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In the title compound {alternative name: [1-ethyl-3-(2-morpholinoethyl)benzimidazoliumyl](phenylimino)methanethiolate}, C
22H
26N
4OS, the morpholine ring has a chair conformation. The dihedral angle between the benzimidazole ring system and the phenyl ring is 0.5 (2)°. The crystal structure is stabilized by intermolecular C—H
O contacts.
Supporting information
CCDC reference: 283769
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.007 Å
- R factor = 0.074
- wR factor = 0.183
- Data-to-parameter ratio = 12.6
checkCIF/PLATON results
No syntax errors found
Alert level A
REFLT03_ALERT_3_A Reflection count < 85% complete (theta max?)
From the CIF: _diffrn_reflns_theta_max 26.00
From the CIF: _diffrn_reflns_theta_full 26.00
From the CIF: _reflns_number_total 3213
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 3987
Completeness (_total/calc) 80.59%
PLAT022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.81
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.81
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
From the CIF: _diffrn_reflns_theta_max 26.00
From the CIF: _reflns_number_total 3213
From the CIF: _diffrn_reflns_limit_ max hkl 10. 11. 15.
From the CIF: _diffrn_reflns_limit_ min hkl -10. -11. -15.
TEST1: Expected hkl limits for theta max
Calculated maximum hkl 10. 11. 17.
Calculated minimum hkl -10. -11. -17.
3 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
[1-ethyl-3-(2-morpholinoethyl)benzimidazolio](phenylimino)methanethiolate
top
Crystal data top
C22H26N4OS | Z = 2 |
Mr = 394.54 | F(000) = 420 |
Triclinic, P1 | Dx = 1.289 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.9037 (16) Å | Cell parameters from 7037 reflections |
b = 9.1916 (15) Å | θ = 2.5–27.1° |
c = 13.950 (2) Å | µ = 0.18 mm−1 |
α = 105.927 (12)° | T = 100 K |
β = 91.443 (13)° | Plate, colorless |
γ = 110.871 (14)° | 0.54 × 0.36 × 0.11 mm |
V = 1016.2 (3) Å3 | |
Data collection top
Stoe IPDS-II diffractometer | 3213 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1957 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.000 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.5° |
ω scans | h = −10→10 |
Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1968) | k = −11→11 |
Tmin = 0.909, Tmax = 0.980 | l = −15→15 |
4337 measured reflections | |
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)] = 0.074 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.183 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0925P)2] where P = (Fo2 + 2Fc2)/3 |
3213 reflections | (Δ/σ)max < 0.001 |
254 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs 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 | |
S1 | 0.58227 (14) | 0.15510 (12) | 0.20438 (10) | 0.0398 (4) | |
O1 | 0.2951 (4) | 0.8174 (4) | 0.4009 (3) | 0.0493 (11) | |
N1 | 0.7125 (4) | 0.3833 (3) | 0.0430 (3) | 0.0313 (10) | |
N2 | 0.7508 (4) | 0.5684 (4) | 0.1872 (3) | 0.0350 (11) | |
N3 | 0.9120 (4) | 0.3331 (4) | 0.2212 (3) | 0.0368 (11) | |
N4 | 0.5163 (5) | 0.6601 (4) | 0.3321 (3) | 0.0401 (13) | |
C1 | 0.7293 (5) | 0.6373 (4) | 0.1140 (3) | 0.0342 (13) | |
C2 | 0.7273 (6) | 0.7916 (5) | 0.1207 (4) | 0.0452 (18) | |
C3 | 0.6991 (6) | 0.8172 (6) | 0.0295 (4) | 0.0477 (18) | |
C4 | 0.6711 (6) | 0.6994 (6) | −0.0633 (5) | 0.0517 (19) | |
C5 | 0.6744 (5) | 0.5462 (5) | −0.0701 (4) | 0.0398 (14) | |
C6 | 0.7050 (5) | 0.5200 (4) | 0.0202 (3) | 0.0296 (13) | |
C7 | 0.7010 (5) | 0.2300 (5) | −0.0351 (3) | 0.0367 (15) | |
C8 | 0.8676 (7) | 0.2447 (6) | −0.0642 (4) | 0.0527 (17) | |
C9 | 0.7406 (5) | 0.4144 (4) | 0.1401 (3) | 0.0291 (13) | |
C10 | 0.7594 (5) | 0.2993 (4) | 0.1939 (3) | 0.0308 (11) | |
C11 | 0.9562 (5) | 0.2461 (4) | 0.2799 (4) | 0.0340 (13) | |
C12 | 0.9091 (6) | 0.2471 (5) | 0.3732 (4) | 0.0386 (14) | |
C13 | 0.9691 (6) | 0.1738 (5) | 0.4316 (4) | 0.0412 (16) | |
C14 | 1.0771 (6) | 0.1011 (5) | 0.3966 (4) | 0.0416 (15) | |
C15 | 1.1250 (6) | 0.1005 (5) | 0.3035 (4) | 0.0428 (16) | |
C16 | 1.0639 (6) | 0.1728 (5) | 0.2440 (4) | 0.0404 (16) | |
C17 | 0.7882 (5) | 0.6482 (5) | 0.2957 (3) | 0.0377 (13) | |
C18 | 0.6443 (6) | 0.6023 (5) | 0.3525 (4) | 0.0421 (16) | |
C19 | 0.5701 (6) | 0.8378 (5) | 0.3751 (4) | 0.0440 (15) | |
C20 | 0.4345 (6) | 0.8926 (5) | 0.3574 (4) | 0.0437 (16) | |
C21 | 0.2435 (6) | 0.6451 (5) | 0.3607 (4) | 0.0493 (16) | |
C22 | 0.3738 (7) | 0.5841 (5) | 0.3777 (4) | 0.0489 (16) | |
H2 | 0.7438 | 0.8714 | 0.1821 | 0.054* | |
H3 | 0.6989 | 0.9187 | 0.0305 | 0.057* | |
H4 | 0.6499 | 0.7230 | −0.1217 | 0.062* | |
H5 | 0.6571 | 0.4665 | −0.1316 | 0.048* | |
H7A | 0.6279 | 0.2107 | −0.0940 | 0.044* | |
H7B | 0.6575 | 0.1380 | −0.0090 | 0.044* | |
H8A | 0.9070 | 0.3309 | −0.0944 | 0.079* | |
H8B | 0.8604 | 0.1435 | −0.1114 | 0.079* | |
H8C | 0.9409 | 0.2689 | −0.0052 | 0.079* | |
H12 | 0.8372 | 0.2967 | 0.3972 | 0.046* | |
H13 | 0.9364 | 0.1738 | 0.4944 | 0.050* | |
H14 | 1.1173 | 0.0526 | 0.4359 | 0.050* | |
H15 | 1.1981 | 0.0521 | 0.2801 | 0.052* | |
H16 | 1.0954 | 0.1717 | 0.1808 | 0.049* | |
H17A | 0.8309 | 0.7656 | 0.3081 | 0.045* | |
H17B | 0.8727 | 0.6204 | 0.3221 | 0.045* | |
H18A | 0.5970 | 0.4842 | 0.3359 | 0.051* | |
H18B | 0.6833 | 0.6459 | 0.4240 | 0.051* | |
H19A | 0.6621 | 0.8909 | 0.3444 | 0.053* | |
H19B | 0.6044 | 0.8691 | 0.4468 | 0.053* | |
H20A | 0.4720 | 1.0103 | 0.3861 | 0.052* | |
H20B | 0.4043 | 0.8658 | 0.2856 | 0.052* | |
H21A | 0.2089 | 0.6131 | 0.2890 | 0.059* | |
H21B | 0.1508 | 0.5938 | 0.3916 | 0.059* | |
H22A | 0.4044 | 0.6097 | 0.4493 | 0.058* | |
H22B | 0.3331 | 0.4663 | 0.3483 | 0.058* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0408 (6) | 0.0305 (5) | 0.0475 (8) | 0.0089 (4) | 0.0009 (5) | 0.0175 (4) |
O1 | 0.055 (2) | 0.0443 (16) | 0.049 (2) | 0.0210 (16) | 0.0130 (16) | 0.0113 (15) |
N1 | 0.0364 (19) | 0.0242 (15) | 0.034 (2) | 0.0122 (15) | 0.0062 (15) | 0.0090 (13) |
N2 | 0.045 (2) | 0.0239 (15) | 0.036 (2) | 0.0138 (16) | 0.0070 (16) | 0.0078 (14) |
N3 | 0.042 (2) | 0.0323 (16) | 0.040 (2) | 0.0139 (16) | 0.0086 (16) | 0.0171 (15) |
N4 | 0.046 (2) | 0.0273 (16) | 0.041 (3) | 0.0128 (17) | 0.0089 (16) | 0.0022 (15) |
C1 | 0.037 (2) | 0.0277 (18) | 0.039 (3) | 0.0112 (18) | 0.0106 (18) | 0.0126 (17) |
C2 | 0.044 (3) | 0.0264 (18) | 0.072 (4) | 0.0167 (19) | 0.020 (2) | 0.020 (2) |
C3 | 0.049 (3) | 0.040 (2) | 0.072 (4) | 0.024 (2) | 0.022 (2) | 0.034 (2) |
C4 | 0.048 (3) | 0.061 (3) | 0.076 (4) | 0.033 (3) | 0.025 (3) | 0.049 (3) |
C5 | 0.038 (2) | 0.045 (2) | 0.044 (3) | 0.017 (2) | 0.0101 (19) | 0.023 (2) |
C6 | 0.035 (2) | 0.0321 (18) | 0.031 (3) | 0.0164 (17) | 0.0114 (16) | 0.0184 (16) |
C7 | 0.049 (3) | 0.0303 (19) | 0.030 (3) | 0.0190 (19) | 0.0051 (18) | 0.0025 (16) |
C8 | 0.059 (3) | 0.053 (3) | 0.045 (3) | 0.030 (3) | 0.011 (2) | 0.001 (2) |
C9 | 0.035 (2) | 0.0245 (17) | 0.023 (3) | 0.0073 (16) | 0.0012 (15) | 0.0053 (14) |
C10 | 0.040 (2) | 0.0302 (18) | 0.026 (2) | 0.0179 (17) | 0.0094 (17) | 0.0079 (15) |
C11 | 0.032 (2) | 0.0240 (17) | 0.043 (3) | 0.0059 (17) | 0.0006 (18) | 0.0120 (16) |
C12 | 0.043 (2) | 0.038 (2) | 0.037 (3) | 0.016 (2) | 0.0029 (19) | 0.0141 (18) |
C13 | 0.056 (3) | 0.041 (2) | 0.029 (3) | 0.017 (2) | 0.004 (2) | 0.0164 (18) |
C14 | 0.043 (3) | 0.0264 (18) | 0.047 (3) | 0.0053 (19) | −0.011 (2) | 0.0099 (17) |
C15 | 0.047 (3) | 0.037 (2) | 0.046 (3) | 0.020 (2) | 0.003 (2) | 0.0097 (19) |
C16 | 0.043 (3) | 0.040 (2) | 0.041 (3) | 0.016 (2) | 0.0071 (19) | 0.0161 (19) |
C17 | 0.044 (2) | 0.0273 (18) | 0.034 (3) | 0.0117 (18) | 0.0008 (18) | 0.0000 (16) |
C18 | 0.049 (3) | 0.036 (2) | 0.039 (3) | 0.018 (2) | 0.008 (2) | 0.0051 (18) |
C19 | 0.047 (3) | 0.0275 (19) | 0.049 (3) | 0.010 (2) | 0.008 (2) | 0.0037 (18) |
C20 | 0.053 (3) | 0.038 (2) | 0.044 (3) | 0.021 (2) | 0.017 (2) | 0.0124 (19) |
C21 | 0.048 (3) | 0.039 (2) | 0.045 (3) | 0.009 (2) | 0.006 (2) | −0.002 (2) |
C22 | 0.058 (3) | 0.034 (2) | 0.044 (3) | 0.007 (2) | 0.013 (2) | 0.0087 (19) |
Geometric parameters (Å, º) top
S1—C10 | 1.701 (4) | C19—C20 | 1.503 (8) |
O1—C20 | 1.430 (6) | C21—C22 | 1.496 (8) |
O1—C21 | 1.420 (6) | C2—H2 | 0.930 |
N1—C6 | 1.401 (5) | C3—H3 | 0.930 |
N1—C7 | 1.494 (6) | C4—H4 | 0.930 |
N1—C9 | 1.303 (6) | C5—H5 | 0.930 |
N2—C1 | 1.383 (5) | C7—H7A | 0.970 |
N2—C9 | 1.356 (5) | C7—H7B | 0.970 |
N2—C17 | 1.460 (6) | C8—H8A | 0.960 |
N3—C10 | 1.302 (6) | C8—H8B | 0.960 |
N3—C11 | 1.426 (6) | C8—H8C | 0.960 |
N4—C18 | 1.470 (7) | C12—H12 | 0.930 |
N4—C19 | 1.465 (6) | C13—H13 | 0.930 |
N4—C22 | 1.468 (7) | C14—H14 | 0.930 |
C1—C2 | 1.402 (6) | C15—H15 | 0.930 |
C1—C6 | 1.402 (6) | C16—H16 | 0.930 |
C2—C3 | 1.388 (7) | C17—H17A | 0.970 |
C3—C4 | 1.390 (8) | C17—H17B | 0.970 |
C4—C5 | 1.396 (7) | C18—H18A | 0.970 |
C5—C6 | 1.384 (7) | C18—H18B | 0.970 |
C7—C8 | 1.517 (8) | C19—H19A | 0.970 |
C9—C10 | 1.505 (5) | C19—H19B | 0.970 |
C11—C12 | 1.376 (7) | C20—H20A | 0.970 |
C11—C16 | 1.387 (7) | C20—H20B | 0.970 |
C12—C13 | 1.392 (7) | C21—H21A | 0.970 |
C13—C14 | 1.383 (8) | C21—H21B | 0.970 |
C14—C15 | 1.376 (7) | C22—H22A | 0.970 |
C15—C16 | 1.402 (7) | C22—H22B | 0.970 |
C17—C18 | 1.516 (7) | | |
| | | |
S1···N1 | 3.436 (4) | C14···H18Bxi | 3.040 |
S1···C7 | 3.698 (4) | C15···H8Bxii | 3.030 |
S1···C12 | 3.397 (6) | C15···H22Bvi | 3.080 |
S1···C20i | 3.580 (5) | C16···H2i | 3.080 |
S1···C7ii | 3.636 (5) | C16···H22Bvi | 2.860 |
S1···H7B | 3.040 | C17···H2 | 3.030 |
S1···H12 | 3.120 | C17···H19A | 2.770 |
S1···H20Ai | 3.190 | C19···H17A | 2.750 |
S1···H20Bi | 3.100 | H2···C16viii | 3.080 |
S1···H18A | 3.030 | H2···C17 | 3.030 |
S1···H4iii | 3.020 | H2···H17A | 2.460 |
S1···H7Aii | 3.120 | H2···H19A | 2.370 |
O1···N4 | 2.873 (6) | H3···H7Bviii | 2.370 |
O1···C13iv | 3.363 (7) | H4···S1iii | 3.020 |
O1···H13iv | 2.570 | H4···H16vii | 2.390 |
O1···H19Bv | 2.890 | H5···C7 | 2.980 |
N1···S1 | 3.436 (4) | H5···H7A | 2.470 |
N1···N2 | 2.175 (5) | H5···N4iii | 2.880 |
N1···N3 | 3.246 (5) | H5···H21Aiii | 2.580 |
N1···C3iii | 3.439 (7) | H7A···C5 | 2.880 |
N1···C4iii | 3.262 (7) | H7A···H5 | 2.470 |
N2···N1 | 2.175 (5) | H7A···S1ii | 3.120 |
N2···N3 | 3.115 (5) | H7A···C3iii | 3.010 |
N2···N4 | 3.112 (6) | H7A···H20Biii | 2.550 |
N3···N1 | 3.246 (5) | H7B···S1 | 3.040 |
N3···N2 | 3.115 (5) | H7B···C10 | 2.760 |
N3···C17 | 3.371 (6) | H7B···H3i | 2.370 |
N3···C21vi | 3.367 (6) | H8B···C15xii | 3.030 |
N4···N2 | 3.112 (6) | H8B···H15xii | 2.450 |
N4···O1 | 2.873 (6) | H8C···C9 | 3.080 |
N3···H21Avi | 2.860 | H12···S1 | 3.120 |
N3···H17B | 2.780 | H12···C10 | 2.910 |
N4···H5iii | 2.880 | H13···O1iv | 2.570 |
C1···C5iii | 3.338 (7) | H13···H14x | 2.440 |
C1···C8vii | 3.508 (8) | H14···C13x | 3.060 |
C3···N1iii | 3.439 (7) | H14···H13x | 2.440 |
C3···C7iii | 3.438 (7) | H15···H8Bxii | 2.450 |
C4···C9iii | 3.483 (7) | H16···C4vii | 2.810 |
C4···N1iii | 3.262 (7) | H16···H4vii | 2.390 |
C4···C6iii | 3.405 (7) | H17A···C2 | 2.850 |
C5···C6iii | 3.340 (7) | H17A···C14viii | 2.970 |
C5···C1iii | 3.338 (7) | H17A···C19 | 2.750 |
C6···C6iii | 3.550 (7) | H17A···H2 | 2.460 |
C6···C4iii | 3.405 (7) | H17A···H19A | 2.190 |
C6···C8vii | 3.581 (8) | H17B···N3 | 2.780 |
C6···C5iii | 3.340 (7) | H17B···C10 | 2.800 |
C7···S1 | 3.698 (4) | H18A···S1 | 3.030 |
C7···S1ii | 3.636 (5) | H18A···C9 | 3.050 |
C7···C3iii | 3.438 (7) | H18A···C10 | 2.990 |
C8···C6vii | 3.581 (8) | H18A···H22B | 2.310 |
C8···C1vii | 3.508 (8) | H18B···H19B | 2.340 |
C9···C4iii | 3.483 (7) | H18B···H22A | 2.430 |
C10···C18 | 3.531 (7) | H18B···C14xi | 3.040 |
C11···C21vi | 3.488 (6) | H19A···C13viii | 2.960 |
C12···S1 | 3.397 (6) | H19A···C17 | 2.770 |
C13···O1iv | 3.363 (7) | H19A···H2 | 2.370 |
C17···N3 | 3.371 (6) | H19A···H17A | 2.190 |
C18···C10 | 3.531 (7) | H19B···H18B | 2.340 |
C20···S1viii | 3.580 (5) | H19B···H22A | 2.430 |
C21···N3ix | 3.367 (6) | H19B···O1v | 2.890 |
C21···C11ix | 3.488 (6) | H19B···H20Av | 2.510 |
C2···H17A | 2.850 | H20A···S1viii | 3.190 |
C3···H7Aiii | 3.010 | H20A···H19Bv | 2.510 |
C4···H16vii | 2.810 | H20B···S1viii | 3.100 |
C5···H7A | 2.880 | H20B···H21A | 2.370 |
C7···H5 | 2.980 | H20B···H7Aiii | 2.550 |
C9···H18A | 3.050 | H21A···N3ix | 2.860 |
C9···H8C | 3.080 | H21A···H20B | 2.370 |
C10···H7B | 2.760 | H21A···H5iii | 2.580 |
C10···H12 | 2.910 | H21B···C11ix | 2.970 |
C10···H18A | 2.990 | H21B···C12ix | 3.080 |
C10···H17B | 2.800 | H22A···H18B | 2.430 |
C11···H21Bvi | 2.970 | H22A···H19B | 2.430 |
C12···H21Bvi | 3.080 | H22B···C15ix | 3.080 |
C13···H14x | 3.060 | H22B···C16ix | 2.860 |
C13···H19Ai | 2.960 | H22B···H18A | 2.310 |
C14···H17Ai | 2.970 | | |
| | | |
C20—O1—C21 | 108.9 (4) | N1—C7—H7B | 110.0 |
C6—N1—C7 | 123.5 (4) | C8—C7—H7A | 110.0 |
C6—N1—C9 | 110.2 (3) | C8—C7—H7B | 110.0 |
C7—N1—C9 | 126.2 (3) | H7A—C7—H7B | 108.0 |
C1—N2—C9 | 107.8 (4) | C7—C8—H8A | 110.0 |
C1—N2—C17 | 126.9 (4) | C7—C8—H8B | 109.0 |
C9—N2—C17 | 125.2 (4) | C7—C8—H8C | 109.0 |
C10—N3—C11 | 119.8 (4) | H8A—C8—H8B | 109.0 |
C18—N4—C19 | 111.4 (4) | H8A—C8—H8C | 109.0 |
C18—N4—C22 | 109.3 (4) | H8B—C8—H8C | 109.0 |
C19—N4—C22 | 108.1 (4) | C11—C12—H12 | 120.0 |
N2—C1—C2 | 131.6 (4) | C13—C12—H12 | 120.0 |
N2—C1—C6 | 107.5 (3) | C12—C13—H13 | 120.0 |
C2—C1—C6 | 120.9 (4) | C14—C13—H13 | 120.0 |
C1—C2—C3 | 115.5 (5) | C13—C14—H14 | 120.0 |
C2—C3—C4 | 123.6 (5) | C15—C14—H14 | 120.0 |
C3—C4—C5 | 121.0 (6) | C14—C15—H15 | 120.0 |
C4—C5—C6 | 116.0 (5) | C16—C15—H15 | 120.0 |
N1—C6—C1 | 104.7 (3) | C11—C16—H16 | 120.0 |
N1—C6—C5 | 132.1 (4) | C15—C16—H16 | 120.0 |
C1—C6—C5 | 123.1 (4) | N2—C17—H17A | 109.0 |
N1—C7—C8 | 109.9 (4) | N2—C17—H17B | 109.0 |
N1—C9—N2 | 109.7 (3) | C18—C17—H17A | 109.0 |
N1—C9—C10 | 126.2 (3) | C18—C17—H17B | 109.0 |
N2—C9—C10 | 124.1 (4) | H17A—C17—H17B | 108.0 |
S1—C10—N3 | 134.3 (3) | N4—C18—H18A | 109.0 |
S1—C10—C9 | 114.9 (3) | N4—C18—H18B | 109.0 |
N3—C10—C9 | 110.8 (4) | C17—C18—H18A | 108.0 |
N3—C11—C12 | 122.4 (4) | C17—C18—H18B | 108.0 |
N3—C11—C16 | 117.1 (4) | H18A—C18—H18B | 107.0 |
C12—C11—C16 | 120.2 (4) | N4—C19—H19A | 110.0 |
C11—C12—C13 | 120.0 (5) | N4—C19—H19B | 110.0 |
C12—C13—C14 | 120.3 (5) | C20—C19—H19A | 110.0 |
C13—C14—C15 | 119.9 (5) | C20—C19—H19B | 110.0 |
C14—C15—C16 | 120.1 (5) | H19A—C19—H19B | 108.0 |
C11—C16—C15 | 119.6 (5) | O1—C20—H20A | 109.0 |
N2—C17—C18 | 114.2 (4) | O1—C20—H20B | 109.0 |
N4—C18—C17 | 115.2 (4) | C19—C20—H20A | 109.0 |
N4—C19—C20 | 110.2 (4) | C19—C20—H20B | 109.0 |
O1—C20—C19 | 112.0 (4) | H20A—C20—H20B | 108.0 |
O1—C21—C22 | 112.7 (4) | O1—C21—H21A | 109.0 |
N4—C22—C21 | 110.3 (4) | O1—C21—H21B | 109.0 |
C1—C2—H2 | 122.0 | C22—C21—H21A | 109.0 |
C3—C2—H2 | 122.0 | C22—C21—H21B | 109.0 |
C2—C3—H3 | 118.0 | H21A—C21—H21B | 108.0 |
C4—C3—H3 | 118.0 | N4—C22—H22A | 110.0 |
C3—C4—H4 | 120.0 | N4—C22—H22B | 110.0 |
C5—C4—H4 | 120.0 | C21—C22—H22A | 110.0 |
C4—C5—H5 | 122.0 | C21—C22—H22B | 110.0 |
C6—C5—H5 | 122.0 | H22A—C22—H22B | 108.0 |
N1—C7—H7A | 110.0 | | |
| | | |
C21—O1—C20—C19 | −57.2 (5) | C18—N4—C22—C21 | 178.2 (4) |
C20—O1—C21—C22 | 57.2 (5) | C18—N4—C19—C20 | −177.3 (4) |
C6—N1—C9—N2 | 1.0 (5) | C19—N4—C18—C17 | −70.4 (5) |
C7—N1—C6—C1 | −176.9 (4) | N2—C1—C6—C5 | 178.0 (4) |
C9—N1—C7—C8 | −88.9 (5) | C2—C1—C6—C5 | −1.5 (7) |
C7—N1—C9—C10 | −3.1 (7) | C2—C1—C6—N1 | −179.1 (4) |
C7—N1—C6—C5 | 5.8 (8) | N2—C1—C6—N1 | 0.4 (5) |
C9—N1—C6—C5 | −178.1 (5) | C6—C1—C2—C3 | 0.4 (7) |
C6—N1—C7—C8 | 86.5 (5) | N2—C1—C2—C3 | −178.9 (5) |
C9—N1—C6—C1 | −0.8 (5) | C1—C2—C3—C4 | 1.3 (8) |
C6—N1—C9—C10 | −179.1 (4) | C2—C3—C4—C5 | −1.9 (9) |
C7—N1—C9—N2 | 176.9 (4) | C3—C4—C5—C6 | 0.7 (8) |
C9—N2—C1—C2 | 179.5 (5) | C4—C5—C6—C1 | 0.9 (7) |
C17—N2—C9—C10 | 2.8 (7) | C4—C5—C6—N1 | 177.8 (5) |
C17—N2—C9—N1 | −177.2 (4) | N1—C9—C10—N3 | 100.3 (5) |
C1—N2—C9—C10 | 179.3 (4) | N2—C9—C10—S1 | 101.1 (4) |
C1—N2—C17—C18 | 102.9 (5) | N2—C9—C10—N3 | −79.8 (5) |
C9—N2—C1—C6 | 0.2 (5) | N1—C9—C10—S1 | −78.9 (5) |
C9—N2—C17—C18 | −81.3 (5) | N3—C11—C16—C15 | 173.3 (4) |
C17—N2—C1—C6 | 176.6 (4) | C12—C11—C16—C15 | −0.3 (7) |
C1—N2—C9—N1 | −0.7 (5) | N3—C11—C12—C13 | −173.5 (4) |
C17—N2—C1—C2 | −4.1 (8) | C16—C11—C12—C13 | −0.3 (7) |
C10—N3—C11—C12 | −59.8 (6) | C11—C12—C13—C14 | 0.6 (7) |
C11—N3—C10—S1 | −5.7 (7) | C12—C13—C14—C15 | −0.3 (8) |
C10—N3—C11—C16 | 126.8 (5) | C13—C14—C15—C16 | −0.3 (8) |
C11—N3—C10—C9 | 175.4 (4) | C14—C15—C16—C11 | 0.6 (7) |
C22—N4—C19—C20 | −57.3 (5) | N2—C17—C18—N4 | −67.5 (5) |
C19—N4—C22—C21 | 56.9 (5) | N4—C19—C20—O1 | 59.0 (5) |
C22—N4—C18—C17 | 170.3 (4) | O1—C21—C22—N4 | −58.6 (6) |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y, −z; (iii) −x+1, −y+1, −z; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y+2, −z+1; (vi) x+1, y, z; (vii) −x+2, −y+1, −z; (viii) x, y+1, z; (ix) x−1, y, z; (x) −x+2, −y, −z+1; (xi) −x+2, −y+1, −z+1; (xii) −x+2, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···O1iv | 0.93 | 2.57 | 3.363 (7) | 144 |
Symmetry code: (iv) −x+1, −y+1, −z+1. |
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