The title complex, [ZnCl2(C16H17NO2)2], displays a distorted tetrahedral coordination geometry around the ZnII ion. The Schiff base inner salt, (benzylimino)ethyl-5-methoxyphenol, coordinates in a monodentate manner to the ZnII ion via the deprotonated hydroxy groups. The protonated imino groups form intramolecular hydrogen bonds with the deprotonated hydroxyl groups of the same Schiff base ligand.
Supporting information
CCDC reference: 613864
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- R factor = 0.042
- wR factor = 0.119
- Data-to-parameter ratio = 15.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.80 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C15
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C26
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C30
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Zn1
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C27
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C11 -C16 1.37 Ang.
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C27 -C32 1.36 Ang.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
10 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
9 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL'.
Bis{2-[1-(benzylimino)ethyl]-5-methoxyphenol}dichlorozinc(II)
top
Crystal data top
[ZnCl2(C16H17NO2)2] | F(000) = 1344 |
Mr = 646.88 | Dx = 1.375 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3722 reflections |
a = 11.1785 (18) Å | θ = 2.2–24.7° |
b = 16.082 (3) Å | µ = 1.00 mm−1 |
c = 17.555 (3) Å | T = 298 K |
β = 97.928 (3)° | Prism, colorless |
V = 3125.7 (9) Å3 | 0.49 × 0.45 × 0.40 mm |
Z = 4 | |
Data collection top
Bruker APEX area-dectector diffractometer | 5827 independent reflections |
Radiation source: fine-focus sealed tube | 3546 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
φ and ω scans | θmax = 25.5°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −13→9 |
Tmin = 0.618, Tmax = 0.670 | k = −19→18 |
16847 measured reflections | l = −18→21 |
Refinement top
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0436P)2 + 1.2861P] where P = (Fo2 + 2Fc2)/3 |
5827 reflections | (Δ/σ)max = 0.001 |
374 parameters | Δρmax = 0.46 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Zn1 | 0.29374 (4) | 0.09695 (2) | 0.23116 (2) | 0.04291 (15) | |
Cl1 | 0.47070 (9) | 0.10392 (6) | 0.18634 (6) | 0.0641 (3) | |
Cl2 | 0.12456 (10) | 0.11924 (6) | 0.15182 (6) | 0.0697 (3) | |
N1 | 0.4291 (3) | 0.30481 (18) | 0.36804 (18) | 0.0508 (8) | |
H1 | 0.3970 | 0.2574 | 0.3378 | 0.076* | |
N2 | 0.1462 (3) | −0.14823 (19) | 0.2369 (2) | 0.0589 (9) | |
H2 | 0.1585 | −0.0890 | 0.2300 | 0.088* | |
O1 | 0.3161 (2) | 0.17401 (14) | 0.31878 (13) | 0.0501 (6) | |
O2 | −0.0102 (3) | 0.0823 (2) | 0.44542 (18) | 0.0821 (9) | |
O3 | 0.2675 (2) | −0.01628 (13) | 0.27106 (14) | 0.0507 (7) | |
O4 | 0.6306 (3) | −0.0392 (2) | 0.44718 (18) | 0.0862 (10) | |
C1 | 0.3787 (4) | 0.3823 (2) | 0.4771 (2) | 0.0674 (12) | |
H1A | 0.4350 | 0.4208 | 0.4600 | 0.101* | |
H1B | 0.4101 | 0.3619 | 0.5273 | 0.101* | |
H1C | 0.3031 | 0.4099 | 0.4793 | 0.101* | |
C2 | 0.3596 (3) | 0.3109 (2) | 0.4219 (2) | 0.0466 (9) | |
C3 | 0.2677 (3) | 0.2492 (2) | 0.4269 (2) | 0.0437 (9) | |
C4 | 0.2475 (3) | 0.1829 (2) | 0.3732 (2) | 0.0441 (9) | |
C5 | 0.1533 (3) | 0.1272 (2) | 0.3791 (2) | 0.0527 (10) | |
H5 | 0.1379 | 0.0847 | 0.3431 | 0.063* | |
C6 | 0.0835 (4) | 0.1337 (3) | 0.4365 (2) | 0.0584 (11) | |
C7 | 0.1044 (4) | 0.1975 (3) | 0.4915 (2) | 0.0615 (11) | |
H7 | 0.0574 | 0.2015 | 0.5312 | 0.074* | |
C8 | 0.1932 (4) | 0.2526 (3) | 0.4860 (2) | 0.0552 (10) | |
H8 | 0.2063 | 0.2947 | 0.5224 | 0.066* | |
C9 | −0.0315 (5) | 0.0133 (3) | 0.3932 (3) | 0.1003 (18) | |
H9A | −0.0497 | 0.0337 | 0.3415 | 0.150* | |
H9B | −0.0984 | −0.0189 | 0.4060 | 0.150* | |
H9C | 0.0394 | −0.0211 | 0.3974 | 0.150* | |
C10 | 0.5236 (4) | 0.3619 (2) | 0.3527 (2) | 0.0612 (11) | |
H10A | 0.4939 | 0.4184 | 0.3550 | 0.073* | |
H10B | 0.5414 | 0.3523 | 0.3009 | 0.073* | |
C11 | 0.6385 (3) | 0.3537 (2) | 0.4079 (2) | 0.0541 (10) | |
C12 | 0.7082 (4) | 0.4230 (3) | 0.4273 (3) | 0.0667 (12) | |
H12 | 0.6829 | 0.4746 | 0.4072 | 0.080* | |
C13 | 0.8150 (4) | 0.4163 (3) | 0.4762 (3) | 0.0816 (14) | |
H13 | 0.8616 | 0.4636 | 0.4883 | 0.098* | |
C14 | 0.8534 (4) | 0.3423 (4) | 0.5069 (3) | 0.0909 (16) | |
H14 | 0.9254 | 0.3386 | 0.5403 | 0.109* | |
C15 | 0.7849 (5) | 0.2733 (4) | 0.4882 (4) | 0.113 (2) | |
H15 | 0.8103 | 0.2221 | 0.5090 | 0.135* | |
C16 | 0.6782 (4) | 0.2790 (3) | 0.4387 (3) | 0.0879 (16) | |
H16 | 0.6328 | 0.2313 | 0.4260 | 0.105* | |
C17 | 0.2157 (5) | −0.2843 (3) | 0.2825 (3) | 0.1030 (19) | |
H17A | 0.1588 | −0.2986 | 0.3166 | 0.155* | |
H17B | 0.2928 | −0.3085 | 0.3009 | 0.155* | |
H17C | 0.1876 | −0.3053 | 0.2320 | 0.155* | |
C18 | 0.2281 (4) | −0.1907 (2) | 0.2792 (2) | 0.0557 (10) | |
C19 | 0.3291 (3) | −0.1488 (2) | 0.3218 (2) | 0.0501 (10) | |
C20 | 0.3453 (3) | −0.0610 (2) | 0.3166 (2) | 0.0428 (9) | |
C21 | 0.4466 (3) | −0.0241 (2) | 0.3592 (2) | 0.0488 (9) | |
H21 | 0.4572 | 0.0331 | 0.3565 | 0.059* | |
C22 | 0.5298 (4) | −0.0706 (3) | 0.4045 (2) | 0.0601 (11) | |
C23 | 0.5165 (4) | −0.1559 (3) | 0.4092 (3) | 0.0762 (14) | |
H23 | 0.5747 | −0.1874 | 0.4393 | 0.091* | |
C24 | 0.4189 (4) | −0.1931 (3) | 0.3699 (3) | 0.0715 (13) | |
H24 | 0.4103 | −0.2503 | 0.3747 | 0.086* | |
C25 | 0.6517 (4) | 0.0472 (3) | 0.4445 (3) | 0.0897 (16) | |
H25A | 0.6615 | 0.0630 | 0.3930 | 0.135* | |
H25B | 0.7236 | 0.0608 | 0.4787 | 0.135* | |
H25C | 0.5842 | 0.0765 | 0.4601 | 0.135* | |
C26 | 0.0353 (4) | −0.1775 (3) | 0.1897 (3) | 0.0787 (14) | |
H26A | 0.0240 | −0.2362 | 0.1991 | 0.094* | |
H26B | 0.0427 | −0.1705 | 0.1357 | 0.094* | |
C27 | −0.0723 (4) | −0.1297 (2) | 0.2084 (2) | 0.0524 (10) | |
C28 | −0.1043 (5) | −0.0562 (3) | 0.1728 (3) | 0.0766 (14) | |
H28 | −0.0586 | −0.0351 | 0.1368 | 0.092* | |
C29 | −0.2036 (7) | −0.0129 (4) | 0.1895 (4) | 0.108 (2) | |
H29 | −0.2262 | 0.0366 | 0.1640 | 0.129* | |
C30 | −0.2680 (6) | −0.0427 (5) | 0.2434 (5) | 0.120 (3) | |
H30 | −0.3344 | −0.0133 | 0.2555 | 0.144* | |
C31 | −0.2362 (5) | −0.1154 (5) | 0.2796 (3) | 0.0990 (19) | |
H31 | −0.2811 | −0.1358 | 0.3163 | 0.119* | |
C32 | −0.1388 (5) | −0.1587 (3) | 0.2624 (3) | 0.0704 (13) | |
H32 | −0.1174 | −0.2084 | 0.2877 | 0.085* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.0530 (3) | 0.0355 (2) | 0.0389 (2) | 0.0015 (2) | 0.00188 (18) | −0.00023 (19) |
Cl1 | 0.0606 (7) | 0.0678 (7) | 0.0661 (7) | −0.0070 (5) | 0.0169 (5) | −0.0011 (5) |
Cl2 | 0.0670 (7) | 0.0671 (7) | 0.0673 (7) | −0.0001 (5) | −0.0178 (6) | 0.0145 (5) |
N1 | 0.054 (2) | 0.0464 (18) | 0.048 (2) | −0.0033 (15) | −0.0038 (16) | −0.0040 (15) |
N2 | 0.058 (2) | 0.0448 (18) | 0.074 (2) | −0.0037 (17) | 0.0121 (18) | −0.0070 (17) |
O1 | 0.0597 (17) | 0.0463 (14) | 0.0455 (15) | −0.0017 (12) | 0.0113 (13) | −0.0136 (12) |
O2 | 0.069 (2) | 0.106 (2) | 0.074 (2) | −0.0251 (19) | 0.0192 (17) | 0.0006 (19) |
O3 | 0.0559 (16) | 0.0354 (13) | 0.0576 (17) | 0.0030 (12) | −0.0036 (13) | 0.0079 (12) |
O4 | 0.070 (2) | 0.098 (3) | 0.083 (2) | 0.0092 (19) | −0.0151 (18) | 0.009 (2) |
C1 | 0.077 (3) | 0.060 (3) | 0.062 (3) | 0.001 (2) | −0.003 (2) | −0.019 (2) |
C2 | 0.052 (2) | 0.048 (2) | 0.037 (2) | 0.0136 (19) | −0.0047 (18) | −0.0005 (17) |
C3 | 0.048 (2) | 0.043 (2) | 0.038 (2) | 0.0102 (18) | −0.0007 (17) | −0.0014 (16) |
C4 | 0.050 (2) | 0.044 (2) | 0.037 (2) | 0.0113 (18) | 0.0003 (17) | 0.0011 (17) |
C5 | 0.055 (3) | 0.059 (2) | 0.044 (2) | 0.000 (2) | 0.0042 (19) | −0.0055 (18) |
C6 | 0.051 (3) | 0.067 (3) | 0.056 (3) | −0.003 (2) | 0.001 (2) | 0.003 (2) |
C7 | 0.054 (3) | 0.082 (3) | 0.051 (3) | 0.007 (2) | 0.015 (2) | −0.004 (2) |
C8 | 0.057 (3) | 0.064 (3) | 0.043 (2) | 0.014 (2) | 0.0021 (19) | −0.0120 (19) |
C9 | 0.106 (4) | 0.110 (4) | 0.084 (4) | −0.049 (3) | 0.010 (3) | −0.009 (3) |
C10 | 0.070 (3) | 0.059 (2) | 0.053 (3) | −0.009 (2) | 0.002 (2) | 0.004 (2) |
C11 | 0.055 (3) | 0.052 (2) | 0.056 (3) | −0.005 (2) | 0.009 (2) | 0.0026 (19) |
C12 | 0.075 (3) | 0.054 (3) | 0.069 (3) | −0.002 (2) | 0.002 (2) | −0.008 (2) |
C13 | 0.072 (3) | 0.084 (4) | 0.086 (4) | −0.009 (3) | 0.001 (3) | −0.020 (3) |
C14 | 0.054 (3) | 0.124 (5) | 0.090 (4) | 0.002 (3) | −0.005 (3) | 0.007 (4) |
C15 | 0.065 (4) | 0.101 (4) | 0.164 (6) | 0.001 (3) | −0.015 (4) | 0.047 (4) |
C16 | 0.061 (3) | 0.064 (3) | 0.132 (5) | −0.009 (2) | −0.011 (3) | 0.023 (3) |
C17 | 0.109 (4) | 0.039 (2) | 0.159 (5) | −0.004 (3) | 0.012 (4) | 0.008 (3) |
C18 | 0.062 (3) | 0.037 (2) | 0.073 (3) | 0.0033 (19) | 0.028 (2) | 0.003 (2) |
C19 | 0.053 (3) | 0.041 (2) | 0.059 (3) | 0.0070 (19) | 0.0181 (19) | 0.0060 (18) |
C20 | 0.046 (2) | 0.0422 (19) | 0.043 (2) | 0.0095 (17) | 0.0155 (17) | 0.0056 (17) |
C21 | 0.052 (2) | 0.048 (2) | 0.047 (2) | 0.0061 (19) | 0.0104 (19) | 0.0079 (18) |
C22 | 0.055 (3) | 0.071 (3) | 0.054 (3) | 0.009 (2) | 0.007 (2) | 0.008 (2) |
C23 | 0.064 (3) | 0.074 (3) | 0.087 (4) | 0.024 (3) | 0.000 (3) | 0.029 (3) |
C24 | 0.075 (3) | 0.047 (2) | 0.095 (4) | 0.015 (2) | 0.020 (3) | 0.023 (2) |
C25 | 0.070 (4) | 0.112 (4) | 0.084 (4) | −0.018 (3) | −0.001 (3) | −0.009 (3) |
C26 | 0.067 (3) | 0.077 (3) | 0.091 (4) | −0.005 (3) | 0.007 (3) | −0.029 (3) |
C27 | 0.054 (3) | 0.045 (2) | 0.055 (3) | −0.0123 (19) | −0.002 (2) | −0.0082 (19) |
C28 | 0.098 (4) | 0.057 (3) | 0.070 (3) | −0.017 (3) | −0.005 (3) | 0.003 (2) |
C29 | 0.126 (6) | 0.063 (3) | 0.115 (6) | 0.023 (4) | −0.050 (4) | −0.021 (4) |
C30 | 0.070 (4) | 0.140 (7) | 0.138 (7) | 0.022 (4) | −0.027 (4) | −0.082 (6) |
C31 | 0.060 (4) | 0.147 (6) | 0.093 (4) | −0.035 (4) | 0.024 (3) | −0.042 (4) |
C32 | 0.078 (4) | 0.064 (3) | 0.066 (3) | −0.023 (3) | 0.000 (3) | 0.003 (2) |
Geometric parameters (Å, º) top
Zn1—O1 | 1.964 (2) | C12—H12 | 0.9300 |
Zn1—O3 | 1.987 (2) | C13—C14 | 1.352 (7) |
Zn1—Cl1 | 2.2303 (12) | C13—H13 | 0.9300 |
Zn1—Cl2 | 2.2178 (11) | C14—C15 | 1.362 (7) |
N1—C2 | 1.308 (5) | C14—H14 | 0.9300 |
N1—C10 | 1.453 (5) | C15—C16 | 1.379 (6) |
N1—H1 | 0.9693 | C15—H15 | 0.9300 |
N2—C18 | 1.292 (5) | C16—H16 | 0.9300 |
N2—C26 | 1.470 (5) | C17—C18 | 1.514 (5) |
N2—H2 | 0.9717 | C17—H17A | 0.9600 |
O1—C4 | 1.312 (4) | C17—H17B | 0.9600 |
O2—C6 | 1.361 (5) | C17—H17C | 0.9600 |
O2—C9 | 1.438 (5) | C18—C19 | 1.433 (5) |
O3—C20 | 1.312 (4) | C19—C24 | 1.412 (5) |
O4—C22 | 1.361 (5) | C19—C20 | 1.428 (5) |
O4—C25 | 1.411 (5) | C20—C21 | 1.400 (5) |
C1—C2 | 1.498 (5) | C21—C22 | 1.361 (5) |
C1—H1A | 0.9600 | C21—H21 | 0.9300 |
C1—H1B | 0.9600 | C22—C23 | 1.383 (6) |
C1—H1C | 0.9600 | C23—C24 | 1.348 (6) |
C2—C3 | 1.440 (5) | C23—H23 | 0.9300 |
C3—C8 | 1.418 (5) | C24—H24 | 0.9300 |
C3—C4 | 1.421 (5) | C25—H25A | 0.9600 |
C4—C5 | 1.398 (5) | C25—H25B | 0.9600 |
C5—C6 | 1.360 (5) | C25—H25C | 0.9600 |
C5—H5 | 0.9300 | C26—C27 | 1.501 (6) |
C6—C7 | 1.406 (5) | C26—H26A | 0.9700 |
C7—C8 | 1.344 (5) | C26—H26B | 0.9700 |
C7—H7 | 0.9300 | C27—C28 | 1.361 (6) |
C8—H8 | 0.9300 | C27—C32 | 1.365 (6) |
C9—H9A | 0.9600 | C28—C29 | 1.376 (8) |
C9—H9B | 0.9600 | C28—H28 | 0.9300 |
C9—H9C | 0.9600 | C29—C30 | 1.353 (9) |
C10—C11 | 1.506 (5) | C29—H29 | 0.9300 |
C10—H10A | 0.9700 | C30—C31 | 1.354 (9) |
C10—H10B | 0.9700 | C30—H30 | 0.9300 |
C11—C16 | 1.366 (5) | C31—C32 | 1.361 (7) |
C11—C12 | 1.376 (5) | C31—H31 | 0.9300 |
C12—C13 | 1.375 (6) | C32—H32 | 0.9300 |
| | | |
O1—Zn1—O3 | 108.13 (10) | C13—C14—H14 | 120.5 |
O1—Zn1—Cl2 | 113.27 (8) | C15—C14—H14 | 120.5 |
O3—Zn1—Cl2 | 102.41 (7) | C14—C15—C16 | 120.5 (5) |
O1—Zn1—Cl1 | 102.80 (8) | C14—C15—H15 | 119.8 |
O3—Zn1—Cl1 | 110.58 (8) | C16—C15—H15 | 119.8 |
Cl1—Zn1—Cl2 | 119.42 (5) | C11—C16—C15 | 120.8 (4) |
C2—N1—C10 | 127.3 (3) | C11—C16—H16 | 119.6 |
C2—N1—H1 | 104.2 | C15—C16—H16 | 119.6 |
C10—N1—H1 | 128.2 | C18—C17—H17A | 109.5 |
C18—N2—C26 | 129.1 (4) | C18—C17—H17B | 109.5 |
C18—N2—H2 | 119.2 | H17A—C17—H17B | 109.5 |
C26—N2—H2 | 111.5 | C18—C17—H17C | 109.5 |
C4—O1—Zn1 | 127.9 (2) | H17A—C17—H17C | 109.5 |
C6—O2—C9 | 117.3 (4) | H17B—C17—H17C | 109.5 |
C20—O3—Zn1 | 126.8 (2) | N2—C18—C19 | 119.7 (3) |
C22—O4—C25 | 118.5 (3) | N2—C18—C17 | 119.1 (4) |
C2—C1—H1A | 109.5 | C19—C18—C17 | 121.2 (4) |
C2—C1—H1B | 109.5 | C24—C19—C20 | 116.8 (4) |
H1A—C1—H1B | 109.5 | C24—C19—C18 | 121.2 (4) |
C2—C1—H1C | 109.5 | C20—C19—C18 | 122.0 (3) |
H1A—C1—H1C | 109.5 | O3—C20—C21 | 120.9 (3) |
H1B—C1—H1C | 109.5 | O3—C20—C19 | 120.1 (3) |
N1—C2—C3 | 119.4 (3) | C21—C20—C19 | 119.0 (3) |
N1—C2—C1 | 118.7 (4) | C22—C21—C20 | 121.1 (4) |
C3—C2—C1 | 121.9 (4) | C22—C21—H21 | 119.4 |
C8—C3—C4 | 117.3 (4) | C20—C21—H21 | 119.4 |
C8—C3—C2 | 120.9 (3) | C21—C22—O4 | 124.4 (4) |
C4—C3—C2 | 121.8 (3) | C21—C22—C23 | 120.6 (4) |
O1—C4—C5 | 120.4 (3) | O4—C22—C23 | 115.0 (4) |
O1—C4—C3 | 120.6 (3) | C24—C23—C22 | 119.7 (4) |
C5—C4—C3 | 118.9 (4) | C24—C23—H23 | 120.2 |
C6—C5—C4 | 121.4 (4) | C22—C23—H23 | 120.2 |
C6—C5—H5 | 119.3 | C23—C24—C19 | 122.8 (4) |
C4—C5—H5 | 119.3 | C23—C24—H24 | 118.6 |
C5—C6—O2 | 124.5 (4) | C19—C24—H24 | 118.6 |
C5—C6—C7 | 120.5 (4) | O4—C25—H25A | 109.5 |
O2—C6—C7 | 114.9 (4) | O4—C25—H25B | 109.5 |
C8—C7—C6 | 119.0 (4) | H25A—C25—H25B | 109.5 |
C8—C7—H7 | 120.5 | O4—C25—H25C | 109.5 |
C6—C7—H7 | 120.5 | H25A—C25—H25C | 109.5 |
C7—C8—C3 | 122.8 (4) | H25B—C25—H25C | 109.5 |
C7—C8—H8 | 118.6 | N2—C26—C27 | 110.6 (3) |
C3—C8—H8 | 118.6 | N2—C26—H26A | 109.5 |
O2—C9—H9A | 109.5 | C27—C26—H26A | 109.5 |
O2—C9—H9B | 109.5 | N2—C26—H26B | 109.5 |
H9A—C9—H9B | 109.5 | C27—C26—H26B | 109.5 |
O2—C9—H9C | 109.5 | H26A—C26—H26B | 108.1 |
H9A—C9—H9C | 109.5 | C28—C27—C32 | 118.8 (4) |
H9B—C9—H9C | 109.5 | C28—C27—C26 | 120.8 (4) |
N1—C10—C11 | 113.7 (3) | C32—C27—C26 | 120.5 (4) |
N1—C10—H10A | 108.8 | C27—C28—C29 | 120.7 (5) |
C11—C10—H10A | 108.8 | C27—C28—H28 | 119.6 |
N1—C10—H10B | 108.8 | C29—C28—H28 | 119.6 |
C11—C10—H10B | 108.8 | C30—C29—C28 | 119.4 (6) |
H10A—C10—H10B | 107.7 | C30—C29—H29 | 120.3 |
C16—C11—C12 | 118.3 (4) | C28—C29—H29 | 120.3 |
C16—C11—C10 | 122.3 (4) | C29—C30—C31 | 120.3 (7) |
C12—C11—C10 | 119.4 (4) | C29—C30—H30 | 119.9 |
C13—C12—C11 | 120.2 (4) | C31—C30—H30 | 119.9 |
C13—C12—H12 | 119.9 | C30—C31—C32 | 120.2 (6) |
C11—C12—H12 | 119.9 | C30—C31—H31 | 119.9 |
C14—C13—C12 | 121.3 (5) | C32—C31—H31 | 119.9 |
C14—C13—H13 | 119.4 | C31—C32—C27 | 120.6 (5) |
C12—C13—H13 | 119.4 | C31—C32—H32 | 119.7 |
C13—C14—C15 | 118.9 (5) | C27—C32—H32 | 119.7 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.97 | 1.63 | 2.543 (4) | 156 |
N2—H2···O3 | 0.97 | 1.77 | 2.545 (4) | 134 |