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metal-organic compounds
The Zr atom in the title disolvate, [ZrCl4(C23H25NO)2]·2CH2Cl2, lies on a special position of site symmetry in a trans-Cl4O2Zr octahedral geometry.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680603131X/bt2160sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680603131X/bt2160Isup2.hkl |
CCDC reference: 620688
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.006 Å
- Disorder in solvent or counterion
- R factor = 0.052
- wR factor = 0.161
- Data-to-parameter ratio = 18.9
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for C18
Author Response: The atom is the pivot atom of an isopropyl group; there is some disorder in the group but it is not necessary to treat the disorder. |
Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.83 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.48 Ratio PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for Zr1
Author Response: The atom is the pivot atom of an isopropyl group; there is some disorder in the group but it is not necessary to treat the disorder. |
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C21
Author Response: The atom is the pivot atom of an isopropyl group; there is some disorder in the group but it is not necessary to treat the disorder. |
PLAT431_ALERT_2_B Short Inter HL..A Contact Cl4 .. Cl4 .. 3.07 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C24 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C24' PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc. PLAT410_ALERT_2_C Short Intra H...H Contact H8 .. H11 .. 1.98 Ang.
1 ALERT level A = In general: serious problem 5 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Computing details top
Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.
trans-Tetrachlorobis{1-[(2,6-diisopropylphenyl)iminiomethyl]-2-naphtholato- κO}zirconium(IV) dichloromethane disolvate top
Crystal data top
[ZrCl4(C23H25NO)2]·2CH2Cl2 | F(000) = 2192 |
Mr = 1065.75 | Dx = 1.363 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 5121 reflections |
a = 17.700 (1) Å | θ = 2.3–25.6° |
b = 16.897 (1) Å | µ = 0.66 mm−1 |
c = 18.190 (1) Å | T = 295 K |
β = 107.286 (1)° | Block, yellow |
V = 5194.6 (5) Å3 | 0.25 × 0.20 × 0.16 mm |
Z = 4 |
Data collection top
Bruker APEXII area-detector diffractometer | 5829 independent reflections |
Radiation source: fine-focus sealed tube | 4410 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
φ and ω scans | θmax = 27.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −22→22 |
Tmin = 0.852, Tmax = 0.902 | k = −10→21 |
15120 measured reflections | l = −22→23 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.161 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0967P)2 + 2.9123P] where P = (Fo2 + 2Fc2)/3 |
5829 reflections | (Δ/σ)max = 0.001 |
309 parameters | Δρmax = 0.53 e Å−3 |
43 restraints | Δρmin = −0.36 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Zr1 | 0.2500 | 0.2500 | 0.5000 | 0.0560 (2) | |
Cl1 | 0.17909 (8) | 0.34234 (7) | 0.55970 (7) | 0.1043 (4) | |
Cl2 | 0.36778 (6) | 0.33501 (7) | 0.54233 (6) | 0.1013 (4) | |
Cl3 | 0.2228 (3) | 0.6999 (3) | 0.3078 (3) | 0.157 (1) | 0.73 (1) |
Cl4 | 0.0685 (3) | 0.7432 (5) | 0.2146 (4) | 0.295 (4) | 0.73 (1) |
Cl3' | 0.1842 (9) | 0.6919 (5) | 0.3192 (5) | 0.141 (3) | 0.27 (1) |
Cl4' | 0.1058 (9) | 0.8132 (7) | 0.2206 (8) | 0.242 (7) | 0.27 (1) |
O1 | 0.2166 (1) | 0.3172 (1) | 0.4012 (1) | 0.0605 (5) | |
N1 | 0.2629 (1) | 0.4701 (1) | 0.4078 (1) | 0.0516 (5) | |
C1 | 0.1683 (2) | 0.3320 (2) | 0.3328 (2) | 0.050 (1) | |
C2 | 0.1268 (2) | 0.2694 (2) | 0.2869 (2) | 0.065 (1) | |
C3 | 0.0760 (2) | 0.2839 (2) | 0.2170 (2) | 0.067 (1) | |
C4 | 0.0598 (2) | 0.3611 (2) | 0.1868 (2) | 0.057 (1) | |
C5 | 0.0023 (2) | 0.3748 (2) | 0.1147 (2) | 0.071 (1) | |
C6 | −0.0138 (2) | 0.4492 (3) | 0.0873 (2) | 0.083 (1) | |
C7 | 0.0264 (2) | 0.5126 (3) | 0.1297 (2) | 0.089 (1) | |
C8 | 0.0821 (2) | 0.5020 (2) | 0.1997 (2) | 0.075 (1) | |
C9 | 0.1006 (2) | 0.4256 (2) | 0.2301 (2) | 0.053 (1) | |
C10 | 0.1591 (2) | 0.4098 (2) | 0.3038 (1) | 0.047 (1) | |
C11 | 0.2072 (2) | 0.4718 (2) | 0.3433 (2) | 0.051 (1) | |
C12 | 0.3124 (2) | 0.5380 (2) | 0.4385 (2) | 0.052 (1) | |
C13 | 0.3744 (2) | 0.5560 (2) | 0.4085 (2) | 0.060 (1) | |
C14 | 0.4187 (2) | 0.6229 (2) | 0.4376 (2) | 0.071 (1) | |
C15 | 0.4022 (2) | 0.6685 (2) | 0.4930 (2) | 0.079 (1) | |
C16 | 0.3420 (2) | 0.6491 (2) | 0.5215 (2) | 0.078 (1) | |
C17 | 0.2949 (2) | 0.5824 (2) | 0.4951 (2) | 0.063 (1) | |
C18 | 0.3943 (2) | 0.5054 (2) | 0.3486 (2) | 0.075 (1) | |
C19 | 0.3932 (5) | 0.5521 (4) | 0.2778 (3) | 0.159 (3) | |
C20 | 0.4747 (4) | 0.4682 (5) | 0.3799 (4) | 0.179 (4) | |
C21 | 0.2276 (3) | 0.5623 (2) | 0.5271 (3) | 0.086 (1) | |
C22 | 0.2556 (5) | 0.5527 (5) | 0.6126 (4) | 0.176 (3) | |
C23 | 0.1610 (3) | 0.6208 (4) | 0.5000 (5) | 0.143 (2) | |
C24 | 0.1698 (6) | 0.7627 (8) | 0.2337 (6) | 0.168 (5) | 0.73 (1) |
C24' | 0.169 (2) | 0.732 (1) | 0.2259 (9) | 0.113 (8) | 0.27 (1) |
H1 | 0.275 (2) | 0.427 (1) | 0.432 (2) | 0.06 (1)* | |
H2 | 0.1346 | 0.2177 | 0.3052 | 0.078* | |
H3 | 0.0505 | 0.2415 | 0.1874 | 0.080* | |
H5 | −0.0244 | 0.3323 | 0.0862 | 0.085* | |
H6 | −0.0517 | 0.4579 | 0.0402 | 0.099* | |
H7 | 0.0153 | 0.5635 | 0.1101 | 0.106* | |
H8 | 0.1078 | 0.5457 | 0.2271 | 0.090* | |
H11 | 0.1975 | 0.5210 | 0.3196 | 0.061* | |
H14 | 0.4604 | 0.6370 | 0.4190 | 0.085* | |
H15 | 0.4325 | 0.7133 | 0.5113 | 0.094* | |
H16 | 0.3318 | 0.6807 | 0.5593 | 0.093* | |
H18 | 0.3549 | 0.4630 | 0.3335 | 0.090* | |
H19a | 0.3419 | 0.5757 | 0.2566 | 0.238* | |
H19b | 0.4042 | 0.5176 | 0.2404 | 0.238* | |
H19c | 0.4326 | 0.5929 | 0.2914 | 0.238* | |
H20a | 0.4860 | 0.4366 | 0.3406 | 0.269* | |
H20b | 0.4754 | 0.4353 | 0.4232 | 0.269* | |
H20c | 0.5139 | 0.5090 | 0.3960 | 0.269* | |
H21 | 0.2069 | 0.5108 | 0.5056 | 0.103* | |
H22a | 0.2115 | 0.5399 | 0.6309 | 0.264* | |
H22b | 0.2793 | 0.6012 | 0.6359 | 0.264* | |
H22c | 0.2940 | 0.5109 | 0.6259 | 0.264* | |
H23a | 0.1190 | 0.6068 | 0.5209 | 0.215* | |
H23b | 0.1418 | 0.6199 | 0.4448 | 0.215* | |
H23c | 0.1799 | 0.6729 | 0.5171 | 0.215* | |
H24a | 0.1807 | 0.8175 | 0.2490 | 0.201* | 0.73 (1) |
H24b | 0.1857 | 0.7535 | 0.1877 | 0.201* | 0.73 (1) |
H24c | 0.2191 | 0.7483 | 0.2189 | 0.135* | 0.27 (1) |
H24d | 0.1450 | 0.6926 | 0.1869 | 0.135* | 0.27 (1) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Zr1 | 0.0492 (2) | 0.0424 (2) | 0.0687 (3) | −0.0059 (2) | 0.0054 (2) | 0.0147 (2) |
Cl1 | 0.1287 (9) | 0.0858 (7) | 0.1056 (8) | 0.0366 (6) | 0.0458 (7) | 0.0212 (6) |
Cl2 | 0.0748 (6) | 0.0985 (7) | 0.1088 (8) | −0.0415 (5) | −0.0063 (5) | 0.0293 (6) |
Cl3 | 0.186 (3) | 0.129 (2) | 0.162 (3) | 0.001 (2) | 0.063 (2) | 0.029 (2) |
Cl4 | 0.222 (5) | 0.285 (7) | 0.393 (7) | 0.062 (4) | 0.115 (5) | 0.091 (5) |
Cl3' | 0.225 (9) | 0.082 (3) | 0.116 (4) | 0.007 (5) | 0.050 (5) | −0.012 (3) |
Cl4' | 0.26 (1) | 0.137 (7) | 0.29 (1) | 0.043 (7) | 0.017 (7) | 0.053 (6) |
O1 | 0.061 (1) | 0.046 (1) | 0.066 (1) | −0.006 (1) | 0.004 (1) | 0.012 (1) |
N1 | 0.057 (1) | 0.038 (1) | 0.057 (1) | −0.006 (1) | 0.012 (1) | 0.006 (1) |
C1 | 0.051 (1) | 0.044 (1) | 0.055 (1) | 0.000 (1) | 0.017 (1) | 0.001 (1) |
C2 | 0.073 (2) | 0.046 (1) | 0.071 (2) | −0.001 (1) | 0.015 (2) | −0.004 (1) |
C3 | 0.071 (2) | 0.059 (2) | 0.067 (2) | −0.008 (2) | 0.017 (2) | −0.016 (2) |
C4 | 0.053 (2) | 0.072 (2) | 0.048 (1) | −0.005 (1) | 0.018 (1) | −0.003 (1) |
C5 | 0.062 (2) | 0.098 (3) | 0.052 (2) | −0.014 (2) | 0.016 (1) | −0.003 (2) |
C6 | 0.068 (2) | 0.114 (3) | 0.057 (2) | −0.009 (2) | 0.004 (2) | 0.020 (2) |
C7 | 0.084 (2) | 0.085 (3) | 0.081 (2) | −0.003 (2) | 0.001 (2) | 0.032 (2) |
C8 | 0.074 (2) | 0.068 (2) | 0.070 (2) | −0.008 (2) | 0.000 (2) | 0.016 (2) |
C9 | 0.051 (1) | 0.057 (2) | 0.051 (1) | −0.003 (1) | 0.016 (1) | 0.005 (1) |
C10 | 0.048 (1) | 0.043 (1) | 0.051 (1) | 0.000 (1) | 0.017 (1) | 0.002 (1) |
C11 | 0.052 (1) | 0.044 (1) | 0.057 (2) | 0.000 (1) | 0.018 (1) | 0.008 (1) |
C12 | 0.053 (2) | 0.040 (1) | 0.060 (2) | −0.006 (1) | 0.010 (1) | 0.006 (1) |
C13 | 0.059 (2) | 0.049 (2) | 0.069 (2) | −0.004 (1) | 0.016 (1) | 0.007 (1) |
C14 | 0.062 (2) | 0.058 (2) | 0.090 (2) | −0.016 (2) | 0.018 (2) | 0.007 (2) |
C15 | 0.077 (2) | 0.052 (2) | 0.097 (3) | −0.017 (2) | 0.012 (2) | −0.008 (2) |
C16 | 0.092 (2) | 0.057 (2) | 0.083 (2) | −0.011 (2) | 0.024 (2) | −0.015 (2) |
C17 | 0.069 (2) | 0.051 (2) | 0.071 (2) | −0.006 (1) | 0.021 (2) | −0.003 (1) |
C18 | 0.075 (2) | 0.062 (2) | 0.097 (3) | −0.014 (2) | 0.041 (2) | −0.006 (2) |
C19 | 0.276 (9) | 0.126 (5) | 0.094 (4) | 0.052 (5) | 0.084 (5) | 0.018 (3) |
C20 | 0.180 (7) | 0.228 (8) | 0.115 (4) | 0.126 (6) | 0.022 (4) | −0.015 (5) |
C21 | 0.108 (3) | 0.065 (2) | 0.102 (3) | −0.018 (2) | 0.058 (3) | −0.017 (2) |
C22 | 0.208 (8) | 0.236 (9) | 0.105 (4) | −0.073 (7) | 0.078 (5) | −0.007 (5) |
C23 | 0.105 (4) | 0.119 (4) | 0.233 (7) | 0.010 (3) | 0.092 (4) | 0.011 (5) |
C24 | 0.175 (8) | 0.20 (1) | 0.162 (8) | 0.006 (8) | 0.103 (7) | −0.022 (7) |
C24' | 0.13 (1) | 0.09 (1) | 0.12 (1) | 0.014 (8) | 0.035 (8) | −0.003 (8) |
Geometric parameters (Å, º) top
Zr1—O1 | 2.058 (2) | C21—C22 | 1.494 (7) |
Zr1—Cl2 | 2.459 (1) | C21—C23 | 1.503 (7) |
Zr1—Cl1 | 2.449 (1) | N1—H1 | 0.84 (1) |
Cl3—C24 | 1.752 (9) | C2—H2 | 0.93 |
Cl4—C24 | 1.753 (9) | C3—H3 | 0.93 |
Cl3'—C24' | 1.77 (1) | C5—H5 | 0.93 |
Cl4'—C24' | 1.76 (1) | C6—H6 | 0.93 |
O1—C1 | 1.308 (3) | C7—H7 | 0.93 |
N1—C11 | 1.289 (4) | C8—H8 | 0.93 |
N1—C12 | 1.451 (3) | C11—H11 | 0.93 |
C1—C2 | 1.410 (4) | C14—H14 | 0.93 |
C1—C10 | 1.409 (4) | C15—H15 | 0.93 |
C2—C3 | 1.344 (5) | C16—H16 | 0.93 |
C3—C4 | 1.411 (5) | C18—H18 | 0.98 |
C4—C9 | 1.411 (4) | C19—H19a | 0.96 |
C4—C5 | 1.419 (4) | C19—H19b | 0.96 |
C5—C6 | 1.351 (5) | C19—H19c | 0.96 |
C6—C7 | 1.386 (6) | C20—H20a | 0.96 |
C7—C8 | 1.371 (5) | C20—H20b | 0.96 |
C8—C9 | 1.405 (4) | C20—H20c | 0.96 |
C9—C10 | 1.454 (4) | C21—H21 | 0.98 |
C10—C11 | 1.405 (4) | C22—H22a | 0.96 |
C12—C17 | 1.381 (4) | C22—H22b | 0.96 |
C12—C13 | 1.396 (4) | C22—H22c | 0.96 |
C13—C14 | 1.387 (4) | C23—H23a | 0.96 |
C13—C18 | 1.508 (5) | C23—H23b | 0.96 |
C14—C15 | 1.368 (5) | C23—H23c | 0.96 |
C15—C16 | 1.357 (5) | C24—H24a | 0.97 |
C16—C17 | 1.398 (5) | C24—H24b | 0.97 |
C17—C21 | 1.512 (5) | C24'—H24c | 0.97 |
C18—C20 | 1.504 (7) | C24'—H24d | 0.97 |
C18—C19 | 1.505 (6) | ||
O1—Zr1—O1i | 180 | C6—C5—H5 | 119.7 |
O1—Zr1—Cl1 | 89.09 (7) | C4—C5—H5 | 119.7 |
O1—Zr1—Cl1i | 90.91 (7) | C5—C6—H6 | 120.1 |
O1—Zr1—Cl2 | 87.02 (6) | C7—C6—H6 | 120.1 |
O1—Zr1—Cl2i | 92.98 (6) | C8—C7—H7 | 119.2 |
Cl1—Zr1—Cl1i | 180 | C6—C7—H7 | 119.2 |
Cl1—Zr1—Cl2 | 89.28 (5) | C7—C8—H8 | 119.9 |
Cl1—Zr1—Cl2i | 90.72 (5) | C9—C8—H8 | 119.9 |
Cl2—Zr1—Cl2i | 180 | N1—C11—H11 | 115.4 |
C1—O1—Zr1 | 150.8 (2) | C10—C11—H11 | 115.4 |
C11—N1—C12 | 123.0 (2) | C15—C14—H14 | 119.3 |
O1—C1—C2 | 119.9 (2) | C13—C14—H14 | 119.3 |
O1—C1—C10 | 120.3 (2) | C16—C15—H15 | 119.7 |
C2—C1—C10 | 119.8 (3) | C14—C15—H15 | 119.7 |
C3—C2—C1 | 120.5 (3) | C15—C16—H16 | 119.4 |
C2—C3—C4 | 122.6 (3) | C17—C16—H16 | 119.4 |
C3—C4—C9 | 119.0 (3) | C20—C18—H18 | 108.4 |
C3—C4—C5 | 121.2 (3) | C13—C18—H18 | 108.4 |
C9—C4—C5 | 119.8 (3) | C19—C18—H18 | 108.4 |
C6—C5—C4 | 120.6 (3) | C18—C19—H19a | 109.5 |
C5—C6—C7 | 119.7 (3) | C18—C19—H19b | 109.5 |
C8—C7—C6 | 121.7 (4) | H19a—C19—H19b | 109.5 |
C7—C8—C9 | 120.3 (4) | C18—C19—H19c | 109.5 |
C8—C9—C4 | 118.0 (3) | H19a—C19—H19c | 109.5 |
C8—C9—C10 | 123.4 (3) | H19b—C19—H19c | 109.5 |
C4—C9—C10 | 118.7 (3) | C18—C20—H20a | 109.5 |
C11—C10—C1 | 121.3 (2) | C18—C20—H20b | 109.5 |
C11—C10—C9 | 119.5 (2) | H20a—C20—H20b | 109.5 |
C1—C10—C9 | 119.2 (2) | C18—C20—H20c | 109.5 |
N1—C11—C10 | 129.3 (2) | H20a—C20—H20c | 109.5 |
C17—C12—C13 | 123.4 (3) | H20b—C20—H20c | 109.5 |
C17—C12—N1 | 118.2 (3) | C22—C21—H21 | 106.8 |
C13—C12—N1 | 118.4 (3) | C23—C21—H21 | 106.8 |
C14—C13—C12 | 116.7 (3) | C17—C21—H21 | 106.8 |
C14—C13—C18 | 120.7 (3) | C21—C22—H22a | 109.5 |
C12—C13—C18 | 122.6 (3) | C21—C22—H22b | 109.5 |
C15—C14—C13 | 121.3 (3) | H22a—C22—H22b | 109.5 |
C16—C15—C14 | 120.6 (3) | C21—C22—H22c | 109.5 |
C15—C16—C17 | 121.3 (3) | H22a—C22—H22c | 109.5 |
C12—C17—C16 | 116.8 (3) | H22b—C22—H22c | 109.5 |
C12—C17—C21 | 122.8 (3) | C21—C23—H23a | 109.5 |
C16—C17—C21 | 120.4 (3) | C21—C23—H23b | 109.5 |
C20—C18—C13 | 111.2 (4) | H23a—C23—H23b | 109.5 |
C20—C18—C19 | 108.3 (5) | C21—C23—H23c | 109.5 |
C13—C18—C19 | 111.9 (3) | H23a—C23—H23c | 109.5 |
C22—C21—C23 | 113.4 (5) | H23b—C23—H23c | 109.5 |
C22—C21—C17 | 111.7 (4) | Cl4—C24—H24a | 109.9 |
C23—C21—C17 | 110.9 (4) | Cl3—C24—H24a | 109.9 |
Cl4—C24—Cl3 | 108.7 (6) | Cl4—C24—H24b | 109.9 |
Cl4'—C24'—Cl3' | 105.1 (8) | Cl3—C24—H24b | 109.9 |
C11—N1—H1 | 120 (2) | H24a—C24—H24b | 108.3 |
C12—N1—H1 | 116 (2) | Cl4'—C24'—H24c | 110.7 |
C3—C2—H2 | 119.8 | Cl3'—C24'—H24c | 110.7 |
C1—C2—H2 | 119.8 | Cl4'—C24'—H24d | 110.7 |
C2—C3—H3 | 118.7 | Cl3'—C24'—H24d | 110.7 |
C4—C3—H3 | 118.7 | H24c—C24'—H24d | 108.8 |
Cl1i—Zr1—O1—C1 | 85.6 (4) | C4—C9—C10—C1 | −5.5 (4) |
Cl1—Zr1—O1—C1 | −94.4 (4) | C12—N1—C11—C10 | 174.5 (3) |
Cl2—Zr1—O1—C1 | 176.3 (4) | C1—C10—C11—N1 | −0.9 (4) |
Cl2i—Zr1—O1—C1 | −3.7 (4) | C9—C10—C11—N1 | −178.5 (3) |
Zr1—O1—C1—C2 | −29.6 (5) | C11—N1—C12—C17 | 100.0 (3) |
Zr1—O1—C1—C10 | 152.2 (3) | C11—N1—C12—C13 | −78.9 (4) |
O1—C1—C2—C3 | 179.0 (3) | C17—C12—C13—C14 | −0.9 (5) |
C10—C1—C2—C3 | −2.8 (5) | N1—C12—C13—C14 | 177.9 (3) |
C1—C2—C3—C4 | −1.7 (5) | C17—C12—C13—C18 | 178.0 (3) |
C2—C3—C4—C9 | 2.5 (5) | N1—C12—C13—C18 | −3.2 (4) |
C2—C3—C4—C5 | −176.2 (3) | C12—C13—C14—C15 | 0.2 (5) |
C3—C4—C5—C6 | 178.5 (3) | C18—C13—C14—C15 | −178.8 (3) |
C9—C4—C5—C6 | −0.2 (5) | C13—C14—C15—C16 | 0.4 (6) |
C4—C5—C6—C7 | 0.3 (6) | C14—C15—C16—C17 | −0.3 (6) |
C5—C6—C7—C8 | −0.6 (6) | C13—C12—C17—C16 | 1.1 (5) |
C6—C7—C8—C9 | 0.7 (6) | N1—C12—C17—C16 | −177.8 (3) |
C7—C8—C9—C4 | −0.5 (5) | C13—C12—C17—C21 | −180.0 (3) |
C7—C8—C9—C10 | 179.9 (3) | N1—C12—C17—C21 | 1.2 (5) |
C3—C4—C9—C8 | −178.4 (3) | C15—C16—C17—C12 | −0.4 (5) |
C5—C4—C9—C8 | 0.3 (4) | C15—C16—C17—C21 | −179.4 (4) |
C3—C4—C9—C10 | 1.1 (4) | C14—C13—C18—C20 | 63.9 (5) |
C5—C4—C9—C10 | 179.8 (3) | C12—C13—C18—C20 | −115.0 (5) |
O1—C1—C10—C11 | 6.9 (4) | C14—C13—C18—C19 | −57.3 (5) |
C2—C1—C10—C11 | −171.3 (3) | C12—C13—C18—C19 | 123.8 (5) |
O1—C1—C10—C9 | −175.5 (2) | C12—C17—C21—C22 | 124.1 (5) |
C2—C1—C10—C9 | 6.3 (4) | C16—C17—C21—C22 | −57.0 (6) |
C8—C9—C10—C11 | −8.3 (4) | C12—C17—C21—C23 | −108.3 (5) |
C4—C9—C10—C11 | 172.2 (2) | C16—C17—C21—C23 | 70.6 (6) |
C8—C9—C10—C1 | 174.1 (3) |
Symmetry code: (i) −x+1/2, −y+1/2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.84 (1) | 2.12 (3) | 2.703 (3) | 126 (3) |
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