PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): o2484–o2485.
Published online 2010 September 4. doi:  10.1107/S1600536810034434
PMCID: PMC2983394

6-Amino-5-(1-amino-2,2-dicyano­vin­yl)-3,3a,4,5-tetra­hydro-2H-indene-4-spiro-1′-cyclo­pentane-3a,7-dicarbonitrile–thio­phene-2-carbaldehyde (1/0.5)

Abstract

In each of the two independent indene-4-spiro­pentane mol­ecules in the asymmetric unit of the title 2:1 adduct, C19H18N6·0.5C5H4OS, the cyclo­hexene ring adopts a half-chair conformation and the cyclo­pentene and cyclo­pentane rings adopt envelope conformations. The mean plane through the cyclo­hexene/cyclo­pentene fused system is aligned at a dihedral angle of 77.9 (1)° with respect to the mean plane through the cyclo­pentane ring in one mol­ecule and 87.0 (1)° in the other. In the crystal, adjacent indene-4-spiro­pentane mol­ecules are linked by N—H(...)N hydrogen bonds into a three-dimensional network. The spaces within the network are occupied by the thio­phene-2-carbaldehyde mol­ecules. The thio­phene-2-carbaldehyde unit is disordered over two positions of equal occupancy. The crystal studied was found to be a non-morohedral twin with two minor twin components of 18.4 and 9.7%.

Related literature

For our report of the condensation of cyclopentylidene­malono­nitrile and thiophene-2-carbaldehyde to form 2,5-bis(thienylidene)-1-dicyanomethylene-cyclopentane, a purple-colored compound suitable for application as a dye, see: Asiri (2003 [triangle]). For a related structure, see: Nesterov & Viltchinskaia (2000 [triangle]). For the treatment of twinned diffraction data, see: Spek (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2484-scheme1.jpg

Experimental

Crystal data

  • C19H18N6·0.5C5H4OS
  • M r = 386.46
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2484-efi1.jpg
  • a = 12.0181 (14) Å
  • b = 13.8109 (15) Å
  • c = 13.9000 (15) Å
  • α = 60.703 (1)°
  • β = 77.841 (2)°
  • γ = 89.879 (2)°
  • V = 1953.1 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.14 mm−1
  • T = 100 K
  • 0.45 × 0.05 × 0.05 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.942, T max = 0.993
  • 18784 measured reflections
  • 8916 independent reflections
  • 5141 reflections with I > 2σ(I)
  • R int = 0.068

Refinement

  • R[F 2 > 2σ(F 2)] = 0.074
  • wR(F 2) = 0.216
  • S = 1.02
  • 8916 reflections
  • 571 parameters
  • 94 restraints
  • H-atom parameters constrained
  • Δρmax = 0.59 e Å−3
  • Δρmin = −0.50 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034434/xu5020sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034434/xu5020Isup2.hkl

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

Acknowledgments

We thank King Abdul Aziz University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

We have previously reported the condensation of cyclopentylidenemalononitrile and thiophene-2-carbaldehyde to form 2,5-bis(thienylidene)-1-dicyanomethylene-cyclopentane, a purple-colored compound suitable for application as a dye (Asiri, 2003). For reasons that we are not clear of, our attempted synthesis gave only colorless crystals. We examined a plate-like specimen and identified it as 6-amino-5,5,7-tricyano-3,3a,4,5- tetrahydro-2H-indene-4-spirocyclo-pentane, whose structure has already been reported (Nesterov & Viltchinskaia, 2000). We identified a prismatic specimen as the title 1: 0.5 co-crystal (Scheme I, Fig. 1); the second component is unchanged thiophene-2-carbaldehyde. The first component differs from the reported compound in having an aminodicyanovinyl group (along with a methine hydrogen) in place of the two cyano groups in the 5-position. Additionally, the compound has another cyano group in the 3a position.

Experimental

Cyclopentylidenemalononitrile (0.13 g, 1 mmol) and thiophene-2-carbaldehyde (0.22 g, 2 mmol) were heated in an oil bath for 6 h. Ethanol was added to break up the solid material. The product was collected and recrystallized from acetic acid.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C). The amino H-atoms were similarly positioned (N–H 0.86 Å) by rotating them; their temperature factors were tied by a factor of 1.2. Modeling the amino group as if it was a methyl group but setting the occupancy factor of one of the three H-atoms to zero gave a satisfactory hydrogen bond scheme except for the H2n2 and H3n2 atoms, which were 1.82 Å apart.

The thiophene-2-carbaldehyde molecule is disordered over two positions; as the disorder refined to nearly 1:1, the occupancy of each component was set to 0.5. The sulfur–carbon distances were restrained to 1.70±0.01 Å and the oxygen–carbon distances to 1.25±0.01 Å. The excyclic carbon–carbon distances were restrained to 1.50±0.01 Å and the endocyclic ones to 1.35±0.01 Å. All atoms of each component were restrained to lie on a plane. The temperature factors of C41' were set to those of S1, and that of S1' to those of C41 as the pair of atoms are close to each other. The anisotropic temperature factors of the disordered atoms were restrained to be nearly isotropic. The primed carbon atoms were set to those of the unprimed ones; the anisotropic temperature factors of these carbon atoms were restrained to be nearly isotropic.

The structure is a non-meohedrally twinned structure with two minor twin components of 18.5 and 9.7%. The twin domains were identified by the use of PLATON (Spek, 2009). The twinned nature led to a somewhat large weighting scheme.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of the asymmetric unit of the C19H18N6.0.5C5H4OS co-crystal at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C19H18N6·0.5C5H4OSV = 1953.1 (4) Å3
Mr = 386.46Z = 4
Triclinic, P1F(000) = 812
Hall symbol: -P 1Dx = 1.314 Mg m3
a = 12.0181 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.8109 (15) ŵ = 0.14 mm1
c = 13.9000 (15) ÅT = 100 K
α = 60.703 (1)°Prism, colorless
β = 77.841 (2)°0.45 × 0.05 × 0.05 mm
γ = 89.879 (2)°

Data collection

Bruker SMART APEX diffractometer8916 independent reflections
Radiation source: fine-focus sealed tube5141 reflections with I > 2σ(I)
graphiteRint = 0.068
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −15→15
Tmin = 0.942, Tmax = 0.993k = −17→17
18784 measured reflectionsl = −18→18

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)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.216H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.1073P)2 + 0.3194P] where P = (Fo2 + 2Fc2)/3
8916 reflections(Δ/σ)max = 0.001
571 parametersΔρmax = 0.59 e Å3
94 restraintsΔρmin = −0.50 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
N10.4315 (3)0.5673 (3)0.3804 (3)0.0226 (7)
N20.3308 (2)0.4683 (2)0.6776 (3)0.0185 (7)
H2N10.38820.47250.62620.022*
H2N20.29920.40020.71940.022*
N30.0952 (2)0.3434 (2)0.8014 (3)0.0188 (7)
H3N10.08900.28270.86520.023*
H3N20.15120.34340.75140.023*
N40.0331 (3)0.2262 (2)1.0946 (3)0.0251 (7)
N50.1735 (3)0.5862 (3)0.9363 (3)0.0265 (8)
N60.2511 (3)0.8177 (2)0.5964 (3)0.0208 (7)
N70.1317 (3)1.0660 (3)0.3768 (3)0.0232 (7)
N80.0847 (2)0.9640 (2)0.6749 (3)0.0166 (6)
H8N10.07000.94390.62880.020*
H8N20.08940.90570.73720.020*
N90.2564 (2)0.8396 (2)0.8127 (3)0.0167 (6)
H9N10.21180.78200.86780.020*
H9N20.24890.84750.74910.020*
N100.1724 (3)0.7429 (3)1.1069 (3)0.0308 (8)
N110.1138 (3)1.0999 (3)0.9271 (3)0.0283 (8)
N120.2061 (3)1.3168 (2)0.5990 (3)0.0199 (7)
C10.1173 (3)0.7121 (3)0.5405 (3)0.0138 (7)
C20.0404 (3)0.7911 (3)0.4653 (3)0.0182 (8)
H2A−0.03680.75150.48570.022*
H2B0.03230.85730.47510.022*
C30.1023 (3)0.8262 (3)0.3422 (3)0.0247 (9)
H3A0.04730.82450.29900.030*
H3B0.14410.90230.30280.030*
C40.1835 (3)0.7411 (3)0.3552 (3)0.0195 (8)
H40.22380.73200.29410.023*
C50.1931 (3)0.6794 (3)0.4618 (3)0.0135 (7)
C60.2654 (3)0.5934 (3)0.5125 (3)0.0133 (7)
C70.2539 (3)0.5343 (3)0.6275 (3)0.0139 (7)
C80.1539 (3)0.5441 (3)0.7069 (3)0.0141 (7)
H80.18630.59190.73230.017*
C90.0552 (3)0.6065 (3)0.6523 (3)0.0149 (7)
C10−0.0223 (3)0.5370 (3)0.6247 (3)0.0162 (7)
H10A−0.01120.57050.54160.019*
H10B−0.00360.45900.65670.019*
C11−0.1455 (3)0.5403 (3)0.6799 (3)0.0286 (9)
H11A−0.17880.60420.62590.034*
H11B−0.19410.47020.70570.034*
C12−0.1362 (4)0.5532 (4)0.7792 (4)0.0334 (10)
H12A−0.12850.48070.84450.040*
H12B−0.20410.58390.80330.040*
C13−0.0279 (3)0.6350 (3)0.7332 (3)0.0173 (8)
H13A0.00570.62580.79600.021*
H13B−0.04530.71310.69180.021*
C140.1147 (3)0.4307 (3)0.8139 (3)0.0150 (7)
C150.1041 (3)0.4207 (3)0.9191 (3)0.0168 (8)
C160.0647 (3)0.3143 (3)1.0194 (3)0.0202 (8)
C170.1406 (3)0.5114 (3)0.9310 (3)0.0195 (8)
C180.3565 (3)0.5790 (3)0.4394 (3)0.0157 (7)
C190.1922 (3)0.7745 (3)0.5698 (3)0.0159 (7)
C200.3623 (3)1.2092 (3)0.5421 (3)0.0133 (7)
C210.4758 (3)1.2877 (3)0.4679 (3)0.0180 (8)
H21A0.48081.35170.48100.022*
H21B0.54301.24660.48560.022*
C220.4708 (3)1.3282 (3)0.3445 (3)0.0255 (9)
H22A0.44751.40440.30880.031*
H22B0.54621.32840.29870.031*
C230.3825 (3)1.2450 (3)0.3546 (3)0.0202 (8)
H230.37011.23940.29210.024*
C240.3239 (3)1.1801 (3)0.4614 (3)0.0146 (7)
C250.2275 (3)1.0928 (3)0.5128 (3)0.0134 (7)
C260.1841 (3)1.0304 (3)0.6278 (3)0.0127 (7)
C270.2436 (3)1.0412 (3)0.7085 (3)0.0122 (7)
H270.20031.09240.73000.015*
C280.3695 (3)1.0996 (3)0.6531 (3)0.0129 (7)
C290.4198 (3)1.1257 (3)0.7329 (3)0.0163 (7)
H29A0.42151.20630.70820.020*
H29B0.37311.08220.81200.020*
C300.5411 (3)1.0923 (3)0.7248 (4)0.0271 (9)
H30A0.59631.15390.65960.033*
H30B0.56581.07140.79540.033*
C310.5307 (3)0.9926 (3)0.7078 (4)0.0279 (9)
H31A0.49470.92440.78030.033*
H31B0.60670.97880.67580.033*
C320.4547 (3)1.0274 (3)0.6243 (3)0.0167 (8)
H32A0.41280.96080.63310.020*
H32B0.50131.07140.54520.020*
C330.2289 (3)0.9305 (3)0.8186 (3)0.0127 (7)
C340.1865 (3)0.9270 (3)0.9199 (3)0.0165 (8)
C350.1772 (3)0.8260 (3)1.0245 (3)0.0206 (8)
C360.1474 (3)1.0222 (3)0.9246 (3)0.0193 (8)
C370.1739 (3)1.0779 (3)0.4380 (3)0.0162 (7)
C380.2760 (3)1.2720 (3)0.5729 (3)0.0150 (7)
S10.5191 (4)0.2016 (3)0.9487 (3)0.0527 (7)0.50
O10.3269 (6)0.0090 (5)1.0456 (5)0.0475 (17)0.50
C390.3016 (8)0.0856 (6)1.0644 (6)0.038 (2)0.50
H390.22640.08021.10670.046*0.50
C400.3831 (6)0.1866 (7)1.0241 (5)0.038 (2)0.50
C410.3604 (14)0.2732 (10)1.0424 (10)0.0546 (8)0.50
H410.28870.27821.08330.066*0.50
C420.4531 (9)0.3522 (9)0.9949 (8)0.065 (3)0.50
H420.45360.41910.99870.078*0.50
C430.5438 (10)0.3246 (6)0.9423 (7)0.054 (3)0.50
H430.61540.37040.90480.064*0.50
S1'0.3563 (4)0.2909 (3)1.0178 (3)0.0546 (8)0.50
O1'0.5647 (7)0.4697 (6)0.9167 (6)0.072 (2)0.50
C39'0.5830 (9)0.3837 (7)0.9125 (7)0.053 (3)0.50
H39'0.65860.37870.87890.063*0.50
C40'0.4948 (6)0.2880 (8)0.9564 (5)0.041 (3)0.50
C41'0.5067 (14)0.1919 (10)0.9553 (9)0.0527 (7)0.50
H41'0.57760.17580.92430.063*0.50
C42'0.4095 (8)0.1200 (8)1.0020 (7)0.044 (2)0.50
H42'0.40420.04861.00780.053*0.50
C43'0.3215 (9)0.1629 (7)1.0391 (6)0.051 (3)0.50
H43'0.24620.12431.07440.061*0.50

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0205 (16)0.0246 (16)0.0219 (19)0.0060 (13)−0.0030 (14)−0.0118 (15)
N20.0155 (15)0.0125 (14)0.0216 (18)0.0030 (11)−0.0023 (13)−0.0048 (13)
N30.0218 (16)0.0111 (14)0.0191 (18)0.0012 (11)−0.0015 (13)−0.0054 (13)
N40.0316 (18)0.0172 (16)0.0164 (18)−0.0003 (13)−0.0026 (14)−0.0019 (14)
N50.040 (2)0.0175 (16)0.0218 (19)0.0057 (14)−0.0104 (15)−0.0088 (14)
N60.0261 (17)0.0133 (14)0.0215 (18)0.0028 (12)−0.0055 (14)−0.0077 (14)
N70.0260 (17)0.0238 (16)0.0239 (19)0.0025 (13)−0.0096 (14)−0.0136 (15)
N80.0219 (15)0.0101 (13)0.0157 (17)0.0016 (11)−0.0090 (13)−0.0032 (12)
N90.0236 (16)0.0116 (13)0.0129 (16)0.0024 (11)−0.0070 (13)−0.0035 (12)
N100.044 (2)0.0232 (17)0.021 (2)0.0066 (15)−0.0112 (16)−0.0067 (16)
N110.041 (2)0.0181 (16)0.0217 (19)0.0016 (14)−0.0001 (15)−0.0093 (15)
N120.0275 (17)0.0113 (14)0.0208 (18)0.0018 (12)−0.0070 (14)−0.0074 (13)
C10.0172 (16)0.0097 (15)0.0162 (19)0.0040 (12)−0.0050 (14)−0.0075 (14)
C20.0199 (18)0.0136 (16)0.020 (2)0.0069 (13)−0.0064 (15)−0.0068 (15)
C30.032 (2)0.0210 (19)0.018 (2)0.0074 (16)−0.0072 (17)−0.0074 (17)
C40.0238 (19)0.0185 (17)0.015 (2)0.0029 (14)−0.0045 (15)−0.0073 (16)
C50.0164 (16)0.0097 (15)0.0152 (19)0.0023 (12)−0.0046 (14)−0.0065 (14)
C60.0151 (16)0.0092 (15)0.0140 (19)0.0028 (12)−0.0038 (14)−0.0045 (14)
C70.0159 (16)0.0080 (15)0.017 (2)0.0014 (12)−0.0044 (14)−0.0055 (14)
C80.0177 (17)0.0118 (15)0.0130 (19)0.0021 (13)−0.0034 (14)−0.0064 (14)
C90.0178 (17)0.0109 (15)0.0147 (19)0.0039 (13)−0.0057 (14)−0.0047 (14)
C100.0205 (18)0.0126 (16)0.018 (2)0.0042 (13)−0.0078 (15)−0.0081 (15)
C110.0220 (19)0.034 (2)0.027 (2)−0.0009 (17)−0.0042 (17)−0.0133 (19)
C120.028 (2)0.038 (2)0.033 (3)−0.0014 (18)0.0011 (19)−0.021 (2)
C130.0214 (18)0.0168 (17)0.016 (2)0.0073 (14)−0.0045 (15)−0.0105 (15)
C140.0116 (16)0.0140 (16)0.018 (2)0.0035 (12)−0.0030 (14)−0.0071 (15)
C150.0217 (18)0.0112 (16)0.016 (2)0.0033 (13)−0.0061 (15)−0.0047 (15)
C160.0219 (19)0.0192 (18)0.021 (2)0.0046 (15)−0.0031 (16)−0.0114 (17)
C170.0229 (19)0.0200 (18)0.016 (2)0.0070 (15)−0.0034 (15)−0.0103 (16)
C180.0185 (17)0.0107 (15)0.0159 (19)0.0019 (13)−0.0052 (15)−0.0048 (14)
C190.0197 (17)0.0080 (15)0.015 (2)0.0033 (13)−0.0008 (14)−0.0039 (14)
C200.0166 (16)0.0078 (14)0.0142 (19)0.0010 (12)−0.0061 (14)−0.0036 (14)
C210.0202 (18)0.0141 (16)0.017 (2)−0.0029 (13)−0.0049 (15)−0.0054 (15)
C220.032 (2)0.0214 (19)0.014 (2)−0.0091 (16)0.0002 (16)−0.0038 (16)
C230.0273 (19)0.0185 (18)0.014 (2)−0.0028 (15)−0.0043 (15)−0.0073 (16)
C240.0173 (17)0.0136 (16)0.0158 (19)0.0019 (13)−0.0047 (14)−0.0093 (15)
C250.0166 (16)0.0105 (15)0.0159 (19)0.0023 (13)−0.0070 (14)−0.0076 (14)
C260.0150 (16)0.0087 (15)0.0161 (19)0.0054 (12)−0.0071 (14)−0.0063 (14)
C270.0159 (16)0.0080 (14)0.0109 (18)0.0023 (12)−0.0046 (13)−0.0029 (14)
C280.0177 (17)0.0083 (15)0.0122 (18)0.0006 (12)−0.0046 (14)−0.0042 (14)
C290.0191 (17)0.0159 (17)0.0139 (19)0.0000 (13)−0.0068 (14)−0.0065 (15)
C300.024 (2)0.028 (2)0.034 (2)0.0049 (16)−0.0169 (18)−0.0156 (19)
C310.028 (2)0.025 (2)0.036 (3)0.0131 (16)−0.0181 (19)−0.0155 (19)
C320.0166 (17)0.0118 (16)0.019 (2)0.0024 (13)−0.0056 (15)−0.0050 (15)
C330.0142 (16)0.0095 (15)0.0110 (18)−0.0011 (12)−0.0047 (13)−0.0019 (14)
C340.0224 (18)0.0137 (16)0.0127 (19)−0.0012 (13)−0.0056 (15)−0.0054 (15)
C350.029 (2)0.0166 (18)0.019 (2)0.0004 (15)−0.0079 (16)−0.0096 (17)
C360.0255 (19)0.0165 (17)0.0100 (19)−0.0024 (14)−0.0007 (15)−0.0036 (15)
C370.0202 (17)0.0107 (15)0.0155 (19)0.0021 (13)−0.0051 (15)−0.0045 (14)
C380.0218 (18)0.0091 (15)0.016 (2)0.0005 (13)−0.0096 (15)−0.0061 (15)
S10.0638 (17)0.0479 (14)0.0463 (14)0.0097 (11)−0.0051 (12)−0.0267 (11)
O10.060 (4)0.040 (3)0.054 (4)0.014 (3)−0.027 (3)−0.026 (3)
C390.041 (5)0.043 (5)0.032 (5)0.007 (4)−0.020 (4)−0.016 (4)
C400.050 (6)0.035 (5)0.038 (5)0.011 (4)−0.021 (4)−0.021 (4)
C410.0418 (12)0.0609 (18)0.077 (2)0.0194 (12)−0.0207 (14)−0.0436 (17)
C420.070 (7)0.052 (6)0.083 (7)0.003 (5)−0.023 (6)−0.040 (5)
C430.051 (7)0.044 (6)0.062 (7)−0.014 (5)−0.001 (5)−0.029 (5)
S1'0.0418 (12)0.0609 (18)0.077 (2)0.0194 (12)−0.0207 (14)−0.0436 (17)
O1'0.074 (5)0.054 (4)0.080 (5)0.013 (4)−0.010 (4)−0.031 (4)
C39'0.047 (6)0.053 (6)0.056 (6)0.019 (5)−0.016 (5)−0.023 (5)
C40'0.039 (5)0.042 (5)0.037 (5)0.008 (4)−0.014 (4)−0.015 (4)
C41'0.0638 (17)0.0479 (14)0.0463 (14)0.0097 (11)−0.0051 (12)−0.0267 (11)
C42'0.058 (6)0.050 (5)0.034 (5)0.007 (4)−0.021 (4)−0.024 (4)
C43'0.057 (6)0.050 (6)0.055 (6)0.010 (5)−0.027 (5)−0.029 (5)

Geometric parameters (Å, °)

N1—C181.152 (4)C20—C241.515 (5)
N2—C71.349 (4)C20—C211.555 (4)
N2—H2N10.8600C20—C281.565 (4)
N2—H2N20.8600C21—C221.538 (5)
N3—C141.327 (4)C21—H21A0.9900
N3—H3N10.8600C21—H21B0.9900
N3—H3N20.8600C22—C231.499 (5)
N4—C161.144 (4)C22—H22A0.9900
N5—C171.148 (4)C22—H22B0.9900
N6—C191.149 (4)C23—C241.328 (5)
N7—C371.152 (4)C23—H230.9500
N8—C261.336 (4)C24—C251.456 (4)
N8—H8N10.8600C25—C261.369 (5)
N8—H8N20.8600C25—C371.425 (5)
N9—C331.335 (4)C26—C271.514 (5)
N9—H9N10.8600C27—C331.519 (4)
N9—H9N20.8600C27—C281.562 (4)
N10—C351.148 (5)C27—H271.0000
N11—C361.159 (5)C28—C291.550 (5)
N12—C381.145 (4)C28—C321.554 (5)
C1—C191.490 (5)C29—C301.526 (5)
C1—C51.514 (5)C29—H29A0.9900
C1—C91.548 (4)C29—H29B0.9900
C1—C21.557 (5)C30—C311.516 (5)
C2—C31.539 (5)C30—H30A0.9900
C2—H2A0.9900C30—H30B0.9900
C2—H2B0.9900C31—C321.520 (5)
C3—C41.492 (5)C31—H31A0.9900
C3—H3A0.9900C31—H31B0.9900
C3—H3B0.9900C32—H32A0.9900
C4—C51.332 (5)C32—H32B0.9900
C4—H40.9500C33—C341.370 (5)
C5—C61.447 (5)C34—C351.421 (5)
C6—C71.368 (5)C34—C361.422 (5)
C6—C181.414 (5)S1—C431.681 (8)
C7—C81.505 (5)S1—C401.698 (8)
C8—C141.522 (4)O1—C391.231 (8)
C8—C91.569 (5)C39—C401.492 (8)
C8—H81.0000C39—H390.9500
C9—C131.542 (5)C40—C411.355 (10)
C9—C101.564 (4)C41—C421.364 (10)
C10—C111.530 (5)C41—H410.9500
C10—H10A0.9900C42—C431.343 (9)
C10—H10B0.9900C42—H420.9500
C11—C121.502 (6)C43—H430.9500
C11—H11A0.9900S1'—C43'1.682 (8)
C11—H11B0.9900S1'—C40'1.714 (8)
C12—C131.526 (5)O1'—C39'1.234 (8)
C12—H12A0.9900C39'—C40'1.479 (8)
C12—H12B0.9900C39'—H39'0.9500
C13—H13A0.9900C40'—C41'1.340 (10)
C13—H13B0.9900C41'—C42'1.351 (10)
C14—C151.378 (5)C41'—H41'0.9500
C15—C171.423 (5)C42'—C43'1.342 (9)
C15—C161.430 (5)C42'—H42'0.9500
C20—C381.478 (5)C43'—H43'0.9500
C7—N2—H2N1109.5C20—C21—H21B110.7
C7—N2—H2N2109.5H21A—C21—H21B108.8
H2N1—N2—H2N2109.5C23—C22—C21104.2 (3)
C14—N3—H3N1109.5C23—C22—H22A110.9
C14—N3—H3N2109.5C21—C22—H22A110.9
H3N1—N3—H3N2109.5C23—C22—H22B110.9
C26—N8—H8N1109.5C21—C22—H22B110.9
C26—N8—H8N2109.5H22A—C22—H22B108.9
H8N1—N8—H8N2109.5C24—C23—C22111.9 (3)
C33—N9—H9N1109.5C24—C23—H23124.1
C33—N9—H9N2109.5C22—C23—H23124.1
H9N1—N9—H9N2109.5C23—C24—C25132.4 (3)
C19—C1—C5107.9 (3)C23—C24—C20112.1 (3)
C19—C1—C9107.8 (3)C25—C24—C20115.4 (3)
C5—C1—C9110.4 (3)C26—C25—C37119.9 (3)
C19—C1—C2110.7 (3)C26—C25—C24122.7 (3)
C5—C1—C2103.0 (3)C37—C25—C24117.3 (3)
C9—C1—C2116.8 (3)N8—C26—C25123.0 (3)
C3—C2—C1105.4 (3)N8—C26—C27116.3 (3)
C3—C2—H2A110.7C25—C26—C27120.5 (3)
C1—C2—H2A110.7C26—C27—C33110.9 (3)
C3—C2—H2B110.7C26—C27—C28114.1 (3)
C1—C2—H2B110.7C33—C27—C28114.6 (3)
H2A—C2—H2B108.8C26—C27—H27105.4
C4—C3—C2103.9 (3)C33—C27—H27105.4
C4—C3—H3A111.0C28—C27—H27105.4
C2—C3—H3A111.0C29—C28—C32104.7 (3)
C4—C3—H3B111.0C29—C28—C27112.1 (3)
C2—C3—H3B111.0C32—C28—C27113.7 (2)
H3A—C3—H3B109.0C29—C28—C20111.3 (2)
C5—C4—C3112.5 (3)C32—C28—C20110.4 (3)
C5—C4—H4123.8C27—C28—C20104.8 (3)
C3—C4—H4123.8C30—C29—C28105.8 (3)
C4—C5—C6131.9 (3)C30—C29—H29A110.6
C4—C5—C1111.7 (3)C28—C29—H29A110.6
C6—C5—C1116.2 (3)C30—C29—H29B110.6
C7—C6—C18119.9 (3)C28—C29—H29B110.6
C7—C6—C5121.5 (3)H29A—C29—H29B108.7
C18—C6—C5118.2 (3)C31—C30—C29103.4 (3)
N2—C7—C6123.9 (3)C31—C30—H30A111.1
N2—C7—C8115.4 (3)C29—C30—H30A111.1
C6—C7—C8120.6 (3)C31—C30—H30B111.1
C7—C8—C14109.5 (3)C29—C30—H30B111.1
C7—C8—C9116.0 (3)H30A—C30—H30B109.0
C14—C8—C9114.8 (3)C30—C31—C32103.3 (3)
C7—C8—H8105.1C30—C31—H31A111.1
C14—C8—H8105.1C32—C31—H31A111.1
C9—C8—H8105.1C30—C31—H31B111.1
C13—C9—C1112.5 (3)C32—C31—H31B111.1
C13—C9—C10104.9 (3)H31A—C31—H31B109.1
C1—C9—C10109.4 (3)C31—C32—C28105.9 (3)
C13—C9—C8111.2 (3)C31—C32—H32A110.6
C1—C9—C8104.7 (3)C28—C32—H32A110.6
C10—C9—C8114.3 (3)C31—C32—H32B110.6
C11—C10—C9105.6 (3)C28—C32—H32B110.6
C11—C10—H10A110.6H32A—C32—H32B108.7
C9—C10—H10A110.6N9—C33—C34122.3 (3)
C11—C10—H10B110.6N9—C33—C27118.5 (3)
C9—C10—H10B110.6C34—C33—C27119.2 (3)
H10A—C10—H10B108.8C33—C34—C35120.5 (3)
C12—C11—C10104.8 (3)C33—C34—C36121.7 (3)
C12—C11—H11A110.8C35—C34—C36117.8 (3)
C10—C11—H11A110.8N10—C35—C34177.5 (4)
C12—C11—H11B110.8N11—C36—C34178.6 (4)
C10—C11—H11B110.8N7—C37—C25179.3 (4)
H11A—C11—H11B108.9N12—C38—C20177.2 (3)
C11—C12—C13103.6 (3)C43—S1—C4089.2 (5)
C11—C12—H12A111.0O1—C39—C40123.4 (9)
C13—C12—H12A111.0O1—C39—H39118.3
C11—C12—H12B111.0C40—C39—H39118.3
C13—C12—H12B111.0C41—C40—C39126.1 (9)
H12A—C12—H12B109.0C41—C40—S1113.0 (9)
C12—C13—C9105.6 (3)C39—C40—S1120.9 (7)
C12—C13—H13A110.6C40—C41—C42111.7 (13)
C9—C13—H13A110.6C40—C41—H41124.1
C12—C13—H13B110.6C42—C41—H41124.1
C9—C13—H13B110.6C43—C42—C41112.2 (12)
H13A—C13—H13B108.8C43—C42—H42123.9
N3—C14—C15122.2 (3)C41—C42—H42123.9
N3—C14—C8117.8 (3)C42—C43—S1113.9 (8)
C15—C14—C8119.9 (3)C42—C43—H43123.1
C14—C15—C17121.6 (3)S1—C43—H43123.1
C14—C15—C16119.6 (3)C43'—S1'—C40'89.4 (5)
C17—C15—C16118.6 (3)O1'—C39'—C40'124.3 (10)
N4—C16—C15175.1 (4)O1'—C39'—H39'117.9
N5—C17—C15177.1 (4)C40'—C39'—H39'117.9
N1—C18—C6179.4 (4)C41'—C40'—C39'128.4 (9)
N6—C19—C1176.7 (4)C41'—C40'—S1'111.0 (10)
C38—C20—C24108.4 (3)C39'—C40'—S1'120.6 (8)
C38—C20—C21109.8 (3)C40'—C41'—C42'114.6 (14)
C24—C20—C21102.9 (3)C40'—C41'—H41'122.7
C38—C20—C28108.4 (3)C42'—C41'—H41'122.7
C24—C20—C28109.8 (2)C43'—C42'—C41'110.9 (12)
C21—C20—C28117.2 (3)C43'—C42'—H42'124.5
C22—C21—C20105.1 (3)C41'—C42'—H42'124.5
C22—C21—H21A110.7C42'—C43'—S1'114.1 (9)
C20—C21—H21A110.7C42'—C43'—H43'123.0
C22—C21—H21B110.7S1'—C43'—H43'123.0
C19—C1—C2—C397.7 (3)C38—C20—C24—C25−72.8 (3)
C5—C1—C2—C3−17.4 (3)C21—C20—C24—C25170.9 (3)
C9—C1—C2—C3−138.5 (3)C28—C20—C24—C2545.5 (4)
C1—C2—C3—C418.0 (3)C23—C24—C25—C26175.6 (4)
C2—C3—C4—C5−12.2 (4)C20—C24—C25—C26−8.6 (5)
C3—C4—C5—C6−175.7 (3)C23—C24—C25—C37−7.9 (6)
C3—C4—C5—C10.8 (4)C20—C24—C25—C37167.9 (3)
C19—C1—C5—C4−106.3 (3)C37—C25—C26—N8−8.1 (5)
C9—C1—C5—C4136.1 (3)C24—C25—C26—N8168.3 (3)
C2—C1—C5—C410.7 (4)C37—C25—C26—C27176.9 (3)
C19—C1—C5—C670.8 (3)C24—C25—C26—C27−6.6 (5)
C9—C1—C5—C6−46.8 (4)N8—C26—C27—C3337.1 (4)
C2—C1—C5—C6−172.1 (3)C25—C26—C27—C33−147.6 (3)
C4—C5—C6—C7−174.7 (3)N8—C26—C27—C28168.3 (3)
C1—C5—C6—C78.9 (4)C25—C26—C27—C28−16.4 (4)
C4—C5—C6—C1811.5 (5)C26—C27—C28—C29170.8 (3)
C1—C5—C6—C18−164.9 (3)C33—C27—C28—C29−59.8 (4)
C18—C6—C7—N26.0 (5)C26—C27—C28—C32−70.7 (4)
C5—C6—C7—N2−167.6 (3)C33—C27—C28—C3258.7 (4)
C18—C6—C7—C8−176.8 (3)C26—C27—C28—C2049.9 (3)
C5—C6—C7—C89.5 (4)C33—C27—C28—C20179.3 (3)
N2—C7—C8—C14−39.7 (4)C38—C20—C28—C29−67.2 (3)
C6—C7—C8—C14142.9 (3)C24—C20—C28—C29174.5 (3)
N2—C7—C8—C9−171.6 (3)C21—C20—C28—C2957.7 (4)
C6—C7—C8—C911.0 (4)C38—C20—C28—C32177.0 (2)
C19—C1—C9—C1365.2 (3)C24—C20—C28—C3258.7 (3)
C5—C1—C9—C13−177.2 (3)C21—C20—C28—C32−58.1 (4)
C2—C1—C9—C13−60.1 (4)C38—C20—C28—C2754.2 (3)
C19—C1—C9—C10−178.6 (3)C24—C20—C28—C27−64.1 (3)
C5—C1—C9—C10−61.0 (3)C21—C20—C28—C27179.1 (3)
C2—C1—C9—C1056.1 (4)C32—C28—C29—C3012.5 (3)
C19—C1—C9—C8−55.7 (3)C27—C28—C29—C30136.3 (3)
C5—C1—C9—C861.9 (3)C20—C28—C29—C30−106.7 (3)
C2—C1—C9—C8179.0 (3)C28—C29—C30—C31−33.5 (4)
C7—C8—C9—C13−167.1 (3)C29—C30—C31—C3241.6 (4)
C14—C8—C9—C1363.5 (3)C30—C31—C32—C28−33.9 (4)
C7—C8—C9—C1−45.3 (3)C29—C28—C32—C3113.1 (3)
C14—C8—C9—C1−174.7 (3)C27—C28—C32—C31−109.6 (3)
C7—C8—C9—C1074.4 (3)C20—C28—C32—C31133.0 (3)
C14—C8—C9—C10−55.0 (4)C26—C27—C33—N952.2 (4)
C13—C9—C10—C116.0 (4)C28—C27—C33—N9−78.8 (4)
C1—C9—C10—C11−114.9 (3)C26—C27—C33—C34−126.9 (3)
C8—C9—C10—C11128.0 (3)C28—C27—C33—C34102.1 (4)
C9—C10—C11—C12−28.3 (4)N9—C33—C34—C354.2 (5)
C10—C11—C12—C1339.6 (4)C27—C33—C34—C35−176.8 (3)
C11—C12—C13—C9−35.8 (4)N9—C33—C34—C36−173.9 (3)
C1—C9—C13—C12136.9 (3)C27—C33—C34—C365.1 (5)
C10—C9—C13—C1218.0 (4)C28—C20—C38—N12−52 (8)
C8—C9—C13—C12−106.0 (3)O1—C39—C40—C41−179.8 (2)
C7—C8—C14—N3−50.7 (4)O1—C39—C40—S1−0.3 (3)
C9—C8—C14—N381.8 (4)C43—S1—C40—C41−0.2 (2)
C7—C8—C14—C15127.3 (3)C43—S1—C40—C39−179.7 (2)
C9—C8—C14—C15−100.2 (4)C39—C40—C41—C42179.7 (2)
N3—C14—C15—C17171.0 (3)S1—C40—C41—C420.2 (3)
C8—C14—C15—C17−6.9 (5)C40—C41—C42—C43−0.2 (4)
N3—C14—C15—C16−3.5 (5)C41—C42—C43—S10.1 (4)
C8—C14—C15—C16178.5 (3)C40—S1—C43—C420.1 (2)
C38—C20—C21—C22−96.4 (3)O1'—C39'—C40'—C41'179.9 (2)
C24—C20—C21—C2218.8 (4)O1'—C39'—C40'—S1'0.2 (3)
C28—C20—C21—C22139.4 (3)C43'—S1'—C40'—C41'0.1 (2)
C20—C21—C22—C23−18.8 (4)C43'—S1'—C40'—C39'179.8 (2)
C21—C22—C23—C2412.0 (4)C39'—C40'—C41'—C42'−179.9 (2)
C22—C23—C24—C25176.3 (4)S1'—C40'—C41'—C42'−0.2 (4)
C22—C23—C24—C200.4 (4)C40'—C41'—C42'—C43'0.2 (4)
C38—C20—C24—C23103.8 (3)C41'—C42'—C43'—S1'−0.1 (3)
C21—C20—C24—C23−12.4 (4)C40'—S1'—C43'—C42'0.0 (2)
C28—C20—C24—C23−137.9 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2n1···N1i0.862.232.909 (4)136
N3—H3n1···N11ii0.862.282.970 (4)138
N3—H3n2···N12ii0.862.293.042 (4)147
N8—H8n1···N7iii0.862.452.921 (4)115
N8—H8n2···N4iv0.862.313.006 (4)138
N9—H9n1···N50.862.393.098 (4)139
N9—H9n2···N60.862.353.178 (4)163

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y−1, z; (iii) −x, −y+2, −z+1; (iv) −x, −y+1, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5020).

References

  • Asiri, A. M. (2003). Bull. Korean Chem. Soc.24, 426–430.
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Nesterov, V. N. & Viltchinskaia, E. A. (2000). Acta Cryst. C56, 872–873. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography