Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804009894/na6309sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804009894/na6309Isup2.hkl |
CCDC reference: 242025
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- R factor = 0.054
- wR factor = 0.118
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... Cl1 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT416_ALERT_2_C Short Intra D-H..H-D H1C .. H6B .. 1.91 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N6 - H6C ... ? PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 2 N3 -CO1 -N1 -C1 10.30 1.40 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 8 N5 -CO1 -N2 -C4 40.00 4.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 13 N5 -CO1 -N2 -C3 -138.00 4.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 19 N1 -CO1 -N3 -C11 35.50 1.40 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 24 N1 -CO1 -N3 -C10 -107.10 1.20 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 30 N6 -CO1 -N4 -C12 75.00 4.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 35 N6 -CO1 -N4 -C13 -79.00 4.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 38 N2 -CO1 -N5 -C19 117.00 4.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 43 N2 -CO1 -N5 -C20 -61.00 4.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 46 N4 -CO1 -N6 -C22 -9.00 4.00 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 15 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 12 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL and WinGX (Farrugia, 1999).
[Co(C22H26N6O2)]ClO4 | F(000) = 1168 |
Mr = 564.87 | Dx = 1.575 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.728 (3) Å | Cell parameters from 897 reflections |
b = 17.232 (5) Å | θ = 2.2–23.3° |
c = 14.953 (5) Å | µ = 0.89 mm−1 |
β = 108.076 (6)° | T = 293 K |
V = 2382.8 (13) Å3 | Block, red |
Z = 4 | 0.32 × 0.24 × 0.20 mm |
Bruker SMART CCD area-detector diffractometer | 4873 independent reflections |
Radiation source: fine-focus sealed tube | 2884 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.064 |
φ and ω scans | θmax = 26.4°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→10 |
Tmin = 0.743, Tmax = 0.838 | k = −21→15 |
11184 measured reflections | l = −6→18 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0383P)2 + 1.7668P] where P = (Fo2 + 2Fc2)/3 |
4873 reflections | (Δ/σ)max = 0.001 |
325 parameters | Δρmax = 0.44 e Å−3 |
0 restraints | Δρmin = −0.37 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 | ||
Co1 | 0.66589 (6) | 0.24282 (3) | 0.43119 (3) | 0.02315 (16) | |
N1 | 0.7581 (4) | 0.31526 (19) | 0.5372 (2) | 0.0319 (9) | |
H1C | 0.7099 | 0.3101 | 0.5795 | 0.038* | |
H1D | 0.8485 | 0.2977 | 0.5652 | 0.038* | |
N2 | 0.5211 (4) | 0.32033 (18) | 0.3674 (2) | 0.0281 (8) | |
N3 | 0.5768 (3) | 0.18241 (18) | 0.31901 (19) | 0.0215 (7) | |
N4 | 0.7968 (3) | 0.27092 (18) | 0.3645 (2) | 0.0238 (7) | |
N5 | 0.8067 (4) | 0.16354 (19) | 0.4906 (2) | 0.0303 (8) | |
N6 | 0.5305 (4) | 0.2094 (2) | 0.5023 (2) | 0.0336 (9) | |
H6B | 0.5544 | 0.2373 | 0.5558 | 0.040* | |
H6C | 0.4414 | 0.2249 | 0.4680 | 0.040* | |
O1 | 0.5623 (3) | 0.18653 (17) | 0.16234 (17) | 0.0351 (7) | |
O2 | 0.8417 (3) | 0.24942 (18) | 0.22368 (17) | 0.0427 (8) | |
C1 | 0.7696 (5) | 0.3989 (3) | 0.5214 (3) | 0.0415 (12) | |
H1A | 0.8359 | 0.4073 | 0.4855 | 0.050* | |
H1B | 0.8084 | 0.4250 | 0.5815 | 0.050* | |
C2 | 0.6254 (5) | 0.4325 (3) | 0.4695 (3) | 0.0503 (13) | |
H2A | 0.6348 | 0.4885 | 0.4674 | 0.060* | |
H2B | 0.5588 | 0.4213 | 0.5045 | 0.060* | |
C3 | 0.5608 (5) | 0.4028 (2) | 0.3702 (3) | 0.0454 (12) | |
H3A | 0.4754 | 0.4331 | 0.3387 | 0.054* | |
H3B | 0.6301 | 0.4100 | 0.3362 | 0.054* | |
C4 | 0.3907 (5) | 0.3023 (3) | 0.3202 (3) | 0.0329 (10) | |
H4A | 0.3267 | 0.3430 | 0.2974 | 0.040* | |
C5 | 0.3339 (4) | 0.2239 (2) | 0.2991 (3) | 0.0297 (10) | |
C6 | 0.1867 (5) | 0.2087 (3) | 0.2773 (3) | 0.0408 (11) | |
H6A | 0.1233 | 0.2488 | 0.2785 | 0.049* | |
C7 | 0.1346 (5) | 0.1350 (3) | 0.2541 (3) | 0.0478 (13) | |
H7A | 0.0365 | 0.1247 | 0.2414 | 0.057* | |
C8 | 0.2288 (5) | 0.0763 (3) | 0.2497 (3) | 0.0486 (13) | |
H8A | 0.1929 | 0.0265 | 0.2328 | 0.058* | |
C9 | 0.3747 (5) | 0.0898 (3) | 0.2697 (3) | 0.0375 (11) | |
H9A | 0.4367 | 0.0498 | 0.2656 | 0.045* | |
C10 | 0.4281 (4) | 0.1637 (2) | 0.2960 (3) | 0.0269 (9) | |
C11 | 0.6249 (4) | 0.1999 (2) | 0.2469 (3) | 0.0234 (9) | |
C12 | 0.7676 (4) | 0.2430 (2) | 0.2765 (2) | 0.0263 (9) | |
C13 | 0.9420 (4) | 0.2897 (2) | 0.4139 (3) | 0.0280 (10) | |
C14 | 1.0138 (5) | 0.3520 (3) | 0.3911 (3) | 0.0348 (10) | |
H14A | 0.9670 | 0.3832 | 0.3400 | 0.042* | |
C15 | 1.1545 (5) | 0.3681 (3) | 0.4437 (3) | 0.0468 (13) | |
H15A | 1.2012 | 0.4109 | 0.4285 | 0.056* | |
C16 | 1.2262 (5) | 0.3217 (3) | 0.5182 (3) | 0.0508 (14) | |
H16A | 1.3204 | 0.3337 | 0.5541 | 0.061* | |
C17 | 1.1587 (5) | 0.2579 (3) | 0.5394 (3) | 0.0481 (13) | |
H17A | 1.2090 | 0.2253 | 0.5881 | 0.058* | |
C18 | 1.0142 (4) | 0.2410 (3) | 0.4884 (3) | 0.0331 (10) | |
C19 | 0.9430 (5) | 0.1732 (3) | 0.5103 (3) | 0.0392 (12) | |
H19A | 1.0020 | 0.1329 | 0.5417 | 0.047* | |
C20 | 0.7544 (5) | 0.0870 (2) | 0.5107 (3) | 0.0454 (13) | |
H20A | 0.8367 | 0.0538 | 0.5394 | 0.055* | |
H20B | 0.6982 | 0.0631 | 0.4519 | 0.055* | |
C21 | 0.6620 (6) | 0.0928 (3) | 0.5753 (3) | 0.0536 (14) | |
H21A | 0.6490 | 0.0412 | 0.5975 | 0.064* | |
H21B | 0.7127 | 0.1238 | 0.6297 | 0.064* | |
C22 | 0.5170 (6) | 0.1280 (3) | 0.5292 (3) | 0.0487 (13) | |
H22A | 0.4668 | 0.0982 | 0.4736 | 0.058* | |
H22B | 0.4600 | 0.1260 | 0.5721 | 0.058* | |
Cl1 | 0.16886 (15) | 0.48693 (7) | 0.19923 (8) | 0.0503 (3) | |
O3 | 0.2606 (6) | 0.4485 (3) | 0.1572 (3) | 0.1112 (18) | |
O4 | 0.0761 (7) | 0.4325 (3) | 0.2161 (4) | 0.153 (3) | |
O5 | 0.0913 (6) | 0.5437 (3) | 0.1394 (4) | 0.129 (2) | |
O6 | 0.2499 (6) | 0.5156 (3) | 0.2859 (4) | 0.148 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0281 (3) | 0.0271 (3) | 0.0151 (2) | 0.0020 (3) | 0.00779 (19) | 0.0011 (2) |
N1 | 0.041 (2) | 0.035 (2) | 0.0220 (17) | −0.0013 (17) | 0.0128 (16) | −0.0039 (16) |
N2 | 0.030 (2) | 0.024 (2) | 0.0303 (18) | 0.0021 (16) | 0.0087 (16) | 0.0010 (16) |
N3 | 0.0225 (18) | 0.0282 (19) | 0.0137 (15) | 0.0005 (14) | 0.0057 (13) | 0.0003 (14) |
N4 | 0.0238 (18) | 0.032 (2) | 0.0152 (15) | 0.0016 (14) | 0.0056 (13) | 0.0010 (14) |
N5 | 0.039 (2) | 0.030 (2) | 0.0202 (17) | 0.0051 (17) | 0.0055 (16) | 0.0015 (15) |
N6 | 0.041 (2) | 0.039 (2) | 0.0242 (17) | −0.0026 (17) | 0.0158 (16) | 0.0005 (16) |
O1 | 0.0306 (17) | 0.054 (2) | 0.0179 (14) | −0.0055 (14) | 0.0037 (12) | 0.0005 (13) |
O2 | 0.0360 (17) | 0.073 (2) | 0.0243 (14) | −0.0154 (17) | 0.0164 (13) | −0.0075 (16) |
C1 | 0.047 (3) | 0.033 (3) | 0.040 (3) | −0.001 (2) | 0.009 (2) | −0.010 (2) |
C2 | 0.051 (3) | 0.031 (3) | 0.065 (3) | 0.001 (2) | 0.012 (3) | −0.014 (2) |
C3 | 0.041 (3) | 0.026 (3) | 0.062 (3) | 0.003 (2) | 0.006 (2) | 0.008 (2) |
C4 | 0.032 (3) | 0.037 (3) | 0.029 (2) | 0.007 (2) | 0.0076 (19) | 0.003 (2) |
C5 | 0.029 (2) | 0.034 (3) | 0.026 (2) | −0.005 (2) | 0.0072 (18) | −0.0005 (18) |
C6 | 0.033 (3) | 0.052 (3) | 0.036 (3) | −0.001 (2) | 0.010 (2) | −0.001 (2) |
C7 | 0.026 (3) | 0.067 (4) | 0.049 (3) | −0.014 (3) | 0.011 (2) | 0.002 (3) |
C8 | 0.045 (3) | 0.046 (3) | 0.052 (3) | −0.020 (3) | 0.010 (2) | −0.005 (3) |
C9 | 0.044 (3) | 0.032 (3) | 0.035 (2) | 0.000 (2) | 0.010 (2) | −0.002 (2) |
C10 | 0.030 (2) | 0.034 (3) | 0.019 (2) | −0.004 (2) | 0.0093 (17) | 0.0019 (18) |
C11 | 0.025 (2) | 0.023 (2) | 0.022 (2) | 0.0053 (17) | 0.0066 (17) | 0.0018 (17) |
C12 | 0.024 (2) | 0.034 (3) | 0.0180 (18) | 0.0029 (19) | 0.0030 (15) | 0.0037 (19) |
C13 | 0.024 (2) | 0.038 (3) | 0.021 (2) | 0.0019 (19) | 0.0069 (17) | −0.0051 (18) |
C14 | 0.034 (3) | 0.039 (3) | 0.031 (2) | −0.004 (2) | 0.011 (2) | −0.005 (2) |
C15 | 0.034 (3) | 0.060 (3) | 0.046 (3) | −0.013 (2) | 0.013 (2) | −0.020 (3) |
C16 | 0.026 (3) | 0.072 (4) | 0.047 (3) | −0.008 (3) | 0.000 (2) | −0.020 (3) |
C17 | 0.035 (3) | 0.070 (4) | 0.031 (2) | 0.010 (3) | −0.0016 (19) | −0.011 (3) |
C18 | 0.027 (2) | 0.043 (3) | 0.026 (2) | 0.004 (2) | 0.0037 (17) | −0.004 (2) |
C19 | 0.043 (3) | 0.044 (3) | 0.023 (2) | 0.016 (2) | 0.000 (2) | 0.002 (2) |
C20 | 0.064 (4) | 0.024 (3) | 0.045 (3) | 0.006 (2) | 0.013 (3) | 0.011 (2) |
C21 | 0.085 (4) | 0.036 (3) | 0.042 (3) | −0.004 (3) | 0.022 (3) | 0.016 (2) |
C22 | 0.070 (4) | 0.043 (3) | 0.042 (3) | −0.011 (3) | 0.031 (3) | 0.004 (2) |
Cl1 | 0.0573 (8) | 0.0458 (8) | 0.0444 (7) | 0.0006 (7) | 0.0108 (6) | 0.0083 (6) |
O3 | 0.165 (5) | 0.102 (4) | 0.080 (3) | 0.075 (3) | 0.057 (3) | 0.022 (3) |
O4 | 0.171 (6) | 0.161 (5) | 0.128 (5) | −0.085 (5) | 0.048 (4) | 0.047 (4) |
O5 | 0.136 (5) | 0.139 (4) | 0.145 (4) | 0.092 (4) | 0.090 (4) | 0.102 (4) |
O6 | 0.128 (5) | 0.172 (5) | 0.114 (4) | −0.001 (4) | −0.003 (4) | −0.090 (4) |
Co1—N4 | 1.908 (3) | C6—C7 | 1.371 (6) |
Co1—N3 | 1.936 (3) | C6—H6A | 0.9300 |
Co1—N5 | 1.944 (3) | C7—C8 | 1.381 (7) |
Co1—N2 | 1.961 (3) | C7—H7A | 0.9300 |
Co1—N1 | 1.999 (3) | C8—C9 | 1.377 (6) |
Co1—N6 | 2.016 (3) | C8—H8A | 0.9300 |
N1—C1 | 1.471 (5) | C9—C10 | 1.386 (6) |
N1—H1C | 0.9000 | C9—H9A | 0.9300 |
N1—H1D | 0.9000 | C11—C12 | 1.515 (5) |
N2—C4 | 1.284 (5) | C13—C14 | 1.379 (6) |
N2—C3 | 1.470 (5) | C13—C18 | 1.397 (5) |
N3—C11 | 1.337 (4) | C14—C15 | 1.378 (6) |
N3—C10 | 1.416 (5) | C14—H14A | 0.9300 |
N4—C12 | 1.346 (4) | C15—C16 | 1.373 (7) |
N4—C13 | 1.413 (5) | C15—H15A | 0.9300 |
N5—C19 | 1.276 (5) | C16—C17 | 1.368 (7) |
N5—C20 | 1.478 (5) | C16—H16A | 0.9300 |
N6—C22 | 1.476 (5) | C17—C18 | 1.405 (6) |
N6—H6B | 0.9000 | C17—H17A | 0.9300 |
N6—H6C | 0.9000 | C18—C19 | 1.448 (6) |
O1—C11 | 1.242 (4) | C19—H19A | 0.9300 |
O2—C12 | 1.229 (4) | C20—C21 | 1.513 (6) |
C1—C2 | 1.494 (6) | C20—H20A | 0.9700 |
C1—H1A | 0.9700 | C20—H20B | 0.9700 |
C1—H1B | 0.9700 | C21—C22 | 1.494 (7) |
C2—C3 | 1.512 (6) | C21—H21A | 0.9700 |
C2—H2A | 0.9700 | C21—H21B | 0.9700 |
C2—H2B | 0.9700 | C22—H22A | 0.9700 |
C3—H3A | 0.9700 | C22—H22B | 0.9700 |
C3—H3B | 0.9700 | Cl1—O4 | 1.378 (5) |
C4—C5 | 1.456 (6) | Cl1—O5 | 1.381 (4) |
C4—H4A | 0.9300 | Cl1—O6 | 1.383 (4) |
C5—C6 | 1.391 (6) | Cl1—O3 | 1.406 (4) |
C5—C10 | 1.394 (6) | ||
N4—Co1—N3 | 82.87 (13) | C5—C6—H6A | 119.8 |
N4—Co1—N5 | 85.82 (14) | C6—C7—C8 | 119.5 (4) |
N3—Co1—N5 | 94.64 (13) | C6—C7—H7A | 120.3 |
N4—Co1—N2 | 93.90 (13) | C8—C7—H7A | 120.3 |
N3—Co1—N2 | 83.31 (13) | C9—C8—C7 | 121.3 (5) |
N5—Co1—N2 | 177.95 (14) | C9—C8—H8A | 119.3 |
N4—Co1—N1 | 92.74 (13) | C7—C8—H8A | 119.3 |
N3—Co1—N1 | 173.48 (13) | C8—C9—C10 | 119.2 (4) |
N5—Co1—N1 | 89.82 (14) | C8—C9—H9A | 120.4 |
N2—Co1—N1 | 92.22 (14) | C10—C9—H9A | 120.4 |
N4—Co1—N6 | 178.00 (14) | C9—C10—C5 | 120.1 (4) |
N3—Co1—N6 | 96.49 (13) | C9—C10—N3 | 122.8 (4) |
N5—Co1—N6 | 92.35 (15) | C5—C10—N3 | 117.1 (4) |
N2—Co1—N6 | 87.90 (14) | O1—C11—N3 | 126.6 (4) |
N1—Co1—N6 | 88.05 (14) | O1—C11—C12 | 120.2 (3) |
C1—N1—Co1 | 121.5 (2) | N3—C11—C12 | 113.1 (3) |
C1—N1—H1C | 107.0 | O2—C12—N4 | 127.5 (4) |
Co1—N1—H1C | 107.0 | O2—C12—C11 | 121.6 (3) |
C1—N1—H1D | 107.0 | N4—C12—C11 | 111.0 (3) |
Co1—N1—H1D | 107.0 | C14—C13—C18 | 119.7 (4) |
H1C—N1—H1D | 106.7 | C14—C13—N4 | 123.3 (4) |
C4—N2—C3 | 117.1 (3) | C18—C13—N4 | 116.9 (4) |
C4—N2—Co1 | 122.7 (3) | C15—C14—C13 | 120.4 (4) |
C3—N2—Co1 | 120.1 (3) | C15—C14—H14A | 119.8 |
C11—N3—C10 | 116.2 (3) | C13—C14—H14A | 119.8 |
C11—N3—Co1 | 113.8 (3) | C16—C15—C14 | 120.6 (5) |
C10—N3—Co1 | 118.8 (2) | C16—C15—H15A | 119.7 |
C12—N4—C13 | 117.8 (3) | C14—C15—H15A | 119.7 |
C12—N4—Co1 | 116.6 (3) | C17—C16—C15 | 119.8 (4) |
C13—N4—Co1 | 120.4 (2) | C17—C16—H16A | 120.1 |
C19—N5—C20 | 117.9 (4) | C15—C16—H16A | 120.1 |
C19—N5—Co1 | 123.3 (3) | C16—C17—C18 | 120.8 (4) |
C20—N5—Co1 | 118.8 (3) | C16—C17—H17A | 119.6 |
C22—N6—Co1 | 122.9 (3) | C18—C17—H17A | 119.6 |
C22—N6—H6B | 106.6 | C13—C18—C17 | 118.6 (4) |
Co1—N6—H6B | 106.6 | C13—C18—C19 | 120.5 (4) |
C22—N6—H6C | 106.6 | C17—C18—C19 | 120.8 (4) |
Co1—N6—H6C | 106.6 | N5—C19—C18 | 126.1 (4) |
H6B—N6—H6C | 106.6 | N5—C19—H19A | 117.0 |
N1—C1—C2 | 111.0 (4) | C18—C19—H19A | 117.0 |
N1—C1—H1A | 109.4 | N5—C20—C21 | 112.4 (4) |
C2—C1—H1A | 109.4 | N5—C20—H20A | 109.1 |
N1—C1—H1B | 109.4 | C21—C20—H20A | 109.1 |
C2—C1—H1B | 109.4 | N5—C20—H20B | 109.1 |
H1A—C1—H1B | 108.0 | C21—C20—H20B | 109.1 |
C1—C2—C3 | 114.6 (4) | H20A—C20—H20B | 107.9 |
C1—C2—H2A | 108.6 | C22—C21—C20 | 113.3 (4) |
C3—C2—H2A | 108.6 | C22—C21—H21A | 108.9 |
C1—C2—H2B | 108.6 | C20—C21—H21A | 108.9 |
C3—C2—H2B | 108.6 | C22—C21—H21B | 108.9 |
H2A—C2—H2B | 107.6 | C20—C21—H21B | 108.9 |
N2—C3—C2 | 112.4 (4) | H21A—C21—H21B | 107.7 |
N2—C3—H3A | 109.1 | N6—C22—C21 | 111.1 (4) |
C2—C3—H3A | 109.1 | N6—C22—H22A | 109.4 |
N2—C3—H3B | 109.1 | C21—C22—H22A | 109.4 |
C2—C3—H3B | 109.1 | N6—C22—H22B | 109.4 |
H3A—C3—H3B | 107.9 | C21—C22—H22B | 109.4 |
N2—C4—C5 | 126.0 (4) | H22A—C22—H22B | 108.0 |
N2—C4—H4A | 117.0 | O4—Cl1—O5 | 110.1 (4) |
C5—C4—H4A | 117.0 | O4—Cl1—O6 | 106.7 (4) |
C6—C5—C10 | 119.4 (4) | O5—Cl1—O6 | 113.0 (4) |
C6—C5—C4 | 121.3 (4) | O4—Cl1—O3 | 107.7 (4) |
C10—C5—C4 | 119.2 (4) | O5—Cl1—O3 | 109.8 (3) |
C7—C6—C5 | 120.5 (4) | O6—Cl1—O3 | 109.3 (4) |
C7—C6—H6A | 119.8 | ||
N4—Co1—N1—C1 | 57.8 (3) | C3—N2—C4—C5 | 172.3 (4) |
N3—Co1—N1—C1 | 10.3 (14) | Co1—N2—C4—C5 | −6.1 (6) |
N5—Co1—N1—C1 | 143.6 (3) | N2—C4—C5—C6 | 157.5 (4) |
N2—Co1—N1—C1 | −36.3 (3) | N2—C4—C5—C10 | −25.8 (6) |
N6—Co1—N1—C1 | −124.1 (3) | C10—C5—C6—C7 | 0.8 (6) |
N4—Co1—N2—C4 | 121.9 (3) | C4—C5—C6—C7 | 177.5 (4) |
N3—Co1—N2—C4 | 39.6 (3) | C5—C6—C7—C8 | −1.9 (7) |
N5—Co1—N2—C4 | 40 (4) | C6—C7—C8—C9 | 1.1 (7) |
N1—Co1—N2—C4 | −145.2 (3) | C7—C8—C9—C10 | 0.9 (7) |
N6—Co1—N2—C4 | −57.2 (3) | C8—C9—C10—C5 | −2.0 (6) |
N4—Co1—N2—C3 | −56.5 (3) | C8—C9—C10—N3 | 179.2 (4) |
N3—Co1—N2—C3 | −138.8 (3) | C6—C5—C10—C9 | 1.2 (6) |
N5—Co1—N2—C3 | −138 (4) | C4—C5—C10—C9 | −175.5 (4) |
N1—Co1—N2—C3 | 36.4 (3) | C6—C5—C10—N3 | −179.9 (3) |
N6—Co1—N2—C3 | 124.4 (3) | C4—C5—C10—N3 | 3.3 (5) |
N4—Co1—N3—C11 | −12.4 (3) | C11—N3—C10—C9 | 84.8 (5) |
N5—Co1—N3—C11 | −97.6 (3) | Co1—N3—C10—C9 | −133.5 (3) |
N2—Co1—N3—C11 | 82.4 (3) | C11—N3—C10—C5 | −94.0 (4) |
N1—Co1—N3—C11 | 35.5 (14) | Co1—N3—C10—C5 | 47.7 (4) |
N6—Co1—N3—C11 | 169.5 (3) | C10—N3—C11—O1 | −15.6 (6) |
N4—Co1—N3—C10 | −155.0 (3) | Co1—N3—C11—O1 | −159.2 (3) |
N5—Co1—N3—C10 | 119.8 (3) | C10—N3—C11—C12 | 161.7 (3) |
N2—Co1—N3—C10 | −60.2 (3) | Co1—N3—C11—C12 | 18.1 (4) |
N1—Co1—N3—C10 | −107.1 (12) | C13—N4—C12—O2 | −20.1 (6) |
N6—Co1—N3—C10 | 26.9 (3) | Co1—N4—C12—O2 | −174.8 (3) |
N3—Co1—N4—C12 | 3.4 (3) | C13—N4—C12—C11 | 159.7 (3) |
N5—Co1—N4—C12 | 98.6 (3) | Co1—N4—C12—C11 | 5.1 (4) |
N2—Co1—N4—C12 | −79.3 (3) | O1—C11—C12—O2 | −17.8 (6) |
N1—Co1—N4—C12 | −171.7 (3) | N3—C11—C12—O2 | 164.7 (4) |
N6—Co1—N4—C12 | 75 (4) | O1—C11—C12—N4 | 162.4 (3) |
N3—Co1—N4—C13 | −150.6 (3) | N3—C11—C12—N4 | −15.2 (5) |
N5—Co1—N4—C13 | −55.3 (3) | C12—N4—C13—C14 | 70.1 (5) |
N2—Co1—N4—C13 | 126.7 (3) | Co1—N4—C13—C14 | −136.2 (3) |
N1—Co1—N4—C13 | 34.3 (3) | C12—N4—C13—C18 | −108.9 (4) |
N6—Co1—N4—C13 | −79 (4) | Co1—N4—C13—C18 | 44.8 (4) |
N4—Co1—N5—C19 | 34.6 (3) | C18—C13—C14—C15 | −2.5 (6) |
N3—Co1—N5—C19 | 117.1 (3) | N4—C13—C14—C15 | 178.5 (4) |
N2—Co1—N5—C19 | 117 (4) | C13—C14—C15—C16 | 1.3 (7) |
N1—Co1—N5—C19 | −58.2 (3) | C14—C15—C16—C17 | 1.4 (7) |
N6—Co1—N5—C19 | −146.2 (3) | C15—C16—C17—C18 | −2.9 (7) |
N4—Co1—N5—C20 | −142.7 (3) | C14—C13—C18—C17 | 1.0 (6) |
N3—Co1—N5—C20 | −60.3 (3) | N4—C13—C18—C17 | −179.9 (4) |
N2—Co1—N5—C20 | −61 (4) | C14—C13—C18—C19 | −176.8 (4) |
N1—Co1—N5—C20 | 124.5 (3) | N4—C13—C18—C19 | 2.2 (5) |
N6—Co1—N5—C20 | 36.5 (3) | C16—C17—C18—C13 | 1.7 (6) |
N4—Co1—N6—C22 | −9 (4) | C16—C17—C18—C19 | 179.5 (4) |
N3—Co1—N6—C22 | 62.1 (3) | C20—N5—C19—C18 | 174.1 (4) |
N5—Co1—N6—C22 | −32.8 (3) | Co1—N5—C19—C18 | −3.2 (6) |
N2—Co1—N6—C22 | 145.1 (3) | C13—C18—C19—N5 | −24.4 (6) |
N1—Co1—N6—C22 | −122.6 (3) | C17—C18—C19—N5 | 157.7 (4) |
Co1—N1—C1—C2 | 53.4 (5) | C19—N5—C20—C21 | 123.0 (4) |
N1—C1—C2—C3 | −65.5 (5) | Co1—N5—C20—C21 | −59.5 (4) |
C4—N2—C3—C2 | 126.3 (4) | N5—C20—C21—C22 | 71.4 (5) |
Co1—N2—C3—C2 | −55.2 (5) | Co1—N6—C22—C21 | 48.9 (5) |
C1—C2—C3—N2 | 67.4 (5) | C20—C21—C22—N6 | −64.1 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1C···O1i | 0.90 | 2.17 | 3.057 (5) | 168 |
N1—H1C···O2i | 0.90 | 2.37 | 2.876 (4) | 115 |
N6—H6B···O1i | 0.90 | 2.05 | 2.929 (4) | 166 |
N1—H1D···O2i | 0.90 | 2.52 | 2.876 (4) | 104 |
C1—H1B···O6ii | 0.97 | 2.45 | 3.294 (8) | 145 |
C14—H14A···O4iii | 0.93 | 2.55 | 3.182 (8) | 126 |
C16—H16A···O1iv | 0.93 | 2.43 | 3.314 (5) | 158 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z+1; (iii) x+1, y, z; (iv) x+1, −y+1/2, z+1/2. |