Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113025869/cu3041sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113025869/cu3041C14H13N3O4sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113025869/cu3041C22H22N4O4sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113025869/cu3041C15H13N3O2sup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113025869/cu3041C15H16N2O4Ssup5.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113025869/cu3041C14H13N3O4sup6.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113025869/cu3041C22H22N4O4sup7.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113025869/cu3041C15H13N3O2sup8.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113025869/cu3041C15H16N2O4Ssup9.cml |
CCDC references: 961994; 961995; 961996; 961997
For all compounds, data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: APEX2 (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalMaker (Palmer, 2013); software used to prepare material for publication: APEX2 (Bruker, 2005).
C14H13N3O4 | Z = 2 |
Mr = 287.27 | F(000) = 300 |
Triclinic, P1 | Dx = 1.459 Mg m−3 |
Hall symbol: -P 1 | Melting point: 425 K |
a = 7.235 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.282 (2) Å | Cell parameters from 11611 reflections |
c = 13.512 (4) Å | θ = 3.0–32.1° |
α = 88.714 (5)° | µ = 0.11 mm−1 |
β = 85.131 (5)° | T = 100 K |
γ = 67.239 (5)° | Plate, orange |
V = 654.0 (4) Å3 | 0.20 × 0.10 × 0.02 mm |
Bruker APEX DUO CCD area-detector diffractometer | 3158 independent reflections |
Radiation source: sealed tube | 2288 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ω scans | θmax = 28.0°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.978, Tmax = 0.998 | k = −9→9 |
9039 measured reflections | l = −17→17 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.104 | All H-atom parameters refined |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0523P)2 + 0.1059P] where P = (Fo2 + 2Fc2)/3 |
3158 reflections | (Δ/σ)max < 0.001 |
242 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O21 | 0.47421 (16) | 0.19492 (14) | 0.46231 (7) | 0.0226 (3) | |
O22 | 0.30058 (15) | 0.48827 (14) | 0.40811 (8) | 0.0218 (2) | |
O41 | 0.35861 (18) | 0.39571 (17) | −0.04202 (8) | 0.0288 (3) | |
O42 | 0.17704 (17) | 0.61028 (16) | 0.07262 (8) | 0.0304 (3) | |
N1 | 0.69604 (18) | −0.09321 (17) | 0.33654 (9) | 0.0162 (3) | |
H1 | 0.654 (3) | −0.062 (3) | 0.3982 (14) | 0.032 (5)* | |
N2 | 0.41095 (17) | 0.31155 (16) | 0.39279 (8) | 0.0150 (3) | |
N4 | 0.31213 (19) | 0.44961 (18) | 0.04614 (9) | 0.0212 (3) | |
C1 | 0.61056 (19) | 0.04072 (19) | 0.26771 (10) | 0.0137 (3) | |
C2 | 0.46755 (19) | 0.23875 (19) | 0.29173 (10) | 0.0132 (3) | |
C3 | 0.3740 (2) | 0.3712 (2) | 0.21903 (10) | 0.0141 (3) | |
H3 | 0.280 (2) | 0.497 (2) | 0.2391 (11) | 0.018 (4)* | |
C4 | 0.4213 (2) | 0.3149 (2) | 0.12088 (10) | 0.0166 (3) | |
C5 | 0.5681 (2) | 0.1266 (2) | 0.09314 (11) | 0.0179 (3) | |
H5 | 0.599 (2) | 0.092 (2) | 0.0257 (13) | 0.021 (4)* | |
C6 | 0.6582 (2) | −0.0059 (2) | 0.16413 (11) | 0.0167 (3) | |
H6 | 0.756 (3) | −0.133 (3) | 0.1449 (13) | 0.027 (4)* | |
C7 | 0.8410 (2) | −0.2971 (2) | 0.31717 (12) | 0.0178 (3) | |
H7A | 0.932 (2) | −0.299 (2) | 0.2580 (12) | 0.018 (4)* | |
H7B | 0.920 (2) | −0.336 (2) | 0.3754 (12) | 0.021 (4)* | |
C8 | 0.7394 (2) | −0.4436 (2) | 0.30299 (12) | 0.0169 (3) | |
H8B | 0.641 (2) | −0.429 (2) | 0.3592 (12) | 0.015 (4)* | |
H8A | 0.662 (2) | −0.411 (2) | 0.2453 (12) | 0.014 (4)* | |
C9 | 0.8931 (2) | −0.65607 (19) | 0.29443 (10) | 0.0151 (3) | |
C10 | 0.9689 (2) | −0.7611 (2) | 0.37972 (11) | 0.0185 (3) | |
H10 | 0.917 (2) | −0.699 (2) | 0.4453 (13) | 0.025 (4)* | |
C11 | 1.1134 (2) | −0.9552 (2) | 0.37235 (13) | 0.0221 (3) | |
H11 | 1.161 (3) | −1.025 (3) | 0.4326 (14) | 0.034 (5)* | |
C12 | 1.1825 (2) | −1.0461 (2) | 0.27972 (13) | 0.0237 (3) | |
H12 | 1.277 (3) | −1.178 (3) | 0.2770 (12) | 0.026 (4)* | |
C13 | 1.1069 (2) | −0.9442 (2) | 0.19510 (12) | 0.0225 (3) | |
H13 | 1.155 (3) | −1.014 (3) | 0.1310 (14) | 0.031 (5)* | |
C14 | 0.9635 (2) | −0.7496 (2) | 0.20191 (11) | 0.0182 (3) | |
H14 | 0.914 (2) | −0.682 (2) | 0.1425 (13) | 0.025 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O21 | 0.0317 (6) | 0.0159 (5) | 0.0157 (5) | −0.0043 (4) | −0.0026 (4) | 0.0024 (4) |
O22 | 0.0234 (6) | 0.0124 (5) | 0.0224 (5) | 0.0007 (4) | 0.0012 (4) | −0.0048 (4) |
O41 | 0.0441 (7) | 0.0303 (6) | 0.0144 (5) | −0.0161 (5) | −0.0063 (5) | 0.0025 (4) |
O42 | 0.0346 (7) | 0.0196 (6) | 0.0282 (6) | −0.0002 (5) | −0.0069 (5) | 0.0043 (5) |
N1 | 0.0168 (6) | 0.0101 (6) | 0.0190 (6) | −0.0023 (5) | −0.0014 (5) | −0.0008 (5) |
N2 | 0.0154 (6) | 0.0131 (6) | 0.0154 (6) | −0.0046 (5) | −0.0004 (5) | −0.0009 (5) |
N4 | 0.0282 (7) | 0.0195 (7) | 0.0180 (6) | −0.0109 (6) | −0.0052 (5) | 0.0036 (5) |
C1 | 0.0113 (6) | 0.0122 (6) | 0.0191 (7) | −0.0061 (5) | −0.0008 (5) | −0.0012 (5) |
C2 | 0.0140 (7) | 0.0112 (6) | 0.0143 (7) | −0.0050 (5) | 0.0010 (5) | −0.0027 (5) |
C3 | 0.0129 (6) | 0.0108 (6) | 0.0186 (7) | −0.0047 (5) | 0.0002 (5) | −0.0014 (5) |
C4 | 0.0182 (7) | 0.0151 (7) | 0.0180 (7) | −0.0080 (6) | −0.0021 (6) | 0.0020 (5) |
C5 | 0.0217 (7) | 0.0183 (7) | 0.0155 (7) | −0.0104 (6) | 0.0029 (6) | −0.0045 (6) |
C6 | 0.0152 (7) | 0.0127 (7) | 0.0214 (7) | −0.0049 (6) | 0.0028 (6) | −0.0047 (5) |
C7 | 0.0135 (7) | 0.0108 (7) | 0.0263 (8) | −0.0011 (5) | −0.0042 (6) | −0.0003 (6) |
C8 | 0.0130 (7) | 0.0121 (7) | 0.0235 (8) | −0.0024 (5) | −0.0018 (6) | −0.0014 (5) |
C9 | 0.0119 (6) | 0.0126 (7) | 0.0214 (7) | −0.0055 (5) | −0.0002 (5) | −0.0017 (5) |
C10 | 0.0188 (7) | 0.0167 (7) | 0.0203 (8) | −0.0077 (6) | −0.0003 (6) | 0.0010 (6) |
C11 | 0.0190 (8) | 0.0156 (7) | 0.0326 (9) | −0.0073 (6) | −0.0052 (6) | 0.0062 (6) |
C12 | 0.0138 (7) | 0.0110 (7) | 0.0451 (10) | −0.0040 (6) | 0.0009 (6) | −0.0032 (6) |
C13 | 0.0172 (7) | 0.0196 (7) | 0.0311 (9) | −0.0088 (6) | 0.0068 (6) | −0.0120 (6) |
C14 | 0.0177 (7) | 0.0188 (7) | 0.0200 (7) | −0.0091 (6) | −0.0007 (6) | −0.0021 (6) |
O21—N2 | 1.2448 (15) | C7—C8 | 1.534 (2) |
O22—N2 | 1.2350 (14) | C7—H7A | 0.989 (16) |
O41—N4 | 1.2398 (16) | C7—H7B | 0.984 (16) |
O42—N4 | 1.2356 (16) | C8—C9 | 1.5161 (19) |
N1—C1 | 1.3374 (18) | C8—H8B | 0.974 (16) |
N1—C7 | 1.4622 (17) | C8—H8A | 0.967 (16) |
N1—H1 | 0.867 (19) | C9—C14 | 1.396 (2) |
N2—C2 | 1.4433 (17) | C9—C10 | 1.399 (2) |
N4—C4 | 1.4482 (18) | C10—C11 | 1.395 (2) |
C1—C6 | 1.429 (2) | C10—H10 | 0.980 (17) |
C1—C2 | 1.4369 (18) | C11—C12 | 1.389 (2) |
C2—C3 | 1.3850 (19) | C11—H11 | 0.966 (19) |
C3—C4 | 1.372 (2) | C12—C13 | 1.382 (2) |
C3—H3 | 0.932 (16) | C12—H12 | 0.938 (17) |
C4—C5 | 1.406 (2) | C13—C14 | 1.395 (2) |
C5—C6 | 1.362 (2) | C13—H13 | 0.979 (18) |
C5—H5 | 0.937 (17) | C14—H14 | 0.955 (17) |
C6—H6 | 0.948 (17) | ||
C1—N1—C7 | 125.87 (13) | C8—C7—H7A | 110.3 (9) |
C1—N1—H1 | 117.6 (12) | N1—C7—H7B | 106.3 (9) |
C7—N1—H1 | 116.2 (12) | C8—C7—H7B | 109.5 (9) |
O22—N2—O21 | 121.63 (11) | H7A—C7—H7B | 108.7 (13) |
O22—N2—C2 | 119.07 (11) | C9—C8—C7 | 111.05 (11) |
O21—N2—C2 | 119.30 (11) | C9—C8—H8B | 110.6 (9) |
O42—N4—O41 | 123.20 (12) | C7—C8—H8B | 108.5 (9) |
O42—N4—C4 | 119.13 (12) | C9—C8—H8A | 110.1 (9) |
O41—N4—C4 | 117.66 (12) | C7—C8—H8A | 111.3 (9) |
N1—C1—C6 | 121.24 (12) | H8B—C8—H8A | 105.1 (12) |
N1—C1—C2 | 123.14 (12) | C14—C9—C10 | 118.80 (13) |
C6—C1—C2 | 115.62 (12) | C14—C9—C8 | 120.97 (13) |
C3—C2—C1 | 121.89 (12) | C10—C9—C8 | 120.23 (13) |
C3—C2—N2 | 115.84 (11) | C11—C10—C9 | 120.58 (14) |
C1—C2—N2 | 122.28 (12) | C11—C10—H10 | 119.7 (10) |
C4—C3—C2 | 119.61 (12) | C9—C10—H10 | 119.7 (10) |
C4—C3—H3 | 122.3 (9) | C12—C11—C10 | 119.96 (15) |
C2—C3—H3 | 118.1 (9) | C12—C11—H11 | 121.3 (11) |
C3—C4—C5 | 120.74 (13) | C10—C11—H11 | 118.7 (11) |
C3—C4—N4 | 118.95 (12) | C13—C12—C11 | 119.87 (14) |
C5—C4—N4 | 120.27 (12) | C13—C12—H12 | 121.9 (11) |
C6—C5—C4 | 120.01 (13) | C11—C12—H12 | 118.2 (11) |
C6—C5—H5 | 120.6 (10) | C12—C13—C14 | 120.46 (14) |
C4—C5—H5 | 119.3 (10) | C12—C13—H13 | 118.1 (10) |
C5—C6—C1 | 122.00 (13) | C14—C13—H13 | 121.4 (10) |
C5—C6—H6 | 119.6 (10) | C13—C14—C9 | 120.33 (14) |
C1—C6—H6 | 118.4 (10) | C13—C14—H14 | 119.1 (10) |
N1—C7—C8 | 112.67 (12) | C9—C14—H14 | 120.6 (10) |
N1—C7—H7A | 109.2 (9) | ||
C7—N1—C1—C6 | −0.9 (2) | C3—C4—C5—C6 | 3.2 (2) |
C7—N1—C1—C2 | 179.47 (12) | N4—C4—C5—C6 | −174.48 (13) |
N1—C1—C2—C3 | −176.80 (13) | C4—C5—C6—C1 | −0.9 (2) |
C6—C1—C2—C3 | 3.52 (19) | N1—C1—C6—C5 | 177.98 (13) |
N1—C1—C2—N2 | 2.6 (2) | C2—C1—C6—C5 | −2.33 (19) |
C6—C1—C2—N2 | −177.05 (12) | C1—N1—C7—C8 | −85.52 (17) |
O22—N2—C2—C3 | −6.70 (18) | N1—C7—C8—C9 | −173.75 (12) |
O21—N2—C2—C3 | 173.22 (12) | C7—C8—C9—C14 | −99.44 (16) |
O22—N2—C2—C1 | 173.85 (12) | C7—C8—C9—C10 | 79.65 (16) |
O21—N2—C2—C1 | −6.24 (18) | C14—C9—C10—C11 | 0.4 (2) |
C1—C2—C3—C4 | −1.4 (2) | C8—C9—C10—C11 | −178.69 (13) |
N2—C2—C3—C4 | 179.12 (12) | C9—C10—C11—C12 | −0.2 (2) |
C2—C3—C4—C5 | −2.0 (2) | C10—C11—C12—C13 | −0.4 (2) |
C2—C3—C4—N4 | 175.69 (12) | C11—C12—C13—C14 | 0.9 (2) |
O42—N4—C4—C3 | −1.2 (2) | C12—C13—C14—C9 | −0.7 (2) |
O41—N4—C4—C3 | 179.53 (13) | C10—C9—C14—C13 | 0.0 (2) |
O42—N4—C4—C5 | 176.52 (13) | C8—C9—C14—C13 | 179.15 (13) |
O41—N4—C4—C5 | −2.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O21 | 0.867 (19) | 1.983 (19) | 2.6377 (16) | 131.5 (16) |
N1—H1···O21i | 0.867 (19) | 2.381 (19) | 3.0823 (18) | 138.3 (16) |
Symmetry code: (i) −x+1, −y, −z+1. |
C22H22N4O4 | Z = 2 |
Mr = 406.44 | F(000) = 428 |
Triclinic, P1 | Dx = 1.378 Mg m−3 |
Hall symbol: -P 1 | Melting point: 408 K |
a = 8.1121 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.1819 (8) Å | Cell parameters from 17364 reflections |
c = 13.1018 (11) Å | θ = 2.5–32.7° |
α = 93.466 (1)° | µ = 0.10 mm−1 |
β = 106.595 (1)° | T = 100 K |
γ = 106.932 (1)° | Parallelpiped, orange |
V = 979.88 (14) Å3 | 0.20 × 0.10 × 0.05 mm |
Bruker APEX DUO CCD area-detector diffractometer | 6868 independent reflections |
Radiation source: sealed tube | 5289 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
ω scans | θmax = 33.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.981, Tmax = 0.995 | k = −15→15 |
17364 measured reflections | l = −19→19 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.121 | All H-atom parameters refined |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0693P)2 + 0.148P] where P = (Fo2 + 2Fc2)/3 |
6868 reflections | (Δ/σ)max = 0.001 |
359 parameters | Δρmax = 0.57 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O21 | 0.23044 (11) | 0.49365 (8) | −0.03714 (6) | 0.02254 (17) | |
O22 | 0.20579 (10) | 0.44974 (8) | 0.11874 (6) | 0.02074 (16) | |
O41 | 0.80203 (11) | 0.91022 (8) | 0.45448 (6) | 0.02101 (16) | |
O42 | 0.57135 (10) | 0.72779 (8) | 0.43962 (6) | 0.02098 (16) | |
N1 | 0.51043 (11) | 0.69381 (9) | −0.05088 (6) | 0.01446 (15) | |
H1 | 0.410 (2) | 0.6227 (15) | −0.0847 (12) | 0.029 (4)* | |
N2 | 0.28480 (11) | 0.52119 (8) | 0.06328 (7) | 0.01512 (16) | |
N4 | 0.67006 (11) | 0.80913 (9) | 0.39872 (6) | 0.01476 (16) | |
N5 | 0.86876 (11) | 1.00007 (8) | 0.28122 (7) | 0.01354 (15) | |
H5 | 0.905 (2) | 1.0156 (17) | 0.3538 (14) | 0.039 (4)* | |
C1 | 0.54668 (12) | 0.72552 (9) | 0.05682 (7) | 0.01225 (16) | |
C2 | 0.44289 (12) | 0.63957 (9) | 0.11528 (7) | 0.01285 (16) | |
C3 | 0.48939 (12) | 0.67177 (9) | 0.22604 (7) | 0.01303 (16) | |
H3 | 0.4177 (19) | 0.6132 (15) | 0.2631 (11) | 0.026 (4)* | |
C4 | 0.63377 (12) | 0.78684 (9) | 0.28394 (7) | 0.01247 (16) | |
C5 | 0.73706 (12) | 0.88063 (9) | 0.22938 (7) | 0.01228 (16) | |
C6 | 0.69047 (12) | 0.84309 (9) | 0.11745 (7) | 0.01281 (16) | |
H6 | 0.7613 (18) | 0.9005 (14) | 0.0809 (11) | 0.020 (3)* | |
C7 | 0.60110 (13) | 0.78288 (10) | −0.11463 (8) | 0.01417 (17) | |
H7A | 0.5825 (17) | 0.7264 (13) | −0.1818 (10) | 0.015 (3)* | |
H7B | 0.7300 (18) | 0.8193 (13) | −0.0770 (10) | 0.017 (3)* | |
C8 | 0.52363 (14) | 0.90188 (11) | −0.14096 (8) | 0.01701 (18) | |
H8B | 0.5228 (19) | 0.9459 (15) | −0.0728 (12) | 0.025 (4)* | |
H8A | 0.396 (2) | 0.8610 (15) | −0.1902 (12) | 0.027 (4)* | |
C9 | 0.63215 (12) | 1.00500 (10) | −0.19438 (7) | 0.01360 (17) | |
C10 | 0.59759 (13) | 0.98259 (10) | −0.30591 (8) | 0.01541 (17) | |
H10 | 0.501 (2) | 0.9015 (16) | −0.3492 (12) | 0.029 (4)* | |
C11 | 0.70127 (14) | 1.07599 (11) | −0.35487 (8) | 0.01895 (19) | |
H11 | 0.677 (2) | 1.0608 (16) | −0.4351 (13) | 0.032 (4)* | |
C12 | 0.84093 (14) | 1.19286 (11) | −0.29268 (9) | 0.0209 (2) | |
H12 | 0.915 (2) | 1.2594 (18) | −0.3244 (14) | 0.042 (4)* | |
C13 | 0.87739 (14) | 1.21631 (11) | −0.18180 (9) | 0.0208 (2) | |
H13 | 0.974 (2) | 1.2986 (18) | −0.1407 (14) | 0.039 (4)* | |
C14 | 0.77321 (14) | 1.12241 (10) | −0.13291 (8) | 0.01714 (18) | |
H14 | 0.796 (2) | 1.1411 (16) | −0.0549 (13) | 0.031 (4)* | |
C15 | 0.97367 (13) | 1.09930 (10) | 0.22897 (8) | 0.01359 (16) | |
H15A | 1.0524 (17) | 1.0589 (13) | 0.2021 (10) | 0.013 (3)* | |
H15B | 0.8901 (18) | 1.1204 (14) | 0.1646 (11) | 0.019 (3)* | |
C16 | 1.08512 (12) | 1.23457 (10) | 0.30761 (8) | 0.01436 (17) | |
H16B | 1.1659 (18) | 1.2924 (14) | 0.2730 (11) | 0.021 (3)* | |
H16A | 1.1643 (18) | 1.2117 (14) | 0.3725 (11) | 0.022 (3)* | |
C17 | 0.96790 (12) | 1.31233 (9) | 0.33662 (7) | 0.01351 (17) | |
C18 | 0.90244 (13) | 1.28766 (10) | 0.42395 (8) | 0.01619 (18) | |
H18 | 0.9416 (18) | 1.2227 (14) | 0.4720 (11) | 0.021 (3)* | |
C19 | 0.78662 (14) | 1.35502 (11) | 0.44617 (8) | 0.01860 (19) | |
H19 | 0.7421 (18) | 1.3349 (14) | 0.5078 (11) | 0.022 (3)* | |
C20 | 0.73618 (14) | 1.44989 (11) | 0.38173 (9) | 0.01931 (19) | |
H20 | 0.658 (2) | 1.4978 (15) | 0.4001 (12) | 0.028 (4)* | |
C21 | 0.80260 (14) | 1.47698 (10) | 0.29578 (8) | 0.01828 (19) | |
H21 | 0.7735 (19) | 1.5465 (15) | 0.2518 (12) | 0.024 (3)* | |
C22 | 0.91731 (13) | 1.40873 (10) | 0.27311 (8) | 0.01578 (18) | |
H22 | 0.9588 (18) | 1.4296 (14) | 0.2116 (11) | 0.019 (3)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O21 | 0.0230 (4) | 0.0213 (4) | 0.0153 (3) | −0.0007 (3) | 0.0019 (3) | 0.0029 (3) |
O22 | 0.0209 (4) | 0.0182 (3) | 0.0231 (4) | 0.0014 (3) | 0.0112 (3) | 0.0063 (3) |
O41 | 0.0254 (4) | 0.0195 (3) | 0.0137 (3) | 0.0027 (3) | 0.0045 (3) | 0.0013 (3) |
O42 | 0.0231 (4) | 0.0255 (4) | 0.0163 (3) | 0.0058 (3) | 0.0102 (3) | 0.0083 (3) |
N1 | 0.0166 (4) | 0.0142 (3) | 0.0116 (3) | 0.0029 (3) | 0.0051 (3) | 0.0021 (3) |
N2 | 0.0149 (4) | 0.0137 (3) | 0.0168 (4) | 0.0042 (3) | 0.0053 (3) | 0.0036 (3) |
N4 | 0.0178 (4) | 0.0165 (4) | 0.0129 (3) | 0.0083 (3) | 0.0062 (3) | 0.0043 (3) |
N5 | 0.0148 (4) | 0.0133 (3) | 0.0123 (3) | 0.0037 (3) | 0.0048 (3) | 0.0025 (3) |
C1 | 0.0134 (4) | 0.0130 (4) | 0.0128 (4) | 0.0063 (3) | 0.0053 (3) | 0.0037 (3) |
C2 | 0.0125 (4) | 0.0123 (4) | 0.0138 (4) | 0.0038 (3) | 0.0042 (3) | 0.0030 (3) |
C3 | 0.0139 (4) | 0.0136 (4) | 0.0147 (4) | 0.0066 (3) | 0.0064 (3) | 0.0047 (3) |
C4 | 0.0150 (4) | 0.0141 (4) | 0.0107 (4) | 0.0067 (3) | 0.0054 (3) | 0.0035 (3) |
C5 | 0.0127 (4) | 0.0126 (4) | 0.0136 (4) | 0.0064 (3) | 0.0047 (3) | 0.0032 (3) |
C6 | 0.0139 (4) | 0.0137 (4) | 0.0127 (4) | 0.0049 (3) | 0.0064 (3) | 0.0032 (3) |
C7 | 0.0157 (4) | 0.0159 (4) | 0.0130 (4) | 0.0061 (3) | 0.0065 (3) | 0.0037 (3) |
C8 | 0.0165 (4) | 0.0198 (4) | 0.0201 (4) | 0.0090 (4) | 0.0097 (4) | 0.0083 (4) |
C9 | 0.0130 (4) | 0.0148 (4) | 0.0160 (4) | 0.0070 (3) | 0.0060 (3) | 0.0043 (3) |
C10 | 0.0148 (4) | 0.0148 (4) | 0.0155 (4) | 0.0041 (3) | 0.0038 (3) | 0.0021 (3) |
C11 | 0.0209 (5) | 0.0220 (5) | 0.0179 (4) | 0.0090 (4) | 0.0093 (4) | 0.0066 (4) |
C12 | 0.0181 (4) | 0.0186 (4) | 0.0304 (5) | 0.0069 (4) | 0.0121 (4) | 0.0101 (4) |
C13 | 0.0149 (4) | 0.0137 (4) | 0.0306 (5) | 0.0034 (3) | 0.0043 (4) | 0.0010 (4) |
C14 | 0.0174 (4) | 0.0180 (4) | 0.0156 (4) | 0.0080 (4) | 0.0028 (3) | 0.0007 (3) |
C15 | 0.0138 (4) | 0.0142 (4) | 0.0147 (4) | 0.0052 (3) | 0.0064 (3) | 0.0038 (3) |
C16 | 0.0123 (4) | 0.0152 (4) | 0.0151 (4) | 0.0039 (3) | 0.0041 (3) | 0.0029 (3) |
C17 | 0.0126 (4) | 0.0125 (4) | 0.0134 (4) | 0.0027 (3) | 0.0026 (3) | 0.0008 (3) |
C18 | 0.0176 (4) | 0.0150 (4) | 0.0154 (4) | 0.0041 (3) | 0.0054 (3) | 0.0030 (3) |
C19 | 0.0195 (4) | 0.0186 (4) | 0.0178 (4) | 0.0045 (4) | 0.0081 (4) | 0.0013 (3) |
C20 | 0.0177 (4) | 0.0177 (4) | 0.0221 (5) | 0.0066 (4) | 0.0057 (4) | −0.0016 (4) |
C21 | 0.0192 (4) | 0.0155 (4) | 0.0191 (4) | 0.0067 (4) | 0.0035 (4) | 0.0021 (3) |
C22 | 0.0170 (4) | 0.0154 (4) | 0.0145 (4) | 0.0049 (3) | 0.0045 (3) | 0.0030 (3) |
O21—N2 | 1.2475 (11) | C9—C10 | 1.3980 (13) |
O22—N2 | 1.2354 (10) | C10—C11 | 1.3925 (13) |
O41—N4 | 1.2489 (11) | C10—H10 | 0.966 (15) |
O42—N4 | 1.2356 (10) | C11—C12 | 1.3905 (15) |
N1—C1 | 1.3544 (12) | C11—H11 | 1.006 (16) |
N1—C7 | 1.4543 (12) | C12—C13 | 1.3880 (16) |
N1—H1 | 0.891 (15) | C12—H12 | 0.965 (17) |
N2—C2 | 1.4363 (12) | C13—C14 | 1.3968 (15) |
N4—C4 | 1.4376 (12) | C13—H13 | 0.963 (17) |
N5—C5 | 1.3456 (12) | C14—H14 | 0.980 (16) |
N5—C15 | 1.4592 (12) | C15—C16 | 1.5320 (13) |
N5—H5 | 0.900 (17) | C15—H15A | 0.983 (13) |
C1—C6 | 1.4025 (13) | C15—H15B | 0.999 (13) |
C1—C2 | 1.4428 (12) | C16—C17 | 1.5113 (13) |
C2—C3 | 1.3832 (13) | C16—H16B | 0.979 (14) |
C3—C4 | 1.3805 (13) | C16—H16A | 0.994 (14) |
C3—H3 | 0.961 (14) | C17—C18 | 1.3995 (13) |
C4—C5 | 1.4434 (12) | C17—C22 | 1.4009 (13) |
C5—C6 | 1.4039 (13) | C18—C19 | 1.3948 (14) |
C6—H6 | 0.947 (14) | C18—H18 | 0.996 (14) |
C7—C8 | 1.5337 (14) | C19—C20 | 1.3945 (15) |
C7—H7A | 0.969 (13) | C19—H19 | 0.983 (14) |
C7—H7B | 0.965 (13) | C20—C21 | 1.3900 (15) |
C8—C9 | 1.5065 (13) | C20—H20 | 0.974 (15) |
C8—H8B | 0.977 (14) | C21—C22 | 1.3952 (14) |
C8—H8A | 1.000 (15) | C21—H21 | 0.978 (14) |
C9—C14 | 1.3956 (13) | C22—H22 | 0.971 (13) |
C1—N1—C7 | 124.07 (8) | C11—C10—C9 | 120.67 (9) |
C1—N1—H1 | 115.8 (10) | C11—C10—H10 | 119.9 (9) |
C7—N1—H1 | 119.0 (10) | C9—C10—H10 | 119.4 (9) |
O22—N2—O21 | 121.71 (8) | C12—C11—C10 | 119.99 (9) |
O22—N2—C2 | 119.42 (8) | C12—C11—H11 | 118.8 (9) |
O21—N2—C2 | 118.88 (8) | C10—C11—H11 | 121.2 (9) |
O42—N4—O41 | 121.81 (8) | C13—C12—C11 | 120.05 (9) |
O42—N4—C4 | 119.44 (8) | C13—C12—H12 | 118.1 (10) |
O41—N4—C4 | 118.75 (8) | C11—C12—H12 | 121.8 (10) |
C5—N5—C15 | 124.42 (8) | C12—C13—C14 | 119.84 (9) |
C5—N5—H5 | 118.4 (10) | C12—C13—H13 | 118.5 (10) |
C15—N5—H5 | 116.8 (10) | C14—C13—H13 | 121.7 (10) |
N1—C1—C6 | 121.20 (8) | C9—C14—C13 | 120.72 (9) |
N1—C1—C2 | 122.14 (8) | C9—C14—H14 | 119.6 (9) |
C6—C1—C2 | 116.66 (8) | C13—C14—H14 | 119.6 (9) |
C3—C2—N2 | 116.57 (8) | N5—C15—C16 | 110.11 (8) |
C3—C2—C1 | 120.46 (8) | N5—C15—H15A | 110.3 (7) |
N2—C2—C1 | 122.94 (8) | C16—C15—H15A | 111.1 (7) |
C4—C3—C2 | 121.62 (8) | N5—C15—H15B | 109.9 (8) |
C4—C3—H3 | 119.5 (8) | C16—C15—H15B | 108.9 (8) |
C2—C3—H3 | 118.9 (9) | H15A—C15—H15B | 106.3 (11) |
C3—C4—N4 | 116.64 (8) | C17—C16—C15 | 112.77 (8) |
C3—C4—C5 | 120.48 (8) | C17—C16—H16B | 109.9 (8) |
N4—C4—C5 | 122.85 (8) | C15—C16—H16B | 107.2 (8) |
N5—C5—C6 | 120.81 (8) | C17—C16—H16A | 111.8 (8) |
N5—C5—C4 | 122.58 (8) | C15—C16—H16A | 108.2 (8) |
C6—C5—C4 | 116.58 (8) | H16B—C16—H16A | 106.7 (11) |
C1—C6—C5 | 124.07 (8) | C18—C17—C22 | 118.37 (9) |
C1—C6—H6 | 118.1 (8) | C18—C17—C16 | 121.76 (8) |
C5—C6—H6 | 117.8 (8) | C22—C17—C16 | 119.84 (8) |
N1—C7—C8 | 111.96 (8) | C19—C18—C17 | 121.00 (9) |
N1—C7—H7A | 107.9 (7) | C19—C18—H18 | 119.6 (8) |
C8—C7—H7A | 108.4 (8) | C17—C18—H18 | 119.4 (8) |
N1—C7—H7B | 109.8 (8) | C20—C19—C18 | 120.00 (9) |
C8—C7—H7B | 110.4 (8) | C20—C19—H19 | 121.0 (8) |
H7A—C7—H7B | 108.2 (11) | C18—C19—H19 | 119.0 (8) |
C9—C8—C7 | 112.29 (8) | C21—C20—C19 | 119.56 (9) |
C9—C8—H8B | 111.3 (8) | C21—C20—H20 | 121.8 (9) |
C7—C8—H8B | 106.6 (8) | C19—C20—H20 | 118.6 (9) |
C9—C8—H8A | 109.2 (8) | C20—C21—C22 | 120.38 (9) |
C7—C8—H8A | 108.3 (8) | C20—C21—H21 | 120.7 (8) |
H8B—C8—H8A | 109.0 (12) | C22—C21—H21 | 118.8 (8) |
C14—C9—C10 | 118.74 (9) | C21—C22—C17 | 120.68 (9) |
C14—C9—C8 | 120.54 (9) | C21—C22—H22 | 117.6 (8) |
C10—C9—C8 | 120.69 (9) | C17—C22—H22 | 121.7 (8) |
C7—N1—C1—C6 | −6.57 (14) | N5—C5—C6—C1 | −175.36 (8) |
C7—N1—C1—C2 | 174.69 (8) | C4—C5—C6—C1 | 3.10 (13) |
O22—N2—C2—C3 | −4.46 (12) | C1—N1—C7—C8 | −79.33 (11) |
O21—N2—C2—C3 | 175.24 (8) | N1—C7—C8—C9 | 172.60 (8) |
O22—N2—C2—C1 | 177.78 (8) | C7—C8—C9—C14 | −92.60 (11) |
O21—N2—C2—C1 | −2.53 (13) | C7—C8—C9—C10 | 85.24 (11) |
N1—C1—C2—C3 | 176.93 (8) | C14—C9—C10—C11 | −0.33 (14) |
C6—C1—C2—C3 | −1.86 (13) | C8—C9—C10—C11 | −178.21 (9) |
N1—C1—C2—N2 | −5.39 (14) | C9—C10—C11—C12 | 0.07 (15) |
C6—C1—C2—N2 | 175.82 (8) | C10—C11—C12—C13 | 0.16 (15) |
N2—C2—C3—C4 | −177.06 (8) | C11—C12—C13—C14 | −0.14 (15) |
C1—C2—C3—C4 | 0.76 (14) | C10—C9—C14—C13 | 0.36 (14) |
C2—C3—C4—N4 | −179.52 (8) | C8—C9—C14—C13 | 178.24 (9) |
C2—C3—C4—C5 | 2.36 (13) | C12—C13—C14—C9 | −0.13 (15) |
O42—N4—C4—C3 | −1.13 (12) | C5—N5—C15—C16 | 169.34 (8) |
O41—N4—C4—C3 | 178.37 (8) | N5—C15—C16—C17 | −66.94 (10) |
O42—N4—C4—C5 | 176.93 (8) | C15—C16—C17—C18 | 89.20 (11) |
O41—N4—C4—C5 | −3.57 (13) | C15—C16—C17—C22 | −88.67 (10) |
C15—N5—C5—C6 | −0.22 (13) | C22—C17—C18—C19 | 1.31 (14) |
C15—N5—C5—C4 | −178.58 (8) | C16—C17—C18—C19 | −176.60 (9) |
C3—C4—C5—N5 | 174.25 (8) | C17—C18—C19—C20 | −0.80 (15) |
N4—C4—C5—N5 | −3.74 (13) | C18—C19—C20—C21 | −0.24 (15) |
C3—C4—C5—C6 | −4.17 (13) | C19—C20—C21—C22 | 0.74 (15) |
N4—C4—C5—C6 | 177.83 (8) | C20—C21—C22—C17 | −0.22 (15) |
N1—C1—C6—C5 | −178.97 (8) | C18—C17—C22—C21 | −0.80 (14) |
C2—C1—C6—C5 | −0.17 (13) | C16—C17—C22—C21 | 177.15 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O21 | 0.891 (15) | 1.935 (15) | 2.6318 (11) | 133.8 (13) |
N5—H5···O41 | 0.900 (17) | 1.967 (16) | 2.6358 (11) | 129.8 (14) |
N5—H5···O41i | 0.900 (17) | 2.800 (17) | 3.5877 (11) | 146.8 (13) |
Symmetry code: (i) −x+2, −y+2, −z+1. |
C15H13N3O2 | F(000) = 560 |
Mr = 267.28 | Dx = 1.348 Mg m−3 |
Monoclinic, P21/n | Melting point: 427 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 7.4871 (5) Å | Cell parameters from 23429 reflections |
b = 16.270 (1) Å | θ = 2.3–33.0° |
c = 10.8432 (7) Å | µ = 0.09 mm−1 |
β = 94.384 (1)° | T = 100 K |
V = 1317.00 (15) Å3 | Parallelpiped, yellow |
Z = 4 | 0.40 × 0.20 × 0.10 mm |
Bruker APEX DUO CCD area-detector diffractometer | 4732 independent reflections |
Radiation source: sealed tube | 4189 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
ω scans | θmax = 32.9°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.964, Tmax = 0.991 | k = −24→24 |
23007 measured reflections | l = −16→16 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.113 | All H-atom parameters refined |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0687P)2 + 0.3103P] where P = (Fo2 + 2Fc2)/3 |
4732 reflections | (Δ/σ)max = 0.001 |
233 parameters | Δρmax = 0.56 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O41 | 0.28684 (9) | 0.12353 (4) | 0.29556 (6) | 0.02323 (14) | |
O42 | 0.10504 (8) | 0.03747 (4) | 0.37421 (6) | 0.02067 (13) | |
N1 | 0.65662 (8) | 0.09507 (4) | 0.83376 (6) | 0.01439 (12) | |
H1 | 0.6214 (19) | 0.0666 (9) | 0.8948 (14) | 0.033 (3)* | |
N2 | 0.33192 (10) | −0.05113 (4) | 0.89432 (7) | 0.02022 (14) | |
N4 | 0.23997 (8) | 0.08139 (4) | 0.38232 (6) | 0.01466 (13) | |
C1 | 0.55906 (9) | 0.09106 (4) | 0.72443 (6) | 0.01199 (13) | |
C2 | 0.40849 (9) | 0.03712 (4) | 0.70702 (6) | 0.01168 (13) | |
C3 | 0.30296 (9) | 0.03411 (4) | 0.59568 (7) | 0.01221 (13) | |
H3 | 0.2029 (15) | −0.0007 (7) | 0.5865 (11) | 0.019 (3)* | |
C4 | 0.34763 (9) | 0.08426 (4) | 0.49902 (6) | 0.01264 (13) | |
C5 | 0.49621 (10) | 0.13679 (5) | 0.51165 (7) | 0.01499 (14) | |
H5 | 0.5272 (16) | 0.1712 (8) | 0.4445 (11) | 0.021 (3)* | |
C6 | 0.59954 (10) | 0.13990 (5) | 0.62209 (7) | 0.01514 (14) | |
H6 | 0.6992 (17) | 0.1754 (8) | 0.6296 (12) | 0.024 (3)* | |
C7 | 0.80953 (9) | 0.14949 (5) | 0.86030 (7) | 0.01465 (14) | |
H7A | 0.7833 (16) | 0.2054 (7) | 0.8259 (11) | 0.020 (3)* | |
H7B | 0.8227 (16) | 0.1545 (8) | 0.9503 (12) | 0.022 (3)* | |
C8 | 0.98355 (10) | 0.11550 (5) | 0.81298 (8) | 0.01875 (15) | |
H8B | 0.9959 (18) | 0.0584 (8) | 0.8430 (13) | 0.029 (3)* | |
H8A | 0.9744 (18) | 0.1137 (8) | 0.7233 (13) | 0.030 (3)* | |
C9 | 1.14367 (9) | 0.16670 (5) | 0.85827 (7) | 0.01476 (14) | |
C10 | 1.22232 (10) | 0.15533 (5) | 0.97834 (7) | 0.01569 (14) | |
H10 | 1.1749 (18) | 0.1134 (8) | 1.0314 (13) | 0.027 (3)* | |
C11 | 1.36857 (10) | 0.20255 (5) | 1.02246 (7) | 0.01573 (14) | |
H11 | 1.4201 (18) | 0.1936 (8) | 1.1055 (12) | 0.026 (3)* | |
C12 | 1.43693 (10) | 0.26274 (5) | 0.94762 (7) | 0.01653 (14) | |
H12 | 1.5371 (18) | 0.2976 (8) | 0.9811 (13) | 0.030 (3)* | |
C13 | 1.36012 (10) | 0.27489 (5) | 0.82797 (7) | 0.01769 (15) | |
H13 | 1.4088 (18) | 0.3160 (8) | 0.7747 (13) | 0.028 (3)* | |
C14 | 1.21486 (10) | 0.22666 (5) | 0.78384 (7) | 0.01678 (14) | |
H14 | 1.1657 (16) | 0.2334 (8) | 0.6966 (12) | 0.024 (3)* | |
C15 | 0.36369 (9) | −0.01308 (4) | 0.80896 (7) | 0.01396 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O41 | 0.0262 (3) | 0.0287 (3) | 0.0145 (3) | −0.0025 (2) | −0.0005 (2) | 0.0067 (2) |
O42 | 0.0176 (3) | 0.0243 (3) | 0.0194 (3) | −0.0046 (2) | −0.0032 (2) | −0.0013 (2) |
N1 | 0.0130 (3) | 0.0174 (3) | 0.0126 (3) | −0.0041 (2) | −0.0002 (2) | 0.0009 (2) |
N2 | 0.0213 (3) | 0.0208 (3) | 0.0186 (3) | −0.0022 (2) | 0.0014 (2) | 0.0046 (2) |
N4 | 0.0147 (3) | 0.0157 (3) | 0.0134 (3) | 0.0021 (2) | 0.0001 (2) | −0.0006 (2) |
C1 | 0.0101 (3) | 0.0129 (3) | 0.0131 (3) | −0.0004 (2) | 0.0014 (2) | 0.0003 (2) |
C2 | 0.0109 (3) | 0.0117 (3) | 0.0126 (3) | −0.0003 (2) | 0.0017 (2) | 0.0009 (2) |
C3 | 0.0109 (3) | 0.0123 (3) | 0.0135 (3) | 0.0000 (2) | 0.0014 (2) | −0.0001 (2) |
C4 | 0.0119 (3) | 0.0141 (3) | 0.0118 (3) | 0.0008 (2) | 0.0001 (2) | 0.0006 (2) |
C5 | 0.0142 (3) | 0.0161 (3) | 0.0148 (3) | −0.0016 (2) | 0.0018 (2) | 0.0030 (2) |
C6 | 0.0131 (3) | 0.0172 (3) | 0.0152 (3) | −0.0040 (2) | 0.0012 (2) | 0.0026 (2) |
C7 | 0.0120 (3) | 0.0162 (3) | 0.0157 (3) | −0.0023 (2) | 0.0002 (2) | −0.0024 (2) |
C8 | 0.0123 (3) | 0.0198 (3) | 0.0238 (4) | −0.0008 (2) | −0.0008 (3) | −0.0089 (3) |
C9 | 0.0105 (3) | 0.0159 (3) | 0.0178 (3) | 0.0012 (2) | 0.0001 (2) | −0.0052 (2) |
C10 | 0.0148 (3) | 0.0147 (3) | 0.0175 (3) | −0.0009 (2) | 0.0006 (2) | −0.0014 (2) |
C11 | 0.0140 (3) | 0.0173 (3) | 0.0155 (3) | 0.0000 (2) | −0.0012 (2) | −0.0019 (2) |
C12 | 0.0128 (3) | 0.0176 (3) | 0.0189 (3) | −0.0020 (2) | −0.0001 (2) | −0.0022 (3) |
C13 | 0.0161 (3) | 0.0190 (3) | 0.0181 (3) | −0.0004 (2) | 0.0022 (3) | 0.0010 (3) |
C14 | 0.0142 (3) | 0.0208 (3) | 0.0151 (3) | 0.0027 (2) | −0.0006 (2) | −0.0022 (3) |
C15 | 0.0126 (3) | 0.0137 (3) | 0.0154 (3) | −0.0012 (2) | 0.0003 (2) | 0.0001 (2) |
O41—N4 | 1.2364 (9) | C7—C8 | 1.5391 (11) |
O42—N4 | 1.2351 (9) | C7—H7A | 0.997 (12) |
N1—C1 | 1.3456 (9) | C7—H7B | 0.976 (13) |
N1—C7 | 1.4585 (9) | C8—C9 | 1.5107 (10) |
N1—H1 | 0.866 (15) | C8—H8B | 0.986 (14) |
N2—C15 | 1.1534 (10) | C8—H8A | 0.970 (14) |
N4—C4 | 1.4481 (9) | C9—C14 | 1.3975 (11) |
C1—C6 | 1.4163 (10) | C9—C10 | 1.3995 (11) |
C1—C2 | 1.4298 (9) | C10—C11 | 1.3921 (10) |
C2—C3 | 1.3923 (10) | C10—H10 | 0.977 (13) |
C2—C15 | 1.4346 (10) | C11—C12 | 1.3938 (11) |
C3—C4 | 1.3892 (10) | C11—H11 | 0.963 (13) |
C3—H3 | 0.938 (12) | C12—C13 | 1.3925 (11) |
C4—C5 | 1.4013 (10) | C12—H12 | 0.987 (14) |
C5—C6 | 1.3761 (10) | C13—C14 | 1.3957 (11) |
C5—H5 | 0.961 (12) | C13—H13 | 0.972 (14) |
C6—H6 | 0.942 (13) | C14—H14 | 0.994 (13) |
C1—N1—C7 | 124.63 (6) | C8—C7—H7B | 109.9 (7) |
C1—N1—H1 | 118.1 (10) | H7A—C7—H7B | 107.4 (10) |
C7—N1—H1 | 117.0 (10) | C9—C8—C7 | 111.37 (6) |
O42—N4—O41 | 123.01 (7) | C9—C8—H8B | 111.1 (8) |
O42—N4—C4 | 118.59 (6) | C7—C8—H8B | 106.8 (8) |
O41—N4—C4 | 118.40 (6) | C9—C8—H8A | 109.7 (8) |
N1—C1—C6 | 121.93 (6) | C7—C8—H8A | 110.4 (8) |
N1—C1—C2 | 121.03 (6) | H8B—C8—H8A | 107.4 (11) |
C6—C1—C2 | 117.04 (6) | C14—C9—C10 | 118.53 (7) |
C3—C2—C1 | 121.71 (6) | C14—C9—C8 | 121.69 (7) |
C3—C2—C15 | 119.83 (6) | C10—C9—C8 | 119.77 (7) |
C1—C2—C15 | 118.43 (6) | C11—C10—C9 | 120.71 (7) |
C4—C3—C2 | 118.70 (6) | C11—C10—H10 | 119.6 (8) |
C4—C3—H3 | 120.7 (7) | C9—C10—H10 | 119.6 (8) |
C2—C3—H3 | 120.6 (7) | C10—C11—C12 | 120.12 (7) |
C3—C4—C5 | 121.31 (7) | C10—C11—H11 | 119.1 (8) |
C3—C4—N4 | 119.36 (6) | C12—C11—H11 | 120.8 (8) |
C5—C4—N4 | 119.32 (6) | C13—C12—C11 | 119.89 (7) |
C6—C5—C4 | 119.78 (7) | C13—C12—H12 | 120.6 (8) |
C6—C5—H5 | 119.1 (7) | C11—C12—H12 | 119.5 (8) |
C4—C5—H5 | 121.1 (7) | C12—C13—C14 | 119.67 (7) |
C5—C6—C1 | 121.44 (7) | C12—C13—H13 | 120.3 (8) |
C5—C6—H6 | 119.1 (8) | C14—C13—H13 | 120.0 (8) |
C1—C6—H6 | 119.5 (8) | C13—C14—C9 | 121.07 (7) |
N1—C7—C8 | 112.82 (6) | C13—C14—H14 | 119.1 (7) |
N1—C7—H7A | 110.5 (7) | C9—C14—H14 | 119.8 (7) |
C8—C7—H7A | 110.5 (7) | N2—C15—C2 | 177.02 (8) |
N1—C7—H7B | 105.4 (7) | ||
C7—N1—C1—C6 | 1.06 (11) | C4—C5—C6—C1 | −0.14 (11) |
C7—N1—C1—C2 | −178.63 (6) | N1—C1—C6—C5 | −178.37 (7) |
N1—C1—C2—C3 | 178.00 (7) | C2—C1—C6—C5 | 1.33 (11) |
C6—C1—C2—C3 | −1.70 (10) | C1—N1—C7—C8 | −81.27 (9) |
N1—C1—C2—C15 | −0.18 (10) | N1—C7—C8—C9 | −171.53 (6) |
C6—C1—C2—C15 | −179.88 (6) | C7—C8—C9—C14 | −98.73 (8) |
C1—C2—C3—C4 | 0.87 (10) | C7—C8—C9—C10 | 80.25 (9) |
C15—C2—C3—C4 | 179.03 (6) | C14—C9—C10—C11 | −0.20 (11) |
C2—C3—C4—C5 | 0.39 (11) | C8—C9—C10—C11 | −179.21 (7) |
C2—C3—C4—N4 | 179.54 (6) | C9—C10—C11—C12 | 0.90 (11) |
O42—N4—C4—C3 | 3.91 (10) | C10—C11—C12—C13 | −0.82 (11) |
O41—N4—C4—C3 | −176.58 (7) | C11—C12—C13—C14 | 0.06 (12) |
O42—N4—C4—C5 | −176.93 (7) | C12—C13—C14—C9 | 0.65 (12) |
O41—N4—C4—C5 | 2.58 (10) | C10—C9—C14—C13 | −0.58 (11) |
C3—C4—C5—C6 | −0.76 (11) | C8—C9—C14—C13 | 178.41 (7) |
N4—C4—C5—C6 | −179.91 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N2i | 0.866 (15) | 2.300 (15) | 3.0287 (10) | 141.9 (12) |
Symmetry code: (i) −x+1, −y, −z+2. |
C15H16N2O4S | Dx = 1.412 Mg m−3 |
Mr = 320.36 | Melting point: 414 K |
Tetragonal, I41/a | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -I 4ad | Cell parameters from 53474 reflections |
a = 20.4639 (13) Å | θ = 2.6–32.9° |
c = 14.3952 (14) Å | µ = 0.24 mm−1 |
V = 6028.3 (10) Å3 | T = 100 K |
Z = 16 | Cuboid, yellow |
F(000) = 2688 | 0.40 × 0.20 × 0.20 mm |
Bruker APEX DUO CCD area-detector diffractometer | 5524 independent reflections |
Radiation source: sealed tube | 5155 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
ω scans | θmax = 32.9°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −30→31 |
Tmin = 0.912, Tmax = 0.955 | k = −31→30 |
52424 measured reflections | l = −21→21 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.029 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.086 | All H-atom parameters refined |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0494P)2 + 3.0117P] where P = (Fo2 + 2Fc2)/3 |
5524 reflections | (Δ/σ)max = 0.002 |
263 parameters | Δρmax = 0.51 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.918999 (8) | 0.384073 (8) | 0.115221 (13) | 0.01486 (5) | |
O21 | 0.72956 (3) | 0.62358 (3) | 0.13034 (5) | 0.02619 (14) | |
O22 | 0.83430 (3) | 0.61924 (3) | 0.15113 (5) | 0.02251 (12) | |
O41 | 0.91451 (3) | 0.33599 (3) | 0.04188 (4) | 0.02179 (12) | |
O42 | 0.96848 (3) | 0.43425 (3) | 0.10731 (5) | 0.02180 (12) | |
N1 | 0.66040 (3) | 0.51537 (3) | 0.11584 (5) | 0.01679 (12) | |
H1 | 0.6604 (7) | 0.5584 (8) | 0.1202 (10) | 0.038 (4)* | |
N2 | 0.78132 (3) | 0.59202 (3) | 0.13760 (5) | 0.01652 (11) | |
C1 | 0.71927 (3) | 0.48639 (3) | 0.12182 (5) | 0.01391 (12) | |
C2 | 0.77942 (3) | 0.52165 (3) | 0.13051 (5) | 0.01370 (12) | |
C3 | 0.84001 (3) | 0.49002 (3) | 0.13130 (5) | 0.01447 (12) | |
H3 | 0.8791 (7) | 0.5168 (6) | 0.1359 (9) | 0.026 (3)* | |
C4 | 0.84249 (3) | 0.42282 (3) | 0.12432 (5) | 0.01465 (12) | |
C5 | 0.78421 (4) | 0.38584 (4) | 0.11955 (5) | 0.01666 (13) | |
H5 | 0.7859 (6) | 0.3384 (6) | 0.1168 (8) | 0.023 (3)* | |
C6 | 0.72458 (4) | 0.41678 (4) | 0.11892 (5) | 0.01637 (13) | |
H6 | 0.6879 (6) | 0.3928 (6) | 0.1145 (9) | 0.023 (3)* | |
C7 | 0.59791 (4) | 0.48089 (4) | 0.11108 (5) | 0.01798 (13) | |
H7A | 0.5906 (5) | 0.4561 (5) | 0.1693 (8) | 0.015 (2)* | |
H7B | 0.5982 (6) | 0.4507 (6) | 0.0597 (8) | 0.018 (3)* | |
C8 | 0.54312 (4) | 0.53117 (4) | 0.09737 (5) | 0.01863 (13) | |
H8A | 0.5029 (6) | 0.5080 (6) | 0.0915 (9) | 0.021 (3)* | |
H8B | 0.5525 (6) | 0.5542 (6) | 0.0391 (9) | 0.025 (3)* | |
C9 | 0.53881 (3) | 0.57928 (4) | 0.17680 (5) | 0.01547 (12) | |
C10 | 0.56452 (4) | 0.64241 (4) | 0.17008 (5) | 0.01871 (13) | |
H10 | 0.5853 (6) | 0.6565 (7) | 0.1136 (9) | 0.026 (3)* | |
C11 | 0.56197 (4) | 0.68488 (4) | 0.24613 (6) | 0.02200 (15) | |
H11 | 0.5775 (6) | 0.7276 (7) | 0.2407 (10) | 0.029 (3)* | |
C12 | 0.53446 (4) | 0.66439 (4) | 0.32954 (6) | 0.02297 (15) | |
H12 | 0.5339 (7) | 0.6937 (7) | 0.3812 (10) | 0.034 (4)* | |
C13 | 0.50872 (4) | 0.60148 (4) | 0.33686 (5) | 0.02155 (14) | |
H13 | 0.4898 (7) | 0.5856 (7) | 0.3950 (10) | 0.031 (3)* | |
C14 | 0.51036 (4) | 0.55957 (4) | 0.26071 (5) | 0.01777 (13) | |
H14 | 0.4927 (6) | 0.5155 (6) | 0.2656 (9) | 0.022 (3)* | |
C15 | 0.92951 (4) | 0.34181 (4) | 0.22080 (6) | 0.02208 (14) | |
H15A | 0.9299 (6) | 0.3726 (7) | 0.2701 (10) | 0.031 (3)* | |
H15B | 0.8929 (7) | 0.3095 (7) | 0.2271 (10) | 0.034 (3)* | |
H15C | 0.9713 (7) | 0.3212 (7) | 0.2172 (10) | 0.037 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.01361 (8) | 0.01350 (8) | 0.01747 (9) | 0.00014 (5) | 0.00355 (5) | −0.00138 (5) |
O21 | 0.0209 (3) | 0.0141 (2) | 0.0435 (4) | 0.0033 (2) | −0.0035 (2) | −0.0016 (2) |
O22 | 0.0192 (3) | 0.0156 (2) | 0.0328 (3) | −0.00497 (19) | 0.0030 (2) | −0.0024 (2) |
O41 | 0.0247 (3) | 0.0191 (2) | 0.0216 (3) | 0.0014 (2) | 0.0052 (2) | −0.0065 (2) |
O42 | 0.0150 (2) | 0.0172 (2) | 0.0332 (3) | −0.00241 (19) | 0.0043 (2) | −0.0003 (2) |
N1 | 0.0135 (3) | 0.0149 (3) | 0.0220 (3) | 0.0003 (2) | −0.0005 (2) | −0.0027 (2) |
N2 | 0.0184 (3) | 0.0123 (2) | 0.0188 (3) | −0.0008 (2) | 0.0017 (2) | −0.0005 (2) |
C1 | 0.0138 (3) | 0.0140 (3) | 0.0140 (3) | −0.0006 (2) | 0.0006 (2) | −0.0017 (2) |
C2 | 0.0149 (3) | 0.0105 (3) | 0.0156 (3) | −0.0010 (2) | 0.0010 (2) | −0.0012 (2) |
C3 | 0.0142 (3) | 0.0135 (3) | 0.0157 (3) | −0.0011 (2) | 0.0011 (2) | −0.0015 (2) |
C4 | 0.0138 (3) | 0.0128 (3) | 0.0173 (3) | −0.0002 (2) | 0.0014 (2) | −0.0016 (2) |
C5 | 0.0159 (3) | 0.0131 (3) | 0.0210 (3) | −0.0010 (2) | 0.0007 (2) | −0.0022 (2) |
C6 | 0.0148 (3) | 0.0133 (3) | 0.0210 (3) | −0.0019 (2) | 0.0006 (2) | −0.0024 (2) |
C7 | 0.0140 (3) | 0.0191 (3) | 0.0209 (3) | −0.0016 (2) | 0.0003 (2) | −0.0048 (2) |
C8 | 0.0142 (3) | 0.0259 (3) | 0.0159 (3) | 0.0013 (2) | −0.0016 (2) | −0.0044 (3) |
C9 | 0.0116 (3) | 0.0203 (3) | 0.0145 (3) | 0.0027 (2) | −0.0010 (2) | −0.0006 (2) |
C10 | 0.0176 (3) | 0.0209 (3) | 0.0176 (3) | 0.0014 (2) | −0.0006 (2) | 0.0027 (2) |
C11 | 0.0242 (3) | 0.0178 (3) | 0.0240 (4) | 0.0021 (3) | −0.0030 (3) | 0.0002 (3) |
C12 | 0.0270 (4) | 0.0221 (3) | 0.0198 (3) | 0.0072 (3) | −0.0021 (3) | −0.0044 (3) |
C13 | 0.0225 (3) | 0.0256 (4) | 0.0166 (3) | 0.0053 (3) | 0.0033 (3) | −0.0006 (3) |
C14 | 0.0155 (3) | 0.0202 (3) | 0.0175 (3) | 0.0018 (2) | 0.0020 (2) | 0.0002 (2) |
C15 | 0.0201 (3) | 0.0257 (4) | 0.0205 (3) | 0.0041 (3) | 0.0026 (3) | 0.0032 (3) |
S1—O41 | 1.4462 (6) | C7—H7A | 0.992 (11) |
S1—O42 | 1.4467 (6) | C7—H7B | 0.964 (12) |
S1—C4 | 1.7599 (7) | C8—C9 | 1.5114 (10) |
S1—C15 | 1.7619 (8) | C8—H8A | 0.954 (12) |
O21—N2 | 1.2449 (9) | C8—H8B | 0.982 (13) |
O22—N2 | 1.2345 (9) | C9—C10 | 1.3983 (11) |
N1—C1 | 1.3454 (9) | C9—C14 | 1.4002 (10) |
N1—C7 | 1.4623 (10) | C10—C11 | 1.3989 (11) |
N1—H1 | 0.882 (16) | C10—H10 | 0.962 (13) |
N2—C2 | 1.4441 (9) | C11—C12 | 1.3909 (12) |
C1—C6 | 1.4293 (10) | C11—H11 | 0.934 (13) |
C1—C2 | 1.4322 (10) | C12—C13 | 1.3949 (12) |
C2—C3 | 1.3989 (10) | C12—H12 | 0.955 (14) |
C3—C4 | 1.3797 (10) | C13—C14 | 1.3922 (11) |
C3—H3 | 0.973 (14) | C13—H13 | 0.977 (14) |
C4—C5 | 1.4142 (10) | C14—H14 | 0.974 (12) |
C5—C6 | 1.3746 (10) | C15—H15A | 0.949 (14) |
C5—H5 | 0.972 (13) | C15—H15B | 1.003 (14) |
C6—H6 | 0.898 (13) | C15—H15C | 0.955 (14) |
C7—C8 | 1.5344 (11) | ||
O41—S1—O42 | 118.03 (4) | N1—C7—H7B | 109.8 (7) |
O41—S1—C4 | 107.72 (4) | C8—C7—H7B | 109.6 (7) |
O42—S1—C4 | 107.99 (3) | H7A—C7—H7B | 108.8 (10) |
O41—S1—C15 | 107.66 (4) | C9—C8—C7 | 112.47 (6) |
O42—S1—C15 | 109.33 (4) | C9—C8—H8A | 109.9 (7) |
C4—S1—C15 | 105.40 (4) | C7—C8—H8A | 108.0 (7) |
C1—N1—C7 | 125.00 (6) | C9—C8—H8B | 110.2 (8) |
C1—N1—H1 | 115.8 (10) | C7—C8—H8B | 106.9 (7) |
C7—N1—H1 | 118.9 (10) | H8A—C8—H8B | 109.3 (10) |
O22—N2—O21 | 121.76 (7) | C10—C9—C14 | 118.84 (7) |
O22—N2—C2 | 119.00 (6) | C10—C9—C8 | 121.84 (7) |
O21—N2—C2 | 119.24 (6) | C14—C9—C8 | 119.29 (7) |
N1—C1—C6 | 120.36 (7) | C9—C10—C11 | 120.39 (7) |
N1—C1—C2 | 123.58 (7) | C9—C10—H10 | 120.1 (8) |
C6—C1—C2 | 116.06 (6) | C11—C10—H10 | 119.4 (8) |
C3—C2—C1 | 121.96 (6) | C12—C11—C10 | 120.22 (8) |
C3—C2—N2 | 115.91 (6) | C12—C11—H11 | 119.5 (8) |
C1—C2—N2 | 122.12 (6) | C10—C11—H11 | 120.3 (9) |
C4—C3—C2 | 119.55 (6) | C11—C12—C13 | 119.76 (7) |
C4—C3—H3 | 122.5 (8) | C11—C12—H12 | 119.2 (9) |
C2—C3—H3 | 117.9 (8) | C13—C12—H12 | 121.0 (9) |
C3—C4—C5 | 120.39 (7) | C14—C13—C12 | 120.00 (7) |
C3—C4—S1 | 119.15 (5) | C14—C13—H13 | 118.6 (8) |
C5—C4—S1 | 120.37 (5) | C12—C13—H13 | 121.4 (8) |
C6—C5—C4 | 120.17 (7) | C13—C14—C9 | 120.78 (7) |
C6—C5—H5 | 119.5 (8) | C13—C14—H14 | 120.3 (7) |
C4—C5—H5 | 120.4 (8) | C9—C14—H14 | 118.9 (7) |
C5—C6—C1 | 121.75 (7) | S1—C15—H15A | 108.7 (8) |
C5—C6—H6 | 119.4 (8) | S1—C15—H15B | 108.1 (8) |
C1—C6—H6 | 118.9 (8) | H15A—C15—H15B | 112.0 (11) |
N1—C7—C8 | 108.76 (6) | S1—C15—H15C | 106.2 (9) |
N1—C7—H7A | 109.9 (6) | H15A—C15—H15C | 109.1 (12) |
C8—C7—H7A | 110.0 (6) | H15B—C15—H15C | 112.6 (12) |
C7—N1—C1—C6 | 3.38 (11) | C15—S1—C4—C5 | −72.35 (7) |
C7—N1—C1—C2 | −177.13 (7) | C3—C4—C5—C6 | 2.03 (11) |
N1—C1—C2—C3 | −176.34 (7) | S1—C4—C5—C6 | −174.59 (6) |
C6—C1—C2—C3 | 3.18 (10) | C4—C5—C6—C1 | 0.80 (11) |
N1—C1—C2—N2 | 2.73 (11) | N1—C1—C6—C5 | 176.24 (7) |
C6—C1—C2—N2 | −177.76 (6) | C2—C1—C6—C5 | −3.29 (10) |
O22—N2—C2—C3 | −5.65 (10) | C1—N1—C7—C8 | −175.70 (7) |
O21—N2—C2—C3 | 174.68 (7) | N1—C7—C8—C9 | −61.20 (8) |
O22—N2—C2—C1 | 175.24 (7) | C7—C8—C9—C10 | 101.15 (8) |
O21—N2—C2—C1 | −4.44 (10) | C7—C8—C9—C14 | −76.55 (8) |
C1—C2—C3—C4 | −0.55 (10) | C14—C9—C10—C11 | 0.21 (11) |
N2—C2—C3—C4 | −179.66 (6) | C8—C9—C10—C11 | −177.50 (7) |
C2—C3—C4—C5 | −2.14 (10) | C9—C10—C11—C12 | 0.74 (12) |
C2—C3—C4—S1 | 174.53 (5) | C10—C11—C12—C13 | −0.70 (12) |
O41—S1—C4—C3 | −134.28 (6) | C11—C12—C13—C14 | −0.30 (12) |
O42—S1—C4—C3 | −5.78 (7) | C12—C13—C14—C9 | 1.27 (12) |
C15—S1—C4—C3 | 110.98 (6) | C10—C9—C14—C13 | −1.21 (11) |
O41—S1—C4—C5 | 42.39 (7) | C8—C9—C14—C13 | 176.56 (7) |
O42—S1—C4—C5 | 170.88 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O21 | 0.882 (16) | 1.951 (16) | 2.6364 (9) | 133.4 (14) |