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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804003058/na6291sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804003058/na6291Isup2.hkl
Contains datablock I

CCDC reference: 236075

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.042
  • wR factor = 0.101
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT150_ALERT_1_C Volume as Calculated Differs from that Given = 2082.00 Ang-3 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C21 PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... N26 PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... N76 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT431_ALERT_2_C Short Inter HL..A Contact Cl14 .. Cl15 = 3.41 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Cl15 .. Cl75 = 3.41 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O28 .. C5 = 3.01 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H54 .. O77 = 2.62 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 N O3
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 7254 Count of symmetry unique reflns 3912 Completeness (_total/calc) 185.43% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3342 Fraction of Friedel pairs measured 0.854 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 6 ALERT type 4 Improvement, methodology, query or suggestion

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+·NO3F(000) = 976
Mr = 479.13Dx = 1.528 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 13.23 (1) ÅCell parameters from 24 reflections
b = 9.191 (7) Åθ = 7.7–10.3°
c = 18.30 (2) ŵ = 0.60 mm1
β = 110.63 (8)°T = 293 K
V = 2082 (3) Å3Prism, colourless
Z = 40.60 × 0.50 × 0.40 mm
Data collection top
Stoe STADI4 four-circle
diffractometer
Rint = 0.020
ω scansθmax = 25.0°
Absorption correction: ψ scan
(EMPIR; Stoe & Cie, 1992)
h = 1515
Tmin = 0.721, Tmax = 0.787k = 1010
9914 measured reflectionsl = 2121
7254 independent reflections3 standard reflections every 60 min
5518 reflections with F2 > 2σ(F2) intensity decay: none
Refinement top
Refinement on F2H-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) = 0.101Δρmax = 0.25 e Å3
S = 1.03Δρmin = 0.32 e Å3
7254 reflectionsAbsolute structure: Flack (1983); 3357 Friedel pairs
523 parametersAbsolute structure parameter: 0.02 (5)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.0295 (2)0.3243 (4)0.3961 (2)0.048 (1)*
C20.0608 (3)0.3190 (5)0.3334 (2)0.058 (2)*
N30.0817 (3)0.1829 (4)0.3128 (2)0.065 (1)*
C40.0044 (3)0.0958 (5)0.3627 (2)0.068 (2)*
C50.0654 (3)0.1848 (5)0.4144 (2)0.056 (2)*
C60.0794 (3)0.4559 (4)0.4394 (2)0.052 (1)*
C70.1345 (3)0.5490 (4)0.3954 (2)0.048 (1)*
C80.1992 (3)0.6691 (4)0.4470 (2)0.046 (1)*
C90.3084 (3)0.6952 (4)0.4598 (2)0.045 (1)*
C100.3684 (3)0.7991 (4)0.5123 (2)0.050 (2)*
C110.3193 (3)0.8796 (4)0.5536 (2)0.051 (1)*
C120.2106 (3)0.8640 (4)0.5396 (3)0.058 (2)*
C130.1522 (3)0.7599 (4)0.4873 (2)0.056 (2)*
Cl140.37520 (8)0.5974 (1)0.40913 (6)0.0727 (5)*
Cl150.39510 (9)1.0019 (1)0.62300 (8)0.0820 (5)*
O160.0485 (2)0.6002 (3)0.3292 (1)0.056 (1)*
C170.0797 (3)0.6648 (5)0.2692 (2)0.068 (2)*
C180.0157 (3)0.6520 (5)0.1945 (2)0.054 (2)*
C190.0395 (3)0.5244 (5)0.1528 (2)0.062 (2)*
C200.1314 (4)0.5088 (5)0.0870 (2)0.068 (2)*
C210.1993 (3)0.6267 (5)0.0633 (2)0.060 (1)*
C220.1789 (3)0.7561 (5)0.1028 (2)0.060 (2)*
C230.0867 (3)0.7676 (5)0.1684 (2)0.057 (2)*
Cl240.0460 (1)0.3755 (2)0.18236 (9)0.1022 (7)*
Cl250.3179 (1)0.6083 (2)0.01819 (8)0.0986 (6)*
N260.1681 (2)0.7268 (4)0.3437 (2)0.053 (1)*
O270.2009 (2)0.6103 (3)0.3110 (2)0.073 (1)*
O280.1123 (2)0.7308 (4)0.4137 (2)0.085 (2)*
O290.1935 (2)0.8424 (3)0.3043 (2)0.071 (1)*
N510.4945 (2)0.6211 (3)0.1000 (2)0.048 (1)*
C520.5876 (3)0.6144 (6)0.1612 (2)0.063 (2)*
N530.6272 (3)0.7450 (5)0.1773 (2)0.073 (2)*
C540.5615 (4)0.8416 (5)0.1279 (2)0.065 (2)*
C550.4794 (3)0.7645 (4)0.0798 (2)0.054 (1)*
C560.4174 (3)0.5052 (4)0.0657 (2)0.055 (2)*
C570.3450 (3)0.4716 (4)0.1127 (2)0.051 (2)*
C580.2893 (3)0.6069 (4)0.1281 (2)0.046 (1)*
C590.1907 (3)0.6548 (4)0.0768 (2)0.055 (2)*
C600.1426 (3)0.7810 (5)0.0884 (2)0.057 (2)*
C610.1956 (3)0.8620 (4)0.1532 (2)0.059 (2)*
C620.2929 (3)0.8188 (4)0.2065 (2)0.060 (2)*
C630.3390 (3)0.6922 (4)0.1936 (2)0.052 (1)*
Cl640.1229 (1)0.5563 (2)0.00741 (7)0.0961 (6)*
Cl650.1355 (1)1.0216 (1)0.16860 (9)0.0931 (6)*
C670.3551 (3)0.3330 (4)0.2248 (2)0.061 (2)*
O660.4128 (2)0.4038 (3)0.1826 (2)0.057 (1)*
C680.4242 (3)0.2161 (4)0.2752 (2)0.050 (1)*
C690.3981 (3)0.1502 (4)0.3337 (2)0.049 (2)*
C700.4599 (3)0.0409 (4)0.3802 (2)0.054 (1)*
C710.5516 (3)0.0022 (4)0.3682 (2)0.056 (2)*
C720.5819 (3)0.0599 (5)0.3110 (3)0.065 (2)*
C730.5182 (3)0.1677 (4)0.2645 (2)0.063 (2)*
Cl740.28244 (9)0.2049 (1)0.35138 (7)0.0742 (5)*
Cl750.6296 (1)0.1393 (1)0.42668 (8)0.0841 (5)*
N760.6961 (3)0.2074 (4)0.1537 (2)0.056 (1)*
O770.7492 (3)0.0950 (4)0.1782 (2)0.090 (1)*
O780.7270 (3)0.3198 (4)0.1911 (3)0.113 (2)*
O790.6126 (3)0.2037 (4)0.0975 (2)0.095 (2)*
H20.10190.39870.30860.070*
H30.13590.15290.27380.078*
H40.00070.00520.36110.082*
H50.12720.15670.45530.067*
H6A0.13230.42780.48930.062*
H6B0.02430.51340.44960.062*
H70.18250.48780.37820.058*
H100.44080.81400.51940.060*
H120.17670.92320.56520.070*
H130.07890.75000.47860.067*
H17A0.14160.61430.26460.081*
H17B0.09880.76620.28110.081*
H200.14680.42140.05970.082*
H220.22600.83440.08600.072*
H230.07190.85510.19570.069*
H520.61870.53010.18780.076*
H530.68670.76640.21420.087*
H540.57130.94170.12740.078*
H550.42120.80240.03900.065*
H56A0.45660.41790.06220.066*
H56B0.37260.53300.01320.066*
H570.28960.40180.08330.061*
H600.07600.81040.05310.069*
H620.32720.87450.25080.072*
H630.40510.66290.22960.063*
H67A0.28940.29060.18860.074*
H67B0.33540.40310.25700.074*
H700.43950.00240.41880.065*
H720.64460.02980.30350.079*
H730.53840.20890.22530.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.043 (2)0.054 (2)0.046 (2)0.002 (2)0.012 (1)0.001 (1)
C20.047 (2)0.063 (3)0.057 (2)0.000 (2)0.009 (2)0.000 (2)
N30.059 (2)0.067 (2)0.061 (2)0.007 (2)0.012 (2)0.014 (2)
C40.067 (3)0.058 (3)0.073 (3)0.001 (3)0.018 (2)0.003 (2)
C50.054 (2)0.059 (3)0.051 (2)0.006 (2)0.013 (2)0.004 (2)
C60.053 (2)0.055 (2)0.046 (2)0.007 (2)0.015 (2)0.001 (2)
C70.040 (2)0.060 (2)0.046 (2)0.005 (2)0.016 (2)0.003 (2)
C80.040 (2)0.049 (2)0.048 (2)0.000 (2)0.016 (2)0.007 (2)
C90.041 (2)0.055 (2)0.046 (2)0.003 (2)0.022 (2)0.008 (2)
C100.037 (2)0.049 (2)0.064 (2)0.004 (2)0.020 (2)0.014 (2)
C110.050 (2)0.034 (2)0.068 (2)0.003 (2)0.020 (2)0.006 (2)
C120.051 (2)0.045 (2)0.087 (3)0.001 (2)0.034 (2)0.002 (2)
C130.037 (2)0.056 (2)0.076 (3)0.003 (2)0.023 (2)0.004 (2)
Cl140.0543 (5)0.0973 (9)0.0790 (7)0.0005 (6)0.0389 (5)0.0129 (7)
Cl150.0680 (7)0.0587 (7)0.122 (1)0.0224 (6)0.0377 (7)0.0266 (7)
O160.045 (1)0.078 (2)0.045 (1)0.001 (1)0.016 (1)0.011 (1)
C170.062 (3)0.088 (3)0.054 (2)0.005 (2)0.021 (2)0.012 (2)
C180.056 (2)0.068 (3)0.044 (2)0.000 (2)0.024 (2)0.007 (2)
C190.072 (3)0.061 (3)0.057 (2)0.018 (2)0.027 (2)0.008 (2)
C200.083 (3)0.066 (3)0.057 (2)0.002 (3)0.027 (2)0.005 (2)
C210.059 (2)0.062 (3)0.051 (2)0.001 (2)0.011 (2)0.010 (2)
C220.061 (3)0.061 (3)0.061 (3)0.008 (2)0.026 (2)0.014 (2)
C230.072 (3)0.052 (2)0.055 (2)0.003 (2)0.031 (2)0.003 (2)
Cl240.104 (1)0.091 (1)0.107 (1)0.0485 (9)0.0324 (8)0.0100 (8)
Cl250.0864 (8)0.098 (1)0.0809 (8)0.0125 (8)0.0090 (7)0.0155 (8)
N260.039 (2)0.070 (3)0.048 (2)0.004 (2)0.014 (2)0.001 (2)
O270.060 (2)0.056 (2)0.090 (2)0.005 (2)0.010 (2)0.000 (2)
O280.059 (2)0.137 (3)0.049 (2)0.022 (2)0.009 (1)0.006 (2)
O290.071 (2)0.059 (2)0.076 (2)0.002 (2)0.017 (2)0.009 (2)
N510.051 (2)0.049 (2)0.044 (2)0.003 (2)0.016 (1)0.005 (1)
C520.054 (2)0.086 (3)0.049 (2)0.022 (3)0.019 (2)0.019 (2)
N530.051 (2)0.107 (3)0.056 (2)0.018 (2)0.014 (2)0.005 (2)
C540.071 (3)0.067 (3)0.055 (2)0.015 (3)0.020 (2)0.005 (2)
C550.055 (2)0.056 (3)0.045 (2)0.003 (2)0.011 (2)0.000 (2)
C560.074 (3)0.043 (2)0.054 (2)0.004 (2)0.030 (2)0.008 (2)
C570.061 (2)0.042 (2)0.049 (2)0.003 (2)0.020 (2)0.002 (2)
C580.054 (2)0.043 (2)0.041 (2)0.003 (2)0.015 (2)0.005 (2)
C590.058 (2)0.058 (3)0.043 (2)0.009 (2)0.010 (2)0.003 (2)
C600.052 (2)0.059 (3)0.057 (2)0.007 (2)0.014 (2)0.008 (2)
C610.061 (2)0.048 (2)0.071 (3)0.001 (2)0.029 (2)0.000 (2)
C620.069 (3)0.049 (2)0.059 (2)0.008 (2)0.020 (2)0.017 (2)
C630.051 (2)0.054 (2)0.045 (2)0.004 (2)0.009 (2)0.002 (2)
Cl640.0855 (8)0.109 (1)0.0658 (7)0.0046 (8)0.0089 (6)0.0328 (7)
Cl650.0869 (8)0.0570 (7)0.135 (1)0.0124 (7)0.0391 (8)0.0156 (8)
C670.072 (3)0.055 (3)0.072 (3)0.010 (2)0.043 (2)0.018 (2)
O660.063 (2)0.051 (2)0.061 (2)0.005 (1)0.025 (1)0.015 (1)
C680.057 (2)0.042 (2)0.056 (2)0.002 (2)0.027 (2)0.001 (2)
C690.054 (2)0.044 (2)0.057 (2)0.001 (2)0.027 (2)0.005 (2)
C700.064 (2)0.044 (2)0.055 (2)0.005 (2)0.023 (2)0.001 (2)
C710.057 (2)0.039 (2)0.064 (2)0.002 (2)0.011 (2)0.001 (2)
C720.069 (3)0.053 (3)0.083 (3)0.011 (2)0.038 (2)0.003 (2)
C730.077 (3)0.054 (2)0.070 (3)0.014 (2)0.042 (2)0.019 (2)
Cl740.0754 (7)0.0831 (8)0.0802 (7)0.0142 (7)0.0476 (6)0.0106 (6)
Cl750.0829 (8)0.0547 (6)0.1007 (9)0.0142 (6)0.0151 (7)0.0178 (6)
N760.061 (2)0.050 (2)0.053 (2)0.004 (2)0.014 (2)0.001 (2)
O770.083 (2)0.054 (2)0.104 (2)0.002 (2)0.003 (2)0.003 (2)
O780.095 (3)0.067 (2)0.136 (3)0.010 (2)0.012 (2)0.026 (2)
O790.097 (2)0.101 (3)0.057 (2)0.012 (2)0.010 (2)0.000 (2)
Geometric parameters (Å, º) top
N1—C21.334 (4)N51—C521.343 (5)
N1—C51.367 (5)N51—C551.364 (5)
N1—C61.470 (5)N51—C561.454 (5)
C2—H20.930C52—H520.930
C2—N31.307 (6)C52—N531.302 (7)
N3—H30.860N53—H530.860
N3—C41.365 (5)N53—C541.344 (6)
C4—H40.930C54—H540.930
C4—C51.342 (6)C54—C551.336 (6)
C5—H50.930C55—H550.930
C6—H6A0.970C56—H56A0.970
C6—H6B0.970C56—H56B0.970
C6—C71.524 (6)C56—C571.527 (7)
C7—H70.980C57—H570.980
C7—C81.509 (5)C57—C581.522 (6)
C7—O161.418 (4)C57—O661.421 (4)
C8—C91.400 (5)C58—C591.384 (5)
C8—C131.396 (6)C58—C631.388 (5)
C9—C101.389 (5)C59—C601.375 (6)
C9—Cl141.740 (4)C59—Cl641.739 (4)
C10—H100.930C60—H600.930
C10—C111.374 (6)C60—C611.367 (6)
C11—C121.376 (6)C61—C621.372 (5)
C11—Cl151.727 (4)C61—Cl651.738 (5)
C12—H120.930C62—H620.930
C12—C131.382 (5)C62—C631.372 (6)
C13—H130.930C63—H630.930
O16—C171.432 (6)C67—H67A0.970
C17—H17A0.970C67—H67B0.970
C17—H17B0.970C67—O661.420 (6)
C17—C181.503 (5)C67—C681.499 (5)
C18—C191.375 (6)C68—C691.377 (6)
C18—C231.387 (6)C68—C731.397 (7)
C19—C201.384 (5)C69—C701.383 (5)
C19—Cl241.736 (5)C69—Cl741.745 (5)
C20—H200.930C70—H700.930
C20—C211.377 (6)C70—C711.364 (6)
C21—C221.368 (6)C71—C721.370 (7)
C21—Cl251.751 (4)C71—Cl751.738 (4)
C22—H220.930C72—H720.930
C22—C231.381 (5)C72—C731.382 (6)
C23—H230.930C73—H730.930
N26—O271.229 (5)N76—O771.241 (5)
N26—O281.233 (4)N76—O781.227 (5)
N26—O291.261 (5)N76—O791.216 (4)
C2—N1—C5107.8 (3)C52—N51—C55105.9 (3)
C2—N1—C6126.1 (3)C52—N51—C56128.6 (3)
C5—N1—C6126.1 (3)C55—N51—C56125.2 (3)
N1—C2—H2125.8N51—C52—H52125.6
N1—C2—N3108.5 (4)N51—C52—N53108.9 (4)
H2—C2—N3125.8H52—C52—N53125.6
C2—N3—H3125.2C52—N53—H53124.9
C2—N3—C4109.6 (4)C52—N53—C54110.1 (4)
H3—N3—C4125.2H53—N53—C54124.9
N3—C4—H4126.8N53—C54—H54127.0
N3—C4—C5106.3 (4)N53—C54—C55106.0 (4)
H4—C4—C5126.9H54—C54—C55127.0
N1—C5—C4107.8 (4)N51—C55—C54109.0 (4)
N1—C5—H5126.1N51—C55—H55125.5
C4—C5—H5126.1C54—C55—H55125.5
N1—C6—H6A109.1N51—C56—H56A109.0
N1—C6—H6B109.1N51—C56—H56B109.0
N1—C6—C7112.6 (3)N51—C56—C57112.9 (3)
H6A—C6—H6B107.8H56A—C56—H56B107.8
H6A—C6—C7109.1H56A—C56—C57109.0
H6B—C6—C7109.1H56B—C56—C57109.0
C6—C7—H7109.4C56—C57—H57108.7
C6—C7—C8110.6 (3)C56—C57—C58112.3 (3)
C6—C7—O16104.4 (3)C56—C57—O66105.9 (3)
H7—C7—C8109.4H57—C57—C58108.7
H7—C7—O16109.4H57—C57—O66108.7
C8—C7—O16113.5 (3)C58—C57—O66112.6 (3)
C7—C8—C9123.7 (3)C57—C58—C59122.4 (4)
C7—C8—C13120.5 (3)C57—C58—C63120.6 (3)
C9—C8—C13115.8 (4)C59—C58—C63116.9 (3)
C8—C9—C10122.6 (3)C58—C59—C60122.7 (4)
C8—C9—Cl14120.7 (3)C58—C59—Cl64120.3 (3)
C10—C9—Cl14116.8 (3)C60—C59—Cl64117.0 (3)
C9—C10—H10120.5C59—C60—H60121.0
C9—C10—C11119.0 (3)C59—C60—C61118.1 (4)
H10—C10—C11120.5H60—C60—C61121.0
C10—C11—C12120.4 (4)C60—C61—C62121.7 (4)
C10—C11—Cl15119.4 (3)C60—C61—Cl65118.5 (3)
C12—C11—Cl15120.2 (3)C62—C61—Cl65119.8 (3)
C11—C12—H12120.2C61—C62—H62120.5
C11—C12—C13119.6 (4)C61—C62—C63119.1 (4)
H12—C12—C13120.2H62—C62—C63120.5
C8—C13—C12122.4 (4)C58—C63—C62121.6 (4)
C8—C13—H13118.8C58—C63—H63119.2
C12—C13—H13118.8C62—C63—H63119.2
C7—O16—C17115.6 (3)H67A—C67—H67B108.2
O16—C17—H17A110.4H67A—C67—O66109.8
O16—C17—H17B110.4H67A—C67—C68109.8
O16—C17—C18106.8 (3)H67B—C67—O66109.8
H17A—C17—H17B108.6H67B—C67—C68109.8
H17A—C17—C18110.4O66—C67—C68109.6 (3)
H17B—C17—C18110.4C57—O66—C67113.6 (3)
C17—C18—C19121.8 (4)C67—C68—C69121.9 (3)
C17—C18—C23120.2 (4)C67—C68—C73121.5 (4)
C19—C18—C23117.9 (4)C69—C68—C73116.6 (4)
C18—C19—C20122.1 (4)C68—C69—C70122.9 (3)
C18—C19—Cl24120.2 (3)C68—C69—Cl74119.6 (3)
C20—C19—Cl24117.8 (3)C70—C69—Cl74117.5 (3)
C19—C20—H20121.0C69—C70—H70120.7
C19—C20—C21117.9 (4)C69—C70—C71118.6 (4)
H20—C20—C21121.0H70—C70—C71120.7
C20—C21—C22122.2 (4)C70—C71—C72121.2 (4)
C20—C21—Cl25118.8 (3)C70—C71—Cl75118.7 (3)
C22—C21—Cl25119.0 (3)C72—C71—Cl75120.1 (3)
C21—C22—H22120.8C71—C72—H72120.3
C21—C22—C23118.4 (4)C71—C72—C73119.3 (4)
H22—C22—C23120.8H72—C72—C73120.3
C18—C23—C22121.6 (4)C68—C73—C72121.4 (4)
C18—C23—H23119.2C68—C73—H73119.3
C22—C23—H23119.2C72—C73—H73119.3
O27—N26—O28120.7 (3)O77—N76—O78117.7 (4)
O27—N26—O29118.6 (4)O77—N76—O79120.8 (4)
O28—N26—O29120.7 (3)O78—N76—O79121.4 (4)
C5—N1—C2—H2179.8C55—N51—C52—H52179.8
C5—N1—C2—N30.2 (5)C55—N51—C52—N530.2 (5)
C6—N1—C2—H22.2C56—N51—C52—H525.8
C6—N1—C2—N3177.8 (4)C56—N51—C52—N53174.2 (4)
C2—N1—C5—C40.5 (5)C52—N51—C55—C540.1 (5)
C2—N1—C5—H5179.4C52—N51—C55—H55179.9
C6—N1—C5—C4177.5 (4)C56—N51—C55—C54174.1 (4)
C6—N1—C5—H52.5C56—N51—C55—H555.9
C2—N1—C6—H6A165.2C52—N51—C56—H56A43.2
C2—N1—C6—H6B47.7C52—N51—C56—H56B160.6
C2—N1—C6—C773.6 (5)C52—N51—C56—C5778.1 (5)
C5—N1—C6—H6A12.5C55—N51—C56—H56A143.9
C5—N1—C6—H6B130.0C55—N51—C56—H56B26.5
C5—N1—C6—C7108.7 (4)C55—N51—C56—C5794.8 (4)
N1—C2—N3—H3179.8N51—C52—N53—H53179.5
N1—C2—N3—C40.2 (5)N51—C52—N53—C540.5 (5)
H2—C2—N3—H30.2H52—C52—N53—H530.5
H2—C2—N3—C4179.8H52—C52—N53—C54179.5
C2—N3—C4—H4179.5C52—N53—C54—H54179.5
C2—N3—C4—C50.5 (5)C52—N53—C54—C550.5 (5)
H3—N3—C4—H40.5H53—N53—C54—H540.5
H3—N3—C4—C5179.5H53—N53—C54—C55179.5
N3—C4—C5—N10.6 (5)N53—C54—C55—N510.4 (5)
N3—C4—C5—H5179.4N53—C54—C55—H55179.6
H4—C4—C5—N1179.4H54—C54—C55—N51179.6
H4—C4—C5—H50.6H54—C54—C55—H550.4
N1—C6—C7—H750.4N51—C56—C57—H57173.1
N1—C6—C7—C8171.0 (3)N51—C56—C57—C5852.9 (4)
N1—C6—C7—O1666.5 (4)N51—C56—C57—O6670.4 (4)
H6A—C6—C7—H770.8H56A—C56—C57—H5765.6
H6A—C6—C7—C849.7H56A—C56—C57—C58174.1
H6A—C6—C7—O16172.2H56A—C56—C57—O6650.9
H6B—C6—C7—H7171.7H56B—C56—C57—H5751.8
H6B—C6—C7—C867.8H56B—C56—C57—C5868.4
H6B—C6—C7—O1654.7H56B—C56—C57—O66168.3
C6—C7—C8—C9127.0 (4)C56—C57—C58—C5988.4 (5)
C6—C7—C8—C1351.1 (5)C56—C57—C58—C6388.4 (4)
H7—C7—C8—C96.5H57—C57—C58—C5931.8
H7—C7—C8—C13171.6H57—C57—C58—C63151.4
O16—C7—C8—C9115.9 (4)O66—C57—C58—C59152.2 (4)
O16—C7—C8—C1365.9 (5)O66—C57—C58—C6331.0 (5)
C6—C7—O16—C17167.0 (3)C56—C57—O66—C67165.4 (3)
H7—C7—O16—C1750.0H57—C57—O66—C6748.8
C8—C7—O16—C1772.5 (4)C58—C57—O66—C6771.6 (4)
C7—C8—C9—C10174.8 (4)C57—C58—C59—C60176.5 (4)
C7—C8—C9—Cl145.6 (5)C57—C58—C59—Cl642.4 (6)
C13—C8—C9—C103.4 (6)C63—C58—C59—C600.4 (6)
C13—C8—C9—Cl14176.2 (3)C63—C58—C59—Cl64179.4 (3)
C7—C8—C13—C12175.0 (4)C57—C58—C63—C62176.5 (4)
C7—C8—C13—H135.0C57—C58—C63—H633.5
C9—C8—C13—C123.3 (6)C59—C58—C63—C620.5 (6)
C9—C8—C13—H13176.8C59—C58—C63—H63179.5
C8—C9—C10—H10179.8C58—C59—C60—H60179.5
C8—C9—C10—C110.2 (6)C58—C59—C60—C610.5 (6)
Cl14—C9—C10—H100.2Cl64—C59—C60—H601.5
Cl14—C9—C10—C11179.8 (3)Cl64—C59—C60—C61178.6 (3)
C9—C10—C11—C124.1 (6)C59—C60—C61—C621.2 (7)
C9—C10—C11—Cl15176.4 (3)C59—C60—C61—Cl65179.9 (3)
H10—C10—C11—C12175.9H60—C60—C61—C62178.8
H10—C10—C11—Cl153.6H60—C60—C61—Cl650.1
C10—C11—C12—H12175.8C60—C61—C62—H62178.9
C10—C11—C12—C134.2 (6)C60—C61—C62—C631.1 (7)
Cl15—C11—C12—H123.8Cl65—C61—C62—H620.3
Cl15—C11—C12—C13176.3 (3)Cl65—C61—C62—C63179.8 (3)
C11—C12—C13—C80.4 (6)C61—C62—C63—C580.2 (6)
C11—C12—C13—H13179.6C61—C62—C63—H63179.8
H12—C12—C13—C8179.6H62—C62—C63—C58179.8
H12—C12—C13—H130.4H62—C62—C63—H630.2
C7—O16—C17—H17A36.2H67A—C67—O66—C5735.4
C7—O16—C17—H17B83.9H67B—C67—O66—C5783.4
C7—O16—C17—C18156.1 (3)C68—C67—O66—C57156.0 (3)
O16—C17—C18—C1979.3 (5)H67A—C67—C68—C6972.9
O16—C17—C18—C2396.4 (4)H67A—C67—C68—C73106.6
H17A—C17—C18—C1940.7H67B—C67—C68—C6945.9
H17A—C17—C18—C23143.6H67B—C67—C68—C73134.6
H17B—C17—C18—C19160.7O66—C67—C68—C69166.5 (4)
H17B—C17—C18—C2323.5O66—C67—C68—C7314.0 (5)
C17—C18—C19—C20175.3 (4)C67—C68—C69—C70179.1 (4)
C17—C18—C19—Cl244.1 (6)C67—C68—C69—Cl740.9 (6)
C23—C18—C19—C200.5 (7)C73—C68—C69—C700.4 (6)
C23—C18—C19—Cl24179.9 (3)C73—C68—C69—Cl74179.6 (3)
C17—C18—C23—C22175.6 (4)C67—C68—C73—C72180.0 (4)
C17—C18—C23—H234.4C67—C68—C73—H730.0
C19—C18—C23—C220.2 (6)C69—C68—C73—C720.5 (6)
C19—C18—C23—H23179.8C69—C68—C73—H73179.5
C18—C19—C20—H20179.3C68—C69—C70—H70179.1
C18—C19—C20—C210.7 (7)C68—C69—C70—C710.9 (6)
Cl24—C19—C20—H200.1Cl74—C69—C70—H700.9
Cl24—C19—C20—C21179.9 (3)Cl74—C69—C70—C71179.1 (3)
C19—C20—C21—C220.5 (7)C69—C70—C71—C720.7 (6)
C19—C20—C21—Cl25178.4 (3)C69—C70—C71—Cl75179.9 (3)
H20—C20—C21—C22179.5H70—C70—C71—C72179.3
H20—C20—C21—Cl251.6H70—C70—C71—Cl750.2
C20—C21—C22—H22179.7C70—C71—C72—H72179.8
C20—C21—C22—C230.3 (7)C70—C71—C72—C730.2 (7)
Cl25—C21—C22—H221.9Cl75—C71—C72—H720.7
Cl25—C21—C22—C23178.1 (3)Cl75—C71—C72—C73179.3 (3)
C21—C22—C23—C180.1 (7)C71—C72—C73—C680.8 (7)
C21—C22—C23—H23179.9C71—C72—C73—H73179.2
H22—C22—C23—C18179.9H72—C72—C73—C68179.2
H22—C22—C23—H230.1H72—C72—C73—H730.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O270.932.353.199 (6)151
C13—H13···O280.932.393.287 (6)162
C52—H52···O780.932.393.213 (7)147
N3—H3···O77i0.861.942.801 (5)174
N3—H3···O78i0.862.452.996 (6)122
C5—H5···O28ii0.932.573.016 (6)110
N53—H53···O27iii0.862.362.962 (5)128
N53—H53···O29iii0.861.972.819 (5)169
C54—H54···O79iv0.932.573.480 (7)166
C54—H54···O77iv0.932.623.291 (6)130
C55—H55···O79v0.932.543.088 (6)118
Symmetry codes: (i) x1, y, z; (ii) x, y1/2, z+1; (iii) x+1, y, z; (iv) x, y+1, z; (v) x+1, y+1/2, z.
 

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