organic compounds
The title compound, C18H15Cl4N2O+·NO3-, (+)-miconazole nitrate, is a component of racemic miconazole nitrate, a broad spectrum antimycotic agent with antibacterial activity. It crystallizes with two protonated molecules in the asymmetric unit, both with S configuration, which are linked into a dimer by hydrogen bonds with the nitrate anions.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804003058/na6291sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804003058/na6291Isup2.hkl |
CCDC reference: 236075
Computing details top
Data collection: DIF4 (Stoe & Cie, 1992); cell refinement: DIF4; data reduction: REDU4 (Stoe & Cie, 1992); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Bergerhoff, 1996); software used to prepare material for publication: PARST (Nardelli, 1983).
(+)-1-[(2S)-2-(2,4-Dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-
1H-imidazole mononitrate top
Crystal data top
C18H15Cl4N2O+·NO3− | F(000) = 976 |
Mr = 479.13 | Dx = 1.528 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 13.23 (1) Å | Cell parameters from 24 reflections |
b = 9.191 (7) Å | θ = 7.7–10.3° |
c = 18.30 (2) Å | µ = 0.60 mm−1 |
β = 110.63 (8)° | T = 293 K |
V = 2082 (3) Å3 | Prism, colourless |
Z = 4 | 0.60 × 0.50 × 0.40 mm |
Data collection top
Stoe STADI4 four-circle diffractometer | Rint = 0.020 |
ω scans | θmax = 25.0° |
Absorption correction: ψ scan (EMPIR; Stoe & Cie, 1992) | h = −15→15 |
Tmin = 0.721, Tmax = 0.787 | k = −10→10 |
9914 measured reflections | l = −21→21 |
7254 independent reflections | 3 standard reflections every 60 min |
5518 reflections with F2 > 2σ(F2) | intensity decay: none |
Refinement top
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (.0448P)2 + .4257P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.042 | (Δ/σ)max = 0.001 |
wR(F2) = 0.101 | Δρmax = 0.25 e Å−3 |
S = 1.03 | Δρmin = −0.32 e Å−3 |
7254 reflections | Absolute structure: Flack (1983); 3357 Friedel pairs |
523 parameters | Absolute structure parameter: −0.02 (5) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
N1 | 0.0295 (2) | 0.3243 (4) | 0.3961 (2) | 0.048 (1)* | |
C2 | −0.0608 (3) | 0.3190 (5) | 0.3334 (2) | 0.058 (2)* | |
N3 | −0.0817 (3) | 0.1829 (4) | 0.3128 (2) | 0.065 (1)* | |
C4 | −0.0044 (3) | 0.0958 (5) | 0.3627 (2) | 0.068 (2)* | |
C5 | 0.0654 (3) | 0.1848 (5) | 0.4144 (2) | 0.056 (2)* | |
C6 | 0.0794 (3) | 0.4559 (4) | 0.4394 (2) | 0.052 (1)* | |
C7 | 0.1345 (3) | 0.5490 (4) | 0.3954 (2) | 0.048 (1)* | |
C8 | 0.1992 (3) | 0.6691 (4) | 0.4470 (2) | 0.046 (1)* | |
C9 | 0.3084 (3) | 0.6952 (4) | 0.4598 (2) | 0.045 (1)* | |
C10 | 0.3684 (3) | 0.7991 (4) | 0.5123 (2) | 0.050 (2)* | |
C11 | 0.3193 (3) | 0.8796 (4) | 0.5536 (2) | 0.051 (1)* | |
C12 | 0.2106 (3) | 0.8640 (4) | 0.5396 (3) | 0.058 (2)* | |
C13 | 0.1522 (3) | 0.7599 (4) | 0.4873 (2) | 0.056 (2)* | |
Cl14 | 0.37520 (8) | 0.5974 (1) | 0.40913 (6) | 0.0727 (5)* | |
Cl15 | 0.39510 (9) | 1.0019 (1) | 0.62300 (8) | 0.0820 (5)* | |
O16 | 0.0485 (2) | 0.6002 (3) | 0.3292 (1) | 0.056 (1)* | |
C17 | 0.0797 (3) | 0.6648 (5) | 0.2692 (2) | 0.068 (2)* | |
C18 | −0.0157 (3) | 0.6520 (5) | 0.1945 (2) | 0.054 (2)* | |
C19 | −0.0395 (3) | 0.5244 (5) | 0.1528 (2) | 0.062 (2)* | |
C20 | −0.1314 (4) | 0.5088 (5) | 0.0870 (2) | 0.068 (2)* | |
C21 | −0.1993 (3) | 0.6267 (5) | 0.0633 (2) | 0.060 (1)* | |
C22 | −0.1789 (3) | 0.7561 (5) | 0.1028 (2) | 0.060 (2)* | |
C23 | −0.0867 (3) | 0.7676 (5) | 0.1684 (2) | 0.057 (2)* | |
Cl24 | 0.0460 (1) | 0.3755 (2) | 0.18236 (9) | 0.1022 (7)* | |
Cl25 | −0.3179 (1) | 0.6083 (2) | −0.01819 (8) | 0.0986 (6)* | |
N26 | −0.1681 (2) | 0.7268 (4) | 0.3437 (2) | 0.053 (1)* | |
O27 | −0.2009 (2) | 0.6103 (3) | 0.3110 (2) | 0.073 (1)* | |
O28 | −0.1123 (2) | 0.7308 (4) | 0.4137 (2) | 0.085 (2)* | |
O29 | −0.1935 (2) | 0.8424 (3) | 0.3043 (2) | 0.071 (1)* | |
N51 | 0.4945 (2) | 0.6211 (3) | 0.1000 (2) | 0.048 (1)* | |
C52 | 0.5876 (3) | 0.6144 (6) | 0.1612 (2) | 0.063 (2)* | |
N53 | 0.6272 (3) | 0.7450 (5) | 0.1773 (2) | 0.073 (2)* | |
C54 | 0.5615 (4) | 0.8416 (5) | 0.1279 (2) | 0.065 (2)* | |
C55 | 0.4794 (3) | 0.7645 (4) | 0.0798 (2) | 0.054 (1)* | |
C56 | 0.4174 (3) | 0.5052 (4) | 0.0657 (2) | 0.055 (2)* | |
C57 | 0.3450 (3) | 0.4716 (4) | 0.1127 (2) | 0.051 (2)* | |
C58 | 0.2893 (3) | 0.6069 (4) | 0.1281 (2) | 0.046 (1)* | |
C59 | 0.1907 (3) | 0.6548 (4) | 0.0768 (2) | 0.055 (2)* | |
C60 | 0.1426 (3) | 0.7810 (5) | 0.0884 (2) | 0.057 (2)* | |
C61 | 0.1956 (3) | 0.8620 (4) | 0.1532 (2) | 0.059 (2)* | |
C62 | 0.2929 (3) | 0.8188 (4) | 0.2065 (2) | 0.060 (2)* | |
C63 | 0.3390 (3) | 0.6922 (4) | 0.1936 (2) | 0.052 (1)* | |
Cl64 | 0.1229 (1) | 0.5563 (2) | −0.00741 (7) | 0.0961 (6)* | |
Cl65 | 0.1355 (1) | 1.0216 (1) | 0.16860 (9) | 0.0931 (6)* | |
C67 | 0.3551 (3) | 0.3330 (4) | 0.2248 (2) | 0.061 (2)* | |
O66 | 0.4128 (2) | 0.4038 (3) | 0.1826 (2) | 0.057 (1)* | |
C68 | 0.4242 (3) | 0.2161 (4) | 0.2752 (2) | 0.050 (1)* | |
C69 | 0.3981 (3) | 0.1502 (4) | 0.3337 (2) | 0.049 (2)* | |
C70 | 0.4599 (3) | 0.0409 (4) | 0.3802 (2) | 0.054 (1)* | |
C71 | 0.5516 (3) | −0.0022 (4) | 0.3682 (2) | 0.056 (2)* | |
C72 | 0.5819 (3) | 0.0599 (5) | 0.3110 (3) | 0.065 (2)* | |
C73 | 0.5182 (3) | 0.1677 (4) | 0.2645 (2) | 0.063 (2)* | |
Cl74 | 0.28244 (9) | 0.2049 (1) | 0.35138 (7) | 0.0742 (5)* | |
Cl75 | 0.6296 (1) | −0.1393 (1) | 0.42668 (8) | 0.0841 (5)* | |
N76 | 0.6961 (3) | 0.2074 (4) | 0.1537 (2) | 0.056 (1)* | |
O77 | 0.7492 (3) | 0.0950 (4) | 0.1782 (2) | 0.090 (1)* | |
O78 | 0.7270 (3) | 0.3198 (4) | 0.1911 (3) | 0.113 (2)* | |
O79 | 0.6126 (3) | 0.2037 (4) | 0.0975 (2) | 0.095 (2)* | |
H2 | −0.1019 | 0.3987 | 0.3086 | 0.070* | |
H3 | −0.1359 | 0.1529 | 0.2738 | 0.078* | |
H4 | −0.0007 | −0.0052 | 0.3611 | 0.082* | |
H5 | 0.1272 | 0.1567 | 0.4553 | 0.067* | |
H6A | 0.1323 | 0.4278 | 0.4893 | 0.062* | |
H6B | 0.0243 | 0.5134 | 0.4496 | 0.062* | |
H7 | 0.1825 | 0.4878 | 0.3782 | 0.058* | |
H10 | 0.4408 | 0.8140 | 0.5194 | 0.060* | |
H12 | 0.1767 | 0.9232 | 0.5652 | 0.070* | |
H13 | 0.0789 | 0.7500 | 0.4786 | 0.067* | |
H17A | 0.1416 | 0.6143 | 0.2646 | 0.081* | |
H17B | 0.0988 | 0.7662 | 0.2811 | 0.081* | |
H20 | −0.1468 | 0.4214 | 0.0597 | 0.082* | |
H22 | −0.2260 | 0.8344 | 0.0860 | 0.072* | |
H23 | −0.0719 | 0.8551 | 0.1957 | 0.069* | |
H52 | 0.6187 | 0.5301 | 0.1878 | 0.076* | |
H53 | 0.6867 | 0.7664 | 0.2142 | 0.087* | |
H54 | 0.5713 | 0.9417 | 0.1274 | 0.078* | |
H55 | 0.4212 | 0.8024 | 0.0390 | 0.065* | |
H56A | 0.4566 | 0.4179 | 0.0622 | 0.066* | |
H56B | 0.3726 | 0.5330 | 0.0132 | 0.066* | |
H57 | 0.2896 | 0.4018 | 0.0833 | 0.061* | |
H60 | 0.0760 | 0.8104 | 0.0531 | 0.069* | |
H62 | 0.3272 | 0.8745 | 0.2508 | 0.072* | |
H63 | 0.4051 | 0.6629 | 0.2296 | 0.063* | |
H67A | 0.2894 | 0.2906 | 0.1886 | 0.074* | |
H67B | 0.3354 | 0.4031 | 0.2570 | 0.074* | |
H70 | 0.4395 | −0.0024 | 0.4188 | 0.065* | |
H72 | 0.6446 | 0.0298 | 0.3035 | 0.079* | |
H73 | 0.5384 | 0.2089 | 0.2253 | 0.075* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.043 (2) | 0.054 (2) | 0.046 (2) | −0.002 (2) | 0.012 (1) | −0.001 (1) |
C2 | 0.047 (2) | 0.063 (3) | 0.057 (2) | 0.000 (2) | 0.009 (2) | 0.000 (2) |
N3 | 0.059 (2) | 0.067 (2) | 0.061 (2) | −0.007 (2) | 0.012 (2) | −0.014 (2) |
C4 | 0.067 (3) | 0.058 (3) | 0.073 (3) | −0.001 (3) | 0.018 (2) | −0.003 (2) |
C5 | 0.054 (2) | 0.059 (3) | 0.051 (2) | 0.006 (2) | 0.013 (2) | 0.004 (2) |
C6 | 0.053 (2) | 0.055 (2) | 0.046 (2) | −0.007 (2) | 0.015 (2) | −0.001 (2) |
C7 | 0.040 (2) | 0.060 (2) | 0.046 (2) | 0.005 (2) | 0.016 (2) | 0.003 (2) |
C8 | 0.040 (2) | 0.049 (2) | 0.048 (2) | 0.000 (2) | 0.016 (2) | 0.007 (2) |
C9 | 0.041 (2) | 0.055 (2) | 0.046 (2) | 0.003 (2) | 0.022 (2) | 0.008 (2) |
C10 | 0.037 (2) | 0.049 (2) | 0.064 (2) | −0.004 (2) | 0.020 (2) | 0.014 (2) |
C11 | 0.050 (2) | 0.034 (2) | 0.068 (2) | −0.003 (2) | 0.020 (2) | 0.006 (2) |
C12 | 0.051 (2) | 0.045 (2) | 0.087 (3) | −0.001 (2) | 0.034 (2) | −0.002 (2) |
C13 | 0.037 (2) | 0.056 (2) | 0.076 (3) | −0.003 (2) | 0.023 (2) | −0.004 (2) |
Cl14 | 0.0543 (5) | 0.0973 (9) | 0.0790 (7) | −0.0005 (6) | 0.0389 (5) | −0.0129 (7) |
Cl15 | 0.0680 (7) | 0.0587 (7) | 0.122 (1) | −0.0224 (6) | 0.0377 (7) | −0.0266 (7) |
O16 | 0.045 (1) | 0.078 (2) | 0.045 (1) | −0.001 (1) | 0.016 (1) | 0.011 (1) |
C17 | 0.062 (3) | 0.088 (3) | 0.054 (2) | −0.005 (2) | 0.021 (2) | 0.012 (2) |
C18 | 0.056 (2) | 0.068 (3) | 0.044 (2) | 0.000 (2) | 0.024 (2) | 0.007 (2) |
C19 | 0.072 (3) | 0.061 (3) | 0.057 (2) | 0.018 (2) | 0.027 (2) | 0.008 (2) |
C20 | 0.083 (3) | 0.066 (3) | 0.057 (2) | 0.002 (3) | 0.027 (2) | −0.005 (2) |
C21 | 0.059 (2) | 0.062 (3) | 0.051 (2) | −0.001 (2) | 0.011 (2) | 0.010 (2) |
C22 | 0.061 (3) | 0.061 (3) | 0.061 (3) | 0.008 (2) | 0.026 (2) | 0.014 (2) |
C23 | 0.072 (3) | 0.052 (2) | 0.055 (2) | −0.003 (2) | 0.031 (2) | 0.003 (2) |
Cl24 | 0.104 (1) | 0.091 (1) | 0.107 (1) | 0.0485 (9) | 0.0324 (8) | 0.0100 (8) |
Cl25 | 0.0864 (8) | 0.098 (1) | 0.0809 (8) | −0.0125 (8) | −0.0090 (7) | 0.0155 (8) |
N26 | 0.039 (2) | 0.070 (3) | 0.048 (2) | 0.004 (2) | 0.014 (2) | −0.001 (2) |
O27 | 0.060 (2) | 0.056 (2) | 0.090 (2) | −0.005 (2) | 0.010 (2) | 0.000 (2) |
O28 | 0.059 (2) | 0.137 (3) | 0.049 (2) | 0.022 (2) | 0.009 (1) | −0.006 (2) |
O29 | 0.071 (2) | 0.059 (2) | 0.076 (2) | −0.002 (2) | 0.017 (2) | 0.009 (2) |
N51 | 0.051 (2) | 0.049 (2) | 0.044 (2) | 0.003 (2) | 0.016 (1) | 0.005 (1) |
C52 | 0.054 (2) | 0.086 (3) | 0.049 (2) | 0.022 (3) | 0.019 (2) | 0.019 (2) |
N53 | 0.051 (2) | 0.107 (3) | 0.056 (2) | −0.018 (2) | 0.014 (2) | −0.005 (2) |
C54 | 0.071 (3) | 0.067 (3) | 0.055 (2) | −0.015 (3) | 0.020 (2) | −0.005 (2) |
C55 | 0.055 (2) | 0.056 (3) | 0.045 (2) | −0.003 (2) | 0.011 (2) | 0.000 (2) |
C56 | 0.074 (3) | 0.043 (2) | 0.054 (2) | −0.004 (2) | 0.030 (2) | −0.008 (2) |
C57 | 0.061 (2) | 0.042 (2) | 0.049 (2) | −0.003 (2) | 0.020 (2) | 0.002 (2) |
C58 | 0.054 (2) | 0.043 (2) | 0.041 (2) | −0.003 (2) | 0.015 (2) | 0.005 (2) |
C59 | 0.058 (2) | 0.058 (3) | 0.043 (2) | −0.009 (2) | 0.010 (2) | −0.003 (2) |
C60 | 0.052 (2) | 0.059 (3) | 0.057 (2) | 0.007 (2) | 0.014 (2) | 0.008 (2) |
C61 | 0.061 (2) | 0.048 (2) | 0.071 (3) | 0.001 (2) | 0.029 (2) | 0.000 (2) |
C62 | 0.069 (3) | 0.049 (2) | 0.059 (2) | −0.008 (2) | 0.020 (2) | −0.017 (2) |
C63 | 0.051 (2) | 0.054 (2) | 0.045 (2) | −0.004 (2) | 0.009 (2) | −0.002 (2) |
Cl64 | 0.0855 (8) | 0.109 (1) | 0.0658 (7) | 0.0046 (8) | −0.0089 (6) | −0.0328 (7) |
Cl65 | 0.0869 (8) | 0.0570 (7) | 0.135 (1) | 0.0124 (7) | 0.0391 (8) | −0.0156 (8) |
C67 | 0.072 (3) | 0.055 (3) | 0.072 (3) | 0.010 (2) | 0.043 (2) | 0.018 (2) |
O66 | 0.063 (2) | 0.051 (2) | 0.061 (2) | 0.005 (1) | 0.025 (1) | 0.015 (1) |
C68 | 0.057 (2) | 0.042 (2) | 0.056 (2) | 0.002 (2) | 0.027 (2) | −0.001 (2) |
C69 | 0.054 (2) | 0.044 (2) | 0.057 (2) | −0.001 (2) | 0.027 (2) | −0.005 (2) |
C70 | 0.064 (2) | 0.044 (2) | 0.055 (2) | −0.005 (2) | 0.023 (2) | 0.001 (2) |
C71 | 0.057 (2) | 0.039 (2) | 0.064 (2) | −0.002 (2) | 0.011 (2) | −0.001 (2) |
C72 | 0.069 (3) | 0.053 (3) | 0.083 (3) | 0.011 (2) | 0.038 (2) | 0.003 (2) |
C73 | 0.077 (3) | 0.054 (2) | 0.070 (3) | 0.014 (2) | 0.042 (2) | 0.019 (2) |
Cl74 | 0.0754 (7) | 0.0831 (8) | 0.0802 (7) | 0.0142 (7) | 0.0476 (6) | 0.0106 (6) |
Cl75 | 0.0829 (8) | 0.0547 (6) | 0.1007 (9) | 0.0142 (6) | 0.0151 (7) | 0.0178 (6) |
N76 | 0.061 (2) | 0.050 (2) | 0.053 (2) | −0.004 (2) | 0.014 (2) | −0.001 (2) |
O77 | 0.083 (2) | 0.054 (2) | 0.104 (2) | 0.002 (2) | −0.003 (2) | −0.003 (2) |
O78 | 0.095 (3) | 0.067 (2) | 0.136 (3) | 0.010 (2) | −0.012 (2) | −0.026 (2) |
O79 | 0.097 (2) | 0.101 (3) | 0.057 (2) | 0.012 (2) | −0.010 (2) | 0.000 (2) |
Geometric parameters (Å, º) top
N1—C2 | 1.334 (4) | N51—C52 | 1.343 (5) |
N1—C5 | 1.367 (5) | N51—C55 | 1.364 (5) |
N1—C6 | 1.470 (5) | N51—C56 | 1.454 (5) |
C2—H2 | 0.930 | C52—H52 | 0.930 |
C2—N3 | 1.307 (6) | C52—N53 | 1.302 (7) |
N3—H3 | 0.860 | N53—H53 | 0.860 |
N3—C4 | 1.365 (5) | N53—C54 | 1.344 (6) |
C4—H4 | 0.930 | C54—H54 | 0.930 |
C4—C5 | 1.342 (6) | C54—C55 | 1.336 (6) |
C5—H5 | 0.930 | C55—H55 | 0.930 |
C6—H6A | 0.970 | C56—H56A | 0.970 |
C6—H6B | 0.970 | C56—H56B | 0.970 |
C6—C7 | 1.524 (6) | C56—C57 | 1.527 (7) |
C7—H7 | 0.980 | C57—H57 | 0.980 |
C7—C8 | 1.509 (5) | C57—C58 | 1.522 (6) |
C7—O16 | 1.418 (4) | C57—O66 | 1.421 (4) |
C8—C9 | 1.400 (5) | C58—C59 | 1.384 (5) |
C8—C13 | 1.396 (6) | C58—C63 | 1.388 (5) |
C9—C10 | 1.389 (5) | C59—C60 | 1.375 (6) |
C9—Cl14 | 1.740 (4) | C59—Cl64 | 1.739 (4) |
C10—H10 | 0.930 | C60—H60 | 0.930 |
C10—C11 | 1.374 (6) | C60—C61 | 1.367 (6) |
C11—C12 | 1.376 (6) | C61—C62 | 1.372 (5) |
C11—Cl15 | 1.727 (4) | C61—Cl65 | 1.738 (5) |
C12—H12 | 0.930 | C62—H62 | 0.930 |
C12—C13 | 1.382 (5) | C62—C63 | 1.372 (6) |
C13—H13 | 0.930 | C63—H63 | 0.930 |
O16—C17 | 1.432 (6) | C67—H67A | 0.970 |
C17—H17A | 0.970 | C67—H67B | 0.970 |
C17—H17B | 0.970 | C67—O66 | 1.420 (6) |
C17—C18 | 1.503 (5) | C67—C68 | 1.499 (5) |
C18—C19 | 1.375 (6) | C68—C69 | 1.377 (6) |
C18—C23 | 1.387 (6) | C68—C73 | 1.397 (7) |
C19—C20 | 1.384 (5) | C69—C70 | 1.383 (5) |
C19—Cl24 | 1.736 (5) | C69—Cl74 | 1.745 (5) |
C20—H20 | 0.930 | C70—H70 | 0.930 |
C20—C21 | 1.377 (6) | C70—C71 | 1.364 (6) |
C21—C22 | 1.368 (6) | C71—C72 | 1.370 (7) |
C21—Cl25 | 1.751 (4) | C71—Cl75 | 1.738 (4) |
C22—H22 | 0.930 | C72—H72 | 0.930 |
C22—C23 | 1.381 (5) | C72—C73 | 1.382 (6) |
C23—H23 | 0.930 | C73—H73 | 0.930 |
N26—O27 | 1.229 (5) | N76—O77 | 1.241 (5) |
N26—O28 | 1.233 (4) | N76—O78 | 1.227 (5) |
N26—O29 | 1.261 (5) | N76—O79 | 1.216 (4) |
C2—N1—C5 | 107.8 (3) | C52—N51—C55 | 105.9 (3) |
C2—N1—C6 | 126.1 (3) | C52—N51—C56 | 128.6 (3) |
C5—N1—C6 | 126.1 (3) | C55—N51—C56 | 125.2 (3) |
N1—C2—H2 | 125.8 | N51—C52—H52 | 125.6 |
N1—C2—N3 | 108.5 (4) | N51—C52—N53 | 108.9 (4) |
H2—C2—N3 | 125.8 | H52—C52—N53 | 125.6 |
C2—N3—H3 | 125.2 | C52—N53—H53 | 124.9 |
C2—N3—C4 | 109.6 (4) | C52—N53—C54 | 110.1 (4) |
H3—N3—C4 | 125.2 | H53—N53—C54 | 124.9 |
N3—C4—H4 | 126.8 | N53—C54—H54 | 127.0 |
N3—C4—C5 | 106.3 (4) | N53—C54—C55 | 106.0 (4) |
H4—C4—C5 | 126.9 | H54—C54—C55 | 127.0 |
N1—C5—C4 | 107.8 (4) | N51—C55—C54 | 109.0 (4) |
N1—C5—H5 | 126.1 | N51—C55—H55 | 125.5 |
C4—C5—H5 | 126.1 | C54—C55—H55 | 125.5 |
N1—C6—H6A | 109.1 | N51—C56—H56A | 109.0 |
N1—C6—H6B | 109.1 | N51—C56—H56B | 109.0 |
N1—C6—C7 | 112.6 (3) | N51—C56—C57 | 112.9 (3) |
H6A—C6—H6B | 107.8 | H56A—C56—H56B | 107.8 |
H6A—C6—C7 | 109.1 | H56A—C56—C57 | 109.0 |
H6B—C6—C7 | 109.1 | H56B—C56—C57 | 109.0 |
C6—C7—H7 | 109.4 | C56—C57—H57 | 108.7 |
C6—C7—C8 | 110.6 (3) | C56—C57—C58 | 112.3 (3) |
C6—C7—O16 | 104.4 (3) | C56—C57—O66 | 105.9 (3) |
H7—C7—C8 | 109.4 | H57—C57—C58 | 108.7 |
H7—C7—O16 | 109.4 | H57—C57—O66 | 108.7 |
C8—C7—O16 | 113.5 (3) | C58—C57—O66 | 112.6 (3) |
C7—C8—C9 | 123.7 (3) | C57—C58—C59 | 122.4 (4) |
C7—C8—C13 | 120.5 (3) | C57—C58—C63 | 120.6 (3) |
C9—C8—C13 | 115.8 (4) | C59—C58—C63 | 116.9 (3) |
C8—C9—C10 | 122.6 (3) | C58—C59—C60 | 122.7 (4) |
C8—C9—Cl14 | 120.7 (3) | C58—C59—Cl64 | 120.3 (3) |
C10—C9—Cl14 | 116.8 (3) | C60—C59—Cl64 | 117.0 (3) |
C9—C10—H10 | 120.5 | C59—C60—H60 | 121.0 |
C9—C10—C11 | 119.0 (3) | C59—C60—C61 | 118.1 (4) |
H10—C10—C11 | 120.5 | H60—C60—C61 | 121.0 |
C10—C11—C12 | 120.4 (4) | C60—C61—C62 | 121.7 (4) |
C10—C11—Cl15 | 119.4 (3) | C60—C61—Cl65 | 118.5 (3) |
C12—C11—Cl15 | 120.2 (3) | C62—C61—Cl65 | 119.8 (3) |
C11—C12—H12 | 120.2 | C61—C62—H62 | 120.5 |
C11—C12—C13 | 119.6 (4) | C61—C62—C63 | 119.1 (4) |
H12—C12—C13 | 120.2 | H62—C62—C63 | 120.5 |
C8—C13—C12 | 122.4 (4) | C58—C63—C62 | 121.6 (4) |
C8—C13—H13 | 118.8 | C58—C63—H63 | 119.2 |
C12—C13—H13 | 118.8 | C62—C63—H63 | 119.2 |
C7—O16—C17 | 115.6 (3) | H67A—C67—H67B | 108.2 |
O16—C17—H17A | 110.4 | H67A—C67—O66 | 109.8 |
O16—C17—H17B | 110.4 | H67A—C67—C68 | 109.8 |
O16—C17—C18 | 106.8 (3) | H67B—C67—O66 | 109.8 |
H17A—C17—H17B | 108.6 | H67B—C67—C68 | 109.8 |
H17A—C17—C18 | 110.4 | O66—C67—C68 | 109.6 (3) |
H17B—C17—C18 | 110.4 | C57—O66—C67 | 113.6 (3) |
C17—C18—C19 | 121.8 (4) | C67—C68—C69 | 121.9 (3) |
C17—C18—C23 | 120.2 (4) | C67—C68—C73 | 121.5 (4) |
C19—C18—C23 | 117.9 (4) | C69—C68—C73 | 116.6 (4) |
C18—C19—C20 | 122.1 (4) | C68—C69—C70 | 122.9 (3) |
C18—C19—Cl24 | 120.2 (3) | C68—C69—Cl74 | 119.6 (3) |
C20—C19—Cl24 | 117.8 (3) | C70—C69—Cl74 | 117.5 (3) |
C19—C20—H20 | 121.0 | C69—C70—H70 | 120.7 |
C19—C20—C21 | 117.9 (4) | C69—C70—C71 | 118.6 (4) |
H20—C20—C21 | 121.0 | H70—C70—C71 | 120.7 |
C20—C21—C22 | 122.2 (4) | C70—C71—C72 | 121.2 (4) |
C20—C21—Cl25 | 118.8 (3) | C70—C71—Cl75 | 118.7 (3) |
C22—C21—Cl25 | 119.0 (3) | C72—C71—Cl75 | 120.1 (3) |
C21—C22—H22 | 120.8 | C71—C72—H72 | 120.3 |
C21—C22—C23 | 118.4 (4) | C71—C72—C73 | 119.3 (4) |
H22—C22—C23 | 120.8 | H72—C72—C73 | 120.3 |
C18—C23—C22 | 121.6 (4) | C68—C73—C72 | 121.4 (4) |
C18—C23—H23 | 119.2 | C68—C73—H73 | 119.3 |
C22—C23—H23 | 119.2 | C72—C73—H73 | 119.3 |
O27—N26—O28 | 120.7 (3) | O77—N76—O78 | 117.7 (4) |
O27—N26—O29 | 118.6 (4) | O77—N76—O79 | 120.8 (4) |
O28—N26—O29 | 120.7 (3) | O78—N76—O79 | 121.4 (4) |
C5—N1—C2—H2 | −179.8 | C55—N51—C52—H52 | 179.8 |
C5—N1—C2—N3 | 0.2 (5) | C55—N51—C52—N53 | −0.2 (5) |
C6—N1—C2—H2 | 2.2 | C56—N51—C52—H52 | 5.8 |
C6—N1—C2—N3 | −177.8 (4) | C56—N51—C52—N53 | −174.2 (4) |
C2—N1—C5—C4 | −0.5 (5) | C52—N51—C55—C54 | −0.1 (5) |
C2—N1—C5—H5 | 179.4 | C52—N51—C55—H55 | 179.9 |
C6—N1—C5—C4 | 177.5 (4) | C56—N51—C55—C54 | 174.1 (4) |
C6—N1—C5—H5 | −2.5 | C56—N51—C55—H55 | −5.9 |
C2—N1—C6—H6A | 165.2 | C52—N51—C56—H56A | −43.2 |
C2—N1—C6—H6B | 47.7 | C52—N51—C56—H56B | −160.6 |
C2—N1—C6—C7 | −73.6 (5) | C52—N51—C56—C57 | 78.1 (5) |
C5—N1—C6—H6A | −12.5 | C55—N51—C56—H56A | 143.9 |
C5—N1—C6—H6B | −130.0 | C55—N51—C56—H56B | 26.5 |
C5—N1—C6—C7 | 108.7 (4) | C55—N51—C56—C57 | −94.8 (4) |
N1—C2—N3—H3 | −179.8 | N51—C52—N53—H53 | −179.5 |
N1—C2—N3—C4 | 0.2 (5) | N51—C52—N53—C54 | 0.5 (5) |
H2—C2—N3—H3 | 0.2 | H52—C52—N53—H53 | 0.5 |
H2—C2—N3—C4 | −179.8 | H52—C52—N53—C54 | −179.5 |
C2—N3—C4—H4 | 179.5 | C52—N53—C54—H54 | 179.5 |
C2—N3—C4—C5 | −0.5 (5) | C52—N53—C54—C55 | −0.5 (5) |
H3—N3—C4—H4 | −0.5 | H53—N53—C54—H54 | −0.5 |
H3—N3—C4—C5 | 179.5 | H53—N53—C54—C55 | 179.5 |
N3—C4—C5—N1 | 0.6 (5) | N53—C54—C55—N51 | 0.4 (5) |
N3—C4—C5—H5 | −179.4 | N53—C54—C55—H55 | −179.6 |
H4—C4—C5—N1 | −179.4 | H54—C54—C55—N51 | −179.6 |
H4—C4—C5—H5 | 0.6 | H54—C54—C55—H55 | 0.4 |
N1—C6—C7—H7 | −50.4 | N51—C56—C57—H57 | 173.1 |
N1—C6—C7—C8 | −171.0 (3) | N51—C56—C57—C58 | 52.9 (4) |
N1—C6—C7—O16 | 66.5 (4) | N51—C56—C57—O66 | −70.4 (4) |
H6A—C6—C7—H7 | 70.8 | H56A—C56—C57—H57 | −65.6 |
H6A—C6—C7—C8 | −49.7 | H56A—C56—C57—C58 | 174.1 |
H6A—C6—C7—O16 | −172.2 | H56A—C56—C57—O66 | 50.9 |
H6B—C6—C7—H7 | −171.7 | H56B—C56—C57—H57 | 51.8 |
H6B—C6—C7—C8 | 67.8 | H56B—C56—C57—C58 | −68.4 |
H6B—C6—C7—O16 | −54.7 | H56B—C56—C57—O66 | 168.3 |
C6—C7—C8—C9 | 127.0 (4) | C56—C57—C58—C59 | 88.4 (5) |
C6—C7—C8—C13 | −51.1 (5) | C56—C57—C58—C63 | −88.4 (4) |
H7—C7—C8—C9 | 6.5 | H57—C57—C58—C59 | −31.8 |
H7—C7—C8—C13 | −171.6 | H57—C57—C58—C63 | 151.4 |
O16—C7—C8—C9 | −115.9 (4) | O66—C57—C58—C59 | −152.2 (4) |
O16—C7—C8—C13 | 65.9 (5) | O66—C57—C58—C63 | 31.0 (5) |
C6—C7—O16—C17 | −167.0 (3) | C56—C57—O66—C67 | −165.4 (3) |
H7—C7—O16—C17 | −50.0 | H57—C57—O66—C67 | −48.8 |
C8—C7—O16—C17 | 72.5 (4) | C58—C57—O66—C67 | 71.6 (4) |
C7—C8—C9—C10 | −174.8 (4) | C57—C58—C59—C60 | −176.5 (4) |
C7—C8—C9—Cl14 | 5.6 (5) | C57—C58—C59—Cl64 | 2.4 (6) |
C13—C8—C9—C10 | 3.4 (6) | C63—C58—C59—C60 | 0.4 (6) |
C13—C8—C9—Cl14 | −176.2 (3) | C63—C58—C59—Cl64 | 179.4 (3) |
C7—C8—C13—C12 | 175.0 (4) | C57—C58—C63—C62 | 176.5 (4) |
C7—C8—C13—H13 | −5.0 | C57—C58—C63—H63 | −3.5 |
C9—C8—C13—C12 | −3.3 (6) | C59—C58—C63—C62 | −0.5 (6) |
C9—C8—C13—H13 | 176.8 | C59—C58—C63—H63 | 179.5 |
C8—C9—C10—H10 | −179.8 | C58—C59—C60—H60 | −179.5 |
C8—C9—C10—C11 | 0.2 (6) | C58—C59—C60—C61 | 0.5 (6) |
Cl14—C9—C10—H10 | −0.2 | Cl64—C59—C60—H60 | 1.5 |
Cl14—C9—C10—C11 | 179.8 (3) | Cl64—C59—C60—C61 | −178.6 (3) |
C9—C10—C11—C12 | −4.1 (6) | C59—C60—C61—C62 | −1.2 (7) |
C9—C10—C11—Cl15 | 176.4 (3) | C59—C60—C61—Cl65 | −179.9 (3) |
H10—C10—C11—C12 | 175.9 | H60—C60—C61—C62 | 178.8 |
H10—C10—C11—Cl15 | −3.6 | H60—C60—C61—Cl65 | 0.1 |
C10—C11—C12—H12 | −175.8 | C60—C61—C62—H62 | −178.9 |
C10—C11—C12—C13 | 4.2 (6) | C60—C61—C62—C63 | 1.1 (7) |
Cl15—C11—C12—H12 | 3.8 | Cl65—C61—C62—H62 | −0.3 |
Cl15—C11—C12—C13 | −176.3 (3) | Cl65—C61—C62—C63 | 179.8 (3) |
C11—C12—C13—C8 | −0.4 (6) | C61—C62—C63—C58 | −0.2 (6) |
C11—C12—C13—H13 | 179.6 | C61—C62—C63—H63 | 179.8 |
H12—C12—C13—C8 | 179.6 | H62—C62—C63—C58 | 179.8 |
H12—C12—C13—H13 | −0.4 | H62—C62—C63—H63 | −0.2 |
C7—O16—C17—H17A | 36.2 | H67A—C67—O66—C57 | 35.4 |
C7—O16—C17—H17B | −83.9 | H67B—C67—O66—C57 | −83.4 |
C7—O16—C17—C18 | 156.1 (3) | C68—C67—O66—C57 | 156.0 (3) |
O16—C17—C18—C19 | −79.3 (5) | H67A—C67—C68—C69 | −72.9 |
O16—C17—C18—C23 | 96.4 (4) | H67A—C67—C68—C73 | 106.6 |
H17A—C17—C18—C19 | 40.7 | H67B—C67—C68—C69 | 45.9 |
H17A—C17—C18—C23 | −143.6 | H67B—C67—C68—C73 | −134.6 |
H17B—C17—C18—C19 | 160.7 | O66—C67—C68—C69 | 166.5 (4) |
H17B—C17—C18—C23 | −23.5 | O66—C67—C68—C73 | −14.0 (5) |
C17—C18—C19—C20 | 175.3 (4) | C67—C68—C69—C70 | 179.1 (4) |
C17—C18—C19—Cl24 | −4.1 (6) | C67—C68—C69—Cl74 | −0.9 (6) |
C23—C18—C19—C20 | −0.5 (7) | C73—C68—C69—C70 | −0.4 (6) |
C23—C18—C19—Cl24 | −179.9 (3) | C73—C68—C69—Cl74 | 179.6 (3) |
C17—C18—C23—C22 | −175.6 (4) | C67—C68—C73—C72 | −180.0 (4) |
C17—C18—C23—H23 | 4.4 | C67—C68—C73—H73 | 0.0 |
C19—C18—C23—C22 | 0.2 (6) | C69—C68—C73—C72 | −0.5 (6) |
C19—C18—C23—H23 | −179.8 | C69—C68—C73—H73 | 179.5 |
C18—C19—C20—H20 | −179.3 | C68—C69—C70—H70 | −179.1 |
C18—C19—C20—C21 | 0.7 (7) | C68—C69—C70—C71 | 0.9 (6) |
Cl24—C19—C20—H20 | 0.1 | Cl74—C69—C70—H70 | 0.9 |
Cl24—C19—C20—C21 | −179.9 (3) | Cl74—C69—C70—C71 | −179.1 (3) |
C19—C20—C21—C22 | −0.5 (7) | C69—C70—C71—C72 | −0.7 (6) |
C19—C20—C21—Cl25 | −178.4 (3) | C69—C70—C71—Cl75 | 179.9 (3) |
H20—C20—C21—C22 | 179.5 | H70—C70—C71—C72 | 179.3 |
H20—C20—C21—Cl25 | 1.6 | H70—C70—C71—Cl75 | −0.2 |
C20—C21—C22—H22 | −179.7 | C70—C71—C72—H72 | 179.8 |
C20—C21—C22—C23 | 0.3 (7) | C70—C71—C72—C73 | −0.2 (7) |
Cl25—C21—C22—H22 | −1.9 | Cl75—C71—C72—H72 | −0.7 |
Cl25—C21—C22—C23 | 178.1 (3) | Cl75—C71—C72—C73 | 179.3 (3) |
C21—C22—C23—C18 | −0.1 (7) | C71—C72—C73—C68 | 0.8 (7) |
C21—C22—C23—H23 | 179.9 | C71—C72—C73—H73 | −179.2 |
H22—C22—C23—C18 | 179.9 | H72—C72—C73—C68 | −179.2 |
H22—C22—C23—H23 | −0.1 | H72—C72—C73—H73 | 0.8 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O27 | 0.93 | 2.35 | 3.199 (6) | 151 |
C13—H13···O28 | 0.93 | 2.39 | 3.287 (6) | 162 |
C52—H52···O78 | 0.93 | 2.39 | 3.213 (7) | 147 |
N3—H3···O77i | 0.86 | 1.94 | 2.801 (5) | 174 |
N3—H3···O78i | 0.86 | 2.45 | 2.996 (6) | 122 |
C5—H5···O28ii | 0.93 | 2.57 | 3.016 (6) | 110 |
N53—H53···O27iii | 0.86 | 2.36 | 2.962 (5) | 128 |
N53—H53···O29iii | 0.86 | 1.97 | 2.819 (5) | 169 |
C54—H54···O79iv | 0.93 | 2.57 | 3.480 (7) | 166 |
C54—H54···O77iv | 0.93 | 2.62 | 3.291 (6) | 130 |
C55—H55···O79v | 0.93 | 2.54 | 3.088 (6) | 118 |
Symmetry codes: (i) x−1, y, z; (ii) −x, y−1/2, −z+1; (iii) x+1, y, z; (iv) x, y+1, z; (v) −x+1, y+1/2, −z. |