Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805009529/hb6173sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805009529/hb6173Isup2.hkl |
CCDC reference: 270426
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
[CuCl(C12H8N2)2]NO3·C7H5NO4·H2O | Z = 2 |
Mr = 706.54 | F(000) = 722 |
Triclinic, P1 | Dx = 1.556 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.9326 (3) Å | Cell parameters from 6517 reflections |
b = 11.8986 (4) Å | θ = 2.5–27.4° |
c = 13.1517 (4) Å | µ = 0.88 mm−1 |
α = 82.7790 (11)° | T = 295 K |
β = 84.4600 (15)° | Chunk, blue |
γ = 78.7095 (12)° | 0.34 × 0.21 × 0.13 mm |
V = 1508.01 (8) Å3 |
Rigaku R-AXIS RAPID diffractometer | 6855 independent reflections |
Radiation source: fine-focus sealed tube | 5084 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 10.00 pixels mm-1 | θmax = 27.5°, θmin = 1.6° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −15→14 |
Tmin = 0.730, Tmax = 0.888 | l = −17→17 |
14700 measured reflections |
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)] = 0.045 | Hydrogen site location: difmap (O-H) and geom (C-H, N-H) |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0508P)2 + 0.7183P] where P = (Fo2 + 2Fc2)/3 |
6855 reflections | (Δ/σ)max = 0.001 |
453 parameters | Δρmax = 0.52 e Å−3 |
1 restraint | Δρmin = −0.46 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 | Occ. (<1) | |
Cu | 0.66401 (3) | 0.11830 (2) | 0.67736 (3) | 0.04476 (11) | |
Cl | 0.52248 (7) | 0.15673 (6) | 0.54047 (6) | 0.05734 (19) | |
O1 | 1.0418 (4) | 0.8728 (3) | 0.1363 (3) | 0.1285 (13) | |
O2 | 1.1093 (4) | 0.7622 (3) | 0.0190 (3) | 0.1379 (14) | |
O3 | 0.5919 (2) | 0.52222 (18) | 0.34100 (17) | 0.0689 (6) | |
H3A | 0.5427 | 0.4765 | 0.3694 | 0.050* | |
O4 | 0.7013 (3) | 0.3828 (2) | 0.2496 (2) | 0.0951 (9) | |
O5A | 0.2255 (9) | 0.3385 (7) | 0.3115 (6) | 0.087 (2) | 0.68 |
O6A | 0.2954 (6) | 0.4588 (5) | 0.1952 (4) | 0.1156 (18) | 0.68 |
O7A | 0.1730 (10) | 0.3481 (6) | 0.1562 (7) | 0.0755 (18) | 0.68 |
O5B | 0.263 (2) | 0.3207 (16) | 0.2807 (18) | 0.143 (9) | 0.32 |
O6B | 0.2017 (17) | 0.4919 (8) | 0.2578 (12) | 0.140 (5) | 0.32 |
O7B | 0.184 (3) | 0.382 (2) | 0.141 (2) | 0.174 (11) | 0.32 |
O1W | 0.4155 (2) | 0.39902 (18) | 0.42082 (18) | 0.0730 (6) | |
H1A | 0.3599 | 0.3795 | 0.3799 | 0.050* | |
H1B | 0.4484 | 0.3349 | 0.4511 | 0.050* | |
N1 | 0.7851 (2) | 0.22320 (17) | 0.60732 (17) | 0.0445 (5) | |
N2 | 0.8522 (2) | 0.00514 (17) | 0.68522 (16) | 0.0420 (5) | |
N3 | 0.5848 (2) | 0.21103 (17) | 0.80313 (17) | 0.0448 (5) | |
N4 | 0.5475 (2) | 0.01112 (17) | 0.75108 (17) | 0.0456 (5) | |
N5 | 1.0408 (3) | 0.7870 (3) | 0.0973 (3) | 0.0877 (9) | |
N6 | 0.2276 (3) | 0.3870 (3) | 0.2214 (3) | 0.0679 (7) | |
C1 | 0.7481 (3) | 0.3322 (2) | 0.5676 (2) | 0.0540 (7) | |
H1 | 0.6564 | 0.3680 | 0.5770 | 0.065* | |
C2 | 0.8408 (3) | 0.3944 (2) | 0.5127 (2) | 0.0563 (7) | |
H2 | 0.8112 | 0.4708 | 0.4869 | 0.068* | |
C3 | 0.9753 (3) | 0.3438 (2) | 0.4966 (2) | 0.0545 (7) | |
H3 | 1.0376 | 0.3847 | 0.4588 | 0.065* | |
C4 | 1.0188 (2) | 0.2287 (2) | 0.5376 (2) | 0.0453 (6) | |
C5 | 1.1578 (3) | 0.1671 (3) | 0.5264 (2) | 0.0564 (7) | |
H5 | 1.2252 | 0.2041 | 0.4907 | 0.068* | |
C6 | 1.1925 (3) | 0.0565 (3) | 0.5668 (2) | 0.0581 (7) | |
H6 | 1.2834 | 0.0185 | 0.5583 | 0.070* | |
C7 | 1.0924 (2) | −0.0034 (2) | 0.6225 (2) | 0.0469 (6) | |
C8 | 1.1205 (3) | −0.1193 (2) | 0.6657 (2) | 0.0583 (7) | |
H8 | 1.2091 | −0.1622 | 0.6585 | 0.070* | |
C9 | 1.0181 (3) | −0.1678 (2) | 0.7176 (2) | 0.0603 (8) | |
H9 | 1.0366 | −0.2438 | 0.7474 | 0.072* | |
C10 | 0.8841 (3) | −0.1032 (2) | 0.7265 (2) | 0.0509 (6) | |
H10 | 0.8150 | −0.1378 | 0.7627 | 0.061* | |
C11 | 0.9553 (2) | 0.0547 (2) | 0.63532 (18) | 0.0390 (5) | |
C12 | 0.9197 (2) | 0.1724 (2) | 0.59265 (18) | 0.0394 (5) | |
C13 | 0.6072 (3) | 0.3098 (2) | 0.8291 (2) | 0.0566 (7) | |
H13 | 0.6736 | 0.3455 | 0.7904 | 0.068* | |
C14 | 0.5347 (4) | 0.3619 (3) | 0.9124 (3) | 0.0686 (9) | |
H14 | 0.5534 | 0.4309 | 0.9287 | 0.082* | |
C15 | 0.4363 (4) | 0.3114 (3) | 0.9700 (2) | 0.0659 (8) | |
H15 | 0.3867 | 0.3463 | 1.0250 | 0.079* | |
C16 | 0.4106 (3) | 0.2067 (2) | 0.9459 (2) | 0.0522 (7) | |
C17 | 0.3112 (3) | 0.1458 (3) | 1.0014 (2) | 0.0644 (8) | |
H17 | 0.2585 | 0.1770 | 1.0570 | 0.077* | |
C18 | 0.2918 (3) | 0.0447 (3) | 0.9755 (2) | 0.0622 (8) | |
H18 | 0.2261 | 0.0073 | 1.0132 | 0.075* | |
C19 | 0.3712 (3) | −0.0063 (2) | 0.8904 (2) | 0.0524 (7) | |
C20 | 0.3582 (3) | −0.1123 (3) | 0.8589 (3) | 0.0615 (8) | |
H20 | 0.2946 | −0.1539 | 0.8938 | 0.074* | |
C21 | 0.4396 (3) | −0.1535 (3) | 0.7771 (3) | 0.0637 (8) | |
H21 | 0.4335 | −0.2244 | 0.7570 | 0.076* | |
C22 | 0.5317 (3) | −0.0890 (2) | 0.7239 (2) | 0.0569 (7) | |
H22 | 0.5844 | −0.1170 | 0.6670 | 0.068* | |
C23 | 0.4683 (2) | 0.0522 (2) | 0.8336 (2) | 0.0434 (6) | |
C24 | 0.4885 (2) | 0.1599 (2) | 0.8620 (2) | 0.0437 (6) | |
C25 | 0.6879 (3) | 0.4789 (2) | 0.2743 (2) | 0.0606 (8) | |
C26 | 0.7806 (3) | 0.5602 (2) | 0.2317 (2) | 0.0555 (7) | |
C27 | 0.7723 (3) | 0.6655 (2) | 0.2682 (2) | 0.0556 (7) | |
H27 | 0.7083 | 0.6865 | 0.3222 | 0.067* | |
C28 | 0.8580 (3) | 0.7395 (3) | 0.2253 (2) | 0.0604 (7) | |
H28 | 0.8529 | 0.8102 | 0.2499 | 0.072* | |
C29 | 0.9512 (3) | 0.7066 (3) | 0.1454 (3) | 0.0652 (8) | |
C30 | 0.9625 (4) | 0.6021 (3) | 0.1091 (3) | 0.0904 (12) | |
H30 | 1.0268 | 0.5812 | 0.0553 | 0.108* | |
C31 | 0.8780 (4) | 0.5292 (3) | 0.1531 (3) | 0.0857 (11) | |
H31 | 0.8861 | 0.4574 | 0.1298 | 0.103* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu | 0.03598 (16) | 0.03672 (16) | 0.0610 (2) | −0.01108 (12) | 0.00470 (13) | −0.00247 (13) |
Cl | 0.0499 (4) | 0.0525 (4) | 0.0710 (5) | −0.0136 (3) | −0.0149 (3) | 0.0028 (3) |
O1 | 0.164 (3) | 0.148 (3) | 0.106 (2) | −0.111 (3) | 0.006 (2) | −0.022 (2) |
O2 | 0.144 (3) | 0.152 (3) | 0.123 (3) | −0.075 (3) | 0.056 (2) | −0.016 (2) |
O3 | 0.0745 (14) | 0.0540 (12) | 0.0763 (15) | −0.0166 (10) | 0.0102 (12) | −0.0040 (10) |
O4 | 0.0972 (18) | 0.0516 (13) | 0.136 (2) | −0.0184 (13) | 0.0248 (17) | −0.0264 (14) |
O5A | 0.106 (4) | 0.099 (6) | 0.063 (3) | −0.053 (4) | 0.009 (3) | 0.001 (3) |
O6A | 0.163 (5) | 0.102 (4) | 0.103 (4) | −0.094 (4) | 0.014 (3) | −0.003 (3) |
O7A | 0.096 (4) | 0.071 (2) | 0.067 (4) | −0.031 (3) | −0.002 (3) | −0.014 (2) |
O5B | 0.20 (2) | 0.048 (6) | 0.18 (2) | 0.011 (9) | −0.106 (16) | −0.013 (11) |
O6B | 0.196 (14) | 0.062 (6) | 0.172 (13) | −0.018 (7) | −0.071 (10) | −0.021 (7) |
O7B | 0.117 (14) | 0.29 (3) | 0.081 (12) | 0.068 (16) | 0.009 (10) | −0.049 (17) |
O1W | 0.0798 (15) | 0.0560 (12) | 0.0826 (16) | −0.0174 (11) | −0.0133 (12) | 0.0077 (11) |
N1 | 0.0346 (10) | 0.0380 (10) | 0.0605 (14) | −0.0089 (8) | −0.0010 (9) | −0.0018 (9) |
N2 | 0.0405 (10) | 0.0378 (10) | 0.0476 (12) | −0.0073 (9) | −0.0031 (9) | −0.0051 (9) |
N3 | 0.0443 (11) | 0.0378 (10) | 0.0521 (13) | −0.0091 (9) | −0.0012 (9) | −0.0037 (9) |
N4 | 0.0416 (11) | 0.0378 (11) | 0.0580 (14) | −0.0127 (9) | −0.0006 (10) | −0.0008 (9) |
N5 | 0.083 (2) | 0.109 (3) | 0.076 (2) | −0.040 (2) | −0.0062 (17) | 0.007 (2) |
N6 | 0.0681 (18) | 0.0607 (18) | 0.073 (2) | −0.0199 (16) | 0.0073 (16) | 0.0011 (17) |
C1 | 0.0430 (14) | 0.0415 (13) | 0.076 (2) | −0.0093 (11) | −0.0039 (13) | 0.0027 (13) |
C2 | 0.0603 (17) | 0.0403 (13) | 0.0695 (19) | −0.0177 (12) | −0.0065 (14) | 0.0043 (13) |
C3 | 0.0542 (16) | 0.0588 (16) | 0.0544 (17) | −0.0267 (14) | 0.0018 (13) | −0.0008 (13) |
C4 | 0.0408 (13) | 0.0537 (14) | 0.0449 (15) | −0.0166 (11) | 0.0014 (11) | −0.0106 (12) |
C5 | 0.0393 (13) | 0.0722 (19) | 0.0608 (18) | −0.0193 (13) | 0.0092 (12) | −0.0155 (15) |
C6 | 0.0335 (13) | 0.073 (2) | 0.0684 (19) | −0.0060 (13) | 0.0045 (12) | −0.0218 (16) |
C7 | 0.0391 (13) | 0.0488 (14) | 0.0537 (16) | −0.0020 (11) | −0.0071 (11) | −0.0162 (12) |
C8 | 0.0452 (14) | 0.0542 (16) | 0.075 (2) | 0.0043 (13) | −0.0136 (14) | −0.0175 (14) |
C9 | 0.0627 (18) | 0.0418 (14) | 0.074 (2) | 0.0013 (13) | −0.0189 (15) | −0.0041 (14) |
C10 | 0.0554 (15) | 0.0422 (13) | 0.0541 (17) | −0.0082 (12) | −0.0060 (12) | −0.0019 (12) |
C11 | 0.0354 (11) | 0.0430 (12) | 0.0408 (13) | −0.0079 (10) | −0.0041 (10) | −0.0106 (10) |
C12 | 0.0350 (11) | 0.0437 (12) | 0.0416 (14) | −0.0109 (10) | −0.0017 (10) | −0.0081 (10) |
C13 | 0.0637 (17) | 0.0472 (15) | 0.0606 (19) | −0.0158 (13) | −0.0025 (14) | −0.0060 (13) |
C14 | 0.094 (2) | 0.0483 (16) | 0.067 (2) | −0.0170 (16) | −0.0012 (18) | −0.0178 (15) |
C15 | 0.082 (2) | 0.0589 (18) | 0.0515 (18) | −0.0035 (16) | 0.0043 (16) | −0.0091 (14) |
C16 | 0.0555 (15) | 0.0532 (15) | 0.0427 (15) | −0.0020 (13) | −0.0032 (12) | 0.0019 (12) |
C17 | 0.0586 (17) | 0.079 (2) | 0.0465 (17) | −0.0049 (16) | 0.0068 (13) | 0.0079 (15) |
C18 | 0.0497 (15) | 0.073 (2) | 0.0575 (19) | −0.0146 (14) | 0.0042 (13) | 0.0172 (15) |
C19 | 0.0413 (13) | 0.0536 (15) | 0.0589 (17) | −0.0120 (12) | −0.0063 (12) | 0.0147 (13) |
C20 | 0.0513 (16) | 0.0588 (17) | 0.076 (2) | −0.0263 (14) | −0.0124 (15) | 0.0191 (15) |
C21 | 0.0654 (18) | 0.0454 (15) | 0.085 (2) | −0.0246 (14) | −0.0164 (17) | 0.0043 (15) |
C22 | 0.0559 (16) | 0.0458 (15) | 0.071 (2) | −0.0159 (13) | −0.0025 (14) | −0.0054 (13) |
C23 | 0.0358 (12) | 0.0420 (13) | 0.0505 (15) | −0.0088 (10) | −0.0058 (11) | 0.0068 (11) |
C24 | 0.0389 (12) | 0.0429 (13) | 0.0456 (15) | −0.0032 (10) | −0.0054 (10) | 0.0038 (11) |
C25 | 0.0653 (18) | 0.0440 (15) | 0.068 (2) | −0.0028 (13) | −0.0069 (15) | 0.0011 (14) |
C26 | 0.0582 (16) | 0.0470 (15) | 0.0581 (18) | −0.0030 (13) | −0.0064 (13) | −0.0026 (13) |
C27 | 0.0596 (16) | 0.0585 (17) | 0.0495 (17) | −0.0119 (14) | −0.0046 (13) | −0.0068 (13) |
C28 | 0.0716 (19) | 0.0601 (17) | 0.0538 (18) | −0.0198 (15) | −0.0146 (15) | −0.0035 (14) |
C29 | 0.0592 (18) | 0.077 (2) | 0.061 (2) | −0.0230 (16) | −0.0057 (15) | 0.0036 (16) |
C30 | 0.091 (3) | 0.083 (3) | 0.092 (3) | −0.017 (2) | 0.031 (2) | −0.019 (2) |
C31 | 0.095 (3) | 0.062 (2) | 0.096 (3) | −0.0128 (19) | 0.026 (2) | −0.0222 (19) |
Cu—Cl | 2.3359 (8) | C7—C11 | 1.405 (3) |
Cu—N1 | 1.985 (2) | C7—C8 | 1.409 (4) |
Cu—N2 | 2.0823 (19) | C8—C9 | 1.353 (4) |
Cu—N3 | 2.107 (2) | C8—H8 | 0.9300 |
Cu—N4 | 1.989 (2) | C9—C10 | 1.403 (4) |
O1—N5 | 1.201 (4) | C9—H9 | 0.9300 |
O2—N5 | 1.213 (4) | C10—H10 | 0.9300 |
O3—C25 | 1.305 (4) | C11—C12 | 1.431 (3) |
O3—H3A | 0.8324 | C13—C14 | 1.395 (4) |
O4—C25 | 1.207 (4) | C13—H13 | 0.9300 |
O5A—N6 | 1.250 (9) | C14—C15 | 1.365 (5) |
O6A—N6 | 1.187 (5) | C14—H14 | 0.9300 |
O7A—N6 | 1.237 (10) | C15—C16 | 1.399 (4) |
O5B—N6 | 1.07 (2) | C15—H15 | 0.9300 |
O6B—N6 | 1.361 (11) | C16—C24 | 1.395 (4) |
O7B—N6 | 1.19 (3) | C16—C17 | 1.429 (4) |
O1W—H1A | 0.8868 | C17—C18 | 1.345 (5) |
O1W—H1B | 0.8363 | C17—H17 | 0.9300 |
N1—C1 | 1.330 (3) | C18—C19 | 1.434 (4) |
N1—C12 | 1.361 (3) | C18—H18 | 0.9300 |
N2—C10 | 1.325 (3) | C19—C23 | 1.402 (3) |
N2—C11 | 1.355 (3) | C19—C20 | 1.408 (4) |
N3—C13 | 1.328 (3) | C20—C21 | 1.364 (5) |
N3—C24 | 1.360 (3) | C20—H20 | 0.9300 |
N4—C22 | 1.327 (3) | C21—C22 | 1.390 (4) |
N4—C23 | 1.362 (3) | C21—H21 | 0.9300 |
N5—C29 | 1.476 (4) | C22—H22 | 0.9300 |
C1—C2 | 1.387 (4) | C23—C24 | 1.434 (4) |
C1—H1 | 0.9300 | C25—C26 | 1.487 (4) |
C2—C3 | 1.362 (4) | C26—C31 | 1.380 (4) |
C2—H2 | 0.9300 | C26—C27 | 1.382 (4) |
C3—C4 | 1.407 (4) | C27—C28 | 1.376 (4) |
C3—H3 | 0.9300 | C27—H27 | 0.9300 |
C4—C12 | 1.393 (3) | C28—C29 | 1.374 (4) |
C4—C5 | 1.435 (4) | C28—H28 | 0.9300 |
C5—C6 | 1.347 (4) | C29—C30 | 1.367 (5) |
C5—H5 | 0.9300 | C30—C31 | 1.363 (5) |
C6—C7 | 1.428 (4) | C30—H30 | 0.9300 |
C6—H6 | 0.9300 | C31—H31 | 0.9300 |
Cl—Cu—N1 | 91.45 (7) | N2—C11—C7 | 123.7 (2) |
Cl—Cu—N2 | 126.90 (6) | N2—C11—C12 | 117.0 (2) |
Cl—Cu—N3 | 113.78 (6) | C7—C11—C12 | 119.3 (2) |
Cl—Cu—N4 | 90.50 (7) | N1—C12—C4 | 123.1 (2) |
N1—Cu—N2 | 81.21 (8) | N1—C12—C11 | 116.2 (2) |
N1—Cu—N3 | 98.67 (8) | C4—C12—C11 | 120.6 (2) |
N1—Cu—N4 | 178.01 (9) | N3—C13—C14 | 122.4 (3) |
N2—Cu—N3 | 119.32 (8) | N3—C13—H13 | 118.8 |
N2—Cu—N4 | 97.30 (8) | C14—C13—H13 | 118.8 |
N3—Cu—N4 | 80.88 (8) | C15—C14—C13 | 119.8 (3) |
C25—O3—H3A | 114.7 | C15—C14—H14 | 120.1 |
H1A—O1W—H1B | 101.5 | C13—C14—H14 | 120.1 |
C1—N1—C12 | 117.8 (2) | C14—C15—C16 | 119.6 (3) |
C1—N1—Cu | 127.63 (17) | C14—C15—H15 | 120.2 |
C12—N1—Cu | 114.34 (15) | C16—C15—H15 | 120.2 |
C10—N2—C11 | 117.7 (2) | C24—C16—C15 | 116.9 (3) |
C10—N2—Cu | 131.30 (18) | C24—C16—C17 | 118.8 (3) |
C11—N2—Cu | 110.96 (15) | C15—C16—C17 | 124.3 (3) |
C13—N3—C24 | 117.5 (2) | C18—C17—C16 | 121.8 (3) |
C13—N3—Cu | 131.54 (19) | C18—C17—H17 | 119.1 |
C24—N3—Cu | 110.79 (16) | C16—C17—H17 | 119.1 |
C22—N4—C23 | 118.2 (2) | C17—C18—C19 | 120.8 (3) |
C22—N4—Cu | 127.3 (2) | C17—C18—H18 | 119.6 |
C23—N4—Cu | 114.32 (16) | C19—C18—H18 | 119.6 |
O1—N5—O2 | 123.6 (4) | C23—C19—C20 | 117.0 (3) |
O1—N5—C29 | 119.1 (4) | C23—C19—C18 | 118.7 (3) |
O2—N5—C29 | 117.3 (4) | C20—C19—C18 | 124.3 (3) |
O5B—N6—O7B | 131.3 (18) | C21—C20—C19 | 119.6 (3) |
O6A—N6—O7A | 119.6 (5) | C21—C20—H20 | 120.2 |
O6A—N6—O5A | 121.1 (6) | C19—C20—H20 | 120.2 |
O7A—N6—O5A | 118.6 (6) | C20—C21—C22 | 119.7 (3) |
O5B—N6—O6B | 110.3 (13) | C20—C21—H21 | 120.2 |
O7B—N6—O6B | 116.7 (14) | C22—C21—H21 | 120.2 |
N1—C1—C2 | 122.5 (2) | N4—C22—C21 | 122.6 (3) |
N1—C1—H1 | 118.7 | N4—C22—H22 | 118.7 |
C2—C1—H1 | 118.7 | C21—C22—H22 | 118.7 |
C3—C2—C1 | 120.0 (3) | N4—C23—C19 | 122.9 (2) |
C3—C2—H2 | 120.0 | N4—C23—C24 | 117.0 (2) |
C1—C2—H2 | 120.0 | C19—C23—C24 | 120.2 (2) |
C2—C3—C4 | 119.2 (2) | N3—C24—C16 | 123.7 (2) |
C2—C3—H3 | 120.4 | N3—C24—C23 | 116.5 (2) |
C4—C3—H3 | 120.4 | C16—C24—C23 | 119.8 (2) |
C12—C4—C3 | 117.3 (2) | O4—C25—O3 | 124.0 (3) |
C12—C4—C5 | 118.7 (2) | O4—C25—C26 | 123.0 (3) |
C3—C4—C5 | 124.0 (2) | O3—C25—C26 | 113.0 (3) |
C6—C5—C4 | 121.1 (3) | C31—C26—C27 | 119.1 (3) |
C6—C5—H5 | 119.4 | C31—C26—C25 | 118.7 (3) |
C4—C5—H5 | 119.4 | C27—C26—C25 | 122.2 (3) |
C5—C6—C7 | 121.2 (2) | C28—C27—C26 | 120.5 (3) |
C5—C6—H6 | 119.4 | C28—C27—H27 | 119.8 |
C7—C6—H6 | 119.4 | C26—C27—H27 | 119.8 |
C11—C7—C8 | 116.4 (2) | C29—C28—C27 | 118.6 (3) |
C11—C7—C6 | 119.1 (2) | C29—C28—H28 | 120.7 |
C8—C7—C6 | 124.5 (2) | C27—C28—H28 | 120.7 |
C9—C8—C7 | 119.8 (2) | C30—C29—C28 | 121.8 (3) |
C9—C8—H8 | 120.1 | C30—C29—N5 | 119.3 (3) |
C7—C8—H8 | 120.1 | C28—C29—N5 | 118.8 (3) |
C8—C9—C10 | 119.9 (3) | C31—C30—C29 | 118.9 (3) |
C8—C9—H9 | 120.1 | C31—C30—H30 | 120.6 |
C10—C9—H9 | 120.1 | C29—C30—H30 | 120.6 |
N2—C10—C9 | 122.5 (3) | C30—C31—C26 | 121.1 (3) |
N2—C10—H10 | 118.8 | C30—C31—H31 | 119.5 |
C9—C10—H10 | 118.8 | C26—C31—H31 | 119.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···O1W | 0.83 | 1.74 | 2.566 (3) | 170 |
O1W—H1A···O5A | 0.89 | 1.85 | 2.73 (1) | 172 |
O1W—H1A···O5B | 0.89 | 1.96 | 2.84 (3) | 171 |
O1W—H1B···Cl | 0.84 | 2.31 | 3.146 (2) | 176 |