 (7) | 0.810 (3) |
C52 | 0.9921 (3) | 0.31917 (17) | 0.5004 (3) | 0.0234 (7) | 0.810 (3) |
C53 | 0.8548 (3) | 0.3674 (2) | 0.5091 (5) | 0.0265 (7) | 0.810 (3) |
H53 | 0.8496 | 0.4402 | 0.5143 | 0.032* | 0.810 (3) |
C54 | 0.7301 (3) | 0.3072 (2) | 0.5098 (5) | 0.0223 (6) | 0.810 (3) |
C55 | 0.7371 (3) | 0.1948 (2) | 0.5016 (5) | 0.0223 (8) | 0.810 (3) |
C56 | 0.8693 (3) | 0.1473 (2) | 0.4938 (5) | 0.0249 (8) | 0.810 (3) |
H56 | 0.8753 | 0.0745 | 0.4888 | 0.030* | 0.810 (3) |
C57 | 0.5821 (4) | 0.3552 (3) | 0.5177 (6) | 0.0327 (8) | 0.810 (3) |
H57A | 0.5945 | 0.4302 | 0.5226 | 0.049* | 0.810 (3) |
H57B | 0.5449 | 0.3336 | 0.5666 | 0.049* | 0.810 (3) |
H57C | 0.5102 | 0.3331 | 0.4692 | 0.049* | 0.810 (3) |
C58 | 0.5971 (5) | 0.1310 (3) | 0.5029 (10) | 0.0353 (13) | 0.810 (3) |
H58A | 0.6204 | 0.0579 | 0.4970 | 0.053* | 0.810 (3) |
H58B | 0.5210 | 0.1464 | 0.4577 | 0.053* | 0.810 (3) |
H58C | 0.5588 | 0.1472 | 0.5550 | 0.053* | 0.810 (3) |
N51 | 1.1376 (2) | 0.18727 (16) | 0.48532 (18) | 0.0290 (7) | 0.810 (3) |
N52 | 1.1257 (2) | 0.36267 (16) | 0.49752 (19) | 0.0327 (7) | 0.810 (3) |
O51 | 1.2037 (2) | 0.10475 (13) | 0.47714 (14) | 0.0405 (7) | 0.810 (3) |
O52 | 1.22086 (18) | 0.28206 (14) | 0.48775 (14) | 0.0333 (6) | 0.810 (3) |
C41 | 0.8640 (4) | 0.1857 (2) | 0.7114 (8) | 0.0316 (11) | 0.545 (2) |
C42 | 0.8685 (4) | 0.0778 (2) | 0.7038 (7) | 0.0266 (10) | 0.545 (2) |
C43 | 1.0052 (6) | 0.0298 (3) | 0.6932 (13) | 0.0320 (9) | 0.545 (2) |
H43 | 1.0096 | −0.0430 | 0.6852 | 0.038* | 0.545 (2) |
C44 | 1.1306 (5) | 0.0900 (3) | 0.6948 (12) | 0.0269 (13) | 0.545 (2) |
C45 | 1.1243 (5) | 0.2024 (3) | 0.7055 (9) | 0.0242 (17) | 0.545 (2) |
C46 | 0.9921 (5) | 0.2498 (3) | 0.7140 (9) | 0.0286 (17) | 0.545 (2) |
H46 | 0.9869 | 0.3225 | 0.7212 | 0.034* | 0.545 (2) |
C47 | 1.2761 (9) | 0.0425 (5) | 0.6802 (19) | 0.0406 (10) | 0.545 (2) |
H47A | 1.2633 | −0.0325 | 0.6733 | 0.061* | 0.545 (2) |
H47B | 1.3528 | 0.0623 | 0.7272 | 0.061* | 0.545 (2) |
H47C | 1.3075 | 0.0667 | 0.6307 | 0.061* | 0.545 (2) |
C48 | 1.2632 (8) | 0.2665 (5) | 0.7020 (17) | 0.038 (2) | 0.545 (2) |
H48A | 1.2407 | 0.3395 | 0.7104 | 0.056* | 0.545 (2) |
H48B | 1.2966 | 0.2522 | 0.6484 | 0.056* | 0.545 (2) |
H48C | 1.3426 | 0.2493 | 0.7450 | 0.056* | 0.545 (2) |
N41 | 0.7228 (3) | 0.20946 (19) | 0.7193 (3) | 0.0341 (10) | 0.545 (2) |
N42 | 0.7346 (4) | 0.03409 (19) | 0.7056 (4) | 0.0370 (10) | 0.545 (2) |
O41 | 0.6561 (3) | 0.29187 (18) | 0.7263 (2) | 0.0466 (11) | 0.545 (2) |
O42 | 0.6396 (3) | 0.11456 (18) | 0.7166 (3) | 0.0445 (9) | 0.545 (2) |
C21 | 0.0707 (3) | 0.0891 (2) | 0.9044 (7) | 0.0234 (9) | 0.619 (3) |
C22 | 0.0775 (3) | −0.0187 (2) | 0.8974 (5) | 0.0240 (9) | 0.619 (3) |
C23 | 0.2177 (4) | −0.0654 (3) | 0.8949 (7) | 0.0260 (12) | 0.619 (3) |
H23 | 0.2251 | −0.1380 | 0.8913 | 0.031* | 0.619 (3) |
C24 | 0.3423 (4) | −0.0038 (3) | 0.8976 (7) | 0.0205 (11) | 0.619 (3) |
C25 | 0.3330 (4) | 0.1084 (3) | 0.9067 (7) | 0.0189 (14) | 0.619 (3) |
C26 | 0.1976 (4) | 0.1544 (3) | 0.9073 (11) | 0.0242 (10) | 0.619 (3) |
H26 | 0.1894 | 0.2270 | 0.9096 | 0.029* | 0.619 (3) |
C27 | 0.4906 (6) | −0.0500 (4) | 0.8873 (16) | 0.0330 (8) | 0.619 (3) |
H27A | 0.4802 | −0.1251 | 0.8828 | 0.050* | 0.619 (3) |
H27B | 0.5644 | −0.0270 | 0.9348 | 0.050* | 0.619 (3) |
H27C | 0.5240 | −0.0281 | 0.8375 | 0.050* | 0.619 (3) |
C28 | 0.4730 (5) | 0.1738 (4) | 0.9097 (11) | 0.0306 (19) | 0.619 (3) |
H28A | 0.4478 | 0.2466 | 0.9150 | 0.046* | 0.619 (3) |
H28B | 0.5170 | 0.1583 | 0.8592 | 0.046* | 0.619 (3) |
H28C | 0.5453 | 0.1589 | 0.9568 | 0.046* | 0.619 (3) |
N21 | −0.0722 (3) | 0.11152 (18) | 0.9087 (3) | 0.0290 (8) | 0.619 (3) |
N22 | −0.0565 (3) | −0.06365 (18) | 0.8966 (3) | 0.0339 (10) | 0.619 (3) |
O21 | −0.1410 (3) | 0.19329 (17) | 0.9143 (2) | 0.0429 (9) | 0.619 (3) |
O22 | −0.1544 (2) | 0.01588 (17) | 0.9037 (2) | 0.0371 (8) | 0.619 (3) |
C21A | 0.0644 (5) | 0.0113 (3) | 0.8959 (9) | 0.0240 (9) | 0.381 (3) |
C22A | 0.0698 (5) | 0.1194 (3) | 0.9030 (12) | 0.0234 (9) | 0.381 (3) |
C23A | 0.2084 (7) | 0.1717 (4) | 0.9032 (19) | 0.0242 (10) | 0.381 (3) |
H23A | 0.2151 | 0.2446 | 0.9099 | 0.029* | 0.381 (3) |
C24A | 0.3321 (6) | 0.1151 (5) | 0.8937 (13) | 0.0189 (14) | 0.381 (3) |
C25A | 0.3243 (5) | 0.0025 (5) | 0.8873 (13) | 0.0205 (11) | 0.381 (3) |
C26A | 0.1907 (6) | −0.0489 (4) | 0.8863 (12) | 0.0260 (12) | 0.381 (3) |
H26A | 0.1833 | −0.1218 | 0.8793 | 0.031* | 0.381 (3) |
C27A | 0.4819 (8) | 0.1674 (6) | 0.896 (2) | 0.0306 (19) | 0.381 (3) |
H27D | 0.4704 | 0.2421 | 0.9011 | 0.046* | 0.381 (3) |
H27E | 0.5232 | 0.1466 | 0.8457 | 0.046* | 0.381 (3) |
H27F | 0.5501 | 0.1478 | 0.9433 | 0.046* | 0.381 (3) |
C28A | 0.4668 (8) | −0.0569 (6) | 0.889 (3) | 0.0330 (8) | 0.381 (3) |
H28D | 0.4426 | −0.1307 | 0.8834 | 0.050* | 0.381 (3) |
H28E | 0.5320 | −0.0384 | 0.9405 | 0.050* | 0.381 (3) |
H28F | 0.5184 | −0.0401 | 0.8430 | 0.050* | 0.381 (3) |
N21A | −0.0786 (4) | −0.0168 (2) | 0.8955 (6) | 0.0339 (10) | 0.381 (3) |
N22A | −0.0653 (5) | 0.1589 (2) | 0.9056 (5) | 0.0290 (8) | 0.381 (3) |
O21A | −0.1459 (5) | −0.1013 (2) | 0.8916 (4) | 0.0470 (15) | 0.381 (3) |
O22A | −0.1624 (4) | 0.0755 (2) | 0.9013 (4) | 0.0371 (8) | 0.381 (3) |
C41A | 0.8553 (5) | 0.1095 (3) | 0.7009 (8) | 0.0266 (10) | 0.455 (2) |
C42A | 0.8653 (5) | 0.2175 (3) | 0.7082 (10) | 0.0316 (11) | 0.455 (2) |
C43A | 1.0028 (6) | 0.2668 (3) | 0.7007 (11) | 0.0286 (17) | 0.455 (2) |
H43A | 1.0107 | 0.3396 | 0.7028 | 0.034* | 0.455 (2) |
C44A | 1.1237 (6) | 0.2077 (4) | 0.6903 (11) | 0.0242 (17) | 0.455 (2) |
C45A | 1.1124 (7) | 0.0953 (4) | 0.6867 (14) | 0.0269 (13) | 0.455 (2) |
C46A | 0.9796 (7) | 0.0467 (3) | 0.6928 (16) | 0.0320 (9) | 0.455 (2) |
H46A | 0.9714 | −0.0260 | 0.6916 | 0.038* | 0.455 (2) |
C47A | 1.2743 (9) | 0.2571 (6) | 0.689 (2) | 0.038 (2) | 0.455 (2) |
H47D | 1.2646 | 0.3319 | 0.6905 | 0.056* | 0.455 (2) |
H47E | 1.3134 | 0.2317 | 0.6388 | 0.056* | 0.455 (2) |
H47F | 1.3434 | 0.2401 | 0.7367 | 0.056* | 0.455 (2) |
C48A | 1.2515 (10) | 0.0333 (6) | 0.683 (2) | 0.0406 (10) | 0.455 (2) |
H48D | 1.2260 | −0.0399 | 0.6828 | 0.061* | 0.455 (2) |
H48E | 1.3260 | 0.0547 | 0.7304 | 0.061* | 0.455 (2) |
H48F | 1.2929 | 0.0446 | 0.6325 | 0.061* | 0.455 (2) |
N41A | 0.7140 (4) | 0.0843 (2) | 0.7081 (4) | 0.0370 (10) | 0.455 (2) |
N42A | 0.7343 (5) | 0.2598 (2) | 0.7177 (4) | 0.0341 (10) | 0.455 (2) |
O41A | 0.6438 (4) | 0.0012 (2) | 0.7057 (3) | 0.0527 (14) | 0.455 (2) |
O42A | 0.6350 (4) | 0.1783 (2) | 0.7169 (3) | 0.0445 (9) | 0.455 (2) |
C51A | 1.0041 (7) | 0.2898 (4) | 0.4978 (12) | 0.0234 (7) | 0.190 (3) |
C52A | 0.9953 (7) | 0.1819 (4) | 0.4940 (12) | 0.0236 (7) | 0.190 (3) |
C53A | 0.8580 (11) | 0.1328 (6) | 0.502 (2) | 0.0249 (8) | 0.190 (3) |
H53A | 0.8508 | 0.0601 | 0.5019 | 0.030* | 0.190 (3) |
C54A | 0.7360 (10) | 0.1918 (7) | 0.510 (2) | 0.0223 (8) | 0.190 (3) |
C55A | 0.7463 (8) | 0.3040 (6) | 0.510 (2) | 0.0223 (6) | 0.190 (3) |
C56A | 0.8802 (10) | 0.3526 (5) | 0.507 (2) | 0.0265 (7) | 0.190 (3) |
H56A | 0.8894 | 0.4255 | 0.5101 | 0.032* | 0.190 (3) |
C57A | 0.5856 (18) | 0.1423 (9) | 0.511 (5) | 0.0353 (13) | 0.190 (3) |
H57D | 0.5958 | 0.0677 | 0.5113 | 0.053* | 0.190 (3) |
H57E | 0.5172 | 0.1577 | 0.4627 | 0.053* | 0.190 (3) |
H57F | 0.5453 | 0.1692 | 0.5607 | 0.053* | 0.190 (3) |
C58A | 0.6101 (13) | 0.3667 (9) | 0.521 (3) | 0.0327 (8) | 0.190 (3) |
H58D | 0.6346 | 0.4396 | 0.5190 | 0.049* | 0.190 (3) |
H58E | 0.5786 | 0.3564 | 0.5742 | 0.049* | 0.190 (3) |
H58F | 0.5285 | 0.3448 | 0.4773 | 0.049* | 0.190 (3) |
N51A | 1.1471 (6) | 0.3150 (4) | 0.4949 (10) | 0.0327 (7) | 0.190 (3) |
N52A | 1.1267 (8) | 0.1395 (4) | 0.4853 (9) | 0.0290 (7) | 0.190 (3) |
O51A | 1.2177 (7) | 0.3982 (4) | 0.4986 (6) | 0.039 (3) | 0.190 (3) |
O52A | 1.2269 (6) | 0.2210 (4) | 0.4884 (7) | 0.0333 (6) | 0.190 (3) |
C31A | 0.1331 (5) | 0.3137 (3) | 0.2934 (11) | 0.0265 (10) | 0.402 (3) |
C32A | 0.1404 (5) | 0.4217 (3) | 0.3035 (12) | 0.0249 (9) | 0.402 (3) |
C33A | 0.2806 (7) | 0.4733 (4) | 0.3079 (19) | 0.0263 (9) | 0.402 (3) |
H33A | 0.2880 | 0.5462 | 0.3149 | 0.032* | 0.402 (3) |
C34A | 0.4051 (5) | 0.4163 (5) | 0.3017 (13) | 0.0270 (6) | 0.402 (3) |
C35A | 0.3944 (6) | 0.3037 (5) | 0.2893 (14) | 0.0270 (12) | 0.402 (3) |
C36A | 0.2601 (6) | 0.2529 (4) | 0.2875 (18) | 0.0305 (12) | 0.402 (3) |
H36A | 0.2527 | 0.1799 | 0.2825 | 0.037* | 0.402 (3) |
C37A | 0.5577 (6) | 0.4671 (6) | 0.3156 (13) | 0.0316 (18) | 0.402 (3) |
H37D | 0.5477 | 0.5419 | 0.3185 | 0.047* | 0.402 (3) |
H37E | 0.6124 | 0.4446 | 0.2703 | 0.047* | 0.402 (3) |
H37F | 0.6128 | 0.4479 | 0.3671 | 0.047* | 0.402 (3) |
C38A | 0.5352 (7) | 0.2433 (6) | 0.286 (2) | 0.0368 (14) | 0.402 (3) |
H38D | 0.5102 | 0.1696 | 0.2819 | 0.055* | 0.402 (3) |
H38E | 0.6051 | 0.2615 | 0.3366 | 0.055* | 0.402 (3) |
H38F | 0.5819 | 0.2596 | 0.2389 | 0.055* | 0.402 (3) |
N31A | −0.0102 (4) | 0.2862 (2) | 0.2928 (6) | 0.0366 (11) | 0.402 (3) |
N32A | 0.0055 (5) | 0.4619 (2) | 0.3052 (6) | 0.0305 (9) | 0.402 (3) |
O31A | −0.0781 (5) | 0.2020 (2) | 0.2896 (3) | 0.0481 (15) | 0.402 (3) |
O32A | −0.0928 (4) | 0.3789 (2) | 0.2995 (4) | 0.0393 (9) | 0.402 (3) |
C11A | −0.0768 (6) | 0.4118 (3) | 0.1024 (11) | 0.0230 (10) | 0.454 (2) |
C12A | −0.0671 (6) | 0.5198 (3) | 0.1114 (12) | 0.0257 (10) | 0.454 (2) |
C13A | 0.0722 (9) | 0.5699 (4) | 0.109 (2) | 0.0264 (9) | 0.454 (2) |
H13A | 0.0806 | 0.6428 | 0.1138 | 0.032* | 0.454 (2) |
C14A | 0.1943 (8) | 0.5113 (4) | 0.1004 (18) | 0.0238 (8) | 0.454 (2) |
C15A | 0.1806 (7) | 0.3989 (4) | 0.0886 (16) | 0.0237 (9) | 0.454 (2) |
C16A | 0.0466 (8) | 0.3496 (4) | 0.0908 (18) | 0.0259 (11) | 0.454 (2) |
H16A | 0.0370 | 0.2767 | 0.0848 | 0.031* | 0.454 (2) |
C17A | 0.3433 (13) | 0.5613 (6) | 0.096 (3) | 0.0372 (8) | 0.454 (2) |
H17D | 0.3352 | 0.6362 | 0.1040 | 0.056* | 0.454 (2) |
H17E | 0.3740 | 0.5421 | 0.0425 | 0.056* | 0.454 (2) |
H17F | 0.4180 | 0.5384 | 0.1392 | 0.056* | 0.454 (2) |
C18A | 0.3186 (11) | 0.3368 (6) | 0.081 (3) | 0.0348 (9) | 0.454 (2) |
H18D | 0.2912 | 0.2634 | 0.0744 | 0.052* | 0.454 (2) |
H18E | 0.3916 | 0.3517 | 0.1304 | 0.052* | 0.454 (2) |
H18F | 0.3628 | 0.3550 | 0.0332 | 0.052* | 0.454 (2) |
N11A | −0.2188 (4) | 0.3860 (2) | 0.1075 (4) | 0.0320 (10) | 0.454 (2) |
N12A | −0.1998 (4) | 0.5616 (2) | 0.1178 (4) | 0.0303 (9) | 0.454 (2) |
O11A | −0.2879 (4) | 0.3026 (2) | 0.1059 (3) | 0.0456 (12) | 0.454 (2) |
O12A | −0.2983 (4) | 0.4797 (2) | 0.1171 (3) | 0.0361 (8) | 0.454 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.0274 (16) | 0.027 (3) | 0.0214 (18) | 0.003 (2) | 0.0026 (12) | −0.004 (5) |
C12 | 0.0267 (18) | 0.018 (3) | 0.0251 (15) | 0.001 (2) | 0.0036 (16) | 0.007 (5) |
C13 | 0.030 (3) | 0.0190 (19) | 0.0281 (17) | 0.0035 (18) | −0.003 (4) | 0.008 (4) |
C14 | 0.0247 (18) | 0.0259 (15) | 0.0196 (19) | 0.0028 (12) | −0.002 (2) | 0.0038 (14) |
C15 | 0.0252 (14) | 0.0238 (14) | 0.022 (2) | −0.0038 (11) | 0.0020 (13) | 0.0022 (15) |
C16 | 0.034 (2) | 0.0169 (19) | 0.026 (2) | −0.0013 (16) | 0.000 (3) | −0.001 (4) |
C17 | 0.031 (3) | 0.0380 (19) | 0.0346 (16) | 0.0095 (18) | 0.003 (5) | 0.000 (3) |
C18 | 0.026 (2) | 0.0384 (19) | 0.0474 (17) | −0.0097 (14) | 0.005 (4) | 0.005 (3) |
N11 | 0.0353 (19) | 0.023 (3) | 0.0325 (15) | 0.006 (3) | 0.0050 (13) | 0.001 (3) |
N12 | 0.033 (2) | 0.027 (3) | 0.0362 (16) | −0.002 (2) | 0.0045 (15) | 0.006 (3) |
O11 | 0.035 (2) | 0.035 (2) | 0.061 (2) | 0.0174 (17) | 0.0122 (18) | −0.0011 (17) |
O12 | 0.0265 (14) | 0.037 (2) | 0.0465 (15) | −0.0016 (18) | 0.0083 (12) | 0.006 (2) |
C31 | 0.0270 (16) | 0.020 (3) | 0.0255 (16) | −0.0046 (17) | 0.0019 (11) | −0.004 (4) |
C32 | 0.0347 (18) | 0.019 (3) | 0.0269 (16) | 0.0032 (18) | 0.0024 (15) | 0.011 (4) |
C33 | 0.035 (2) | 0.0246 (19) | 0.031 (3) | 0.0002 (16) | −0.004 (3) | 0.008 (3) |
C34 | 0.0291 (17) | 0.0297 (16) | 0.021 (3) | 0.0069 (12) | −0.0043 (19) | 0.0063 (14) |
C35 | 0.0263 (15) | 0.0329 (16) | 0.0213 (13) | −0.0080 (11) | 0.0023 (11) | 0.0021 (13) |
C36 | 0.0353 (18) | 0.0158 (18) | 0.026 (2) | −0.0055 (14) | 0.000 (2) | −0.002 (3) |
C37 | 0.022 (2) | 0.045 (2) | 0.039 (4) | 0.0000 (17) | −0.006 (4) | −0.005 (2) |
C38 | 0.0285 (19) | 0.041 (2) | 0.024 (5) | −0.0034 (15) | −0.003 (2) | 0.0069 (18) |
N31 | 0.0223 (16) | 0.037 (3) | 0.0321 (14) | −0.005 (2) | 0.0030 (12) | 0.003 (3) |
N32 | 0.030 (2) | 0.040 (3) | 0.0417 (16) | −0.007 (2) | 0.0051 (15) | 0.015 (3) |
O31 | 0.035 (2) | 0.047 (2) | 0.063 (2) | 0.0214 (17) | 0.0108 (17) | 0.0097 (17) |
O32 | 0.0235 (14) | 0.047 (3) | 0.0489 (15) | −0.0082 (18) | 0.0042 (11) | 0.012 (2) |
C51 | 0.0234 (15) | 0.0252 (19) | 0.0215 (13) | 0.0016 (13) | 0.0014 (10) | 0.0009 (17) |
C52 | 0.0255 (16) | 0.0204 (18) | 0.0240 (14) | 0.0001 (13) | 0.0024 (11) | 0.0031 (17) |
C53 | 0.0311 (18) | 0.0182 (15) | 0.0296 (15) | −0.0007 (12) | 0.0024 (19) | 0.0022 (16) |
C54 | 0.0255 (15) | 0.0203 (13) | 0.0206 (12) | 0.0020 (11) | 0.0018 (13) | 0.0012 (10) |
C55 | 0.0224 (13) | 0.0233 (14) | 0.021 (2) | −0.0041 (10) | 0.0029 (10) | 0.0014 (10) |
C56 | 0.0287 (15) | 0.0205 (15) | 0.026 (2) | −0.0005 (12) | 0.0033 (12) | 0.0040 (15) |
C57 | 0.0258 (19) | 0.0321 (17) | 0.0377 (17) | 0.0045 (14) | 0.001 (3) | −0.0058 (17) |
C58 | 0.0312 (17) | 0.0292 (17) | 0.046 (4) | −0.0095 (13) | 0.0104 (17) | 0.001 (2) |
N51 | 0.0265 (14) | 0.0273 (17) | 0.0325 (13) | 0.0005 (15) | 0.0020 (11) | 0.0023 (16) |
N52 | 0.0311 (17) | 0.0252 (19) | 0.0423 (15) | −0.0029 (15) | 0.0066 (12) | 0.0041 (16) |
O51 | 0.0329 (14) | 0.0320 (14) | 0.0572 (16) | 0.0155 (11) | 0.0068 (12) | 0.0046 (11) |
O52 | 0.0225 (12) | 0.0318 (16) | 0.0467 (13) | −0.0022 (11) | 0.0065 (10) | 0.0076 (13) |
C41 | 0.0309 (17) | 0.040 (3) | 0.0249 (17) | 0.008 (2) | 0.0033 (12) | 0.007 (4) |
C42 | 0.0332 (19) | 0.018 (3) | 0.0294 (17) | 0.0074 (19) | 0.0004 (16) | 0.014 (3) |
C43 | 0.041 (2) | 0.0250 (19) | 0.0293 (15) | −0.0011 (17) | 0.001 (3) | 0.007 (3) |
C44 | 0.0278 (18) | 0.0314 (16) | 0.020 (3) | 0.0067 (13) | −0.006 (2) | 0.0069 (14) |
C45 | 0.0345 (15) | 0.0286 (15) | 0.010 (5) | −0.0053 (12) | 0.0019 (13) | 0.0073 (14) |
C46 | 0.049 (2) | 0.028 (2) | 0.012 (4) | 0.0117 (16) | 0.0078 (15) | 0.014 (3) |
C47 | 0.041 (3) | 0.044 (2) | 0.037 (2) | 0.0088 (19) | 0.006 (4) | 0.001 (3) |
C48 | 0.042 (2) | 0.039 (2) | 0.033 (8) | −0.0066 (16) | 0.0104 (19) | −0.001 (3) |
N41 | 0.045 (2) | 0.023 (3) | 0.0361 (16) | 0.008 (3) | 0.0067 (14) | 0.007 (3) |
N42 | 0.046 (2) | 0.020 (3) | 0.0451 (18) | −0.004 (3) | 0.0077 (17) | 0.001 (3) |
O41 | 0.040 (2) | 0.032 (2) | 0.068 (3) | 0.0159 (17) | 0.0092 (19) | 0.0027 (18) |
O42 | 0.0329 (16) | 0.043 (2) | 0.0580 (17) | −0.008 (2) | 0.0080 (13) | 0.005 (3) |
C21 | 0.0235 (15) | 0.024 (3) | 0.0227 (14) | −0.0008 (16) | 0.0015 (10) | 0.004 (3) |
C22 | 0.0252 (16) | 0.021 (2) | 0.0259 (14) | −0.0029 (16) | 0.0006 (13) | 0.009 (3) |
C23 | 0.028 (2) | 0.0210 (18) | 0.027 (3) | 0.0003 (15) | −0.007 (3) | 0.011 (2) |
C24 | 0.0227 (16) | 0.0218 (14) | 0.015 (3) | 0.0025 (11) | −0.0058 (19) | 0.0031 (13) |
C25 | 0.0229 (13) | 0.0260 (14) | 0.009 (4) | −0.0042 (11) | 0.0039 (11) | 0.0054 (13) |
C26 | 0.0284 (16) | 0.0168 (17) | 0.028 (2) | −0.0009 (13) | 0.0047 (15) | 0.004 (3) |
C27 | 0.025 (2) | 0.0382 (18) | 0.0355 (17) | 0.0048 (15) | 0.004 (4) | −0.0011 (19) |
C28 | 0.0288 (16) | 0.0345 (17) | 0.029 (6) | −0.0103 (13) | 0.0126 (15) | −0.0049 (18) |
N21 | 0.0277 (16) | 0.026 (3) | 0.0355 (15) | 0.006 (2) | 0.0056 (12) | 0.014 (2) |
N22 | 0.031 (2) | 0.031 (3) | 0.0393 (16) | −0.006 (2) | 0.0015 (15) | 0.007 (3) |
O21 | 0.0293 (19) | 0.0361 (19) | 0.065 (2) | 0.0151 (15) | 0.0087 (16) | 0.0090 (16) |
O22 | 0.0188 (13) | 0.042 (2) | 0.0518 (15) | −0.0082 (16) | 0.0063 (11) | 0.013 (2) |
C21A | 0.0252 (16) | 0.021 (2) | 0.0259 (14) | −0.0029 (16) | 0.0006 (13) | 0.009 (3) |
C22A | 0.0235 (15) | 0.024 (3) | 0.0227 (14) | −0.0008 (16) | 0.0015 (10) | 0.004 (3) |
C23A | 0.0284 (16) | 0.0168 (17) | 0.028 (2) | −0.0009 (13) | 0.0047 (15) | 0.004 (3) |
C24A | 0.0229 (13) | 0.0260 (14) | 0.009 (4) | −0.0042 (11) | 0.0039 (11) | 0.0054 (13) |
C25A | 0.0227 (16) | 0.0218 (14) | 0.015 (3) | 0.0025 (11) | −0.0058 (19) | 0.0031 (13) |
C26A | 0.028 (2) | 0.0210 (18) | 0.027 (3) | 0.0003 (15) | −0.007 (3) | 0.011 (2) |
C27A | 0.0288 (16) | 0.0345 (17) | 0.029 (6) | −0.0103 (13) | 0.0126 (15) | −0.0049 (18) |
C28A | 0.025 (2) | 0.0382 (18) | 0.0355 (17) | 0.0048 (15) | 0.004 (4) | −0.0011 (19) |
N21A | 0.031 (2) | 0.031 (3) | 0.0393 (16) | −0.006 (2) | 0.0015 (15) | 0.007 (3) |
N22A | 0.0277 (16) | 0.026 (3) | 0.0355 (15) | 0.006 (2) | 0.0056 (12) | 0.014 (2) |
O21A | 0.038 (4) | 0.029 (3) | 0.075 (4) | −0.015 (2) | 0.007 (3) | 0.012 (3) |
O22A | 0.0188 (13) | 0.042 (2) | 0.0518 (15) | −0.0082 (16) | 0.0063 (11) | 0.013 (2) |
C41A | 0.0332 (19) | 0.018 (3) | 0.0294 (17) | 0.0074 (19) | 0.0004 (16) | 0.014 (3) |
C42A | 0.0309 (17) | 0.040 (3) | 0.0249 (17) | 0.008 (2) | 0.0033 (12) | 0.007 (4) |
C43A | 0.049 (2) | 0.028 (2) | 0.012 (4) | 0.0117 (16) | 0.0078 (15) | 0.014 (3) |
C44A | 0.0345 (15) | 0.0286 (15) | 0.010 (5) | −0.0053 (12) | 0.0019 (13) | 0.0073 (14) |
C45A | 0.0278 (18) | 0.0314 (16) | 0.020 (3) | 0.0067 (13) | −0.006 (2) | 0.0069 (14) |
C46A | 0.041 (2) | 0.0250 (19) | 0.0293 (15) | −0.0011 (17) | 0.001 (3) | 0.007 (3) |
C47A | 0.042 (2) | 0.039 (2) | 0.033 (8) | −0.0066 (16) | 0.0104 (19) | −0.001 (3) |
C48A | 0.041 (3) | 0.044 (2) | 0.037 (2) | 0.0088 (19) | 0.006 (4) | 0.001 (3) |
N41A | 0.046 (2) | 0.020 (3) | 0.0451 (18) | −0.004 (3) | 0.0077 (17) | 0.001 (3) |
N42A | 0.045 (2) | 0.023 (3) | 0.0361 (16) | 0.008 (3) | 0.0067 (14) | 0.007 (3) |
O41A | 0.040 (3) | 0.041 (3) | 0.079 (3) | −0.012 (2) | 0.012 (3) | 0.013 (2) |
O42A | 0.0329 (16) | 0.043 (2) | 0.0580 (17) | −0.008 (2) | 0.0080 (13) | 0.005 (3) |
C51A | 0.0255 (16) | 0.0204 (18) | 0.0240 (14) | 0.0001 (13) | 0.0024 (11) | 0.0031 (17) |
C52A | 0.0234 (15) | 0.0252 (19) | 0.0215 (13) | 0.0016 (13) | 0.0014 (10) | 0.0009 (17) |
C53A | 0.0287 (15) | 0.0205 (15) | 0.026 (2) | −0.0005 (12) | 0.0033 (12) | 0.0040 (15) |
C54A | 0.0224 (13) | 0.0233 (14) | 0.021 (2) | −0.0041 (10) | 0.0029 (10) | 0.0014 (10) |
C55A | 0.0255 (15) | 0.0203 (13) | 0.0206 (12) | 0.0020 (11) | 0.0018 (13) | 0.0012 (10) |
C56A | 0.0311 (18) | 0.0182 (15) | 0.0296 (15) | −0.0007 (12) | 0.0024 (19) | 0.0022 (16) |
C57A | 0.0312 (17) | 0.0292 (17) | 0.046 (4) | −0.0095 (13) | 0.0104 (17) | 0.001 (2) |
C58A | 0.0258 (19) | 0.0321 (17) | 0.0377 (17) | 0.0045 (14) | 0.001 (3) | −0.0058 (17) |
N51A | 0.0311 (17) | 0.0252 (19) | 0.0423 (15) | −0.0029 (15) | 0.0066 (12) | 0.0041 (16) |
N52A | 0.0265 (14) | 0.0273 (17) | 0.0325 (13) | 0.0005 (15) | 0.0020 (11) | 0.0023 (16) |
O51A | 0.024 (6) | 0.022 (5) | 0.077 (8) | −0.004 (4) | 0.021 (5) | 0.022 (5) |
O52A | 0.0225 (12) | 0.0318 (16) | 0.0467 (13) | −0.0022 (11) | 0.0065 (10) | 0.0076 (13) |
C31A | 0.0347 (18) | 0.019 (3) | 0.0269 (16) | 0.0032 (18) | 0.0024 (15) | 0.011 (4) |
C32A | 0.0270 (16) | 0.020 (3) | 0.0255 (16) | −0.0046 (17) | 0.0019 (11) | −0.004 (4) |
C33A | 0.0353 (18) | 0.0158 (18) | 0.026 (2) | −0.0055 (14) | 0.000 (2) | −0.002 (3) |
C34A | 0.0263 (15) | 0.0329 (16) | 0.0213 (13) | −0.0080 (11) | 0.0023 (11) | 0.0021 (13) |
C35A | 0.0291 (17) | 0.0297 (16) | 0.021 (3) | 0.0069 (12) | −0.0043 (19) | 0.0063 (14) |
C36A | 0.035 (2) | 0.0246 (19) | 0.031 (3) | 0.0002 (16) | −0.004 (3) | 0.008 (3) |
C37A | 0.0285 (19) | 0.041 (2) | 0.024 (5) | −0.0034 (15) | −0.003 (2) | 0.0069 (18) |
C38A | 0.022 (2) | 0.045 (2) | 0.039 (4) | 0.0000 (17) | −0.006 (4) | −0.005 (2) |
N31A | 0.030 (2) | 0.040 (3) | 0.0417 (16) | −0.007 (2) | 0.0051 (15) | 0.015 (3) |
N32A | 0.0223 (16) | 0.037 (3) | 0.0321 (14) | −0.005 (2) | 0.0030 (12) | 0.003 (3) |
O31A | 0.048 (4) | 0.029 (3) | 0.068 (4) | −0.013 (2) | 0.005 (3) | 0.014 (2) |
O32A | 0.0235 (14) | 0.047 (3) | 0.0489 (15) | −0.0082 (18) | 0.0042 (11) | 0.012 (2) |
C11A | 0.0267 (18) | 0.018 (3) | 0.0251 (15) | 0.001 (2) | 0.0036 (16) | 0.007 (5) |
C12A | 0.0274 (16) | 0.027 (3) | 0.0214 (18) | 0.003 (2) | 0.0026 (12) | −0.004 (5) |
C13A | 0.034 (2) | 0.0169 (19) | 0.026 (2) | −0.0013 (16) | 0.000 (3) | −0.001 (4) |
C14A | 0.0252 (14) | 0.0238 (14) | 0.022 (2) | −0.0038 (11) | 0.0020 (13) | 0.0022 (15) |
C15A | 0.0247 (18) | 0.0259 (15) | 0.0196 (19) | 0.0028 (12) | −0.002 (2) | 0.0038 (14) |
C16A | 0.030 (3) | 0.0190 (19) | 0.0281 (17) | 0.0035 (18) | −0.003 (4) | 0.008 (4) |
C17A | 0.026 (2) | 0.0384 (19) | 0.0474 (17) | −0.0097 (14) | 0.005 (4) | 0.005 (3) |
C18A | 0.031 (3) | 0.0380 (19) | 0.0346 (16) | 0.0095 (18) | 0.003 (5) | 0.000 (3) |
N11A | 0.033 (2) | 0.027 (3) | 0.0362 (16) | −0.002 (2) | 0.0045 (15) | 0.006 (3) |
N12A | 0.0353 (19) | 0.023 (3) | 0.0325 (15) | 0.006 (3) | 0.0050 (13) | 0.001 (3) |
O11A | 0.028 (3) | 0.036 (3) | 0.075 (3) | −0.012 (2) | 0.010 (2) | 0.013 (2) |
O12A | 0.0265 (14) | 0.037 (2) | 0.0465 (15) | −0.0016 (18) | 0.0083 (12) | 0.006 (2) |
C11—N11 | 1.335 (3) | C21A—N21A | 1.335 (3) |
C11—C12 | 1.406 (2) | C21A—C22A | 1.406 (2) |
C11—C16 | 1.411 (3) | C21A—C26A | 1.411 (3) |
C12—N12 | 1.334 (3) | C22A—N22A | 1.334 (3) |
C12—C13 | 1.415 (3) | C22A—C23A | 1.415 (3) |
C13—C14 | 1.366 (3) | C23A—C24A | 1.365 (3) |
C13—H13 | 0.9500 | C23A—H23A | 0.9500 |
C14—C15 | 1.466 (2) | C24A—C25A | 1.466 (2) |
C14—C17 | 1.499 (4) | C24A—C27A | 1.499 (4) |
C15—C16 | 1.368 (3) | C25A—C26A | 1.368 (3) |
C15—C18 | 1.507 (3) | C25A—C28A | 1.507 (3) |
C16—H16 | 0.9500 | C26A—H26A | 0.9500 |
C17—H17A | 0.9800 | C27A—H27D | 0.9800 |
C17—H17B | 0.9800 | C27A—H27E | 0.9800 |
C17—H17C | 0.9800 | C27A—H27F | 0.9800 |
C18—H18A | 0.9800 | C28A—H28D | 0.9800 |
C18—H18B | 0.9800 | C28A—H28E | 0.9800 |
C18—H18C | 0.9800 | C28A—H28F | 0.9800 |
N11—O11 | 1.245 (2) | N21A—O21A | 1.245 (2) |
N11—O12 | 1.434 (2) | N21A—O22A | 1.434 (2) |
N12—O12 | 1.379 (2) | N22A—O22A | 1.379 (2) |
C31—N31 | 1.335 (3) | C41A—N41A | 1.335 (3) |
C31—C32 | 1.406 (2) | C41A—C42A | 1.406 (2) |
C31—C36 | 1.411 (3) | C41A—C46A | 1.411 (3) |
C32—N32 | 1.334 (3) | C42A—N42A | 1.334 (3) |
C32—C33 | 1.415 (3) | C42A—C43A | 1.415 (3) |
C33—C34 | 1.365 (3) | C43A—C44A | 1.365 (3) |
C33—H33 | 0.9500 | C43A—H43A | 0.9500 |
C34—C35 | 1.466 (2) | C44A—C45A | 1.466 (2) |
C34—C37 | 1.499 (4) | C44A—C47A | 1.499 (4) |
C35—C36 | 1.368 (3) | C45A—C46A | 1.368 (3) |
C35—C38 | 1.507 (3) | C45A—C48A | 1.507 (3) |
C36—H36 | 0.9500 | C46A—H46A | 0.9500 |
C37—H37A | 0.9800 | C47A—H47D | 0.9800 |
C37—H37B | 0.9800 | C47A—H47E | 0.9800 |
C37—H37C | 0.9800 | C47A—H47F | 0.9800 |
C38—H38A | 0.9800 | C48A—H48D | 0.9800 |
C38—H38B | 0.9800 | C48A—H48E | 0.9800 |
C38—H38C | 0.9800 | C48A—H48F | 0.9800 |
N31—O31 | 1.245 (2) | N41A—O41A | 1.245 (2) |
N31—O32 | 1.434 (2) | N41A—O42A | 1.435 (2) |
N32—O32 | 1.380 (2) | N42A—O42A | 1.380 (2) |
C51—N51 | 1.335 (3) | C51A—N51A | 1.335 (3) |
C51—C52 | 1.406 (2) | C51A—C52A | 1.406 (2) |
C51—C56 | 1.411 (3) | C51A—C56A | 1.411 (3) |
C52—N52 | 1.334 (3) | C52A—N52A | 1.334 (3) |
C52—C53 | 1.415 (3) | C52A—C53A | 1.414 (3) |
C53—C54 | 1.365 (3) | C53A—C54A | 1.366 (3) |
C53—H53 | 0.9500 | C53A—H53A | 0.9500 |
C54—C55 | 1.466 (2) | C54A—C55A | 1.466 (2) |
C54—C57 | 1.499 (3) | C54A—C57A | 1.499 (4) |
C55—C56 | 1.368 (3) | C55A—C56A | 1.368 (3) |
C55—C58 | 1.507 (3) | C55A—C58A | 1.507 (3) |
C56—H56 | 0.9500 | C56A—H56A | 0.9500 |
C57—H57A | 0.9800 | C57A—H57D | 0.9800 |
C57—H57B | 0.9800 | C57A—H57E | 0.9800 |
C57—H57C | 0.9800 | C57A—H57F | 0.9800 |
C58—H58A | 0.9800 | C58A—H58D | 0.9800 |
C58—H58B | 0.9800 | C58A—H58E | 0.9800 |
C58—H58C | 0.9800 | C58A—H58F | 0.9800 |
N51—O51 | 1.245 (2) | N51A—O51A | 1.245 (2) |
N51—O52 | 1.435 (2) | N51A—O52A | 1.435 (2) |
N52—O52 | 1.379 (2) | N52A—O52A | 1.380 (2) |
C41—N41 | 1.335 (3) | C31A—N31A | 1.335 (3) |
C41—C42 | 1.406 (2) | C31A—C32A | 1.406 (2) |
C41—C46 | 1.411 (3) | C31A—C36A | 1.411 (3) |
C42—N42 | 1.334 (3) | C32A—N32A | 1.334 (3) |
C42—C43 | 1.415 (3) | C32A—C33A | 1.414 (3) |
C43—C44 | 1.365 (3) | C33A—C34A | 1.365 (3) |
C43—H43 | 0.9500 | C33A—H33A | 0.9500 |
C44—C45 | 1.466 (2) | C34A—C35A | 1.467 (2) |
C44—C47 | 1.499 (4) | C34A—C37A | 1.499 (4) |
C45—C46 | 1.368 (3) | C35A—C36A | 1.368 (3) |
C45—C48 | 1.507 (3) | C35A—C38A | 1.507 (3) |
C46—H46 | 0.9500 | C36A—H36A | 0.9500 |
C47—H47A | 0.9800 | C37A—H37D | 0.9800 |
C47—H47B | 0.9800 | C37A—H37E | 0.9800 |
C47—H47C | 0.9800 | C37A—H37F | 0.9800 |
C48—H48A | 0.9800 | C38A—H38D | 0.9800 |
C48—H48B | 0.9800 | C38A—H38E | 0.9800 |
C48—H48C | 0.9800 | C38A—H38F | 0.9800 |
N41—O41 | 1.245 (2) | N31A—O31A | 1.245 (2) |
N41—O42 | 1.435 (2) | N31A—O32A | 1.435 (2) |
N42—O42 | 1.380 (2) | N32A—O32A | 1.379 (2) |
C21—N21 | 1.335 (3) | C11A—N11A | 1.335 (3) |
C21—C22 | 1.406 (2) | C11A—C12A | 1.406 (2) |
C21—C26 | 1.411 (3) | C11A—C16A | 1.411 (3) |
C22—N22 | 1.334 (3) | C12A—N12A | 1.334 (3) |
C22—C23 | 1.415 (3) | C12A—C13A | 1.414 (3) |
C23—C24 | 1.365 (3) | C13A—C14A | 1.366 (3) |
C23—H23 | 0.9500 | C13A—H13A | 0.9500 |
C24—C25 | 1.466 (2) | C14A—C15A | 1.466 (2) |
C24—C27 | 1.499 (4) | C14A—C17A | 1.499 (4) |
C25—C26 | 1.368 (3) | C15A—C16A | 1.368 (3) |
C25—C28 | 1.507 (3) | C15A—C18A | 1.507 (3) |
C26—H26 | 0.9500 | C16A—H16A | 0.9500 |
C27—H27A | 0.9800 | C17A—H17D | 0.9800 |
C27—H27B | 0.9800 | C17A—H17E | 0.9800 |
C27—H27C | 0.9800 | C17A—H17F | 0.9800 |
C28—H28A | 0.9800 | C18A—H18D | 0.9800 |
C28—H28B | 0.9800 | C18A—H18E | 0.9800 |
C28—H28C | 0.9800 | C18A—H18F | 0.9800 |
N21—O21 | 1.245 (2) | N11A—O11A | 1.245 (2) |
N21—O22 | 1.434 (2) | N11A—O12A | 1.435 (2) |
N22—O22 | 1.379 (2) | N12A—O12A | 1.379 (2) |
N11—C11—C12 | 106.5 (2) | N21A—C21A—C22A | 106.5 (2) |
N11—C11—C16 | 130.3 (2) | N21A—C21A—C26A | 130.3 (2) |
C12—C11—C16 | 123.1 (2) | C22A—C21A—C26A | 123.1 (2) |
N12—C12—C11 | 112.1 (2) | N22A—C22A—C21A | 112.1 (2) |
N12—C12—C13 | 128.6 (2) | N22A—C22A—C23A | 128.5 (2) |
C11—C12—C13 | 119.3 (2) | C21A—C22A—C23A | 119.3 (2) |
C14—C13—C12 | 118.7 (2) | C24A—C23A—C22A | 118.7 (2) |
C14—C13—H13 | 120.7 | C24A—C23A—H23A | 120.7 |
C12—C13—H13 | 120.7 | C22A—C23A—H23A | 120.7 |
C13—C14—C15 | 121.0 (3) | C23A—C24A—C25A | 121.0 (3) |
C13—C14—C17 | 120.4 (2) | C23A—C24A—C27A | 120.4 (2) |
C15—C14—C17 | 118.5 (3) | C25A—C24A—C27A | 118.4 (3) |
C16—C15—C14 | 120.7 (3) | C26A—C25A—C24A | 120.7 (3) |
C16—C15—C18 | 119.6 (2) | C26A—C25A—C28A | 119.6 (2) |
C14—C15—C18 | 119.5 (3) | C24A—C25A—C28A | 119.5 (3) |
C15—C16—C11 | 117.0 (2) | C25A—C26A—C21A | 117.0 (2) |
C15—C16—H16 | 121.5 | C25A—C26A—H26A | 121.5 |
C11—C16—H16 | 121.5 | C21A—C26A—H26A | 121.5 |
C14—C17—H17A | 109.5 | C24A—C27A—H27D | 109.5 |
C14—C17—H17B | 109.5 | C24A—C27A—H27E | 109.5 |
H17A—C17—H17B | 109.5 | H27D—C27A—H27E | 109.5 |
C14—C17—H17C | 109.5 | C24A—C27A—H27F | 109.5 |
H17A—C17—H17C | 109.5 | H27D—C27A—H27F | 109.5 |
H17B—C17—H17C | 109.5 | H27E—C27A—H27F | 109.5 |
C15—C18—H18A | 109.5 | C25A—C28A—H28D | 109.5 |
C15—C18—H18B | 109.5 | C25A—C28A—H28E | 109.5 |
H18A—C18—H18B | 109.5 | H28D—C28A—H28E | 109.5 |
C15—C18—H18C | 109.5 | C25A—C28A—H28F | 109.5 |
H18A—C18—H18C | 109.5 | H28D—C28A—H28F | 109.5 |
H18B—C18—H18C | 109.5 | H28E—C28A—H28F | 109.5 |
O11—N11—C11 | 133.9 (2) | O21A—N21A—C21A | 133.9 (2) |
O11—N11—O12 | 118.92 (18) | O21A—N21A—O22A | 118.92 (18) |
C11—N11—O12 | 107.20 (17) | C21A—N21A—O22A | 107.20 (17) |
C12—N12—O12 | 105.41 (17) | C22A—N22A—O22A | 105.41 (17) |
N12—O12—N11 | 108.77 (15) | N22A—O22A—N21A | 108.78 (15) |
N31—C31—C32 | 106.5 (2) | N41A—C41A—C42A | 106.5 (2) |
N31—C31—C36 | 130.4 (2) | N41A—C41A—C46A | 130.3 (2) |
C32—C31—C36 | 123.1 (2) | C42A—C41A—C46A | 123.1 (2) |
N32—C32—C31 | 112.1 (2) | N42A—C42A—C41A | 112.1 (2) |
N32—C32—C33 | 128.6 (2) | N42A—C42A—C43A | 128.5 (2) |
C31—C32—C33 | 119.3 (2) | C41A—C42A—C43A | 119.3 (2) |
C34—C33—C32 | 118.7 (2) | C44A—C43A—C42A | 118.7 (2) |
C34—C33—H33 | 120.7 | C44A—C43A—H43A | 120.7 |
C32—C33—H33 | 120.7 | C42A—C43A—H43A | 120.7 |
C33—C34—C35 | 121.0 (3) | C43A—C44A—C45A | 121.1 (3) |
C33—C34—C37 | 120.4 (2) | C43A—C44A—C47A | 120.3 (2) |
C35—C34—C37 | 118.4 (3) | C45A—C44A—C47A | 118.4 (3) |
C36—C35—C34 | 120.8 (3) | C46A—C45A—C44A | 120.8 (3) |
C36—C35—C38 | 119.7 (2) | C46A—C45A—C48A | 119.6 (2) |
C34—C35—C38 | 119.4 (3) | C44A—C45A—C48A | 119.4 (3) |
C35—C36—C31 | 117.0 (2) | C45A—C46A—C41A | 117.0 (2) |
C35—C36—H36 | 121.5 | C45A—C46A—H46A | 121.5 |
C31—C36—H36 | 121.5 | C41A—C46A—H46A | 121.5 |
C34—C37—H37A | 109.5 | C44A—C47A—H47D | 109.5 |
C34—C37—H37B | 109.5 | C44A—C47A—H47E | 109.5 |
H37A—C37—H37B | 109.5 | H47D—C47A—H47E | 109.5 |
C34—C37—H37C | 109.5 | C44A—C47A—H47F | 109.5 |
H37A—C37—H37C | 109.5 | H47D—C47A—H47F | 109.5 |
H37B—C37—H37C | 109.5 | H47E—C47A—H47F | 109.5 |
C35—C38—H38A | 109.5 | C45A—C48A—H48D | 109.5 |
C35—C38—H38B | 109.5 | C45A—C48A—H48E | 109.5 |
H38A—C38—H38B | 109.5 | H48D—C48A—H48E | 109.5 |
C35—C38—H38C | 109.5 | C45A—C48A—H48F | 109.5 |
H38A—C38—H38C | 109.5 | H48D—C48A—H48F | 109.5 |
H38B—C38—H38C | 109.5 | H48E—C48A—H48F | 109.5 |
O31—N31—C31 | 133.8 (2) | O41A—N41A—C41A | 133.9 (2) |
O31—N31—O32 | 118.97 (18) | O41A—N41A—O42A | 118.87 (18) |
C31—N31—O32 | 107.21 (17) | C41A—N41A—O42A | 107.19 (17) |
C32—N32—O32 | 105.40 (17) | C42A—N42A—O42A | 105.42 (17) |
N32—O32—N31 | 108.76 (15) | N42A—O42A—N41A | 108.74 (15) |
N51—C51—C52 | 106.5 (2) | N51A—C51A—C52A | 106.5 (2) |
N51—C51—C56 | 130.4 (2) | N51A—C51A—C56A | 130.3 (2) |
C52—C51—C56 | 123.1 (2) | C52A—C51A—C56A | 123.1 (2) |
N52—C52—C51 | 112.1 (2) | N52A—C52A—C51A | 112.1 (2) |
N52—C52—C53 | 128.6 (2) | N52A—C52A—C53A | 128.6 (2) |
C51—C52—C53 | 119.3 (2) | C51A—C52A—C53A | 119.3 (2) |
C54—C53—C52 | 118.7 (2) | C54A—C53A—C52A | 118.7 (2) |
C54—C53—H53 | 120.7 | C54A—C53A—H53A | 120.7 |
C52—C53—H53 | 120.7 | C52A—C53A—H53A | 120.7 |
C53—C54—C55 | 121.1 (3) | C53A—C54A—C55A | 121.0 (3) |
C53—C54—C57 | 120.4 (2) | C53A—C54A—C57A | 120.3 (2) |
C55—C54—C57 | 118.5 (3) | C55A—C54A—C57A | 118.4 (3) |
C56—C55—C54 | 120.8 (2) | C56A—C55A—C54A | 120.7 (3) |
C56—C55—C58 | 119.7 (2) | C56A—C55A—C58A | 119.6 (2) |
C54—C55—C58 | 119.5 (3) | C54A—C55A—C58A | 119.5 (3) |
C55—C56—C51 | 117.0 (2) | C55A—C56A—C51A | 117.0 (2) |
C55—C56—H56 | 121.5 | C55A—C56A—H56A | 121.5 |
C51—C56—H56 | 121.5 | C51A—C56A—H56A | 121.5 |
C54—C57—H57A | 109.5 | C54A—C57A—H57D | 109.5 |
C54—C57—H57B | 109.5 | C54A—C57A—H57E | 109.5 |
H57A—C57—H57B | 109.5 | H57D—C57A—H57E | 109.5 |
C54—C57—H57C | 109.5 | C54A—C57A—H57F | 109.5 |
H57A—C57—H57C | 109.5 | H57D—C57A—H57F | 109.5 |
H57B—C57—H57C | 109.5 | H57E—C57A—H57F | 109.5 |
C55—C58—H58A | 109.5 | C55A—C58A—H58D | 109.5 |
C55—C58—H58B | 109.5 | C55A—C58A—H58E | 109.5 |
H58A—C58—H58B | 109.5 | H58D—C58A—H58E | 109.5 |
C55—C58—H58C | 109.5 | C55A—C58A—H58F | 109.5 |
H58A—C58—H58C | 109.5 | H58D—C58A—H58F | 109.5 |
H58B—C58—H58C | 109.5 | H58E—C58A—H58F | 109.5 |
O51—N51—C51 | 133.9 (2) | O51A—N51A—C51A | 133.9 (2) |
O51—N51—O52 | 118.89 (17) | O51A—N51A—O52A | 118.91 (18) |
C51—N51—O52 | 107.20 (16) | C51A—N51A—O52A | 107.20 (17) |
C52—N52—O52 | 105.40 (17) | C52A—N52A—O52A | 105.37 (18) |
N52—O52—N51 | 108.77 (14) | N52A—O52A—N51A | 108.74 (15) |
N41—C41—C42 | 106.5 (2) | N31A—C31A—C32A | 106.5 (2) |
N41—C41—C46 | 130.3 (2) | N31A—C31A—C36A | 130.4 (2) |
C42—C41—C46 | 123.1 (2) | C32A—C31A—C36A | 123.1 (2) |
N42—C42—C41 | 112.1 (2) | N32A—C32A—C31A | 112.1 (2) |
N42—C42—C43 | 128.6 (2) | N32A—C32A—C33A | 128.6 (2) |
C41—C42—C43 | 119.3 (2) | C31A—C32A—C33A | 119.3 (2) |
C44—C43—C42 | 118.7 (2) | C34A—C33A—C32A | 118.7 (2) |
C44—C43—H43 | 120.7 | C34A—C33A—H33A | 120.6 |
C42—C43—H43 | 120.7 | C32A—C33A—H33A | 120.6 |
C43—C44—C45 | 121.1 (3) | C33A—C34A—C35A | 121.0 (3) |
C43—C44—C47 | 120.4 (2) | C33A—C34A—C37A | 120.3 (2) |
C45—C44—C47 | 118.5 (3) | C35A—C34A—C37A | 118.4 (3) |
C46—C45—C44 | 120.8 (3) | C36A—C35A—C34A | 120.7 (3) |
C46—C45—C48 | 119.7 (2) | C36A—C35A—C38A | 119.6 (2) |
C44—C45—C48 | 119.5 (3) | C34A—C35A—C38A | 119.4 (3) |
C45—C46—C41 | 117.0 (2) | C35A—C36A—C31A | 117.0 (2) |
C45—C46—H46 | 121.5 | C35A—C36A—H36A | 121.5 |
C41—C46—H46 | 121.5 | C31A—C36A—H36A | 121.5 |
C44—C47—H47A | 109.5 | C34A—C37A—H37D | 109.5 |
C44—C47—H47B | 109.5 | C34A—C37A—H37E | 109.5 |
H47A—C47—H47B | 109.5 | H37D—C37A—H37E | 109.5 |
C44—C47—H47C | 109.5 | C34A—C37A—H37F | 109.5 |
H47A—C47—H47C | 109.5 | H37D—C37A—H37F | 109.5 |
H47B—C47—H47C | 109.5 | H37E—C37A—H37F | 109.5 |
C45—C48—H48A | 109.5 | C35A—C38A—H38D | 109.5 |
C45—C48—H48B | 109.5 | C35A—C38A—H38E | 109.5 |
H48A—C48—H48B | 109.5 | H38D—C38A—H38E | 109.5 |
C45—C48—H48C | 109.5 | C35A—C38A—H38F | 109.5 |
H48A—C48—H48C | 109.5 | H38D—C38A—H38F | 109.5 |
H48B—C48—H48C | 109.5 | H38E—C38A—H38F | 109.5 |
O41—N41—C41 | 133.9 (2) | O31A—N31A—C31A | 133.9 (2) |
O41—N41—O42 | 118.89 (18) | O31A—N31A—O32A | 118.89 (18) |
C41—N41—O42 | 107.22 (17) | C31A—N31A—O32A | 107.19 (17) |
C42—N42—O42 | 105.42 (17) | C32A—N32A—O32A | 105.39 (17) |
N42—O42—N41 | 108.73 (15) | N32A—O32A—N31A | 108.77 (15) |
N21—C21—C22 | 106.5 (2) | N11A—C11A—C12A | 106.5 (2) |
N21—C21—C26 | 130.4 (2) | N11A—C11A—C16A | 130.4 (2) |
C22—C21—C26 | 123.1 (2) | C12A—C11A—C16A | 123.1 (2) |
N22—C22—C21 | 112.1 (2) | N12A—C12A—C11A | 112.1 (2) |
N22—C22—C23 | 128.6 (2) | N12A—C12A—C13A | 128.5 (2) |
C21—C22—C23 | 119.3 (2) | C11A—C12A—C13A | 119.3 (2) |
C24—C23—C22 | 118.7 (2) | C14A—C13A—C12A | 118.7 (2) |
C24—C23—H23 | 120.7 | C14A—C13A—H13A | 120.7 |
C22—C23—H23 | 120.7 | C12A—C13A—H13A | 120.7 |
C23—C24—C25 | 121.0 (3) | C13A—C14A—C15A | 121.0 (3) |
C23—C24—C27 | 120.4 (2) | C13A—C14A—C17A | 120.3 (2) |
C25—C24—C27 | 118.5 (3) | C15A—C14A—C17A | 118.5 (3) |
C26—C25—C24 | 120.7 (3) | C16A—C15A—C14A | 120.7 (3) |
C26—C25—C28 | 119.6 (2) | C16A—C15A—C18A | 119.6 (2) |
C24—C25—C28 | 119.5 (3) | C14A—C15A—C18A | 119.4 (3) |
C25—C26—C21 | 117.0 (2) | C15A—C16A—C11A | 117.0 (2) |
C25—C26—H26 | 121.5 | C15A—C16A—H16A | 121.5 |
C21—C26—H26 | 121.5 | C11A—C16A—H16A | 121.5 |
C24—C27—H27A | 109.5 | C14A—C17A—H17D | 109.5 |
C24—C27—H27B | 109.5 | C14A—C17A—H17E | 109.5 |
H27A—C27—H27B | 109.5 | H17D—C17A—H17E | 109.5 |
C24—C27—H27C | 109.5 | C14A—C17A—H17F | 109.5 |
H27A—C27—H27C | 109.5 | H17D—C17A—H17F | 109.5 |
H27B—C27—H27C | 109.5 | H17E—C17A—H17F | 109.5 |
C25—C28—H28A | 109.5 | C15A—C18A—H18D | 109.5 |
C25—C28—H28B | 109.5 | C15A—C18A—H18E | 109.5 |
H28A—C28—H28B | 109.5 | H18D—C18A—H18E | 109.5 |
C25—C28—H28C | 109.5 | C15A—C18A—H18F | 109.5 |
H28A—C28—H28C | 109.5 | H18D—C18A—H18F | 109.5 |
H28B—C28—H28C | 109.5 | H18E—C18A—H18F | 109.5 |
O21—N21—C21 | 133.9 (2) | O11A—N11A—C11A | 133.9 (2) |
O21—N21—O22 | 118.91 (18) | O11A—N11A—O12A | 118.89 (18) |
C21—N21—O22 | 107.21 (17) | C11A—N11A—O12A | 107.19 (17) |
C22—N22—O22 | 105.41 (17) | C12A—N12A—O12A | 105.39 (17) |
N22—O22—N21 | 108.77 (15) | N12A—O12A—N11A | 108.76 (15) |
N11—C11—C12—N12 | 1.9 (14) | N21A—C21A—C22A—N22A | −1.0 (16) |
C16—C11—C12—N12 | −179.5 (15) | C26A—C21A—C22A—N22A | 175.5 (15) |
N11—C11—C12—C13 | −177.8 (16) | N21A—C21A—C22A—C23A | −178.7 (13) |
C16—C11—C12—C13 | 1 (2) | C26A—C21A—C22A—C23A | −2 (2) |
N12—C12—C13—C14 | −178.9 (14) | N22A—C22A—C23A—C24A | −175 (2) |
C11—C12—C13—C14 | 1 (2) | C21A—C22A—C23A—C24A | 2 (2) |
C12—C13—C14—C15 | −3 (2) | C22A—C23A—C24A—C25A | −3 (2) |
C12—C13—C14—C17 | −178.6 (18) | C22A—C23A—C24A—C27A | −178.2 (18) |
C13—C14—C15—C16 | 4 (2) | C23A—C24A—C25A—C26A | 3.6 (18) |
C17—C14—C15—C16 | 179.6 (16) | C27A—C24A—C25A—C26A | 178.9 (18) |
C13—C14—C15—C18 | 179.2 (16) | C23A—C24A—C25A—C28A | −172 (2) |
C17—C14—C15—C18 | −5.0 (19) | C27A—C24A—C25A—C28A | 4 (2) |
C14—C15—C16—C11 | −2 (2) | C24A—C25A—C26A—C21A | −3.3 (18) |
C18—C15—C16—C11 | −177.6 (19) | C28A—C25A—C26A—C21A | 172 (2) |
N11—C11—C16—C15 | 178.3 (16) | N21A—C21A—C26A—C25A | 178.3 (14) |
C12—C11—C16—C15 | 0 (2) | C22A—C21A—C26A—C25A | 3 (2) |
C12—C11—N11—O11 | 179.8 (8) | C22A—C21A—N21A—O21A | −179.0 (13) |
C16—C11—N11—O11 | 1 (2) | C26A—C21A—N21A—O21A | 5 (2) |
C12—C11—N11—O12 | −1.6 (11) | C22A—C21A—N21A—O22A | 0.8 (13) |
C16—C11—N11—O12 | 179.9 (16) | C26A—C21A—N21A—O22A | −175.4 (15) |
C11—C12—N12—O12 | −1.3 (12) | C21A—C22A—N22A—O22A | 0.8 (15) |
C13—C12—N12—O12 | 178.4 (17) | C23A—C22A—N22A—O22A | 178.1 (14) |
C12—N12—O12—N11 | 0.2 (9) | C22A—N22A—O22A—N21A | −0.2 (12) |
O11—N11—O12—N12 | 179.7 (5) | O21A—N21A—O22A—N22A | 179.5 (8) |
C11—N11—O12—N12 | 0.9 (9) | C21A—N21A—O22A—N22A | −0.4 (11) |
N31—C31—C32—N32 | 2.4 (11) | N41A—C41A—C42A—N42A | −1.5 (15) |
C36—C31—C32—N32 | −179.6 (12) | C46A—C41A—C42A—N42A | −178.0 (15) |
N31—C31—C32—C33 | −178.5 (12) | N41A—C41A—C42A—C43A | −178.2 (12) |
C36—C31—C32—C33 | −0.4 (18) | C46A—C41A—C42A—C43A | 5 (2) |
N32—C32—C33—C34 | −178.1 (11) | N42A—C42A—C43A—C44A | −179.2 (14) |
C31—C32—C33—C34 | 2.9 (19) | C41A—C42A—C43A—C44A | −3 (2) |
C32—C33—C34—C35 | −3.7 (16) | C42A—C43A—C44A—C45A | 0.2 (19) |
C32—C33—C34—C37 | −179.0 (13) | C42A—C43A—C44A—C47A | −175.0 (17) |
C33—C34—C35—C36 | 2.1 (12) | C43A—C44A—C45A—C46A | 0.7 (19) |
C37—C34—C35—C36 | 177.4 (11) | C47A—C44A—C45A—C46A | 176 (2) |
C33—C34—C35—C38 | −173.9 (13) | C43A—C44A—C45A—C48A | −174.6 (18) |
C37—C34—C35—C38 | 1.4 (11) | C47A—C44A—C45A—C48A | 0.7 (18) |
C34—C35—C36—C31 | 0.4 (14) | C44A—C45A—C46A—C41A | 1 (2) |
C38—C35—C36—C31 | 176.4 (13) | C48A—C45A—C46A—C41A | 176.6 (19) |
N31—C31—C36—C35 | 176.4 (11) | N41A—C41A—C46A—C45A | −179.9 (15) |
C32—C31—C36—C35 | −1.2 (18) | C42A—C41A—C46A—C45A | −4 (2) |
C32—C31—N31—O31 | 178.5 (7) | C42A—C41A—N41A—O41A | 179.3 (10) |
C36—C31—N31—O31 | 0.6 (19) | C46A—C41A—N41A—O41A | −5 (2) |
C32—C31—N31—O32 | −1.8 (10) | C42A—C41A—N41A—O42A | 2.1 (12) |
C36—C31—N31—O32 | −179.7 (13) | C46A—C41A—N41A—O42A | 178.3 (15) |
C31—C32—N32—O32 | −1.8 (10) | C41A—C42A—N42A—O42A | 0.1 (13) |
C33—C32—N32—O32 | 179.2 (13) | C43A—C42A—N42A—O42A | 176.5 (13) |
C32—N32—O32—N31 | 0.6 (7) | C42A—N42A—O42A—N41A | 1.2 (10) |
O31—N31—O32—N32 | −179.4 (5) | O41A—N41A—O42A—N42A | −179.9 (6) |
C31—N31—O32—N32 | 0.8 (8) | C41A—N41A—O42A—N42A | −2.2 (10) |
N51—C51—C52—N52 | −0.4 (4) | N51A—C51A—C52A—N52A | −2.7 (17) |
C56—C51—C52—N52 | −179.4 (5) | C56A—C51A—C52A—N52A | 179.9 (19) |
N51—C51—C52—C53 | 179.5 (4) | N51A—C51A—C52A—C53A | 175 (2) |
C56—C51—C52—C53 | 0.5 (6) | C56A—C51A—C52A—C53A | −2 (3) |
N52—C52—C53—C54 | 179.5 (5) | N52A—C52A—C53A—C54A | −180 (2) |
C51—C52—C53—C54 | −0.4 (8) | C51A—C52A—C53A—C54A | 3 (3) |
C52—C53—C54—C55 | −0.1 (8) | C52A—C53A—C54A—C55A | 0 (3) |
C52—C53—C54—C57 | −179.2 (6) | C52A—C53A—C54A—C57A | 175 (3) |
C53—C54—C55—C56 | 0.5 (8) | C53A—C54A—C55A—C56A | −3 (3) |
C57—C54—C55—C56 | 179.7 (6) | C57A—C54A—C55A—C56A | −178 (3) |
C53—C54—C55—C58 | 179.8 (7) | C53A—C54A—C55A—C58A | −179 (2) |
C57—C54—C55—C58 | −1.1 (7) | C57A—C54A—C55A—C58A | 6 (3) |
C54—C55—C56—C51 | −0.5 (8) | C54A—C55A—C56A—C51A | 4 (3) |
C58—C55—C56—C51 | −179.7 (7) | C58A—C55A—C56A—C51A | 179 (2) |
N51—C51—C56—C55 | −178.8 (5) | N51A—C51A—C56A—C55A | −178 (2) |
C52—C51—C56—C55 | −0.1 (7) | C52A—C51A—C56A—C55A | −1 (3) |
C52—C51—N51—O51 | 179.9 (4) | C52A—C51A—N51A—O51A | −177.5 (18) |
C56—C51—N51—O51 | −1.2 (7) | C56A—C51A—N51A—O51A | 0 (3) |
C52—C51—N51—O52 | 0.2 (4) | C52A—C51A—N51A—O52A | 0.6 (17) |
C56—C51—N51—O52 | 179.0 (5) | C56A—C51A—N51A—O52A | 178 (2) |
C51—C52—N52—O52 | 0.4 (4) | C51A—C52A—N52A—O52A | 3.5 (14) |
C53—C52—N52—O52 | −179.4 (5) | C53A—C52A—N52A—O52A | −174 (2) |
C52—N52—O52—N51 | −0.3 (3) | C52A—N52A—O52A—N51A | −3.0 (14) |
O51—N51—O52—N52 | −179.7 (3) | O51A—N51A—O52A—N52A | 179.9 (14) |
C51—N51—O52—N52 | 0.1 (3) | C51A—N51A—O52A—N52A | 1.5 (16) |
N41—C41—C42—N42 | 0.9 (12) | N31A—C31A—C32A—N32A | −3.1 (18) |
C46—C41—C42—N42 | 177.8 (10) | C36A—C31A—C32A—N32A | 178 (2) |
N41—C41—C42—C43 | 179.0 (12) | N31A—C31A—C32A—C33A | 178.9 (18) |
C46—C41—C42—C43 | −4.0 (17) | C36A—C31A—C32A—C33A | 0 (3) |
N42—C42—C43—C44 | −178.9 (13) | N32A—C32A—C33A—C34A | −177.4 (18) |
C41—C42—C43—C44 | 3.3 (19) | C31A—C32A—C33A—C34A | 0 (3) |
C42—C43—C44—C45 | −1.3 (19) | C32A—C33A—C34A—C35A | 1 (2) |
C42—C43—C44—C47 | −177.4 (16) | C32A—C33A—C34A—C37A | −173 (2) |
C43—C44—C45—C46 | −0.2 (16) | C33A—C34A—C35A—C36A | −3.2 (17) |
C47—C44—C45—C46 | 176.0 (14) | C37A—C34A—C35A—C36A | 171.1 (19) |
C43—C44—C45—C48 | −176.5 (16) | C33A—C34A—C35A—C38A | −177.4 (18) |
C47—C44—C45—C48 | −0.3 (15) | C37A—C34A—C35A—C38A | −3.1 (17) |
C44—C45—C46—C41 | −0.4 (15) | C34A—C35A—C36A—C31A | 4 (2) |
C48—C45—C46—C41 | 175.9 (14) | C38A—C35A—C36A—C31A | 178 (2) |
N41—C41—C46—C45 | 178.7 (12) | N31A—C31A—C36A—C35A | 179.5 (17) |
C42—C41—C46—C45 | 2.5 (16) | C32A—C31A—C36A—C35A | −2 (3) |
C42—C41—N41—O41 | −178.4 (7) | C32A—C31A—N31A—O31A | −176.1 (13) |
C46—C41—N41—O41 | 4.9 (18) | C36A—C31A—N31A—O31A | 2 (3) |
C42—C41—N41—O42 | 0.1 (10) | C32A—C31A—N31A—O32A | 2.3 (14) |
C46—C41—N41—O42 | −176.6 (11) | C36A—C31A—N31A—O32A | −179 (2) |
C41—C42—N42—O42 | −1.4 (10) | C31A—C32A—N32A—O32A | 2.5 (17) |
C43—C42—N42—O42 | −179.4 (12) | C33A—C32A—N32A—O32A | −180 (2) |
C42—N42—O42—N41 | 1.4 (8) | C32A—N32A—O32A—N31A | −1.1 (13) |
O41—N41—O42—N42 | 177.8 (5) | O31A—N31A—O32A—N32A | 177.8 (8) |
C41—N41—O42—N42 | −0.9 (8) | C31A—N31A—O32A—N32A | −0.8 (12) |
N21—C21—C22—N22 | 0.5 (9) | N11A—C11A—C12A—N12A | −3.1 (17) |
C26—C21—C22—N22 | 179.5 (8) | C16A—C11A—C12A—N12A | 177 (2) |
N21—C21—C22—C23 | −177.6 (8) | N11A—C11A—C12A—C13A | 179.6 (18) |
C26—C21—C22—C23 | 1.5 (12) | C16A—C11A—C12A—C13A | 0 (3) |
N22—C22—C23—C24 | −179.0 (8) | N12A—C12A—C13A—C14A | −178 (2) |
C21—C22—C23—C24 | −1.3 (12) | C11A—C12A—C13A—C14A | −2 (3) |
C22—C23—C24—C25 | 2.7 (11) | C12A—C13A—C14A—C15A | 4 (3) |
C22—C23—C24—C27 | −174.3 (12) | C12A—C13A—C14A—C17A | 179 (2) |
C23—C24—C25—C26 | −4.2 (11) | C13A—C14A—C15A—C16A | −4 (3) |
C27—C24—C25—C26 | 172.8 (13) | C17A—C14A—C15A—C16A | −179 (2) |
C23—C24—C25—C28 | 179.9 (10) | C13A—C14A—C15A—C18A | −179 (2) |
C27—C24—C25—C28 | −3.1 (12) | C17A—C14A—C15A—C18A | 6 (2) |
C24—C25—C26—C21 | 4.1 (13) | C14A—C15A—C16A—C11A | 2 (3) |
C28—C25—C26—C21 | −180.0 (10) | C18A—C15A—C16A—C11A | 177 (2) |
N21—C21—C26—C25 | 175.9 (11) | N11A—C11A—C16A—C15A | −179.7 (18) |
C22—C21—C26—C25 | −2.9 (13) | C12A—C11A—C16A—C15A | 0 (3) |
C22—C21—N21—O21 | −179.0 (6) | C12A—C11A—N11A—O11A | −177.7 (11) |
C26—C21—N21—O21 | 2.1 (13) | C16A—C11A—N11A—O11A | 2 (3) |
C22—C21—N21—O22 | −0.4 (8) | C12A—C11A—N11A—O12A | 1.8 (14) |
C26—C21—N21—O22 | −179.3 (8) | C16A—C11A—N11A—O12A | −178 (2) |
C21—C22—N22—O22 | −0.4 (8) | C11A—C12A—N12A—O12A | 3.0 (15) |
C23—C22—N22—O22 | 177.5 (8) | C13A—C12A—N12A—O12A | −180.0 (19) |
C22—N22—O22—N21 | 0.1 (6) | C12A—N12A—O12A—N11A | −1.8 (11) |
O21—N21—O22—N22 | 179.0 (4) | O11A—N11A—O12A—N12A | 179.5 (6) |
C21—N21—O22—N22 | 0.2 (7) | C11A—N11A—O12A—N12A | 0.0 (11) |
C10H8O3 | F(000) = 736 |
Mr = 176.16 | Dx = 1.448 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 3420 reflections |
a = 11.744 (4) Å | θ = 2.8–27.5° |
b = 7.601 (3) Å | µ = 0.11 mm−1 |
c = 18.102 (6) Å | T = 173 K |
V = 1615.9 (10) Å3 | Prism, colorless |
Z = 8 | 0.50 × 0.35 × 0.25 mm |
Bruker SMART 1K CCD area-detector diffractometer | 1857 independent reflections |
Radiation source: fine-focus sealed tube | 1772 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ω scans | θmax = 27.5°, θmin = 2.3° |
Absorption correction: multi-scan SADABS; Sheldrick, 2008; Blessing, 1995 | h = −15→15 |
Tmin = 0.95, Tmax = 0.97 | k = −9→9 |
17411 measured reflections | l = −23→23 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: calc |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.099 | w = 1/[σ2(Fo2) + (0.055P)2 + 0.438P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
1857 reflections | Δρmax = 0.33 e Å−3 |
121 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: 0.084 (4) |
C10H8O3 | V = 1615.9 (10) Å3 |
Mr = 176.16 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 11.744 (4) Å | µ = 0.11 mm−1 |
b = 7.601 (3) Å | T = 173 K |
c = 18.102 (6) Å | 0.50 × 0.35 × 0.25 mm |
Bruker SMART 1K CCD area-detector diffractometer | 1857 independent reflections |
Absorption correction: multi-scan SADABS; Sheldrick, 2008; Blessing, 1995 | 1772 reflections with I > 2σ(I) |
Tmin = 0.95, Tmax = 0.97 | Rint = 0.027 |
17411 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.33 e Å−3 |
1857 reflections | Δρmin = −0.14 e Å−3 |
121 parameters |
x | y | z | Uiso*/Ueq | ||
C1 | 0.05887 (8) | 0.21317 (12) | 0.48258 (5) | 0.0228 (2) | |
C2 | 0.15461 (8) | 0.10774 (13) | 0.48559 (5) | 0.0232 (2) | |
C3 | 0.20234 (8) | 0.05807 (14) | 0.55217 (5) | 0.0256 (2) | |
H3 | 0.2689 | −0.0129 | 0.5535 | 0.031* | |
C4 | 0.15040 (8) | 0.11466 (13) | 0.61746 (5) | 0.0248 (2) | |
C5 | 0.05135 (9) | 0.22036 (13) | 0.61446 (5) | 0.0247 (2) | |
C6 | 0.00614 (8) | 0.27159 (13) | 0.54630 (5) | 0.0248 (2) | |
H6 | −0.0593 | 0.3448 | 0.5439 | 0.030* | |
C7 | 0.02919 (8) | 0.23818 (13) | 0.40411 (5) | 0.0252 (2) | |
C8 | 0.18618 (9) | 0.06185 (13) | 0.40921 (5) | 0.0261 (2) | |
C9 | 0.19891 (9) | 0.05791 (16) | 0.69046 (6) | 0.0330 (3) | |
H9A | 0.1485 | −0.0296 | 0.7131 | 0.049* | |
H9B | 0.2054 | 0.1602 | 0.7232 | 0.049* | |
H9C | 0.2744 | 0.0062 | 0.6828 | 0.049* | |
C10 | −0.00697 (10) | 0.27670 (16) | 0.68445 (6) | 0.0328 (3) | |
H10A | −0.0751 | 0.3452 | 0.6722 | 0.049* | |
H10B | 0.0451 | 0.3492 | 0.7138 | 0.049* | |
H10C | −0.0290 | 0.1725 | 0.7129 | 0.049* | |
O11 | −0.04487 (7) | 0.31905 (11) | 0.37500 (4) | 0.0350 (2) | |
O12 | 0.26160 (7) | −0.02644 (12) | 0.38547 (4) | 0.0376 (2) | |
O13 | 0.10748 (6) | 0.14088 (9) | 0.36216 (4) | 0.0276 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0253 (4) | 0.0229 (5) | 0.0203 (5) | −0.0029 (4) | −0.0010 (3) | 0.0011 (3) |
C2 | 0.0250 (5) | 0.0237 (5) | 0.0210 (5) | −0.0023 (4) | 0.0025 (3) | −0.0004 (3) |
C3 | 0.0258 (5) | 0.0267 (5) | 0.0242 (5) | 0.0004 (4) | 0.0002 (4) | 0.0023 (4) |
C4 | 0.0273 (5) | 0.0258 (5) | 0.0214 (5) | −0.0050 (4) | −0.0009 (4) | 0.0030 (3) |
C5 | 0.0276 (5) | 0.0258 (5) | 0.0206 (5) | −0.0045 (4) | 0.0023 (4) | −0.0009 (3) |
C6 | 0.0258 (5) | 0.0256 (5) | 0.0231 (5) | 0.0008 (4) | 0.0009 (4) | −0.0009 (3) |
C7 | 0.0286 (5) | 0.0255 (5) | 0.0215 (5) | −0.0030 (4) | −0.0001 (4) | −0.0006 (4) |
C8 | 0.0294 (5) | 0.0270 (5) | 0.0219 (5) | −0.0021 (4) | 0.0016 (4) | −0.0003 (4) |
C9 | 0.0364 (6) | 0.0406 (6) | 0.0220 (5) | −0.0008 (5) | −0.0023 (4) | 0.0068 (4) |
C10 | 0.0371 (5) | 0.0390 (6) | 0.0222 (5) | 0.0003 (5) | 0.0057 (4) | −0.0028 (4) |
O11 | 0.0380 (4) | 0.0399 (5) | 0.0271 (4) | 0.0065 (3) | −0.0063 (3) | 0.0027 (3) |
O12 | 0.0393 (5) | 0.0434 (5) | 0.0300 (4) | 0.0101 (4) | 0.0076 (3) | −0.0040 (3) |
O13 | 0.0329 (4) | 0.0300 (4) | 0.0198 (4) | −0.0004 (3) | 0.0001 (3) | −0.0016 (3) |
C1—C2 | 1.3819 (14) | C6—H6 | 0.9500 |
C1—C6 | 1.3825 (13) | C7—O11 | 1.1883 (13) |
C1—C7 | 1.4748 (14) | C7—O13 | 1.4032 (12) |
C2—C3 | 1.3818 (14) | C8—O12 | 1.1915 (13) |
C2—C8 | 1.4734 (14) | C8—O13 | 1.3929 (13) |
C3—C4 | 1.3980 (14) | C9—H9A | 0.9800 |
C3—H3 | 0.9500 | C9—H9B | 0.9800 |
C4—C5 | 1.4147 (15) | C9—H9C | 0.9800 |
C4—C9 | 1.5023 (13) | C10—H10A | 0.9800 |
C5—C6 | 1.3984 (14) | C10—H10B | 0.9800 |
C5—C10 | 1.5027 (14) | C10—H10C | 0.9800 |
C2—C1—C6 | 121.19 (9) | O11—C7—C1 | 131.82 (9) |
C2—C1—C7 | 107.76 (8) | O13—C7—C1 | 107.36 (8) |
C6—C1—C7 | 131.02 (9) | O12—C8—O13 | 121.05 (9) |
C3—C2—C1 | 121.53 (9) | O12—C8—C2 | 131.21 (10) |
C3—C2—C8 | 130.68 (9) | O13—C8—C2 | 107.74 (8) |
C1—C2—C8 | 107.76 (8) | C4—C9—H9A | 109.5 |
C2—C3—C4 | 118.45 (10) | C4—C9—H9B | 109.5 |
C2—C3—H3 | 120.8 | H9A—C9—H9B | 109.5 |
C4—C3—H3 | 120.8 | C4—C9—H9C | 109.5 |
C3—C4—C5 | 120.06 (9) | H9A—C9—H9C | 109.5 |
C3—C4—C9 | 119.33 (10) | H9B—C9—H9C | 109.5 |
C5—C4—C9 | 120.58 (9) | C5—C10—H10A | 109.5 |
C6—C5—C4 | 120.29 (9) | C5—C10—H10B | 109.5 |
C6—C5—C10 | 119.44 (9) | H10A—C10—H10B | 109.5 |
C4—C5—C10 | 120.28 (9) | C5—C10—H10C | 109.5 |
C1—C6—C5 | 118.46 (9) | H10A—C10—H10C | 109.5 |
C1—C6—H6 | 120.8 | H10B—C10—H10C | 109.5 |
C5—C6—H6 | 120.8 | C8—O13—C7 | 109.34 (8) |
O11—C7—O13 | 120.82 (9) | ||
C6—C1—C2—C3 | −0.76 (15) | C4—C5—C6—C1 | 1.50 (15) |
C7—C1—C2—C3 | −178.93 (9) | C10—C5—C6—C1 | −177.77 (9) |
C6—C1—C2—C8 | 177.29 (9) | C2—C1—C7—O11 | −179.21 (11) |
C7—C1—C2—C8 | −0.88 (11) | C6—C1—C7—O11 | 2.87 (19) |
C1—C2—C3—C4 | 1.03 (15) | C2—C1—C7—O13 | 1.77 (10) |
C8—C2—C3—C4 | −176.52 (9) | C6—C1—C7—O13 | −176.15 (10) |
C2—C3—C4—C5 | −0.04 (15) | C3—C2—C8—O12 | −1.61 (19) |
C2—C3—C4—C9 | 178.26 (9) | C1—C2—C8—O12 | −179.42 (11) |
C3—C4—C5—C6 | −1.23 (15) | C3—C2—C8—O13 | 177.49 (10) |
C9—C4—C5—C6 | −179.51 (9) | C1—C2—C8—O13 | −0.33 (11) |
C3—C4—C5—C10 | 178.03 (9) | O12—C8—O13—C7 | −179.33 (10) |
C9—C4—C5—C10 | −0.25 (15) | C2—C8—O13—C7 | 1.46 (10) |
C2—C1—C6—C5 | −0.52 (15) | O11—C7—O13—C8 | 178.86 (10) |
C7—C1—C6—C5 | 177.16 (9) | C1—C7—O13—C8 | −1.99 (10) |
Experimental details
(Z2) | (Z4) | (Z6) | (Z10) | |
Crystal data | ||||
Chemical formula | C8H8N2O2 | C8H8N2O2 | C8H8N2O2 | C8H8N2O2 |
Mr | 164.16 | 164.16 | 164.16 | 164.16 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 173 | 173 | 173 | 173 |
a, b, c (Å) | 3.9506 (12), 8.264 (3), 12.045 (4) | 7.3643 (9), 9.0332 (11), 11.6675 (14) | 9.0070 (11), 11.1331 (13), 12.9526 (15) | 9.0136 (18), 13.064 (3), 16.567 (3) |
α, β, γ (°) | 78.842 (4), 83.180 (4), 86.990 (4) | 89.264 (2), 83.419 (2), 87.027 (2) | 65.173 (2), 80.629 (2), 79.862 (2) | 95.055 (4), 97.969 (4), 90.742 (4) |
V (Å3) | 382.9 (2) | 769.99 (16) | 1154.6 (2) | 1923.9 (7) |
Z | 2 | 4 | 6 | 10 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.11 | 0.11 | 0.11 | 0.11 |
Crystal size (mm) | 0.50 × 0.13 × 0.06 | 0.35 × 0.30 × 0.25 | 0.35 × 0.25 × 0.20 | 0.40 × 0.35 × 0.20 |
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, 2008; Blessing, 1995 | Multi-scan SADABS; Sheldrick, 2008; Blessing, 1995 | Multi-scan SADABS: Sheldrick, 2008; Blessing, 1995 | Multi-scan SADABS: Sheldrick, 2008; Blessing, 1995 |
Tmin, Tmax | 0.94, 0.99 | 0.96, 0.97 | 0.96, 0.98 | 0.96, 0.98 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4353, 1713, 1379 | 8977, 3498, 2286 | 13249, 5157, 3457 | 22419, 8722, 3791 |
Rint | 0.031 | 0.024 | 0.020 | 0.054 |
(sin θ/λ)max (Å−1) | 0.650 | 0.650 | 0.650 | 0.651 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.156, 1.10 | 0.049, 0.140, 1.05 | 0.052, 0.168, 1.03 | 0.114, 0.338, 0.97 |
No. of reflections | 1713 | 3498 | 5157 | 8722 |
No. of parameters | 153 | 304 | 454 | 756 |
No. of restraints | 32 | 192 | 480 | 1440 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.22 | 0.19, −0.15 | 0.40, −0.23 | 1.18, −0.39 |
(Me2PA) | |
Crystal data | |
Chemical formula | C10H8O3 |
Mr | 176.16 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 173 |
a, b, c (Å) | 11.744 (4), 7.601 (3), 18.102 (6) |
α, β, γ (°) | 90, 90, 90 |
V (Å3) | 1615.9 (10) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.50 × 0.35 × 0.25 |
Data collection | |
Diffractometer | Bruker SMART 1K CCD area-detector diffractometer |
Absorption correction | Multi-scan SADABS; Sheldrick, 2008; Blessing, 1995 |
Tmin, Tmax | 0.95, 0.97 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17411, 1857, 1772 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.651 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.099, 1.06 |
No. of reflections | 1857 |
No. of parameters | 121 |
No. of restraints | 0 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.33, −0.14 |
Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SAINT, SHELXTL (Sheldrick, 2008), SHELXTL.
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