Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617016461/ky3131sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617016461/ky31313asup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617016461/ky31313asup4.cml | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229617016461/ky31313bsup3.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617016461/ky31313bsup5.cml |
CCDC references: 1585810; 1585809
Data collection: COLLECT (Bruker, 2004) for (3a); CrysAlis PRO (Rigaku OD, 2015) for (3b). Cell refinement: SCALEPACK (Otwinowski & Minor, 1997) for (3a); CrysAlis PRO (Rigaku OD, 2015) for (3b). Data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997) for (3a); CrysAlis PRO (Rigaku OD, 2015) for (3b). Program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and SHELXL2014 (Sheldrick, 2015) for (3a); SHELXL2013 (Sheldrick, 2015) for (3b). For both structures, molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).
C16H20ClN4O2+·C6H4NO2− | F(000) = 960 |
Mr = 457.91 | Dx = 1.42 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 7626 reflections |
a = 22.6220 (4) Å | θ = 1.0–27.5° |
b = 7.1937 (2) Å | µ = 0.22 mm−1 |
c = 13.5315 (7) Å | T = 120 K |
β = 103.499 (2)° | Plate, colourless |
V = 2141.23 (13) Å3 | 0.39 × 0.35 × 0.11 mm |
Z = 4 |
Bruker KappaCCD diffractometer | 4720 independent reflections |
Horizonally mounted graphite crystal monochromator | 3651 reflections with I > 2σ(I) |
Detector resolution: 9 pixels mm-1 | Rint = 0.045 |
CCD scans | θmax = 27.2°, θmin = 3.0° |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | h = −28→29 |
Tmin = 0.901, Tmax = 1.000 | k = −9→9 |
14522 measured reflections | l = −17→17 |
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)] = 0.043 | w = 1/[σ2(Fo2) + (0.036P)2 + 1.8941P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.103 | (Δ/σ)max < 0.001 |
S = 1.02 | Δρmax = 0.60 e Å−3 |
4720 reflections | Δρmin = −0.6 e Å−3 |
302 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0045 (9) |
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. |
x | y | z | Uiso*/Ueq | ||
C12 | 0.40993 (9) | 0.1213 (3) | −0.08873 (15) | 0.0256 (4) | |
H12 | 0.404 | 0.2415 | −0.1184 | 0.031* | |
C11 | 0.43467 (9) | −0.0182 (3) | −0.13694 (16) | 0.0305 (5) | |
H11 | 0.4452 | 0.0055 | −0.1997 | 0.037* | |
C10 | 0.44382 (8) | −0.1919 (3) | −0.09286 (16) | 0.0272 (5) | |
C9 | 0.42888 (8) | −0.2292 (3) | −0.00131 (16) | 0.0256 (4) | |
H9 | 0.4359 | −0.3492 | 0.0285 | 0.031* | |
C8 | 0.40350 (8) | −0.0900 (3) | 0.04651 (15) | 0.0222 (4) | |
H8 | 0.3928 | −0.1152 | 0.1091 | 0.027* | |
C7 | 0.39348 (8) | 0.0877 (3) | 0.00314 (14) | 0.0201 (4) | |
C6 | 0.36503 (8) | 0.2375 (3) | 0.04789 (14) | 0.0189 (4) | |
H6 | 0.3672 | 0.3571 | 0.0192 | 0.023* | |
C5 | 0.33611 (8) | 0.2303 (2) | 0.12419 (13) | 0.0162 (4) | |
N1 | 0.32477 (7) | 0.0767 (2) | 0.18039 (11) | 0.0166 (3) | |
C2 | 0.28577 (8) | 0.1363 (2) | 0.23098 (13) | 0.0140 (3) | |
N3 | 0.27035 (7) | 0.3234 (2) | 0.21673 (11) | 0.0149 (3) | |
C4 | 0.30176 (8) | 0.3934 (2) | 0.14909 (13) | 0.0157 (4) | |
O4 | 0.29908 (6) | 0.55285 (17) | 0.11713 (9) | 0.0198 (3) | |
N2 | 0.26329 (6) | 0.03067 (19) | 0.29710 (11) | 0.0145 (3) | |
C13 | 0.27837 (8) | −0.1682 (2) | 0.29849 (13) | 0.0158 (4) | |
H13A | 0.3216 | −0.1834 | 0.2967 | 0.019* | |
H13B | 0.2531 | −0.2294 | 0.2375 | 0.019* | |
C14 | 0.26716 (8) | −0.2596 (2) | 0.39329 (13) | 0.0156 (4) | |
H14A | 0.2759 | −0.3943 | 0.3919 | 0.019* | |
H14B | 0.2948 | −0.2055 | 0.4541 | 0.019* | |
N4 | 0.20229 (7) | −0.2312 (2) | 0.39956 (11) | 0.0134 (3) | |
C16 | 0.19018 (8) | −0.0265 (2) | 0.40117 (13) | 0.0151 (4) | |
H16A | 0.2172 | 0.0298 | 0.462 | 0.018* | |
H16B | 0.1476 | −0.0055 | 0.4054 | 0.018* | |
C15 | 0.20093 (8) | 0.0653 (2) | 0.30678 (13) | 0.0148 (4) | |
H15A | 0.1717 | 0.0158 | 0.2463 | 0.018* | |
H15B | 0.1941 | 0.2008 | 0.3101 | 0.018* | |
C17 | 0.18754 (8) | −0.3210 (2) | 0.49056 (13) | 0.0167 (4) | |
H17A | 0.1475 | −0.2748 | 0.4978 | 0.02* | |
H17B | 0.2183 | −0.2825 | 0.5519 | 0.02* | |
C18 | 0.18561 (8) | −0.5321 (2) | 0.48602 (13) | 0.0166 (4) | |
H18A | 0.1577 | −0.5758 | 0.4226 | 0.02* | |
H18B | 0.2266 | −0.5843 | 0.4899 | 0.02* | |
O1 | 0.16389 (6) | −0.58317 (19) | 0.57220 (9) | 0.0218 (3) | |
C20 | 0.03275 (8) | −0.3026 (2) | 0.06731 (14) | 0.0179 (4) | |
H20 | 0.0343 | −0.3708 | 0.0078 | 0.021* | |
C21 | −0.01453 (9) | −0.1790 (3) | 0.06659 (15) | 0.0238 (4) | |
H21 | −0.0464 | −0.1634 | 0.0075 | 0.029* | |
C22 | −0.01401 (9) | −0.0794 (3) | 0.15396 (16) | 0.0273 (5) | |
H22 | −0.0457 | 0.006 | 0.1564 | 0.033* | |
C23 | 0.03350 (9) | −0.1064 (3) | 0.23782 (15) | 0.0248 (4) | |
H23 | 0.0339 | −0.0348 | 0.297 | 0.03* | |
N5 | 0.07913 (7) | −0.2275 (2) | 0.24095 (11) | 0.0178 (3) | |
C19 | 0.07778 (8) | −0.3255 (2) | 0.15591 (13) | 0.0137 (3) | |
C24 | 0.12818 (8) | −0.4683 (2) | 0.16024 (13) | 0.0139 (4) | |
O3 | 0.16842 (5) | −0.47981 (17) | 0.24246 (9) | 0.0161 (3) | |
O2 | 0.12535 (6) | −0.56308 (17) | 0.08229 (9) | 0.0188 (3) | |
Cl1 | 0.47425 (3) | −0.36900 (9) | −0.15369 (4) | 0.04095 (18) | |
H3 | 0.2369 (11) | 0.386 (3) | 0.2308 (17) | 0.035 (6)* | |
H4 | 0.1785 (10) | −0.281 (3) | 0.3439 (16) | 0.020 (5)* | |
H1 | 0.1558 (12) | −0.709 (4) | 0.5709 (19) | 0.049 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C12 | 0.0216 (10) | 0.0325 (11) | 0.0258 (10) | −0.0036 (8) | 0.0118 (8) | 0.0002 (9) |
C11 | 0.0218 (10) | 0.0474 (14) | 0.0262 (11) | −0.0049 (9) | 0.0133 (8) | −0.0066 (10) |
C10 | 0.0148 (9) | 0.0370 (12) | 0.0313 (11) | 0.0005 (8) | 0.0081 (8) | −0.0134 (9) |
C9 | 0.0175 (9) | 0.0263 (10) | 0.0330 (11) | 0.0016 (8) | 0.0061 (8) | −0.0044 (9) |
C8 | 0.0178 (9) | 0.0258 (10) | 0.0240 (10) | −0.0002 (8) | 0.0067 (8) | −0.0014 (8) |
C7 | 0.0131 (8) | 0.0274 (10) | 0.0216 (9) | −0.0035 (7) | 0.0074 (7) | −0.0026 (8) |
C6 | 0.0167 (9) | 0.0180 (9) | 0.0230 (10) | −0.0021 (7) | 0.0066 (7) | 0.0023 (7) |
C5 | 0.0158 (8) | 0.0142 (8) | 0.0189 (9) | 0.0000 (7) | 0.0045 (7) | 0.0010 (7) |
N1 | 0.0168 (7) | 0.0158 (7) | 0.0185 (8) | 0.0003 (6) | 0.0070 (6) | 0.0021 (6) |
C2 | 0.0143 (8) | 0.0134 (8) | 0.0143 (8) | 0.0000 (7) | 0.0036 (6) | 0.0003 (7) |
N3 | 0.0164 (7) | 0.0126 (7) | 0.0171 (7) | 0.0018 (6) | 0.0067 (6) | 0.0014 (6) |
C4 | 0.0162 (8) | 0.0171 (9) | 0.0134 (8) | −0.0008 (7) | 0.0025 (7) | 0.0010 (7) |
O4 | 0.0271 (7) | 0.0140 (6) | 0.0200 (7) | 0.0005 (5) | 0.0087 (5) | 0.0041 (5) |
N2 | 0.0176 (7) | 0.0111 (7) | 0.0168 (7) | 0.0022 (6) | 0.0081 (6) | 0.0024 (6) |
C13 | 0.0211 (9) | 0.0102 (8) | 0.0183 (9) | 0.0027 (7) | 0.0093 (7) | 0.0009 (7) |
C14 | 0.0171 (9) | 0.0137 (8) | 0.0169 (9) | 0.0019 (7) | 0.0056 (7) | 0.0016 (7) |
N4 | 0.0196 (8) | 0.0115 (7) | 0.0100 (7) | −0.0005 (6) | 0.0057 (6) | 0.0006 (6) |
C16 | 0.0210 (9) | 0.0110 (8) | 0.0148 (8) | 0.0015 (7) | 0.0074 (7) | 0.0005 (7) |
C15 | 0.0184 (9) | 0.0121 (8) | 0.0160 (8) | 0.0021 (7) | 0.0081 (7) | 0.0024 (7) |
C17 | 0.0258 (9) | 0.0151 (9) | 0.0114 (8) | −0.0015 (7) | 0.0087 (7) | 0.0015 (7) |
C18 | 0.0216 (9) | 0.0149 (9) | 0.0146 (8) | −0.0005 (7) | 0.0069 (7) | 0.0025 (7) |
O1 | 0.0350 (8) | 0.0174 (7) | 0.0158 (6) | −0.0062 (6) | 0.0114 (6) | 0.0015 (5) |
C20 | 0.0195 (9) | 0.0157 (9) | 0.0187 (9) | −0.0035 (7) | 0.0049 (7) | −0.0023 (7) |
C21 | 0.0184 (9) | 0.0192 (10) | 0.0307 (11) | 0.0005 (8) | −0.0003 (8) | 0.0022 (8) |
C22 | 0.0228 (10) | 0.0210 (10) | 0.0383 (12) | 0.0067 (8) | 0.0076 (9) | −0.0042 (9) |
C23 | 0.0258 (10) | 0.0214 (10) | 0.0286 (11) | 0.0053 (8) | 0.0093 (8) | −0.0080 (8) |
N5 | 0.0213 (8) | 0.0153 (7) | 0.0182 (8) | 0.0010 (6) | 0.0074 (6) | −0.0038 (6) |
C19 | 0.0173 (8) | 0.0108 (8) | 0.0148 (8) | −0.0017 (7) | 0.0074 (7) | −0.0003 (6) |
C24 | 0.0170 (8) | 0.0109 (8) | 0.0157 (9) | −0.0027 (6) | 0.0078 (7) | 0.0011 (7) |
O3 | 0.0186 (6) | 0.0151 (6) | 0.0146 (6) | 0.0033 (5) | 0.0037 (5) | 0.0001 (5) |
O2 | 0.0257 (7) | 0.0166 (6) | 0.0152 (6) | 0.0026 (5) | 0.0068 (5) | −0.0048 (5) |
Cl1 | 0.0314 (3) | 0.0502 (4) | 0.0436 (3) | 0.0056 (3) | 0.0136 (2) | −0.0217 (3) |
C12—C11 | 1.384 (3) | C14—H14B | 0.99 |
C12—C7 | 1.399 (3) | N4—C17 | 1.496 (2) |
C12—H12 | 0.95 | N4—C16 | 1.499 (2) |
C11—C10 | 1.380 (3) | N4—H4 | 0.89 (2) |
C11—H11 | 0.95 | C16—C15 | 1.507 (2) |
C10—C9 | 1.384 (3) | C16—H16A | 0.99 |
C10—Cl1 | 1.743 (2) | C16—H16B | 0.99 |
C9—C8 | 1.387 (3) | C15—H15A | 0.99 |
C9—H9 | 0.95 | C15—H15B | 0.99 |
C8—C7 | 1.403 (3) | C17—C18 | 1.520 (2) |
C8—H8 | 0.95 | C17—H17A | 0.99 |
C7—C6 | 1.457 (3) | C17—H17B | 0.99 |
C6—C5 | 1.346 (2) | C18—O1 | 1.415 (2) |
C6—H6 | 0.95 | C18—H18A | 0.99 |
C5—N1 | 1.399 (2) | C18—H18B | 0.99 |
C5—C4 | 1.489 (2) | O1—H1 | 0.92 (3) |
N1—C2 | 1.309 (2) | C20—C21 | 1.389 (3) |
C2—N2 | 1.360 (2) | C20—C19 | 1.390 (2) |
C2—N3 | 1.392 (2) | C20—H20 | 0.95 |
N3—C4 | 1.378 (2) | C21—C22 | 1.380 (3) |
N3—H3 | 0.94 (2) | C21—H21 | 0.95 |
C4—O4 | 1.222 (2) | C22—C23 | 1.383 (3) |
N2—C15 | 1.468 (2) | C22—H22 | 0.95 |
N2—C13 | 1.470 (2) | C23—N5 | 1.344 (2) |
C13—C14 | 1.514 (2) | C23—H23 | 0.95 |
C13—H13A | 0.99 | N5—C19 | 1.344 (2) |
C13—H13B | 0.99 | C19—C24 | 1.525 (2) |
C14—N4 | 1.504 (2) | C24—O2 | 1.245 (2) |
C14—H14A | 0.99 | C24—O3 | 1.265 (2) |
C11—C12—C7 | 121.0 (2) | C17—N4—C14 | 113.32 (13) |
C11—C12—H12 | 119.5 | C16—N4—C14 | 108.58 (13) |
C7—C12—H12 | 119.5 | C17—N4—H4 | 108.3 (13) |
C10—C11—C12 | 119.29 (19) | C16—N4—H4 | 109.4 (13) |
C10—C11—H11 | 120.4 | C14—N4—H4 | 107.5 (13) |
C12—C11—H11 | 120.4 | N4—C16—C15 | 110.60 (14) |
C11—C10—C9 | 121.28 (18) | N4—C16—H16A | 109.5 |
C11—C10—Cl1 | 119.59 (16) | C15—C16—H16A | 109.5 |
C9—C10—Cl1 | 119.13 (17) | N4—C16—H16B | 109.5 |
C10—C9—C8 | 119.45 (19) | C15—C16—H16B | 109.5 |
C10—C9—H9 | 120.3 | H16A—C16—H16B | 108.1 |
C8—C9—H9 | 120.3 | N2—C15—C16 | 110.47 (14) |
C9—C8—C7 | 120.45 (18) | N2—C15—H15A | 109.6 |
C9—C8—H8 | 119.8 | C16—C15—H15A | 109.6 |
C7—C8—H8 | 119.8 | N2—C15—H15B | 109.6 |
C12—C7—C8 | 118.58 (18) | C16—C15—H15B | 109.6 |
C12—C7—C6 | 118.44 (18) | H15A—C15—H15B | 108.1 |
C8—C7—C6 | 122.95 (17) | N4—C17—C18 | 114.10 (14) |
C5—C6—C7 | 129.13 (17) | N4—C17—H17A | 108.7 |
C5—C6—H6 | 115.4 | C18—C17—H17A | 108.7 |
C7—C6—H6 | 115.4 | N4—C17—H17B | 108.7 |
C6—C5—N1 | 129.13 (16) | C18—C17—H17B | 108.7 |
C6—C5—C4 | 121.08 (16) | H17A—C17—H17B | 107.6 |
N1—C5—C4 | 109.13 (14) | O1—C18—C17 | 103.77 (14) |
C2—N1—C5 | 104.91 (14) | O1—C18—H18A | 111 |
N1—C2—N2 | 124.21 (16) | C17—C18—H18A | 111 |
N1—C2—N3 | 114.95 (15) | O1—C18—H18B | 111 |
N2—C2—N3 | 120.76 (15) | C17—C18—H18B | 111 |
C4—N3—C2 | 107.09 (14) | H18A—C18—H18B | 109 |
C4—N3—H3 | 121.8 (14) | C18—O1—H1 | 110.1 (16) |
C2—N3—H3 | 128.5 (14) | C21—C20—C19 | 119.33 (17) |
O4—C4—N3 | 125.95 (16) | C21—C20—H20 | 120.3 |
O4—C4—C5 | 130.15 (16) | C19—C20—H20 | 120.3 |
N3—C4—C5 | 103.87 (14) | C22—C21—C20 | 118.28 (18) |
C2—N2—C15 | 118.59 (14) | C22—C21—H21 | 120.9 |
C2—N2—C13 | 115.54 (14) | C20—C21—H21 | 120.9 |
C15—N2—C13 | 112.88 (13) | C21—C22—C23 | 118.67 (18) |
N2—C13—C14 | 110.43 (14) | C21—C22—H22 | 120.7 |
N2—C13—H13A | 109.6 | C23—C22—H22 | 120.7 |
C14—C13—H13A | 109.6 | N5—C23—C22 | 124.14 (18) |
N2—C13—H13B | 109.6 | N5—C23—H23 | 117.9 |
C14—C13—H13B | 109.6 | C22—C23—H23 | 117.9 |
H13A—C13—H13B | 108.1 | C19—N5—C23 | 116.69 (16) |
N4—C14—C13 | 110.32 (14) | N5—C19—C20 | 122.84 (16) |
N4—C14—H14A | 109.6 | N5—C19—C24 | 116.92 (15) |
C13—C14—H14A | 109.6 | C20—C19—C24 | 120.24 (15) |
N4—C14—H14B | 109.6 | O2—C24—O3 | 126.38 (16) |
C13—C14—H14B | 109.6 | O2—C24—C19 | 116.49 (15) |
H14A—C14—H14B | 108.1 | O3—C24—C19 | 117.13 (14) |
C17—N4—C16 | 109.63 (13) | ||
C7—C12—C11—C10 | −0.8 (3) | N1—C2—N2—C13 | −8.8 (2) |
C12—C11—C10—C9 | −0.2 (3) | N3—C2—N2—C13 | 174.62 (15) |
C12—C11—C10—Cl1 | 179.37 (15) | C2—N2—C13—C14 | 163.72 (15) |
C11—C10—C9—C8 | 0.8 (3) | C15—N2—C13—C14 | −55.26 (19) |
Cl1—C10—C9—C8 | −178.71 (14) | N2—C13—C14—N4 | 56.92 (18) |
C10—C9—C8—C7 | −0.6 (3) | C13—C14—N4—C17 | 178.91 (14) |
C11—C12—C7—C8 | 1.0 (3) | C13—C14—N4—C16 | −59.02 (17) |
C11—C12—C7—C6 | −177.17 (17) | C17—N4—C16—C15 | −176.41 (14) |
C9—C8—C7—C12 | −0.3 (3) | C14—N4—C16—C15 | 59.30 (17) |
C9—C8—C7—C6 | 177.75 (17) | C2—N2—C15—C16 | −164.89 (15) |
C12—C7—C6—C5 | 167.17 (19) | C13—N2—C15—C16 | 55.39 (18) |
C8—C7—C6—C5 | −10.9 (3) | N4—C16—C15—N2 | −57.32 (19) |
C7—C6—C5—N1 | −1.0 (3) | C16—N4—C17—C18 | 168.08 (15) |
C7—C6—C5—C4 | −170.62 (17) | C14—N4—C17—C18 | −70.43 (19) |
C6—C5—N1—C2 | −168.27 (18) | N4—C17—C18—O1 | −173.10 (14) |
C4—C5—N1—C2 | 2.37 (19) | C19—C20—C21—C22 | 1.7 (3) |
C5—N1—C2—N2 | −178.77 (16) | C20—C21—C22—C23 | 0.3 (3) |
C5—N1—C2—N3 | −2.0 (2) | C21—C22—C23—N5 | −1.5 (3) |
N1—C2—N3—C4 | 0.8 (2) | C22—C23—N5—C19 | 0.7 (3) |
N2—C2—N3—C4 | 177.68 (15) | C23—N5—C19—C20 | 1.4 (3) |
C2—N3—C4—O4 | 178.92 (17) | C23—N5—C19—C24 | −177.84 (16) |
C2—N3—C4—C5 | 0.73 (17) | C21—C20—C19—N5 | −2.6 (3) |
C6—C5—C4—O4 | −8.5 (3) | C21—C20—C19—C24 | 176.59 (16) |
N1—C5—C4—O4 | 179.99 (17) | N5—C19—C24—O2 | 177.51 (15) |
C6—C5—C4—N3 | 169.60 (16) | C20—C19—C24—O2 | −1.8 (2) |
N1—C5—C4—N3 | −1.93 (18) | N5—C19—C24—O3 | −2.0 (2) |
N1—C2—N2—C15 | −147.47 (17) | C20—C19—C24—O3 | 178.70 (16) |
N3—C2—N2—C15 | 35.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13B···O4i | 0.99 | 2.64 | 3.287 (2) | 123 |
C13—H13B···O3 | 0.99 | 2.64 | 3.302 (2) | 124 |
C14—H14B···O4ii | 0.99 | 2.45 | 3.299 (2) | 144 |
C16—H16A···O4ii | 0.99 | 2.52 | 3.359 (2) | 142 |
C16—H16B···O2iii | 0.99 | 2.61 | 3.202 (2) | 119 |
C15—H15A···O1iv | 0.99 | 2.37 | 3.091 (2) | 129 |
C15—H15B···O3v | 0.99 | 2.49 | 3.422 (2) | 157 |
C17—H17B···O4ii | 0.99 | 2.47 | 3.317 (2) | 144 |
C18—H18A···O3 | 0.99 | 2.6 | 3.249 (2) | 123 |
C22—H22···N5vi | 0.95 | 2.58 | 3.402 (2) | 145 |
N3—H3···O3v | 0.94 (2) | 1.86 (2) | 2.796 (2) | 173 (2) |
N4—H4···N5 | 0.89 (2) | 2.38 (2) | 3.095 (2) | 137 (2) |
N4—H4···O3 | 0.89 (2) | 1.96 (2) | 2.747 (2) | 147 (2) |
O1—H1···O2vii | 0.92 (3) | 1.80 (3) | 2.704 (2) | 166 (2) |
Symmetry codes: (i) x, y−1, z; (ii) x, −y+1/2, z+1/2; (iii) x, −y−1/2, z+1/2; (iv) x, −y−1/2, z−1/2; (v) x, y+1, z; (vi) −x, y+1/2, −z+1/2; (vii) x, −y−3/2, z+1/2. |
C16H20ClN4O2+·C8H6NO4− | Z = 2 |
Mr = 515.95 | F(000) = 540 |
Triclinic, P1 | Dx = 1.395 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54184 Å |
a = 7.8667 (4) Å | Cell parameters from 4966 reflections |
b = 11.9015 (7) Å | θ = 3.3–71.8° |
c = 14.4406 (9) Å | µ = 1.81 mm−1 |
α = 66.859 (6)° | T = 298 K |
β = 85.085 (4)° | Block, colourless |
γ = 81.332 (5)° | 0.49 × 0.17 × 0.14 mm |
V = 1228.51 (13) Å3 |
Rigaku SuperNova Dual Source diffractometer with an Atlas detector | 4750 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 3217 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.072 |
Detector resolution: 10.3756 pixels mm-1 | θmax = 71.8°, θmin = 3.3° |
ω scans | h = −9→9 |
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015) | k = −14→14 |
Tmin = 0.824, Tmax = 0.947 | l = −17→17 |
17827 measured reflections |
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)] = 0.068 | w = 1/[σ2(Fo2) + (0.1334P)2 + 0.0797P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.223 | (Δ/σ)max = 0.001 |
S = 1.03 | Δρmax = 0.24 e Å−3 |
4750 reflections | Δρmin = −0.40 e Å−3 |
354 parameters | Extinction correction: SHELXL2013 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
2 restraints | Extinction coefficient: 0.0034 (10) |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C2 | 0.9074 (3) | 1.1563 (2) | 0.8711 (2) | 0.0626 (6) | |
C4 | 1.1738 (4) | 1.1112 (3) | 0.8186 (2) | 0.0702 (7) | |
C5 | 1.0437 (3) | 1.0585 (2) | 0.7838 (2) | 0.0656 (7) | |
C6 | 1.0850 (4) | 1.0010 (3) | 0.7199 (2) | 0.0696 (7) | |
H6 | 1.2017 | 0.9878 | 0.7048 | 0.084* | |
C7 | 0.9712 (4) | 0.9568 (2) | 0.6713 (2) | 0.0662 (7) | |
C8 | 0.7925 (4) | 0.9911 (3) | 0.6676 (2) | 0.0710 (7) | |
H8 | 0.742 | 1.045 | 0.6974 | 0.085* | |
C9 | 0.6915 (4) | 0.9464 (3) | 0.6208 (2) | 0.0772 (8) | |
H9 | 0.5735 | 0.9713 | 0.6178 | 0.093* | |
C10 | 0.7647 (5) | 0.8637 (3) | 0.5775 (3) | 0.0815 (9) | |
C11 | 0.9421 (5) | 0.8314 (3) | 0.5774 (2) | 0.0811 (9) | |
H11 | 0.9922 | 0.7785 | 0.5466 | 0.097* | |
C12 | 1.0424 (4) | 0.8781 (3) | 0.6230 (2) | 0.0741 (8) | |
H12 | 1.1611 | 0.857 | 0.622 | 0.089* | |
C13 | 0.6051 (3) | 1.1853 (3) | 0.9131 (3) | 0.0732 (8) | |
H13A | 0.6025 | 1.1132 | 0.8979 | 0.088* | |
H13B | 0.5523 | 1.2567 | 0.8584 | 0.088* | |
C14 | 0.5053 (3) | 1.1712 (3) | 1.0105 (2) | 0.0681 (7) | |
H14A | 0.3861 | 1.1651 | 1.003 | 0.082* | |
H14B | 0.5522 | 1.0958 | 1.0639 | 0.082* | |
C15 | 0.7990 (4) | 1.3020 (3) | 0.9521 (3) | 0.0716 (8) | |
H15A | 0.7567 | 1.3794 | 0.8992 | 0.086* | |
H15B | 0.9192 | 1.3037 | 0.9613 | 0.086* | |
C16 | 0.6990 (3) | 1.2885 (3) | 1.0478 (2) | 0.0691 (7) | |
H16A | 0.7058 | 1.3593 | 1.0642 | 0.083* | |
H16B | 0.749 | 1.2155 | 1.1022 | 0.083* | |
C17 | 0.4154 (4) | 1.2688 (3) | 1.1355 (2) | 0.0777 (8) | |
H17A | 0.4545 | 1.19 | 1.1879 | 0.093* | |
H17B | 0.443 | 1.3327 | 1.1554 | 0.093* | |
C18 | 0.2232 (4) | 1.2802 (3) | 1.1300 (3) | 0.0772 (8) | |
H18A | 0.1955 | 1.2244 | 1.1011 | 0.093* | |
H18B | 0.1733 | 1.2551 | 1.1978 | 0.093* | |
C19 | 0.0993 (4) | 1.4825 (3) | 0.6908 (2) | 0.0650 (7) | |
C20 | −0.0722 (4) | 1.5135 (3) | 0.7117 (3) | 0.0760 (8) | |
H20 | −0.1009 | 1.5639 | 0.7477 | 0.091* | |
C21 | −0.2001 (4) | 1.4717 (3) | 0.6807 (3) | 0.0769 (8) | |
H21 | −0.3149 | 1.4938 | 0.6949 | 0.092* | |
C22 | −0.1570 (4) | 1.3968 (3) | 0.6282 (2) | 0.0681 (7) | |
C23 | 0.0123 (4) | 1.3635 (3) | 0.6064 (2) | 0.0717 (7) | |
H23 | 0.0401 | 1.3129 | 0.5706 | 0.086* | |
C24 | 0.1395 (4) | 1.4060 (3) | 0.6384 (2) | 0.0721 (7) | |
H24 | 0.2542 | 1.3831 | 0.6247 | 0.087* | |
C25 | 0.2391 (4) | 1.5278 (3) | 0.7276 (2) | 0.0795 (9) | |
H25A | 0.3411 | 1.5275 | 0.6849 | 0.095* | |
H25B | 0.2018 | 1.6125 | 0.7196 | 0.095* | |
C26 | 0.2878 (3) | 1.4542 (2) | 0.8359 (2) | 0.0608 (6) | |
N1 | 0.8816 (3) | 1.0881 (2) | 0.82195 (19) | 0.0672 (6) | |
N2 | 0.7835 (3) | 1.2002 (2) | 0.9222 (2) | 0.0724 (7) | |
N3 | 1.0772 (3) | 1.1742 (2) | 0.8716 (2) | 0.0676 (6) | |
H3 | 1.113 (5) | 1.232 (4) | 0.888 (3) | 0.101* | |
N4 | 0.5142 (3) | 1.2783 (2) | 1.03857 (17) | 0.0606 (5) | |
HN4 | 0.467 (4) | 1.351 (3) | 0.985 (3) | 0.091* | |
N5 | −0.2917 (4) | 1.3529 (3) | 0.5927 (3) | 0.0880 (8) | |
O1 | 0.1482 (3) | 1.4005 (2) | 1.0724 (2) | 0.0936 (7) | |
H1 | 0.153 (6) | 1.406 (5) | 1.005 (4) | 0.14* | |
O2 | 0.1998 (2) | 1.37064 (18) | 0.89135 (14) | 0.0682 (5) | |
O3 | 0.4151 (3) | 1.48002 (18) | 0.86656 (15) | 0.0730 (6) | |
O4 | 1.3296 (3) | 1.1026 (2) | 0.8054 (2) | 0.0896 (7) | |
O5A | −0.243 (5) | 1.327 (4) | 0.525 (3) | 0.121 (11) | 0.22 (4) |
O6A | −0.426 (3) | 1.339 (2) | 0.6425 (14) | 0.077 (8) | 0.22 (4) |
O5B | −0.2577 (10) | 1.2940 (12) | 0.5389 (8) | 0.094 (2) | 0.78 (4) |
O6B | −0.4396 (12) | 1.384 (3) | 0.6129 (19) | 0.178 (5) | 0.78 (4) |
Cl1 | 0.63520 (16) | 0.80286 (10) | 0.52260 (9) | 0.1174 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C2 | 0.0546 (13) | 0.0636 (15) | 0.0742 (17) | −0.0137 (11) | −0.0018 (12) | −0.0291 (13) |
C4 | 0.0575 (15) | 0.0651 (16) | 0.086 (2) | −0.0105 (12) | −0.0053 (13) | −0.0257 (15) |
C5 | 0.0573 (14) | 0.0573 (14) | 0.0815 (19) | −0.0095 (11) | −0.0005 (13) | −0.0255 (13) |
C6 | 0.0609 (15) | 0.0611 (15) | 0.084 (2) | −0.0092 (12) | 0.0060 (13) | −0.0264 (14) |
C7 | 0.0714 (16) | 0.0550 (14) | 0.0698 (17) | −0.0135 (12) | 0.0040 (13) | −0.0207 (13) |
C8 | 0.0756 (17) | 0.0631 (16) | 0.0735 (18) | −0.0097 (13) | −0.0002 (14) | −0.0257 (14) |
C9 | 0.0802 (19) | 0.0676 (17) | 0.078 (2) | −0.0080 (14) | −0.0118 (15) | −0.0201 (15) |
C10 | 0.106 (2) | 0.0659 (17) | 0.0721 (19) | −0.0131 (16) | −0.0172 (17) | −0.0224 (15) |
C11 | 0.104 (2) | 0.0700 (18) | 0.0718 (19) | −0.0047 (16) | −0.0038 (17) | −0.0318 (15) |
C12 | 0.0824 (19) | 0.0645 (16) | 0.0711 (18) | −0.0083 (14) | 0.0070 (15) | −0.0239 (14) |
C13 | 0.0546 (14) | 0.0827 (19) | 0.102 (2) | −0.0168 (13) | −0.0014 (14) | −0.0542 (18) |
C14 | 0.0569 (14) | 0.0624 (15) | 0.091 (2) | −0.0144 (11) | −0.0015 (13) | −0.0338 (14) |
C15 | 0.0623 (15) | 0.0812 (18) | 0.091 (2) | −0.0264 (13) | 0.0052 (14) | −0.0499 (16) |
C16 | 0.0607 (15) | 0.0759 (17) | 0.0800 (19) | −0.0146 (13) | −0.0098 (13) | −0.0364 (15) |
C17 | 0.085 (2) | 0.085 (2) | 0.0613 (17) | −0.0244 (16) | 0.0035 (14) | −0.0229 (15) |
C18 | 0.0805 (19) | 0.0786 (19) | 0.0745 (19) | −0.0179 (15) | 0.0145 (15) | −0.0323 (16) |
C19 | 0.0673 (15) | 0.0641 (15) | 0.0599 (15) | −0.0189 (12) | −0.0107 (12) | −0.0145 (12) |
C20 | 0.0783 (19) | 0.0770 (19) | 0.082 (2) | −0.0122 (15) | −0.0031 (15) | −0.0398 (16) |
C21 | 0.0594 (15) | 0.086 (2) | 0.092 (2) | −0.0087 (14) | −0.0016 (14) | −0.0420 (18) |
C22 | 0.0587 (15) | 0.0784 (18) | 0.0706 (17) | −0.0147 (13) | −0.0093 (12) | −0.0286 (14) |
C23 | 0.0671 (16) | 0.0839 (19) | 0.0711 (18) | −0.0111 (14) | −0.0064 (13) | −0.0358 (15) |
C24 | 0.0554 (14) | 0.0868 (19) | 0.0765 (18) | −0.0104 (13) | −0.0073 (13) | −0.0323 (15) |
C25 | 0.086 (2) | 0.0771 (19) | 0.0735 (19) | −0.0308 (16) | −0.0164 (15) | −0.0162 (15) |
C26 | 0.0618 (14) | 0.0585 (14) | 0.0685 (16) | −0.0132 (11) | −0.0060 (12) | −0.0285 (12) |
N1 | 0.0578 (12) | 0.0684 (13) | 0.0858 (16) | −0.0156 (10) | 0.0016 (11) | −0.0387 (12) |
N2 | 0.0569 (12) | 0.0843 (16) | 0.0986 (18) | −0.0222 (11) | 0.0038 (12) | −0.0559 (14) |
N3 | 0.0540 (12) | 0.0706 (14) | 0.0857 (16) | −0.0151 (10) | −0.0066 (11) | −0.0349 (12) |
N4 | 0.0613 (12) | 0.0617 (13) | 0.0612 (13) | −0.0144 (10) | −0.0004 (10) | −0.0243 (10) |
N5 | 0.0676 (16) | 0.108 (2) | 0.101 (2) | −0.0238 (15) | −0.0094 (16) | −0.0481 (18) |
O1 | 0.1076 (18) | 0.0878 (16) | 0.0816 (15) | 0.0015 (13) | −0.0005 (13) | −0.0341 (13) |
O2 | 0.0682 (11) | 0.0745 (12) | 0.0656 (11) | −0.0260 (9) | −0.0036 (9) | −0.0246 (9) |
O3 | 0.0737 (12) | 0.0732 (12) | 0.0765 (13) | −0.0263 (9) | −0.0162 (10) | −0.0248 (10) |
O4 | 0.0538 (11) | 0.1030 (17) | 0.1184 (19) | −0.0120 (10) | −0.0037 (11) | −0.0485 (15) |
O5A | 0.18 (3) | 0.14 (2) | 0.081 (12) | −0.110 (19) | 0.023 (12) | −0.066 (13) |
O6A | 0.062 (10) | 0.101 (13) | 0.076 (14) | −0.038 (7) | 0.012 (6) | −0.036 (10) |
O5B | 0.089 (3) | 0.106 (5) | 0.109 (4) | −0.035 (3) | −0.015 (3) | −0.053 (4) |
O6B | 0.061 (3) | 0.269 (13) | 0.284 (12) | −0.026 (6) | −0.007 (6) | −0.190 (10) |
Cl1 | 0.1404 (10) | 0.1029 (7) | 0.1250 (9) | −0.0017 (6) | −0.0550 (7) | −0.0556 (6) |
C2—N1 | 1.316 (3) | C16—H16A | 0.97 |
C2—N2 | 1.339 (4) | C16—H16B | 0.97 |
C2—N3 | 1.385 (3) | C17—C18 | 1.504 (4) |
C4—O4 | 1.218 (3) | C17—N4 | 1.514 (4) |
C4—N3 | 1.380 (4) | C17—H17A | 0.97 |
C4—C5 | 1.491 (4) | C17—H17B | 0.97 |
C5—C6 | 1.342 (4) | C18—O1 | 1.408 (4) |
C5—N1 | 1.396 (4) | C18—H18A | 0.97 |
C6—C7 | 1.454 (4) | C18—H18B | 0.97 |
C6—H6 | 0.93 | C19—C20 | 1.384 (4) |
C7—C8 | 1.402 (4) | C19—C24 | 1.384 (4) |
C7—C12 | 1.402 (4) | C19—C25 | 1.512 (4) |
C8—C9 | 1.369 (4) | C20—C21 | 1.365 (4) |
C8—H8 | 0.93 | C20—H20 | 0.93 |
C9—C10 | 1.394 (5) | C21—C22 | 1.371 (4) |
C9—H9 | 0.93 | C21—H21 | 0.93 |
C10—C11 | 1.391 (5) | C22—C23 | 1.377 (4) |
C10—Cl1 | 1.733 (3) | C22—N5 | 1.460 (4) |
C11—C12 | 1.369 (5) | C23—C24 | 1.373 (4) |
C11—H11 | 0.93 | C23—H23 | 0.93 |
C12—H12 | 0.93 | C24—H24 | 0.93 |
C13—N2 | 1.464 (3) | C25—C26 | 1.511 (4) |
C13—C14 | 1.512 (4) | C25—H25A | 0.97 |
C13—H13A | 0.97 | C25—H25B | 0.97 |
C13—H13B | 0.97 | C26—O3 | 1.253 (3) |
C14—N4 | 1.494 (3) | C26—O2 | 1.263 (3) |
C14—H14A | 0.97 | N3—H3 | 0.90 (4) |
C14—H14B | 0.97 | N4—HN4 | 0.95 (4) |
C15—N2 | 1.461 (3) | N5—O5A | 1.15 (3) |
C15—C16 | 1.494 (4) | N5—O6B | 1.212 (10) |
C15—H15A | 0.97 | N5—O6A | 1.22 (2) |
C15—H15B | 0.97 | N5—O5B | 1.227 (10) |
C16—N4 | 1.498 (3) | O1—H1 | 0.94 (5) |
N1—C2—N2 | 123.9 (2) | C18—C17—H17B | 108.5 |
N1—C2—N3 | 114.7 (3) | N4—C17—H17B | 108.5 |
N2—C2—N3 | 121.3 (2) | H17A—C17—H17B | 107.5 |
O4—C4—N3 | 126.4 (3) | O1—C18—C17 | 113.3 (3) |
O4—C4—C5 | 129.8 (3) | O1—C18—H18A | 108.9 |
N3—C4—C5 | 103.8 (2) | C17—C18—H18A | 108.9 |
C6—C5—N1 | 128.8 (3) | O1—C18—H18B | 108.9 |
C6—C5—C4 | 122.1 (3) | C17—C18—H18B | 108.9 |
N1—C5—C4 | 108.9 (2) | H18A—C18—H18B | 107.7 |
C5—C6—C7 | 128.5 (3) | C20—C19—C24 | 118.4 (3) |
C5—C6—H6 | 115.8 | C20—C19—C25 | 120.6 (3) |
C7—C6—H6 | 115.8 | C24—C19—C25 | 121.0 (3) |
C8—C7—C12 | 117.6 (3) | C21—C20—C19 | 121.5 (3) |
C8—C7—C6 | 123.4 (3) | C21—C20—H20 | 119.3 |
C12—C7—C6 | 118.9 (3) | C19—C20—H20 | 119.3 |
C9—C8—C7 | 120.9 (3) | C20—C21—C22 | 119.0 (3) |
C9—C8—H8 | 119.5 | C20—C21—H21 | 120.5 |
C7—C8—H8 | 119.5 | C22—C21—H21 | 120.5 |
C8—C9—C10 | 120.3 (3) | C21—C22—C23 | 121.2 (3) |
C8—C9—H9 | 119.9 | C21—C22—N5 | 120.0 (3) |
C10—C9—H9 | 119.9 | C23—C22—N5 | 118.9 (3) |
C11—C10—C9 | 119.8 (3) | C24—C23—C22 | 119.1 (3) |
C11—C10—Cl1 | 120.1 (3) | C24—C23—H23 | 120.4 |
C9—C10—Cl1 | 120.1 (3) | C22—C23—H23 | 120.4 |
C12—C11—C10 | 119.5 (3) | C23—C24—C19 | 120.9 (3) |
C12—C11—H11 | 120.3 | C23—C24—H24 | 119.6 |
C10—C11—H11 | 120.3 | C19—C24—H24 | 119.6 |
C11—C12—C7 | 121.8 (3) | C26—C25—C19 | 115.4 (2) |
C11—C12—H12 | 119.1 | C26—C25—H25A | 108.4 |
C7—C12—H12 | 119.1 | C19—C25—H25A | 108.4 |
N2—C13—C14 | 109.9 (2) | C26—C25—H25B | 108.4 |
N2—C13—H13A | 109.7 | C19—C25—H25B | 108.4 |
C14—C13—H13A | 109.7 | H25A—C25—H25B | 107.5 |
N2—C13—H13B | 109.7 | O3—C26—O2 | 122.9 (3) |
C14—C13—H13B | 109.7 | O3—C26—C25 | 117.6 (2) |
H13A—C13—H13B | 108.2 | O2—C26—C25 | 119.5 (2) |
N4—C14—C13 | 110.9 (2) | C2—N1—C5 | 105.1 (2) |
N4—C14—H14A | 109.5 | C2—N2—C15 | 123.4 (2) |
C13—C14—H14A | 109.5 | C2—N2—C13 | 118.6 (2) |
N4—C14—H14B | 109.5 | C15—N2—C13 | 113.3 (2) |
C13—C14—H14B | 109.5 | C4—N3—C2 | 107.4 (2) |
H14A—C14—H14B | 108 | C4—N3—H3 | 125 (2) |
N2—C15—C16 | 110.8 (2) | C2—N3—H3 | 126 (2) |
N2—C15—H15A | 109.5 | C14—N4—C16 | 109.0 (2) |
C16—C15—H15A | 109.5 | C14—N4—C17 | 113.0 (2) |
N2—C15—H15B | 109.5 | C16—N4—C17 | 109.8 (2) |
C16—C15—H15B | 109.5 | C14—N4—HN4 | 108 (2) |
H15A—C15—H15B | 108.1 | C16—N4—HN4 | 108 (2) |
C15—C16—N4 | 111.2 (2) | C17—N4—HN4 | 109 (2) |
C15—C16—H16A | 109.4 | O5A—N5—O6A | 131 (2) |
N4—C16—H16A | 109.4 | O6B—N5—O5B | 121.0 (7) |
C15—C16—H16B | 109.4 | O5A—N5—C22 | 111.1 (18) |
N4—C16—H16B | 109.4 | O6B—N5—C22 | 117.5 (6) |
H16A—C16—H16B | 108 | O6A—N5—C22 | 117.2 (11) |
C18—C17—N4 | 115.0 (3) | O5B—N5—C22 | 121.4 (5) |
C18—C17—H17A | 108.5 | C18—O1—H1 | 106 (3) |
N4—C17—H17A | 108.5 | ||
O4—C4—C5—C6 | −7.5 (5) | C19—C25—C26—O3 | 172.6 (3) |
N3—C4—C5—C6 | 172.7 (3) | C19—C25—C26—O2 | −7.7 (4) |
O4—C4—C5—N1 | 176.9 (3) | N2—C2—N1—C5 | −177.5 (3) |
N3—C4—C5—N1 | −2.9 (3) | N3—C2—N1—C5 | −1.3 (3) |
N1—C5—C6—C7 | 1.7 (5) | C6—C5—N1—C2 | −172.7 (3) |
C4—C5—C6—C7 | −172.9 (3) | C4—C5—N1—C2 | 2.5 (3) |
C5—C6—C7—C8 | 14.1 (5) | N1—C2—N2—C15 | −162.1 (3) |
C5—C6—C7—C12 | −167.6 (3) | N3—C2—N2—C15 | 21.9 (5) |
C12—C7—C8—C9 | 1.7 (4) | N1—C2—N2—C13 | −8.1 (5) |
C6—C7—C8—C9 | −180.0 (3) | N3—C2—N2—C13 | 176.0 (3) |
C7—C8—C9—C10 | 1.3 (5) | C16—C15—N2—C2 | −149.5 (3) |
C8—C9—C10—C11 | −3.3 (5) | C16—C15—N2—C13 | 55.3 (4) |
C8—C9—C10—Cl1 | 177.5 (2) | C14—C13—N2—C2 | 148.2 (3) |
C9—C10—C11—C12 | 2.3 (5) | C14—C13—N2—C15 | −55.3 (3) |
Cl1—C10—C11—C12 | −178.6 (2) | O4—C4—N3—C2 | −177.8 (3) |
C10—C11—C12—C7 | 0.8 (5) | C5—C4—N3—C2 | 2.0 (3) |
C8—C7—C12—C11 | −2.8 (4) | N1—C2—N3—C4 | −0.5 (4) |
C6—C7—C12—C11 | 178.8 (3) | N2—C2—N3—C4 | 175.8 (3) |
N2—C13—C14—N4 | 56.6 (3) | C13—C14—N4—C16 | −57.9 (3) |
N2—C15—C16—N4 | −55.9 (3) | C13—C14—N4—C17 | 179.7 (2) |
N4—C17—C18—O1 | −71.1 (4) | C15—C16—N4—C14 | 57.5 (3) |
C24—C19—C20—C21 | −0.9 (5) | C15—C16—N4—C17 | −178.2 (2) |
C25—C19—C20—C21 | −178.8 (3) | C18—C17—N4—C14 | −68.3 (3) |
C19—C20—C21—C22 | 0.4 (5) | C18—C17—N4—C16 | 169.8 (3) |
C20—C21—C22—C23 | −0.1 (5) | C21—C22—N5—O5A | 156 (2) |
C20—C21—C22—N5 | −178.9 (3) | C23—C22—N5—O5A | −22 (2) |
C21—C22—C23—C24 | 0.2 (5) | C21—C22—N5—O6B | −1.1 (17) |
N5—C22—C23—C24 | 179.1 (3) | C23—C22—N5—O6B | −180.0 (16) |
C22—C23—C24—C19 | −0.7 (5) | C21—C22—N5—O6A | −30.0 (13) |
C20—C19—C24—C23 | 1.0 (4) | C23—C22—N5—O6A | 151.2 (13) |
C25—C19—C24—C23 | 179.0 (3) | C21—C22—N5—O5B | 174.1 (8) |
C20—C19—C25—C26 | 81.5 (4) | C23—C22—N5—O5B | −4.7 (9) |
C24—C19—C25—C26 | −96.4 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O5Ai | 0.93 | 2.54 | 3.41 (4) | 154 |
C11—H11···O5Bi | 0.93 | 2.55 | 3.37 (1) | 148 |
C13—H13A···O4ii | 0.97 | 2.67 | 3.242 (4) | 118 |
C14—H14A···O2 | 0.97 | 2.64 | 3.186 (4) | 116 |
C14—H14B···O4iii | 0.97 | 2.48 | 3.446 (4) | 177 |
C15—H15B···O2iv | 0.97 | 2.46 | 3.334 (3) | 150 |
C16—H16A···O3v | 0.97 | 2.52 | 3.416 (4) | 153 |
C17—H17B···O3v | 0.97 | 2.54 | 3.441 (4) | 155 |
C20—H20···O1vi | 0.93 | 2.78 | 3.624 (4) | 152 |
C24—H24···O6Aiv | 0.93 | 2.51 | 3.39 (3) | 159 |
C24—H24···O6Biv | 0.93 | 2.40 | 3.282 (9) | 158 |
C25—H25A···O6Biv | 0.97 | 2.68 | 3.505 (12) | 143 |
N3—H3···O2iv | 0.90 (4) | 1.89 (4) | 2.781 (3) | 168 (4) |
N4—HN4···O2 | 0.95 (4) | 2.53 (4) | 3.177 (3) | 125 (3) |
N4—HN4···O3 | 0.95 (4) | 1.82 (4) | 2.761 (3) | 168 (3) |
O1—H1···O2 | 0.94 (5) | 1.85 (5) | 2.762 (3) | 163 (5) |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x−1, y, z; (iii) −x+2, −y+2, −z+2; (iv) x+1, y, z; (v) −x+1, −y+3, −z+2; (vi) −x, −y+3, −z+2. |