organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

2-[(2-Hy­dr­oxy­naphthalen-1-yl)methyl­­idene­amino]-5,6,7,8-tetra­hydro-4H-cyclo­hepta­[b]thio­phene-3-carbo­nitrile

aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, bCenter of Excellence for Advanced Materials Research (CEAMR), Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and cDepartment of Chemistry, University of Gujrat, Gujrat, Pakistan
*Correspondence e-mail: aasiri2@kau.edu.sa, ghulam.mustafa@uog.edu.pk

(Received 27 December 2012; accepted 2 January 2013; online 9 January 2013)

Two independent mol­ecules, A and B, comprise the asymmetric unit of the title compound, C21H18N2OS, with the difference in the angle of orientation between the naphthalene ring system and the mean plane of the cyclo­heptyl ring [16.13 (1) in A and 11.48 (5)° in B], being evident. The cyclo­heptyl ring adopts a distorted chair conformation in each mol­ecule with r.m.s. deviations of 0.2345 (4) (A) and 0.2302 (4) Å (B). Intra­molecular O—H⋯N hydrogen bonding generates planar six-membered S(6) loops with r.m.s. deviations of 0.0099 (1) (A) and 0.0286 (1) Å (B).

Related literature

For the synthesis and related structures, see: Asiri et al. (2011a[Asiri, A. M., Khan, S. A. & Tahir, M. N. (2011a). Acta Cryst. E67, o2254.],b[Asiri, A. M., Khan, S. A. & Tahir, M. N. (2011b). Acta Cryst. E67, o2355.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C21H18N2OS

  • Mr = 346.43

  • Orthorhombic, P b c a

  • a = 13.5472 (2) Å

  • b = 14.4747 (4) Å

  • c = 35.7902 (6) Å

  • V = 7018.2 (2) Å3

  • Z = 16

  • Cu Kα radiation

  • μ = 1.71 mm−1

  • T = 296 K

  • 0.37 × 0.21 × 0.14 mm

Data collection
  • Agilent SuperNova (Dual, Cu at zero, Atlas, CCD) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.858, Tmax = 1.000

  • 28490 measured reflections

  • 7066 independent reflections

  • 5288 reflections with I > 2σ(I)

  • Rint = 0.035

Refinement
  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 0.161

  • S = 1.02

  • 7066 reflections

  • 457 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.52 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1O⋯N1 0.82 (3) 1.84 (3) 2.578 (2) 150 (3)
O2—H2O⋯N3 0.82 (3) 1.84 (3) 2.582 (2) 151 (3)

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]).

Supporting information


Comment top

In extension of synthesis of Schiff bases containing a thiophene (Asiri et al. 2011a; 2011b) residue, we herein report the crystal structure of title compound.

The title compound (I), Fig. 1, crystallized with two molecules per asymmetric unit. The cycloheptyl ring adopted a chair conformation in each molecule with the r. m. s. deviations being 0.2345 (4) & 0.2302 (4) Å, respectively. The naphthalene ring system is inclined at dihedral angle of 4.97 (4) & 16.13 (1)° with respect to the planes produced from best fitted atoms of thiophene and cycloheptyl rings, respectively in molecule A while the corresponding inclination angles in molecule B are 4.16 (1) & 11.48 (5)°. The thiophene and cycloheptyl rings planes are oriented at dihedral angles of 16.10 (7)° and 15.22 (6)° with respect to each other in molecules A & B. Only intramolecular O—H···N classical hydrogen bonding is observed in both molecules which generates planar six-membered ring motifs S(6) (Bernstein et al., 1995) with r. m. s. deviations of 0.0099 (1) & 0.0286 (1) Å from the least-squares planes of member atoms, see Table 1 for details.

Related literature top

For the synthesis and related structures, see: Asiri et al. (2011a,b). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

The title compound was prepared following literature methods (Asiri et al. 2011a; 2011b) and recrystallized from its methanol solution by slow evaporation.

Refinement top

The C—H H-atoms were positioned with idealized geometry with C—H = 0.93 Å for aromatic-H and C—H = 0.97 Å for methylene groups. H-atoms were refined as riding with Uiso(H) = 1.2Ueq(C). The O—H atoms were refined with Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and X-SEED (Barbour, 2001).

Figures top
[Figure 1] Fig. 1. The labelled molecular structures of the two independent molecules comprising the asymmetric unit of (I) with displacement ellipsoids drawn at the 50% probability level. The intramolecular hydrogen bonding shown as dashed lines.
2-[(2-Hydroxynaphthalen-1-yl)methylideneamino]-5,6,7,8-tetrahydro-4H- cyclohepta[b]thiophene-3-carbonitrile top
Crystal data top
C21H18N2OSF(000) = 2912
Mr = 346.43Dx = 1.311 Mg m3
Orthorhombic, PbcaCu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ac 2abCell parameters from 7977 reflections
a = 13.5472 (2) Åθ = 3.3–74.7°
b = 14.4747 (4) ŵ = 1.71 mm1
c = 35.7902 (6) ÅT = 296 K
V = 7018.2 (2) Å3Prismatic, dark red
Z = 160.37 × 0.21 × 0.14 mm
Data collection top
Agilent SuperNova (Dual, Cu at zero, Atlas, CCD)
diffractometer
7066 independent reflections
Radiation source: SuperNova (Cu) X-ray Source5288 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.035
ω scansθmax = 74.9°, θmin = 4.1°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
h = 1614
Tmin = 0.858, Tmax = 1.000k = 1713
28490 measured reflectionsl = 4444
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0753P)2 + 3.2292P]
where P = (Fo2 + 2Fc2)/3
7066 reflections(Δ/σ)max = 0.001
457 parametersΔρmax = 0.52 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C21H18N2OSV = 7018.2 (2) Å3
Mr = 346.43Z = 16
Orthorhombic, PbcaCu Kα radiation
a = 13.5472 (2) ŵ = 1.71 mm1
b = 14.4747 (4) ÅT = 296 K
c = 35.7902 (6) Å0.37 × 0.21 × 0.14 mm
Data collection top
Agilent SuperNova (Dual, Cu at zero, Atlas, CCD)
diffractometer
7066 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
5288 reflections with I > 2σ(I)
Tmin = 0.858, Tmax = 1.000Rint = 0.035
28490 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.161H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.52 e Å3
7066 reflectionsΔρmin = 0.25 e Å3
457 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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) top
xyzUiso*/Ueq
S10.24913 (4)0.21343 (5)0.314590 (15)0.05676 (19)
S20.45786 (4)0.50708 (5)0.564135 (16)0.05789 (19)
O10.30203 (12)0.26884 (15)0.46051 (5)0.0657 (5)
O20.51390 (13)0.57956 (16)0.70915 (5)0.0684 (5)
N10.27388 (13)0.23563 (13)0.39056 (5)0.0472 (4)
N20.0201 (2)0.2458 (3)0.42460 (7)0.0989 (10)
N30.48552 (13)0.54653 (14)0.63907 (5)0.0510 (5)
N40.2337 (2)0.5752 (3)0.67298 (7)0.0986 (10)
C10.43541 (16)0.24092 (16)0.41754 (6)0.0459 (5)
C20.54027 (16)0.23125 (16)0.41241 (6)0.0499 (5)
C30.58494 (18)0.2128 (2)0.37759 (8)0.0645 (7)
H30.54560.20700.35640.077*
C40.6851 (2)0.2034 (2)0.37445 (10)0.0812 (9)
H40.71300.19080.35130.097*
C50.7461 (2)0.2124 (2)0.40592 (11)0.0816 (9)
H50.81410.20640.40350.098*
C60.7060 (2)0.2298 (2)0.43951 (9)0.0713 (8)
H60.74700.23560.46020.086*
C70.60312 (17)0.23961 (17)0.44399 (7)0.0557 (6)
C80.56125 (19)0.25724 (19)0.47943 (7)0.0625 (7)
H80.60250.26260.50010.075*
C90.46320 (19)0.2665 (2)0.48411 (7)0.0611 (6)
H90.43770.27800.50780.073*
C100.39935 (17)0.25896 (17)0.45341 (6)0.0511 (5)
C110.36858 (16)0.23066 (16)0.38672 (6)0.0475 (5)
H110.39440.22000.36300.057*
C120.21176 (16)0.22661 (16)0.36021 (6)0.0465 (5)
C130.11097 (16)0.22964 (19)0.36215 (6)0.0531 (6)
C140.06278 (18)0.2232 (2)0.32699 (7)0.0670 (7)
C150.12889 (19)0.2154 (2)0.29865 (7)0.0673 (7)
C160.1107 (3)0.2146 (3)0.25696 (8)0.0941 (11)
H16A0.09410.27680.24920.113*
H16B0.17180.19780.24460.113*
C170.0333 (3)0.1525 (3)0.24402 (9)0.1011 (12)
H17A0.04900.09070.25270.121*
H17B0.03520.15120.21690.121*
C180.0719 (3)0.1746 (3)0.25595 (9)0.0967 (11)
H18A0.08660.23770.24870.116*
H18B0.11650.13460.24220.116*
C190.0935 (2)0.1643 (3)0.29717 (11)0.1069 (13)
H19A0.16440.16770.30060.128*
H19B0.07280.10300.30480.128*
C200.0477 (2)0.2311 (3)0.32213 (10)0.1028 (13)
H20A0.07830.22540.34650.123*
H20B0.06240.29260.31290.123*
C210.06072 (18)0.2395 (2)0.39699 (7)0.0646 (7)
C220.64645 (16)0.54730 (16)0.66648 (6)0.0489 (5)
C230.75161 (17)0.53553 (17)0.66162 (6)0.0508 (5)
C240.79674 (19)0.5194 (2)0.62665 (7)0.0635 (7)
H240.75780.51620.60530.076*
C250.8967 (2)0.5085 (2)0.62369 (9)0.0763 (8)
H250.92450.49730.60040.092*
C260.9576 (2)0.5139 (2)0.65491 (10)0.0767 (8)
H261.02550.50660.65250.092*
C270.9170 (2)0.5298 (2)0.68894 (9)0.0699 (8)
H270.95770.53320.70980.084*
C280.81442 (18)0.54127 (18)0.69330 (7)0.0557 (6)
C290.77185 (19)0.55757 (19)0.72897 (7)0.0621 (7)
H290.81270.55960.74980.075*
C300.6739 (2)0.57016 (19)0.73347 (7)0.0622 (6)
H300.64830.58150.75710.075*
C310.61033 (18)0.56608 (18)0.70233 (6)0.0535 (6)
C320.57975 (16)0.53732 (17)0.63555 (6)0.0508 (5)
H320.60550.52370.61210.061*
C330.42264 (16)0.53346 (17)0.60903 (6)0.0489 (5)
C340.32167 (16)0.54044 (17)0.61095 (6)0.0500 (5)
C350.27183 (17)0.52450 (18)0.57632 (6)0.0526 (6)
C360.33707 (18)0.50529 (19)0.54855 (7)0.0563 (6)
C370.3190 (2)0.4775 (3)0.50862 (7)0.0785 (9)
H37A0.38110.48100.49520.094*
H37B0.29800.41340.50830.094*
C380.2441 (3)0.5336 (3)0.48794 (8)0.0933 (11)
H38A0.24620.51590.46180.112*
H38B0.26330.59810.48940.112*
C390.1380 (2)0.5250 (3)0.50151 (9)0.0816 (9)
H39A0.09470.55230.48300.098*
H39B0.12150.46000.50340.098*
C400.1183 (2)0.5701 (2)0.53854 (8)0.0778 (8)
H40A0.14290.63290.53730.093*
H40B0.04730.57370.54180.093*
C410.16098 (18)0.5257 (2)0.57281 (8)0.0686 (7)
H41A0.13780.46230.57380.082*
H41B0.13440.55720.59450.082*
C420.27270 (18)0.5608 (2)0.64544 (7)0.0624 (7)
H1O0.272 (3)0.261 (2)0.4409 (9)0.094*
H2O0.486 (3)0.577 (3)0.6889 (9)0.094*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0477 (3)0.0840 (5)0.0386 (3)0.0013 (3)0.0038 (2)0.0040 (3)
S20.0453 (3)0.0822 (5)0.0461 (3)0.0019 (3)0.0062 (2)0.0034 (3)
O10.0496 (10)0.1030 (15)0.0445 (9)0.0027 (9)0.0032 (7)0.0078 (9)
O20.0559 (10)0.1014 (15)0.0480 (9)0.0012 (10)0.0052 (8)0.0017 (10)
N10.0428 (9)0.0580 (11)0.0408 (9)0.0009 (8)0.0020 (7)0.0018 (8)
N20.0766 (17)0.156 (3)0.0644 (15)0.0023 (18)0.0201 (14)0.0130 (17)
N30.0453 (10)0.0644 (13)0.0432 (9)0.0002 (9)0.0012 (8)0.0046 (9)
N40.0770 (17)0.167 (3)0.0524 (13)0.0185 (18)0.0161 (12)0.0012 (17)
C10.0453 (11)0.0495 (13)0.0430 (11)0.0007 (9)0.0035 (9)0.0009 (9)
C20.0451 (11)0.0516 (13)0.0528 (12)0.0020 (10)0.0029 (10)0.0047 (11)
C30.0458 (13)0.0838 (19)0.0640 (15)0.0004 (12)0.0018 (11)0.0035 (14)
C40.0553 (15)0.101 (2)0.087 (2)0.0032 (15)0.0154 (15)0.0028 (18)
C50.0381 (13)0.091 (2)0.116 (3)0.0000 (13)0.0038 (15)0.005 (2)
C60.0500 (14)0.0738 (19)0.090 (2)0.0047 (13)0.0174 (14)0.0081 (16)
C70.0485 (12)0.0513 (14)0.0673 (15)0.0053 (10)0.0132 (11)0.0071 (12)
C80.0644 (16)0.0688 (17)0.0543 (13)0.0093 (13)0.0190 (12)0.0073 (12)
C90.0662 (15)0.0746 (18)0.0424 (11)0.0086 (13)0.0081 (11)0.0022 (12)
C100.0504 (12)0.0585 (14)0.0444 (11)0.0042 (10)0.0018 (9)0.0021 (10)
C110.0442 (11)0.0569 (14)0.0413 (10)0.0013 (9)0.0005 (9)0.0016 (10)
C120.0447 (11)0.0569 (14)0.0378 (10)0.0019 (9)0.0003 (8)0.0013 (10)
C130.0435 (11)0.0726 (16)0.0432 (11)0.0011 (10)0.0010 (9)0.0052 (11)
C140.0486 (13)0.102 (2)0.0505 (13)0.0009 (13)0.0074 (11)0.0089 (14)
C150.0577 (14)0.101 (2)0.0428 (12)0.0007 (14)0.0074 (11)0.0055 (13)
C160.091 (2)0.147 (3)0.0446 (14)0.017 (2)0.0099 (14)0.0047 (18)
C170.109 (3)0.137 (3)0.0577 (17)0.005 (2)0.0232 (17)0.011 (2)
C180.086 (2)0.121 (3)0.084 (2)0.008 (2)0.0430 (18)0.014 (2)
C190.0621 (19)0.157 (4)0.102 (3)0.001 (2)0.0229 (18)0.015 (3)
C200.0498 (16)0.177 (4)0.082 (2)0.008 (2)0.0145 (15)0.027 (2)
C210.0475 (13)0.097 (2)0.0490 (13)0.0010 (13)0.0024 (11)0.0069 (13)
C220.0480 (12)0.0530 (13)0.0457 (11)0.0017 (10)0.0027 (9)0.0044 (10)
C230.0476 (12)0.0535 (13)0.0511 (12)0.0008 (10)0.0028 (10)0.0020 (11)
C240.0524 (14)0.0793 (18)0.0587 (14)0.0019 (12)0.0005 (11)0.0054 (13)
C250.0558 (15)0.091 (2)0.0816 (19)0.0042 (14)0.0106 (14)0.0116 (17)
C260.0463 (14)0.083 (2)0.101 (2)0.0052 (13)0.0027 (15)0.0004 (18)
C270.0543 (15)0.0727 (18)0.0826 (19)0.0016 (13)0.0186 (14)0.0064 (15)
C280.0542 (13)0.0544 (14)0.0584 (13)0.0011 (11)0.0112 (11)0.0046 (11)
C290.0654 (16)0.0699 (17)0.0512 (13)0.0060 (13)0.0144 (11)0.0074 (12)
C300.0710 (16)0.0732 (17)0.0424 (11)0.0082 (13)0.0028 (11)0.0042 (12)
C310.0523 (13)0.0619 (15)0.0463 (12)0.0036 (11)0.0012 (10)0.0037 (11)
C320.0486 (12)0.0598 (14)0.0441 (11)0.0012 (10)0.0005 (9)0.0043 (10)
C330.0463 (12)0.0581 (14)0.0422 (11)0.0008 (10)0.0015 (9)0.0038 (10)
C340.0461 (11)0.0604 (14)0.0434 (11)0.0004 (10)0.0031 (9)0.0021 (10)
C350.0450 (12)0.0667 (15)0.0460 (11)0.0010 (10)0.0003 (9)0.0011 (11)
C360.0508 (13)0.0720 (16)0.0462 (12)0.0018 (11)0.0014 (10)0.0043 (11)
C370.0730 (18)0.113 (3)0.0492 (14)0.0037 (17)0.0027 (13)0.0168 (15)
C380.102 (2)0.130 (3)0.0482 (15)0.006 (2)0.0155 (16)0.0017 (17)
C390.0742 (19)0.101 (2)0.0699 (18)0.0038 (17)0.0273 (15)0.0072 (17)
C400.0606 (16)0.090 (2)0.083 (2)0.0038 (15)0.0208 (14)0.0045 (17)
C410.0473 (13)0.095 (2)0.0639 (15)0.0006 (13)0.0045 (12)0.0006 (15)
C420.0485 (13)0.093 (2)0.0461 (12)0.0072 (13)0.0028 (10)0.0027 (13)
Geometric parameters (Å, º) top
S1—C121.720 (2)C18—H18A0.9700
S1—C151.726 (3)C18—H18B0.9700
S2—C331.719 (2)C19—C201.456 (5)
S2—C361.729 (2)C19—H19A0.9700
O1—C101.350 (3)C19—H19B0.9700
O1—H1O0.82 (3)C20—H20A0.9700
O2—C311.343 (3)C20—H20B0.9700
O2—H2O0.82 (3)C22—C311.400 (3)
N1—C111.292 (3)C22—C321.436 (3)
N1—C121.380 (3)C22—C231.445 (3)
N2—C211.135 (3)C23—C241.412 (3)
N3—C321.290 (3)C23—C281.420 (3)
N3—C331.385 (3)C24—C251.368 (4)
N4—C421.137 (3)C24—H240.9300
C1—C101.398 (3)C25—C261.391 (4)
C1—C111.435 (3)C25—H250.9300
C1—C21.439 (3)C26—C271.356 (4)
C2—C31.411 (3)C26—H260.9300
C2—C71.420 (3)C27—C281.408 (4)
C3—C41.368 (4)C27—H270.9300
C3—H30.9300C28—C291.420 (4)
C4—C51.403 (4)C29—C301.349 (4)
C4—H40.9300C29—H290.9300
C5—C61.343 (4)C30—C311.410 (3)
C5—H50.9300C30—H300.9300
C6—C71.410 (4)C32—H320.9300
C6—H60.9300C33—C341.373 (3)
C7—C81.413 (4)C34—C351.430 (3)
C8—C91.346 (4)C34—C421.432 (3)
C8—H80.9300C35—C361.359 (3)
C9—C101.403 (3)C35—C411.507 (3)
C9—H90.9300C36—C371.505 (3)
C11—H110.9300C37—C381.495 (5)
C12—C131.368 (3)C37—H37A0.9700
C13—C141.421 (3)C37—H37B0.9700
C13—C211.428 (3)C38—C391.522 (5)
C14—C151.358 (4)C38—H38A0.9700
C14—C201.511 (4)C38—H38B0.9700
C15—C161.513 (3)C39—C401.501 (4)
C16—C171.457 (5)C39—H39A0.9700
C16—H16A0.9700C39—H39B0.9700
C16—H16B0.9700C40—C411.500 (4)
C17—C181.522 (5)C40—H40A0.9700
C17—H17A0.9700C40—H40B0.9700
C17—H17B0.9700C41—H41A0.9700
C18—C191.511 (5)C41—H41B0.9700
C12—S1—C1591.95 (11)C14—C20—H20B108.2
C33—S2—C3692.41 (11)H20A—C20—H20B107.4
C10—O1—H1O108 (2)N2—C21—C13178.8 (4)
C31—O2—H2O106 (2)C31—C22—C32120.4 (2)
C11—N1—C12121.09 (19)C31—C22—C23118.5 (2)
C32—N3—C33121.3 (2)C32—C22—C23121.0 (2)
C10—C1—C11120.3 (2)C24—C23—C28117.3 (2)
C10—C1—C2118.7 (2)C24—C23—C22123.5 (2)
C11—C1—C2121.0 (2)C28—C23—C22119.2 (2)
C3—C2—C7117.5 (2)C25—C24—C23121.1 (3)
C3—C2—C1123.7 (2)C25—C24—H24119.5
C7—C2—C1118.8 (2)C23—C24—H24119.5
C4—C3—C2121.1 (3)C24—C25—C26121.2 (3)
C4—C3—H3119.4C24—C25—H25119.4
C2—C3—H3119.4C26—C25—H25119.4
C3—C4—C5120.6 (3)C27—C26—C25119.3 (3)
C3—C4—H4119.7C27—C26—H26120.3
C5—C4—H4119.7C25—C26—H26120.3
C6—C5—C4119.9 (3)C26—C27—C28121.4 (3)
C6—C5—H5120.0C26—C27—H27119.3
C4—C5—H5120.0C28—C27—H27119.3
C5—C6—C7121.3 (3)C27—C28—C23119.7 (2)
C5—C6—H6119.3C27—C28—C29121.3 (2)
C7—C6—H6119.3C23—C28—C29118.9 (2)
C6—C7—C8121.1 (2)C30—C29—C28122.0 (2)
C6—C7—C2119.6 (3)C30—C29—H29119.0
C8—C7—C2119.3 (2)C28—C29—H29119.0
C9—C8—C7121.8 (2)C29—C30—C31120.0 (2)
C9—C8—H8119.1C29—C30—H30120.0
C7—C8—H8119.1C31—C30—H30120.0
C8—C9—C10120.2 (2)O2—C31—C22122.3 (2)
C8—C9—H9119.9O2—C31—C30116.4 (2)
C10—C9—H9119.9C22—C31—C30121.3 (2)
O1—C10—C1122.3 (2)N3—C32—C22122.5 (2)
O1—C10—C9116.5 (2)N3—C32—H32118.8
C1—C10—C9121.2 (2)C22—C32—H32118.8
N1—C11—C1122.6 (2)C34—C33—N3124.3 (2)
N1—C11—H11118.7C34—C33—S2109.85 (17)
C1—C11—H11118.7N3—C33—S2125.82 (17)
C13—C12—N1124.44 (19)C33—C34—C35114.5 (2)
C13—C12—S1110.22 (16)C33—C34—C42121.3 (2)
N1—C12—S1125.31 (16)C35—C34—C42124.2 (2)
C12—C13—C14114.3 (2)C36—C35—C34111.1 (2)
C12—C13—C21121.6 (2)C36—C35—C41126.1 (2)
C14—C13—C21124.1 (2)C34—C35—C41122.7 (2)
C15—C14—C13111.3 (2)C35—C36—C37130.1 (2)
C15—C14—C20125.0 (3)C35—C36—S2112.13 (18)
C13—C14—C20123.5 (2)C37—C36—S2117.67 (19)
C14—C15—C16129.1 (3)C38—C37—C36115.8 (3)
C14—C15—S1112.15 (18)C38—C37—H37A108.3
C16—C15—S1118.6 (2)C36—C37—H37A108.3
C17—C16—C15115.8 (3)C38—C37—H37B108.3
C17—C16—H16A108.3C36—C37—H37B108.3
C15—C16—H16A108.3H37A—C37—H37B107.4
C17—C16—H16B108.3C37—C38—C39116.0 (3)
C15—C16—H16B108.3C37—C38—H38A108.3
H16A—C16—H16B107.4C39—C38—H38A108.3
C16—C17—C18117.1 (3)C37—C38—H38B108.3
C16—C17—H17A108.0C39—C38—H38B108.3
C18—C17—H17A108.0H38A—C38—H38B107.4
C16—C17—H17B108.0C40—C39—C38114.5 (2)
C18—C17—H17B108.0C40—C39—H39A108.6
H17A—C17—H17B107.3C38—C39—H39A108.6
C19—C18—C17115.7 (3)C40—C39—H39B108.6
C19—C18—H18A108.3C38—C39—H39B108.6
C17—C18—H18A108.3H39A—C39—H39B107.6
C19—C18—H18B108.3C41—C40—C39117.8 (3)
C17—C18—H18B108.3C41—C40—H40A107.8
H18A—C18—H18B107.4C39—C40—H40A107.8
C20—C19—C18116.8 (4)C41—C40—H40B107.8
C20—C19—H19A108.1C39—C40—H40B107.8
C18—C19—H19A108.1H40A—C40—H40B107.2
C20—C19—H19B108.1C40—C41—C35117.2 (2)
C18—C19—H19B108.1C40—C41—H41A108.0
H19A—C19—H19B107.3C35—C41—H41A108.0
C19—C20—C14116.3 (3)C40—C41—H41B108.0
C19—C20—H20A108.2C35—C41—H41B108.0
C14—C20—H20A108.2H41A—C41—H41B107.2
C19—C20—H20B108.2N4—C42—C34178.7 (4)
C10—C1—C2—C3179.8 (2)C31—C22—C23—C24177.8 (2)
C11—C1—C2—C31.0 (4)C32—C22—C23—C244.0 (4)
C10—C1—C2—C70.5 (3)C31—C22—C23—C281.4 (4)
C11—C1—C2—C7178.3 (2)C32—C22—C23—C28176.8 (2)
C7—C2—C3—C40.0 (4)C28—C23—C24—C251.0 (4)
C1—C2—C3—C4179.3 (3)C22—C23—C24—C25179.8 (3)
C2—C3—C4—C50.4 (5)C23—C24—C25—C260.7 (5)
C3—C4—C5—C60.5 (5)C24—C25—C26—C270.3 (5)
C4—C5—C6—C70.2 (5)C25—C26—C27—C280.2 (5)
C5—C6—C7—C8179.5 (3)C26—C27—C28—C230.4 (4)
C5—C6—C7—C20.2 (4)C26—C27—C28—C29179.7 (3)
C3—C2—C7—C60.3 (4)C24—C23—C28—C270.8 (4)
C1—C2—C7—C6179.7 (2)C22—C23—C28—C27179.9 (2)
C3—C2—C7—C8179.5 (2)C24—C23—C28—C29179.9 (2)
C1—C2—C7—C80.1 (4)C22—C23—C28—C290.6 (4)
C6—C7—C8—C9179.9 (3)C27—C28—C29—C30178.9 (3)
C2—C7—C8—C90.1 (4)C23—C28—C29—C301.8 (4)
C7—C8—C9—C100.1 (4)C28—C29—C30—C310.9 (4)
C11—C1—C10—O11.1 (4)C32—C22—C31—O23.0 (4)
C2—C1—C10—O1179.9 (2)C23—C22—C31—O2178.8 (2)
C11—C1—C10—C9178.1 (2)C32—C22—C31—C30175.8 (2)
C2—C1—C10—C90.8 (4)C23—C22—C31—C302.4 (4)
C8—C9—C10—O1179.8 (2)C29—C30—C31—O2179.9 (2)
C8—C9—C10—C10.6 (4)C29—C30—C31—C221.3 (4)
C12—N1—C11—C1179.2 (2)C33—N3—C32—C22177.8 (2)
C10—C1—C11—N11.4 (4)C31—C22—C32—N31.2 (4)
C2—C1—C11—N1177.5 (2)C23—C22—C32—N3179.3 (2)
C11—N1—C12—C13178.9 (2)C32—N3—C33—C34178.7 (2)
C11—N1—C12—S13.1 (3)C32—N3—C33—S21.7 (3)
C15—S1—C12—C131.5 (2)C36—S2—C33—C340.2 (2)
C15—S1—C12—N1176.7 (2)C36—S2—C33—N3179.8 (2)
N1—C12—C13—C14177.1 (2)N3—C33—C34—C35179.7 (2)
S1—C12—C13—C141.1 (3)S2—C33—C34—C350.1 (3)
N1—C12—C13—C212.2 (4)N3—C33—C34—C421.2 (4)
S1—C12—C13—C21179.5 (2)S2—C33—C34—C42179.2 (2)
C12—C13—C14—C150.1 (4)C33—C34—C35—C360.2 (3)
C21—C13—C14—C15179.3 (3)C42—C34—C35—C36178.9 (3)
C12—C13—C14—C20176.0 (3)C33—C34—C35—C41177.8 (2)
C21—C13—C14—C203.4 (5)C42—C34—C35—C411.3 (4)
C13—C14—C15—C16174.5 (3)C34—C35—C36—C37175.1 (3)
C20—C14—C15—C161.3 (6)C41—C35—C36—C372.5 (5)
C13—C14—C15—S11.3 (4)C34—C35—C36—S20.3 (3)
C20—C14—C15—S1177.1 (3)C41—C35—C36—S2177.9 (2)
C12—S1—C15—C141.6 (3)C33—S2—C36—C350.3 (2)
C12—S1—C15—C16174.6 (3)C33—S2—C36—C37175.7 (2)
C14—C15—C16—C1748.8 (6)C35—C36—C37—C3847.0 (5)
S1—C15—C16—C17135.7 (3)S2—C36—C37—C38137.9 (3)
C15—C16—C17—C1866.1 (5)C36—C37—C38—C3966.9 (4)
C16—C17—C18—C1967.5 (5)C37—C38—C39—C4071.3 (4)
C17—C18—C19—C2069.4 (5)C38—C39—C40—C4171.0 (4)
C18—C19—C20—C1470.2 (5)C39—C40—C41—C3565.8 (4)
C15—C14—C20—C1948.6 (6)C36—C35—C41—C4042.6 (4)
C13—C14—C20—C19136.1 (4)C34—C35—C41—C40140.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···N10.82 (3)1.84 (3)2.578 (2)150 (3)
O2—H2O···N30.82 (3)1.84 (3)2.582 (2)151 (3)

Experimental details

Crystal data
Chemical formulaC21H18N2OS
Mr346.43
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)296
a, b, c (Å)13.5472 (2), 14.4747 (4), 35.7902 (6)
V3)7018.2 (2)
Z16
Radiation typeCu Kα
µ (mm1)1.71
Crystal size (mm)0.37 × 0.21 × 0.14
Data collection
DiffractometerAgilent SuperNova (Dual, Cu at zero, Atlas, CCD)
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2012)
Tmin, Tmax0.858, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
28490, 7066, 5288
Rint0.035
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.161, 1.02
No. of reflections7066
No. of parameters457
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.52, 0.25

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), WinGX (Farrugia, 2012) and X-SEED (Barbour, 2001).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···N10.82 (3)1.84 (3)2.578 (2)150 (3)
O2—H2O···N30.82 (3)1.84 (3)2.582 (2)151 (3)
 

Acknowledgements

The authors would like to thank the Deanship of Scientific Research at King Abdulaziz University for the support of this research via Research Group Track grant No. 3–102/428.

References

First citationAgilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
First citationAsiri, A. M., Khan, S. A. & Tahir, M. N. (2011a). Acta Cryst. E67, o2254.  Web of Science CSD CrossRef IUCr Journals
First citationAsiri, A. M., Khan, S. A. & Tahir, M. N. (2011b). Acta Cryst. E67, o2355.  Web of Science CSD CrossRef IUCr Journals
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS
First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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