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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1715.
Published online 2010 June 18. doi:  10.1107/S1600536810022920
PMCID: PMC3006876

4-Ethyl-1-[4-(methyl­sulfan­yl)benzyl­idene]thio­semicarbazide

Abstract

There are four independent mol­ecules in the asymmetric unit of the title compound, C11H15N3S2, with different conformations: the dihedral angles between the benzene rings and thio­urea units are 16.85 (9), 0.56 (10), 8.05 (12) and 4.56 (8)°. Each mol­ecule contains an intra­molecular N—H(...)N hydrogen bond, generating an S(5) ring. The crystal structure is stabilized by inter­molecular N—H(...)S hydrogen bonds.

Related literature

For a related structure and background references to thio­semicarbazones, see: Li & Jian (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1715-scheme1.jpg

Experimental

Crystal data

  • C11H15N3S2
  • M r = 253.38
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1715-efi1.jpg
  • a = 10.496 (2) Å
  • b = 15.737 (3) Å
  • c = 17.542 (4) Å
  • α = 111.07 (3)°
  • β = 91.62 (3)°
  • γ = 100.43 (3)°
  • V = 2645.4 (9) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.38 mm−1
  • T = 293 K
  • 0.22 × 0.20 × 0.18 mm

Data collection

  • Bruker SMART CCD diffractometer
  • 26033 measured reflections
  • 12032 independent reflections
  • 8042 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.053
  • wR(F 2) = 0.201
  • S = 1.31
  • 12032 reflections
  • 577 parameters
  • H-atom parameters constrained
  • Δρmax = 0.68 e Å−3
  • Δρmin = −0.44 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022920/hb5494sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022920/hb5494Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

As part of our ongoing studies of thiosemicarbazone compounds (Li & Jian, 2010), we synthesized the title compound (I), and describe its structure here. In the four independent molecules, the dihedral angle between the benzene ring and the thiourea unit is [16.85 (9)°], [0.56 (10)°], [8.05 (12)°], [4.56 (8)°] respectively.

Experimental

A mixture of 4-ethylthiosemicarbazide (0.1 mol), and 4-(methylthio)benzaldehyde (0.1 mol) was stirred in refluxing ethanol (20 ml) for 2 h to afford the title compound (0.086 mol, yield 86%). Colourless blocks of (I) were obtained by recrystallization from ethanol at room temperature.

Refinement

H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances=0.97 Å, and with Uiso=1.2–1.5Ueq.

Figures

Fig. 1.
The structure of (I) showing 30% probability displacement ellipsoids.

Crystal data

C11H15N3S2Z = 8
Mr = 253.38F(000) = 1072
Triclinic, P1Dx = 1.272 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.496 (2) ÅCell parameters from 8042 reflections
b = 15.737 (3) Åθ = 3.0–27.5°
c = 17.542 (4) ŵ = 0.38 mm1
α = 111.07 (3)°T = 293 K
β = 91.62 (3)°Block, colorless
γ = 100.43 (3)°0.22 × 0.20 × 0.18 mm
V = 2645.4 (9) Å3

Data collection

Bruker SMART CCD diffractometer8042 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.042
graphiteθmax = 27.5°, θmin = 3.0°
phi and ω scansh = −13→13
26033 measured reflectionsk = −20→20
12032 independent reflectionsl = −22→22

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.201H-atom parameters constrained
S = 1.31w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
12032 reflections(Δ/σ)max = 0.001
577 parametersΔρmax = 0.68 e Å3
0 restraintsΔρmin = −0.44 e Å3

Special details

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)

xyzUiso*/Ueq
S1D0.70888 (7)0.63167 (4)0.27855 (3)0.06536 (19)
S2A0.77477 (8)−0.09229 (4)0.25247 (3)0.0713 (2)
S1B0.81356 (8)−0.20823 (4)−0.11837 (3)0.0747 (2)
S2D0.91253 (8)1.22890 (5)0.82918 (4)0.0787 (2)
S1C0.59612 (10)−0.26828 (5)−0.35997 (4)0.0909 (3)
S2C0.57360 (9)0.35118 (5)0.15668 (5)0.0892 (3)
S1A0.63732 (9)−0.69992 (6)−0.29039 (5)0.0952 (3)
S2B1.00646 (10)−0.79759 (6)−0.60067 (5)0.0999 (3)
N3A0.72112 (19)−0.26196 (13)0.14045 (10)0.0570 (5)
H3AA0.6975−0.28040.17950.068*
N3D0.6760 (2)0.68551 (12)0.43757 (10)0.0601 (5)
H3DA0.67710.72970.48420.072*
N2A0.71480 (17)−0.32505 (12)0.06176 (10)0.0522 (4)
N2D0.75067 (19)0.80099 (12)0.39072 (10)0.0562 (4)
H2DA0.77000.82050.35170.067*
N1D0.76168 (17)0.86248 (12)0.46999 (10)0.0528 (4)
N1A0.7964 (2)−0.14877 (13)0.09172 (10)0.0604 (5)
H1AA0.7847−0.19340.04450.072*
C3D0.7090 (2)0.70904 (15)0.37417 (11)0.0507 (5)
C3A0.7648 (2)−0.17061 (15)0.15602 (12)0.0541 (5)
N3B0.8723 (2)−0.42118 (14)−0.30377 (11)0.0618 (5)
C5A0.66625 (19)−0.48223 (14)−0.03193 (12)0.0493 (5)
C4A0.6790 (2)−0.41118 (15)0.05027 (13)0.0512 (5)
H4AA0.6608−0.42860.09480.061*
C5D0.8371 (2)1.01651 (15)0.56714 (12)0.0517 (5)
C4D0.8144 (2)0.94679 (15)0.48379 (12)0.0534 (5)
H4DA0.83880.96420.44010.064*
N3C0.5771 (2)−0.04440 (14)−0.17236 (11)0.0680 (5)
N2B0.8282 (2)−0.34282 (14)−0.25800 (10)0.0663 (5)
H2BA0.7763−0.3203−0.28070.080*
N1B0.9511 (2)−0.34109 (14)−0.14897 (11)0.0666 (5)
H1BA0.9764−0.3872−0.18450.080*
C3B0.8681 (2)−0.30171 (16)−0.17630 (13)0.0608 (6)
C6A0.6774 (2)−0.45969 (16)−0.10174 (13)0.0610 (6)
H6AA0.6934−0.3976−0.09630.073*
C8D0.8865 (2)1.15085 (16)0.72642 (13)0.0573 (5)
C10D0.8050 (2)0.99256 (16)0.63471 (13)0.0583 (5)
H10A0.76790.93130.62690.070*
N2C0.6029 (3)−0.12828 (16)−0.22144 (11)0.0800 (7)
H2CA0.6489−0.1564−0.20090.096*
C8B0.9502 (2)−0.69882 (16)−0.54091 (14)0.0610 (5)
C6D0.8938 (2)1.10765 (16)0.58141 (14)0.0598 (5)
H6DA0.91581.12470.53720.072*
C8C0.5907 (2)0.24294 (16)0.08527 (14)0.0609 (5)
C8A0.6428 (2)−0.62037 (17)−0.18858 (14)0.0635 (6)
C5B0.8749 (2)−0.53968 (16)−0.43370 (13)0.0573 (5)
C9A0.6289 (2)−0.64442 (17)−0.12059 (16)0.0666 (6)
H9AA0.6117−0.7068−0.12680.080*
C7B0.8681 (3)−0.65617 (18)−0.56913 (13)0.0729 (7)
H7BA0.8373−0.6800−0.62450.087*
C10A0.6406 (2)−0.57573 (16)−0.04307 (14)0.0591 (5)
H10B0.6311−0.59270.00240.071*
C9D0.8283 (2)1.05956 (17)0.71286 (13)0.0632 (6)
H9DA0.80461.04330.75720.076*
C7A0.6651 (3)−0.52784 (19)−0.17804 (14)0.0705 (7)
H7AA0.6721−0.5113−0.22380.085*
C4B0.8349 (3)−0.45683 (17)−0.37994 (13)0.0646 (6)
H4BA0.7803−0.4292−0.40190.078*
C10B0.9567 (2)−0.58410 (18)−0.40533 (13)0.0650 (6)
H10C0.9866−0.5609−0.34990.078*
C2D0.6381 (3)0.59073 (18)0.43388 (14)0.0745 (7)
H2DB0.65880.58940.48760.089*
H2DC0.68860.55220.39570.089*
C3C0.5568 (3)−0.16705 (18)−0.30147 (14)0.0713 (7)
C6C0.5343 (3)0.13004 (18)−0.05242 (15)0.0656 (6)
H6CA0.48860.1116−0.10380.079*
C9B0.9939 (3)−0.66138 (19)−0.45749 (15)0.0693 (6)
H9BA1.0496−0.6896−0.43700.083*
C7D0.9188 (2)1.17422 (16)0.66004 (14)0.0628 (6)
H7DA0.95771.23520.66810.075*
C4C0.6275 (3)−0.0129 (2)−0.09849 (15)0.0810 (8)
H4CA0.6772−0.0480−0.08230.097*
C5C0.6116 (3)0.07495 (17)−0.03801 (13)0.0659 (6)
C2A0.8492 (3)−0.05562 (18)0.09475 (15)0.0809 (9)
H2AB0.8181−0.01100.14080.097*
H2AC0.8168−0.04960.04500.097*
N1C0.4853 (3)−0.12191 (17)−0.32778 (13)0.0853 (7)
H1CA0.4686−0.0718−0.29260.102*
C6B0.8302 (3)−0.57779 (18)−0.51630 (14)0.0746 (7)
H6BA0.7735−0.5502−0.53670.089*
C7C0.5234 (3)0.21250 (18)0.00832 (16)0.0709 (7)
H7CA0.46960.2484−0.00270.085*
C10C0.6784 (4)0.1063 (2)0.03940 (17)0.1071 (13)
H10D0.73240.07060.05070.129*
C9C0.6676 (4)0.1891 (2)0.10045 (16)0.0900 (10)
H9CA0.71320.20780.15200.108*
C2B1.0029 (3)−0.3124 (2)−0.06345 (15)0.0783 (7)
H2BB0.9320−0.3077−0.02880.094*
H2BC1.0604−0.2517−0.04620.094*
C11D0.9757 (3)1.3390 (2)0.82323 (17)0.0862 (9)
H11A0.99251.38590.87750.129*
H11B0.91351.35370.79130.129*
H11C1.05531.33670.79760.129*
C1B1.0759 (4)−0.3812 (3)−0.05415 (18)0.1076 (12)
H1BB1.1090−0.36220.00230.161*
H1BC1.1470−0.3848−0.08760.161*
H1BD1.0187−0.4412−0.07110.161*
C11A0.5706 (3)−0.8097 (2)−0.2859 (2)0.1097 (12)
H11D0.5645−0.8573−0.33950.165*
H11E0.4854−0.8092−0.26750.165*
H11F0.6258−0.8221−0.24820.165*
C1A0.9928 (4)−0.0328 (2)0.1032 (2)0.1091 (12)
H1AB1.02210.02980.10600.164*
H1AC1.0243−0.07500.05660.164*
H1AD1.0256−0.03840.15250.164*
C11C0.6779 (4)0.3679 (2)0.24419 (17)0.0959 (10)
H11G0.67430.42630.28670.144*
H11H0.76550.36830.22990.144*
H11I0.65030.31830.26350.144*
C1D0.4976 (4)0.5507 (2)0.4078 (2)0.1096 (12)
H1DB0.47850.48770.40540.164*
H1DC0.47640.55160.35460.164*
H1DD0.44700.58690.44660.164*
C11B0.9299 (4)−0.8277 (2)−0.70075 (18)0.1145 (13)
H11J0.9563−0.8820−0.73760.172*
H11K0.9548−0.7770−0.71900.172*
H11L0.8371−0.8407−0.69990.172*
C2C0.4309 (5)−0.1508 (3)−0.4138 (2)0.1359 (18)
H2CB0.4887−0.1851−0.44910.163*
H2CC0.3478−0.1933−0.42180.163*
C1C0.4128 (6)−0.0818 (4)−0.4382 (3)0.172 (2)
H1CB0.3779−0.1075−0.49480.258*
H1CC0.4945−0.0398−0.43190.258*
H1CD0.3529−0.0487−0.40530.258*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S1D0.0967 (5)0.0526 (3)0.0385 (3)0.0130 (3)0.0152 (3)0.0077 (2)
S2A0.1070 (5)0.0539 (3)0.0419 (3)0.0123 (3)0.0111 (3)0.0065 (2)
S1B0.1203 (6)0.0505 (3)0.0483 (3)0.0269 (3)0.0128 (3)0.0075 (2)
S2D0.0965 (5)0.0675 (4)0.0514 (3)0.0182 (4)0.0026 (3)−0.0028 (3)
S1C0.1435 (7)0.0710 (5)0.0468 (3)0.0242 (5)0.0222 (4)0.0065 (3)
S2C0.1155 (6)0.0633 (4)0.0799 (4)0.0435 (4)0.0096 (4)0.0041 (3)
S1A0.1066 (6)0.0885 (6)0.0643 (4)0.0383 (5)0.0037 (4)−0.0109 (4)
S2B0.1272 (7)0.0838 (5)0.0892 (5)0.0574 (5)0.0367 (5)0.0136 (4)
N3A0.0729 (11)0.0503 (10)0.0397 (8)0.0053 (9)0.0075 (8)0.0106 (7)
N3D0.0909 (13)0.0461 (10)0.0395 (8)0.0157 (9)0.0130 (9)0.0101 (7)
N2A0.0592 (10)0.0494 (10)0.0410 (8)0.0119 (8)0.0037 (7)0.0082 (7)
N2D0.0743 (11)0.0474 (10)0.0395 (8)0.0061 (8)0.0095 (8)0.0102 (7)
N1D0.0615 (10)0.0479 (10)0.0411 (8)0.0110 (8)0.0028 (8)0.0075 (7)
N1A0.0905 (13)0.0443 (10)0.0422 (9)0.0149 (9)0.0042 (9)0.0108 (7)
C3D0.0574 (11)0.0493 (11)0.0402 (9)0.0110 (9)0.0043 (9)0.0105 (8)
C3A0.0659 (12)0.0485 (11)0.0436 (10)0.0150 (10)0.0040 (9)0.0104 (9)
N3B0.0800 (12)0.0551 (11)0.0453 (9)0.0186 (9)0.0140 (9)0.0100 (8)
C5A0.0441 (9)0.0489 (11)0.0492 (10)0.0115 (8)0.0030 (8)0.0106 (9)
C4A0.0556 (11)0.0486 (12)0.0478 (10)0.0104 (9)0.0065 (9)0.0161 (9)
C5D0.0540 (11)0.0493 (11)0.0469 (10)0.0130 (9)0.0074 (9)0.0106 (9)
C4D0.0621 (12)0.0494 (12)0.0451 (10)0.0117 (10)0.0070 (9)0.0130 (9)
N3C0.0942 (14)0.0589 (12)0.0491 (10)0.0246 (11)0.0133 (10)0.0130 (9)
N2B0.0976 (14)0.0554 (11)0.0430 (9)0.0286 (10)0.0108 (10)0.0082 (8)
N1B0.0814 (13)0.0629 (12)0.0460 (9)0.0213 (10)0.0070 (9)0.0057 (8)
C3B0.0774 (14)0.0512 (12)0.0452 (11)0.0066 (11)0.0152 (10)0.0101 (9)
C6A0.0747 (14)0.0515 (13)0.0503 (11)0.0073 (11)0.0003 (11)0.0145 (10)
C8D0.0573 (11)0.0520 (12)0.0506 (11)0.0149 (10)0.0039 (10)0.0034 (9)
C10D0.0697 (13)0.0490 (12)0.0479 (11)0.0070 (10)0.0019 (10)0.0110 (9)
N2C0.1209 (18)0.0689 (14)0.0436 (10)0.0397 (13)0.0111 (11)0.0033 (9)
C8B0.0715 (13)0.0535 (13)0.0585 (12)0.0197 (11)0.0223 (11)0.0169 (10)
C6D0.0714 (14)0.0493 (12)0.0526 (11)0.0095 (10)0.0107 (10)0.0129 (9)
C8C0.0732 (14)0.0511 (12)0.0585 (12)0.0226 (11)0.0109 (11)0.0154 (10)
C8A0.0585 (12)0.0613 (14)0.0571 (12)0.0210 (11)0.0045 (10)0.0019 (11)
C5B0.0706 (13)0.0556 (13)0.0444 (10)0.0187 (11)0.0105 (10)0.0139 (9)
C9A0.0701 (14)0.0455 (12)0.0763 (15)0.0192 (11)0.0077 (12)0.0097 (11)
C7B0.106 (2)0.0682 (16)0.0422 (11)0.0349 (15)0.0066 (12)0.0091 (11)
C10A0.0672 (13)0.0519 (12)0.0585 (12)0.0164 (10)0.0078 (11)0.0186 (10)
C9D0.0747 (14)0.0642 (14)0.0463 (11)0.0131 (12)0.0064 (11)0.0159 (10)
C7A0.0849 (16)0.0728 (17)0.0473 (11)0.0153 (13)0.0049 (12)0.0150 (11)
C4B0.0866 (16)0.0567 (13)0.0472 (11)0.0237 (12)0.0081 (11)0.0107 (10)
C10B0.0782 (15)0.0688 (15)0.0458 (11)0.0223 (12)0.0016 (11)0.0156 (10)
C2D0.121 (2)0.0592 (14)0.0466 (11)0.0271 (15)0.0150 (13)0.0188 (10)
C3C0.0975 (18)0.0653 (15)0.0440 (11)0.0066 (14)0.0162 (12)0.0161 (11)
C6C0.0747 (14)0.0615 (14)0.0585 (13)0.0219 (12)−0.0009 (11)0.0165 (11)
C9B0.0745 (15)0.0723 (16)0.0648 (14)0.0324 (13)0.0087 (12)0.0214 (12)
C7D0.0689 (14)0.0452 (12)0.0634 (13)0.0093 (10)0.0091 (11)0.0082 (10)
C4C0.120 (2)0.0703 (17)0.0514 (13)0.0495 (16)−0.0003 (14)0.0073 (11)
C5C0.0911 (17)0.0586 (14)0.0498 (11)0.0332 (13)0.0062 (12)0.0137 (10)
C2A0.150 (3)0.0504 (14)0.0482 (12)0.0322 (16)0.0097 (15)0.0191 (10)
N1C0.1164 (19)0.0747 (15)0.0538 (11)0.0089 (14)−0.0073 (12)0.0169 (11)
C6B0.110 (2)0.0676 (16)0.0466 (11)0.0409 (15)0.0020 (13)0.0111 (11)
C7C0.0818 (16)0.0571 (14)0.0741 (15)0.0285 (12)0.0001 (13)0.0183 (12)
C10C0.174 (3)0.086 (2)0.0610 (15)0.083 (2)−0.0183 (19)0.0023 (14)
C9C0.139 (3)0.0724 (17)0.0543 (13)0.0541 (18)−0.0147 (16)0.0044 (12)
C2B0.0872 (17)0.0840 (19)0.0493 (12)0.0206 (15)−0.0004 (12)0.0069 (12)
C11D0.0785 (17)0.0711 (17)0.0765 (17)0.0053 (14)0.0112 (14)−0.0065 (13)
C1B0.125 (3)0.136 (3)0.0639 (16)0.062 (2)0.0024 (18)0.0238 (18)
C11A0.0859 (19)0.083 (2)0.114 (3)0.0141 (17)0.0107 (19)−0.0176 (18)
C1A0.133 (3)0.067 (2)0.118 (3)−0.0126 (19)0.008 (2)0.0404 (18)
C11C0.133 (3)0.0739 (19)0.0641 (16)0.0293 (18)0.0092 (17)0.0015 (13)
C1D0.124 (3)0.082 (2)0.112 (3)−0.014 (2)0.011 (2)0.040 (2)
C11B0.177 (4)0.074 (2)0.0721 (18)0.026 (2)0.041 (2)0.0006 (15)
C2C0.217 (5)0.098 (3)0.074 (2)0.007 (3)−0.044 (3)0.0247 (19)
C1C0.240 (6)0.159 (5)0.125 (3)0.067 (4)−0.062 (4)0.054 (3)

Geometric parameters (Å, °)

S1D—C3D1.681 (2)C9A—C10A1.385 (3)
S2A—C3A1.684 (2)C9A—H9AA0.9300
S1B—C3B1.670 (3)C7B—C6B1.384 (3)
S2D—C8D1.758 (2)C7B—H7BA0.9300
S2D—C11D1.780 (3)C10A—H10B0.9300
S1C—C3C1.688 (3)C9D—H9DA0.9300
S2C—C8C1.758 (2)C7A—H7AA0.9300
S2C—C11C1.770 (3)C4B—H4BA0.9300
S1A—C8A1.767 (2)C10B—C9B1.364 (3)
S1A—C11A1.773 (4)C10B—H10C0.9300
S2B—C8B1.749 (2)C2D—C1D1.483 (5)
S2B—C11B1.771 (4)C2D—H2DB0.9700
N3A—C3A1.350 (3)C2D—H2DC0.9700
N3A—N2A1.372 (2)C3C—N1C1.300 (4)
N3A—H3AA0.8600C6C—C5C1.369 (3)
N3D—C3D1.329 (3)C6C—C7C1.378 (3)
N3D—C2D1.450 (3)C6C—H6CA0.9300
N3D—H3DA0.8600C9B—H9BA0.9300
N2A—C4A1.278 (3)C7D—H7DA0.9300
N2D—C3D1.353 (3)C4C—C5C1.451 (3)
N2D—N1D1.366 (2)C4C—H4CA0.9300
N2D—H2DA0.8600C5C—C10C1.385 (4)
N1D—C4D1.273 (3)C2A—C1A1.476 (5)
N1A—C3A1.326 (3)C2A—H2AB0.9700
N1A—C2A1.451 (3)C2A—H2AC0.9700
N1A—H1AA0.8600N1C—C2C1.474 (4)
N3B—C4B1.267 (3)N1C—H1CA0.8600
N3B—N2B1.377 (3)C6B—H6BA0.9300
C5A—C10A1.386 (3)C7C—H7CA0.9300
C5A—C6A1.394 (3)C10C—C9C1.383 (4)
C5A—C4A1.457 (3)C10C—H10D0.9300
C4A—H4AA0.9300C9C—H9CA0.9300
C5D—C6D1.378 (3)C2B—C1B1.485 (4)
C5D—C10D1.399 (3)C2B—H2BB0.9700
C5D—C4D1.460 (3)C2B—H2BC0.9700
C4D—H4DA0.9300C11D—H11A0.9600
N3C—C4C1.268 (3)C11D—H11B0.9600
N3C—N2C1.372 (3)C11D—H11C0.9600
N2B—C3B1.360 (3)C1B—H1BB0.9600
N2B—H2BA0.8600C1B—H1BC0.9600
N1B—C3B1.326 (3)C1B—H1BD0.9600
N1B—C2B1.459 (3)C11A—H11D0.9600
N1B—H1BA0.8600C11A—H11E0.9600
C6A—C7A1.366 (3)C11A—H11F0.9600
C6A—H6AA0.9300C1A—H1AB0.9600
C8D—C7D1.375 (3)C1A—H1AC0.9600
C8D—C9D1.386 (3)C1A—H1AD0.9600
C10D—C9D1.378 (3)C11C—H11G0.9600
C10D—H10A0.9300C11C—H11H0.9600
N2C—C3C1.347 (3)C11C—H11I0.9600
N2C—H2CA0.8600C1D—H1DB0.9600
C8B—C7B1.364 (3)C1D—H1DC0.9600
C8B—C9B1.394 (3)C1D—H1DD0.9600
C6D—C7D1.382 (3)C11B—H11J0.9600
C6D—H6DA0.9300C11B—H11K0.9600
C8C—C9C1.357 (4)C11B—H11L0.9600
C8C—C7C1.382 (3)C2C—C1C1.344 (5)
C8A—C7A1.375 (4)C2C—H2CB0.9700
C8A—C9A1.379 (4)C2C—H2CC0.9700
C5B—C6B1.384 (3)C1C—H1CB0.9600
C5B—C10B1.384 (3)C1C—H1CC0.9600
C5B—C4B1.450 (3)C1C—H1CD0.9600
C8D—S2D—C11D104.40 (13)H2DB—C2D—H2DC107.8
C8C—S2C—C11C104.08 (13)N1C—C3C—N2C116.4 (2)
C8A—S1A—C11A104.33 (15)N1C—C3C—S1C124.9 (2)
C8B—S2B—C11B104.45 (16)N2C—C3C—S1C118.7 (2)
C3A—N3A—N2A119.28 (17)C5C—C6C—C7C120.8 (2)
C3A—N3A—H3AA120.4C5C—C6C—H6CA119.6
N2A—N3A—H3AA120.4C7C—C6C—H6CA119.6
C3D—N3D—C2D124.72 (18)C10B—C9B—C8B121.3 (2)
C3D—N3D—H3DA117.6C10B—C9B—H9BA119.4
C2D—N3D—H3DA117.6C8B—C9B—H9BA119.4
C4A—N2A—N3A117.34 (18)C8D—C7D—C6D120.4 (2)
C3D—N2D—N1D119.31 (17)C8D—C7D—H7DA119.8
C3D—N2D—H2DA120.3C6D—C7D—H7DA119.8
N1D—N2D—H2DA120.3N3C—C4C—C5C123.3 (2)
C4D—N1D—N2D117.00 (18)N3C—C4C—H4CA118.3
C3A—N1A—C2A125.21 (19)C5C—C4C—H4CA118.3
C3A—N1A—H1AA117.4C6C—C5C—C10C117.1 (2)
C2A—N1A—H1AA117.4C6C—C5C—C4C124.1 (2)
N3D—C3D—N2D116.24 (18)C10C—C5C—C4C118.8 (2)
N3D—C3D—S1D123.83 (17)N1A—C2A—C1A113.2 (2)
N2D—C3D—S1D119.84 (15)N1A—C2A—H2AB108.9
N1A—C3A—N3A115.98 (18)C1A—C2A—H2AB108.9
N1A—C3A—S2A124.11 (17)N1A—C2A—H2AC108.9
N3A—C3A—S2A119.91 (16)C1A—C2A—H2AC108.9
C4B—N3B—N2B117.1 (2)H2AB—C2A—H2AC107.8
C10A—C5A—C6A117.6 (2)C3C—N1C—C2C124.4 (3)
C10A—C5A—C4A120.3 (2)C3C—N1C—H1CA117.8
C6A—C5A—C4A122.0 (2)C2C—N1C—H1CA117.8
N2A—C4A—C5A120.58 (19)C5B—C6B—C7B121.3 (2)
N2A—C4A—H4AA119.7C5B—C6B—H6BA119.3
C5A—C4A—H4AA119.7C7B—C6B—H6BA119.3
C6D—C5D—C10D118.2 (2)C6C—C7C—C8C121.4 (2)
C6D—C5D—C4D120.6 (2)C6C—C7C—H7CA119.3
C10D—C5D—C4D121.2 (2)C8C—C7C—H7CA119.3
N1D—C4D—C5D121.0 (2)C9C—C10C—C5C122.2 (3)
N1D—C4D—H4DA119.5C9C—C10C—H10D118.9
C5D—C4D—H4DA119.5C5C—C10C—H10D118.9
C4C—N3C—N2C115.7 (2)C8C—C9C—C10C120.1 (2)
C3B—N2B—N3B118.8 (2)C8C—C9C—H9CA120.0
C3B—N2B—H2BA120.6C10C—C9C—H9CA120.0
N3B—N2B—H2BA120.6N1B—C2B—C1B110.0 (2)
C3B—N1B—C2B125.2 (2)N1B—C2B—H2BB109.7
C3B—N1B—H1BA117.4C1B—C2B—H2BB109.7
C2B—N1B—H1BA117.4N1B—C2B—H2BC109.7
N1B—C3B—N2B115.0 (2)C1B—C2B—H2BC109.7
N1B—C3B—S1B124.81 (17)H2BB—C2B—H2BC108.2
N2B—C3B—S1B120.1 (2)S2D—C11D—H11A109.5
C7A—C6A—C5A120.7 (2)S2D—C11D—H11B109.5
C7A—C6A—H6AA119.6H11A—C11D—H11B109.5
C5A—C6A—H6AA119.6S2D—C11D—H11C109.5
C7D—C8D—C9D118.8 (2)H11A—C11D—H11C109.5
C7D—C8D—S2D124.82 (18)H11B—C11D—H11C109.5
C9D—C8D—S2D116.42 (18)C2B—C1B—H1BB109.5
C9D—C10D—C5D120.1 (2)C2B—C1B—H1BC109.5
C9D—C10D—H10A119.9H1BB—C1B—H1BC109.5
C5D—C10D—H10A119.9C2B—C1B—H1BD109.5
C3C—N2C—N3C120.6 (2)H1BB—C1B—H1BD109.5
C3C—N2C—H2CA119.7H1BC—C1B—H1BD109.5
N3C—N2C—H2CA119.7S1A—C11A—H11D109.5
C7B—C8B—C9B118.1 (2)S1A—C11A—H11E109.5
C7B—C8B—S2B125.57 (19)H11D—C11A—H11E109.5
C9B—C8B—S2B116.4 (2)S1A—C11A—H11F109.5
C5D—C6D—C7D121.4 (2)H11D—C11A—H11F109.5
C5D—C6D—H6DA119.3H11E—C11A—H11F109.5
C7D—C6D—H6DA119.3C2A—C1A—H1AB109.5
C9C—C8C—C7C118.4 (2)C2A—C1A—H1AC109.5
C9C—C8C—S2C124.19 (19)H1AB—C1A—H1AC109.5
C7C—C8C—S2C117.39 (18)C2A—C1A—H1AD109.5
C7A—C8A—C9A118.9 (2)H1AB—C1A—H1AD109.5
C7A—C8A—S1A116.1 (2)H1AC—C1A—H1AD109.5
C9A—C8A—S1A125.0 (2)S2C—C11C—H11G109.5
C6B—C5B—C10B117.6 (2)S2C—C11C—H11H109.5
C6B—C5B—C4B120.2 (2)H11G—C11C—H11H109.5
C10B—C5B—C4B122.3 (2)S2C—C11C—H11I109.5
C8A—C9A—C10A120.0 (2)H11G—C11C—H11I109.5
C8A—C9A—H9AA120.0H11H—C11C—H11I109.5
C10A—C9A—H9AA120.0C2D—C1D—H1DB109.5
C8B—C7B—C6B120.7 (2)C2D—C1D—H1DC109.5
C8B—C7B—H7BA119.6H1DB—C1D—H1DC109.5
C6B—C7B—H7BA119.6C2D—C1D—H1DD109.5
C9A—C10A—C5A121.3 (2)H1DB—C1D—H1DD109.5
C9A—C10A—H10B119.3H1DC—C1D—H1DD109.5
C5A—C10A—H10B119.3S2B—C11B—H11J109.5
C10D—C9D—C8D121.1 (2)S2B—C11B—H11K109.5
C10D—C9D—H9DA119.5H11J—C11B—H11K109.5
C8D—C9D—H9DA119.5S2B—C11B—H11L109.5
C6A—C7A—C8A121.4 (2)H11J—C11B—H11L109.5
C6A—C7A—H7AA119.3H11K—C11B—H11L109.5
C8A—C7A—H7AA119.3C1C—C2C—N1C115.8 (4)
N3B—C4B—C5B121.7 (2)C1C—C2C—H2CB108.3
N3B—C4B—H4BA119.2N1C—C2C—H2CB108.3
C5B—C4B—H4BA119.2C1C—C2C—H2CC108.3
C9B—C10B—C5B121.0 (2)N1C—C2C—H2CC108.3
C9B—C10B—H10C119.5H2CB—C2C—H2CC107.4
C5B—C10B—H10C119.5C2C—C1C—H1CB109.5
N3D—C2D—C1D113.1 (3)C2C—C1C—H1CC109.5
N3D—C2D—H2DB109.0H1CB—C1C—H1CC109.5
C1D—C2D—H2DB109.0C2C—C1C—H1CD109.5
N3D—C2D—H2DC109.0H1CB—C1C—H1CD109.5
C1D—C2D—H2DC109.0H1CC—C1C—H1CD109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1A—H1AA···N2A0.862.202.602 (3)108
N1B—H1BA···N3B0.862.172.585 (3)109
N1C—H1CA···N3C0.862.232.624 (3)108
N3D—H3DA···N1D0.862.222.610 (3)107
N3A—H3AA···S1Di0.862.593.398 (2)156
N2D—H2DA···S2Aii0.862.573.402 (2)163
N1A—H1AA···S1B0.862.813.4798 (19)136
N2B—H2BA···S1C0.862.723.579 (2)174
N2C—H2CA···S1B0.862.643.487 (3)168

Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5494).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Li, Y.-F. & Jian, F.-F. (2010). Acta Cryst. E66, o1399. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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