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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807008951/sj2227sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807008951/sj2227Isup2.hkl
Contains datablock I

CCDC reference: 622561

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](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

Computing details top

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'-(1H-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·1.69H2OF(000) = 1052
Mr = 495.44Dx = 1.294 Mg m3
Monoclinic, P21/aCu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2 yabCell parameters from 8574 reflections
a = 8.5557 (3) Åθ = 5.0–59.0°
b = 25.0130 (8) ŵ = 1.63 mm1
c = 12.2675 (4) ÅT = 150 K
β = 104.415 (3)°Plate, colourless
V = 2542.64 (15) Å30.40 × 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 tube3193 reflections with I > 2σ(I)
Oxford Diffraction, Enhance ULTRA assembly monochromatorRint = 0.054
ω scansθmax = 65.0°, θmin = 5.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1986)
h = 910
Tmin = 0.703, Tmax = 1.000k = 2829
25461 measured reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H 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 parametersΔρmax = 0.88 e Å3
4 restraintsΔρmin = 0.40 e Å3
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
xyzUiso*/UeqOcc. (<1)
N10.8535 (2)0.35795 (7)0.81803 (15)0.0259 (4)
C20.8237 (3)0.40155 (9)0.87549 (19)0.0302 (5)
N30.8878 (2)0.39607 (8)0.98230 (17)0.0301 (5)
H30.891 (3)0.4206 (12)1.035 (3)0.049 (8)*
C40.9711 (3)0.34469 (9)1.00840 (18)0.0277 (5)
C50.9441 (3)0.32129 (9)0.89173 (19)0.0287 (5)
O320.9888 (2)0.27833 (7)0.86601 (15)0.0486 (5)
C60.8974 (3)0.30921 (10)1.0862 (2)0.0366 (6)
H610.84100.33131.13150.044*
H620.82010.28321.04170.044*
C71.0410 (3)0.28088 (12)1.1610 (2)0.0497 (7)
H711.01720.26891.23200.060*
H721.07360.24961.12220.060*
C81.1692 (3)0.32351 (14)1.1824 (2)0.0561 (8)
H811.27790.30761.21010.067*
H821.15100.34971.23840.067*
C91.1522 (3)0.34985 (12)1.0682 (2)0.0419 (6)
H911.21950.33131.02490.050*
H921.18490.38791.07700.050*
C100.8140 (2)0.35232 (10)0.69518 (18)0.0297 (5)
H1010.87140.32080.67550.036*
H1020.85310.38430.66240.036*
C110.6344 (2)0.34589 (9)0.64351 (18)0.0262 (5)
C120.5652 (2)0.37184 (8)0.54367 (18)0.0247 (5)
H1210.63030.39300.50810.030*
C130.4012 (2)0.36706 (8)0.49525 (18)0.0239 (5)
H1310.35550.38420.42550.029*
C140.3022 (2)0.33742 (8)0.54773 (18)0.0239 (5)
C150.3731 (3)0.31086 (9)0.64754 (19)0.0295 (5)
H1510.30820.29000.68380.035*
C160.5378 (3)0.31465 (9)0.69440 (19)0.0302 (5)
H1610.58520.29580.76170.036*
C170.1256 (2)0.33361 (8)0.49403 (18)0.0239 (5)
C180.0356 (2)0.37904 (8)0.44892 (17)0.0226 (5)
C190.1235 (2)0.37429 (9)0.38648 (18)0.0258 (5)
H1910.18220.40520.35480.031*
C200.1962 (3)0.32447 (9)0.3706 (2)0.0301 (5)
H2010.30440.32110.32710.036*
C210.1120 (3)0.27977 (9)0.4179 (2)0.0303 (5)
H2110.16300.24580.40840.036*
C220.0475 (3)0.28430 (9)0.4794 (2)0.0280 (5)
H2210.10420.25320.51200.034*
C230.1080 (2)0.43286 (8)0.46604 (18)0.0228 (5)
N240.1821 (2)0.45468 (7)0.56454 (17)0.0253 (4)
H240.191 (3)0.4443 (11)0.633 (3)0.042 (8)*
N250.2349 (2)0.50385 (7)0.54547 (16)0.0297 (4)
N260.1918 (2)0.51113 (7)0.43691 (17)0.0308 (4)
N270.1129 (2)0.46733 (7)0.38506 (16)0.0274 (4)
C280.7231 (4)0.44701 (11)0.8193 (2)0.0575 (8)
H2810.78360.46570.77150.069*
H2820.62430.43210.76850.069*
C290.6732 (4)0.48728 (12)0.8917 (3)0.0614 (9)
H2910.77100.50840.92600.074*0.559 (9)
H2920.64540.46720.95390.074*0.559 (9)
H2930.76850.50330.94430.074*0.441 (9)
H2940.60320.47100.93580.074*0.441 (9)
C3010.5408 (7)0.5267 (3)0.8518 (7)0.054 (2)0.559 (9)
H3010.54040.55320.91180.065*0.559 (9)
H3020.43520.50820.83280.065*0.559 (9)
C3110.5682 (6)0.5544 (3)0.7500 (5)0.0397 (14)0.559 (9)
H3110.68260.56370.76270.060*0.559 (9)
H3120.50290.58700.73570.060*0.559 (9)
H3130.53690.53050.68470.060*0.559 (9)
C3020.5805 (8)0.5295 (3)0.8106 (7)0.043 (3)0.441 (9)
H3030.65810.54980.77860.052*0.441 (9)
H3040.50450.51120.74760.052*0.441 (9)
C3120.4867 (8)0.5686 (3)0.8636 (7)0.054 (2)0.441 (9)
H3140.45530.59950.81380.081*0.441 (9)
H3150.55410.58060.93620.081*0.441 (9)
H3160.38970.55110.87520.081*0.441 (9)
Cl0.20416 (7)0.41807 (2)0.80739 (5)0.0393 (2)
O330.0764 (3)0.46748 (9)0.15423 (18)0.0547 (6)
H3310.016 (4)0.4633 (12)0.222 (3)0.046 (8)*
H3320.112 (4)0.4987 (16)0.152 (3)0.069 (11)*
O340.5064 (4)0.34172 (17)0.9527 (3)0.0576 (15)0.686 (11)
H3410.442 (8)0.363 (3)0.914 (6)0.09 (2)*0.686 (11)
H3420.476 (6)0.310 (2)0.926 (4)0.060 (17)*0.686 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0284 (9)0.0294 (10)0.0190 (9)0.0003 (8)0.0043 (8)0.0014 (8)
C20.0383 (12)0.0270 (12)0.0264 (13)0.0024 (10)0.0103 (10)0.0003 (10)
N30.0412 (11)0.0258 (10)0.0230 (11)0.0008 (8)0.0073 (9)0.0034 (9)
C40.0329 (11)0.0275 (11)0.0218 (11)0.0014 (9)0.0050 (9)0.0007 (10)
C50.0314 (11)0.0299 (12)0.0236 (12)0.0022 (10)0.0046 (10)0.0031 (10)
O320.0700 (12)0.0363 (10)0.0374 (10)0.0198 (9)0.0096 (9)0.0065 (8)
C60.0423 (13)0.0376 (13)0.0318 (13)0.0015 (11)0.0128 (11)0.0079 (11)
C70.0606 (17)0.0562 (17)0.0371 (15)0.0228 (14)0.0210 (13)0.0201 (14)
C80.0428 (14)0.092 (2)0.0283 (14)0.0148 (16)0.0013 (12)0.0066 (16)
C90.0320 (12)0.0608 (16)0.0293 (13)0.0013 (12)0.0008 (11)0.0024 (13)
C100.0284 (11)0.0423 (13)0.0178 (11)0.0024 (10)0.0049 (9)0.0029 (10)
C110.0293 (11)0.0292 (11)0.0204 (11)0.0022 (9)0.0065 (9)0.0051 (9)
C120.0276 (11)0.0278 (11)0.0206 (11)0.0021 (9)0.0097 (9)0.0016 (9)
C130.0292 (11)0.0231 (10)0.0193 (11)0.0005 (9)0.0058 (9)0.0010 (9)
C140.0269 (10)0.0217 (10)0.0235 (11)0.0011 (8)0.0073 (9)0.0024 (9)
C150.0330 (11)0.0281 (11)0.0282 (12)0.0039 (9)0.0093 (10)0.0031 (10)
C160.0323 (11)0.0334 (12)0.0233 (12)0.0020 (10)0.0038 (10)0.0068 (10)
C170.0267 (10)0.0261 (11)0.0203 (11)0.0013 (8)0.0085 (9)0.0012 (9)
C180.0280 (10)0.0235 (10)0.0174 (10)0.0028 (8)0.0078 (9)0.0018 (9)
C190.0277 (11)0.0272 (11)0.0230 (11)0.0016 (9)0.0075 (9)0.0021 (9)
C200.0253 (10)0.0353 (13)0.0304 (13)0.0037 (9)0.0084 (10)0.0063 (10)
C210.0326 (11)0.0261 (11)0.0356 (13)0.0092 (9)0.0149 (10)0.0053 (10)
C220.0300 (11)0.0255 (11)0.0305 (12)0.0001 (9)0.0114 (10)0.0020 (10)
C230.0232 (10)0.0231 (10)0.0218 (11)0.0019 (8)0.0051 (9)0.0004 (9)
N240.0299 (9)0.0229 (9)0.0232 (10)0.0025 (7)0.0070 (8)0.0019 (8)
N250.0316 (9)0.0230 (9)0.0338 (11)0.0021 (8)0.0071 (9)0.0036 (8)
N260.0323 (9)0.0266 (10)0.0323 (11)0.0029 (8)0.0058 (9)0.0002 (9)
N270.0296 (9)0.0242 (9)0.0274 (10)0.0016 (8)0.0050 (8)0.0014 (8)
C280.090 (2)0.0378 (15)0.0390 (16)0.0187 (15)0.0059 (16)0.0064 (13)
C290.0631 (18)0.0436 (17)0.090 (3)0.0146 (14)0.0422 (18)0.0157 (16)
C3010.037 (4)0.066 (5)0.069 (5)0.009 (3)0.032 (3)0.004 (3)
C3110.037 (3)0.035 (3)0.043 (3)0.003 (2)0.003 (2)0.003 (3)
C3020.018 (4)0.032 (5)0.071 (8)0.010 (3)0.008 (4)0.018 (5)
C3120.042 (3)0.037 (4)0.082 (6)0.012 (3)0.011 (3)0.005 (3)
Cl0.0541 (4)0.0357 (3)0.0288 (3)0.0018 (3)0.0121 (3)0.0012 (2)
O330.0735 (14)0.0464 (12)0.0306 (11)0.0236 (10)0.0126 (10)0.0153 (9)
O340.054 (2)0.067 (3)0.047 (2)0.0128 (18)0.0033 (16)0.0005 (18)
Geometric parameters (Å, º) top
N1—C21.357 (3)C18—C231.475 (3)
N1—C51.382 (3)C19—C201.385 (3)
N1—C101.467 (3)C19—H1910.9500
C2—N31.296 (3)C20—C211.378 (3)
C2—C281.488 (3)C20—H2010.9500
N3—C41.466 (3)C21—C221.390 (3)
N3—H30.89 (3)C21—H2110.9500
C4—C51.510 (3)C22—H2210.9500
C4—C91.545 (3)C23—N271.324 (3)
C4—C61.548 (3)C23—N241.334 (3)
C5—O321.209 (3)N24—N251.351 (3)
C6—C71.514 (4)N24—H240.87 (3)
C6—H610.9900N25—N261.303 (3)
C6—H620.9900N26—N271.359 (3)
C7—C81.506 (4)C28—C291.475 (4)
C7—H710.9900C28—H2810.9900
C7—H720.9900C28—H2820.9900
C8—C91.522 (4)C29—C3011.490 (6)
C8—H810.9900C29—C3021.531 (7)
C8—H820.9900C29—H2910.9900
C9—H910.9900C29—H2920.9900
C9—H920.9900C29—H2930.9900
C10—C111.517 (3)C29—H2940.9900
C10—H1010.9900C301—C3111.497 (6)
C10—H1020.9900C301—H3010.9900
C11—C121.382 (3)C301—H3020.9900
C11—C161.393 (3)C311—H3110.9800
C12—C131.386 (3)C311—H3120.9800
C12—H1210.9500C311—H3130.9800
C13—C141.398 (3)C302—C3121.511 (7)
C13—H1310.9500C302—H3030.9900
C14—C151.393 (3)C302—H3040.9900
C14—C171.494 (3)C312—H3140.9800
C15—C161.386 (3)C312—H3150.9800
C15—H1510.9500C312—H3160.9800
C16—H1610.9500O33—H3310.87 (3)
C17—C221.393 (3)O33—H3320.84 (4)
C17—C181.406 (3)O34—H3410.83 (7)
C18—C191.391 (3)O34—H3420.86 (6)
C2—N1—C5109.92 (17)C19—C18—C23118.36 (18)
C2—N1—C10125.87 (18)C17—C18—C23120.82 (18)
C5—N1—C10123.82 (18)C20—C19—C18119.9 (2)
N3—C2—N1110.69 (19)C20—C19—H191120.1
N3—C2—C28126.9 (2)C18—C19—H191120.1
N1—C2—C28122.4 (2)C21—C20—C19120.11 (19)
C2—N3—C4112.0 (2)C21—C20—H201119.9
C2—N3—H3126.4 (18)C19—C20—H201119.9
C4—N3—H3121.5 (18)C20—C21—C22120.2 (2)
N3—C4—C5100.44 (17)C20—C21—H211119.9
N3—C4—C9113.94 (19)C22—C21—H211119.9
C5—C4—C9112.41 (19)C21—C22—C17121.1 (2)
N3—C4—C6112.75 (18)C21—C22—H221119.4
C5—C4—C6111.86 (19)C17—C22—H221119.4
C9—C4—C6105.65 (18)N27—C23—N24108.47 (18)
O32—C5—N1125.6 (2)N27—C23—C18125.32 (19)
O32—C5—C4127.5 (2)N24—C23—C18126.20 (19)
N1—C5—C4106.96 (18)C23—N24—N25108.65 (19)
C7—C6—C4104.4 (2)C23—N24—H24131.6 (19)
C7—C6—H61110.9N25—N24—H24119.3 (19)
C4—C6—H61110.9N26—N25—N24106.40 (17)
C7—C6—H62110.9N25—N26—N27110.30 (17)
C4—C6—H62110.9C23—N27—N26106.18 (17)
H61—C6—H62108.9C29—C28—C2117.6 (2)
C8—C7—C6102.7 (2)C29—C28—H281107.9
C8—C7—H71111.2C2—C28—H281107.9
C6—C7—H71111.2C29—C28—H282107.9
C8—C7—H72111.2C2—C28—H282107.9
C6—C7—H72111.2H281—C28—H282107.2
H71—C7—H72109.1C28—C29—C301124.4 (4)
C7—C8—C9104.3 (2)C28—C29—C302105.1 (4)
C7—C8—H81110.9C301—C29—C30226.0 (3)
C9—C8—H81110.9C28—C29—H291106.2
C7—C8—H82110.9C301—C29—H291106.2
C9—C8—H82110.9C302—C29—H29198.9
H81—C8—H82108.9C28—C29—H292106.2
C8—C9—C4104.8 (2)C301—C29—H292106.2
C8—C9—H91110.8C302—C29—H292131.7
C4—C9—H91110.8H291—C29—H292106.4
C8—C9—H92110.8C28—C29—H293110.7
C4—C9—H92110.8C301—C29—H293112.4
H91—C9—H92108.9C302—C29—H293110.7
N1—C10—C11112.93 (18)H291—C29—H29315.3
N1—C10—H101109.0H292—C29—H29391.1
C11—C10—H101109.0C28—C29—H294110.7
N1—C10—H102109.0C301—C29—H29486.5
C11—C10—H102109.0C302—C29—H294110.7
H101—C10—H102107.8H291—C29—H294123.3
C12—C11—C16119.30 (19)H292—C29—H29422.4
C12—C11—C10119.09 (19)H293—C29—H294108.8
C16—C11—C10121.61 (19)C29—C301—C311108.4 (4)
C11—C12—C13120.3 (2)C29—C301—H301110.0
C11—C12—H121119.9C311—C301—H301110.0
C13—C12—H121119.9C29—C301—H302110.0
C12—C13—C14120.90 (19)C311—C301—H302110.0
C12—C13—H131119.6H301—C301—H302108.4
C14—C13—H131119.6C312—C302—C29114.3 (7)
C15—C14—C13118.45 (19)C312—C302—H303108.7
C15—C14—C17121.95 (19)C29—C302—H303108.7
C13—C14—C17119.57 (19)C312—C302—H304108.7
C16—C15—C14120.5 (2)C29—C302—H304108.7
C16—C15—H151119.7H303—C302—H304107.6
C14—C15—H151119.7C302—C312—H314109.5
C15—C16—C11120.5 (2)C302—C312—H315109.5
C15—C16—H161119.7H314—C312—H315109.5
C11—C16—H161119.7C302—C312—H316109.5
C22—C17—C18117.84 (18)H314—C312—H316109.5
C22—C17—C14120.89 (19)H315—C312—H316109.5
C18—C17—C14121.08 (18)H331—O33—H332105 (3)
C19—C18—C17120.82 (19)H341—O34—H342106 (5)
C5—N1—C2—N30.3 (3)C17—C14—C15—C16179.1 (2)
C10—N1—C2—N3173.38 (19)C14—C15—C16—C111.2 (3)
C5—N1—C2—C28177.5 (2)C12—C11—C16—C152.0 (3)
C10—N1—C2—C289.4 (4)C10—C11—C16—C15177.8 (2)
N1—C2—N3—C40.5 (3)C15—C14—C17—C2247.7 (3)
C28—C2—N3—C4176.6 (3)C13—C14—C17—C22130.3 (2)
C2—N3—C4—C51.0 (2)C15—C14—C17—C18137.3 (2)
C2—N3—C4—C9121.4 (2)C13—C14—C17—C1844.7 (3)
C2—N3—C4—C6118.2 (2)C22—C17—C18—C193.4 (3)
C2—N1—C5—O32179.4 (2)C14—C17—C18—C19171.7 (2)
C10—N1—C5—O327.3 (3)C22—C17—C18—C23176.9 (2)
C2—N1—C5—C40.9 (2)C14—C17—C18—C237.9 (3)
C10—N1—C5—C4174.18 (18)C17—C18—C19—C201.6 (3)
N3—C4—C5—O32179.6 (2)C23—C18—C19—C20178.7 (2)
C9—C4—C5—O3258.9 (3)C18—C19—C20—C210.9 (3)
C6—C4—C5—O3259.7 (3)C19—C20—C21—C221.5 (3)
N3—C4—C5—N11.1 (2)C20—C21—C22—C170.4 (3)
C9—C4—C5—N1122.6 (2)C18—C17—C22—C212.8 (3)
C6—C4—C5—N1118.7 (2)C14—C17—C22—C21172.4 (2)
N3—C4—C6—C7144.1 (2)C19—C18—C23—N2753.9 (3)
C5—C4—C6—C7103.5 (2)C17—C18—C23—N27125.8 (2)
C9—C4—C6—C719.1 (3)C19—C18—C23—N24127.5 (2)
C4—C6—C7—C838.0 (3)C17—C18—C23—N2452.9 (3)
C6—C7—C8—C942.9 (3)N27—C23—N24—N250.1 (2)
C7—C8—C9—C430.6 (3)C18—C23—N24—N25178.71 (19)
N3—C4—C9—C8117.4 (2)C23—N24—N25—N260.3 (2)
C5—C4—C9—C8129.2 (2)N24—N25—N26—N270.5 (2)
C6—C4—C9—C86.9 (3)N24—C23—N27—N260.2 (2)
C2—N1—C10—C1172.2 (3)C18—C23—N27—N26179.00 (19)
C5—N1—C10—C11115.6 (2)N25—N26—N27—C230.4 (2)
N1—C10—C11—C12139.7 (2)N3—C2—C28—C298.1 (5)
N1—C10—C11—C1640.1 (3)N1—C2—C28—C29168.7 (3)
C16—C11—C12—C130.4 (3)C2—C28—C29—C301163.5 (4)
C10—C11—C12—C13179.4 (2)C2—C28—C29—C302177.2 (4)
C11—C12—C13—C141.9 (3)C28—C29—C301—C31150.8 (8)
C12—C13—C14—C152.7 (3)C302—C29—C301—C3114.0 (8)
C12—C13—C14—C17179.25 (19)C28—C29—C302—C312167.3 (5)
C13—C14—C15—C161.1 (3)C301—C29—C302—C31225.8 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O33i0.89 (3)1.84 (3)2.722 (3)172 (3)
O33—H331···N270.87 (3)2.03 (3)2.891 (3)170 (3)
N24—H24···Cl0.87 (3)2.21 (3)3.077 (2)178 (3)
O33—H332···Clii0.84 (4)2.32 (4)3.141 (2)166 (3)
O34—H342···O32iii0.86 (6)2.35 (6)3.177 (5)160 (4)
O34—H341···Cl0.83 (7)2.53 (7)3.349 (4)168 (6)
Symmetry codes: (i) x+1, y, z+1; (ii) x, y+1, z+1; (iii) x1/2, y+1/2, z.
 

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