Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807061156/rn2028sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807061156/rn2028Isup2.hkl |
CCDC reference: 673104
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.049
- wR factor = 0.150
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT352_ALERT_3_B Short N-H Bond (0.87A) N1 - H1A ... 0.65 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.79 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.36 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc. PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 17.00 Perc. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 29.90 Deg. C10' -C9 -C10 1.555 1.555 1.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 H2 O PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 4 Br
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C50 H64 Br2 N12 O5 Atom count from _chemical_formula_moiety:C25 H32 Br1 N6 O2.5 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 14 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 5 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 4 ALERT type 3 Indicator that the structure quality may be low 6 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Bartolucci et al. (2007); Goldmann & Stoltefuss (1991).
The title compound was prepared as follows:2-n-Butyl-4-spirocyclopentane -1-[(2'-(triphenyl-methyltetrazol-5-yl)biphenyl-4-yl)methyl]-2-imidazolin-5-one (1.96 g) was dissolved in 10 ml me thanol and 10 ml THF. After the reaction medium had been cooled to 298 K, 4M hydrochloric acid (1.5 ml) was added and the mixture stirred for 3 h at RT and 1 h at 303 K. After evaporation of the solvents, the residue is taken up in water and the pH is brought to 12 by addition of 10M sodium hydroxide solution. The aqueous phase is extracted with ether, toluene and ether, acidified to pH 2 by 1M hydrochloric acid, extracted with ethyl acetate and the extract is dried and evaporated. Then the product powder is dispersed or dissolved in ethanol and mixed with HBr solution, after the addition of water crystals of good quality appeared after a few days.
H atoms were placed in calculated positions and constrained to ride on their parent atoms with distances C–H =0.93–0.98 Å, N–H =0.90 Å and Uiso(H) = 1.2Ueq(C).
Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO (Rigaku/MSC, 2004); data reduction: RAPID-AUTO (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).
Fig. 1. An ORTEP plot of the title compound (I). Displacement ellipsoids are drawn at the 30% probability level. | |
Fig. 2. The packing diagram of (I). |
C25H29N6O+·Br−·1.5H2O | F(000) = 1116 |
Mr = 1072.95 | Dx = 1.350 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.482 (3) Å | Cell parameters from 14089 reflections |
b = 25.285 (5) Å | θ = 3.0–27.5° |
c = 8.6938 (17) Å | µ = 1.59 mm−1 |
β = 105.78 (3)° | T = 293 K |
V = 2640.4 (9) Å3 | Plate, colorless |
Z = 2 | 0.21 × 0.13 × 0.13 mm |
Rigaku R-AXIS RAPID IP area-detector diffractometer | 4907 independent reflections |
Radiation source: rotating anode | 3402 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
oscillation scans | θmax = 25.5°, θmin = 3.0° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −14→15 |
Tmin = 0.727, Tmax = 0.826 | k = −30→30 |
21153 measured reflections | l = −10→9 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0885P)2 + 0.3523P] where P = (Fo2 + 2Fc2)/3 |
4907 reflections | (Δ/σ)max = 0.001 |
355 parameters | Δρmax = 0.81 e Å−3 |
3 restraints | Δρmin = −0.53 e Å−3 |
C25H29N6O+·Br−·1.5H2O | V = 2640.4 (9) Å3 |
Mr = 1072.95 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.482 (3) Å | µ = 1.59 mm−1 |
b = 25.285 (5) Å | T = 293 K |
c = 8.6938 (17) Å | 0.21 × 0.13 × 0.13 mm |
β = 105.78 (3)° |
Rigaku R-AXIS RAPID IP area-detector diffractometer | 4907 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3402 reflections with I > 2σ(I) |
Tmin = 0.727, Tmax = 0.826 | Rint = 0.056 |
21153 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 3 restraints |
wR(F2) = 0.150 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.81 e Å−3 |
4907 reflections | Δρmin = −0.53 e Å−3 |
355 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.0224 (3) | 0.10652 (14) | 0.6152 (4) | 0.0506 (9) | |
N2 | 0.1841 (2) | 0.14371 (11) | 0.6523 (3) | 0.0418 (6) | |
N3 | 0.6216 (2) | 0.03416 (11) | 1.3916 (3) | 0.0445 (7) | |
N4 | 0.5717 (3) | −0.01012 (12) | 1.3141 (4) | 0.0530 (8) | |
N5 | 0.4646 (3) | −0.00437 (11) | 1.2715 (3) | 0.0507 (7) | |
N6 | 0.4445 (2) | 0.04420 (10) | 1.3203 (3) | 0.0408 (6) | |
H6A | 0.371 (3) | 0.0550 (14) | 1.305 (4) | 0.042 (9)* | |
O1 | 0.1343 (3) | 0.22304 (12) | 0.5236 (4) | 0.0809 (9) | |
O1W | −0.1488 (3) | 0.03602 (13) | 0.5792 (5) | 0.0806 (11) | |
HW1A | −0.149 (6) | 0.009 (3) | 0.610 (8) | 0.121* | |
HW1B | −0.215 (5) | 0.042 (2) | 0.516 (7) | 0.121* | |
O2W | 0.0459 (4) | 0.3369 (2) | 0.4848 (6) | 0.0544 (13) | 0.50 |
HW2A | 0.056 (8) | 0.313 (2) | 0.559 (7) | 0.082* | 0.50 |
HW2B | 0.074 (7) | 0.360 (2) | 0.563 (7) | 0.082* | 0.50 |
C1 | −0.0819 (4) | 0.19128 (18) | 0.6060 (5) | 0.0668 (11) | |
H1B | −0.1215 | 0.1697 | 0.6649 | 0.080* | |
H1C | −0.0394 | 0.2179 | 0.6773 | 0.080* | |
C2 | −0.1620 (4) | 0.2167 (2) | 0.4636 (6) | 0.0894 (16) | |
H2A | −0.2324 | 0.2247 | 0.4857 | 0.107* | |
H2B | −0.1312 | 0.2491 | 0.4334 | 0.107* | |
C3 | −0.1763 (4) | 0.1762 (3) | 0.3367 (6) | 0.1002 (19) | |
H3B | −0.2026 | 0.1923 | 0.2320 | 0.120* | |
H3C | −0.2299 | 0.1497 | 0.3480 | 0.120* | |
C4 | −0.0651 (4) | 0.1516 (2) | 0.3560 (5) | 0.0735 (13) | |
H4B | −0.0244 | 0.1700 | 0.2918 | 0.088* | |
H4C | −0.0727 | 0.1147 | 0.3240 | 0.088* | |
C5 | −0.0047 (3) | 0.15675 (14) | 0.5355 (4) | 0.0464 (8) | |
C6 | 0.1091 (3) | 0.18060 (14) | 0.5643 (4) | 0.0486 (9) | |
C7 | 0.1278 (3) | 0.10035 (13) | 0.6782 (4) | 0.0445 (8) | |
C8 | 0.1858 (3) | 0.05499 (18) | 0.7725 (6) | 0.0751 (13) | |
H8A | 0.2271 | 0.0369 | 0.7084 | 0.090* | |
H8B | 0.2400 | 0.0690 | 0.8656 | 0.090* | |
C9 | 0.1196 (5) | 0.0156 (2) | 0.8278 (6) | 0.0840 (15) | |
H9A | 0.0651 | 0.0004 | 0.7372 | 0.101* | |
H9B | 0.0804 | 0.0321 | 0.8973 | 0.101* | |
C10 | 0.1988 (9) | −0.0287 (4) | 0.9208 (13) | 0.071 (3) | 0.636 (14) |
H10A | 0.2286 | −0.0486 | 0.8465 | 0.085* | 0.636 (14) |
H10B | 0.2608 | −0.0125 | 0.9988 | 0.085* | 0.636 (14) |
C10' | 0.1449 (16) | −0.0210 (7) | 0.944 (2) | 0.071 (5) | 0.364 (14) |
H10C | 0.0833 | −0.0454 | 0.9336 | 0.085* | 0.364 (14) |
H10D | 0.1600 | −0.0041 | 1.0484 | 0.085* | 0.364 (14) |
C11 | 0.1412 (8) | −0.0645 (4) | 1.0018 (10) | 0.094 (4) | 0.636 (14) |
H11A | 0.1921 | −0.0910 | 1.0576 | 0.141* | 0.636 (14) |
H11B | 0.0807 | −0.0811 | 0.9247 | 0.141* | 0.636 (14) |
H11C | 0.1126 | −0.0449 | 1.0768 | 0.141* | 0.636 (14) |
C11' | 0.2466 (16) | −0.0499 (6) | 0.9276 (16) | 0.069 (5) | 0.364 (14) |
H11D | 0.2684 | −0.0759 | 1.0107 | 0.103* | 0.364 (14) |
H11E | 0.3062 | −0.0251 | 0.9360 | 0.103* | 0.364 (14) |
H11F | 0.2299 | −0.0670 | 0.8253 | 0.103* | 0.364 (14) |
C12 | 0.3046 (3) | 0.14967 (16) | 0.6926 (4) | 0.0481 (9) | |
H12A | 0.3223 | 0.1807 | 0.6385 | 0.058* | |
H12B | 0.3361 | 0.1191 | 0.6532 | 0.058* | |
C13 | 0.3579 (3) | 0.15515 (13) | 0.8688 (4) | 0.0401 (7) | |
C14 | 0.4569 (3) | 0.12912 (13) | 0.9378 (4) | 0.0407 (7) | |
H14A | 0.4902 | 0.1088 | 0.8744 | 0.049* | |
C15 | 0.5066 (3) | 0.13312 (12) | 1.0994 (4) | 0.0389 (7) | |
H15A | 0.5744 | 0.1164 | 1.1433 | 0.047* | |
C16 | 0.4569 (3) | 0.16183 (12) | 1.1981 (4) | 0.0379 (7) | |
C17 | 0.3577 (3) | 0.18849 (13) | 1.1274 (4) | 0.0444 (8) | |
H17A | 0.3234 | 0.2084 | 1.1906 | 0.053* | |
C18 | 0.3103 (3) | 0.18558 (14) | 0.9653 (4) | 0.0466 (8) | |
H18A | 0.2453 | 0.2043 | 0.9197 | 0.056* | |
C19 | 0.5100 (3) | 0.16517 (12) | 1.3729 (3) | 0.0357 (7) | |
C20 | 0.5238 (3) | 0.21398 (13) | 1.4513 (4) | 0.0461 (8) | |
H20A | 0.4935 | 0.2441 | 1.3947 | 0.055* | |
C21 | 0.5811 (3) | 0.21855 (14) | 1.6101 (4) | 0.0502 (9) | |
H21A | 0.5884 | 0.2514 | 1.6599 | 0.060* | |
C22 | 0.6275 (3) | 0.17448 (15) | 1.6950 (4) | 0.0526 (9) | |
H22A | 0.6679 | 0.1777 | 1.8016 | 0.063* | |
C23 | 0.6142 (3) | 0.12572 (14) | 1.6229 (4) | 0.0455 (8) | |
H23A | 0.6449 | 0.0959 | 1.6813 | 0.055* | |
C24 | 0.5553 (3) | 0.12060 (12) | 1.4634 (4) | 0.0368 (7) | |
C25 | 0.5414 (3) | 0.06719 (12) | 1.3938 (3) | 0.0358 (7) | |
H1A | −0.014 (4) | 0.0882 (16) | 0.613 (5) | 0.047 (14)* | |
Br1 | 0.19252 (3) | 0.083154 (16) | 1.29277 (5) | 0.06089 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0354 (18) | 0.0413 (19) | 0.072 (2) | −0.0086 (15) | 0.0101 (15) | −0.0011 (15) |
N2 | 0.0329 (14) | 0.0439 (16) | 0.0464 (15) | −0.0026 (12) | 0.0070 (11) | −0.0012 (12) |
N3 | 0.0402 (16) | 0.0370 (15) | 0.0542 (16) | 0.0048 (12) | 0.0096 (13) | −0.0015 (12) |
N4 | 0.056 (2) | 0.0385 (17) | 0.0635 (18) | 0.0048 (14) | 0.0142 (15) | −0.0057 (14) |
N5 | 0.059 (2) | 0.0331 (16) | 0.0590 (18) | −0.0020 (13) | 0.0133 (15) | −0.0055 (13) |
N6 | 0.0365 (16) | 0.0325 (15) | 0.0534 (16) | −0.0006 (12) | 0.0126 (13) | −0.0033 (12) |
O1 | 0.067 (2) | 0.0533 (18) | 0.117 (2) | −0.0077 (15) | 0.0161 (18) | 0.0279 (17) |
O1W | 0.0474 (17) | 0.071 (2) | 0.107 (3) | −0.0213 (16) | −0.0074 (16) | 0.0237 (18) |
O2W | 0.047 (3) | 0.055 (3) | 0.050 (3) | 0.009 (2) | −0.007 (2) | −0.014 (2) |
C1 | 0.060 (3) | 0.069 (3) | 0.074 (3) | 0.015 (2) | 0.023 (2) | 0.002 (2) |
C2 | 0.065 (3) | 0.106 (4) | 0.105 (4) | 0.040 (3) | 0.036 (3) | 0.040 (3) |
C3 | 0.058 (3) | 0.142 (5) | 0.085 (3) | 0.018 (3) | −0.007 (3) | 0.018 (4) |
C4 | 0.052 (2) | 0.099 (4) | 0.059 (2) | 0.009 (2) | −0.0013 (19) | −0.004 (2) |
C5 | 0.0358 (18) | 0.047 (2) | 0.0525 (19) | 0.0030 (15) | 0.0061 (15) | 0.0030 (15) |
C6 | 0.042 (2) | 0.046 (2) | 0.056 (2) | −0.0014 (16) | 0.0097 (16) | 0.0057 (16) |
C7 | 0.041 (2) | 0.0366 (18) | 0.055 (2) | −0.0014 (15) | 0.0122 (16) | −0.0017 (15) |
C8 | 0.052 (3) | 0.049 (3) | 0.119 (4) | 0.0085 (19) | 0.015 (3) | 0.024 (2) |
C9 | 0.098 (4) | 0.075 (3) | 0.085 (3) | 0.022 (3) | 0.035 (3) | 0.026 (3) |
C10 | 0.067 (7) | 0.046 (6) | 0.092 (7) | 0.019 (5) | 0.009 (5) | 0.012 (5) |
C10' | 0.081 (12) | 0.062 (10) | 0.077 (9) | 0.028 (9) | 0.037 (9) | 0.010 (7) |
C11 | 0.119 (8) | 0.081 (7) | 0.077 (5) | −0.005 (5) | 0.018 (5) | 0.021 (5) |
C11' | 0.091 (13) | 0.047 (9) | 0.060 (8) | 0.008 (7) | 0.009 (8) | −0.004 (6) |
C12 | 0.0321 (18) | 0.063 (2) | 0.0475 (19) | −0.0043 (16) | 0.0084 (14) | −0.0026 (16) |
C13 | 0.0348 (17) | 0.0400 (18) | 0.0456 (17) | −0.0040 (14) | 0.0109 (14) | −0.0030 (14) |
C14 | 0.0377 (18) | 0.0417 (19) | 0.0459 (18) | −0.0005 (14) | 0.0169 (14) | −0.0043 (14) |
C15 | 0.0321 (17) | 0.0364 (17) | 0.0492 (18) | 0.0038 (13) | 0.0126 (14) | 0.0009 (14) |
C16 | 0.0356 (17) | 0.0295 (16) | 0.0493 (17) | −0.0013 (13) | 0.0130 (14) | −0.0006 (13) |
C17 | 0.0400 (19) | 0.0425 (19) | 0.0518 (19) | 0.0051 (15) | 0.0143 (15) | −0.0056 (15) |
C18 | 0.0331 (17) | 0.049 (2) | 0.055 (2) | 0.0071 (15) | 0.0059 (15) | −0.0008 (16) |
C19 | 0.0354 (17) | 0.0331 (17) | 0.0424 (17) | −0.0008 (13) | 0.0167 (14) | −0.0044 (13) |
C20 | 0.049 (2) | 0.0365 (19) | 0.057 (2) | 0.0043 (15) | 0.0219 (16) | −0.0009 (15) |
C21 | 0.062 (2) | 0.041 (2) | 0.051 (2) | −0.0072 (17) | 0.0224 (17) | −0.0145 (16) |
C22 | 0.064 (2) | 0.052 (2) | 0.0434 (19) | −0.0108 (19) | 0.0172 (17) | −0.0103 (16) |
C23 | 0.049 (2) | 0.044 (2) | 0.0416 (18) | −0.0025 (16) | 0.0085 (15) | 0.0005 (15) |
C24 | 0.0313 (16) | 0.0330 (17) | 0.0481 (18) | −0.0043 (13) | 0.0139 (13) | −0.0052 (14) |
C25 | 0.0357 (17) | 0.0326 (16) | 0.0381 (16) | 0.0005 (13) | 0.0086 (13) | 0.0000 (13) |
Br1 | 0.0465 (3) | 0.0590 (3) | 0.0773 (3) | 0.00469 (18) | 0.0172 (2) | 0.00558 (19) |
N1—C7 | 1.290 (5) | C9—H9B | 0.9700 |
N1—C5 | 1.442 (5) | C10—C11 | 1.452 (15) |
N1—H1A | 0.64 (4) | C10—H10A | 0.9700 |
N2—C7 | 1.354 (4) | C10—H10B | 0.9700 |
N2—C6 | 1.394 (4) | C10'—C11' | 1.51 (2) |
N2—C12 | 1.456 (4) | C10'—H10C | 0.9700 |
N3—C25 | 1.308 (4) | C10'—H10D | 0.9700 |
N3—N4 | 1.366 (4) | C11—H11A | 0.9600 |
N4—N5 | 1.295 (4) | C11—H11B | 0.9600 |
N5—N6 | 1.345 (4) | C11—H11C | 0.9600 |
N6—C25 | 1.337 (4) | C11'—H11D | 0.9600 |
N6—H6A | 0.93 (4) | C11'—H11E | 0.9600 |
O1—C6 | 1.199 (4) | C11'—H11F | 0.9600 |
O1W—HW1A | 0.73 (6) | C12—C13 | 1.501 (4) |
O1W—HW1B | 0.87 (6) | C12—H12A | 0.9700 |
O2W—HW2A | 0.87 (2) | C12—H12B | 0.9700 |
O2W—HW2B | 0.88 (2) | C13—C14 | 1.385 (5) |
C1—C2 | 1.508 (6) | C13—C18 | 1.386 (5) |
C1—C5 | 1.546 (5) | C14—C15 | 1.377 (5) |
C1—H1B | 0.9700 | C14—H14A | 0.9300 |
C1—H1C | 0.9700 | C15—C16 | 1.392 (4) |
C2—C3 | 1.481 (8) | C15—H15A | 0.9300 |
C2—H2A | 0.9700 | C16—C17 | 1.397 (4) |
C2—H2B | 0.9700 | C16—C19 | 1.486 (4) |
C3—C4 | 1.487 (7) | C17—C18 | 1.374 (5) |
C3—H3B | 0.9700 | C17—H17A | 0.9300 |
C3—H3C | 0.9700 | C18—H18A | 0.9300 |
C4—C5 | 1.543 (5) | C19—C20 | 1.397 (4) |
C4—H4B | 0.9700 | C19—C24 | 1.403 (4) |
C4—H4C | 0.9700 | C20—C21 | 1.377 (5) |
C5—C6 | 1.500 (5) | C20—H20A | 0.9300 |
C7—C8 | 1.480 (5) | C21—C22 | 1.375 (5) |
C8—C9 | 1.456 (7) | C21—H21A | 0.9300 |
C8—H8A | 0.9700 | C22—C23 | 1.373 (5) |
C8—H8B | 0.9700 | C22—H22A | 0.9300 |
C9—C10' | 1.345 (17) | C23—C24 | 1.387 (4) |
C9—C10 | 1.565 (10) | C23—H23A | 0.9300 |
C9—H9A | 0.9700 | C24—C25 | 1.471 (4) |
C7—N1—C5 | 112.9 (3) | C9—C10—H10A | 109.3 |
C7—N1—H1A | 123 (4) | C11—C10—H10B | 109.3 |
C5—N1—H1A | 124 (4) | C9—C10—H10B | 109.3 |
C7—N2—C6 | 109.4 (3) | H10A—C10—H10B | 107.9 |
C7—N2—C12 | 126.4 (3) | C9—C10'—C11' | 106.9 (12) |
C6—N2—C12 | 124.0 (3) | C9—C10'—H10C | 110.3 |
C25—N3—N4 | 106.4 (3) | C11'—C10'—H10C | 110.3 |
N5—N4—N3 | 110.2 (3) | C9—C10'—H10D | 110.3 |
N4—N5—N6 | 106.2 (3) | C11'—C10'—H10D | 110.3 |
C25—N6—N5 | 109.0 (3) | H10C—C10'—H10D | 108.6 |
C25—N6—H6A | 132 (2) | C10—C11—H11A | 109.5 |
N5—N6—H6A | 119 (2) | C10—C11—H11B | 109.5 |
HW1A—O1W—HW1B | 107 (6) | H11A—C11—H11B | 109.5 |
HW2A—O2W—HW2B | 87 (2) | C10—C11—H11C | 109.5 |
C2—C1—C5 | 105.1 (3) | H11A—C11—H11C | 109.5 |
C2—C1—H1B | 110.7 | H11B—C11—H11C | 109.5 |
C5—C1—H1B | 110.7 | C10'—C11'—H11D | 109.5 |
C2—C1—H1C | 110.7 | C10'—C11'—H11E | 109.5 |
C5—C1—H1C | 110.7 | H11D—C11'—H11E | 109.5 |
H1B—C1—H1C | 108.8 | C10'—C11'—H11F | 109.5 |
C3—C2—C1 | 103.6 (4) | H11D—C11'—H11F | 109.5 |
C3—C2—H2A | 111.0 | H11E—C11'—H11F | 109.5 |
C1—C2—H2A | 111.0 | N2—C12—C13 | 113.4 (3) |
C3—C2—H2B | 111.0 | N2—C12—H12A | 108.9 |
C1—C2—H2B | 111.0 | C13—C12—H12A | 108.9 |
H2A—C2—H2B | 109.0 | N2—C12—H12B | 108.9 |
C2—C3—C4 | 106.6 (4) | C13—C12—H12B | 108.9 |
C2—C3—H3B | 110.4 | H12A—C12—H12B | 107.7 |
C4—C3—H3B | 110.4 | C14—C13—C18 | 118.8 (3) |
C2—C3—H3C | 110.4 | C14—C13—C12 | 119.6 (3) |
C4—C3—H3C | 110.4 | C18—C13—C12 | 121.7 (3) |
H3B—C3—H3C | 108.6 | C15—C14—C13 | 120.5 (3) |
C3—C4—C5 | 105.3 (4) | C15—C14—H14A | 119.7 |
C3—C4—H4B | 110.7 | C13—C14—H14A | 119.7 |
C5—C4—H4B | 110.7 | C14—C15—C16 | 121.0 (3) |
C3—C4—H4C | 110.7 | C14—C15—H15A | 119.5 |
C5—C4—H4C | 110.7 | C16—C15—H15A | 119.5 |
H4B—C4—H4C | 108.8 | C15—C16—C17 | 118.1 (3) |
N1—C5—C6 | 100.7 (3) | C15—C16—C19 | 120.7 (3) |
N1—C5—C4 | 113.4 (3) | C17—C16—C19 | 121.2 (3) |
C6—C5—C4 | 112.5 (3) | C18—C17—C16 | 120.6 (3) |
N1—C5—C1 | 113.4 (3) | C18—C17—H17A | 119.7 |
C6—C5—C1 | 111.8 (3) | C16—C17—H17A | 119.7 |
C4—C5—C1 | 105.2 (3) | C17—C18—C13 | 121.0 (3) |
O1—C6—N2 | 124.8 (3) | C17—C18—H18A | 119.5 |
O1—C6—C5 | 128.6 (3) | C13—C18—H18A | 119.5 |
N2—C6—C5 | 106.7 (3) | C20—C19—C24 | 117.3 (3) |
N1—C7—N2 | 110.3 (3) | C20—C19—C16 | 120.7 (3) |
N1—C7—C8 | 128.2 (4) | C24—C19—C16 | 121.9 (3) |
N2—C7—C8 | 121.4 (3) | C21—C20—C19 | 121.6 (3) |
C9—C8—C7 | 118.4 (4) | C21—C20—H20A | 119.2 |
C9—C8—H8A | 107.7 | C19—C20—H20A | 119.2 |
C7—C8—H8A | 107.7 | C22—C21—C20 | 119.9 (3) |
C9—C8—H8B | 107.7 | C22—C21—H21A | 120.0 |
C7—C8—H8B | 107.7 | C20—C21—H21A | 120.0 |
H8A—C8—H8B | 107.1 | C23—C22—C21 | 120.1 (3) |
C10'—C9—C8 | 133.0 (10) | C23—C22—H22A | 119.9 |
C10'—C9—C10 | 29.9 (7) | C21—C22—H22A | 119.9 |
C8—C9—C10 | 108.9 (6) | C22—C23—C24 | 120.4 (3) |
C10'—C9—H9A | 107.9 | C22—C23—H23A | 119.8 |
C8—C9—H9A | 109.9 | C24—C23—H23A | 119.8 |
C10—C9—H9A | 109.9 | C23—C24—C19 | 120.6 (3) |
C10'—C9—H9B | 83.1 | C23—C24—C25 | 117.9 (3) |
C8—C9—H9B | 109.9 | C19—C24—C25 | 121.5 (3) |
C10—C9—H9B | 109.9 | N3—C25—N6 | 108.2 (3) |
H9A—C9—H9B | 108.3 | N3—C25—C24 | 125.9 (3) |
C11—C10—C9 | 111.7 (9) | N6—C25—C24 | 125.9 (3) |
C11—C10—H10A | 109.3 | ||
C25—N3—N4—N5 | −0.4 (4) | C10—C9—C10'—C11' | −5.0 (11) |
N3—N4—N5—N6 | 0.6 (4) | C7—N2—C12—C13 | −72.3 (4) |
N4—N5—N6—C25 | −0.5 (4) | C6—N2—C12—C13 | 115.0 (4) |
C5—C1—C2—C3 | 33.1 (5) | N2—C12—C13—C14 | 138.8 (3) |
C1—C2—C3—C4 | −38.6 (6) | N2—C12—C13—C18 | −40.9 (5) |
C2—C3—C4—C5 | 28.4 (6) | C18—C13—C14—C15 | 0.5 (5) |
C7—N1—C5—C6 | −0.2 (4) | C12—C13—C14—C15 | −179.3 (3) |
C7—N1—C5—C4 | 120.3 (4) | C13—C14—C15—C16 | 2.2 (5) |
C7—N1—C5—C1 | −119.7 (4) | C14—C15—C16—C17 | −2.9 (5) |
C3—C4—C5—N1 | 117.3 (4) | C14—C15—C16—C19 | 178.9 (3) |
C3—C4—C5—C6 | −129.1 (4) | C15—C16—C17—C18 | 1.0 (5) |
C3—C4—C5—C1 | −7.2 (5) | C19—C16—C17—C18 | 179.2 (3) |
C2—C1—C5—N1 | −140.4 (4) | C16—C17—C18—C13 | 1.7 (5) |
C2—C1—C5—C6 | 106.5 (4) | C14—C13—C18—C17 | −2.4 (5) |
C2—C1—C5—C4 | −15.9 (5) | C12—C13—C18—C17 | 177.4 (3) |
C7—N2—C6—O1 | 179.7 (4) | C15—C16—C19—C20 | 130.9 (3) |
C12—N2—C6—O1 | −6.6 (6) | C17—C16—C19—C20 | −47.3 (5) |
C7—N2—C6—C5 | 0.4 (4) | C15—C16—C19—C24 | −44.4 (5) |
C12—N2—C6—C5 | 174.2 (3) | C17—C16—C19—C24 | 137.5 (3) |
N1—C5—C6—O1 | −179.4 (4) | C24—C19—C20—C21 | 1.1 (5) |
C4—C5—C6—O1 | 59.5 (6) | C16—C19—C20—C21 | −174.4 (3) |
C1—C5—C6—O1 | −58.6 (5) | C19—C20—C21—C22 | 0.8 (6) |
N1—C5—C6—N2 | −0.2 (4) | C20—C21—C22—C23 | −1.7 (6) |
C4—C5—C6—N2 | −121.3 (3) | C21—C22—C23—C24 | 0.9 (6) |
C1—C5—C6—N2 | 120.6 (3) | C22—C23—C24—C19 | 1.0 (5) |
C5—N1—C7—N2 | 0.4 (4) | C22—C23—C24—C25 | −178.4 (3) |
C5—N1—C7—C8 | 178.1 (4) | C20—C19—C24—C23 | −1.9 (5) |
C6—N2—C7—N1 | −0.5 (4) | C16—C19—C24—C23 | 173.5 (3) |
C12—N2—C7—N1 | −174.1 (3) | C20—C19—C24—C25 | 177.5 (3) |
C6—N2—C7—C8 | −178.4 (4) | C16—C19—C24—C25 | −7.1 (5) |
C12—N2—C7—C8 | 8.0 (5) | N4—N3—C25—N6 | 0.1 (4) |
N1—C7—C8—C9 | −11.7 (7) | N4—N3—C25—C24 | −179.2 (3) |
N2—C7—C8—C9 | 165.7 (4) | N5—N6—C25—N3 | 0.2 (4) |
C7—C8—C9—C10' | −160.0 (11) | N5—N6—C25—C24 | 179.6 (3) |
C7—C8—C9—C10 | 178.8 (6) | C23—C24—C25—N3 | −56.0 (5) |
C10'—C9—C10—C11 | 22.4 (18) | C19—C24—C25—N3 | 124.6 (4) |
C8—C9—C10—C11 | 170.4 (7) | C23—C24—C25—N6 | 124.7 (4) |
C8—C9—C10'—C11' | −48.2 (19) | C19—C24—C25—N6 | −54.7 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N6—H6A···Br1 | 0.93 (4) | 2.31 (4) | 3.241 (3) | 174 (3) |
O1W—HW1A···Br1i | 0.73 (6) | 2.59 (7) | 3.309 (3) | 168 (7) |
O1W—HW1B···N3ii | 0.87 (6) | 2.04 (6) | 2.886 (4) | 163 (6) |
O2W—HW2A···O1 | 0.87 (2) | 2.52 (7) | 3.068 (6) | 122 (7) |
O2W—HW2B···Br1iii | 0.88 (2) | 2.58 (3) | 3.456 (5) | 169 (8) |
N1—H1A···O1W | 0.64 (4) | 2.10 (4) | 2.735 (5) | 171 (5) |
Symmetry codes: (i) −x, −y, −z+2; (ii) x−1, y, z−1; (iii) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C25H29N6O+·Br−·1.5H2O |
Mr | 1072.95 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 12.482 (3), 25.285 (5), 8.6938 (17) |
β (°) | 105.78 (3) |
V (Å3) | 2640.4 (9) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.59 |
Crystal size (mm) | 0.21 × 0.13 × 0.13 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID IP area-detector diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.727, 0.826 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21153, 4907, 3402 |
Rint | 0.056 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.150, 1.04 |
No. of reflections | 4907 |
No. of parameters | 355 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.81, −0.53 |
Computer programs: RAPID-AUTO (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
N6—H6A···Br1 | 0.93 (4) | 2.31 (4) | 3.241 (3) | 174 (3) |
O1W—HW1A···Br1i | 0.73 (6) | 2.59 (7) | 3.309 (3) | 168 (7) |
O1W—HW1B···N3ii | 0.87 (6) | 2.04 (6) | 2.886 (4) | 163 (6) |
O2W—HW2A···O1 | 0.87 (2) | 2.52 (7) | 3.068 (6) | 122 (7) |
O2W—HW2B···Br1iii | 0.88 (2) | 2.58 (3) | 3.456 (5) | 169 (8) |
N1—H1A···O1W | 0.64 (4) | 2.10 (4) | 2.735 (5) | 171 (5) |
Symmetry codes: (i) −x, −y, −z+2; (ii) x−1, y, z−1; (iii) x, −y+1/2, z−1/2. |
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2-n-Butyl-3-((2'-(2H-tetrazol-5-yl)biphenyl-4-yl)methyl)-1,3-diazaspiro(4.4)no n-1-en-4-one is an antihypertensive agent that inhibits the renin-angiotensin system by selectively blocking the AT1 subtype of receptors. The title compound, 2-n-Butyl-3-((2'-(2H-tetrazol-5-yl)biphenyl-4-yl)methyl)-1,3- diazaspiro(4.4)non-1-en-4-one hydrobromide 1.5-hydrate, is an acidic salt hydrate of irbesartan.
In this paper, the single-crystal of the title compound was obtained and the crystal structure was determined. As shown in Fig. 2, the crystal packing is stabilized by a sets of hydrogen bonds between Br-, O1W of the solvent water and N6 in the irbesartan cation. There are also hydrogen bonds between O1W and N1 of the irbesartan cation.
The crystal structure reported is very similar to C25H29N6O+. Cl-.-1.69H2O (Bartolucci et al., 2007) which is the Cl rather than Br salt.