In the structure of the title compound, C25H29N6O+·Cl-·1.69H2O, the irbesartan cation adopts tautomeric form A. The structure is stabilized by systems of hydrogen bonds forming ribbons along the ac diagonal, interlinked by sets of weaker hydrogen bonds involving the solvent water.
Supporting information
CCDC reference: 622561
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.050
- wR factor = 0.139
- Data-to-parameter ratio = 11.8
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 64.95 Deg.
| Author Response: 'see _publ_section_exptl_refinement'
|
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
Tmin and Tmax reported: 0.703 1.000
Tmin and Tmax expected: 0.569 0.922
RR = 1.139
Please check that your absorption correction is appropriate.
THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590
Calculated sin(theta_max)/wavelength = 0.5876
PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6]..... 64.95 Deg.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.18
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.92
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ?
PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms .. ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.21
PLAT128_ALERT_4_C Non-standard setting of Space group P21/c .... P21/a
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.72 Ratio
PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc.
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 23.00 Perc.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 26.00 Deg.
C301 -C29 -C302 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 15.30 Deg.
H291 -C29 -H293 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 22.40 Deg.
H292 -C29 -H294 1.555 1.555 1.555
Alert level G
ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be
replaced by the scaled T values. Since the ratio of scaled T's
is identical to the ratio of reported T values, the scaling
does not imply a change to the absorption corrections used in
the study.
Ratio of Tmax expected/reported 0.922
Tmax scaled 0.922 Tmin scaled 0.648
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
17 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
7 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
2-Butyl-4-oxo-3-{[2'-(1
H-tetrazol-5-yl)biphenyl-4-yl]methyl}-3-aza-1-
azoniaspiro[4.4]non-1-ene chloride 1.69-hydrate
top
Crystal data top
C25H29N6O+·Cl−·1.69H2O | F(000) = 1052 |
Mr = 495.44 | Dx = 1.294 Mg m−3 |
Monoclinic, P21/a | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2 yab | Cell parameters from 8574 reflections |
a = 8.5557 (3) Å | θ = 5.0–59.0° |
b = 25.0130 (8) Å | µ = 1.63 mm−1 |
c = 12.2675 (4) Å | T = 150 K |
β = 104.415 (3)° | Plate, colourless |
V = 2542.64 (15) Å3 | 0.40 × 0.40 × 0.05 mm |
Z = 4 | |
Data collection top
Oxford Diffraction Xcalibur PX Ultra CCD diffractometer | 4280 independent reflections |
Radiation source: fine-focus sealed tube | 3193 reflections with I > 2σ(I) |
Oxford Diffraction, Enhance ULTRA assembly monochromator | Rint = 0.054 |
ω scans | θmax = 65.0°, θmin = 5.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1986) | h = −9→10 |
Tmin = 0.703, Tmax = 1.000 | k = −28→29 |
25461 measured reflections | l = −14→14 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.139 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0973P)2] where P = (Fo2 + 2Fc2)/3 |
4280 reflections | (Δ/σ)max = 0.001 |
364 parameters | Δρmax = 0.88 e Å−3 |
4 restraints | Δρmin = −0.40 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. |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
N1 | 0.8535 (2) | 0.35795 (7) | 0.81803 (15) | 0.0259 (4) | |
C2 | 0.8237 (3) | 0.40155 (9) | 0.87549 (19) | 0.0302 (5) | |
N3 | 0.8878 (2) | 0.39607 (8) | 0.98230 (17) | 0.0301 (5) | |
H3 | 0.891 (3) | 0.4206 (12) | 1.035 (3) | 0.049 (8)* | |
C4 | 0.9711 (3) | 0.34469 (9) | 1.00840 (18) | 0.0277 (5) | |
C5 | 0.9441 (3) | 0.32129 (9) | 0.89173 (19) | 0.0287 (5) | |
O32 | 0.9888 (2) | 0.27833 (7) | 0.86601 (15) | 0.0486 (5) | |
C6 | 0.8974 (3) | 0.30921 (10) | 1.0862 (2) | 0.0366 (6) | |
H61 | 0.8410 | 0.3313 | 1.1315 | 0.044* | |
H62 | 0.8201 | 0.2832 | 1.0417 | 0.044* | |
C7 | 1.0410 (3) | 0.28088 (12) | 1.1610 (2) | 0.0497 (7) | |
H71 | 1.0172 | 0.2689 | 1.2320 | 0.060* | |
H72 | 1.0736 | 0.2496 | 1.1222 | 0.060* | |
C8 | 1.1692 (3) | 0.32351 (14) | 1.1824 (2) | 0.0561 (8) | |
H81 | 1.2779 | 0.3076 | 1.2101 | 0.067* | |
H82 | 1.1510 | 0.3497 | 1.2384 | 0.067* | |
C9 | 1.1522 (3) | 0.34985 (12) | 1.0682 (2) | 0.0419 (6) | |
H91 | 1.2195 | 0.3313 | 1.0249 | 0.050* | |
H92 | 1.1849 | 0.3879 | 1.0770 | 0.050* | |
C10 | 0.8140 (2) | 0.35232 (10) | 0.69518 (18) | 0.0297 (5) | |
H101 | 0.8714 | 0.3208 | 0.6755 | 0.036* | |
H102 | 0.8531 | 0.3843 | 0.6624 | 0.036* | |
C11 | 0.6344 (2) | 0.34589 (9) | 0.64351 (18) | 0.0262 (5) | |
C12 | 0.5652 (2) | 0.37184 (8) | 0.54367 (18) | 0.0247 (5) | |
H121 | 0.6303 | 0.3930 | 0.5081 | 0.030* | |
C13 | 0.4012 (2) | 0.36706 (8) | 0.49525 (18) | 0.0239 (5) | |
H131 | 0.3555 | 0.3842 | 0.4255 | 0.029* | |
C14 | 0.3022 (2) | 0.33742 (8) | 0.54773 (18) | 0.0239 (5) | |
C15 | 0.3731 (3) | 0.31086 (9) | 0.64754 (19) | 0.0295 (5) | |
H151 | 0.3082 | 0.2900 | 0.6838 | 0.035* | |
C16 | 0.5378 (3) | 0.31465 (9) | 0.69440 (19) | 0.0302 (5) | |
H161 | 0.5852 | 0.2958 | 0.7617 | 0.036* | |
C17 | 0.1256 (2) | 0.33361 (8) | 0.49403 (18) | 0.0239 (5) | |
C18 | 0.0356 (2) | 0.37904 (8) | 0.44892 (17) | 0.0226 (5) | |
C19 | −0.1235 (2) | 0.37429 (9) | 0.38648 (18) | 0.0258 (5) | |
H191 | −0.1822 | 0.4052 | 0.3548 | 0.031* | |
C20 | −0.1962 (3) | 0.32447 (9) | 0.3706 (2) | 0.0301 (5) | |
H201 | −0.3044 | 0.3211 | 0.3271 | 0.036* | |
C21 | −0.1120 (3) | 0.27977 (9) | 0.4179 (2) | 0.0303 (5) | |
H211 | −0.1630 | 0.2458 | 0.4084 | 0.036* | |
C22 | 0.0475 (3) | 0.28430 (9) | 0.4794 (2) | 0.0280 (5) | |
H221 | 0.1042 | 0.2532 | 0.5120 | 0.034* | |
C23 | 0.1080 (2) | 0.43286 (8) | 0.46604 (18) | 0.0228 (5) | |
N24 | 0.1821 (2) | 0.45468 (7) | 0.56454 (17) | 0.0253 (4) | |
H24 | 0.191 (3) | 0.4443 (11) | 0.633 (3) | 0.042 (8)* | |
N25 | 0.2349 (2) | 0.50385 (7) | 0.54547 (16) | 0.0297 (4) | |
N26 | 0.1918 (2) | 0.51113 (7) | 0.43691 (17) | 0.0308 (4) | |
N27 | 0.1129 (2) | 0.46733 (7) | 0.38506 (16) | 0.0274 (4) | |
C28 | 0.7231 (4) | 0.44701 (11) | 0.8193 (2) | 0.0575 (8) | |
H281 | 0.7836 | 0.4657 | 0.7715 | 0.069* | |
H282 | 0.6243 | 0.4321 | 0.7685 | 0.069* | |
C29 | 0.6732 (4) | 0.48728 (12) | 0.8917 (3) | 0.0614 (9) | |
H291 | 0.7710 | 0.5084 | 0.9260 | 0.074* | 0.559 (9) |
H292 | 0.6454 | 0.4672 | 0.9539 | 0.074* | 0.559 (9) |
H293 | 0.7685 | 0.5033 | 0.9443 | 0.074* | 0.441 (9) |
H294 | 0.6032 | 0.4710 | 0.9358 | 0.074* | 0.441 (9) |
C301 | 0.5408 (7) | 0.5267 (3) | 0.8518 (7) | 0.054 (2) | 0.559 (9) |
H301 | 0.5404 | 0.5532 | 0.9118 | 0.065* | 0.559 (9) |
H302 | 0.4352 | 0.5082 | 0.8328 | 0.065* | 0.559 (9) |
C311 | 0.5682 (6) | 0.5544 (3) | 0.7500 (5) | 0.0397 (14) | 0.559 (9) |
H311 | 0.6826 | 0.5637 | 0.7627 | 0.060* | 0.559 (9) |
H312 | 0.5029 | 0.5870 | 0.7357 | 0.060* | 0.559 (9) |
H313 | 0.5369 | 0.5305 | 0.6847 | 0.060* | 0.559 (9) |
C302 | 0.5805 (8) | 0.5295 (3) | 0.8106 (7) | 0.043 (3) | 0.441 (9) |
H303 | 0.6581 | 0.5498 | 0.7786 | 0.052* | 0.441 (9) |
H304 | 0.5045 | 0.5112 | 0.7476 | 0.052* | 0.441 (9) |
C312 | 0.4867 (8) | 0.5686 (3) | 0.8636 (7) | 0.054 (2) | 0.441 (9) |
H314 | 0.4553 | 0.5995 | 0.8138 | 0.081* | 0.441 (9) |
H315 | 0.5541 | 0.5806 | 0.9362 | 0.081* | 0.441 (9) |
H316 | 0.3897 | 0.5511 | 0.8752 | 0.081* | 0.441 (9) |
Cl | 0.20416 (7) | 0.41807 (2) | 0.80739 (5) | 0.0393 (2) | |
O33 | −0.0764 (3) | 0.46748 (9) | 0.15423 (18) | 0.0547 (6) | |
H331 | −0.016 (4) | 0.4633 (12) | 0.222 (3) | 0.046 (8)* | |
H332 | −0.112 (4) | 0.4987 (16) | 0.152 (3) | 0.069 (11)* | |
O34 | 0.5064 (4) | 0.34172 (17) | 0.9527 (3) | 0.0576 (15) | 0.686 (11) |
H341 | 0.442 (8) | 0.363 (3) | 0.914 (6) | 0.09 (2)* | 0.686 (11) |
H342 | 0.476 (6) | 0.310 (2) | 0.926 (4) | 0.060 (17)* | 0.686 (11) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0284 (9) | 0.0294 (10) | 0.0190 (9) | −0.0003 (8) | 0.0043 (8) | −0.0014 (8) |
C2 | 0.0383 (12) | 0.0270 (12) | 0.0264 (13) | 0.0024 (10) | 0.0103 (10) | 0.0003 (10) |
N3 | 0.0412 (11) | 0.0258 (10) | 0.0230 (11) | 0.0008 (8) | 0.0073 (9) | −0.0034 (9) |
C4 | 0.0329 (11) | 0.0275 (11) | 0.0218 (11) | 0.0014 (9) | 0.0050 (9) | 0.0007 (10) |
C5 | 0.0314 (11) | 0.0299 (12) | 0.0236 (12) | 0.0022 (10) | 0.0046 (10) | −0.0031 (10) |
O32 | 0.0700 (12) | 0.0363 (10) | 0.0374 (10) | 0.0198 (9) | 0.0096 (9) | −0.0065 (8) |
C6 | 0.0423 (13) | 0.0376 (13) | 0.0318 (13) | 0.0015 (11) | 0.0128 (11) | 0.0079 (11) |
C7 | 0.0606 (17) | 0.0562 (17) | 0.0371 (15) | 0.0228 (14) | 0.0210 (13) | 0.0201 (14) |
C8 | 0.0428 (14) | 0.092 (2) | 0.0283 (14) | 0.0148 (16) | −0.0013 (12) | 0.0066 (16) |
C9 | 0.0320 (12) | 0.0608 (16) | 0.0293 (13) | −0.0013 (12) | 0.0008 (11) | 0.0024 (13) |
C10 | 0.0284 (11) | 0.0423 (13) | 0.0178 (11) | −0.0024 (10) | 0.0049 (9) | −0.0029 (10) |
C11 | 0.0293 (11) | 0.0292 (11) | 0.0204 (11) | −0.0022 (9) | 0.0065 (9) | −0.0051 (9) |
C12 | 0.0276 (11) | 0.0278 (11) | 0.0206 (11) | −0.0021 (9) | 0.0097 (9) | −0.0016 (9) |
C13 | 0.0292 (11) | 0.0231 (10) | 0.0193 (11) | 0.0005 (9) | 0.0058 (9) | −0.0010 (9) |
C14 | 0.0269 (10) | 0.0217 (10) | 0.0235 (11) | −0.0011 (8) | 0.0073 (9) | −0.0024 (9) |
C15 | 0.0330 (11) | 0.0281 (11) | 0.0282 (12) | −0.0039 (9) | 0.0093 (10) | 0.0031 (10) |
C16 | 0.0323 (11) | 0.0334 (12) | 0.0233 (12) | −0.0020 (10) | 0.0038 (10) | 0.0068 (10) |
C17 | 0.0267 (10) | 0.0261 (11) | 0.0203 (11) | −0.0013 (8) | 0.0085 (9) | −0.0012 (9) |
C18 | 0.0280 (10) | 0.0235 (10) | 0.0174 (10) | −0.0028 (8) | 0.0078 (9) | −0.0018 (9) |
C19 | 0.0277 (11) | 0.0272 (11) | 0.0230 (11) | 0.0016 (9) | 0.0075 (9) | −0.0021 (9) |
C20 | 0.0253 (10) | 0.0353 (13) | 0.0304 (13) | −0.0037 (9) | 0.0084 (10) | −0.0063 (10) |
C21 | 0.0326 (11) | 0.0261 (11) | 0.0356 (13) | −0.0092 (9) | 0.0149 (10) | −0.0053 (10) |
C22 | 0.0300 (11) | 0.0255 (11) | 0.0305 (12) | −0.0001 (9) | 0.0114 (10) | 0.0020 (10) |
C23 | 0.0232 (10) | 0.0231 (10) | 0.0218 (11) | 0.0019 (8) | 0.0051 (9) | −0.0004 (9) |
N24 | 0.0299 (9) | 0.0229 (9) | 0.0232 (10) | −0.0025 (7) | 0.0070 (8) | −0.0019 (8) |
N25 | 0.0316 (9) | 0.0230 (9) | 0.0338 (11) | −0.0021 (8) | 0.0071 (9) | −0.0036 (8) |
N26 | 0.0323 (9) | 0.0266 (10) | 0.0323 (11) | −0.0029 (8) | 0.0058 (9) | 0.0002 (9) |
N27 | 0.0296 (9) | 0.0242 (9) | 0.0274 (10) | −0.0016 (8) | 0.0050 (8) | 0.0014 (8) |
C28 | 0.090 (2) | 0.0378 (15) | 0.0390 (16) | 0.0187 (15) | 0.0059 (16) | 0.0064 (13) |
C29 | 0.0631 (18) | 0.0436 (17) | 0.090 (3) | 0.0146 (14) | 0.0422 (18) | 0.0157 (16) |
C301 | 0.037 (4) | 0.066 (5) | 0.069 (5) | 0.009 (3) | 0.032 (3) | −0.004 (3) |
C311 | 0.037 (3) | 0.035 (3) | 0.043 (3) | 0.003 (2) | 0.003 (2) | −0.003 (3) |
C302 | 0.018 (4) | 0.032 (5) | 0.071 (8) | 0.010 (3) | −0.008 (4) | −0.018 (5) |
C312 | 0.042 (3) | 0.037 (4) | 0.082 (6) | 0.012 (3) | 0.011 (3) | −0.005 (3) |
Cl | 0.0541 (4) | 0.0357 (3) | 0.0288 (3) | 0.0018 (3) | 0.0121 (3) | 0.0012 (2) |
O33 | 0.0735 (14) | 0.0464 (12) | 0.0306 (11) | 0.0236 (10) | −0.0126 (10) | −0.0153 (9) |
O34 | 0.054 (2) | 0.067 (3) | 0.047 (2) | 0.0128 (18) | 0.0033 (16) | −0.0005 (18) |
Geometric parameters (Å, º) top
N1—C2 | 1.357 (3) | C18—C23 | 1.475 (3) |
N1—C5 | 1.382 (3) | C19—C20 | 1.385 (3) |
N1—C10 | 1.467 (3) | C19—H191 | 0.9500 |
C2—N3 | 1.296 (3) | C20—C21 | 1.378 (3) |
C2—C28 | 1.488 (3) | C20—H201 | 0.9500 |
N3—C4 | 1.466 (3) | C21—C22 | 1.390 (3) |
N3—H3 | 0.89 (3) | C21—H211 | 0.9500 |
C4—C5 | 1.510 (3) | C22—H221 | 0.9500 |
C4—C9 | 1.545 (3) | C23—N27 | 1.324 (3) |
C4—C6 | 1.548 (3) | C23—N24 | 1.334 (3) |
C5—O32 | 1.209 (3) | N24—N25 | 1.351 (3) |
C6—C7 | 1.514 (4) | N24—H24 | 0.87 (3) |
C6—H61 | 0.9900 | N25—N26 | 1.303 (3) |
C6—H62 | 0.9900 | N26—N27 | 1.359 (3) |
C7—C8 | 1.506 (4) | C28—C29 | 1.475 (4) |
C7—H71 | 0.9900 | C28—H281 | 0.9900 |
C7—H72 | 0.9900 | C28—H282 | 0.9900 |
C8—C9 | 1.522 (4) | C29—C301 | 1.490 (6) |
C8—H81 | 0.9900 | C29—C302 | 1.531 (7) |
C8—H82 | 0.9900 | C29—H291 | 0.9900 |
C9—H91 | 0.9900 | C29—H292 | 0.9900 |
C9—H92 | 0.9900 | C29—H293 | 0.9900 |
C10—C11 | 1.517 (3) | C29—H294 | 0.9900 |
C10—H101 | 0.9900 | C301—C311 | 1.497 (6) |
C10—H102 | 0.9900 | C301—H301 | 0.9900 |
C11—C12 | 1.382 (3) | C301—H302 | 0.9900 |
C11—C16 | 1.393 (3) | C311—H311 | 0.9800 |
C12—C13 | 1.386 (3) | C311—H312 | 0.9800 |
C12—H121 | 0.9500 | C311—H313 | 0.9800 |
C13—C14 | 1.398 (3) | C302—C312 | 1.511 (7) |
C13—H131 | 0.9500 | C302—H303 | 0.9900 |
C14—C15 | 1.393 (3) | C302—H304 | 0.9900 |
C14—C17 | 1.494 (3) | C312—H314 | 0.9800 |
C15—C16 | 1.386 (3) | C312—H315 | 0.9800 |
C15—H151 | 0.9500 | C312—H316 | 0.9800 |
C16—H161 | 0.9500 | O33—H331 | 0.87 (3) |
C17—C22 | 1.393 (3) | O33—H332 | 0.84 (4) |
C17—C18 | 1.406 (3) | O34—H341 | 0.83 (7) |
C18—C19 | 1.391 (3) | O34—H342 | 0.86 (6) |
| | | |
C2—N1—C5 | 109.92 (17) | C19—C18—C23 | 118.36 (18) |
C2—N1—C10 | 125.87 (18) | C17—C18—C23 | 120.82 (18) |
C5—N1—C10 | 123.82 (18) | C20—C19—C18 | 119.9 (2) |
N3—C2—N1 | 110.69 (19) | C20—C19—H191 | 120.1 |
N3—C2—C28 | 126.9 (2) | C18—C19—H191 | 120.1 |
N1—C2—C28 | 122.4 (2) | C21—C20—C19 | 120.11 (19) |
C2—N3—C4 | 112.0 (2) | C21—C20—H201 | 119.9 |
C2—N3—H3 | 126.4 (18) | C19—C20—H201 | 119.9 |
C4—N3—H3 | 121.5 (18) | C20—C21—C22 | 120.2 (2) |
N3—C4—C5 | 100.44 (17) | C20—C21—H211 | 119.9 |
N3—C4—C9 | 113.94 (19) | C22—C21—H211 | 119.9 |
C5—C4—C9 | 112.41 (19) | C21—C22—C17 | 121.1 (2) |
N3—C4—C6 | 112.75 (18) | C21—C22—H221 | 119.4 |
C5—C4—C6 | 111.86 (19) | C17—C22—H221 | 119.4 |
C9—C4—C6 | 105.65 (18) | N27—C23—N24 | 108.47 (18) |
O32—C5—N1 | 125.6 (2) | N27—C23—C18 | 125.32 (19) |
O32—C5—C4 | 127.5 (2) | N24—C23—C18 | 126.20 (19) |
N1—C5—C4 | 106.96 (18) | C23—N24—N25 | 108.65 (19) |
C7—C6—C4 | 104.4 (2) | C23—N24—H24 | 131.6 (19) |
C7—C6—H61 | 110.9 | N25—N24—H24 | 119.3 (19) |
C4—C6—H61 | 110.9 | N26—N25—N24 | 106.40 (17) |
C7—C6—H62 | 110.9 | N25—N26—N27 | 110.30 (17) |
C4—C6—H62 | 110.9 | C23—N27—N26 | 106.18 (17) |
H61—C6—H62 | 108.9 | C29—C28—C2 | 117.6 (2) |
C8—C7—C6 | 102.7 (2) | C29—C28—H281 | 107.9 |
C8—C7—H71 | 111.2 | C2—C28—H281 | 107.9 |
C6—C7—H71 | 111.2 | C29—C28—H282 | 107.9 |
C8—C7—H72 | 111.2 | C2—C28—H282 | 107.9 |
C6—C7—H72 | 111.2 | H281—C28—H282 | 107.2 |
H71—C7—H72 | 109.1 | C28—C29—C301 | 124.4 (4) |
C7—C8—C9 | 104.3 (2) | C28—C29—C302 | 105.1 (4) |
C7—C8—H81 | 110.9 | C301—C29—C302 | 26.0 (3) |
C9—C8—H81 | 110.9 | C28—C29—H291 | 106.2 |
C7—C8—H82 | 110.9 | C301—C29—H291 | 106.2 |
C9—C8—H82 | 110.9 | C302—C29—H291 | 98.9 |
H81—C8—H82 | 108.9 | C28—C29—H292 | 106.2 |
C8—C9—C4 | 104.8 (2) | C301—C29—H292 | 106.2 |
C8—C9—H91 | 110.8 | C302—C29—H292 | 131.7 |
C4—C9—H91 | 110.8 | H291—C29—H292 | 106.4 |
C8—C9—H92 | 110.8 | C28—C29—H293 | 110.7 |
C4—C9—H92 | 110.8 | C301—C29—H293 | 112.4 |
H91—C9—H92 | 108.9 | C302—C29—H293 | 110.7 |
N1—C10—C11 | 112.93 (18) | H291—C29—H293 | 15.3 |
N1—C10—H101 | 109.0 | H292—C29—H293 | 91.1 |
C11—C10—H101 | 109.0 | C28—C29—H294 | 110.7 |
N1—C10—H102 | 109.0 | C301—C29—H294 | 86.5 |
C11—C10—H102 | 109.0 | C302—C29—H294 | 110.7 |
H101—C10—H102 | 107.8 | H291—C29—H294 | 123.3 |
C12—C11—C16 | 119.30 (19) | H292—C29—H294 | 22.4 |
C12—C11—C10 | 119.09 (19) | H293—C29—H294 | 108.8 |
C16—C11—C10 | 121.61 (19) | C29—C301—C311 | 108.4 (4) |
C11—C12—C13 | 120.3 (2) | C29—C301—H301 | 110.0 |
C11—C12—H121 | 119.9 | C311—C301—H301 | 110.0 |
C13—C12—H121 | 119.9 | C29—C301—H302 | 110.0 |
C12—C13—C14 | 120.90 (19) | C311—C301—H302 | 110.0 |
C12—C13—H131 | 119.6 | H301—C301—H302 | 108.4 |
C14—C13—H131 | 119.6 | C312—C302—C29 | 114.3 (7) |
C15—C14—C13 | 118.45 (19) | C312—C302—H303 | 108.7 |
C15—C14—C17 | 121.95 (19) | C29—C302—H303 | 108.7 |
C13—C14—C17 | 119.57 (19) | C312—C302—H304 | 108.7 |
C16—C15—C14 | 120.5 (2) | C29—C302—H304 | 108.7 |
C16—C15—H151 | 119.7 | H303—C302—H304 | 107.6 |
C14—C15—H151 | 119.7 | C302—C312—H314 | 109.5 |
C15—C16—C11 | 120.5 (2) | C302—C312—H315 | 109.5 |
C15—C16—H161 | 119.7 | H314—C312—H315 | 109.5 |
C11—C16—H161 | 119.7 | C302—C312—H316 | 109.5 |
C22—C17—C18 | 117.84 (18) | H314—C312—H316 | 109.5 |
C22—C17—C14 | 120.89 (19) | H315—C312—H316 | 109.5 |
C18—C17—C14 | 121.08 (18) | H331—O33—H332 | 105 (3) |
C19—C18—C17 | 120.82 (19) | H341—O34—H342 | 106 (5) |
| | | |
C5—N1—C2—N3 | −0.3 (3) | C17—C14—C15—C16 | 179.1 (2) |
C10—N1—C2—N3 | −173.38 (19) | C14—C15—C16—C11 | 1.2 (3) |
C5—N1—C2—C28 | −177.5 (2) | C12—C11—C16—C15 | −2.0 (3) |
C10—N1—C2—C28 | 9.4 (4) | C10—C11—C16—C15 | 177.8 (2) |
N1—C2—N3—C4 | −0.5 (3) | C15—C14—C17—C22 | −47.7 (3) |
C28—C2—N3—C4 | 176.6 (3) | C13—C14—C17—C22 | 130.3 (2) |
C2—N3—C4—C5 | 1.0 (2) | C15—C14—C17—C18 | 137.3 (2) |
C2—N3—C4—C9 | 121.4 (2) | C13—C14—C17—C18 | −44.7 (3) |
C2—N3—C4—C6 | −118.2 (2) | C22—C17—C18—C19 | −3.4 (3) |
C2—N1—C5—O32 | 179.4 (2) | C14—C17—C18—C19 | 171.7 (2) |
C10—N1—C5—O32 | −7.3 (3) | C22—C17—C18—C23 | 176.9 (2) |
C2—N1—C5—C4 | 0.9 (2) | C14—C17—C18—C23 | −7.9 (3) |
C10—N1—C5—C4 | 174.18 (18) | C17—C18—C19—C20 | 1.6 (3) |
N3—C4—C5—O32 | −179.6 (2) | C23—C18—C19—C20 | −178.7 (2) |
C9—C4—C5—O32 | 58.9 (3) | C18—C19—C20—C21 | 0.9 (3) |
C6—C4—C5—O32 | −59.7 (3) | C19—C20—C21—C22 | −1.5 (3) |
N3—C4—C5—N1 | −1.1 (2) | C20—C21—C22—C17 | −0.4 (3) |
C9—C4—C5—N1 | −122.6 (2) | C18—C17—C22—C21 | 2.8 (3) |
C6—C4—C5—N1 | 118.7 (2) | C14—C17—C22—C21 | −172.4 (2) |
N3—C4—C6—C7 | −144.1 (2) | C19—C18—C23—N27 | −53.9 (3) |
C5—C4—C6—C7 | 103.5 (2) | C17—C18—C23—N27 | 125.8 (2) |
C9—C4—C6—C7 | −19.1 (3) | C19—C18—C23—N24 | 127.5 (2) |
C4—C6—C7—C8 | 38.0 (3) | C17—C18—C23—N24 | −52.9 (3) |
C6—C7—C8—C9 | −42.9 (3) | N27—C23—N24—N25 | −0.1 (2) |
C7—C8—C9—C4 | 30.6 (3) | C18—C23—N24—N25 | 178.71 (19) |
N3—C4—C9—C8 | 117.4 (2) | C23—N24—N25—N26 | 0.3 (2) |
C5—C4—C9—C8 | −129.2 (2) | N24—N25—N26—N27 | −0.5 (2) |
C6—C4—C9—C8 | −6.9 (3) | N24—C23—N27—N26 | −0.2 (2) |
C2—N1—C10—C11 | −72.2 (3) | C18—C23—N27—N26 | −179.00 (19) |
C5—N1—C10—C11 | 115.6 (2) | N25—N26—N27—C23 | 0.4 (2) |
N1—C10—C11—C12 | 139.7 (2) | N3—C2—C28—C29 | −8.1 (5) |
N1—C10—C11—C16 | −40.1 (3) | N1—C2—C28—C29 | 168.7 (3) |
C16—C11—C12—C13 | 0.4 (3) | C2—C28—C29—C301 | −163.5 (4) |
C10—C11—C12—C13 | −179.4 (2) | C2—C28—C29—C302 | 177.2 (4) |
C11—C12—C13—C14 | 1.9 (3) | C28—C29—C301—C311 | −50.8 (8) |
C12—C13—C14—C15 | −2.7 (3) | C302—C29—C301—C311 | −4.0 (8) |
C12—C13—C14—C17 | 179.25 (19) | C28—C29—C302—C312 | 167.3 (5) |
C13—C14—C15—C16 | 1.1 (3) | C301—C29—C302—C312 | 25.8 (10) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O33i | 0.89 (3) | 1.84 (3) | 2.722 (3) | 172 (3) |
O33—H331···N27 | 0.87 (3) | 2.03 (3) | 2.891 (3) | 170 (3) |
N24—H24···Cl | 0.87 (3) | 2.21 (3) | 3.077 (2) | 178 (3) |
O33—H332···Clii | 0.84 (4) | 2.32 (4) | 3.141 (2) | 166 (3) |
O34—H342···O32iii | 0.86 (6) | 2.35 (6) | 3.177 (5) | 160 (4) |
O34—H341···Cl | 0.83 (7) | 2.53 (7) | 3.349 (4) | 168 (6) |
Symmetry codes: (i) x+1, y, z+1; (ii) −x, −y+1, −z+1; (iii) x−1/2, −y+1/2, z. |