Mercapto-N-phenyl­formimidoyl-1-ethyl-3-(2-morpholinoeth­yl)benzimidazolinium inner salt

Akkurt, M.; Karaca, S.; Küçükbay, H.; Yılmaz, U.; Büyükgüngör, O.

doi:10.1107/S1600536805024852

Mercapto-N-phenylformimidoyl-1-ethyl-3-(2-morpholinoethyl)benzimidazolinium inner salt

M. Akkurt, S. Karaca, H. Küçükbay, U. Yılmaz and O. Büyükgüngör

In the title compound {alternative name: [1-ethyl-3-(2-morpholinoethyl)benzimidazoliumyl](phenylimino)methanethiolate}, C₂₂H₂₆N₄OS, 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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805024852/cf6448sup1.cif Contains datablocks global, 2
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805024852/cf64482sup2.hkl Contains datablock 2

CCDC reference: 283769

checkCIF report

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

Computing details top

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
M_r = 394.54	F(000) = 420
Triclinic, P1	D_x = 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	R_int = 0.000
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.0°, θ_min = 2.5°
ω scans	h = −10→10
Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1968)	k = −11→11
T_min = 0.909, T_max = 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(F_o²) + (0.0925P)²] where P = (F_o² + 2F_c²)/3
3213 reflections	(Δ/σ)_max < 0.001
254 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −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	U_iso*/U_eq
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···H18B^xi	3.040
S1···C7	3.698 (4)	C15···H8B^xii	3.030
S1···C12	3.397 (6)	C15···H22B^vi	3.080
S1···C20ⁱ	3.580 (5)	C16···H2ⁱ	3.080
S1···C7ⁱⁱ	3.636 (5)	C16···H22B^vi	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···C16^viii	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···H7B^viii	2.370
O1···C13^iv	3.363 (7)	H4···S1ⁱⁱⁱ	3.020
O1···H13^iv	2.570	H4···H16^vii	2.390
O1···H19B^v	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···C21^vi	3.367 (6)	H8B···C15^xii	3.030
N4···N2	3.112 (6)	H8B···H15^xii	2.450
N4···O1	2.873 (6)	H8C···C9	3.080
N3···H21A^vi	2.860	H12···S1	3.120
N3···H17B	2.780	H12···C10	2.910
N4···H5ⁱⁱⁱ	2.880	H13···O1^iv	2.570
C1···C5ⁱⁱⁱ	3.338 (7)	H13···H14^x	2.440
C1···C8^vii	3.508 (8)	H14···C13^x	3.060
C3···N1ⁱⁱⁱ	3.439 (7)	H14···H13^x	2.440
C3···C7ⁱⁱⁱ	3.438 (7)	H15···H8B^xii	2.450
C4···C9ⁱⁱⁱ	3.483 (7)	H16···C4^vii	2.810
C4···N1ⁱⁱⁱ	3.262 (7)	H16···H4^vii	2.390
C4···C6ⁱⁱⁱ	3.405 (7)	H17A···C2	2.850
C5···C6ⁱⁱⁱ	3.340 (7)	H17A···C14^viii	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···C8^vii	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···C6^vii	3.581 (8)	H18A···H22B	2.310
C8···C1^vii	3.508 (8)	H18B···H19B	2.340
C9···C4ⁱⁱⁱ	3.483 (7)	H18B···H22A	2.430
C10···C18	3.531 (7)	H18B···C14^xi	3.040
C11···C21^vi	3.488 (6)	H19A···C13^viii	2.960
C12···S1	3.397 (6)	H19A···C17	2.770
C13···O1^iv	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···S1^viii	3.580 (5)	H19B···H22A	2.430
C21···N3^ix	3.367 (6)	H19B···O1^v	2.890
C21···C11^ix	3.488 (6)	H19B···H20A^v	2.510
C2···H17A	2.850	H20A···S1^viii	3.190
C3···H7Aⁱⁱⁱ	3.010	H20A···H19B^v	2.510
C4···H16^vii	2.810	H20B···S1^viii	3.100
C5···H7A	2.880	H20B···H21A	2.370
C7···H5	2.980	H20B···H7Aⁱⁱⁱ	2.550
C9···H18A	3.050	H21A···N3^ix	2.860
C9···H8C	3.080	H21A···H20B	2.370
C10···H7B	2.760	H21A···H5ⁱⁱⁱ	2.580
C10···H12	2.910	H21B···C11^ix	2.970
C10···H18A	2.990	H21B···C12^ix	3.080
C10···H17B	2.800	H22A···H18B	2.430
C11···H21B^vi	2.970	H22A···H19B	2.430
C12···H21B^vi	3.080	H22B···C15^ix	3.080
C13···H14^x	3.060	H22B···C16^ix	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···O1^iv	0.93	2.57	3.363 (7)	144

Symmetry code: (iv) −x+1, −y+1, −z+1.

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Mercapto-N-phenyl­formimidoyl-1-ethyl-3-(2-morpholinoeth­yl)benzimidazolinium inner salt

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Mercapto-N-phenylformimidoyl-1-ethyl-3-(2-morpholinoethyl)benzimidazolinium inner salt