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5,6-Dimethylbenzofurazan 1-oxide (Me2BF), C8H8N2O2, occurs in four polymorphic forms that are polytypes of each other. Each polymorph of Me2BF contains molecules disordered about pseudo-twofold axes and arranged head-to-tail in ribbons, with the ribbons forming approximately planar layers held together by weak C—H...N and C—H...O interactions. Adjacent layers interact in different ways in the different polymorphs. In addition to twinning in the individual polymorphs, four examples of allotwining, that is, oriented overgrowths between different polymorphs, were found.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768112037457/ps5015sup1.cif
Contains datablocks Z2, Z4, Z6, Z10, Me2PA

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768112037457/ps5015Z2sup2.hkl
Contains datablock fin

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768112037457/ps5015Z4sup3.hkl
Contains datablock Z4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768112037457/ps5015Z6sup4.hkl
Contains datablock Z6

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768112037457/ps5015Z10sup5.hkl
Contains datablock fin

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768112037457/ps5015Me2PAsup6.hkl
Contains datablock Me2PA

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768112037457/ps5015sup7.pdf
Extra figures and tables

CCDC references: 906602; 906603; 906604; 906605; 906606

Computing details top

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.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
(Z2) 5,6-dimethylbenzfurazan 1-oxide, polymorph Z2 top
Crystal data top
C8H8N2O2Z = 2
Mr = 164.16F(000) = 172
Triclinic, P1Dx = 1.424 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 3.9506 (12) ÅCell parameters from 2363 reflections
b = 8.264 (3) Åθ = 2.5–27.4°
c = 12.045 (4) ŵ = 0.11 mm1
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
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
1713 independent reflections
Radiation source: fine-focus sealed tube1379 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
SADABS; Sheldrick, 2008; Blessing, 1995
h = 55
Tmin = 0.94, Tmax = 0.99k = 1010
4353 measured reflectionsl = 015
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H-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 reflectionsΔρmax = 0.26 e Å3
153 parametersΔρmin = 0.22 e Å3
32 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.036 (12)
Crystal data top
C8H8N2O2γ = 86.990 (4)°
Mr = 164.16V = 382.9 (2) Å3
Triclinic, P1Z = 2
a = 3.9506 (12) ÅMo Kα radiation
b = 8.264 (3) ŵ = 0.11 mm1
c = 12.045 (4) ÅT = 173 K
α = 78.842 (4)°0.50 × 0.13 × 0.06 mm
β = 83.180 (4)°
Data collection top
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 = 0.99Rint = 0.031
4353 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05632 restraints
wR(F2) = 0.156H-atom parameters constrained
S = 1.10Δρmax = 0.26 e Å3
1713 reflectionsΔρmin = 0.22 e Å3
153 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.1496 (4)0.70009 (19)0.91155 (13)0.0498 (5)0.893 (2)
O20.0065 (4)0.73775 (17)0.72944 (12)0.0408 (4)0.893 (2)
N10.1523 (4)0.6406 (2)0.82482 (14)0.0355 (4)0.893 (2)
N20.0245 (5)0.6514 (2)0.64120 (15)0.0379 (4)0.893 (2)
C10.2734 (5)0.5024 (2)0.79133 (16)0.0287 (4)0.893 (2)
C20.1939 (5)0.5115 (2)0.67857 (16)0.0293 (4)0.893 (2)
C30.2905 (8)0.3783 (3)0.62238 (18)0.0299 (4)0.893 (2)
H30.23870.38170.54690.036*0.893 (2)
C40.4600 (9)0.2444 (3)0.67855 (19)0.0285 (4)0.893 (2)
C50.5368 (6)0.2371 (2)0.79559 (19)0.0281 (4)0.893 (2)
C60.4453 (6)0.3642 (2)0.85114 (16)0.0298 (4)0.893 (2)
H60.49480.36020.92690.036*0.893 (2)
C70.566 (2)0.1021 (5)0.6203 (3)0.0382 (5)0.893 (2)
H7A0.49840.12620.54300.057*0.893 (2)
H7B0.45450.00220.66320.057*0.893 (2)
H7C0.81400.08480.61670.057*0.893 (2)
C80.7154 (6)0.0834 (3)0.8546 (2)0.0340 (6)0.893 (2)
H8A0.74860.09570.93180.051*0.893 (2)
H8B0.93740.06750.81170.051*0.893 (2)
H8C0.57560.01250.85850.051*0.893 (2)
O1A0.081 (3)0.7371 (12)0.6150 (8)0.048 (4)0.107 (2)
O2A0.056 (3)0.7230 (10)0.7976 (8)0.0408 (4)0.107 (2)
N1A0.058 (3)0.6545 (11)0.6949 (7)0.0379 (4)0.107 (2)
N2A0.222 (3)0.6131 (11)0.8764 (7)0.0355 (4)0.107 (2)
C1A0.218 (4)0.5076 (11)0.7154 (8)0.0293 (4)0.107 (2)
C2A0.306 (4)0.4820 (11)0.8283 (7)0.0287 (4)0.107 (2)
C3A0.482 (5)0.3345 (14)0.8721 (11)0.0298 (4)0.107 (2)
H3A0.55500.31750.94590.036*0.107 (2)
C4A0.545 (4)0.2165 (11)0.8061 (12)0.0281 (4)0.107 (2)
C5A0.466 (7)0.2488 (16)0.6878 (12)0.0285 (4)0.107 (2)
C6A0.305 (7)0.3924 (18)0.6430 (11)0.0299 (4)0.107 (2)
H6A0.25320.41420.56640.036*0.107 (2)
C7A0.667 (7)0.0470 (13)0.8583 (16)0.0340 (6)0.107 (2)
H7AA0.71310.04590.93660.051*0.107 (2)
H7AB0.87640.01670.81370.051*0.107 (2)
H7AC0.49100.03250.85870.051*0.107 (2)
C8A0.549 (18)0.115 (4)0.618 (2)0.0382 (5)0.107 (2)
H8AA0.43940.14340.54760.057*0.107 (2)
H8AB0.46380.00970.66210.057*0.107 (2)
H8AC0.79620.10530.59940.057*0.107 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0655 (10)0.0482 (9)0.0433 (9)0.0144 (7)0.0138 (7)0.0268 (7)
O20.0485 (8)0.0325 (7)0.0430 (9)0.0107 (6)0.0129 (7)0.0096 (6)
N10.0403 (9)0.0350 (9)0.0340 (10)0.0049 (7)0.0087 (7)0.0121 (8)
N20.0432 (10)0.0373 (9)0.0339 (10)0.0063 (8)0.0092 (8)0.0076 (8)
C10.0290 (9)0.0292 (9)0.0288 (11)0.0010 (7)0.0030 (8)0.0086 (8)
C20.0280 (8)0.0323 (9)0.0270 (10)0.0000 (7)0.0024 (8)0.0045 (7)
C30.0304 (9)0.0349 (10)0.0254 (10)0.0007 (7)0.0038 (8)0.0079 (7)
C40.0254 (8)0.0333 (9)0.0276 (9)0.0014 (6)0.0004 (7)0.0091 (7)
C50.0253 (8)0.0305 (9)0.0274 (9)0.0001 (7)0.0003 (6)0.0043 (7)
C60.0304 (10)0.0359 (11)0.0237 (10)0.0003 (8)0.0047 (7)0.0061 (8)
C70.0399 (14)0.0400 (12)0.0371 (10)0.0016 (9)0.0004 (7)0.0159 (9)
C80.0325 (12)0.0313 (10)0.0361 (10)0.0007 (9)0.0042 (8)0.0010 (9)
O1A0.051 (8)0.051 (8)0.038 (7)0.032 (6)0.026 (6)0.002 (6)
O2A0.0485 (8)0.0325 (7)0.0430 (9)0.0107 (6)0.0129 (7)0.0096 (6)
N1A0.0432 (10)0.0373 (9)0.0339 (10)0.0063 (8)0.0092 (8)0.0076 (8)
N2A0.0403 (9)0.0350 (9)0.0340 (10)0.0049 (7)0.0087 (7)0.0121 (8)
C1A0.0280 (8)0.0323 (9)0.0270 (10)0.0000 (7)0.0024 (8)0.0045 (7)
C2A0.0290 (9)0.0292 (9)0.0288 (11)0.0010 (7)0.0030 (8)0.0086 (8)
C3A0.0304 (10)0.0359 (11)0.0237 (10)0.0003 (8)0.0047 (7)0.0061 (8)
C4A0.0253 (8)0.0305 (9)0.0274 (9)0.0001 (7)0.0003 (6)0.0043 (7)
C5A0.0254 (8)0.0333 (9)0.0276 (9)0.0014 (6)0.0004 (7)0.0091 (7)
C6A0.0304 (9)0.0349 (10)0.0254 (10)0.0007 (7)0.0038 (8)0.0079 (7)
C7A0.0325 (12)0.0313 (10)0.0361 (10)0.0007 (9)0.0042 (8)0.0010 (9)
C8A0.0399 (14)0.0400 (12)0.0371 (10)0.0016 (9)0.0004 (7)0.0159 (9)
Geometric parameters (Å, º) top
O1—N11.236 (2)O1A—N1A1.236 (2)
O2—N21.381 (2)O2A—N2A1.381 (2)
O2—N11.456 (2)O2A—N1A1.456 (2)
N1—C11.331 (2)N1A—C1A1.331 (3)
N2—C21.333 (3)N2A—C2A1.333 (3)
C1—C61.414 (2)C1A—C6A1.414 (3)
C1—C21.417 (3)C1A—C2A1.418 (3)
C2—C31.414 (3)C2A—C3A1.414 (3)
C3—C41.367 (3)C3A—C4A1.368 (3)
C3—H30.9500C3A—H3A0.9500
C4—C51.466 (2)C4A—C5A1.467 (2)
C4—C71.500 (3)C4A—C7A1.500 (3)
C5—C61.363 (3)C5A—C6A1.363 (3)
C5—C81.514 (3)C5A—C8A1.514 (3)
C6—H60.9500C6A—H6A0.9500
C7—H7A0.9800C7A—H7AA0.9800
C7—H7B0.9800C7A—H7AB0.9800
C7—H7C0.9800C7A—H7AC0.9800
C8—H8A0.9800C8A—H8AA0.9800
C8—H8B0.9800C8A—H8AB0.9800
C8—H8C0.9800C8A—H8AC0.9800
N2—O2—N1109.06 (14)N2A—O2A—N1A109.05 (15)
O1—N1—C1136.04 (18)O1A—N1A—C1A136.0 (2)
O1—N1—O2117.78 (15)O1A—N1A—O2A117.77 (18)
C1—N1—O2106.18 (14)C1A—N1A—O2A106.17 (15)
C2—N2—O2105.57 (16)C2A—N2A—O2A105.52 (17)
N1—C1—C6129.90 (17)N1A—C1A—C6A129.92 (19)
N1—C1—C2107.42 (17)N1A—C1A—C2A107.40 (18)
C6—C1—C2122.67 (17)C6A—C1A—C2A122.65 (19)
N2—C2—C3128.95 (17)N2A—C2A—C3A128.9 (2)
N2—C2—C1111.78 (17)N2A—C2A—C1A111.73 (19)
C3—C2—C1119.26 (17)C3A—C2A—C1A119.22 (19)
C4—C3—C2118.83 (16)C4A—C3A—C2A118.75 (18)
C4—C3—H3120.6C4A—C3A—H3A120.6
C2—C3—H3120.6C2A—C3A—H3A120.6
C3—C4—C5120.97 (17)C3A—C4A—C5A120.85 (19)
C3—C4—C7119.66 (17)C3A—C4A—C7A119.6 (2)
C5—C4—C7119.37 (17)C5A—C4A—C7A119.3 (2)
C6—C5—C4121.02 (17)C6A—C5A—C4A120.98 (19)
C6—C5—C8120.44 (17)C6A—C5A—C8A120.4 (2)
C4—C5—C8118.53 (17)C4A—C5A—C8A118.5 (2)
C5—C6—C1117.25 (16)C5A—C6A—C1A117.24 (18)
C5—C6—H6121.4C5A—C6A—H6A121.4
C1—C6—H6121.4C1A—C6A—H6A121.4
C4—C7—H7A109.5C4A—C7A—H7AA109.5
C4—C7—H7B109.5C4A—C7A—H7AB109.5
H7A—C7—H7B109.5H7AA—C7A—H7AB109.5
C4—C7—H7C109.5C4A—C7A—H7AC109.5
H7A—C7—H7C109.5H7AA—C7A—H7AC109.5
H7B—C7—H7C109.5H7AB—C7A—H7AC109.5
C5—C8—H8A109.5C5A—C8A—H8AA109.5
C5—C8—H8B109.5C5A—C8A—H8AB109.5
H8A—C8—H8B109.5H8AA—C8A—H8AB109.5
C5—C8—H8C109.5C5A—C8A—H8AC109.5
H8A—C8—H8C109.5H8AA—C8A—H8AC109.5
H8B—C8—H8C109.5H8AB—C8A—H8AC109.5
N2—O2—N1—O1179.62 (16)N2A—O2A—N1A—O1A179.8 (14)
N2—O2—N1—C10.4 (2)N2A—O2A—N1A—C1A0.9 (16)
N1—O2—N2—C20.6 (2)N1A—O2A—N2A—C2A2.9 (16)
O1—N1—C1—C62.3 (4)O1A—N1A—C1A—C6A5 (4)
O2—N1—C1—C6178.7 (2)O2A—N1A—C1A—C6A177 (2)
O1—N1—C1—C2179.0 (2)O1A—N1A—C1A—C2A177.2 (19)
O2—N1—C1—C20.1 (2)O2A—N1A—C1A—C2A1.3 (17)
O2—N2—C2—C3179.3 (2)O2A—N2A—C2A—C3A179.4 (18)
O2—N2—C2—C10.6 (2)O2A—N2A—C2A—C1A3.8 (17)
N1—C1—C2—N20.3 (2)N1A—C1A—C2A—N2A3.4 (18)
C6—C1—C2—N2178.4 (2)C6A—C1A—C2A—N2A175 (2)
N1—C1—C2—C3179.2 (2)N1A—C1A—C2A—C3A179.4 (16)
C6—C1—C2—C30.4 (3)C6A—C1A—C2A—C3A1 (3)
N2—C2—C3—C4178.9 (3)N2A—C2A—C3A—C4A178.9 (16)
C1—C2—C3—C40.3 (4)C1A—C2A—C3A—C4A4 (2)
C2—C3—C4—C50.9 (4)C2A—C3A—C4A—C5A6.5 (18)
C2—C3—C4—C7179.8 (4)C2A—C3A—C4A—C7A168 (2)
C3—C4—C5—C60.8 (4)C3A—C4A—C5A—C6A5 (2)
C7—C4—C5—C6179.8 (4)C7A—C4A—C5A—C6A170 (3)
C3—C4—C5—C8178.1 (3)C3A—C4A—C5A—C8A179 (3)
C7—C4—C5—C81.2 (4)C7A—C4A—C5A—C8A7 (3)
C4—C5—C6—C10.1 (3)C4A—C5A—C6A—C1A0 (3)
C8—C5—C6—C1178.8 (2)C8A—C5A—C6A—C1A176 (4)
N1—C1—C6—C5179.0 (2)N1A—C1A—C6A—C5A179 (2)
C2—C1—C6—C50.5 (3)C2A—C1A—C6A—C5A3 (3)
(Z4) 5,6-benzfurazan 1-oxide, polymorph Z4 top
Crystal data top
C8H8N2O2Z = 4
Mr = 164.16F(000) = 344
Triclinic, P1Dx = 1.416 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.3643 (9) ÅCell parameters from 3327 reflections
b = 9.0332 (11) Åθ = 2.8–27.3°
c = 11.6675 (14) ŵ = 0.11 mm1
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
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
3498 independent reflections
Radiation source: fine-focus sealed tube2286 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
SADABS; Sheldrick, 2008; Blessing, 1995
h = 99
Tmin = 0.96, Tmax = 0.97k = 1111
8977 measured reflectionsl = 015
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-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 reflectionsΔρmax = 0.19 e Å3
304 parametersΔρmin = 0.15 e Å3
192 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.007 (2)
Crystal data top
C8H8N2O2γ = 87.027 (2)°
Mr = 164.16V = 769.99 (16) Å3
Triclinic, P1Z = 4
a = 7.3643 (9) ÅMo Kα radiation
b = 9.0332 (11) ŵ = 0.11 mm1
c = 11.6675 (14) ÅT = 173 K
α = 89.264 (2)°0.35 × 0.30 × 0.25 mm
β = 83.419 (2)°
Data collection top
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 = 0.97Rint = 0.024
8977 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.049192 restraints
wR(F2) = 0.140H-atom parameters constrained
S = 1.05Δρmax = 0.19 e Å3
3498 reflectionsΔρmin = 0.15 e Å3
304 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O110.8147 (2)0.79897 (19)0.00576 (14)0.0541 (5)0.5672 (12)
O120.6189 (2)0.81070 (16)0.17525 (13)0.0483 (5)0.5672 (12)
N110.7192 (3)0.7289 (2)0.08020 (16)0.0391 (5)0.5672 (12)
N120.5183 (3)0.7141 (2)0.24628 (17)0.0430 (5)0.5672 (12)
C110.6769 (7)0.5874 (3)0.0966 (3)0.0316 (6)0.5672 (12)
C120.5557 (7)0.5803 (3)0.1980 (3)0.0316 (6)0.5672 (12)
C130.4931 (12)0.4414 (4)0.2386 (5)0.0340 (6)0.5672 (12)
H130.40850.43480.30610.041*0.5672 (12)
C140.5574 (11)0.3164 (4)0.1781 (5)0.0301 (8)0.5672 (12)
C150.6857 (11)0.3272 (4)0.0734 (5)0.0290 (9)0.5672 (12)
C160.7410 (13)0.4605 (4)0.0320 (6)0.0336 (7)0.5672 (12)
H160.82000.46810.03790.040*0.5672 (12)
C170.4851 (19)0.1680 (5)0.2134 (9)0.0439 (6)0.5672 (12)
H17A0.39560.17960.28210.066*0.5672 (12)
H17B0.58650.10010.23100.066*0.5672 (12)
H17C0.42610.12770.15030.066*0.5672 (12)
C180.743 (2)0.1895 (5)0.0047 (10)0.0461 (12)0.5672 (12)
H18A0.83440.21360.06000.069*0.5672 (12)
H18B0.63650.15030.02510.069*0.5672 (12)
H18C0.79700.11480.05430.069*0.5672 (12)
O11A0.4893 (3)0.8068 (2)0.27788 (17)0.0566 (7)0.4328 (12)
O12A0.6861 (3)0.8172 (2)0.10931 (17)0.0483 (5)0.4328 (12)
N11A0.5751 (5)0.7360 (2)0.1967 (2)0.0430 (5)0.4328 (12)
N12A0.7688 (4)0.7194 (3)0.0270 (2)0.0391 (5)0.4328 (12)
C11A0.5949 (10)0.5936 (3)0.1654 (4)0.0316 (6)0.4328 (12)
C12A0.7139 (10)0.5854 (3)0.0628 (5)0.0316 (6)0.4328 (12)
C13A0.7539 (18)0.4470 (5)0.0074 (8)0.0336 (7)0.4328 (12)
H13A0.83710.43900.06110.040*0.4328 (12)
C14A0.6698 (15)0.3249 (5)0.0548 (7)0.0290 (9)0.4328 (12)
C15A0.5494 (16)0.3363 (4)0.1633 (8)0.0301 (8)0.4328 (12)
C16A0.5133 (17)0.4682 (5)0.2178 (7)0.0340 (6)0.4328 (12)
H16A0.43590.47570.28860.041*0.4328 (12)
C17A0.719 (3)0.1741 (6)0.0036 (14)0.0461 (12)0.4328 (12)
H17D0.79430.18460.07050.069*0.4328 (12)
H17E0.60660.12540.00830.069*0.4328 (12)
H17F0.78710.11410.05640.069*0.4328 (12)
C18A0.482 (3)0.1969 (6)0.2220 (11)0.0439 (6)0.4328 (12)
H18D0.41020.22210.29580.066*0.4328 (12)
H18E0.58680.13050.23580.066*0.4328 (12)
H18F0.40510.14750.17260.066*0.4328 (12)
O210.0409 (2)0.37167 (17)0.75642 (13)0.0532 (5)0.6307 (14)
O220.1562 (2)0.36192 (15)0.58742 (12)0.0460 (4)0.6307 (14)
N210.0502 (3)0.4431 (2)0.68069 (15)0.0378 (5)0.6307 (14)
N220.2478 (3)0.4607 (2)0.51346 (16)0.0429 (5)0.6307 (14)
C210.0812 (7)0.5863 (3)0.6608 (3)0.0306 (6)0.6307 (14)
C220.2011 (6)0.5949 (3)0.5590 (3)0.0316 (5)0.6307 (14)
C230.2554 (10)0.7352 (4)0.5161 (5)0.0349 (5)0.6307 (14)
H230.33960.74300.44840.042*0.6307 (14)
C240.1835 (11)0.8597 (3)0.5744 (5)0.0309 (7)0.6307 (14)
C250.0575 (12)0.8471 (4)0.6800 (5)0.0307 (8)0.6307 (14)
C260.0114 (13)0.7127 (4)0.7240 (6)0.0324 (5)0.6307 (14)
H260.06510.70410.79480.039*0.6307 (14)
C270.2451 (17)1.0103 (4)0.5360 (8)0.0436 (6)0.6307 (14)
H27A0.33581.00010.46780.065*0.6307 (14)
H27B0.30011.05650.59830.065*0.6307 (14)
H27C0.13971.07240.51670.065*0.6307 (14)
C280.011 (2)0.9852 (4)0.7455 (11)0.0438 (6)0.6307 (14)
H28A0.09930.95930.81090.066*0.6307 (14)
H28B0.06961.05460.69420.066*0.6307 (14)
H28C0.09271.03170.77390.066*0.6307 (14)
O21A0.2898 (4)0.3693 (3)0.4810 (2)0.0553 (9)0.3693 (14)
O22A0.0941 (4)0.3529 (2)0.6496 (2)0.0460 (4)0.3693 (14)
N21A0.1980 (6)0.4378 (3)0.5611 (3)0.0429 (5)0.3693 (14)
N22A0.0035 (5)0.4486 (3)0.7307 (3)0.0378 (5)0.3693 (14)
C21A0.1658 (12)0.5802 (3)0.5904 (5)0.0316 (5)0.3693 (14)
C22A0.0466 (12)0.5848 (4)0.6930 (6)0.0306 (6)0.3693 (14)
C23A0.009 (2)0.7231 (5)0.7451 (11)0.0324 (5)0.3693 (14)
H23A0.09420.72870.81250.039*0.3693 (14)
C24A0.064 (2)0.8489 (5)0.6960 (9)0.0307 (8)0.3693 (14)
C25A0.1889 (19)0.8405 (4)0.5890 (9)0.0309 (7)0.3693 (14)
C26A0.2345 (19)0.7090 (5)0.5356 (8)0.0349 (5)0.3693 (14)
H26A0.30990.70400.46390.042*0.3693 (14)
C27A0.001 (4)0.9988 (6)0.7434 (19)0.0438 (6)0.3693 (14)
H27D0.07090.98690.81920.066*0.3693 (14)
H27E0.07831.04940.69080.066*0.3693 (14)
H27F0.10531.05790.75120.066*0.3693 (14)
C28A0.249 (3)0.9819 (5)0.5302 (13)0.0436 (6)0.3693 (14)
H28D0.31670.95890.45470.065*0.3693 (14)
H28E0.32841.03190.57770.065*0.3693 (14)
H28F0.14141.04700.51990.065*0.3693 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O110.0643 (12)0.0414 (12)0.0560 (11)0.0170 (9)0.0009 (9)0.0123 (9)
O120.0594 (13)0.0357 (8)0.0498 (12)0.0037 (8)0.0054 (9)0.0053 (9)
N110.0439 (14)0.0415 (10)0.0320 (15)0.0057 (10)0.0036 (11)0.0046 (13)
N120.0473 (16)0.0411 (11)0.0398 (17)0.0010 (10)0.0010 (11)0.0066 (12)
C110.029 (2)0.0335 (9)0.032 (3)0.0026 (8)0.0034 (14)0.0020 (10)
C120.034 (2)0.0318 (10)0.029 (2)0.0002 (9)0.0029 (13)0.0019 (11)
C130.0373 (19)0.0417 (15)0.022 (2)0.0021 (15)0.0011 (12)0.0040 (15)
C140.0319 (9)0.0315 (11)0.0282 (16)0.0038 (12)0.0128 (12)0.0095 (11)
C150.0301 (13)0.0369 (8)0.0227 (18)0.0014 (6)0.0153 (15)0.0039 (7)
C160.0346 (13)0.0444 (11)0.021 (3)0.0025 (11)0.0018 (16)0.0013 (9)
C170.0433 (9)0.0352 (16)0.0542 (15)0.005 (3)0.0088 (11)0.0070 (17)
C180.047 (3)0.0397 (12)0.0521 (9)0.0028 (13)0.0082 (17)0.0139 (13)
O11A0.0798 (18)0.0387 (15)0.0487 (15)0.0064 (13)0.0016 (13)0.0160 (12)
O12A0.0594 (13)0.0357 (8)0.0498 (12)0.0037 (8)0.0054 (9)0.0053 (9)
N11A0.0473 (16)0.0411 (11)0.0398 (17)0.0010 (10)0.0010 (11)0.0066 (12)
N12A0.0439 (14)0.0415 (10)0.0320 (15)0.0057 (10)0.0036 (11)0.0046 (13)
C11A0.034 (2)0.0318 (10)0.029 (2)0.0002 (9)0.0029 (13)0.0019 (11)
C12A0.029 (2)0.0335 (9)0.032 (3)0.0026 (8)0.0034 (14)0.0020 (10)
C13A0.0346 (13)0.0444 (11)0.021 (3)0.0025 (11)0.0018 (16)0.0013 (9)
C14A0.0301 (13)0.0369 (8)0.0227 (18)0.0014 (6)0.0153 (15)0.0039 (7)
C15A0.0319 (9)0.0315 (11)0.0282 (16)0.0038 (12)0.0128 (12)0.0095 (11)
C16A0.0373 (19)0.0417 (15)0.022 (2)0.0021 (15)0.0011 (12)0.0040 (15)
C17A0.047 (3)0.0397 (12)0.0521 (9)0.0028 (13)0.0082 (17)0.0139 (13)
C18A0.0433 (9)0.0352 (16)0.0542 (15)0.005 (3)0.0088 (11)0.0070 (17)
O210.0670 (11)0.0369 (10)0.0545 (10)0.0137 (8)0.0024 (8)0.0118 (8)
O220.0565 (12)0.0331 (7)0.0482 (12)0.0032 (7)0.0062 (9)0.0073 (9)
N210.0438 (13)0.0352 (9)0.0345 (14)0.0012 (9)0.0056 (10)0.0008 (12)
N220.0472 (15)0.0391 (11)0.0410 (16)0.0036 (9)0.0014 (11)0.0076 (11)
C210.031 (2)0.0303 (8)0.030 (2)0.0000 (7)0.0038 (12)0.0007 (9)
C220.033 (2)0.0321 (9)0.029 (2)0.0017 (8)0.0033 (11)0.0021 (9)
C230.0352 (18)0.0410 (13)0.0272 (19)0.0003 (14)0.0006 (11)0.0011 (12)
C240.0330 (8)0.0314 (10)0.0290 (15)0.0035 (11)0.0095 (12)0.0066 (10)
C250.0322 (9)0.0327 (7)0.0288 (17)0.0010 (5)0.0107 (14)0.0042 (6)
C260.031 (2)0.0384 (9)0.027 (2)0.0004 (10)0.0000 (12)0.0023 (8)
C270.0439 (10)0.0337 (14)0.0538 (11)0.004 (2)0.0073 (9)0.0058 (16)
C280.0439 (17)0.0363 (10)0.0512 (10)0.0012 (13)0.0052 (9)0.0114 (13)
O21A0.073 (2)0.0406 (18)0.0487 (17)0.0097 (15)0.0035 (15)0.0176 (14)
O22A0.0565 (12)0.0331 (7)0.0482 (12)0.0032 (7)0.0062 (9)0.0073 (9)
N21A0.0472 (15)0.0391 (11)0.0410 (16)0.0036 (9)0.0014 (11)0.0076 (11)
N22A0.0438 (13)0.0352 (9)0.0345 (14)0.0012 (9)0.0056 (10)0.0008 (12)
C21A0.033 (2)0.0321 (9)0.029 (2)0.0017 (8)0.0033 (11)0.0021 (9)
C22A0.031 (2)0.0303 (8)0.030 (2)0.0000 (7)0.0038 (12)0.0007 (9)
C23A0.031 (2)0.0384 (9)0.027 (2)0.0004 (10)0.0000 (12)0.0023 (8)
C24A0.0322 (9)0.0327 (7)0.0288 (17)0.0010 (5)0.0107 (14)0.0042 (6)
C25A0.0330 (8)0.0314 (10)0.0290 (15)0.0035 (11)0.0095 (12)0.0066 (10)
C26A0.0352 (18)0.0410 (13)0.0272 (19)0.0003 (14)0.0006 (11)0.0011 (12)
C27A0.0439 (17)0.0363 (10)0.0512 (10)0.0012 (13)0.0052 (9)0.0114 (13)
C28A0.0439 (10)0.0337 (14)0.0538 (11)0.004 (2)0.0073 (9)0.0058 (16)
Geometric parameters (Å, º) top
O11—N111.2416 (18)O21—N211.2415 (18)
O12—N121.3801 (18)O22—N221.3802 (18)
O12—N111.4484 (17)O22—N211.4482 (17)
N11—C111.338 (3)N21—C211.338 (3)
N12—C121.342 (3)N22—C221.342 (3)
C11—C121.4008 (19)C21—C221.4006 (19)
C11—C161.409 (3)C21—C261.409 (3)
C12—C131.417 (3)C22—C231.417 (3)
C13—C141.373 (4)C23—C241.373 (4)
C13—H130.9500C23—H230.9500
C14—C151.4615 (15)C24—C251.4616 (15)
C14—C171.503 (5)C24—C271.503 (5)
C15—C161.357 (4)C25—C261.356 (4)
C15—C181.505 (4)C25—C281.505 (4)
C16—H160.9500C26—H260.9500
C17—H17A0.9800C27—H27A0.9800
C17—H17B0.9800C27—H27B0.9800
C17—H17C0.9800C27—H27C0.9800
C18—H18A0.9800C28—H28A0.9800
C18—H18B0.9800C28—H28B0.9800
C18—H18C0.9800C28—H28C0.9800
O11A—N11A1.2415 (19)O21A—N21A1.2415 (19)
O12A—N12A1.3801 (18)O22A—N22A1.3801 (18)
O12A—N11A1.4485 (18)O22A—N21A1.4486 (18)
N11A—C11A1.338 (3)N21A—C21A1.337 (3)
N12A—C12A1.342 (3)N22A—C22A1.342 (3)
C11A—C12A1.4008 (19)C21A—C22A1.4008 (19)
C11A—C16A1.409 (3)C21A—C26A1.409 (3)
C12A—C13A1.417 (3)C22A—C23A1.417 (3)
C13A—C14A1.373 (4)C23A—C24A1.373 (4)
C13A—H13A0.9500C23A—H23A0.9500
C14A—C15A1.4620 (15)C24A—C25A1.4621 (16)
C14A—C17A1.504 (5)C24A—C27A1.504 (5)
C15A—C16A1.356 (4)C25A—C26A1.357 (4)
C15A—C18A1.505 (4)C25A—C28A1.505 (4)
C16A—H16A0.9500C26A—H26A0.9500
C17A—H17D0.9800C27A—H27D0.9800
C17A—H17E0.9800C27A—H27E0.9800
C17A—H17F0.9800C27A—H27F0.9800
C18A—H18D0.9800C28A—H28D0.9800
C18A—H18E0.9800C28A—H28E0.9800
C18A—H18F0.9800C28A—H28F0.9800
N12—O12—N11109.19 (12)N22—O22—N21109.16 (11)
O11—N11—C11135.69 (17)O21—N21—C21135.65 (17)
O11—N11—O12118.15 (14)O21—N21—O22118.19 (13)
C11—N11—O12106.13 (14)C21—N21—O22106.15 (14)
C12—N12—O12105.19 (14)C22—N22—O22105.21 (14)
N11—C11—C12107.5 (2)N21—C21—C22107.5 (2)
N11—C11—C16129.9 (2)N21—C21—C26129.9 (2)
C12—C11—C16122.6 (3)C22—C21—C26122.6 (3)
N12—C12—C11112.0 (2)N22—C22—C21112.0 (2)
N12—C12—C13128.35 (19)N22—C22—C23128.38 (19)
C11—C12—C13119.7 (3)C21—C22—C23119.6 (3)
C14—C13—C12118.5 (2)C24—C23—C22118.5 (2)
C14—C13—H13120.8C24—C23—H23120.8
C12—C13—H13120.8C22—C23—H23120.8
C13—C14—C15120.6 (3)C23—C24—C25120.6 (3)
C13—C14—C17120.3 (3)C23—C24—C27120.3 (3)
C15—C14—C17119.0 (3)C25—C24—C27119.0 (3)
C16—C15—C14121.1 (3)C26—C25—C24121.1 (3)
C16—C15—C18119.4 (3)C26—C25—C28119.5 (3)
C14—C15—C18119.2 (3)C24—C25—C28119.2 (3)
C15—C16—C11117.6 (2)C25—C26—C21117.5 (2)
C15—C16—H16121.2C25—C26—H26121.2
C11—C16—H16121.2C21—C26—H26121.2
C14—C17—H17A109.5C24—C27—H27A109.5
C14—C17—H17B109.5C24—C27—H27B109.5
H17A—C17—H17B109.5H27A—C27—H27B109.5
C14—C17—H17C109.5C24—C27—H27C109.5
H17A—C17—H17C109.5H27A—C27—H27C109.5
H17B—C17—H17C109.5H27B—C27—H27C109.5
C15—C18—H18A109.5C25—C28—H28A109.5
C15—C18—H18B109.5C25—C28—H28B109.5
H18A—C18—H18B109.5H28A—C28—H28B109.5
C15—C18—H18C109.5C25—C28—H28C109.5
H18A—C18—H18C109.5H28A—C28—H28C109.5
H18B—C18—H18C109.5H28B—C28—H28C109.5
N12A—O12A—N11A109.18 (12)N22A—O22A—N21A109.18 (12)
O11A—N11A—C11A135.74 (18)O21A—N21A—C21A135.78 (18)
O11A—N11A—O12A118.12 (14)O21A—N21A—O22A118.08 (14)
C11A—N11A—O12A106.14 (14)C21A—N21A—O22A106.13 (14)
C12A—N12A—O12A105.19 (14)C22A—N22A—O22A105.18 (14)
N11A—C11A—C12A107.5 (2)N21A—C21A—C22A107.5 (2)
N11A—C11A—C16A129.9 (2)N21A—C21A—C26A129.9 (2)
C12A—C11A—C16A122.6 (3)C22A—C21A—C26A122.5 (3)
N12A—C12A—C11A112.0 (2)N22A—C22A—C21A112.0 (2)
N12A—C12A—C13A128.3 (2)N22A—C22A—C23A128.4 (2)
C11A—C12A—C13A119.6 (3)C21A—C22A—C23A119.6 (3)
C14A—C13A—C12A118.5 (2)C24A—C23A—C22A118.5 (2)
C14A—C13A—H13A120.8C24A—C23A—H23A120.8
C12A—C13A—H13A120.8C22A—C23A—H23A120.8
C13A—C14A—C15A120.5 (3)C23A—C24A—C25A120.5 (3)
C13A—C14A—C17A120.1 (3)C23A—C24A—C27A120.2 (3)
C15A—C14A—C17A118.9 (3)C25A—C24A—C27A118.9 (3)
C16A—C15A—C14A121.1 (3)C26A—C25A—C24A121.1 (3)
C16A—C15A—C18A119.4 (3)C26A—C25A—C28A119.4 (3)
C14A—C15A—C18A119.1 (3)C24A—C25A—C28A119.1 (3)
C15A—C16A—C11A117.6 (2)C25A—C26A—C21A117.6 (2)
C15A—C16A—H16A121.2C25A—C26A—H26A121.2
C11A—C16A—H16A121.2C21A—C26A—H26A121.2
C14A—C17A—H17D109.5C24A—C27A—H27D109.5
C14A—C17A—H17E109.5C24A—C27A—H27E109.5
H17D—C17A—H17E109.5H27D—C27A—H27E109.5
C14A—C17A—H17F109.5C24A—C27A—H27F109.5
H17D—C17A—H17F109.5H27D—C27A—H27F109.5
H17E—C17A—H17F109.5H27E—C27A—H27F109.5
C15A—C18A—H18D109.5C25A—C28A—H28D109.5
C15A—C18A—H18E109.5C25A—C28A—H28E109.5
H18D—C18A—H18E109.5H28D—C28A—H28E109.5
C15A—C18A—H18F109.5C25A—C28A—H28F109.5
H18D—C18A—H18F109.5H28D—C28A—H28F109.5
H18E—C18A—H18F109.5H28E—C28A—H28F109.5
N12—O12—N11—O11178.5 (2)N22—O22—N21—O21179.6 (2)
N12—O12—N11—C110.1 (4)N22—O22—N21—C210.3 (4)
N11—O12—N12—C120.4 (4)N21—O22—N22—C220.2 (3)
O11—N11—C11—C12178.4 (4)O21—N21—C21—C22179.3 (4)
O12—N11—C11—C120.2 (5)O22—N21—C21—C220.2 (5)
O11—N11—C11—C164.3 (10)O21—N21—C21—C261.5 (10)
O12—N11—C11—C16177.6 (7)O22—N21—C21—C26179.4 (7)
O12—N12—C12—C110.6 (6)O22—N22—C22—C210.1 (5)
O12—N12—C12—C13177.5 (8)O22—N22—C22—C23179.0 (6)
N11—C11—C12—N120.5 (7)N21—C21—C22—N220.1 (6)
C16—C11—C12—N12178.1 (7)C26—C21—C22—N22179.4 (7)
N11—C11—C12—C13177.8 (7)N21—C21—C22—C23178.9 (6)
C16—C11—C12—C130.2 (10)C26—C21—C22—C230.3 (9)
N12—C12—C13—C14176.4 (7)N22—C22—C23—C24176.9 (6)
C11—C12—C13—C141.6 (12)C21—C22—C23—C242.0 (10)
C12—C13—C14—C150.8 (12)C22—C23—C24—C251.5 (10)
C12—C13—C14—C17175.9 (9)C22—C23—C24—C27176.6 (8)
C13—C14—C15—C161.6 (10)C23—C24—C25—C261.4 (9)
C17—C14—C15—C16173.6 (10)C27—C24—C25—C26173.8 (9)
C13—C14—C15—C18175.8 (11)C23—C24—C25—C28176.6 (10)
C17—C14—C15—C180.6 (9)C27—C24—C25—C281.5 (9)
C14—C15—C16—C112.9 (11)C24—C25—C26—C213.5 (11)
C18—C15—C16—C11177.2 (10)C28—C25—C26—C21178.8 (9)
N11—C11—C16—C15174.9 (7)N21—C21—C26—C25176.0 (7)
C12—C11—C16—C152.1 (12)C22—C21—C26—C253.1 (11)
N12A—O12A—N11A—O11A179.7 (3)N22A—O22A—N21A—O21A179.5 (4)
N12A—O12A—N11A—C11A0.4 (6)N22A—O22A—N21A—C21A0.6 (7)
N11A—O12A—N12A—C12A0.9 (6)N21A—O22A—N22A—C22A1.0 (7)
O11A—N11A—C11A—C12A179.7 (6)O21A—N21A—C21A—C22A179.8 (8)
O12A—N11A—C11A—C12A0.2 (8)O22A—N21A—C21A—C22A0.0 (10)
O11A—N11A—C11A—C16A2.1 (16)O21A—N21A—C21A—C26A1.3 (18)
O12A—N11A—C11A—C16A178.0 (11)O22A—N21A—C21A—C26A178.8 (12)
O12A—N12A—C12A—C11A1.0 (8)O22A—N22A—C22A—C21A1.1 (10)
O12A—N12A—C12A—C13A177.4 (10)O22A—N22A—C22A—C23A179.1 (13)
N11A—C11A—C12A—N12A0.8 (10)N21A—C21A—C22A—N22A0.7 (12)
C16A—C11A—C12A—N12A177.6 (10)C26A—C21A—C22A—N22A178.3 (11)
N11A—C11A—C12A—C13A177.5 (9)N21A—C21A—C22A—C23A178.9 (12)
C16A—C11A—C12A—C13A0.8 (14)C26A—C21A—C22A—C23A0.0 (18)
N12A—C12A—C13A—C14A174.3 (10)N22A—C22A—C23A—C24A174.6 (13)
C11A—C12A—C13A—C14A1.8 (16)C21A—C22A—C23A—C24A3 (2)
C12A—C13A—C14A—C15A3.2 (16)C22A—C23A—C24A—C25A3 (2)
C12A—C13A—C14A—C17A175.5 (13)C22A—C23A—C24A—C27A175.5 (17)
C13A—C14A—C15A—C16A2.1 (13)C23A—C24A—C25A—C26A0.3 (16)
C17A—C14A—C15A—C16A174.5 (15)C27A—C24A—C25A—C26A172.2 (18)
C13A—C14A—C15A—C18A170.9 (14)C23A—C24A—C25A—C28A172.9 (17)
C17A—C14A—C15A—C18A1.5 (13)C27A—C24A—C25A—C28A0.4 (15)
C14A—C15A—C16A—C11A0.5 (16)C24A—C25A—C26A—C21A3.5 (18)
C18A—C15A—C16A—C11A173.5 (13)C28A—C25A—C26A—C21A176.1 (15)
N11A—C11A—C16A—C15A176.0 (10)N21A—C21A—C26A—C25A175.3 (12)
C12A—C11A—C16A—C15A2.0 (17)C22A—C21A—C26A—C25A3.4 (19)
(Z6) 5,6-benzfurazan 1-oxide, polymorph Z6 top
Crystal data top
C8H8N2O2Z = 6
Mr = 164.16F(000) = 516
Triclinic, P1Dx = 1.417 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.0070 (11) ÅCell parameters from 2306 reflections
b = 11.1331 (13) Åθ = 2.3–27.2°
c = 12.9526 (15) ŵ = 0.11 mm1
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
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
5157 independent reflections
Radiation source: fine-focus sealed tube3457 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
SADABS: Sheldrick, 2008; Blessing, 1995
h = 1111
Tmin = 0.96, Tmax = 0.98k = 1414
13249 measured reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168H-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 parametersΔρmax = 0.40 e Å3
480 restraintsΔρmin = 0.23 e Å3
Crystal data top
C8H8N2O2γ = 79.862 (2)°
Mr = 164.16V = 1154.6 (2) Å3
Triclinic, P1Z = 6
a = 9.0070 (11) ÅMo Kα radiation
b = 11.1331 (13) ŵ = 0.11 mm1
c = 12.9526 (15) ÅT = 173 K
α = 65.173 (2)°0.35 × 0.25 × 0.20 mm
β = 80.629 (2)°
Data collection top
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 = 0.98Rint = 0.020
13249 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.052480 restraints
wR(F2) = 0.168H-atom parameters constrained
S = 1.03Δρmax = 0.40 e Å3
5157 reflectionsΔρmin = 0.23 e Å3
454 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O110.29681 (13)0.36876 (12)0.09403 (9)0.0475 (4)0.7656 (15)
O120.28001 (11)0.20357 (11)0.27648 (9)0.0399 (3)0.7656 (15)
N110.36324 (14)0.29627 (13)0.17970 (11)0.0342 (3)0.7656 (15)
N120.37472 (15)0.13351 (14)0.36181 (11)0.0381 (4)0.7656 (15)
C110.50350 (19)0.2803 (2)0.20875 (15)0.0291 (4)0.7656 (15)
C120.50815 (18)0.1806 (2)0.31977 (14)0.0299 (4)0.7656 (15)
C130.6449 (2)0.1425 (4)0.3723 (2)0.0326 (4)0.7656 (15)
H130.65000.07610.44800.039*0.7656 (15)
C140.7699 (2)0.2038 (4)0.3114 (3)0.0300 (4)0.7656 (15)
C150.7615 (3)0.3079 (5)0.1958 (3)0.0305 (3)0.7656 (15)
C160.6303 (3)0.3459 (4)0.1451 (3)0.0312 (4)0.7656 (15)
H160.62420.41360.07010.037*0.7656 (15)
C170.9165 (3)0.1668 (5)0.3641 (3)0.0394 (4)0.7656 (15)
H17A0.90400.09710.44150.059*0.7656 (15)
H17B0.94600.24550.36780.059*0.7656 (15)
H17C0.99550.13380.31750.059*0.7656 (15)
C180.9017 (3)0.3718 (5)0.1310 (3)0.0405 (7)0.7656 (15)
H18A0.87810.43820.05520.061*0.7656 (15)
H18B0.98160.30330.12280.061*0.7656 (15)
H18C0.93660.41530.17300.061*0.7656 (15)
O11A0.2817 (4)0.1009 (4)0.3965 (3)0.0479 (12)0.2344 (15)
O12A0.2736 (3)0.2663 (4)0.2144 (3)0.0399 (3)0.2344 (15)
N11A0.3524 (3)0.1810 (5)0.3130 (3)0.0381 (4)0.2344 (15)
N12A0.3724 (4)0.3474 (4)0.1323 (3)0.0342 (3)0.2344 (15)
C11A0.4947 (4)0.2116 (8)0.2880 (5)0.0299 (4)0.2344 (15)
C12A0.5049 (5)0.3121 (8)0.1773 (5)0.0291 (4)0.2344 (15)
C13A0.6430 (8)0.3676 (14)0.1302 (9)0.0312 (4)0.2344 (15)
H13A0.65090.43850.05660.037*0.2344 (15)
C14A0.7650 (8)0.3163 (15)0.1935 (10)0.0305 (3)0.2344 (15)
C15A0.7507 (6)0.2120 (13)0.3092 (9)0.0300 (4)0.2344 (15)
C16A0.6187 (7)0.1577 (13)0.3548 (7)0.0326 (4)0.2344 (15)
H16A0.61030.08670.42820.039*0.2344 (15)
C17A0.9118 (10)0.3749 (19)0.1481 (10)0.0405 (7)0.2344 (15)
H17D0.90240.44610.07170.061*0.2344 (15)
H17E0.99280.30530.14370.061*0.2344 (15)
H17F0.93630.41150.19930.061*0.2344 (15)
C18A0.8889 (9)0.1544 (19)0.3742 (11)0.0394 (4)0.2344 (15)
H18D0.86240.08270.44800.059*0.2344 (15)
H18E0.92560.22450.38690.059*0.2344 (15)
H18F0.96860.11870.32980.059*0.2344 (15)
O210.8196 (2)0.47227 (18)0.40535 (13)0.0513 (6)0.5019 (11)
O220.83630 (17)0.63697 (18)0.22268 (13)0.0448 (4)0.5019 (11)
N210.7532 (2)0.5444 (2)0.31958 (15)0.0380 (5)0.5019 (11)
N220.7425 (2)0.7046 (2)0.13634 (15)0.0384 (5)0.5019 (11)
C210.6130 (3)0.5600 (5)0.2905 (3)0.0288 (6)0.5019 (11)
C220.6089 (3)0.6580 (5)0.1788 (3)0.0287 (5)0.5019 (11)
C230.4727 (5)0.6945 (10)0.1257 (5)0.0319 (5)0.5019 (11)
H230.46870.75790.04890.038*0.5019 (11)
C240.3465 (5)0.6360 (11)0.1880 (6)0.0290 (8)0.5019 (11)
C250.3531 (4)0.5368 (9)0.3056 (5)0.0276 (10)0.5019 (11)
C260.4850 (4)0.4974 (9)0.3557 (5)0.0311 (9)0.5019 (11)
H260.49080.43070.43110.037*0.5019 (11)
C270.2017 (7)0.6684 (15)0.1337 (7)0.0404 (5)0.5019 (11)
H27A0.21440.73710.05580.061*0.5019 (11)
H27B0.12010.70130.17870.061*0.5019 (11)
H27C0.17590.58790.13090.061*0.5019 (11)
C280.2148 (7)0.4686 (16)0.3689 (8)0.0427 (12)0.5019 (11)
H28A0.23770.40440.44560.064*0.5019 (11)
H28B0.18590.42190.32710.064*0.5019 (11)
H28C0.13100.53540.37490.064*0.5019 (11)
O21A0.83450 (19)0.73783 (18)0.10587 (14)0.0529 (6)0.4981 (11)
O22A0.84203 (18)0.57317 (18)0.28831 (13)0.0448 (4)0.4981 (11)
N21A0.7639 (2)0.6573 (2)0.18902 (16)0.0384 (5)0.4981 (11)
N22A0.7429 (2)0.4925 (2)0.37047 (15)0.0380 (5)0.4981 (11)
C21A0.6224 (3)0.6248 (5)0.2130 (3)0.0287 (5)0.4981 (11)
C22A0.6120 (3)0.5245 (5)0.3238 (3)0.0288 (6)0.4981 (11)
C23A0.4741 (5)0.4686 (9)0.3705 (5)0.0311 (9)0.4981 (11)
H23A0.46480.40040.44540.037*0.4981 (11)
C24A0.3543 (5)0.5154 (9)0.3050 (5)0.0276 (10)0.4981 (11)
C25A0.3673 (5)0.6225 (11)0.1907 (6)0.0290 (8)0.4981 (11)
C26A0.4991 (5)0.6772 (10)0.1454 (5)0.0319 (5)0.4981 (11)
H26A0.50790.74760.07150.038*0.4981 (11)
C27A0.2033 (7)0.4658 (16)0.3546 (8)0.0427 (12)0.4981 (11)
H27D0.21230.39520.43140.064*0.4981 (11)
H27E0.17020.43030.30570.064*0.4981 (11)
H27F0.12890.53950.35930.064*0.4981 (11)
C28A0.2297 (7)0.6787 (15)0.1250 (8)0.0404 (5)0.4981 (11)
H28D0.25690.74860.05030.061*0.4981 (11)
H28E0.15000.71660.16790.061*0.4981 (11)
H28F0.19260.60740.11440.061*0.4981 (11)
O310.59509 (17)0.78582 (16)0.39978 (12)0.0485 (5)0.5661 (12)
O320.60990 (15)0.94967 (16)0.21663 (12)0.0426 (4)0.5661 (12)
N310.52650 (18)0.86047 (19)0.31575 (14)0.0345 (4)0.5661 (12)
N320.5128 (2)1.0219 (2)0.13329 (14)0.0386 (5)0.5661 (12)
C310.3837 (3)0.8808 (5)0.2902 (3)0.0276 (5)0.5661 (12)
C320.3777 (2)0.9798 (5)0.1790 (3)0.0278 (5)0.5661 (12)
C330.2378 (4)1.0232 (9)0.1302 (4)0.0325 (5)0.5661 (12)
H330.23211.08770.05400.039*0.5661 (12)
C340.1107 (3)0.9697 (8)0.1959 (5)0.0279 (9)0.5661 (12)
C350.1202 (3)0.8674 (8)0.3122 (5)0.0268 (9)0.5661 (12)
C360.2549 (4)0.8222 (7)0.3583 (4)0.0289 (7)0.5661 (12)
H360.26220.75410.43300.035*0.5661 (12)
C370.0376 (5)1.0069 (13)0.1453 (7)0.0399 (5)0.5661 (12)
H37A0.02641.07660.06780.060*0.5661 (12)
H37B0.11501.03990.19270.060*0.5661 (12)
H37C0.06810.92830.14220.060*0.5661 (12)
C380.0191 (6)0.8023 (17)0.3778 (9)0.0405 (6)0.5661 (12)
H38A0.00540.73630.45360.061*0.5661 (12)
H38B0.05370.75810.33620.061*0.5661 (12)
H38C0.09960.87030.38620.061*0.5661 (12)
O31A0.6029 (2)1.0540 (2)0.09597 (15)0.0518 (6)0.4339 (12)
O32A0.6162 (2)0.8887 (2)0.27771 (15)0.0426 (4)0.4339 (12)
N31A0.5335 (2)0.9758 (3)0.18167 (19)0.0386 (5)0.4339 (12)
N32A0.5181 (3)0.8106 (3)0.36325 (18)0.0345 (4)0.4339 (12)
C31A0.3903 (3)0.9475 (6)0.2107 (4)0.0278 (5)0.4339 (12)
C32A0.3830 (3)0.8480 (7)0.3220 (4)0.0276 (5)0.4339 (12)
C33A0.2441 (5)0.7959 (11)0.3736 (6)0.0289 (7)0.4339 (12)
H33A0.23720.72700.44830.035*0.4339 (12)
C34A0.1195 (4)0.8472 (10)0.3131 (6)0.0268 (9)0.4339 (12)
C35A0.1302 (4)0.9518 (11)0.1973 (6)0.0279 (9)0.4339 (12)
C36A0.2631 (5)1.0028 (12)0.1473 (6)0.0325 (5)0.4339 (12)
H36A0.27011.07250.07310.039*0.4339 (12)
C37A0.0331 (7)0.805 (2)0.3693 (11)0.0405 (6)0.4339 (12)
H37D0.02210.73490.44590.061*0.4339 (12)
H37E0.07670.77210.32340.061*0.4339 (12)
H37F0.10010.88220.37550.061*0.4339 (12)
C38A0.0119 (6)1.0138 (18)0.1376 (10)0.0399 (5)0.4339 (12)
H38D0.01371.08170.06130.060*0.4339 (12)
H38E0.08351.05520.18220.060*0.4339 (12)
H38F0.05830.94470.13040.060*0.4339 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O110.0360 (7)0.0527 (8)0.0459 (7)0.0007 (6)0.0167 (6)0.0099 (6)
O120.0297 (6)0.0394 (8)0.0461 (9)0.0095 (6)0.0002 (6)0.0121 (6)
N110.0317 (7)0.0317 (9)0.0357 (9)0.0040 (7)0.0028 (7)0.0102 (7)
N120.0355 (8)0.0348 (10)0.0366 (10)0.0084 (7)0.0016 (7)0.0075 (7)
C110.0292 (7)0.0280 (13)0.0290 (12)0.0015 (6)0.0029 (7)0.0112 (8)
C120.0315 (8)0.0259 (12)0.0298 (11)0.0043 (7)0.0001 (6)0.0094 (8)
C130.0349 (10)0.0294 (11)0.0279 (10)0.0016 (10)0.0027 (6)0.0071 (7)
C140.0281 (8)0.0304 (8)0.0310 (6)0.0019 (8)0.0027 (6)0.0143 (5)
C150.0300 (6)0.0300 (9)0.0315 (6)0.0058 (5)0.0019 (5)0.0133 (6)
C160.0345 (8)0.0263 (15)0.0278 (10)0.0048 (6)0.0009 (7)0.0064 (6)
C170.0308 (12)0.0476 (13)0.0399 (10)0.0011 (11)0.0067 (11)0.0180 (8)
C180.0347 (8)0.0487 (8)0.0395 (13)0.0157 (7)0.0024 (7)0.0170 (11)
O11A0.036 (2)0.042 (2)0.051 (3)0.0165 (18)0.0069 (19)0.0040 (19)
O12A0.0297 (6)0.0394 (8)0.0461 (9)0.0095 (6)0.0002 (6)0.0121 (6)
N11A0.0355 (8)0.0348 (10)0.0366 (10)0.0084 (7)0.0016 (7)0.0075 (7)
N12A0.0317 (7)0.0317 (9)0.0357 (9)0.0040 (7)0.0028 (7)0.0102 (7)
C11A0.0315 (8)0.0259 (12)0.0298 (11)0.0043 (7)0.0001 (6)0.0094 (8)
C12A0.0292 (7)0.0280 (13)0.0290 (12)0.0015 (6)0.0029 (7)0.0112 (8)
C13A0.0345 (8)0.0263 (15)0.0278 (10)0.0048 (6)0.0009 (7)0.0064 (6)
C14A0.0300 (6)0.0300 (9)0.0315 (6)0.0058 (5)0.0019 (5)0.0133 (6)
C15A0.0281 (8)0.0304 (8)0.0310 (6)0.0019 (8)0.0027 (6)0.0143 (5)
C16A0.0349 (10)0.0294 (11)0.0279 (10)0.0016 (10)0.0027 (6)0.0071 (7)
C17A0.0347 (8)0.0487 (8)0.0395 (13)0.0157 (7)0.0024 (7)0.0170 (11)
C18A0.0308 (12)0.0476 (13)0.0399 (10)0.0011 (11)0.0067 (11)0.0180 (8)
O210.0425 (12)0.0566 (13)0.0468 (12)0.0022 (10)0.0208 (9)0.0103 (10)
O220.0325 (7)0.0490 (12)0.0502 (11)0.0090 (8)0.0053 (9)0.0154 (8)
N210.0414 (9)0.0349 (14)0.0341 (14)0.0019 (11)0.0129 (12)0.0096 (10)
N220.0359 (10)0.0362 (14)0.0373 (14)0.0090 (10)0.0017 (11)0.0080 (10)
C210.0316 (8)0.022 (3)0.029 (2)0.0010 (9)0.0056 (10)0.0073 (14)
C220.0299 (9)0.021 (2)0.029 (2)0.0012 (11)0.0039 (9)0.0045 (14)
C230.0347 (15)0.026 (2)0.0290 (17)0.0004 (19)0.0030 (8)0.0065 (12)
C240.0252 (12)0.0263 (18)0.0356 (7)0.0058 (16)0.0033 (8)0.0158 (7)
C250.0327 (7)0.019 (2)0.0354 (6)0.0043 (7)0.0024 (5)0.0163 (9)
C260.0428 (9)0.016 (3)0.0312 (13)0.0041 (7)0.0051 (8)0.0051 (9)
C270.0321 (19)0.0471 (18)0.0437 (12)0.0014 (19)0.0084 (16)0.0207 (9)
C280.0369 (10)0.0489 (9)0.0468 (18)0.0181 (10)0.0061 (8)0.0222 (17)
O21A0.0352 (11)0.0519 (12)0.0583 (13)0.0208 (9)0.0062 (9)0.0072 (10)
O22A0.0325 (7)0.0490 (12)0.0502 (11)0.0090 (8)0.0053 (9)0.0154 (8)
N21A0.0359 (10)0.0362 (14)0.0373 (14)0.0090 (10)0.0017 (11)0.0080 (10)
N22A0.0414 (9)0.0349 (14)0.0341 (14)0.0019 (11)0.0129 (12)0.0096 (10)
C21A0.0299 (9)0.021 (2)0.029 (2)0.0012 (11)0.0039 (9)0.0045 (14)
C22A0.0316 (8)0.022 (3)0.029 (2)0.0010 (9)0.0056 (10)0.0073 (14)
C23A0.0428 (9)0.016 (3)0.0312 (13)0.0041 (7)0.0051 (8)0.0051 (9)
C24A0.0327 (7)0.019 (2)0.0354 (6)0.0043 (7)0.0024 (5)0.0163 (9)
C25A0.0252 (12)0.0263 (18)0.0356 (7)0.0058 (16)0.0033 (8)0.0158 (7)
C26A0.0347 (15)0.026 (2)0.0290 (17)0.0004 (19)0.0030 (8)0.0065 (12)
C27A0.0369 (10)0.0489 (9)0.0468 (18)0.0181 (10)0.0061 (8)0.0222 (17)
C28A0.0321 (19)0.0471 (18)0.0437 (12)0.0014 (19)0.0084 (16)0.0207 (9)
O310.0326 (10)0.0538 (11)0.0506 (11)0.0022 (8)0.0176 (8)0.0108 (9)
O320.0281 (6)0.0447 (11)0.0502 (12)0.0100 (8)0.0023 (8)0.0145 (8)
N310.0307 (7)0.0306 (14)0.0378 (15)0.0034 (10)0.0039 (11)0.0094 (10)
N320.0347 (10)0.0357 (15)0.0387 (15)0.0092 (10)0.0027 (11)0.0089 (11)
C310.0269 (7)0.024 (2)0.0291 (19)0.0030 (7)0.0021 (8)0.0081 (13)
C320.0274 (8)0.021 (2)0.0290 (18)0.0035 (10)0.0001 (8)0.0056 (12)
C330.0338 (13)0.026 (2)0.0303 (15)0.0001 (18)0.0017 (8)0.0064 (10)
C340.0256 (10)0.0246 (19)0.0340 (6)0.0059 (13)0.0024 (7)0.0160 (8)
C350.0290 (6)0.022 (2)0.0348 (6)0.0071 (6)0.0020 (5)0.0173 (8)
C360.0343 (8)0.020 (3)0.0297 (13)0.0074 (6)0.0022 (8)0.0056 (9)
C370.0294 (14)0.0503 (13)0.0423 (12)0.0000 (19)0.0062 (15)0.0218 (9)
C380.0319 (10)0.0509 (10)0.0415 (13)0.0154 (15)0.0045 (8)0.0203 (11)
O31A0.0423 (14)0.0481 (13)0.0497 (14)0.0199 (11)0.0101 (11)0.0047 (11)
O32A0.0281 (6)0.0447 (11)0.0502 (12)0.0100 (8)0.0023 (8)0.0145 (8)
N31A0.0347 (10)0.0357 (15)0.0387 (15)0.0092 (10)0.0027 (11)0.0089 (11)
N32A0.0307 (7)0.0306 (14)0.0378 (15)0.0034 (10)0.0039 (11)0.0094 (10)
C31A0.0274 (8)0.021 (2)0.0290 (18)0.0035 (10)0.0001 (8)0.0056 (12)
C32A0.0269 (7)0.024 (2)0.0291 (19)0.0030 (7)0.0021 (8)0.0081 (13)
C33A0.0343 (8)0.020 (3)0.0297 (13)0.0074 (6)0.0022 (8)0.0056 (9)
C34A0.0290 (6)0.022 (2)0.0348 (6)0.0071 (6)0.0020 (5)0.0173 (8)
C35A0.0256 (10)0.0246 (19)0.0340 (6)0.0059 (13)0.0024 (7)0.0160 (8)
C36A0.0338 (13)0.026 (2)0.0303 (15)0.0001 (18)0.0017 (8)0.0064 (10)
C37A0.0319 (10)0.0509 (10)0.0415 (13)0.0154 (15)0.0045 (8)0.0203 (11)
C38A0.0294 (14)0.0503 (13)0.0423 (12)0.0000 (19)0.0062 (15)0.0218 (9)
Geometric parameters (Å, º) top
O11—N111.2389 (14)O21A—N21A1.2390 (14)
O12—N121.3808 (14)O22A—N22A1.3812 (14)
O12—N111.4416 (14)O22A—N21A1.4417 (14)
N11—C111.3373 (19)N21A—C21A1.3373 (19)
N12—C121.3359 (18)N22A—C22A1.3363 (19)
C11—C121.4015 (15)C21A—C22A1.4012 (16)
C11—C161.414 (2)C21A—C26A1.414 (2)
C12—C131.417 (2)C22A—C23A1.417 (2)
C13—C141.373 (2)C23A—C24A1.373 (2)
C13—H130.9500C23A—H23A0.9500
C14—C151.4619 (12)C24A—C25A1.4621 (13)
C14—C171.499 (2)C24A—C27A1.500 (2)
C15—C161.361 (2)C25A—C26A1.361 (2)
C15—C181.508 (2)C25A—C28A1.508 (2)
C16—H160.9500C26A—H26A0.9500
C17—H17A0.9800C27A—H27D0.9800
C17—H17B0.9800C27A—H27E0.9800
C17—H17C0.9800C27A—H27F0.9800
C18—H18A0.9800C28A—H28D0.9800
C18—H18B0.9800C28A—H28E0.9800
C18—H18C0.9800C28A—H28F0.9800
O11A—N11A1.2390 (15)O31—N311.2393 (14)
O12A—N12A1.3809 (14)O32—N321.3811 (14)
O12A—N11A1.4413 (14)O32—N311.4410 (14)
N11A—C11A1.337 (2)N31—C311.3374 (19)
N12A—C12A1.3365 (19)N32—C321.3361 (19)
C11A—C12A1.4013 (16)C31—C321.4014 (16)
C11A—C16A1.414 (2)C31—C361.414 (2)
C12A—C13A1.417 (2)C32—C331.417 (2)
C13A—C14A1.373 (2)C33—C341.373 (2)
C13A—H13A0.9500C33—H330.9500
C14A—C15A1.4625 (13)C34—C351.4626 (13)
C14A—C17A1.499 (2)C34—C371.500 (2)
C15A—C16A1.361 (2)C35—C361.360 (2)
C15A—C18A1.509 (2)C35—C381.509 (2)
C16A—H16A0.9500C36—H360.9500
C17A—H17D0.9800C37—H37A0.9800
C17A—H17E0.9800C37—H37B0.9800
C17A—H17F0.9800C37—H37C0.9800
C18A—H18D0.9800C38—H38A0.9800
C18A—H18E0.9800C38—H38B0.9800
C18A—H18F0.9800C38—H38C0.9800
O21—N211.2390 (14)O31A—N31A1.2391 (14)
O22—N221.3810 (14)O32A—N32A1.3809 (14)
O22—N211.4414 (14)O32A—N31A1.4413 (14)
N21—C211.3375 (19)N31A—C31A1.3373 (19)
N22—C221.3363 (19)N32A—C32A1.3366 (19)
C21—C221.4012 (16)C31A—C32A1.4013 (16)
C21—C261.414 (2)C31A—C36A1.414 (2)
C22—C231.417 (2)C32A—C33A1.417 (2)
C23—C241.373 (2)C33A—C34A1.373 (2)
C23—H230.9500C33A—H33A0.9500
C24—C251.4619 (13)C34A—C35A1.4626 (13)
C24—C271.499 (2)C34A—C37A1.500 (2)
C25—C261.361 (2)C35A—C36A1.361 (2)
C25—C281.509 (2)C35A—C38A1.509 (2)
C26—H260.9500C36A—H36A0.9500
C27—H27A0.9800C37A—H37D0.9800
C27—H27B0.9800C37A—H37E0.9800
C27—H27C0.9800C37A—H37F0.9800
C28—H28A0.9800C38A—H38D0.9800
C28—H28B0.9800C38A—H38E0.9800
C28—H28C0.9800C38A—H38F0.9800
N12—O12—N11109.02 (9)N22A—O22A—N21A109.01 (9)
O11—N11—C11135.08 (13)O21A—N21A—C21A135.13 (14)
O11—N11—O12118.57 (11)O21A—N21A—O22A118.52 (11)
C11—N11—O12106.34 (10)C21A—N21A—O22A106.34 (10)
C12—N12—O12105.41 (10)C22A—N22A—O22A105.40 (11)
N11—C11—C12107.35 (14)N21A—C21A—C22A107.37 (14)
N11—C11—C16129.64 (14)N21A—C21A—C26A129.63 (15)
C12—C11—C16123.01 (16)C22A—C21A—C26A122.99 (17)
N12—C12—C11111.87 (14)N22A—C22A—C21A111.87 (15)
N12—C12—C13128.64 (13)N22A—C22A—C23A128.62 (14)
C11—C12—C13119.49 (15)C21A—C22A—C23A119.49 (16)
C14—C13—C12118.40 (13)C24A—C23A—C22A118.41 (14)
C14—C13—H13120.8C24A—C23A—H23A120.8
C12—C13—H13120.8C22A—C23A—H23A120.8
C13—C14—C15120.92 (17)C23A—C24A—C25A120.89 (19)
C13—C14—C17120.05 (16)C23A—C24A—C27A119.89 (17)
C15—C14—C17119.01 (18)C25A—C24A—C27A118.96 (19)
C16—C15—C14121.07 (17)C26A—C25A—C24A121.05 (18)
C16—C15—C18119.56 (16)C26A—C25A—C28A119.52 (18)
C14—C15—C18119.35 (18)C24A—C25A—C28A119.32 (19)
C15—C16—C11117.12 (14)C25A—C26A—C21A117.12 (15)
C15—C16—H16121.4C25A—C26A—H26A121.4
C11—C16—H16121.4C21A—C26A—H26A121.4
C14—C17—H17A109.5C24A—C27A—H27D109.5
C14—C17—H17B109.5C24A—C27A—H27E109.5
H17A—C17—H17B109.5H27D—C27A—H27E109.5
C14—C17—H17C109.5C24A—C27A—H27F109.5
H17A—C17—H17C109.5H27D—C27A—H27F109.5
H17B—C17—H17C109.5H27E—C27A—H27F109.5
C15—C18—H18A109.5C25A—C28A—H28D109.5
C15—C18—H18B109.5C25A—C28A—H28E109.5
H18A—C18—H18B109.5H28D—C28A—H28E109.5
C15—C18—H18C109.5C25A—C28A—H28F109.5
H18A—C18—H18C109.5H28D—C28A—H28F109.5
H18B—C18—H18C109.5H28E—C28A—H28F109.5
N12A—O12A—N11A109.03 (9)N32—O32—N31109.01 (9)
O11A—N11A—C11A135.09 (14)O31—N31—C31135.05 (13)
O11A—N11A—O12A118.58 (12)O31—N31—O32118.59 (11)
C11A—N11A—O12A106.33 (11)C31—N31—O32106.36 (10)
C12A—N12A—O12A105.40 (11)C32—N32—O32105.43 (10)
N11A—C11A—C12A107.38 (14)N31—C31—C32107.37 (14)
N11A—C11A—C16A129.62 (15)N31—C31—C36129.61 (15)
C12A—C11A—C16A123.00 (17)C32—C31—C36122.98 (17)
N12A—C12A—C11A111.84 (15)N32—C32—C31111.84 (14)
N12A—C12A—C13A128.59 (15)N32—C32—C33128.67 (14)
C11A—C12A—C13A119.46 (17)C31—C32—C33119.49 (16)
C14A—C13A—C12A118.40 (14)C34—C33—C32118.41 (14)
C14A—C13A—H13A120.8C34—C33—H33120.8
C12A—C13A—H13A120.8C32—C33—H33120.8
C13A—C14A—C15A120.9 (2)C33—C34—C35120.87 (18)
C13A—C14A—C17A120.00 (18)C33—C34—C37120.00 (17)
C15A—C14A—C17A118.9 (2)C35—C34—C37118.91 (19)
C16A—C15A—C14A121.0 (2)C36—C35—C34121.05 (18)
C16A—C15A—C18A119.45 (18)C36—C35—C38119.46 (17)
C14A—C15A—C18A119.3 (2)C34—C35—C38119.24 (19)
C15A—C16A—C11A117.11 (15)C35—C36—C31117.15 (14)
C15A—C16A—H16A121.4C35—C36—H36121.4
C11A—C16A—H16A121.4C31—C36—H36121.4
C14A—C17A—H17D109.5C34—C37—H37A109.5
C14A—C17A—H17E109.5C34—C37—H37B109.5
H17D—C17A—H17E109.5H37A—C37—H37B109.5
C14A—C17A—H17F109.5C34—C37—H37C109.5
H17D—C17A—H17F109.5H37A—C37—H37C109.5
H17E—C17A—H17F109.5H37B—C37—H37C109.5
C15A—C18A—H18D109.5C35—C38—H38A109.5
C15A—C18A—H18E109.5C35—C38—H38B109.5
H18D—C18A—H18E109.5H38A—C38—H38B109.5
C15A—C18A—H18F109.5C35—C38—H38C109.5
H18D—C18A—H18F109.5H38A—C38—H38C109.5
H18E—C18A—H18F109.5H38B—C38—H38C109.5
N22—O22—N21109.01 (9)N32A—O32A—N31A109.04 (9)
O21—N21—C21135.09 (14)O31A—N31A—C31A135.14 (14)
O21—N21—O22118.58 (11)O31A—N31A—O32A118.52 (12)
C21—N21—O22106.34 (10)C31A—N31A—O32A106.34 (10)
C22—N22—O22105.41 (11)C32A—N32A—O32A105.39 (11)
N21—C21—C22107.38 (14)N31A—C31A—C32A107.37 (14)
N21—C21—C26129.60 (15)N31A—C31A—C36A129.63 (15)
C22—C21—C26123.00 (17)C32A—C31A—C36A123.00 (17)
N22—C22—C21111.85 (15)N32A—C32A—C31A111.86 (15)
N22—C22—C23128.67 (14)N32A—C32A—C33A128.60 (14)
C21—C22—C23119.49 (16)C31A—C32A—C33A119.46 (16)
C24—C23—C22118.39 (14)C34A—C33A—C32A118.44 (14)
C24—C23—H23120.8C34A—C33A—H33A120.8
C22—C23—H23120.8C32A—C33A—H33A120.8
C23—C24—C25120.88 (19)C33A—C34A—C35A120.90 (19)
C23—C24—C27120.03 (17)C33A—C34A—C37A119.96 (18)
C25—C24—C27119.02 (19)C35A—C34A—C37A118.90 (19)
C26—C25—C24121.06 (18)C36A—C35A—C34A121.02 (18)
C26—C25—C28119.41 (17)C36A—C35A—C38A119.46 (18)
C24—C25—C28119.3 (2)C34A—C35A—C38A119.2 (2)
C25—C26—C21117.11 (15)C35A—C36A—C31A117.13 (15)
C25—C26—H26121.4C35A—C36A—H36A121.4
C21—C26—H26121.4C31A—C36A—H36A121.4
C24—C27—H27A109.5C34A—C37A—H37D109.5
C24—C27—H27B109.5C34A—C37A—H37E109.5
H27A—C27—H27B109.5H37D—C37A—H37E109.5
C24—C27—H27C109.5C34A—C37A—H37F109.5
H27A—C27—H27C109.5H37D—C37A—H37F109.5
H27B—C27—H27C109.5H37E—C37A—H37F109.5
C25—C28—H28A109.5C35A—C38A—H38D109.5
C25—C28—H28B109.5C35A—C38A—H38E109.5
H28A—C28—H28B109.5H38D—C38A—H38E109.5
C25—C28—H28C109.5C35A—C38A—H38F109.5
H28A—C28—H28C109.5H38D—C38A—H38F109.5
H28B—C28—H28C109.5H38E—C38A—H38F109.5
N12—O12—N11—O11179.91 (14)N22A—O22A—N21A—O21A179.6 (3)
N12—O12—N11—C110.1 (2)N22A—O22A—N21A—C21A0.6 (4)
N11—O12—N12—C120.0 (2)N21A—O22A—N22A—C22A0.5 (4)
O11—N11—C11—C12179.9 (2)O21A—N21A—C21A—C22A179.8 (4)
O12—N11—C11—C120.2 (3)O22A—N21A—C21A—C22A0.4 (6)
O11—N11—C11—C160.6 (5)O21A—N21A—C21A—C26A0.4 (13)
O12—N11—C11—C16179.7 (4)O22A—N21A—C21A—C26A179.8 (9)
O12—N12—C12—C110.1 (3)O22A—N22A—C22A—C21A0.3 (6)
O12—N12—C12—C13179.8 (3)O22A—N22A—C22A—C23A178.0 (9)
N11—C11—C12—N120.2 (3)N21A—C21A—C22A—N22A0.1 (7)
C16—C11—C12—N12179.8 (3)C26A—C21A—C22A—N22A179.5 (9)
N11—C11—C12—C13179.7 (3)N21A—C21A—C22A—C23A178.5 (8)
C16—C11—C12—C130.1 (5)C26A—C21A—C22A—C23A2.1 (13)
N12—C12—C13—C14178.9 (3)N22A—C22A—C23A—C24A178.2 (8)
C11—C12—C13—C141.0 (5)C21A—C22A—C23A—C24A0.1 (14)
C12—C13—C14—C151.3 (6)C22A—C23A—C24A—C25A1.4 (14)
C12—C13—C14—C17179.7 (4)C22A—C23A—C24A—C27A175.5 (12)
C13—C14—C15—C160.7 (7)C23A—C24A—C25A—C26A1.1 (14)
C17—C14—C15—C16179.2 (5)C27A—C24A—C25A—C26A175.3 (14)
C13—C14—C15—C18179.3 (5)C23A—C24A—C25A—C28A175.2 (13)
C17—C14—C15—C182.3 (6)C27A—C24A—C25A—C28A1.0 (13)
C14—C15—C16—C110.1 (7)C24A—C25A—C26A—C21A0.8 (16)
C18—C15—C16—C11178.4 (5)C28A—C25A—C26A—C21A177.1 (12)
N11—C11—C16—C15179.1 (4)N21A—C21A—C26A—C25A178.4 (9)
C12—C11—C16—C150.4 (6)C22A—C21A—C26A—C25A2.4 (15)
N12A—O12A—N11A—O11A179.7 (5)N32—O32—N31—O31179.3 (2)
N12A—O12A—N11A—C11A0.5 (8)N32—O32—N31—C310.0 (4)
N11A—O12A—N12A—C12A1.1 (8)N31—O32—N32—C320.3 (4)
O11A—N11A—C11A—C12A179.6 (8)O31—N31—C31—C32179.4 (4)
O12A—N11A—C11A—C12A0.3 (10)O32—N31—C31—C320.3 (5)
O11A—N11A—C11A—C16A0 (2)O31—N31—C31—C362.9 (11)
O12A—N11A—C11A—C16A180.0 (13)O32—N31—C31—C36177.9 (7)
O12A—N12A—C12A—C11A1.2 (11)O32—N32—C32—C310.5 (6)
O12A—N12A—C12A—C13A177.5 (13)O32—N32—C32—C33178.8 (8)
N11A—C11A—C12A—N12A1.0 (13)N31—C31—C32—N320.5 (7)
C16A—C11A—C12A—N12A179.3 (12)C36—C31—C32—N32178.3 (7)
N11A—C11A—C12A—C13A177.6 (12)N31—C31—C32—C33178.9 (7)
C16A—C11A—C12A—C13A3 (2)C36—C31—C32—C331.0 (11)
N12A—C12A—C13A—C14A178.7 (14)N32—C32—C33—C34176.8 (7)
C11A—C12A—C13A—C14A3 (2)C31—C32—C33—C342.5 (13)
C12A—C13A—C14A—C15A3 (2)C32—C33—C34—C351.9 (12)
C12A—C13A—C14A—C17A178.3 (17)C32—C33—C34—C37176.4 (10)
C13A—C14A—C15A—C16A4 (2)C33—C34—C35—C360.2 (11)
C17A—C14A—C15A—C16A178.8 (17)C37—C34—C35—C36174.3 (10)
C13A—C14A—C15A—C18A177.5 (17)C33—C34—C35—C38174.6 (11)
C17A—C14A—C15A—C18A7 (2)C37—C34—C35—C380.0 (10)
C14A—C15A—C16A—C11A3 (2)C34—C35—C36—C311.7 (12)
C18A—C15A—C16A—C11A177.2 (15)C38—C35—C36—C31176.0 (11)
N11A—C11A—C16A—C15A177.3 (13)N31—C31—C36—C35176.3 (7)
C12A—C11A—C16A—C15A3 (2)C32—C31—C36—C351.0 (12)
N22—O22—N21—O21178.6 (3)N32A—O32A—N31A—O31A179.9 (3)
N22—O22—N21—C211.1 (4)N32A—O32A—N31A—C31A0.7 (6)
N21—O22—N22—C221.1 (4)N31A—O32A—N32A—C32A0.1 (6)
O21—N21—C21—C22179.0 (4)O31A—N31A—C31A—C32A179.6 (6)
O22—N21—C21—C220.6 (6)O32A—N31A—C31A—C32A1.1 (8)
O21—N21—C21—C262.9 (12)O31A—N31A—C31A—C36A0.1 (16)
O22—N21—C21—C26177.4 (9)O32A—N31A—C31A—C36A179.3 (11)
O22—N22—C22—C210.7 (6)O32A—N32A—C32A—C31A0.8 (8)
O22—N22—C22—C23179.5 (9)O32A—N32A—C32A—C33A177.4 (10)
N21—C21—C22—N220.0 (7)N31A—C31A—C32A—N32A1.3 (9)
C26—C21—C22—N22178.3 (8)C36A—C31A—C32A—N32A179.1 (10)
N21—C21—C22—C23179.8 (8)N31A—C31A—C32A—C33A178.2 (10)
C26—C21—C22—C232.0 (12)C36A—C31A—C32A—C33A2.2 (15)
N22—C22—C23—C24177.6 (9)N32A—C32A—C33A—C34A177.8 (10)
C21—C22—C23—C242.7 (15)C31A—C32A—C33A—C34A1.4 (16)
C22—C23—C24—C251.0 (16)C32A—C33A—C34A—C35A1.0 (16)
C22—C23—C24—C27177.8 (12)C32A—C33A—C34A—C37A173.3 (15)
C23—C24—C25—C261.5 (14)C33A—C34A—C35A—C36A1.3 (14)
C27—C24—C25—C26175.3 (13)C37A—C34A—C35A—C36A173.1 (15)
C23—C24—C25—C28176.3 (14)C33A—C34A—C35A—C38A174.8 (13)
C27—C24—C25—C280.6 (13)C37A—C34A—C35A—C38A0.4 (14)
C24—C25—C26—C212.2 (14)C34A—C35A—C36A—C31A1.9 (17)
C28—C25—C26—C21177.0 (11)C38A—C35A—C36A—C31A175.4 (13)
N21—C21—C26—C25177.3 (8)N31A—C31A—C36A—C35A178.1 (10)
C22—C21—C26—C250.5 (14)C32A—C31A—C36A—C35A2.4 (18)
(Z10) 5,6-benzfurazan 1-oxide - polymorph Z10 top
Crystal data top
C8H8N2O2Z = 10
Mr = 164.16F(000) = 860
Triclinic, P1Dx = 1.417 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.0136 (18) ÅCell parameters from 2747 reflections
b = 13.064 (3) Åθ = 2.4–27.1°
c = 16.567 (3) ŵ = 0.11 mm1
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
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
8722 independent reflections
Radiation source: fine-focus sealed tube3791 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan
SADABS: Sheldrick, 2008; Blessing, 1995
h = 1111
Tmin = 0.96, Tmax = 0.98k = 1616
22419 measured reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.114Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.338H-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 parametersΔρmax = 1.18 e Å3
1440 restraintsΔρmin = 0.39 e Å3
Crystal data top
C8H8N2O2γ = 90.742 (4)°
Mr = 164.16V = 1923.9 (7) Å3
Triclinic, P1Z = 10
a = 9.0136 (18) ÅMo Kα radiation
b = 13.064 (3) ŵ = 0.11 mm1
c = 16.567 (3) ÅT = 173 K
α = 95.055 (4)°0.40 × 0.35 × 0.20 mm
β = 97.969 (4)°
Data collection top
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 = 0.98Rint = 0.054
22419 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.1141440 restraints
wR(F2) = 0.338H-atom parameters constrained
S = 0.97Δρmax = 1.18 e Å3
8722 reflectionsΔρmin = 0.39 e Å3
756 parameters
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C110.0692 (5)0.4871 (2)0.1077 (9)0.0257 (10)0.546 (2)
C120.0633 (5)0.3792 (2)0.1012 (9)0.0230 (10)0.546 (2)
C130.0746 (6)0.3318 (3)0.0928 (15)0.0259 (11)0.546 (2)
H130.08070.25900.08770.031*0.546 (2)
C140.1986 (6)0.3927 (4)0.0922 (13)0.0237 (9)0.546 (2)
C150.1888 (7)0.5049 (4)0.0961 (15)0.0238 (8)0.546 (2)
C160.0565 (7)0.5517 (3)0.1053 (16)0.0264 (9)0.546 (2)
H160.04960.62440.10990.032*0.546 (2)
C170.3461 (9)0.3455 (5)0.081 (2)0.0348 (9)0.546 (2)
H17A0.33560.27050.07900.052*0.546 (2)
H17B0.42140.37010.12790.052*0.546 (2)
H17C0.37780.36500.03060.052*0.546 (2)
C180.3286 (11)0.5696 (5)0.096 (3)0.0372 (8)0.546 (2)
H18A0.30360.64250.10010.056*0.546 (2)
H18B0.37110.55200.04580.056*0.546 (2)
H18C0.40200.55640.14360.056*0.546 (2)
N110.2096 (3)0.51036 (18)0.1178 (3)0.0303 (9)0.546 (2)
N120.1963 (4)0.33506 (19)0.1045 (3)0.0320 (10)0.546 (2)
O110.2762 (3)0.59255 (18)0.1268 (2)0.0431 (10)0.546 (2)
O120.2920 (3)0.41516 (18)0.1151 (2)0.0361 (8)0.546 (2)
C310.1377 (4)0.3904 (2)0.3007 (8)0.0249 (9)0.598 (3)
C320.1451 (4)0.2826 (2)0.2958 (7)0.0265 (10)0.598 (3)
C330.2852 (4)0.2360 (3)0.2926 (11)0.0305 (12)0.598 (3)
H330.29200.16330.28670.037*0.598 (3)
C340.4104 (4)0.2976 (3)0.2981 (9)0.0270 (12)0.598 (3)
C350.3998 (4)0.4098 (3)0.3022 (9)0.0270 (6)0.598 (3)
C360.2645 (5)0.4557 (3)0.3032 (12)0.0263 (9)0.598 (3)
H360.25620.52830.30550.032*0.598 (3)
C370.5606 (5)0.2514 (4)0.2935 (14)0.0368 (14)0.598 (3)
H37A0.55000.17630.28860.055*0.598 (3)
H37B0.62910.27430.34330.055*0.598 (3)
H37C0.60100.27340.24570.055*0.598 (3)
C380.5383 (4)0.4747 (4)0.2997 (8)0.0316 (18)0.598 (3)
H38A0.51390.54760.30570.047*0.598 (3)
H38B0.57540.45870.24720.047*0.598 (3)
H38C0.61580.46000.34450.047*0.598 (3)
N310.0053 (3)0.41285 (18)0.3049 (3)0.0305 (9)0.598 (3)
N320.0107 (3)0.23768 (19)0.2937 (3)0.0366 (11)0.598 (3)
O310.0736 (3)0.49470 (18)0.3115 (2)0.0474 (10)0.598 (3)
O320.0875 (3)0.31723 (17)0.2998 (2)0.0393 (9)0.598 (3)
C510.9965 (3)0.21124 (18)0.4933 (3)0.0236 (7)0.810 (3)
C520.9921 (3)0.31917 (17)0.5004 (3)0.0234 (7)0.810 (3)
C530.8548 (3)0.3674 (2)0.5091 (5)0.0265 (7)0.810 (3)
H530.84960.44020.51430.032*0.810 (3)
C540.7301 (3)0.3072 (2)0.5098 (5)0.0223 (6)0.810 (3)
C550.7371 (3)0.1948 (2)0.5016 (5)0.0223 (8)0.810 (3)
C560.8693 (3)0.1473 (2)0.4938 (5)0.0249 (8)0.810 (3)
H560.87530.07450.48880.030*0.810 (3)
C570.5821 (4)0.3552 (3)0.5177 (6)0.0327 (8)0.810 (3)
H57A0.59450.43020.52260.049*0.810 (3)
H57B0.54490.33360.56660.049*0.810 (3)
H57C0.51020.33310.46920.049*0.810 (3)
C580.5971 (5)0.1310 (3)0.5029 (10)0.0353 (13)0.810 (3)
H58A0.62040.05790.49700.053*0.810 (3)
H58B0.52100.14640.45770.053*0.810 (3)
H58C0.55880.14720.55500.053*0.810 (3)
N511.1376 (2)0.18727 (16)0.48532 (18)0.0290 (7)0.810 (3)
N521.1257 (2)0.36267 (16)0.49752 (19)0.0327 (7)0.810 (3)
O511.2037 (2)0.10475 (13)0.47714 (14)0.0405 (7)0.810 (3)
O521.22086 (18)0.28206 (14)0.48775 (14)0.0333 (6)0.810 (3)
C410.8640 (4)0.1857 (2)0.7114 (8)0.0316 (11)0.545 (2)
C420.8685 (4)0.0778 (2)0.7038 (7)0.0266 (10)0.545 (2)
C431.0052 (6)0.0298 (3)0.6932 (13)0.0320 (9)0.545 (2)
H431.00960.04300.68520.038*0.545 (2)
C441.1306 (5)0.0900 (3)0.6948 (12)0.0269 (13)0.545 (2)
C451.1243 (5)0.2024 (3)0.7055 (9)0.0242 (17)0.545 (2)
C460.9921 (5)0.2498 (3)0.7140 (9)0.0286 (17)0.545 (2)
H460.98690.32250.72120.034*0.545 (2)
C471.2761 (9)0.0425 (5)0.6802 (19)0.0406 (10)0.545 (2)
H47A1.26330.03250.67330.061*0.545 (2)
H47B1.35280.06230.72720.061*0.545 (2)
H47C1.30750.06670.63070.061*0.545 (2)
C481.2632 (8)0.2665 (5)0.7020 (17)0.038 (2)0.545 (2)
H48A1.24070.33950.71040.056*0.545 (2)
H48B1.29660.25220.64840.056*0.545 (2)
H48C1.34260.24930.74500.056*0.545 (2)
N410.7228 (3)0.20946 (19)0.7193 (3)0.0341 (10)0.545 (2)
N420.7346 (4)0.03409 (19)0.7056 (4)0.0370 (10)0.545 (2)
O410.6561 (3)0.29187 (18)0.7263 (2)0.0466 (11)0.545 (2)
O420.6396 (3)0.11456 (18)0.7166 (3)0.0445 (9)0.545 (2)
C210.0707 (3)0.0891 (2)0.9044 (7)0.0234 (9)0.619 (3)
C220.0775 (3)0.0187 (2)0.8974 (5)0.0240 (9)0.619 (3)
C230.2177 (4)0.0654 (3)0.8949 (7)0.0260 (12)0.619 (3)
H230.22510.13800.89130.031*0.619 (3)
C240.3423 (4)0.0038 (3)0.8976 (7)0.0205 (11)0.619 (3)
C250.3330 (4)0.1084 (3)0.9067 (7)0.0189 (14)0.619 (3)
C260.1976 (4)0.1544 (3)0.9073 (11)0.0242 (10)0.619 (3)
H260.18940.22700.90960.029*0.619 (3)
C270.4906 (6)0.0500 (4)0.8873 (16)0.0330 (8)0.619 (3)
H27A0.48020.12510.88280.050*0.619 (3)
H27B0.56440.02700.93480.050*0.619 (3)
H27C0.52400.02810.83750.050*0.619 (3)
C280.4730 (5)0.1738 (4)0.9097 (11)0.0306 (19)0.619 (3)
H28A0.44780.24660.91500.046*0.619 (3)
H28B0.51700.15830.85920.046*0.619 (3)
H28C0.54530.15890.95680.046*0.619 (3)
N210.0722 (3)0.11152 (18)0.9087 (3)0.0290 (8)0.619 (3)
N220.0565 (3)0.06365 (18)0.8966 (3)0.0339 (10)0.619 (3)
O210.1410 (3)0.19329 (17)0.9143 (2)0.0429 (9)0.619 (3)
O220.1544 (2)0.01588 (17)0.9037 (2)0.0371 (8)0.619 (3)
C21A0.0644 (5)0.0113 (3)0.8959 (9)0.0240 (9)0.381 (3)
C22A0.0698 (5)0.1194 (3)0.9030 (12)0.0234 (9)0.381 (3)
C23A0.2084 (7)0.1717 (4)0.9032 (19)0.0242 (10)0.381 (3)
H23A0.21510.24460.90990.029*0.381 (3)
C24A0.3321 (6)0.1151 (5)0.8937 (13)0.0189 (14)0.381 (3)
C25A0.3243 (5)0.0025 (5)0.8873 (13)0.0205 (11)0.381 (3)
C26A0.1907 (6)0.0489 (4)0.8863 (12)0.0260 (12)0.381 (3)
H26A0.18330.12180.87930.031*0.381 (3)
C27A0.4819 (8)0.1674 (6)0.896 (2)0.0306 (19)0.381 (3)
H27D0.47040.24210.90110.046*0.381 (3)
H27E0.52320.14660.84570.046*0.381 (3)
H27F0.55010.14780.94330.046*0.381 (3)
C28A0.4668 (8)0.0569 (6)0.889 (3)0.0330 (8)0.381 (3)
H28D0.44260.13070.88340.050*0.381 (3)
H28E0.53200.03840.94050.050*0.381 (3)
H28F0.51840.04010.84300.050*0.381 (3)
N21A0.0786 (4)0.0168 (2)0.8955 (6)0.0339 (10)0.381 (3)
N22A0.0653 (5)0.1589 (2)0.9056 (5)0.0290 (8)0.381 (3)
O21A0.1459 (5)0.1013 (2)0.8916 (4)0.0470 (15)0.381 (3)
O22A0.1624 (4)0.0755 (2)0.9013 (4)0.0371 (8)0.381 (3)
C41A0.8553 (5)0.1095 (3)0.7009 (8)0.0266 (10)0.455 (2)
C42A0.8653 (5)0.2175 (3)0.7082 (10)0.0316 (11)0.455 (2)
C43A1.0028 (6)0.2668 (3)0.7007 (11)0.0286 (17)0.455 (2)
H43A1.01070.33960.70280.034*0.455 (2)
C44A1.1237 (6)0.2077 (4)0.6903 (11)0.0242 (17)0.455 (2)
C45A1.1124 (7)0.0953 (4)0.6867 (14)0.0269 (13)0.455 (2)
C46A0.9796 (7)0.0467 (3)0.6928 (16)0.0320 (9)0.455 (2)
H46A0.97140.02600.69160.038*0.455 (2)
C47A1.2743 (9)0.2571 (6)0.689 (2)0.038 (2)0.455 (2)
H47D1.26460.33190.69050.056*0.455 (2)
H47E1.31340.23170.63880.056*0.455 (2)
H47F1.34340.24010.73670.056*0.455 (2)
C48A1.2515 (10)0.0333 (6)0.683 (2)0.0406 (10)0.455 (2)
H48D1.22600.03990.68280.061*0.455 (2)
H48E1.32600.05470.73040.061*0.455 (2)
H48F1.29290.04460.63250.061*0.455 (2)
N41A0.7140 (4)0.0843 (2)0.7081 (4)0.0370 (10)0.455 (2)
N42A0.7343 (5)0.2598 (2)0.7177 (4)0.0341 (10)0.455 (2)
O41A0.6438 (4)0.0012 (2)0.7057 (3)0.0527 (14)0.455 (2)
O42A0.6350 (4)0.1783 (2)0.7169 (3)0.0445 (9)0.455 (2)
C51A1.0041 (7)0.2898 (4)0.4978 (12)0.0234 (7)0.190 (3)
C52A0.9953 (7)0.1819 (4)0.4940 (12)0.0236 (7)0.190 (3)
C53A0.8580 (11)0.1328 (6)0.502 (2)0.0249 (8)0.190 (3)
H53A0.85080.06010.50190.030*0.190 (3)
C54A0.7360 (10)0.1918 (7)0.510 (2)0.0223 (8)0.190 (3)
C55A0.7463 (8)0.3040 (6)0.510 (2)0.0223 (6)0.190 (3)
C56A0.8802 (10)0.3526 (5)0.507 (2)0.0265 (7)0.190 (3)
H56A0.88940.42550.51010.032*0.190 (3)
C57A0.5856 (18)0.1423 (9)0.511 (5)0.0353 (13)0.190 (3)
H57D0.59580.06770.51130.053*0.190 (3)
H57E0.51720.15770.46270.053*0.190 (3)
H57F0.54530.16920.56070.053*0.190 (3)
C58A0.6101 (13)0.3667 (9)0.521 (3)0.0327 (8)0.190 (3)
H58D0.63460.43960.51900.049*0.190 (3)
H58E0.57860.35640.57420.049*0.190 (3)
H58F0.52850.34480.47730.049*0.190 (3)
N51A1.1471 (6)0.3150 (4)0.4949 (10)0.0327 (7)0.190 (3)
N52A1.1267 (8)0.1395 (4)0.4853 (9)0.0290 (7)0.190 (3)
O51A1.2177 (7)0.3982 (4)0.4986 (6)0.039 (3)0.190 (3)
O52A1.2269 (6)0.2210 (4)0.4884 (7)0.0333 (6)0.190 (3)
C31A0.1331 (5)0.3137 (3)0.2934 (11)0.0265 (10)0.402 (3)
C32A0.1404 (5)0.4217 (3)0.3035 (12)0.0249 (9)0.402 (3)
C33A0.2806 (7)0.4733 (4)0.3079 (19)0.0263 (9)0.402 (3)
H33A0.28800.54620.31490.032*0.402 (3)
C34A0.4051 (5)0.4163 (5)0.3017 (13)0.0270 (6)0.402 (3)
C35A0.3944 (6)0.3037 (5)0.2893 (14)0.0270 (12)0.402 (3)
C36A0.2601 (6)0.2529 (4)0.2875 (18)0.0305 (12)0.402 (3)
H36A0.25270.17990.28250.037*0.402 (3)
C37A0.5577 (6)0.4671 (6)0.3156 (13)0.0316 (18)0.402 (3)
H37D0.54770.54190.31850.047*0.402 (3)
H37E0.61240.44460.27030.047*0.402 (3)
H37F0.61280.44790.36710.047*0.402 (3)
C38A0.5352 (7)0.2433 (6)0.286 (2)0.0368 (14)0.402 (3)
H38D0.51020.16960.28190.055*0.402 (3)
H38E0.60510.26150.33660.055*0.402 (3)
H38F0.58190.25960.23890.055*0.402 (3)
N31A0.0102 (4)0.2862 (2)0.2928 (6)0.0366 (11)0.402 (3)
N32A0.0055 (5)0.4619 (2)0.3052 (6)0.0305 (9)0.402 (3)
O31A0.0781 (5)0.2020 (2)0.2896 (3)0.0481 (15)0.402 (3)
O32A0.0928 (4)0.3789 (2)0.2995 (4)0.0393 (9)0.402 (3)
C11A0.0768 (6)0.4118 (3)0.1024 (11)0.0230 (10)0.454 (2)
C12A0.0671 (6)0.5198 (3)0.1114 (12)0.0257 (10)0.454 (2)
C13A0.0722 (9)0.5699 (4)0.109 (2)0.0264 (9)0.454 (2)
H13A0.08060.64280.11380.032*0.454 (2)
C14A0.1943 (8)0.5113 (4)0.1004 (18)0.0238 (8)0.454 (2)
C15A0.1806 (7)0.3989 (4)0.0886 (16)0.0237 (9)0.454 (2)
C16A0.0466 (8)0.3496 (4)0.0908 (18)0.0259 (11)0.454 (2)
H16A0.03700.27670.08480.031*0.454 (2)
C17A0.3433 (13)0.5613 (6)0.096 (3)0.0372 (8)0.454 (2)
H17D0.33520.63620.10400.056*0.454 (2)
H17E0.37400.54210.04250.056*0.454 (2)
H17F0.41800.53840.13920.056*0.454 (2)
C18A0.3186 (11)0.3368 (6)0.081 (3)0.0348 (9)0.454 (2)
H18D0.29120.26340.07440.052*0.454 (2)
H18E0.39160.35170.13040.052*0.454 (2)
H18F0.36280.35500.03320.052*0.454 (2)
N11A0.2188 (4)0.3860 (2)0.1075 (4)0.0320 (10)0.454 (2)
N12A0.1998 (4)0.5616 (2)0.1178 (4)0.0303 (9)0.454 (2)
O11A0.2879 (4)0.3026 (2)0.1059 (3)0.0456 (12)0.454 (2)
O12A0.2983 (4)0.4797 (2)0.1171 (3)0.0361 (8)0.454 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.0274 (16)0.027 (3)0.0214 (18)0.003 (2)0.0026 (12)0.004 (5)
C120.0267 (18)0.018 (3)0.0251 (15)0.001 (2)0.0036 (16)0.007 (5)
C130.030 (3)0.0190 (19)0.0281 (17)0.0035 (18)0.003 (4)0.008 (4)
C140.0247 (18)0.0259 (15)0.0196 (19)0.0028 (12)0.002 (2)0.0038 (14)
C150.0252 (14)0.0238 (14)0.022 (2)0.0038 (11)0.0020 (13)0.0022 (15)
C160.034 (2)0.0169 (19)0.026 (2)0.0013 (16)0.000 (3)0.001 (4)
C170.031 (3)0.0380 (19)0.0346 (16)0.0095 (18)0.003 (5)0.000 (3)
C180.026 (2)0.0384 (19)0.0474 (17)0.0097 (14)0.005 (4)0.005 (3)
N110.0353 (19)0.023 (3)0.0325 (15)0.006 (3)0.0050 (13)0.001 (3)
N120.033 (2)0.027 (3)0.0362 (16)0.002 (2)0.0045 (15)0.006 (3)
O110.035 (2)0.035 (2)0.061 (2)0.0174 (17)0.0122 (18)0.0011 (17)
O120.0265 (14)0.037 (2)0.0465 (15)0.0016 (18)0.0083 (12)0.006 (2)
C310.0270 (16)0.020 (3)0.0255 (16)0.0046 (17)0.0019 (11)0.004 (4)
C320.0347 (18)0.019 (3)0.0269 (16)0.0032 (18)0.0024 (15)0.011 (4)
C330.035 (2)0.0246 (19)0.031 (3)0.0002 (16)0.004 (3)0.008 (3)
C340.0291 (17)0.0297 (16)0.021 (3)0.0069 (12)0.0043 (19)0.0063 (14)
C350.0263 (15)0.0329 (16)0.0213 (13)0.0080 (11)0.0023 (11)0.0021 (13)
C360.0353 (18)0.0158 (18)0.026 (2)0.0055 (14)0.000 (2)0.002 (3)
C370.022 (2)0.045 (2)0.039 (4)0.0000 (17)0.006 (4)0.005 (2)
C380.0285 (19)0.041 (2)0.024 (5)0.0034 (15)0.003 (2)0.0069 (18)
N310.0223 (16)0.037 (3)0.0321 (14)0.005 (2)0.0030 (12)0.003 (3)
N320.030 (2)0.040 (3)0.0417 (16)0.007 (2)0.0051 (15)0.015 (3)
O310.035 (2)0.047 (2)0.063 (2)0.0214 (17)0.0108 (17)0.0097 (17)
O320.0235 (14)0.047 (3)0.0489 (15)0.0082 (18)0.0042 (11)0.012 (2)
C510.0234 (15)0.0252 (19)0.0215 (13)0.0016 (13)0.0014 (10)0.0009 (17)
C520.0255 (16)0.0204 (18)0.0240 (14)0.0001 (13)0.0024 (11)0.0031 (17)
C530.0311 (18)0.0182 (15)0.0296 (15)0.0007 (12)0.0024 (19)0.0022 (16)
C540.0255 (15)0.0203 (13)0.0206 (12)0.0020 (11)0.0018 (13)0.0012 (10)
C550.0224 (13)0.0233 (14)0.021 (2)0.0041 (10)0.0029 (10)0.0014 (10)
C560.0287 (15)0.0205 (15)0.026 (2)0.0005 (12)0.0033 (12)0.0040 (15)
C570.0258 (19)0.0321 (17)0.0377 (17)0.0045 (14)0.001 (3)0.0058 (17)
C580.0312 (17)0.0292 (17)0.046 (4)0.0095 (13)0.0104 (17)0.001 (2)
N510.0265 (14)0.0273 (17)0.0325 (13)0.0005 (15)0.0020 (11)0.0023 (16)
N520.0311 (17)0.0252 (19)0.0423 (15)0.0029 (15)0.0066 (12)0.0041 (16)
O510.0329 (14)0.0320 (14)0.0572 (16)0.0155 (11)0.0068 (12)0.0046 (11)
O520.0225 (12)0.0318 (16)0.0467 (13)0.0022 (11)0.0065 (10)0.0076 (13)
C410.0309 (17)0.040 (3)0.0249 (17)0.008 (2)0.0033 (12)0.007 (4)
C420.0332 (19)0.018 (3)0.0294 (17)0.0074 (19)0.0004 (16)0.014 (3)
C430.041 (2)0.0250 (19)0.0293 (15)0.0011 (17)0.001 (3)0.007 (3)
C440.0278 (18)0.0314 (16)0.020 (3)0.0067 (13)0.006 (2)0.0069 (14)
C450.0345 (15)0.0286 (15)0.010 (5)0.0053 (12)0.0019 (13)0.0073 (14)
C460.049 (2)0.028 (2)0.012 (4)0.0117 (16)0.0078 (15)0.014 (3)
C470.041 (3)0.044 (2)0.037 (2)0.0088 (19)0.006 (4)0.001 (3)
C480.042 (2)0.039 (2)0.033 (8)0.0066 (16)0.0104 (19)0.001 (3)
N410.045 (2)0.023 (3)0.0361 (16)0.008 (3)0.0067 (14)0.007 (3)
N420.046 (2)0.020 (3)0.0451 (18)0.004 (3)0.0077 (17)0.001 (3)
O410.040 (2)0.032 (2)0.068 (3)0.0159 (17)0.0092 (19)0.0027 (18)
O420.0329 (16)0.043 (2)0.0580 (17)0.008 (2)0.0080 (13)0.005 (3)
C210.0235 (15)0.024 (3)0.0227 (14)0.0008 (16)0.0015 (10)0.004 (3)
C220.0252 (16)0.021 (2)0.0259 (14)0.0029 (16)0.0006 (13)0.009 (3)
C230.028 (2)0.0210 (18)0.027 (3)0.0003 (15)0.007 (3)0.011 (2)
C240.0227 (16)0.0218 (14)0.015 (3)0.0025 (11)0.0058 (19)0.0031 (13)
C250.0229 (13)0.0260 (14)0.009 (4)0.0042 (11)0.0039 (11)0.0054 (13)
C260.0284 (16)0.0168 (17)0.028 (2)0.0009 (13)0.0047 (15)0.004 (3)
C270.025 (2)0.0382 (18)0.0355 (17)0.0048 (15)0.004 (4)0.0011 (19)
C280.0288 (16)0.0345 (17)0.029 (6)0.0103 (13)0.0126 (15)0.0049 (18)
N210.0277 (16)0.026 (3)0.0355 (15)0.006 (2)0.0056 (12)0.014 (2)
N220.031 (2)0.031 (3)0.0393 (16)0.006 (2)0.0015 (15)0.007 (3)
O210.0293 (19)0.0361 (19)0.065 (2)0.0151 (15)0.0087 (16)0.0090 (16)
O220.0188 (13)0.042 (2)0.0518 (15)0.0082 (16)0.0063 (11)0.013 (2)
C21A0.0252 (16)0.021 (2)0.0259 (14)0.0029 (16)0.0006 (13)0.009 (3)
C22A0.0235 (15)0.024 (3)0.0227 (14)0.0008 (16)0.0015 (10)0.004 (3)
C23A0.0284 (16)0.0168 (17)0.028 (2)0.0009 (13)0.0047 (15)0.004 (3)
C24A0.0229 (13)0.0260 (14)0.009 (4)0.0042 (11)0.0039 (11)0.0054 (13)
C25A0.0227 (16)0.0218 (14)0.015 (3)0.0025 (11)0.0058 (19)0.0031 (13)
C26A0.028 (2)0.0210 (18)0.027 (3)0.0003 (15)0.007 (3)0.011 (2)
C27A0.0288 (16)0.0345 (17)0.029 (6)0.0103 (13)0.0126 (15)0.0049 (18)
C28A0.025 (2)0.0382 (18)0.0355 (17)0.0048 (15)0.004 (4)0.0011 (19)
N21A0.031 (2)0.031 (3)0.0393 (16)0.006 (2)0.0015 (15)0.007 (3)
N22A0.0277 (16)0.026 (3)0.0355 (15)0.006 (2)0.0056 (12)0.014 (2)
O21A0.038 (4)0.029 (3)0.075 (4)0.015 (2)0.007 (3)0.012 (3)
O22A0.0188 (13)0.042 (2)0.0518 (15)0.0082 (16)0.0063 (11)0.013 (2)
C41A0.0332 (19)0.018 (3)0.0294 (17)0.0074 (19)0.0004 (16)0.014 (3)
C42A0.0309 (17)0.040 (3)0.0249 (17)0.008 (2)0.0033 (12)0.007 (4)
C43A0.049 (2)0.028 (2)0.012 (4)0.0117 (16)0.0078 (15)0.014 (3)
C44A0.0345 (15)0.0286 (15)0.010 (5)0.0053 (12)0.0019 (13)0.0073 (14)
C45A0.0278 (18)0.0314 (16)0.020 (3)0.0067 (13)0.006 (2)0.0069 (14)
C46A0.041 (2)0.0250 (19)0.0293 (15)0.0011 (17)0.001 (3)0.007 (3)
C47A0.042 (2)0.039 (2)0.033 (8)0.0066 (16)0.0104 (19)0.001 (3)
C48A0.041 (3)0.044 (2)0.037 (2)0.0088 (19)0.006 (4)0.001 (3)
N41A0.046 (2)0.020 (3)0.0451 (18)0.004 (3)0.0077 (17)0.001 (3)
N42A0.045 (2)0.023 (3)0.0361 (16)0.008 (3)0.0067 (14)0.007 (3)
O41A0.040 (3)0.041 (3)0.079 (3)0.012 (2)0.012 (3)0.013 (2)
O42A0.0329 (16)0.043 (2)0.0580 (17)0.008 (2)0.0080 (13)0.005 (3)
C51A0.0255 (16)0.0204 (18)0.0240 (14)0.0001 (13)0.0024 (11)0.0031 (17)
C52A0.0234 (15)0.0252 (19)0.0215 (13)0.0016 (13)0.0014 (10)0.0009 (17)
C53A0.0287 (15)0.0205 (15)0.026 (2)0.0005 (12)0.0033 (12)0.0040 (15)
C54A0.0224 (13)0.0233 (14)0.021 (2)0.0041 (10)0.0029 (10)0.0014 (10)
C55A0.0255 (15)0.0203 (13)0.0206 (12)0.0020 (11)0.0018 (13)0.0012 (10)
C56A0.0311 (18)0.0182 (15)0.0296 (15)0.0007 (12)0.0024 (19)0.0022 (16)
C57A0.0312 (17)0.0292 (17)0.046 (4)0.0095 (13)0.0104 (17)0.001 (2)
C58A0.0258 (19)0.0321 (17)0.0377 (17)0.0045 (14)0.001 (3)0.0058 (17)
N51A0.0311 (17)0.0252 (19)0.0423 (15)0.0029 (15)0.0066 (12)0.0041 (16)
N52A0.0265 (14)0.0273 (17)0.0325 (13)0.0005 (15)0.0020 (11)0.0023 (16)
O51A0.024 (6)0.022 (5)0.077 (8)0.004 (4)0.021 (5)0.022 (5)
O52A0.0225 (12)0.0318 (16)0.0467 (13)0.0022 (11)0.0065 (10)0.0076 (13)
C31A0.0347 (18)0.019 (3)0.0269 (16)0.0032 (18)0.0024 (15)0.011 (4)
C32A0.0270 (16)0.020 (3)0.0255 (16)0.0046 (17)0.0019 (11)0.004 (4)
C33A0.0353 (18)0.0158 (18)0.026 (2)0.0055 (14)0.000 (2)0.002 (3)
C34A0.0263 (15)0.0329 (16)0.0213 (13)0.0080 (11)0.0023 (11)0.0021 (13)
C35A0.0291 (17)0.0297 (16)0.021 (3)0.0069 (12)0.0043 (19)0.0063 (14)
C36A0.035 (2)0.0246 (19)0.031 (3)0.0002 (16)0.004 (3)0.008 (3)
C37A0.0285 (19)0.041 (2)0.024 (5)0.0034 (15)0.003 (2)0.0069 (18)
C38A0.022 (2)0.045 (2)0.039 (4)0.0000 (17)0.006 (4)0.005 (2)
N31A0.030 (2)0.040 (3)0.0417 (16)0.007 (2)0.0051 (15)0.015 (3)
N32A0.0223 (16)0.037 (3)0.0321 (14)0.005 (2)0.0030 (12)0.003 (3)
O31A0.048 (4)0.029 (3)0.068 (4)0.013 (2)0.005 (3)0.014 (2)
O32A0.0235 (14)0.047 (3)0.0489 (15)0.0082 (18)0.0042 (11)0.012 (2)
C11A0.0267 (18)0.018 (3)0.0251 (15)0.001 (2)0.0036 (16)0.007 (5)
C12A0.0274 (16)0.027 (3)0.0214 (18)0.003 (2)0.0026 (12)0.004 (5)
C13A0.034 (2)0.0169 (19)0.026 (2)0.0013 (16)0.000 (3)0.001 (4)
C14A0.0252 (14)0.0238 (14)0.022 (2)0.0038 (11)0.0020 (13)0.0022 (15)
C15A0.0247 (18)0.0259 (15)0.0196 (19)0.0028 (12)0.002 (2)0.0038 (14)
C16A0.030 (3)0.0190 (19)0.0281 (17)0.0035 (18)0.003 (4)0.008 (4)
C17A0.026 (2)0.0384 (19)0.0474 (17)0.0097 (14)0.005 (4)0.005 (3)
C18A0.031 (3)0.0380 (19)0.0346 (16)0.0095 (18)0.003 (5)0.000 (3)
N11A0.033 (2)0.027 (3)0.0362 (16)0.002 (2)0.0045 (15)0.006 (3)
N12A0.0353 (19)0.023 (3)0.0325 (15)0.006 (3)0.0050 (13)0.001 (3)
O11A0.028 (3)0.036 (3)0.075 (3)0.012 (2)0.010 (2)0.013 (2)
O12A0.0265 (14)0.037 (2)0.0465 (15)0.0016 (18)0.0083 (12)0.006 (2)
Geometric parameters (Å, º) top
C11—N111.335 (3)C21A—N21A1.335 (3)
C11—C121.406 (2)C21A—C22A1.406 (2)
C11—C161.411 (3)C21A—C26A1.411 (3)
C12—N121.334 (3)C22A—N22A1.334 (3)
C12—C131.415 (3)C22A—C23A1.415 (3)
C13—C141.366 (3)C23A—C24A1.365 (3)
C13—H130.9500C23A—H23A0.9500
C14—C151.466 (2)C24A—C25A1.466 (2)
C14—C171.499 (4)C24A—C27A1.499 (4)
C15—C161.368 (3)C25A—C26A1.368 (3)
C15—C181.507 (3)C25A—C28A1.507 (3)
C16—H160.9500C26A—H26A0.9500
C17—H17A0.9800C27A—H27D0.9800
C17—H17B0.9800C27A—H27E0.9800
C17—H17C0.9800C27A—H27F0.9800
C18—H18A0.9800C28A—H28D0.9800
C18—H18B0.9800C28A—H28E0.9800
C18—H18C0.9800C28A—H28F0.9800
N11—O111.245 (2)N21A—O21A1.245 (2)
N11—O121.434 (2)N21A—O22A1.434 (2)
N12—O121.379 (2)N22A—O22A1.379 (2)
C31—N311.335 (3)C41A—N41A1.335 (3)
C31—C321.406 (2)C41A—C42A1.406 (2)
C31—C361.411 (3)C41A—C46A1.411 (3)
C32—N321.334 (3)C42A—N42A1.334 (3)
C32—C331.415 (3)C42A—C43A1.415 (3)
C33—C341.365 (3)C43A—C44A1.365 (3)
C33—H330.9500C43A—H43A0.9500
C34—C351.466 (2)C44A—C45A1.466 (2)
C34—C371.499 (4)C44A—C47A1.499 (4)
C35—C361.368 (3)C45A—C46A1.368 (3)
C35—C381.507 (3)C45A—C48A1.507 (3)
C36—H360.9500C46A—H46A0.9500
C37—H37A0.9800C47A—H47D0.9800
C37—H37B0.9800C47A—H47E0.9800
C37—H37C0.9800C47A—H47F0.9800
C38—H38A0.9800C48A—H48D0.9800
C38—H38B0.9800C48A—H48E0.9800
C38—H38C0.9800C48A—H48F0.9800
N31—O311.245 (2)N41A—O41A1.245 (2)
N31—O321.434 (2)N41A—O42A1.435 (2)
N32—O321.380 (2)N42A—O42A1.380 (2)
C51—N511.335 (3)C51A—N51A1.335 (3)
C51—C521.406 (2)C51A—C52A1.406 (2)
C51—C561.411 (3)C51A—C56A1.411 (3)
C52—N521.334 (3)C52A—N52A1.334 (3)
C52—C531.415 (3)C52A—C53A1.414 (3)
C53—C541.365 (3)C53A—C54A1.366 (3)
C53—H530.9500C53A—H53A0.9500
C54—C551.466 (2)C54A—C55A1.466 (2)
C54—C571.499 (3)C54A—C57A1.499 (4)
C55—C561.368 (3)C55A—C56A1.368 (3)
C55—C581.507 (3)C55A—C58A1.507 (3)
C56—H560.9500C56A—H56A0.9500
C57—H57A0.9800C57A—H57D0.9800
C57—H57B0.9800C57A—H57E0.9800
C57—H57C0.9800C57A—H57F0.9800
C58—H58A0.9800C58A—H58D0.9800
C58—H58B0.9800C58A—H58E0.9800
C58—H58C0.9800C58A—H58F0.9800
N51—O511.245 (2)N51A—O51A1.245 (2)
N51—O521.435 (2)N51A—O52A1.435 (2)
N52—O521.379 (2)N52A—O52A1.380 (2)
C41—N411.335 (3)C31A—N31A1.335 (3)
C41—C421.406 (2)C31A—C32A1.406 (2)
C41—C461.411 (3)C31A—C36A1.411 (3)
C42—N421.334 (3)C32A—N32A1.334 (3)
C42—C431.415 (3)C32A—C33A1.414 (3)
C43—C441.365 (3)C33A—C34A1.365 (3)
C43—H430.9500C33A—H33A0.9500
C44—C451.466 (2)C34A—C35A1.467 (2)
C44—C471.499 (4)C34A—C37A1.499 (4)
C45—C461.368 (3)C35A—C36A1.368 (3)
C45—C481.507 (3)C35A—C38A1.507 (3)
C46—H460.9500C36A—H36A0.9500
C47—H47A0.9800C37A—H37D0.9800
C47—H47B0.9800C37A—H37E0.9800
C47—H47C0.9800C37A—H37F0.9800
C48—H48A0.9800C38A—H38D0.9800
C48—H48B0.9800C38A—H38E0.9800
C48—H48C0.9800C38A—H38F0.9800
N41—O411.245 (2)N31A—O31A1.245 (2)
N41—O421.435 (2)N31A—O32A1.435 (2)
N42—O421.380 (2)N32A—O32A1.379 (2)
C21—N211.335 (3)C11A—N11A1.335 (3)
C21—C221.406 (2)C11A—C12A1.406 (2)
C21—C261.411 (3)C11A—C16A1.411 (3)
C22—N221.334 (3)C12A—N12A1.334 (3)
C22—C231.415 (3)C12A—C13A1.414 (3)
C23—C241.365 (3)C13A—C14A1.366 (3)
C23—H230.9500C13A—H13A0.9500
C24—C251.466 (2)C14A—C15A1.466 (2)
C24—C271.499 (4)C14A—C17A1.499 (4)
C25—C261.368 (3)C15A—C16A1.368 (3)
C25—C281.507 (3)C15A—C18A1.507 (3)
C26—H260.9500C16A—H16A0.9500
C27—H27A0.9800C17A—H17D0.9800
C27—H27B0.9800C17A—H17E0.9800
C27—H27C0.9800C17A—H17F0.9800
C28—H28A0.9800C18A—H18D0.9800
C28—H28B0.9800C18A—H18E0.9800
C28—H28C0.9800C18A—H18F0.9800
N21—O211.245 (2)N11A—O11A1.245 (2)
N21—O221.434 (2)N11A—O12A1.435 (2)
N22—O221.379 (2)N12A—O12A1.379 (2)
N11—C11—C12106.5 (2)N21A—C21A—C22A106.5 (2)
N11—C11—C16130.3 (2)N21A—C21A—C26A130.3 (2)
C12—C11—C16123.1 (2)C22A—C21A—C26A123.1 (2)
N12—C12—C11112.1 (2)N22A—C22A—C21A112.1 (2)
N12—C12—C13128.6 (2)N22A—C22A—C23A128.5 (2)
C11—C12—C13119.3 (2)C21A—C22A—C23A119.3 (2)
C14—C13—C12118.7 (2)C24A—C23A—C22A118.7 (2)
C14—C13—H13120.7C24A—C23A—H23A120.7
C12—C13—H13120.7C22A—C23A—H23A120.7
C13—C14—C15121.0 (3)C23A—C24A—C25A121.0 (3)
C13—C14—C17120.4 (2)C23A—C24A—C27A120.4 (2)
C15—C14—C17118.5 (3)C25A—C24A—C27A118.4 (3)
C16—C15—C14120.7 (3)C26A—C25A—C24A120.7 (3)
C16—C15—C18119.6 (2)C26A—C25A—C28A119.6 (2)
C14—C15—C18119.5 (3)C24A—C25A—C28A119.5 (3)
C15—C16—C11117.0 (2)C25A—C26A—C21A117.0 (2)
C15—C16—H16121.5C25A—C26A—H26A121.5
C11—C16—H16121.5C21A—C26A—H26A121.5
C14—C17—H17A109.5C24A—C27A—H27D109.5
C14—C17—H17B109.5C24A—C27A—H27E109.5
H17A—C17—H17B109.5H27D—C27A—H27E109.5
C14—C17—H17C109.5C24A—C27A—H27F109.5
H17A—C17—H17C109.5H27D—C27A—H27F109.5
H17B—C17—H17C109.5H27E—C27A—H27F109.5
C15—C18—H18A109.5C25A—C28A—H28D109.5
C15—C18—H18B109.5C25A—C28A—H28E109.5
H18A—C18—H18B109.5H28D—C28A—H28E109.5
C15—C18—H18C109.5C25A—C28A—H28F109.5
H18A—C18—H18C109.5H28D—C28A—H28F109.5
H18B—C18—H18C109.5H28E—C28A—H28F109.5
O11—N11—C11133.9 (2)O21A—N21A—C21A133.9 (2)
O11—N11—O12118.92 (18)O21A—N21A—O22A118.92 (18)
C11—N11—O12107.20 (17)C21A—N21A—O22A107.20 (17)
C12—N12—O12105.41 (17)C22A—N22A—O22A105.41 (17)
N12—O12—N11108.77 (15)N22A—O22A—N21A108.78 (15)
N31—C31—C32106.5 (2)N41A—C41A—C42A106.5 (2)
N31—C31—C36130.4 (2)N41A—C41A—C46A130.3 (2)
C32—C31—C36123.1 (2)C42A—C41A—C46A123.1 (2)
N32—C32—C31112.1 (2)N42A—C42A—C41A112.1 (2)
N32—C32—C33128.6 (2)N42A—C42A—C43A128.5 (2)
C31—C32—C33119.3 (2)C41A—C42A—C43A119.3 (2)
C34—C33—C32118.7 (2)C44A—C43A—C42A118.7 (2)
C34—C33—H33120.7C44A—C43A—H43A120.7
C32—C33—H33120.7C42A—C43A—H43A120.7
C33—C34—C35121.0 (3)C43A—C44A—C45A121.1 (3)
C33—C34—C37120.4 (2)C43A—C44A—C47A120.3 (2)
C35—C34—C37118.4 (3)C45A—C44A—C47A118.4 (3)
C36—C35—C34120.8 (3)C46A—C45A—C44A120.8 (3)
C36—C35—C38119.7 (2)C46A—C45A—C48A119.6 (2)
C34—C35—C38119.4 (3)C44A—C45A—C48A119.4 (3)
C35—C36—C31117.0 (2)C45A—C46A—C41A117.0 (2)
C35—C36—H36121.5C45A—C46A—H46A121.5
C31—C36—H36121.5C41A—C46A—H46A121.5
C34—C37—H37A109.5C44A—C47A—H47D109.5
C34—C37—H37B109.5C44A—C47A—H47E109.5
H37A—C37—H37B109.5H47D—C47A—H47E109.5
C34—C37—H37C109.5C44A—C47A—H47F109.5
H37A—C37—H37C109.5H47D—C47A—H47F109.5
H37B—C37—H37C109.5H47E—C47A—H47F109.5
C35—C38—H38A109.5C45A—C48A—H48D109.5
C35—C38—H38B109.5C45A—C48A—H48E109.5
H38A—C38—H38B109.5H48D—C48A—H48E109.5
C35—C38—H38C109.5C45A—C48A—H48F109.5
H38A—C38—H38C109.5H48D—C48A—H48F109.5
H38B—C38—H38C109.5H48E—C48A—H48F109.5
O31—N31—C31133.8 (2)O41A—N41A—C41A133.9 (2)
O31—N31—O32118.97 (18)O41A—N41A—O42A118.87 (18)
C31—N31—O32107.21 (17)C41A—N41A—O42A107.19 (17)
C32—N32—O32105.40 (17)C42A—N42A—O42A105.42 (17)
N32—O32—N31108.76 (15)N42A—O42A—N41A108.74 (15)
N51—C51—C52106.5 (2)N51A—C51A—C52A106.5 (2)
N51—C51—C56130.4 (2)N51A—C51A—C56A130.3 (2)
C52—C51—C56123.1 (2)C52A—C51A—C56A123.1 (2)
N52—C52—C51112.1 (2)N52A—C52A—C51A112.1 (2)
N52—C52—C53128.6 (2)N52A—C52A—C53A128.6 (2)
C51—C52—C53119.3 (2)C51A—C52A—C53A119.3 (2)
C54—C53—C52118.7 (2)C54A—C53A—C52A118.7 (2)
C54—C53—H53120.7C54A—C53A—H53A120.7
C52—C53—H53120.7C52A—C53A—H53A120.7
C53—C54—C55121.1 (3)C53A—C54A—C55A121.0 (3)
C53—C54—C57120.4 (2)C53A—C54A—C57A120.3 (2)
C55—C54—C57118.5 (3)C55A—C54A—C57A118.4 (3)
C56—C55—C54120.8 (2)C56A—C55A—C54A120.7 (3)
C56—C55—C58119.7 (2)C56A—C55A—C58A119.6 (2)
C54—C55—C58119.5 (3)C54A—C55A—C58A119.5 (3)
C55—C56—C51117.0 (2)C55A—C56A—C51A117.0 (2)
C55—C56—H56121.5C55A—C56A—H56A121.5
C51—C56—H56121.5C51A—C56A—H56A121.5
C54—C57—H57A109.5C54A—C57A—H57D109.5
C54—C57—H57B109.5C54A—C57A—H57E109.5
H57A—C57—H57B109.5H57D—C57A—H57E109.5
C54—C57—H57C109.5C54A—C57A—H57F109.5
H57A—C57—H57C109.5H57D—C57A—H57F109.5
H57B—C57—H57C109.5H57E—C57A—H57F109.5
C55—C58—H58A109.5C55A—C58A—H58D109.5
C55—C58—H58B109.5C55A—C58A—H58E109.5
H58A—C58—H58B109.5H58D—C58A—H58E109.5
C55—C58—H58C109.5C55A—C58A—H58F109.5
H58A—C58—H58C109.5H58D—C58A—H58F109.5
H58B—C58—H58C109.5H58E—C58A—H58F109.5
O51—N51—C51133.9 (2)O51A—N51A—C51A133.9 (2)
O51—N51—O52118.89 (17)O51A—N51A—O52A118.91 (18)
C51—N51—O52107.20 (16)C51A—N51A—O52A107.20 (17)
C52—N52—O52105.40 (17)C52A—N52A—O52A105.37 (18)
N52—O52—N51108.77 (14)N52A—O52A—N51A108.74 (15)
N41—C41—C42106.5 (2)N31A—C31A—C32A106.5 (2)
N41—C41—C46130.3 (2)N31A—C31A—C36A130.4 (2)
C42—C41—C46123.1 (2)C32A—C31A—C36A123.1 (2)
N42—C42—C41112.1 (2)N32A—C32A—C31A112.1 (2)
N42—C42—C43128.6 (2)N32A—C32A—C33A128.6 (2)
C41—C42—C43119.3 (2)C31A—C32A—C33A119.3 (2)
C44—C43—C42118.7 (2)C34A—C33A—C32A118.7 (2)
C44—C43—H43120.7C34A—C33A—H33A120.6
C42—C43—H43120.7C32A—C33A—H33A120.6
C43—C44—C45121.1 (3)C33A—C34A—C35A121.0 (3)
C43—C44—C47120.4 (2)C33A—C34A—C37A120.3 (2)
C45—C44—C47118.5 (3)C35A—C34A—C37A118.4 (3)
C46—C45—C44120.8 (3)C36A—C35A—C34A120.7 (3)
C46—C45—C48119.7 (2)C36A—C35A—C38A119.6 (2)
C44—C45—C48119.5 (3)C34A—C35A—C38A119.4 (3)
C45—C46—C41117.0 (2)C35A—C36A—C31A117.0 (2)
C45—C46—H46121.5C35A—C36A—H36A121.5
C41—C46—H46121.5C31A—C36A—H36A121.5
C44—C47—H47A109.5C34A—C37A—H37D109.5
C44—C47—H47B109.5C34A—C37A—H37E109.5
H47A—C47—H47B109.5H37D—C37A—H37E109.5
C44—C47—H47C109.5C34A—C37A—H37F109.5
H47A—C47—H47C109.5H37D—C37A—H37F109.5
H47B—C47—H47C109.5H37E—C37A—H37F109.5
C45—C48—H48A109.5C35A—C38A—H38D109.5
C45—C48—H48B109.5C35A—C38A—H38E109.5
H48A—C48—H48B109.5H38D—C38A—H38E109.5
C45—C48—H48C109.5C35A—C38A—H38F109.5
H48A—C48—H48C109.5H38D—C38A—H38F109.5
H48B—C48—H48C109.5H38E—C38A—H38F109.5
O41—N41—C41133.9 (2)O31A—N31A—C31A133.9 (2)
O41—N41—O42118.89 (18)O31A—N31A—O32A118.89 (18)
C41—N41—O42107.22 (17)C31A—N31A—O32A107.19 (17)
C42—N42—O42105.42 (17)C32A—N32A—O32A105.39 (17)
N42—O42—N41108.73 (15)N32A—O32A—N31A108.77 (15)
N21—C21—C22106.5 (2)N11A—C11A—C12A106.5 (2)
N21—C21—C26130.4 (2)N11A—C11A—C16A130.4 (2)
C22—C21—C26123.1 (2)C12A—C11A—C16A123.1 (2)
N22—C22—C21112.1 (2)N12A—C12A—C11A112.1 (2)
N22—C22—C23128.6 (2)N12A—C12A—C13A128.5 (2)
C21—C22—C23119.3 (2)C11A—C12A—C13A119.3 (2)
C24—C23—C22118.7 (2)C14A—C13A—C12A118.7 (2)
C24—C23—H23120.7C14A—C13A—H13A120.7
C22—C23—H23120.7C12A—C13A—H13A120.7
C23—C24—C25121.0 (3)C13A—C14A—C15A121.0 (3)
C23—C24—C27120.4 (2)C13A—C14A—C17A120.3 (2)
C25—C24—C27118.5 (3)C15A—C14A—C17A118.5 (3)
C26—C25—C24120.7 (3)C16A—C15A—C14A120.7 (3)
C26—C25—C28119.6 (2)C16A—C15A—C18A119.6 (2)
C24—C25—C28119.5 (3)C14A—C15A—C18A119.4 (3)
C25—C26—C21117.0 (2)C15A—C16A—C11A117.0 (2)
C25—C26—H26121.5C15A—C16A—H16A121.5
C21—C26—H26121.5C11A—C16A—H16A121.5
C24—C27—H27A109.5C14A—C17A—H17D109.5
C24—C27—H27B109.5C14A—C17A—H17E109.5
H27A—C27—H27B109.5H17D—C17A—H17E109.5
C24—C27—H27C109.5C14A—C17A—H17F109.5
H27A—C27—H27C109.5H17D—C17A—H17F109.5
H27B—C27—H27C109.5H17E—C17A—H17F109.5
C25—C28—H28A109.5C15A—C18A—H18D109.5
C25—C28—H28B109.5C15A—C18A—H18E109.5
H28A—C28—H28B109.5H18D—C18A—H18E109.5
C25—C28—H28C109.5C15A—C18A—H18F109.5
H28A—C28—H28C109.5H18D—C18A—H18F109.5
H28B—C28—H28C109.5H18E—C18A—H18F109.5
O21—N21—C21133.9 (2)O11A—N11A—C11A133.9 (2)
O21—N21—O22118.91 (18)O11A—N11A—O12A118.89 (18)
C21—N21—O22107.21 (17)C11A—N11A—O12A107.19 (17)
C22—N22—O22105.41 (17)C12A—N12A—O12A105.39 (17)
N22—O22—N21108.77 (15)N12A—O12A—N11A108.76 (15)
N11—C11—C12—N121.9 (14)N21A—C21A—C22A—N22A1.0 (16)
C16—C11—C12—N12179.5 (15)C26A—C21A—C22A—N22A175.5 (15)
N11—C11—C12—C13177.8 (16)N21A—C21A—C22A—C23A178.7 (13)
C16—C11—C12—C131 (2)C26A—C21A—C22A—C23A2 (2)
N12—C12—C13—C14178.9 (14)N22A—C22A—C23A—C24A175 (2)
C11—C12—C13—C141 (2)C21A—C22A—C23A—C24A2 (2)
C12—C13—C14—C153 (2)C22A—C23A—C24A—C25A3 (2)
C12—C13—C14—C17178.6 (18)C22A—C23A—C24A—C27A178.2 (18)
C13—C14—C15—C164 (2)C23A—C24A—C25A—C26A3.6 (18)
C17—C14—C15—C16179.6 (16)C27A—C24A—C25A—C26A178.9 (18)
C13—C14—C15—C18179.2 (16)C23A—C24A—C25A—C28A172 (2)
C17—C14—C15—C185.0 (19)C27A—C24A—C25A—C28A4 (2)
C14—C15—C16—C112 (2)C24A—C25A—C26A—C21A3.3 (18)
C18—C15—C16—C11177.6 (19)C28A—C25A—C26A—C21A172 (2)
N11—C11—C16—C15178.3 (16)N21A—C21A—C26A—C25A178.3 (14)
C12—C11—C16—C150 (2)C22A—C21A—C26A—C25A3 (2)
C12—C11—N11—O11179.8 (8)C22A—C21A—N21A—O21A179.0 (13)
C16—C11—N11—O111 (2)C26A—C21A—N21A—O21A5 (2)
C12—C11—N11—O121.6 (11)C22A—C21A—N21A—O22A0.8 (13)
C16—C11—N11—O12179.9 (16)C26A—C21A—N21A—O22A175.4 (15)
C11—C12—N12—O121.3 (12)C21A—C22A—N22A—O22A0.8 (15)
C13—C12—N12—O12178.4 (17)C23A—C22A—N22A—O22A178.1 (14)
C12—N12—O12—N110.2 (9)C22A—N22A—O22A—N21A0.2 (12)
O11—N11—O12—N12179.7 (5)O21A—N21A—O22A—N22A179.5 (8)
C11—N11—O12—N120.9 (9)C21A—N21A—O22A—N22A0.4 (11)
N31—C31—C32—N322.4 (11)N41A—C41A—C42A—N42A1.5 (15)
C36—C31—C32—N32179.6 (12)C46A—C41A—C42A—N42A178.0 (15)
N31—C31—C32—C33178.5 (12)N41A—C41A—C42A—C43A178.2 (12)
C36—C31—C32—C330.4 (18)C46A—C41A—C42A—C43A5 (2)
N32—C32—C33—C34178.1 (11)N42A—C42A—C43A—C44A179.2 (14)
C31—C32—C33—C342.9 (19)C41A—C42A—C43A—C44A3 (2)
C32—C33—C34—C353.7 (16)C42A—C43A—C44A—C45A0.2 (19)
C32—C33—C34—C37179.0 (13)C42A—C43A—C44A—C47A175.0 (17)
C33—C34—C35—C362.1 (12)C43A—C44A—C45A—C46A0.7 (19)
C37—C34—C35—C36177.4 (11)C47A—C44A—C45A—C46A176 (2)
C33—C34—C35—C38173.9 (13)C43A—C44A—C45A—C48A174.6 (18)
C37—C34—C35—C381.4 (11)C47A—C44A—C45A—C48A0.7 (18)
C34—C35—C36—C310.4 (14)C44A—C45A—C46A—C41A1 (2)
C38—C35—C36—C31176.4 (13)C48A—C45A—C46A—C41A176.6 (19)
N31—C31—C36—C35176.4 (11)N41A—C41A—C46A—C45A179.9 (15)
C32—C31—C36—C351.2 (18)C42A—C41A—C46A—C45A4 (2)
C32—C31—N31—O31178.5 (7)C42A—C41A—N41A—O41A179.3 (10)
C36—C31—N31—O310.6 (19)C46A—C41A—N41A—O41A5 (2)
C32—C31—N31—O321.8 (10)C42A—C41A—N41A—O42A2.1 (12)
C36—C31—N31—O32179.7 (13)C46A—C41A—N41A—O42A178.3 (15)
C31—C32—N32—O321.8 (10)C41A—C42A—N42A—O42A0.1 (13)
C33—C32—N32—O32179.2 (13)C43A—C42A—N42A—O42A176.5 (13)
C32—N32—O32—N310.6 (7)C42A—N42A—O42A—N41A1.2 (10)
O31—N31—O32—N32179.4 (5)O41A—N41A—O42A—N42A179.9 (6)
C31—N31—O32—N320.8 (8)C41A—N41A—O42A—N42A2.2 (10)
N51—C51—C52—N520.4 (4)N51A—C51A—C52A—N52A2.7 (17)
C56—C51—C52—N52179.4 (5)C56A—C51A—C52A—N52A179.9 (19)
N51—C51—C52—C53179.5 (4)N51A—C51A—C52A—C53A175 (2)
C56—C51—C52—C530.5 (6)C56A—C51A—C52A—C53A2 (3)
N52—C52—C53—C54179.5 (5)N52A—C52A—C53A—C54A180 (2)
C51—C52—C53—C540.4 (8)C51A—C52A—C53A—C54A3 (3)
C52—C53—C54—C550.1 (8)C52A—C53A—C54A—C55A0 (3)
C52—C53—C54—C57179.2 (6)C52A—C53A—C54A—C57A175 (3)
C53—C54—C55—C560.5 (8)C53A—C54A—C55A—C56A3 (3)
C57—C54—C55—C56179.7 (6)C57A—C54A—C55A—C56A178 (3)
C53—C54—C55—C58179.8 (7)C53A—C54A—C55A—C58A179 (2)
C57—C54—C55—C581.1 (7)C57A—C54A—C55A—C58A6 (3)
C54—C55—C56—C510.5 (8)C54A—C55A—C56A—C51A4 (3)
C58—C55—C56—C51179.7 (7)C58A—C55A—C56A—C51A179 (2)
N51—C51—C56—C55178.8 (5)N51A—C51A—C56A—C55A178 (2)
C52—C51—C56—C550.1 (7)C52A—C51A—C56A—C55A1 (3)
C52—C51—N51—O51179.9 (4)C52A—C51A—N51A—O51A177.5 (18)
C56—C51—N51—O511.2 (7)C56A—C51A—N51A—O51A0 (3)
C52—C51—N51—O520.2 (4)C52A—C51A—N51A—O52A0.6 (17)
C56—C51—N51—O52179.0 (5)C56A—C51A—N51A—O52A178 (2)
C51—C52—N52—O520.4 (4)C51A—C52A—N52A—O52A3.5 (14)
C53—C52—N52—O52179.4 (5)C53A—C52A—N52A—O52A174 (2)
C52—N52—O52—N510.3 (3)C52A—N52A—O52A—N51A3.0 (14)
O51—N51—O52—N52179.7 (3)O51A—N51A—O52A—N52A179.9 (14)
C51—N51—O52—N520.1 (3)C51A—N51A—O52A—N52A1.5 (16)
N41—C41—C42—N420.9 (12)N31A—C31A—C32A—N32A3.1 (18)
C46—C41—C42—N42177.8 (10)C36A—C31A—C32A—N32A178 (2)
N41—C41—C42—C43179.0 (12)N31A—C31A—C32A—C33A178.9 (18)
C46—C41—C42—C434.0 (17)C36A—C31A—C32A—C33A0 (3)
N42—C42—C43—C44178.9 (13)N32A—C32A—C33A—C34A177.4 (18)
C41—C42—C43—C443.3 (19)C31A—C32A—C33A—C34A0 (3)
C42—C43—C44—C451.3 (19)C32A—C33A—C34A—C35A1 (2)
C42—C43—C44—C47177.4 (16)C32A—C33A—C34A—C37A173 (2)
C43—C44—C45—C460.2 (16)C33A—C34A—C35A—C36A3.2 (17)
C47—C44—C45—C46176.0 (14)C37A—C34A—C35A—C36A171.1 (19)
C43—C44—C45—C48176.5 (16)C33A—C34A—C35A—C38A177.4 (18)
C47—C44—C45—C480.3 (15)C37A—C34A—C35A—C38A3.1 (17)
C44—C45—C46—C410.4 (15)C34A—C35A—C36A—C31A4 (2)
C48—C45—C46—C41175.9 (14)C38A—C35A—C36A—C31A178 (2)
N41—C41—C46—C45178.7 (12)N31A—C31A—C36A—C35A179.5 (17)
C42—C41—C46—C452.5 (16)C32A—C31A—C36A—C35A2 (3)
C42—C41—N41—O41178.4 (7)C32A—C31A—N31A—O31A176.1 (13)
C46—C41—N41—O414.9 (18)C36A—C31A—N31A—O31A2 (3)
C42—C41—N41—O420.1 (10)C32A—C31A—N31A—O32A2.3 (14)
C46—C41—N41—O42176.6 (11)C36A—C31A—N31A—O32A179 (2)
C41—C42—N42—O421.4 (10)C31A—C32A—N32A—O32A2.5 (17)
C43—C42—N42—O42179.4 (12)C33A—C32A—N32A—O32A180 (2)
C42—N42—O42—N411.4 (8)C32A—N32A—O32A—N31A1.1 (13)
O41—N41—O42—N42177.8 (5)O31A—N31A—O32A—N32A177.8 (8)
C41—N41—O42—N420.9 (8)C31A—N31A—O32A—N32A0.8 (12)
N21—C21—C22—N220.5 (9)N11A—C11A—C12A—N12A3.1 (17)
C26—C21—C22—N22179.5 (8)C16A—C11A—C12A—N12A177 (2)
N21—C21—C22—C23177.6 (8)N11A—C11A—C12A—C13A179.6 (18)
C26—C21—C22—C231.5 (12)C16A—C11A—C12A—C13A0 (3)
N22—C22—C23—C24179.0 (8)N12A—C12A—C13A—C14A178 (2)
C21—C22—C23—C241.3 (12)C11A—C12A—C13A—C14A2 (3)
C22—C23—C24—C252.7 (11)C12A—C13A—C14A—C15A4 (3)
C22—C23—C24—C27174.3 (12)C12A—C13A—C14A—C17A179 (2)
C23—C24—C25—C264.2 (11)C13A—C14A—C15A—C16A4 (3)
C27—C24—C25—C26172.8 (13)C17A—C14A—C15A—C16A179 (2)
C23—C24—C25—C28179.9 (10)C13A—C14A—C15A—C18A179 (2)
C27—C24—C25—C283.1 (12)C17A—C14A—C15A—C18A6 (2)
C24—C25—C26—C214.1 (13)C14A—C15A—C16A—C11A2 (3)
C28—C25—C26—C21180.0 (10)C18A—C15A—C16A—C11A177 (2)
N21—C21—C26—C25175.9 (11)N11A—C11A—C16A—C15A179.7 (18)
C22—C21—C26—C252.9 (13)C12A—C11A—C16A—C15A0 (3)
C22—C21—N21—O21179.0 (6)C12A—C11A—N11A—O11A177.7 (11)
C26—C21—N21—O212.1 (13)C16A—C11A—N11A—O11A2 (3)
C22—C21—N21—O220.4 (8)C12A—C11A—N11A—O12A1.8 (14)
C26—C21—N21—O22179.3 (8)C16A—C11A—N11A—O12A178 (2)
C21—C22—N22—O220.4 (8)C11A—C12A—N12A—O12A3.0 (15)
C23—C22—N22—O22177.5 (8)C13A—C12A—N12A—O12A180.0 (19)
C22—N22—O22—N210.1 (6)C12A—N12A—O12A—N11A1.8 (11)
O21—N21—O22—N22179.0 (4)O11A—N11A—O12A—N12A179.5 (6)
C21—N21—O22—N220.2 (7)C11A—N11A—O12A—N12A0.0 (11)
(Me2PA) 4,5-dimethylphthalic anhydride top
Crystal data top
C10H8O3F(000) = 736
Mr = 176.16Dx = 1.448 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3420 reflections
a = 11.744 (4) Åθ = 2.8–27.5°
b = 7.601 (3) ŵ = 0.11 mm1
c = 18.102 (6) ÅT = 173 K
V = 1615.9 (10) Å3Prism, colorless
Z = 80.50 × 0.35 × 0.25 mm
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
1857 independent reflections
Radiation source: fine-focus sealed tube1772 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω scansθmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan
SADABS; Sheldrick, 2008; Blessing, 1995
h = 1515
Tmin = 0.95, Tmax = 0.97k = 99
17411 measured reflectionsl = 2323
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: calc
R[F2 > 2σ(F2)] = 0.033H-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 reflectionsΔρmax = 0.33 e Å3
121 parametersΔρmin = 0.14 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.084 (4)
Crystal data top
C10H8O3V = 1615.9 (10) Å3
Mr = 176.16Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 11.744 (4) ŵ = 0.11 mm1
b = 7.601 (3) ÅT = 173 K
c = 18.102 (6) Å0.50 × 0.35 × 0.25 mm
Data collection top
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 = 0.97Rint = 0.027
17411 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.099H-atom parameters constrained
S = 1.06Δρmax = 0.33 e Å3
1857 reflectionsΔρmin = 0.14 e Å3
121 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.05887 (8)0.21317 (12)0.48258 (5)0.0228 (2)
C20.15461 (8)0.10774 (13)0.48559 (5)0.0232 (2)
C30.20234 (8)0.05807 (14)0.55217 (5)0.0256 (2)
H30.26890.01290.55350.031*
C40.15040 (8)0.11466 (13)0.61746 (5)0.0248 (2)
C50.05135 (9)0.22036 (13)0.61446 (5)0.0247 (2)
C60.00614 (8)0.27159 (13)0.54630 (5)0.0248 (2)
H60.05930.34480.54390.030*
C70.02919 (8)0.23818 (13)0.40411 (5)0.0252 (2)
C80.18618 (9)0.06185 (13)0.40921 (5)0.0261 (2)
C90.19891 (9)0.05791 (16)0.69046 (6)0.0330 (3)
H9A0.14850.02960.71310.049*
H9B0.20540.16020.72320.049*
H9C0.27440.00620.68280.049*
C100.00697 (10)0.27670 (16)0.68445 (6)0.0328 (3)
H10A0.07510.34520.67220.049*
H10B0.04510.34920.71380.049*
H10C0.02900.17250.71290.049*
O110.04487 (7)0.31905 (11)0.37500 (4)0.0350 (2)
O120.26160 (7)0.02644 (12)0.38547 (4)0.0376 (2)
O130.10748 (6)0.14088 (9)0.36216 (4)0.0276 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0253 (4)0.0229 (5)0.0203 (5)0.0029 (4)0.0010 (3)0.0011 (3)
C20.0250 (5)0.0237 (5)0.0210 (5)0.0023 (4)0.0025 (3)0.0004 (3)
C30.0258 (5)0.0267 (5)0.0242 (5)0.0004 (4)0.0002 (4)0.0023 (4)
C40.0273 (5)0.0258 (5)0.0214 (5)0.0050 (4)0.0009 (4)0.0030 (3)
C50.0276 (5)0.0258 (5)0.0206 (5)0.0045 (4)0.0023 (4)0.0009 (3)
C60.0258 (5)0.0256 (5)0.0231 (5)0.0008 (4)0.0009 (4)0.0009 (3)
C70.0286 (5)0.0255 (5)0.0215 (5)0.0030 (4)0.0001 (4)0.0006 (4)
C80.0294 (5)0.0270 (5)0.0219 (5)0.0021 (4)0.0016 (4)0.0003 (4)
C90.0364 (6)0.0406 (6)0.0220 (5)0.0008 (5)0.0023 (4)0.0068 (4)
C100.0371 (5)0.0390 (6)0.0222 (5)0.0003 (5)0.0057 (4)0.0028 (4)
O110.0380 (4)0.0399 (5)0.0271 (4)0.0065 (3)0.0063 (3)0.0027 (3)
O120.0393 (5)0.0434 (5)0.0300 (4)0.0101 (4)0.0076 (3)0.0040 (3)
O130.0329 (4)0.0300 (4)0.0198 (4)0.0004 (3)0.0001 (3)0.0016 (3)
Geometric parameters (Å, º) top
C1—C21.3819 (14)C6—H60.9500
C1—C61.3825 (13)C7—O111.1883 (13)
C1—C71.4748 (14)C7—O131.4032 (12)
C2—C31.3818 (14)C8—O121.1915 (13)
C2—C81.4734 (14)C8—O131.3929 (13)
C3—C41.3980 (14)C9—H9A0.9800
C3—H30.9500C9—H9B0.9800
C4—C51.4147 (15)C9—H9C0.9800
C4—C91.5023 (13)C10—H10A0.9800
C5—C61.3984 (14)C10—H10B0.9800
C5—C101.5027 (14)C10—H10C0.9800
C2—C1—C6121.19 (9)O11—C7—C1131.82 (9)
C2—C1—C7107.76 (8)O13—C7—C1107.36 (8)
C6—C1—C7131.02 (9)O12—C8—O13121.05 (9)
C3—C2—C1121.53 (9)O12—C8—C2131.21 (10)
C3—C2—C8130.68 (9)O13—C8—C2107.74 (8)
C1—C2—C8107.76 (8)C4—C9—H9A109.5
C2—C3—C4118.45 (10)C4—C9—H9B109.5
C2—C3—H3120.8H9A—C9—H9B109.5
C4—C3—H3120.8C4—C9—H9C109.5
C3—C4—C5120.06 (9)H9A—C9—H9C109.5
C3—C4—C9119.33 (10)H9B—C9—H9C109.5
C5—C4—C9120.58 (9)C5—C10—H10A109.5
C6—C5—C4120.29 (9)C5—C10—H10B109.5
C6—C5—C10119.44 (9)H10A—C10—H10B109.5
C4—C5—C10120.28 (9)C5—C10—H10C109.5
C1—C6—C5118.46 (9)H10A—C10—H10C109.5
C1—C6—H6120.8H10B—C10—H10C109.5
C5—C6—H6120.8C8—O13—C7109.34 (8)
O11—C7—O13120.82 (9)
C6—C1—C2—C30.76 (15)C4—C5—C6—C11.50 (15)
C7—C1—C2—C3178.93 (9)C10—C5—C6—C1177.77 (9)
C6—C1—C2—C8177.29 (9)C2—C1—C7—O11179.21 (11)
C7—C1—C2—C80.88 (11)C6—C1—C7—O112.87 (19)
C1—C2—C3—C41.03 (15)C2—C1—C7—O131.77 (10)
C8—C2—C3—C4176.52 (9)C6—C1—C7—O13176.15 (10)
C2—C3—C4—C50.04 (15)C3—C2—C8—O121.61 (19)
C2—C3—C4—C9178.26 (9)C1—C2—C8—O12179.42 (11)
C3—C4—C5—C61.23 (15)C3—C2—C8—O13177.49 (10)
C9—C4—C5—C6179.51 (9)C1—C2—C8—O130.33 (11)
C3—C4—C5—C10178.03 (9)O12—C8—O13—C7179.33 (10)
C9—C4—C5—C100.25 (15)C2—C8—O13—C71.46 (10)
C2—C1—C6—C50.52 (15)O11—C7—O13—C8178.86 (10)
C7—C1—C6—C5177.16 (9)C1—C7—O13—C81.99 (10)

Experimental details

(Z2)(Z4)(Z6)(Z10)
Crystal data
Chemical formulaC8H8N2O2C8H8N2O2C8H8N2O2C8H8N2O2
Mr164.16164.16164.16164.16
Crystal system, space groupTriclinic, P1Triclinic, P1Triclinic, P1Triclinic, P1
Temperature (K)173173173173
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)
V3)382.9 (2)769.99 (16)1154.6 (2)1923.9 (7)
Z24610
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.110.110.110.11
Crystal size (mm)0.50 × 0.13 × 0.060.35 × 0.30 × 0.250.35 × 0.25 × 0.200.40 × 0.35 × 0.20
Data collection
DiffractometerBruker 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 correctionMulti-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, Tmax0.94, 0.990.96, 0.970.96, 0.980.96, 0.98
No. of measured, independent and
observed [I > 2σ(I)] reflections
4353, 1713, 1379 8977, 3498, 2286 13249, 5157, 3457 22419, 8722, 3791
Rint0.0310.0240.0200.054
(sin θ/λ)max1)0.6500.6500.6500.651
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 reflections1713349851578722
No. of parameters153304454756
No. of restraints321924801440
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.220.19, 0.150.40, 0.231.18, 0.39


(Me2PA)
Crystal data
Chemical formulaC10H8O3
Mr176.16
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)173
a, b, c (Å)11.744 (4), 7.601 (3), 18.102 (6)
α, β, γ (°)90, 90, 90
V3)1615.9 (10)
Z8
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.50 × 0.35 × 0.25
Data collection
DiffractometerBruker SMART 1K CCD area-detector
diffractometer
Absorption correctionMulti-scan
SADABS; Sheldrick, 2008; Blessing, 1995
Tmin, Tmax0.95, 0.97
No. of measured, independent and
observed [I > 2σ(I)] reflections
17411, 1857, 1772
Rint0.027
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.099, 1.06
No. of reflections1857
No. of parameters121
No. of restraints0
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.14

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SAINT, SHELXTL (Sheldrick, 2008), SHELXTL.

 

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