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The molecular conformation of the title compound {alternative name: [1-methyl-3-(2-phenylethyl)benzimidazolinio](phenylimino)methanethiolate}, C23H21N3S, is non-planar. The mol­ecule includes one benz­imidazole ring system and two phenyl rings. The dihedral angles between the least-squares planes of the two phenyl rings is 85.65 (1)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680401013X/ac6097sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680401013X/ac6097Isup2.hkl
Contains datablock I

CCDC reference: 242301

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.039
  • wR factor = 0.104
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.68 mm PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc. PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C11 -C16 1.37 Ang. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C18 - C23 ... 1.36 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

[1-methyl-3-(2-phenylethyl)benzimidazolinio](phenylimino)methanethiolate top
Crystal data top
C23H21N3SZ = 2
Mr = 371.50F(000) = 392
Triclinic, P1Dx = 1.220 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.3894 (8) ÅCell parameters from 9837 reflections
b = 10.8881 (11) Åθ = 1.9–29.0°
c = 11.6658 (12) ŵ = 0.17 mm1
α = 67.191 (7)°T = 293 K
β = 83.696 (8)°Prism, yellow
γ = 67.040 (7)°0.68 × 0.37 × 0.20 mm
V = 1011.07 (19) Å3
Data collection top
Stoe IPDS-II
diffractometer
3983 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus2562 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.029
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 1.9°
ω scansh = 1111
Absorption correction: integration
STOE X-RED (Stoe & Cie, 2002)
k = 1313
Tmin = 0.923, Tmax = 0.973l = 1414
11523 measured reflections
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 0.94 w = 1/[σ2(Fo2) + (0.0584P)2]
where P = (Fo2 + 2Fc2)/3
3983 reflections(Δ/σ)max < 0.001
279 parametersΔρmax = 0.16 e Å3
91 restraintsΔρmin = 0.26 e Å3
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
xyzUiso*/UeqOcc. (<1)
S10.16304 (6)0.75339 (5)0.01070 (5)0.0731 (2)
N10.31802 (15)0.86503 (14)0.16681 (12)0.0475 (4)
N20.50718 (16)0.69024 (16)0.13306 (15)0.0577 (5)
N30.23520 (18)0.58229 (16)0.23801 (14)0.0619 (5)
C10.4525 (2)0.89101 (18)0.16589 (15)0.0506 (6)
C20.4771 (3)1.0019 (2)0.17980 (18)0.0667 (7)
C30.6263 (3)0.9967 (3)0.16828 (19)0.0801 (9)
C40.7455 (3)0.8868 (3)0.1451 (2)0.0876 (10)
C50.7228 (2)0.7754 (3)0.1325 (2)0.0799 (9)
C60.5718 (2)0.7809 (2)0.14332 (16)0.0573 (6)
C70.5890 (3)0.5601 (3)0.1058 (3)0.0987 (13)
C80.35516 (18)0.74406 (17)0.14606 (15)0.0472 (5)
C90.1626 (2)0.95209 (19)0.18982 (18)0.0616 (6)
C100.1166 (2)0.8865 (2)0.3214 (2)0.0722 (8)
C110.2311 (2)0.8552 (2)0.41913 (18)0.0640 (7)
C120.2235 (3)0.9594 (3)0.4614 (2)0.0853 (9)
C130.3341 (4)0.9320 (3)0.5458 (3)0.1089 (14)
C140.4520 (4)0.8004 (4)0.5894 (3)0.1165 (14)
C150.4609 (4)0.6964 (3)0.5485 (3)0.1047 (10)
C160.3508 (3)0.7242 (2)0.4641 (2)0.0793 (8)
C170.24503 (18)0.68065 (17)0.13472 (17)0.0510 (6)
C180.1416 (2)0.5044 (2)0.24770 (17)0.0633 (7)
C19A0.0926 (8)0.4496 (6)0.3614 (6)0.082 (2)0.600
C20A0.0026 (8)0.3686 (7)0.3838 (7)0.099 (3)0.600
C210.0410 (3)0.3437 (3)0.2889 (3)0.0990 (11)
C220.0370 (3)0.3698 (2)0.1859 (2)0.0789 (9)
C230.1272 (2)0.4505 (2)0.1643 (2)0.0712 (8)
C20B0.0795 (13)0.4404 (11)0.3562 (10)0.099 (4)0.400
C19B0.0149 (12)0.5188 (11)0.3403 (9)0.086 (3)0.400
H30.647601.069600.176400.0960*
H40.844500.888100.137600.1050*
H7A0.697400.542900.100200.1480*
H7B0.548400.572800.028200.1480*
H50.803700.700800.117800.0960*
H20.397001.075800.196100.0800*
H9B0.158201.047500.175200.0740*
H10A0.016400.952100.333600.0870*
H10B0.106100.797700.331800.0870*
H120.142801.049100.432500.1020*
H130.328401.003400.573200.1300*
H140.526200.781600.647100.1390*
H150.541600.606700.577800.1260*
H160.357600.652400.436900.0950*
H19A0.120 (5)0.472 (4)0.426 (4)0.085 (11)*0.600
H20A0.042 (7)0.339 (6)0.470 (6)0.150 (19)*0.600
H210.092700.275900.307800.1190*
H220.031000.333200.127400.0950*
H230.179400.468200.090800.0850*
H7C0.574800.479400.171200.1480*
H9A0.088800.962300.131400.0740*
H19B0.004 (6)0.572 (6)0.391 (5)0.075 (15)*0.400
H20B0.161 (9)0.443 (8)0.421 (8)0.13 (3)*0.400
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0843 (4)0.0718 (3)0.0675 (3)0.0453 (3)0.0237 (3)0.0075 (2)
N10.0420 (7)0.0524 (7)0.0515 (8)0.0228 (6)0.0007 (6)0.0177 (6)
N20.0427 (8)0.0726 (9)0.0717 (10)0.0257 (7)0.0077 (7)0.0386 (8)
N30.0691 (10)0.0696 (9)0.0568 (9)0.0419 (8)0.0038 (7)0.0161 (8)
C10.0532 (10)0.0640 (10)0.0422 (9)0.0346 (9)0.0001 (7)0.0147 (8)
C20.0809 (14)0.0746 (12)0.0612 (11)0.0488 (11)0.0015 (10)0.0225 (9)
C30.1017 (18)0.1085 (17)0.0630 (13)0.0788 (15)0.0021 (12)0.0259 (12)
C40.0734 (15)0.142 (2)0.0767 (15)0.0749 (16)0.0101 (12)0.0382 (15)
C50.0512 (12)0.1231 (18)0.0851 (15)0.0462 (12)0.0112 (10)0.0481 (14)
C60.0485 (10)0.0805 (12)0.0545 (10)0.0347 (9)0.0048 (8)0.0276 (9)
C70.0606 (14)0.1130 (19)0.154 (3)0.0253 (13)0.0196 (15)0.0936 (19)
C80.0430 (9)0.0540 (9)0.0468 (9)0.0221 (8)0.0000 (7)0.0168 (7)
C90.0480 (10)0.0562 (10)0.0784 (13)0.0141 (9)0.0063 (9)0.0263 (9)
C100.0508 (11)0.0836 (13)0.0972 (16)0.0293 (10)0.0206 (11)0.0500 (12)
C110.0639 (12)0.0687 (12)0.0652 (12)0.0306 (10)0.0224 (10)0.0308 (10)
C120.0942 (17)0.0808 (14)0.0862 (16)0.0285 (13)0.0098 (13)0.0429 (13)
C130.144 (3)0.112 (2)0.097 (2)0.057 (2)0.0029 (19)0.0567 (17)
C140.126 (2)0.135 (3)0.0844 (19)0.042 (2)0.0216 (17)0.0378 (18)
C150.113 (2)0.0896 (17)0.0807 (17)0.0152 (15)0.0095 (15)0.0205 (14)
C160.0935 (16)0.0712 (13)0.0693 (14)0.0300 (13)0.0103 (12)0.0254 (11)
C170.0434 (9)0.0538 (9)0.0617 (11)0.0219 (8)0.0010 (8)0.0234 (8)
C180.0730 (12)0.0669 (11)0.0564 (11)0.0418 (10)0.0031 (9)0.0128 (9)
C19A0.116 (5)0.090 (4)0.065 (3)0.069 (3)0.023 (3)0.030 (3)
C20A0.124 (5)0.105 (4)0.087 (4)0.081 (4)0.032 (4)0.026 (3)
C210.117 (2)0.0961 (17)0.1047 (19)0.0795 (16)0.0041 (16)0.0193 (15)
C220.0857 (15)0.0632 (12)0.0991 (17)0.0374 (11)0.0111 (13)0.0287 (12)
C230.0745 (13)0.0738 (12)0.0840 (14)0.0419 (11)0.0141 (11)0.0376 (11)
C20B0.113 (7)0.115 (7)0.089 (6)0.082 (5)0.018 (5)0.023 (5)
C19B0.111 (6)0.102 (6)0.068 (5)0.073 (5)0.018 (5)0.026 (5)
Geometric parameters (Å, º) top
S1—C171.6933 (19)C19B—C20B1.407 (18)
N1—C11.396 (3)C20A—C211.373 (8)
N1—C81.336 (2)C20B—C211.462 (12)
N1—C91.460 (3)C21—C221.329 (4)
N2—C61.390 (3)C22—C231.384 (3)
N2—C71.465 (4)C2—H20.9297
N2—C81.331 (2)C3—H30.9302
N3—C171.288 (2)C4—H40.9292
N3—C181.411 (3)C5—H50.9296
C1—C21.384 (3)C7—H7A0.9599
C1—C61.376 (3)C7—H7B0.9600
C2—C31.374 (4)C7—H7C0.9598
C3—C41.377 (4)C9—H9A0.9705
C4—C51.373 (4)C9—H9B0.9699
C5—C61.389 (3)C10—H10A0.9699
C8—C171.490 (3)C10—H10B0.9696
C9—C101.516 (3)C12—H120.9301
C10—C111.501 (3)C13—H130.9305
C11—C121.378 (4)C14—H140.9302
C11—C161.368 (3)C15—H150.9303
C12—C131.376 (5)C16—H160.9300
C13—C141.363 (5)C19A—H19A0.96 (5)
C14—C151.361 (5)C19B—H19B0.95 (6)
C15—C161.370 (5)C20A—H20A1.03 (7)
C18—C19A1.339 (7)C20B—H20B1.02 (9)
C18—C231.358 (3)C21—H210.9793
C18—C19B1.520 (11)C22—H220.9298
C19A—C20A1.384 (11)C23—H230.9305
S1···N13.4463 (16)C20A···H12x3.0359
S1···N23.5056 (18)C20B···H19Bvii3.05 (6)
S1···C233.264 (2)C20B···H5vi3.0177
S1···C9i3.544 (2)C21···H12x2.8677
S1···H9A3.1370C21···H7Avi2.9854
S1···H232.8080C22···H7Avi3.0446
S1···H3ii3.1052H2···H9B2.4288
S1···H9Ai2.9661H2···C93.0147
S1···H22iii2.9903H3···S1ii3.1052
N1···S13.4463 (16)H5···C73.0113
N1···N22.173 (2)H5···H7A2.3773
N1···N33.243 (2)H5···C19Bv2.9450
N1···C163.196 (3)H5···C20Bv3.0177
N2···S13.5056 (18)H7A···C52.7996
N2···N12.173 (2)H7A···C21v2.9854
N2···N33.153 (2)H7A···C22v3.0446
N3···N13.243 (2)H7A···H23ix2.4189
N3···N23.153 (2)H7A···H52.3773
N3···H10B2.7654H7B···C172.9633
N3···H15iv2.7276H7B···H7Bix2.4159
C1···C113.405 (3)H7C···C172.9737
C1···C163.470 (3)H9A···C172.8228
C2···C6ii3.554 (3)H9A···S1i2.9661
C5···C20Bv3.459 (12)H9A···S13.1370
C5···C19Bv3.382 (11)H9B···C22.8408
C6···C2ii3.554 (3)H9B···H22.4288
C9···S1i3.544 (2)H10A···H122.4655
C10···C173.510 (3)H10B···N32.7654
C11···C13.405 (3)H10B···C83.0508
C16···C13.470 (3)H10B···C172.9879
C16···N13.196 (3)H10B···H162.4083
C17···C103.510 (3)H10B···H20Avii2.3767
C19B···C5vi3.382 (11)H12···H10A2.4655
C19B···C19Bvii3.579 (14)H12···C20Axi3.0359
C20B···C5vi3.459 (12)H12···C21xi2.8677
C23···S13.264 (2)H13···C3viii3.0911
C2···H9B2.8408H15···N3iv2.7276
C3···H13viii3.0911H16···H20Bvii2.5930
C5···H7A2.7996H16···H10B2.4083
C7···H53.0113H19B···C19Bvii2.91 (5)
C7···H23ix3.0023H19B···C20Bvii3.05 (6)
C8···H10B3.0508H19B···H19Bvii2.43 (8)
C9···H23.0147H20A···H10Bvii2.3767
C10···H20Avii2.96 (7)H20A···C10vii2.96 (7)
C11···H20Avii3.10 (7)H20A···C11vii3.10 (7)
C16···H20Bvii2.90 (9)H20B···H16vii2.5930
C17···H7C2.9737H20B···C16vii2.90 (9)
C17···H232.8449H22···S1iii2.9903
C17···H9A2.8228H23···C7ix3.0023
C17···H7B2.9633H23···H7Aix2.4189
C17···H10B2.9879H23···C172.8449
C19B···H19Bvii2.91 (5)H23···S12.8080
C19B···H5vi2.9450
C1—N1—C8108.61 (15)C2—C3—H3119.03
C1—N1—C9126.32 (16)C4—C3—H3118.93
C8—N1—C9125.05 (16)C3—C4—H4118.98
C6—N2—C7126.42 (19)C5—C4—H4118.87
C6—N2—C8109.05 (17)C4—C5—H5121.94
C7—N2—C8124.46 (19)C6—C5—H5122.13
C17—N3—C18121.99 (16)N2—C7—H7A109.41
N1—C1—C2131.8 (2)N2—C7—H7B109.46
N1—C1—C6106.62 (17)N2—C7—H7C109.47
C2—C1—C6121.6 (2)H7A—C7—H7B109.54
C1—C2—C3116.3 (2)H7A—C7—H7C109.47
C2—C3—C4122.0 (3)H7B—C7—H7C109.48
C3—C4—C5122.1 (3)N1—C9—H9A109.11
C4—C5—C6115.9 (3)N1—C9—H9B109.13
N2—C6—C1106.62 (18)C10—C9—H9A109.11
N2—C6—C5131.4 (2)C10—C9—H9B109.17
C1—C6—C5122.0 (2)H9A—C9—H9B107.82
N1—C8—N2109.09 (16)C9—C10—H10A108.92
N1—C8—C17126.09 (17)C9—C10—H10B108.99
N2—C8—C17124.79 (17)C11—C10—H10A108.92
N1—C9—C10112.39 (16)C11—C10—H10B108.92
C9—C10—C11113.18 (17)H10A—C10—H10B107.77
C10—C11—C12121.1 (2)C11—C12—H12119.62
C10—C11—C16120.7 (2)C13—C12—H12119.76
C12—C11—C16118.1 (2)C12—C13—H13119.94
C11—C12—C13120.6 (3)C14—C13—H13119.95
C12—C13—C14120.1 (3)C13—C14—H14120.08
C13—C14—C15119.9 (3)C15—C14—H14120.02
C14—C15—C16119.9 (3)C14—C15—H15120.02
C11—C16—C15121.4 (2)C16—C15—H15120.13
S1—C17—N3134.86 (16)C11—C16—H16119.32
S1—C17—C8112.82 (13)C15—C16—H16119.26
N3—C17—C8112.32 (16)C18—C19A—H19A117 (3)
N3—C18—C19A115.8 (3)C20A—C19A—H19A122 (3)
N3—C18—C23126.49 (18)C20B—C19B—H19B120 (4)
N3—C18—C19B115.0 (5)C18—C19B—H19B122 (4)
C19A—C18—C23115.7 (3)C21—C20A—H20A121 (4)
C19B—C18—C23116.2 (5)C19A—C20A—H20A118 (4)
C18—C19A—C20A121.4 (6)C21—C20B—H20B123 (5)
C18—C19B—C20B117.5 (9)C19B—C20B—H20B119 (5)
C19A—C20A—C21120.6 (6)C20A—C21—H21119.72
C19B—C20B—C21117.3 (10)C22—C21—H21119.72
C20A—C21—C22116.0 (4)C20B—C21—H21119.69
C20B—C21—C22119.0 (5)C23—C22—H22119.43
C21—C22—C23121.1 (2)C21—C22—H22119.50
C18—C23—C22121.7 (2)C18—C23—H23119.15
C1—C2—H2121.80C22—C23—H23119.19
C3—C2—H2121.87
C8—N1—C1—C2178.41 (18)C1—C2—C3—C40.5 (3)
C9—N1—C1—C23.1 (3)C2—C3—C4—C50.2 (3)
C8—N1—C1—C60.20 (18)C3—C4—C5—C60.6 (3)
C9—N1—C1—C6178.65 (15)C4—C5—C6—C10.3 (3)
C1—N1—C8—N20.61 (18)C4—C5—C6—N2178.30 (19)
C9—N1—C8—N2177.87 (15)N2—C8—C17—S193.50 (19)
C1—N1—C8—C17177.49 (16)N1—C8—C17—S184.31 (19)
C9—N1—C8—C174.0 (3)N1—C8—C17—N396.1 (2)
C1—N1—C9—C10101.0 (2)N2—C8—C17—N386.1 (2)
C8—N1—C9—C1077.2 (2)N1—C9—C10—C1154.2 (2)
C6—N2—C8—N11.17 (19)C9—C10—C11—C1286.0 (3)
C7—N2—C8—C170.1 (3)C9—C10—C11—C1690.7 (2)
C7—N2—C6—C1178.3 (2)C10—C11—C12—C13176.3 (2)
C7—N2—C8—N1178.2 (2)C16—C11—C12—C130.4 (4)
C6—N2—C8—C17176.95 (16)C10—C11—C16—C15176.6 (3)
C8—N2—C6—C5177.5 (2)C12—C11—C16—C150.2 (4)
C7—N2—C6—C50.5 (3)C11—C12—C13—C140.6 (5)
C8—N2—C6—C11.3 (2)C12—C13—C14—C150.6 (5)
C18—N3—C17—C8177.86 (17)C13—C14—C15—C160.3 (5)
C18—N3—C17—S11.6 (3)C14—C15—C16—C110.2 (5)
C17—N3—C18—C19A154.8 (4)N3—C18—C23—C22177.0 (2)
C17—N3—C18—C2342.2 (3)C23—C18—C19A—C20A13.9 (8)
N1—C1—C2—C3177.21 (18)N3—C18—C19A—C20A178.7 (5)
C6—C1—C2—C30.8 (3)C19A—C18—C23—C2214.1 (5)
N1—C1—C6—C5178.03 (17)C18—C19A—C20A—C210.9 (11)
N1—C1—C6—N20.88 (18)C19A—C20A—C21—C2215.9 (9)
C2—C1—C6—C50.4 (3)C20A—C21—C22—C2315.8 (5)
C2—C1—C6—N2179.32 (16)C21—C22—C23—C181.0 (4)
Symmetry codes: (i) x, y+2, z; (ii) x+1, y+2, z; (iii) x, y+1, z; (iv) x+1, y+1, z+1; (v) x+1, y, z; (vi) x1, y, z; (vii) x, y+1, z+1; (viii) x+1, y+2, z+1; (ix) x+1, y+1, z; (x) x, y1, z; (xi) x, y+1, z.
 

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