A few pyrazinamide (Pyz) cocrystals involving hydroxybenzoic/cinnamic acid derivatives [2,4-dihydroxybenzoic acid (24DHBA); 2,6-dihydroxybenzoic acid (26DHBA); 3,5-dihydroxybenzoic acid (35DHBA) and nutraceutical molecule ferulic acid (FRA)] and the first example of a molecular salt with p-toluenesulfonic acid (pTSA) have been prepared and characterized using various solid-state techniques. A high-temperature cocrystal polymorph of Pyz·FRA has been characterized from the endothermic peaks observed using differential scanning calorimetry. The presence of substituent groups carrying hydrogen bond donors or acceptors and their influence on supramolecular synthon formation has been investigated using a Cambridge Structural Database search. Equilibrium solubility of all the binary complexes of Pyz follows the order of their coformer solubility, i.e. Pyz+·pTSA− > Pyz·35DHBA > Pyz > Pyz·26DHBA > Pyz·24DHBA > Pyz·FRA. A twofold enhancement in solubility of Pyz+·pTSA− molecular salt compared with the parent drug suggests a potential drug formulation for the treatment of tuberculosis.
Supporting information
CCDC references: 1504475; 1504478; 1504476; 1504479; 1504477; 1504479
For all structures, data collection: Bruker APEX2; cell refinement: Bruker SAINT; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXL2016/6 (Sheldrick, 2016); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2016); molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.
Crystal data top
C7H6O4·C5H5N3O | F(000) = 576 |
Mr = 277.24 | Dx = 1.470 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.7759 (8) Å | Cell parameters from 3570 reflections |
b = 6.7421 (6) Å | θ = 2.6–26.1° |
c = 23.996 (2) Å | µ = 0.12 mm−1 |
β = 95.224 (6)° | T = 296 K |
V = 1252.8 (2) Å3 | Block, colorless |
Z = 4 | 0.27 × 0.18 × 0.16 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 2124 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.030 |
φ and ω scans | θmax = 26.5°, θmin = 2.6° |
Absorption correction: multi-scan Bruker AXS SADABS program | h = −9→9 |
Tmin = 0.969, Tmax = 0.982 | k = −8→7 |
9812 measured reflections | l = −30→30 |
2564 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.044 | w = 1/[σ2(Fo2) + (0.0756P)2 + 0.1634P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.125 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.33 e Å−3 |
2564 reflections | Δρmin = −0.28 e Å−3 |
202 parameters | Extinction correction: SHELXL-2016/6 (Sheldrick 2016), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.066 (6) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.18875 (18) | 0.6795 (2) | 0.09166 (5) | 0.0370 (3) | |
C2 | 0.2703 (2) | 0.7256 (2) | 0.14391 (6) | 0.0418 (4) | |
H2 | 0.330179 | 0.844674 | 0.148827 | 0.050* | |
C3 | 0.1781 (2) | 0.4343 (3) | 0.17754 (6) | 0.0476 (4) | |
H3 | 0.171231 | 0.345003 | 0.206788 | 0.057* | |
C4 | 0.0980 (2) | 0.3883 (2) | 0.12528 (6) | 0.0456 (4) | |
H4 | 0.039495 | 0.268412 | 0.120369 | 0.055* | |
C5 | 0.1983 (2) | 0.8224 (2) | 0.04435 (6) | 0.0421 (4) | |
C6 | 0.68469 (18) | 0.6105 (2) | 0.10862 (6) | 0.0369 (3) | |
C7 | 0.74549 (18) | 0.6081 (2) | 0.16564 (6) | 0.0387 (4) | |
C8 | 0.7081 (2) | 0.4494 (2) | 0.19922 (6) | 0.0427 (4) | |
H8 | 0.748990 | 0.448344 | 0.236861 | 0.051* | |
C9 | 0.60961 (19) | 0.2920 (2) | 0.17678 (6) | 0.0409 (4) | |
C10 | 0.5481 (2) | 0.2927 (2) | 0.12037 (6) | 0.0431 (4) | |
H10 | 0.482197 | 0.187396 | 0.105233 | 0.052* | |
C11 | 0.58545 (19) | 0.4495 (2) | 0.08754 (6) | 0.0412 (4) | |
H11 | 0.543627 | 0.449288 | 0.049977 | 0.049* | |
C12 | 0.7288 (2) | 0.7731 (2) | 0.07251 (6) | 0.0425 (4) | |
H2A | 0.692 (3) | 0.856 (4) | −0.0020 (11) | 0.099 (8)* | |
H3A | 0.082 (3) | 0.646 (3) | −0.0107 (8) | 0.062 (6)* | |
H4A | 0.854 (3) | 0.855 (4) | 0.1618 (10) | 0.079 (7)* | |
H5A | 0.620 (3) | 0.135 (3) | 0.2413 (10) | 0.072 (6)* | |
H3B | 0.138 (3) | 0.848 (3) | −0.0342 (10) | 0.071 (6)* | |
N1 | 0.26447 (17) | 0.6029 (2) | 0.18705 (5) | 0.0450 (3) | |
N2 | 0.10226 (16) | 0.51007 (19) | 0.08191 (5) | 0.0399 (3) | |
N3 | 0.1311 (2) | 0.7680 (2) | −0.00544 (6) | 0.0537 (4) | |
O1 | 0.2658 (2) | 0.98595 (19) | 0.05387 (5) | 0.0690 (4) | |
O2 | 0.66837 (19) | 0.7519 (2) | 0.01996 (5) | 0.0688 (4) | |
O3 | 0.81772 (15) | 0.91669 (17) | 0.08891 (4) | 0.0512 (3) | |
O4 | 0.84357 (16) | 0.75641 (19) | 0.18942 (5) | 0.0550 (4) | |
O5 | 0.56468 (18) | 0.1350 (2) | 0.20717 (5) | 0.0602 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0395 (7) | 0.0393 (8) | 0.0315 (7) | −0.0015 (6) | −0.0002 (5) | −0.0017 (6) |
C2 | 0.0479 (8) | 0.0425 (9) | 0.0340 (7) | −0.0030 (7) | −0.0028 (6) | −0.0034 (6) |
C3 | 0.0595 (10) | 0.0489 (10) | 0.0337 (7) | 0.0036 (8) | 0.0003 (6) | 0.0056 (6) |
C4 | 0.0535 (9) | 0.0415 (9) | 0.0409 (8) | −0.0056 (7) | −0.0008 (6) | 0.0032 (6) |
C5 | 0.0489 (8) | 0.0431 (9) | 0.0332 (7) | −0.0107 (7) | −0.0029 (6) | −0.0007 (6) |
C6 | 0.0360 (7) | 0.0426 (9) | 0.0319 (7) | 0.0003 (6) | 0.0011 (5) | 0.0001 (6) |
C7 | 0.0389 (7) | 0.0445 (9) | 0.0320 (7) | −0.0003 (6) | −0.0006 (5) | −0.0068 (6) |
C8 | 0.0470 (8) | 0.0533 (10) | 0.0264 (6) | −0.0010 (7) | −0.0040 (5) | −0.0011 (6) |
C9 | 0.0452 (8) | 0.0441 (9) | 0.0330 (7) | 0.0000 (7) | 0.0007 (6) | 0.0044 (6) |
C10 | 0.0487 (8) | 0.0456 (9) | 0.0334 (7) | −0.0077 (7) | −0.0047 (6) | −0.0006 (6) |
C11 | 0.0459 (8) | 0.0487 (9) | 0.0277 (6) | −0.0031 (7) | −0.0039 (5) | 0.0009 (6) |
C12 | 0.0464 (8) | 0.0464 (9) | 0.0339 (7) | −0.0036 (7) | 0.0000 (6) | −0.0009 (6) |
N1 | 0.0529 (7) | 0.0503 (8) | 0.0303 (6) | 0.0038 (6) | −0.0048 (5) | −0.0019 (5) |
N2 | 0.0455 (7) | 0.0389 (7) | 0.0344 (6) | −0.0054 (6) | −0.0020 (5) | −0.0003 (5) |
N3 | 0.0806 (10) | 0.0487 (9) | 0.0300 (7) | −0.0244 (8) | −0.0047 (6) | 0.0014 (6) |
O1 | 0.1066 (11) | 0.0561 (8) | 0.0398 (6) | −0.0391 (8) | −0.0182 (6) | 0.0070 (5) |
O2 | 0.0998 (11) | 0.0680 (9) | 0.0347 (6) | −0.0382 (8) | −0.0143 (6) | 0.0128 (6) |
O3 | 0.0651 (7) | 0.0467 (7) | 0.0405 (6) | −0.0129 (6) | −0.0017 (5) | 0.0015 (5) |
O4 | 0.0712 (8) | 0.0530 (8) | 0.0385 (6) | −0.0161 (6) | −0.0078 (5) | −0.0054 (5) |
O5 | 0.0800 (9) | 0.0591 (8) | 0.0385 (6) | −0.0186 (7) | −0.0116 (6) | 0.0136 (5) |
Geometric parameters (Å, º) top
C1—N2 | 1.3353 (19) | C7—C8 | 1.386 (2) |
C1—C2 | 1.3878 (19) | C8—C9 | 1.388 (2) |
C1—C5 | 1.496 (2) | C8—H8 | 0.9300 |
C2—N1 | 1.329 (2) | C9—O5 | 1.3488 (19) |
C2—H2 | 0.9300 | C9—C10 | 1.3941 (19) |
C3—N1 | 1.329 (2) | C10—C11 | 1.365 (2) |
C3—C4 | 1.383 (2) | C10—H10 | 0.9300 |
C3—H3 | 0.9300 | C11—H11 | 0.9300 |
C4—N2 | 1.3283 (19) | C12—O3 | 1.2331 (19) |
C4—H4 | 0.9300 | C12—O2 | 1.3126 (18) |
C5—O1 | 1.2337 (19) | N3—H3A | 0.91 (2) |
C5—N3 | 1.3120 (19) | N3—H3B | 0.88 (2) |
C6—C11 | 1.399 (2) | O2—H2A | 0.91 (3) |
C6—C7 | 1.4064 (18) | O4—H4A | 0.95 (3) |
C6—C12 | 1.458 (2) | O5—H5A | 0.89 (2) |
C7—O4 | 1.3522 (18) | | |
| | | |
N2—C1—C2 | 122.10 (13) | C7—C8—H8 | 119.9 |
N2—C1—C5 | 118.49 (12) | C9—C8—H8 | 119.9 |
C2—C1—C5 | 119.41 (13) | O5—C9—C8 | 123.43 (13) |
N1—C2—C1 | 121.25 (14) | O5—C9—C10 | 116.42 (14) |
N1—C2—H2 | 119.4 | C8—C9—C10 | 120.13 (13) |
C1—C2—H2 | 119.4 | C11—C10—C9 | 119.41 (14) |
N1—C3—C4 | 121.73 (14) | C11—C10—H10 | 120.3 |
N1—C3—H3 | 119.1 | C9—C10—H10 | 120.3 |
C4—C3—H3 | 119.1 | C10—C11—C6 | 122.09 (12) |
N2—C4—C3 | 122.04 (15) | C10—C11—H11 | 119.0 |
N2—C4—H4 | 119.0 | C6—C11—H11 | 119.0 |
C3—C4—H4 | 119.0 | O3—C12—O2 | 122.22 (14) |
O1—C5—N3 | 123.08 (15) | O3—C12—C6 | 123.80 (13) |
O1—C5—C1 | 119.01 (12) | O2—C12—C6 | 113.97 (14) |
N3—C5—C1 | 117.90 (14) | C2—N1—C3 | 116.81 (12) |
C11—C6—C7 | 117.91 (13) | C4—N2—C1 | 116.06 (12) |
C11—C6—C12 | 121.36 (12) | C5—N3—H3A | 120.4 (12) |
C7—C6—C12 | 120.70 (13) | C5—N3—H3B | 119.7 (14) |
O4—C7—C8 | 117.76 (12) | H3A—N3—H3B | 119.9 (19) |
O4—C7—C6 | 121.92 (14) | C12—O2—H2A | 113.7 (17) |
C8—C7—C6 | 120.31 (13) | C7—O4—H4A | 107.9 (14) |
C7—C8—C9 | 120.15 (12) | C9—O5—H5A | 111.5 (15) |
Crystal data top
C7H6O4·C5H5N3O | F(000) = 576 |
Mr = 277.24 | Dx = 1.558 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.0839 (15) Å | Cell parameters from 4900 reflections |
b = 5.0936 (8) Å | θ = 2.5–25.8° |
c = 23.335 (3) Å | µ = 0.12 mm−1 |
β = 99.605 (8)° | T = 293 K |
V = 1181.8 (3) Å3 | Needle, yellow |
Z = 4 | 0.90 × 0.21 × 0.08 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 1827 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.075 |
φ and ω scans | θmax = 26.5°, θmin = 2.5° |
Absorption correction: multi-scan Bruker AXS SADABS program | h = −12→12 |
Tmin = 0.897, Tmax = 0.990 | k = −6→6 |
16225 measured reflections | l = −29→25 |
2413 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.137 | w = 1/[σ2(Fo2) + (0.0771P)2 + 0.1214P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
2413 reflections | Δρmax = 0.20 e Å−3 |
181 parameters | Δρmin = −0.28 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O3 | 0.13875 (14) | 0.7030 (3) | 0.46846 (5) | 0.0475 (4) | |
O2 | 0.30423 (13) | 0.8732 (3) | 0.42840 (5) | 0.0449 (4) | |
H2A | 0.316898 | 1.020995 | 0.463937 | 0.067* | |
O4 | 0.00526 (14) | 0.3121 (3) | 0.42031 (6) | 0.0536 (4) | |
H4A | 0.036498 | 0.440754 | 0.448681 | 0.080* | |
O5 | 0.34566 (12) | 0.7251 (2) | 0.32621 (5) | 0.0412 (3) | |
H5A | 0.355216 | 0.823317 | 0.360285 | 0.062* | |
C6 | 0.17650 (16) | 0.5352 (3) | 0.37772 (6) | 0.0324 (4) | |
C7 | 0.07447 (17) | 0.3420 (3) | 0.37611 (7) | 0.0367 (4) | |
C8 | 0.04381 (19) | 0.1764 (4) | 0.32889 (8) | 0.0431 (4) | |
H8 | −0.023703 | 0.051356 | 0.327956 | 0.052* | |
C9 | 0.11341 (19) | 0.1974 (4) | 0.28337 (8) | 0.0425 (4) | |
H9 | 0.092438 | 0.085357 | 0.251690 | 0.051* | |
C10 | 0.21406 (18) | 0.3816 (4) | 0.28365 (7) | 0.0396 (4) | |
H10 | 0.260454 | 0.391854 | 0.252463 | 0.047* | |
C11 | 0.24579 (17) | 0.5503 (3) | 0.33011 (7) | 0.0335 (4) | |
C12 | 0.20399 (17) | 0.7087 (3) | 0.42845 (7) | 0.0343 (4) | |
O1 | 0.34994 (13) | 0.2781 (3) | 0.00680 (5) | 0.0463 (4) | |
N1 | 0.48221 (16) | −0.3132 (3) | 0.12588 (6) | 0.0422 (4) | |
N2 | 0.29239 (16) | 0.0639 (3) | 0.14428 (6) | 0.0423 (4) | |
N3 | 0.18861 (16) | 0.3917 (3) | 0.05846 (7) | 0.0474 (4) | |
H3A | 0.155702 | 0.360569 | 0.090564 | 0.057* | |
H3B | 0.152092 | 0.514399 | 0.031824 | 0.057* | |
C1 | 0.34313 (17) | 0.0529 (3) | 0.09513 (7) | 0.0337 (4) | |
C2 | 0.43729 (18) | −0.1328 (3) | 0.08613 (7) | 0.0377 (4) | |
H2 | 0.470305 | −0.131641 | 0.051222 | 0.045* | |
C3 | 0.4328 (2) | −0.3009 (4) | 0.17479 (8) | 0.0435 (5) | |
H3 | 0.461919 | −0.422502 | 0.203905 | 0.052* | |
C4 | 0.3394 (2) | −0.1136 (4) | 0.18437 (8) | 0.0467 (5) | |
H4 | 0.308596 | −0.111957 | 0.219793 | 0.056* | |
C5 | 0.29339 (17) | 0.2522 (3) | 0.04951 (7) | 0.0352 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3 | 0.0548 (8) | 0.0447 (8) | 0.0471 (7) | −0.0127 (6) | 0.0200 (6) | −0.0100 (6) |
O2 | 0.0495 (8) | 0.0427 (7) | 0.0447 (7) | −0.0166 (6) | 0.0143 (6) | −0.0111 (5) |
O4 | 0.0593 (9) | 0.0538 (9) | 0.0510 (8) | −0.0241 (7) | 0.0191 (7) | −0.0067 (6) |
O5 | 0.0472 (7) | 0.0363 (7) | 0.0422 (7) | −0.0095 (6) | 0.0135 (6) | −0.0035 (5) |
C6 | 0.0347 (9) | 0.0257 (9) | 0.0354 (9) | 0.0018 (7) | 0.0015 (7) | 0.0016 (6) |
C7 | 0.0366 (9) | 0.0313 (9) | 0.0414 (9) | −0.0012 (7) | 0.0042 (7) | 0.0037 (7) |
C8 | 0.0417 (10) | 0.0330 (10) | 0.0520 (11) | −0.0082 (8) | 0.0004 (8) | −0.0018 (7) |
C9 | 0.0478 (11) | 0.0326 (10) | 0.0442 (10) | 0.0009 (8) | −0.0011 (8) | −0.0075 (7) |
C10 | 0.0440 (10) | 0.0368 (10) | 0.0379 (9) | 0.0027 (8) | 0.0070 (8) | −0.0027 (7) |
C11 | 0.0348 (9) | 0.0260 (8) | 0.0391 (9) | 0.0022 (7) | 0.0040 (7) | 0.0027 (6) |
C12 | 0.0364 (9) | 0.0292 (9) | 0.0377 (9) | −0.0004 (7) | 0.0070 (7) | 0.0017 (6) |
O1 | 0.0544 (8) | 0.0446 (8) | 0.0433 (7) | 0.0161 (6) | 0.0182 (6) | 0.0118 (6) |
N1 | 0.0440 (9) | 0.0358 (8) | 0.0468 (9) | 0.0067 (7) | 0.0077 (7) | 0.0038 (6) |
N2 | 0.0490 (9) | 0.0394 (9) | 0.0413 (8) | 0.0063 (7) | 0.0155 (7) | 0.0026 (6) |
N3 | 0.0468 (9) | 0.0466 (10) | 0.0521 (9) | 0.0164 (8) | 0.0173 (7) | 0.0122 (7) |
C1 | 0.0338 (9) | 0.0312 (9) | 0.0364 (8) | 0.0002 (7) | 0.0066 (7) | −0.0001 (7) |
C2 | 0.0412 (10) | 0.0367 (9) | 0.0365 (9) | 0.0019 (8) | 0.0104 (7) | 0.0006 (7) |
C3 | 0.0500 (11) | 0.0384 (10) | 0.0418 (10) | 0.0030 (8) | 0.0064 (8) | 0.0069 (7) |
C4 | 0.0584 (12) | 0.0461 (11) | 0.0392 (10) | 0.0058 (9) | 0.0183 (9) | 0.0060 (8) |
C5 | 0.0360 (9) | 0.0307 (9) | 0.0391 (9) | 0.0022 (7) | 0.0069 (7) | −0.0001 (7) |
Geometric parameters (Å, º) top
O3—C12 | 1.2291 (19) | C10—H10 | 0.9300 |
O2—C12 | 1.313 (2) | O1—C5 | 1.2352 (19) |
O2—H2A | 1.1114 | N1—C3 | 1.321 (2) |
O4—C7 | 1.347 (2) | N1—C2 | 1.330 (2) |
O4—H4A | 0.9473 | N2—C4 | 1.330 (2) |
O5—C11 | 1.358 (2) | N2—C1 | 1.333 (2) |
O5—H5A | 0.9309 | N3—C5 | 1.319 (2) |
C6—C11 | 1.410 (2) | N3—H3A | 0.8828 |
C6—C7 | 1.420 (2) | N3—H3B | 0.9144 |
C6—C12 | 1.466 (2) | C1—C2 | 1.381 (2) |
C7—C8 | 1.381 (2) | C1—C5 | 1.496 (2) |
C8—C9 | 1.371 (2) | C2—H2 | 0.9300 |
C8—H8 | 0.9300 | C3—C4 | 1.385 (3) |
C9—C10 | 1.381 (3) | C3—H3 | 0.9300 |
C9—H9 | 0.9300 | C4—H4 | 0.9300 |
C10—C11 | 1.378 (2) | | |
| | | |
C12—O2—H2A | 115.1 | O3—C12—C6 | 123.09 (15) |
C7—O4—H4A | 107.6 | O2—C12—C6 | 115.20 (14) |
C11—O5—H5A | 105.5 | C3—N1—C2 | 115.85 (15) |
C11—C6—C7 | 117.97 (14) | C4—N2—C1 | 115.72 (15) |
C11—C6—C12 | 123.48 (15) | C5—N3—H3A | 117.5 |
C7—C6—C12 | 118.55 (14) | C5—N3—H3B | 120.2 |
O4—C7—C8 | 117.80 (16) | H3A—N3—H3B | 122.3 |
O4—C7—C6 | 121.59 (15) | N2—C1—C2 | 122.16 (15) |
C8—C7—C6 | 120.61 (16) | N2—C1—C5 | 116.91 (14) |
C9—C8—C7 | 119.67 (17) | C2—C1—C5 | 120.93 (15) |
C9—C8—H8 | 120.2 | N1—C2—C1 | 121.99 (15) |
C7—C8—H8 | 120.2 | N1—C2—H2 | 119.0 |
C8—C9—C10 | 121.32 (16) | C1—C2—H2 | 119.0 |
C8—C9—H9 | 119.3 | N1—C3—C4 | 122.49 (16) |
C10—C9—H9 | 119.3 | N1—C3—H3 | 118.8 |
C11—C10—C9 | 120.07 (16) | C4—C3—H3 | 118.8 |
C11—C10—H10 | 120.0 | N2—C4—C3 | 121.77 (16) |
C9—C10—H10 | 120.0 | N2—C4—H4 | 119.1 |
O5—C11—C10 | 115.66 (15) | C3—C4—H4 | 119.1 |
O5—C11—C6 | 123.99 (14) | O1—C5—N3 | 124.09 (16) |
C10—C11—C6 | 120.35 (15) | O1—C5—C1 | 120.10 (14) |
O3—C12—O2 | 121.70 (15) | N3—C5—C1 | 115.81 (15) |
| | | |
C11—C6—C7—O4 | 178.87 (15) | C7—C6—C12—O3 | −3.5 (2) |
C12—C6—C7—O4 | −1.4 (2) | C11—C6—C12—O2 | −3.7 (2) |
C11—C6—C7—C8 | −0.6 (2) | C7—C6—C12—O2 | 176.58 (14) |
C12—C6—C7—C8 | 179.15 (15) | C4—N2—C1—C2 | 0.7 (3) |
O4—C7—C8—C9 | −178.93 (16) | C4—N2—C1—C5 | −179.28 (16) |
C6—C7—C8—C9 | 0.6 (3) | C3—N1—C2—C1 | −1.1 (3) |
C7—C8—C9—C10 | −0.1 (3) | N2—C1—C2—N1 | 0.5 (3) |
C8—C9—C10—C11 | −0.4 (3) | C5—C1—C2—N1 | −179.47 (15) |
C9—C10—C11—O5 | −179.70 (15) | C2—N1—C3—C4 | 0.4 (3) |
C9—C10—C11—C6 | 0.4 (2) | C1—N2—C4—C3 | −1.4 (3) |
C7—C6—C11—O5 | −179.77 (15) | N1—C3—C4—N2 | 0.8 (3) |
C12—C6—C11—O5 | 0.5 (2) | N2—C1—C5—O1 | 169.36 (16) |
C7—C6—C11—C10 | 0.2 (2) | C2—C1—C5—O1 | −10.6 (2) |
C12—C6—C11—C10 | −179.61 (16) | N2—C1—C5—N3 | −10.6 (2) |
C11—C6—C12—O3 | 176.31 (16) | C2—C1—C5—N3 | 169.37 (16) |
Crystal data top
C7H6O4·C5H5N3O | F(000) = 576 |
Mr = 277.24 | Dx = 1.506 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 5.0262 (3) Å | Cell parameters from 4461 reflections |
b = 25.2701 (11) Å | θ = 2.3–27.0° |
c = 9.7106 (5) Å | µ = 0.12 mm−1 |
β = 97.492 (3)° | T = 296 K |
V = 1222.84 (11) Å3 | Block, colorless |
Z = 4 | 0.23 × 0.18 × 0.16 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 2259 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.021 |
φ and ω scans | θmax = 27.1°, θmin = 2.3° |
Absorption correction: multi-scan Bruker AXS SADABS program | h = −5→6 |
Tmin = 0.973, Tmax = 0.981 | k = −31→32 |
10147 measured reflections | l = −11→12 |
2677 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.0581P)2 + 0.4176P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
2677 reflections | Δρmax = 0.15 e Å−3 |
201 parameters | Δρmin = −0.26 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.7152 (3) | 0.07063 (6) | 0.81374 (16) | 0.0311 (3) | |
C2 | 0.8607 (4) | 0.09207 (6) | 0.71523 (17) | 0.0375 (4) | |
H2 | 0.838594 | 0.127638 | 0.691904 | 0.045* | |
C3 | 1.0541 (4) | 0.01251 (7) | 0.69110 (18) | 0.0407 (4) | |
H3 | 1.170765 | −0.009175 | 0.649916 | 0.049* | |
C4 | 0.9104 (4) | −0.00895 (7) | 0.78978 (19) | 0.0439 (4) | |
H4 | 0.933789 | −0.044489 | 0.813136 | 0.053* | |
C5 | 0.5225 (3) | 0.10536 (6) | 0.87752 (16) | 0.0344 (4) | |
C6 | 0.7002 (3) | 0.17708 (6) | 0.26205 (15) | 0.0296 (3) | |
C7 | 0.5911 (3) | 0.22364 (6) | 0.30452 (16) | 0.0337 (4) | |
H7 | 0.635610 | 0.256041 | 0.268281 | 0.040* | |
C8 | 0.4135 (3) | 0.22086 (6) | 0.40251 (16) | 0.0344 (4) | |
C9 | 0.3463 (3) | 0.17281 (6) | 0.45713 (17) | 0.0349 (4) | |
H9 | 0.228667 | 0.171596 | 0.523485 | 0.042* | |
C10 | 0.4554 (3) | 0.12651 (6) | 0.41227 (16) | 0.0337 (4) | |
C11 | 0.6346 (3) | 0.12845 (6) | 0.31483 (17) | 0.0345 (4) | |
H11 | 0.709638 | 0.097492 | 0.285288 | 0.041* | |
C12 | 0.8917 (3) | 0.17874 (6) | 0.15695 (16) | 0.0321 (3) | |
H4A | 0.352 (5) | 0.2936 (10) | 0.412 (3) | 0.064 (7)* | |
H5A | 0.269 (6) | 0.0808 (11) | 0.523 (3) | 0.089 (9)* | |
H3A | 0.432 (4) | 0.0503 (9) | 1.004 (2) | 0.048 (6)* | |
H3B | 0.283 (4) | 0.1053 (8) | 1.014 (2) | 0.051 (6)* | |
H2A | 1.059 (5) | 0.2280 (9) | 0.055 (3) | 0.069 (7)* | |
N2 | 0.7391 (3) | 0.01997 (5) | 0.85234 (15) | 0.0382 (3) | |
N1 | 1.0315 (3) | 0.06284 (6) | 0.65319 (14) | 0.0387 (3) | |
N3 | 0.3986 (3) | 0.08439 (6) | 0.97651 (15) | 0.0396 (4) | |
O1 | 0.4864 (3) | 0.15084 (5) | 0.83340 (15) | 0.0544 (4) | |
O3 | 0.9916 (3) | 0.13964 (5) | 0.11251 (13) | 0.0440 (3) | |
O2 | 0.9400 (3) | 0.22726 (5) | 0.11761 (14) | 0.0492 (4) | |
O4 | 0.2972 (3) | 0.26537 (5) | 0.44612 (15) | 0.0526 (4) | |
O5 | 0.3948 (3) | 0.07791 (5) | 0.46020 (14) | 0.0490 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0325 (8) | 0.0297 (7) | 0.0334 (7) | −0.0010 (6) | 0.0129 (6) | −0.0012 (6) |
C2 | 0.0427 (10) | 0.0313 (8) | 0.0423 (9) | 0.0015 (7) | 0.0198 (7) | 0.0036 (6) |
C3 | 0.0461 (10) | 0.0354 (9) | 0.0454 (9) | 0.0041 (7) | 0.0238 (8) | −0.0013 (7) |
C4 | 0.0562 (11) | 0.0288 (8) | 0.0521 (10) | 0.0042 (7) | 0.0280 (9) | 0.0038 (7) |
C5 | 0.0379 (9) | 0.0291 (8) | 0.0389 (8) | −0.0003 (6) | 0.0156 (7) | −0.0029 (6) |
C6 | 0.0287 (8) | 0.0317 (8) | 0.0308 (7) | 0.0005 (6) | 0.0131 (6) | 0.0002 (6) |
C7 | 0.0369 (9) | 0.0288 (7) | 0.0398 (8) | −0.0016 (6) | 0.0214 (7) | 0.0005 (6) |
C8 | 0.0390 (9) | 0.0301 (8) | 0.0385 (8) | −0.0013 (6) | 0.0217 (7) | −0.0048 (6) |
C9 | 0.0376 (9) | 0.0363 (8) | 0.0353 (8) | −0.0043 (7) | 0.0219 (7) | −0.0022 (6) |
C10 | 0.0380 (9) | 0.0314 (8) | 0.0344 (8) | −0.0029 (6) | 0.0151 (7) | 0.0032 (6) |
C11 | 0.0379 (9) | 0.0301 (8) | 0.0391 (8) | 0.0037 (6) | 0.0190 (7) | 0.0008 (6) |
C12 | 0.0318 (8) | 0.0333 (8) | 0.0343 (8) | 0.0024 (6) | 0.0157 (6) | 0.0014 (6) |
N2 | 0.0459 (9) | 0.0301 (7) | 0.0430 (8) | 0.0012 (6) | 0.0223 (6) | 0.0023 (6) |
N1 | 0.0429 (8) | 0.0365 (7) | 0.0413 (7) | −0.0001 (6) | 0.0224 (6) | 0.0016 (6) |
N3 | 0.0444 (9) | 0.0351 (8) | 0.0445 (8) | 0.0036 (6) | 0.0257 (7) | 0.0003 (6) |
O1 | 0.0710 (10) | 0.0314 (6) | 0.0697 (9) | 0.0100 (6) | 0.0430 (7) | 0.0072 (6) |
O3 | 0.0479 (8) | 0.0393 (6) | 0.0514 (7) | 0.0056 (5) | 0.0308 (6) | −0.0020 (5) |
O2 | 0.0591 (9) | 0.0375 (7) | 0.0609 (8) | 0.0049 (6) | 0.0452 (7) | 0.0086 (6) |
O4 | 0.0685 (10) | 0.0295 (6) | 0.0716 (9) | −0.0006 (6) | 0.0538 (8) | −0.0044 (6) |
O5 | 0.0643 (9) | 0.0313 (6) | 0.0594 (8) | −0.0018 (6) | 0.0380 (7) | 0.0068 (5) |
Geometric parameters (Å, º) top
C1—N2 | 1.335 (2) | C7—H7 | 0.9300 |
C1—C2 | 1.388 (2) | C8—O4 | 1.3601 (18) |
C1—C5 | 1.499 (2) | C8—C9 | 1.384 (2) |
C2—N1 | 1.335 (2) | C9—C10 | 1.386 (2) |
C2—H2 | 0.9300 | C9—H9 | 0.9300 |
C3—N1 | 1.325 (2) | C10—O5 | 1.3620 (18) |
C3—C4 | 1.384 (2) | C10—C11 | 1.389 (2) |
C3—H3 | 0.9300 | C11—H11 | 0.9300 |
C4—N2 | 1.334 (2) | C12—O3 | 1.2128 (19) |
C4—H4 | 0.9300 | C12—O2 | 1.3162 (19) |
C5—O1 | 1.232 (2) | N3—H3A | 0.91 (2) |
C5—N3 | 1.323 (2) | N3—H3B | 0.90 (2) |
C6—C7 | 1.384 (2) | O2—H2A | 0.91 (3) |
C6—C11 | 1.388 (2) | O4—H4A | 0.85 (3) |
C6—C12 | 1.4920 (19) | O5—H5A | 0.94 (3) |
C7—C8 | 1.389 (2) | | |
| | | |
N2—C1—C2 | 122.11 (14) | O4—C8—C7 | 120.81 (14) |
N2—C1—C5 | 119.01 (13) | C9—C8—C7 | 121.16 (14) |
C2—C1—C5 | 118.88 (14) | C8—C9—C10 | 119.58 (13) |
N1—C2—C1 | 121.54 (15) | C8—C9—H9 | 120.2 |
N1—C2—H2 | 119.2 | C10—C9—H9 | 120.2 |
C1—C2—H2 | 119.2 | O5—C10—C9 | 122.56 (13) |
N1—C3—C4 | 122.34 (15) | O5—C10—C11 | 117.29 (14) |
N1—C3—H3 | 118.8 | C9—C10—C11 | 120.15 (14) |
C4—C3—H3 | 118.8 | C6—C11—C10 | 119.29 (14) |
N2—C4—C3 | 121.79 (15) | C6—C11—H11 | 120.4 |
N2—C4—H4 | 119.1 | C10—C11—H11 | 120.4 |
C3—C4—H4 | 119.1 | O3—C12—O2 | 123.73 (14) |
O1—C5—N3 | 124.39 (15) | O3—C12—C6 | 123.66 (14) |
O1—C5—C1 | 118.44 (14) | O2—C12—C6 | 112.60 (13) |
N3—C5—C1 | 117.16 (14) | C4—N2—C1 | 115.93 (14) |
C7—C6—C11 | 121.35 (13) | C3—N1—C2 | 116.28 (13) |
C7—C6—C12 | 119.75 (13) | C5—N3—H3A | 120.2 (13) |
C11—C6—C12 | 118.90 (13) | C5—N3—H3B | 116.8 (13) |
C6—C7—C8 | 118.46 (14) | H3A—N3—H3B | 123.0 (19) |
C6—C7—H7 | 120.8 | C12—O2—H2A | 112.1 (15) |
C8—C7—H7 | 120.8 | C8—O4—H4A | 113.5 (17) |
O4—C8—C9 | 118.03 (13) | C10—O5—H5A | 110.7 (17) |
Crystal data top
C10H10O4·C5H5N3O | Z = 2 |
Mr = 317.30 | F(000) = 332 |
Triclinic, P1 | Dx = 1.397 Mg m−3 |
a = 7.4159 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.1690 (7) Å | Cell parameters from 5994 reflections |
c = 11.0335 (8) Å | θ = 2.5–26.4° |
α = 70.471 (3)° | µ = 0.11 mm−1 |
β = 76.142 (3)° | T = 296 K |
γ = 78.253 (4)° | Block, yellow |
V = 754.40 (9) Å3 | 0.23 × 0.19 × 0.17 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 2632 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.024 |
φ and ω scans | θmax = 26.5°, θmin = 2.0° |
Absorption correction: multi-scan Bruker AXS SADABS program | h = −9→9 |
Tmin = 0.976, Tmax = 0.982 | k = −12→12 |
11332 measured reflections | l = −13→13 |
3118 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.036 | w = 1/[σ2(Fo2) + (0.0571P)2 + 0.1265P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.107 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.23 e Å−3 |
3118 reflections | Δρmin = −0.15 e Å−3 |
226 parameters | Extinction correction: SHELXL-2016/6 (Sheldrick 2016), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.036 (4) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.18688 (16) | 0.24623 (12) | 0.14500 (12) | 0.0399 (3) | |
C2 | 0.22192 (18) | 0.12192 (13) | 0.24235 (13) | 0.0452 (3) | |
H2 | 0.334380 | 0.102276 | 0.272327 | 0.054* | |
C3 | −0.0563 (2) | 0.06323 (15) | 0.24598 (15) | 0.0591 (4) | |
H3 | −0.144709 | 0.000915 | 0.278231 | 0.071* | |
C4 | −0.0922 (2) | 0.18745 (16) | 0.14933 (16) | 0.0607 (4) | |
H4 | −0.204526 | 0.206736 | 0.119220 | 0.073* | |
C5 | 0.32803 (16) | 0.34795 (12) | 0.08814 (12) | 0.0418 (3) | |
C6 | 0.05299 (18) | 0.56029 (12) | 0.28478 (12) | 0.0424 (3) | |
C7 | 0.15110 (17) | 0.44463 (12) | 0.36515 (12) | 0.0415 (3) | |
H7 | 0.274275 | 0.447619 | 0.368477 | 0.050* | |
C8 | 0.06773 (17) | 0.32654 (12) | 0.43929 (11) | 0.0399 (3) | |
C9 | −0.11862 (17) | 0.32108 (13) | 0.43606 (12) | 0.0432 (3) | |
C10 | −0.21494 (19) | 0.43527 (15) | 0.35648 (14) | 0.0517 (3) | |
H10 | −0.338340 | 0.432739 | 0.353296 | 0.062* | |
C11 | −0.13009 (19) | 0.55336 (14) | 0.28144 (13) | 0.0498 (3) | |
H11 | −0.196970 | 0.628949 | 0.228142 | 0.060* | |
C12 | 0.1413 (2) | 0.68512 (13) | 0.20393 (13) | 0.0469 (3) | |
H12 | 0.069749 | 0.755270 | 0.149320 | 0.056* | |
C13 | 0.3111 (2) | 0.70931 (14) | 0.19984 (14) | 0.0523 (3) | |
H13 | 0.384823 | 0.641873 | 0.254754 | 0.063* | |
C14 | 0.38923 (19) | 0.83643 (13) | 0.11359 (13) | 0.0481 (3) | |
C15 | 0.3492 (2) | 0.20444 (17) | 0.51565 (17) | 0.0642 (4) | |
H15A | 0.416455 | 0.222256 | 0.427075 | 0.096* | |
H15B | 0.397479 | 0.113400 | 0.567482 | 0.096* | |
H15C | 0.364230 | 0.275254 | 0.550800 | 0.096* | |
H2A | 0.607 (4) | 0.9356 (18) | 0.071 (3) | 0.198 (15)* | |
H3A | 0.366 (2) | 0.5282 (19) | −0.0454 (17) | 0.066 (5)* | |
H5A | −0.139 (3) | 0.145 (2) | 0.5552 (19) | 0.076 (6)* | |
H3B | 0.174 (3) | 0.4702 (18) | −0.0283 (17) | 0.064 (5)* | |
N1 | 0.02881 (15) | 0.28023 (12) | 0.09808 (11) | 0.0517 (3) | |
N2 | 0.09973 (16) | 0.02950 (11) | 0.29450 (11) | 0.0521 (3) | |
N3 | 0.28469 (18) | 0.46044 (12) | −0.00823 (12) | 0.0532 (3) | |
O1 | 0.47332 (13) | 0.32349 (10) | 0.13172 (10) | 0.0595 (3) | |
O2 | 0.55090 (16) | 0.85065 (11) | 0.12432 (12) | 0.0690 (3) | |
O3 | 0.29722 (15) | 0.92710 (10) | 0.03279 (10) | 0.0599 (3) | |
O4 | 0.15490 (12) | 0.20803 (9) | 0.51800 (10) | 0.0524 (3) | |
O5 | −0.20720 (14) | 0.20744 (11) | 0.50558 (10) | 0.0575 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0382 (6) | 0.0369 (6) | 0.0408 (6) | −0.0046 (5) | −0.0070 (5) | −0.0071 (5) |
C2 | 0.0433 (6) | 0.0393 (6) | 0.0492 (7) | −0.0059 (5) | −0.0138 (5) | −0.0049 (5) |
C3 | 0.0523 (8) | 0.0525 (8) | 0.0651 (9) | −0.0216 (6) | −0.0134 (7) | 0.0022 (7) |
C4 | 0.0463 (7) | 0.0597 (8) | 0.0687 (9) | −0.0168 (6) | −0.0213 (7) | 0.0032 (7) |
C5 | 0.0380 (6) | 0.0382 (6) | 0.0443 (6) | −0.0056 (5) | −0.0068 (5) | −0.0064 (5) |
C6 | 0.0497 (7) | 0.0373 (6) | 0.0368 (6) | −0.0113 (5) | −0.0045 (5) | −0.0061 (5) |
C7 | 0.0381 (6) | 0.0402 (6) | 0.0438 (6) | −0.0108 (5) | −0.0053 (5) | −0.0079 (5) |
C8 | 0.0391 (6) | 0.0372 (6) | 0.0389 (6) | −0.0073 (5) | −0.0059 (5) | −0.0053 (5) |
C9 | 0.0421 (6) | 0.0422 (6) | 0.0414 (6) | −0.0136 (5) | −0.0061 (5) | −0.0041 (5) |
C10 | 0.0419 (7) | 0.0541 (8) | 0.0536 (8) | −0.0128 (6) | −0.0152 (6) | −0.0010 (6) |
C11 | 0.0517 (7) | 0.0448 (7) | 0.0459 (7) | −0.0077 (6) | −0.0155 (6) | 0.0005 (5) |
C12 | 0.0574 (8) | 0.0366 (6) | 0.0414 (6) | −0.0109 (5) | −0.0063 (5) | −0.0042 (5) |
C13 | 0.0559 (8) | 0.0370 (6) | 0.0544 (8) | −0.0117 (6) | −0.0076 (6) | −0.0001 (5) |
C14 | 0.0526 (7) | 0.0359 (6) | 0.0504 (7) | −0.0113 (5) | −0.0042 (6) | −0.0068 (5) |
C15 | 0.0425 (7) | 0.0569 (8) | 0.0785 (10) | −0.0081 (6) | −0.0180 (7) | 0.0041 (7) |
N1 | 0.0445 (6) | 0.0476 (6) | 0.0548 (6) | −0.0118 (5) | −0.0158 (5) | 0.0032 (5) |
N2 | 0.0542 (7) | 0.0406 (6) | 0.0541 (7) | −0.0116 (5) | −0.0133 (5) | 0.0006 (5) |
N3 | 0.0478 (6) | 0.0439 (6) | 0.0592 (7) | −0.0147 (5) | −0.0175 (5) | 0.0061 (5) |
O1 | 0.0438 (5) | 0.0533 (6) | 0.0709 (6) | −0.0141 (4) | −0.0195 (5) | 0.0058 (5) |
O2 | 0.0580 (6) | 0.0487 (6) | 0.0860 (8) | −0.0211 (5) | −0.0164 (5) | 0.0082 (5) |
O3 | 0.0686 (7) | 0.0449 (5) | 0.0594 (6) | −0.0203 (5) | −0.0159 (5) | 0.0032 (4) |
O4 | 0.0405 (5) | 0.0416 (5) | 0.0623 (6) | −0.0102 (4) | −0.0132 (4) | 0.0062 (4) |
O5 | 0.0467 (5) | 0.0518 (6) | 0.0634 (6) | −0.0220 (4) | −0.0169 (5) | 0.0100 (5) |
Geometric parameters (Å, º) top
C1—N1 | 1.3295 (16) | C9—O5 | 1.3529 (15) |
C1—C2 | 1.3826 (17) | C9—C10 | 1.3823 (18) |
C1—C5 | 1.5005 (16) | C10—C11 | 1.3846 (19) |
C2—N2 | 1.3307 (17) | C10—H10 | 0.9300 |
C2—H2 | 0.9300 | C11—H11 | 0.9300 |
C3—N2 | 1.3248 (18) | C12—C13 | 1.319 (2) |
C3—C4 | 1.379 (2) | C12—H12 | 0.9300 |
C3—H3 | 0.9300 | C13—C14 | 1.4598 (17) |
C4—N1 | 1.3269 (18) | C13—H13 | 0.9300 |
C4—H4 | 0.9300 | C14—O3 | 1.2635 (17) |
C5—O1 | 1.2301 (15) | C14—O2 | 1.2737 (18) |
C5—N3 | 1.3203 (16) | C15—O4 | 1.4280 (16) |
C6—C11 | 1.3836 (19) | C15—H15A | 0.9600 |
C6—C7 | 1.4009 (17) | C15—H15B | 0.9600 |
C6—C12 | 1.4619 (17) | C15—H15C | 0.9600 |
C7—C8 | 1.3772 (16) | N3—H3A | 0.930 (19) |
C7—H7 | 0.9300 | N3—H3B | 0.880 (18) |
C8—O4 | 1.3698 (14) | O2—H2A | 0.9802 (10) |
C8—C9 | 1.4036 (17) | O5—H5A | 0.86 (2) |
| | | |
N1—C1—C2 | 121.80 (11) | C9—C10—H10 | 119.6 |
N1—C1—C5 | 117.56 (10) | C11—C10—H10 | 119.6 |
C2—C1—C5 | 120.64 (11) | C6—C11—C10 | 120.81 (12) |
N2—C2—C1 | 122.04 (12) | C6—C11—H11 | 119.6 |
N2—C2—H2 | 119.0 | C10—C11—H11 | 119.6 |
C1—C2—H2 | 119.0 | C13—C12—C6 | 127.23 (13) |
N2—C3—C4 | 122.35 (13) | C13—C12—H12 | 116.4 |
N2—C3—H3 | 118.8 | C6—C12—H12 | 116.4 |
C4—C3—H3 | 118.8 | C12—C13—C14 | 123.42 (13) |
N1—C4—C3 | 121.89 (13) | C12—C13—H13 | 118.3 |
N1—C4—H4 | 119.1 | C14—C13—H13 | 118.3 |
C3—C4—H4 | 119.1 | O3—C14—O2 | 122.61 (12) |
O1—C5—N3 | 124.25 (12) | O3—C14—C13 | 120.17 (13) |
O1—C5—C1 | 119.89 (11) | O2—C14—C13 | 117.21 (12) |
N3—C5—C1 | 115.86 (11) | O4—C15—H15A | 109.5 |
C11—C6—C7 | 118.47 (11) | O4—C15—H15B | 109.5 |
C11—C6—C12 | 120.15 (12) | H15A—C15—H15B | 109.5 |
C7—C6—C12 | 121.36 (12) | O4—C15—H15C | 109.5 |
C8—C7—C6 | 120.94 (11) | H15A—C15—H15C | 109.5 |
C8—C7—H7 | 119.5 | H15B—C15—H15C | 109.5 |
C6—C7—H7 | 119.5 | C4—N1—C1 | 116.11 (11) |
O4—C8—C7 | 124.61 (11) | C3—N2—C2 | 115.79 (11) |
O4—C8—C9 | 115.26 (10) | C5—N3—H3A | 119.4 (10) |
C7—C8—C9 | 120.13 (11) | C5—N3—H3B | 116.7 (11) |
O5—C9—C10 | 118.40 (11) | H3A—N3—H3B | 123.6 (15) |
O5—C9—C8 | 122.79 (11) | C14—O2—H2A | 120.2 (19) |
C10—C9—C8 | 118.79 (11) | C8—O4—C15 | 117.07 (10) |
C9—C10—C11 | 120.85 (12) | C9—O5—H5A | 111.2 (13) |
Crystal data top
C7H7O3S·C5H6N3O | Z = 4 |
Mr = 295.31 | F(000) = 616 |
Triclinic, P1 | Dx = 1.468 Mg m−3 |
a = 7.6458 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.9985 (11) Å | Cell parameters from 4207 reflections |
c = 18.027 (2) Å | θ = 2.3–26.0° |
α = 103.727 (5)° | µ = 0.26 mm−1 |
β = 92.711 (6)° | T = 296 K |
γ = 91.656 (5)° | Block, yellow |
V = 1336.1 (3) Å3 | 0.12 × 0.10 × 0.08 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 3492 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.052 |
φ and ω scans | θmax = 26.5°, θmin = 2.1° |
Absorption correction: multi-scan Bruker AXS SADABS program | h = −9→9 |
Tmin = 0.970, Tmax = 0.980 | k = −12→12 |
20584 measured reflections | l = −22→22 |
5502 independent reflections | |
Refinement top
Refinement on F2 | 36 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.163 | w = 1/[σ2(Fo2) + (0.0913P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.004 |
5502 reflections | Δρmax = 0.34 e Å−3 |
443 parameters | Δρmin = −0.45 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.8272 (3) | 0.4203 (2) | 0.93810 (13) | 0.0322 (5) | |
C2 | 0.8683 (3) | 0.2905 (2) | 0.89836 (14) | 0.0400 (6) | |
H2 | 0.843656 | 0.213552 | 0.917260 | 0.048* | |
C3 | 0.9811 (3) | 0.3857 (3) | 0.80406 (14) | 0.0431 (6) | |
H3 | 1.032102 | 0.375061 | 0.757293 | 0.052* | |
C4 | 0.9415 (3) | 0.5147 (3) | 0.84624 (15) | 0.0452 (6) | |
H4 | 0.969665 | 0.591772 | 0.828060 | 0.054* | |
C5 | 0.7356 (3) | 0.4359 (2) | 1.01158 (14) | 0.0351 (5) | |
C6 | 0.6610 (3) | 0.9132 (2) | 0.93679 (13) | 0.0343 (5) | |
C7 | 0.6045 (3) | 0.7824 (2) | 0.89799 (14) | 0.0385 (6) | |
H7 | 0.629876 | 0.706753 | 0.917632 | 0.046* | |
C8 | 0.4777 (3) | 0.8733 (3) | 0.80262 (15) | 0.0466 (7) | |
H8 | 0.417108 | 0.860487 | 0.755340 | 0.056* | |
C9 | 0.5323 (4) | 1.0034 (3) | 0.84333 (15) | 0.0477 (7) | |
H9 | 0.504769 | 1.078858 | 0.823841 | 0.057* | |
C10 | 0.7661 (3) | 0.9338 (2) | 1.01163 (14) | 0.0356 (6) | |
C11 | 0.1067 (3) | 0.8432 (2) | 0.68057 (13) | 0.0336 (5) | |
C12 | 0.1879 (3) | 0.9471 (3) | 0.65402 (15) | 0.0457 (6) | |
H12 | 0.150928 | 1.036893 | 0.668330 | 0.055* | |
C13 | 0.3243 (4) | 0.9159 (4) | 0.60612 (17) | 0.0598 (8) | |
H13 | 0.377658 | 0.985716 | 0.587996 | 0.072* | |
C14 | 0.3837 (4) | 0.7839 (4) | 0.58437 (15) | 0.0582 (8) | |
C15 | 0.3004 (4) | 0.6814 (3) | 0.61160 (16) | 0.0551 (8) | |
H15 | 0.337843 | 0.591723 | 0.597425 | 0.066* | |
C16 | 0.1629 (3) | 0.7097 (3) | 0.65928 (15) | 0.0438 (6) | |
H16 | 0.108656 | 0.639700 | 0.676935 | 0.053* | |
C17 | 0.5386 (4) | 0.7521 (5) | 0.5348 (2) | 0.0924 (13) | |
H17A | 0.555697 | 0.823330 | 0.507954 | 0.139* | |
H17B | 0.516536 | 0.665231 | 0.498518 | 0.139* | |
H17C | 0.641912 | 0.747584 | 0.566345 | 0.139* | |
C18 | 0.6133 (3) | 0.3468 (3) | 0.68533 (13) | 0.0350 (5) | |
C19 | 0.6906 (4) | 0.4507 (3) | 0.65800 (15) | 0.0483 (7) | |
H19 | 0.651866 | 0.540099 | 0.671918 | 0.058* | |
C20 | 0.8268 (4) | 0.4199 (4) | 0.60951 (17) | 0.0633 (9) | |
H20 | 0.876908 | 0.489454 | 0.590171 | 0.076* | |
C21 | 0.8902 (4) | 0.2900 (4) | 0.58910 (16) | 0.0623 (9) | |
C22 | 0.8103 (4) | 0.1867 (3) | 0.61726 (16) | 0.0562 (8) | |
H22 | 0.849965 | 0.097603 | 0.603583 | 0.067* | |
C23 | 0.6727 (3) | 0.2141 (3) | 0.66526 (14) | 0.0451 (6) | |
H23 | 0.620806 | 0.144211 | 0.683794 | 0.054* | |
C24 | 1.0444 (4) | 0.2591 (5) | 0.5389 (2) | 0.0976 (14) | |
H24A | 1.019382 | 0.175043 | 0.500676 | 0.146* | |
H24B | 1.146934 | 0.249458 | 0.569722 | 0.146* | |
H24C | 1.064482 | 0.333290 | 0.514512 | 0.146* | |
H1A | 0.965 (4) | 0.187 (3) | 0.8065 (18) | 0.073 (10)* | |
H3A | 0.736 (3) | 0.637 (3) | 1.0254 (13) | 0.038 (7)* | |
H4A | 0.476 (4) | 0.683 (3) | 0.8033 (19) | 0.076 (11)* | |
H6A | 0.760 (3) | 1.132 (3) | 1.0309 (14) | 0.045 (8)* | |
H3B | 0.649 (4) | 0.575 (3) | 1.0871 (16) | 0.052 (8)* | |
H6B | 0.860 (3) | 1.076 (2) | 1.0942 (15) | 0.041 (7)* | |
N1 | 0.9443 (3) | 0.2780 (2) | 0.83212 (13) | 0.0454 (6) | |
N2 | 0.8639 (3) | 0.5313 (2) | 0.91233 (12) | 0.0405 (5) | |
N3 | 0.7020 (3) | 0.5631 (2) | 1.04678 (13) | 0.0396 (5) | |
N4 | 0.5125 (3) | 0.7666 (2) | 0.83154 (13) | 0.0441 (5) | |
N5 | 0.6239 (3) | 1.0236 (2) | 0.91020 (12) | 0.0416 (5) | |
N6 | 0.8067 (3) | 1.0628 (2) | 1.04786 (14) | 0.0419 (5) | |
O1 | 0.6975 (2) | 0.33240 (17) | 1.03446 (10) | 0.0495 (5) | |
O2 | 0.8079 (3) | 0.83300 (17) | 1.03494 (11) | 0.0528 (5) | |
O3A | −0.0083 (9) | 0.8340 (7) | 0.8106 (3) | 0.0674 (18) | 0.630 (10) |
O4A | −0.0957 (7) | 1.0191 (3) | 0.7578 (3) | 0.065 (2) | 0.630 (10) |
O5A | −0.2146 (5) | 0.7931 (6) | 0.7061 (2) | 0.0642 (17) | 0.630 (10) |
O6A | 0.5200 (7) | 0.3700 (8) | 0.8221 (3) | 0.0868 (19) | 0.837 (15) |
O7A | 0.3864 (6) | 0.5167 (5) | 0.7517 (3) | 0.0548 (12) | 0.837 (15) |
O8A | 0.3066 (7) | 0.2789 (4) | 0.7209 (4) | 0.0819 (19) | 0.837 (15) |
O3B | −0.2103 (8) | 0.9111 (15) | 0.7055 (4) | 0.093 (5) | 0.370 (10) |
O4B | −0.076 (2) | 0.7824 (12) | 0.7852 (9) | 0.115 (7) | 0.370 (10) |
O5B | 0.0144 (14) | 1.0111 (8) | 0.7994 (5) | 0.081 (3) | 0.370 (10) |
O6B | 0.453 (6) | 0.310 (4) | 0.802 (2) | 0.109 (13) | 0.163 (15) |
O7B | 0.452 (5) | 0.522 (3) | 0.779 (2) | 0.102 (12) | 0.163 (15) |
O8B | 0.291 (3) | 0.340 (5) | 0.7007 (12) | 0.117 (13) | 0.163 (15) |
S1 | −0.06309 (8) | 0.87955 (6) | 0.74478 (3) | 0.0400 (2) | |
S2 | 0.44210 (8) | 0.37959 (6) | 0.74898 (4) | 0.0385 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0284 (11) | 0.0304 (13) | 0.0370 (13) | 0.0007 (9) | −0.0008 (10) | 0.0070 (10) |
C2 | 0.0402 (13) | 0.0328 (14) | 0.0475 (15) | 0.0012 (11) | 0.0062 (12) | 0.0098 (11) |
C3 | 0.0345 (13) | 0.0564 (18) | 0.0382 (14) | 0.0023 (12) | 0.0063 (11) | 0.0099 (13) |
C4 | 0.0518 (16) | 0.0437 (16) | 0.0443 (15) | 0.0012 (12) | 0.0082 (12) | 0.0176 (12) |
C5 | 0.0320 (12) | 0.0303 (13) | 0.0430 (14) | 0.0008 (10) | 0.0015 (10) | 0.0087 (11) |
C6 | 0.0307 (12) | 0.0329 (13) | 0.0411 (13) | 0.0021 (10) | 0.0094 (10) | 0.0105 (11) |
C7 | 0.0367 (13) | 0.0319 (14) | 0.0465 (14) | 0.0036 (10) | 0.0046 (11) | 0.0080 (11) |
C8 | 0.0408 (14) | 0.0558 (18) | 0.0424 (15) | 0.0000 (13) | 0.0009 (12) | 0.0106 (13) |
C9 | 0.0529 (16) | 0.0475 (17) | 0.0474 (16) | 0.0009 (13) | −0.0015 (13) | 0.0213 (13) |
C10 | 0.0356 (12) | 0.0302 (13) | 0.0419 (14) | 0.0011 (10) | 0.0045 (11) | 0.0098 (11) |
C11 | 0.0307 (12) | 0.0330 (13) | 0.0349 (12) | −0.0008 (10) | 0.0000 (10) | 0.0040 (10) |
C12 | 0.0446 (14) | 0.0462 (16) | 0.0476 (15) | −0.0037 (12) | 0.0022 (12) | 0.0143 (12) |
C13 | 0.0442 (16) | 0.083 (2) | 0.0567 (18) | −0.0177 (16) | 0.0024 (14) | 0.0280 (17) |
C14 | 0.0337 (14) | 0.097 (3) | 0.0385 (15) | 0.0005 (15) | 0.0008 (12) | 0.0053 (16) |
C15 | 0.0447 (15) | 0.0591 (19) | 0.0522 (17) | 0.0138 (14) | 0.0005 (13) | −0.0062 (14) |
C16 | 0.0418 (14) | 0.0381 (15) | 0.0489 (15) | 0.0005 (11) | 0.0040 (12) | 0.0052 (12) |
C17 | 0.0476 (19) | 0.167 (4) | 0.057 (2) | 0.008 (2) | 0.0144 (16) | 0.014 (2) |
C18 | 0.0291 (11) | 0.0407 (14) | 0.0327 (12) | −0.0024 (10) | −0.0006 (10) | 0.0050 (11) |
C19 | 0.0458 (15) | 0.0498 (17) | 0.0489 (15) | −0.0104 (12) | 0.0005 (13) | 0.0128 (13) |
C20 | 0.0464 (16) | 0.093 (3) | 0.0536 (18) | −0.0219 (17) | 0.0028 (14) | 0.0258 (17) |
C21 | 0.0325 (14) | 0.112 (3) | 0.0380 (15) | −0.0008 (17) | 0.0022 (12) | 0.0110 (17) |
C22 | 0.0449 (16) | 0.069 (2) | 0.0486 (16) | 0.0180 (15) | 0.0052 (13) | −0.0001 (15) |
C23 | 0.0423 (14) | 0.0457 (16) | 0.0449 (15) | 0.0027 (12) | 0.0036 (12) | 0.0057 (12) |
C24 | 0.0461 (19) | 0.186 (4) | 0.057 (2) | 0.003 (2) | 0.0167 (16) | 0.018 (2) |
N1 | 0.0464 (13) | 0.0373 (13) | 0.0473 (13) | 0.0045 (10) | 0.0067 (10) | −0.0015 (11) |
N2 | 0.0464 (12) | 0.0323 (11) | 0.0449 (12) | 0.0028 (9) | 0.0080 (10) | 0.0120 (9) |
N3 | 0.0463 (13) | 0.0319 (12) | 0.0418 (13) | 0.0042 (10) | 0.0119 (10) | 0.0089 (10) |
N4 | 0.0410 (12) | 0.0419 (14) | 0.0449 (13) | 0.0020 (10) | 0.0058 (10) | 0.0009 (11) |
N5 | 0.0448 (12) | 0.0359 (12) | 0.0467 (12) | −0.0007 (9) | 0.0055 (10) | 0.0148 (10) |
N6 | 0.0479 (13) | 0.0337 (13) | 0.0436 (13) | 0.0004 (10) | −0.0032 (11) | 0.0096 (10) |
O1 | 0.0623 (12) | 0.0329 (10) | 0.0582 (11) | 0.0015 (8) | 0.0193 (9) | 0.0172 (9) |
O2 | 0.0645 (12) | 0.0327 (10) | 0.0620 (12) | 0.0028 (9) | −0.0113 (10) | 0.0159 (9) |
O3A | 0.084 (3) | 0.084 (5) | 0.042 (2) | 0.008 (3) | 0.003 (2) | 0.028 (3) |
O4A | 0.088 (4) | 0.0278 (18) | 0.081 (4) | 0.018 (2) | 0.035 (3) | 0.0083 (19) |
O5A | 0.0374 (18) | 0.073 (4) | 0.069 (2) | −0.0100 (19) | 0.0091 (16) | −0.011 (2) |
O6A | 0.059 (2) | 0.163 (6) | 0.0508 (19) | 0.040 (3) | 0.0193 (17) | 0.043 (3) |
O7A | 0.058 (2) | 0.034 (2) | 0.069 (2) | 0.0084 (17) | 0.0067 (16) | 0.0041 (19) |
O8A | 0.049 (2) | 0.045 (2) | 0.134 (5) | −0.0157 (14) | 0.039 (3) | −0.0196 (18) |
O3B | 0.040 (4) | 0.182 (16) | 0.061 (4) | 0.039 (6) | 0.003 (3) | 0.030 (6) |
O4B | 0.175 (15) | 0.056 (7) | 0.151 (14) | 0.054 (7) | 0.128 (12) | 0.071 (8) |
O5B | 0.084 (6) | 0.061 (4) | 0.075 (5) | −0.001 (4) | 0.014 (5) | −0.031 (4) |
O6B | 0.15 (3) | 0.105 (19) | 0.12 (2) | 0.088 (17) | 0.097 (19) | 0.110 (18) |
O7B | 0.11 (2) | 0.037 (11) | 0.13 (2) | −0.029 (13) | 0.062 (16) | −0.064 (14) |
O8B | 0.024 (7) | 0.25 (3) | 0.034 (9) | −0.015 (16) | −0.015 (6) | −0.035 (16) |
S1 | 0.0414 (4) | 0.0375 (4) | 0.0405 (4) | 0.0049 (3) | 0.0091 (3) | 0.0067 (3) |
S2 | 0.0331 (3) | 0.0365 (4) | 0.0442 (4) | 0.0020 (3) | 0.0069 (3) | 0.0053 (3) |
Geometric parameters (Å, º) top
C1—N2 | 1.329 (3) | C17—H17A | 0.9600 |
C1—C2 | 1.379 (3) | C17—H17B | 0.9600 |
C1—C5 | 1.505 (3) | C17—H17C | 0.9600 |
C2—N1 | 1.334 (3) | C18—C19 | 1.381 (4) |
C2—H2 | 0.9300 | C18—C23 | 1.386 (3) |
C3—N1 | 1.323 (3) | C18—S2 | 1.768 (2) |
C3—C4 | 1.382 (4) | C19—C20 | 1.386 (4) |
C3—H3 | 0.9300 | C19—H19 | 0.9300 |
C4—N2 | 1.333 (3) | C20—C21 | 1.372 (4) |
C4—H4 | 0.9300 | C20—H20 | 0.9300 |
C5—O1 | 1.234 (3) | C21—C22 | 1.393 (4) |
C5—N3 | 1.319 (3) | C21—C24 | 1.514 (4) |
C6—N5 | 1.336 (3) | C22—C23 | 1.386 (4) |
C6—C7 | 1.375 (3) | C22—H22 | 0.9300 |
C6—C10 | 1.505 (3) | C23—H23 | 0.9300 |
C7—N4 | 1.334 (3) | C24—H24A | 0.9600 |
C7—H7 | 0.9300 | C24—H24B | 0.9600 |
C8—N4 | 1.321 (3) | C24—H24C | 0.9600 |
C8—C9 | 1.376 (4) | N1—H1A | 0.94 (3) |
C8—H8 | 0.9300 | N3—H3A | 0.94 (3) |
C9—N5 | 1.335 (3) | N3—H3B | 0.83 (3) |
C9—H9 | 0.9300 | N4—H4A | 0.90 (3) |
C10—O2 | 1.225 (3) | N6—H6A | 0.89 (3) |
C10—N6 | 1.321 (3) | N6—H6B | 0.89 (3) |
C11—C12 | 1.385 (3) | O3A—S1 | 1.418 (6) |
C11—C16 | 1.385 (3) | O4A—S1 | 1.391 (3) |
C11—S1 | 1.769 (2) | O5A—S1 | 1.468 (3) |
C12—C13 | 1.381 (4) | O6A—S2 | 1.446 (5) |
C12—H12 | 0.9300 | O7A—S2 | 1.438 (5) |
C13—C14 | 1.381 (4) | O8A—S2 | 1.411 (4) |
C13—H13 | 0.9300 | O3B—S1 | 1.385 (6) |
C14—C15 | 1.388 (4) | O4B—S1 | 1.349 (11) |
C14—C17 | 1.514 (4) | O5B—S1 | 1.528 (7) |
C15—C16 | 1.382 (4) | O6B—S2 | 1.31 (2) |
C15—H15 | 0.9300 | O7B—S2 | 1.40 (2) |
C16—H16 | 0.9300 | O8B—S2 | 1.399 (18) |
| | | |
N2—C1—C2 | 121.5 (2) | C18—C19—H19 | 120.5 |
N2—C1—C5 | 119.4 (2) | C20—C19—H19 | 120.5 |
C2—C1—C5 | 119.1 (2) | C21—C20—C19 | 122.2 (3) |
N1—C2—C1 | 118.3 (2) | C21—C20—H20 | 118.9 |
N1—C2—H2 | 120.9 | C19—C20—H20 | 118.9 |
C1—C2—H2 | 120.9 | C20—C21—C22 | 117.9 (3) |
N1—C3—C4 | 118.1 (2) | C20—C21—C24 | 121.6 (4) |
N1—C3—H3 | 121.0 | C22—C21—C24 | 120.5 (4) |
C4—C3—H3 | 121.0 | C23—C22—C21 | 121.3 (3) |
N2—C4—C3 | 121.7 (2) | C23—C22—H22 | 119.4 |
N2—C4—H4 | 119.2 | C21—C22—H22 | 119.4 |
C3—C4—H4 | 119.2 | C22—C23—C18 | 119.3 (3) |
O1—C5—N3 | 125.0 (2) | C22—C23—H23 | 120.4 |
O1—C5—C1 | 119.4 (2) | C18—C23—H23 | 120.4 |
N3—C5—C1 | 115.7 (2) | C21—C24—H24A | 109.5 |
N5—C6—C7 | 121.8 (2) | C21—C24—H24B | 109.5 |
N5—C6—C10 | 118.7 (2) | H24A—C24—H24B | 109.5 |
C7—C6—C10 | 119.5 (2) | C21—C24—H24C | 109.5 |
N4—C7—C6 | 118.5 (2) | H24A—C24—H24C | 109.5 |
N4—C7—H7 | 120.8 | H24B—C24—H24C | 109.5 |
C6—C7—H7 | 120.8 | C3—N1—C2 | 122.0 (2) |
N4—C8—C9 | 119.2 (3) | C3—N1—H1A | 123.2 (19) |
N4—C8—H8 | 120.4 | C2—N1—H1A | 114.7 (19) |
C9—C8—H8 | 120.4 | C1—N2—C4 | 118.4 (2) |
N5—C9—C8 | 121.4 (2) | C5—N3—H3A | 119.6 (14) |
N5—C9—H9 | 119.3 | C5—N3—H3B | 117.8 (19) |
C8—C9—H9 | 119.3 | H3A—N3—H3B | 123 (2) |
O2—C10—N6 | 124.5 (2) | C8—N4—C7 | 121.3 (2) |
O2—C10—C6 | 119.4 (2) | C8—N4—H4A | 117 (2) |
N6—C10—C6 | 116.1 (2) | C7—N4—H4A | 122 (2) |
C12—C11—C16 | 120.0 (2) | C9—N5—C6 | 117.9 (2) |
C12—C11—S1 | 120.87 (19) | C10—N6—H6A | 119.8 (17) |
C16—C11—S1 | 119.03 (19) | C10—N6—H6B | 116.8 (16) |
C13—C12—C11 | 119.3 (3) | H6A—N6—H6B | 122 (2) |
C13—C12—H12 | 120.3 | O4B—S1—O3B | 119.6 (7) |
C11—C12—H12 | 120.3 | O4A—S1—O3A | 115.2 (3) |
C12—C13—C14 | 121.8 (3) | O4A—S1—O5A | 111.8 (3) |
C12—C13—H13 | 119.1 | O3A—S1—O5A | 108.9 (3) |
C14—C13—H13 | 119.1 | O4B—S1—O5B | 107.3 (7) |
C13—C14—C15 | 117.9 (3) | O3B—S1—O5B | 109.1 (5) |
C13—C14—C17 | 121.4 (3) | O4B—S1—C11 | 110.5 (5) |
C15—C14—C17 | 120.7 (3) | O3B—S1—C11 | 108.4 (3) |
C16—C15—C14 | 121.5 (3) | O4A—S1—C11 | 108.52 (17) |
C16—C15—H15 | 119.3 | O3A—S1—C11 | 106.6 (3) |
C14—C15—H15 | 119.3 | O5A—S1—C11 | 105.22 (15) |
C15—C16—C11 | 119.4 (3) | O5B—S1—C11 | 100.1 (3) |
C15—C16—H16 | 120.3 | O6B—S2—O7B | 112.9 (19) |
C11—C16—H16 | 120.3 | O6B—S2—O8B | 111.6 (17) |
C14—C17—H17A | 109.5 | O7B—S2—O8B | 110.8 (16) |
C14—C17—H17B | 109.5 | O8A—S2—O7A | 112.2 (2) |
H17A—C17—H17B | 109.5 | O8A—S2—O6A | 112.8 (3) |
C14—C17—H17C | 109.5 | O7A—S2—O6A | 111.1 (3) |
H17A—C17—H17C | 109.5 | O6B—S2—C18 | 112.7 (12) |
H17B—C17—H17C | 109.5 | O7B—S2—C18 | 105.2 (11) |
C19—C18—C23 | 120.4 (2) | O8B—S2—C18 | 103.1 (9) |
C19—C18—S2 | 121.4 (2) | O8A—S2—C18 | 107.6 (2) |
C23—C18—S2 | 118.16 (19) | O7A—S2—C18 | 107.6 (2) |
C18—C19—C20 | 119.0 (3) | O6A—S2—C18 | 105.1 (2) |