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Acta Cryst. (2007). E63, o3910
https://doi.org/10.1107/S1600536807041621
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7,7-Dimethyl-5-phenyl-10-(2-thien­yl)-7,8-dihydro-5H-indeno[1,2-b]quinoline-9,11(6H,10H)-dione dimethyl­formamide hemisolvate

W. Zhu, C. Li and Y. Xiang
The asymmetric unit of the title compound, C28H23NO2S·0.5C3H7NO, contains two 7,7-dimethyl-5-phenyl-10-(2-thien­yl)-7,8-dihydro-5H-indeno[1,2-b]quinoline-9,11(6H,10H)-dione mol­ecules and one dimethyl­formamide solvent mol­ecule. The two thio­phene rings are disordered over two positions each; site-occupancy factors range from 0.457 (6) to 0.543 (6). The two dihydro­pyridine rings adopt boat conformations, while the two cyclo­hexene rings have envelope conformations.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041621/hk2311sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041621/hk2311Isup2.hkl
Contains datablock I

CCDC reference: 662428

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.007 Å
  • Disorder in main residue
  • R factor = 0.067
  • wR factor = 0.216
  • Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found




Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         45 Perc.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.76 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C27
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        S2'
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C54
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C25
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C53
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N3
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C57
PLAT301_ALERT_3_C Main Residue  Disorder .........................       6.00 Perc.
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........         O5
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C27    -   C28    ...       1.30 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C55    -   C56    ...       1.32 Ang.


   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  18 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

1,4-Dihydropyridines (1,4-DHPs) are well known compounds because of their pharmacological profiles as calcium channel modulators (Stout & Meyers, 1982). With a 1,4-DHP parent nucleus, indenoquinoline belongs to a class of compounds which are special not only because of their interesting chemical and physical properties, but also due to their immense utility in the pharmaceutical industries. The discovery of indenoquinoline, as new potent cytotoxic and antitumor agents, has attracted the attention of organic chemists (Yamato et al., 1989; Deady et al., 2000; Chen et al., 2002). It is well established that the chemical modifications on the indenoquinoline skeletons may bring remarkable changes of biological activity (Deady et al., 1999). We report herein the crystal structure of the title compound, (I).

The asymmetric unit of the title compound, (I), contains two C28H23NO2S molecules and one dimethylformamide (C3H7NO) molecule (Fig. 1). The bond lengths and angles are generally within normal ranges (Allen et al., 1987).

When the crystal structure was solved,the atoms S1, S2, C26, H26, C54 and H54 were found to be disordered. So, for instance, the positions of C26 and C54 atoms may be occupied by S1 and S2 atoms, respectively. In fact, it may not be possible to separate S atoms from C atoms, and that is the reason why the C—S bonds are longer than C═C bonds, but shorter than normal C—S single bonds.

Rings A (C1—C6), B (N1/C1/C6—C8/C16), A' (C29—C34) and B' (N2/C29/C34—C36/C44) are not planar, having total puckering amplitudes, QT, of 0.467 (3), 0.278 (2), 0.456 (3) and 0.231 (3) Å, respectively. Rings B and B' adopt boat conformations [φ = -59.19 (3)°, θ = 110.20 (3)° and φ = -118.31 (2)°, θ = 69.55 (3)°, respectively] (Cremer & Pople, 1975). Rings A and A' have envelope conformations with atoms C3 and C31 displaced by 0.639 (3) Å and -0.622 (2) Å from the planes of the other ring atoms, respectively. Rings C (C10—C15), D (C8—C10/C15/C16), E (C17—C22), F (C25—C28/S1) and C' (C38—C43), D' (C36—C38/C43/C44), E' (C45—C50) and F' (C53—C55/S2) are, of course, planar and rings C, D and C', D' are also coplanar with dihedral angles of 0.97 (3)° and 0.58 (3)°, respectively.

Related literature top

For related literature, see: Stout & Meyers (1982); Yamato et al. (1989); Deady et al. (1999, 2000); Chen et al. (2002); Tu et al. (2006). For general background, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound, (I), was prepared by the reaction of thiophene-2 -carbaldehyde (110 mg, 1 mmol), 5,5-dimethyl-3-(phenylamino)cyclohex-2-enone (220 mg, 1 mmol) with 1,3-indanedione (150 mg, 1 mmol) in acetic acid (1.5 ml) under microwave irradiation for 4 min at 200 W power and 393 K (microwave oven is EmrysTM Creator from Personal Chemistry, Uppsala, Sweden). Upon completion, monitored by TLC, the reaction mixture was cooled to room temperature and then poured into cold water. The solid product was filtered, washed with water and EtOH (95%), and subsequently dried and recrystallized from EtOH (95%) to give the pure product. Single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of a 95% aqueous ethanol solution (yield; 370 mg, 85%; m.p. 503–505 K).

Refinement top

When the crystal structure was solved,the atoms S1, S2, C26, H26, C54 and H54 were found to be disordered. During refinement with isotropic thermal parameters, the occupancies of disordered H atoms were refined as H26 = 0.543 (6), H26' = 0.457 (6), H54 = 0.476 (7) and H54' = 0.524 (7). The remaining site occupancy factors were also refined as S1 = 0.543 (6), S1' = 0.457 (6), S2 = 0.476 (7), S2' = 0.524 (7), C26 = 0.543 (6), C26' = 0.457 (6), C54 = 0.476 (7) and C54' = 0.524 (7), during anisotropic refinement. H atoms were positioned geometrically with C—H = 0.93, 0.98, 0.97 and 0.96 Å for aromatic, methine, methylene and methyl H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

Structure description top

1,4-Dihydropyridines (1,4-DHPs) are well known compounds because of their pharmacological profiles as calcium channel modulators (Stout & Meyers, 1982). With a 1,4-DHP parent nucleus, indenoquinoline belongs to a class of compounds which are special not only because of their interesting chemical and physical properties, but also due to their immense utility in the pharmaceutical industries. The discovery of indenoquinoline, as new potent cytotoxic and antitumor agents, has attracted the attention of organic chemists (Yamato et al., 1989; Deady et al., 2000; Chen et al., 2002). It is well established that the chemical modifications on the indenoquinoline skeletons may bring remarkable changes of biological activity (Deady et al., 1999). We report herein the crystal structure of the title compound, (I).

The asymmetric unit of the title compound, (I), contains two C28H23NO2S molecules and one dimethylformamide (C3H7NO) molecule (Fig. 1). The bond lengths and angles are generally within normal ranges (Allen et al., 1987).

When the crystal structure was solved,the atoms S1, S2, C26, H26, C54 and H54 were found to be disordered. So, for instance, the positions of C26 and C54 atoms may be occupied by S1 and S2 atoms, respectively. In fact, it may not be possible to separate S atoms from C atoms, and that is the reason why the C—S bonds are longer than C═C bonds, but shorter than normal C—S single bonds.

Rings A (C1—C6), B (N1/C1/C6—C8/C16), A' (C29—C34) and B' (N2/C29/C34—C36/C44) are not planar, having total puckering amplitudes, QT, of 0.467 (3), 0.278 (2), 0.456 (3) and 0.231 (3) Å, respectively. Rings B and B' adopt boat conformations [φ = -59.19 (3)°, θ = 110.20 (3)° and φ = -118.31 (2)°, θ = 69.55 (3)°, respectively] (Cremer & Pople, 1975). Rings A and A' have envelope conformations with atoms C3 and C31 displaced by 0.639 (3) Å and -0.622 (2) Å from the planes of the other ring atoms, respectively. Rings C (C10—C15), D (C8—C10/C15/C16), E (C17—C22), F (C25—C28/S1) and C' (C38—C43), D' (C36—C38/C43/C44), E' (C45—C50) and F' (C53—C55/S2) are, of course, planar and rings C, D and C', D' are also coplanar with dihedral angles of 0.97 (3)° and 0.58 (3)°, respectively.

For related literature, see: Stout & Meyers (1982); Yamato et al. (1989); Deady et al. (1999, 2000); Chen et al. (2002); Tu et al. (2006). For general background, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms are omitted for clarity.
7,7-Dimethyl-5-phenyl-10-(2-thienyl)-7,8-dihydro-5H-indeno[1,2-b]quinoline-9,11(6H,10H)-dione dimethylformamide hemisolvate top
Crystal data top
C28H23NO2S·0.5C3H7NOF(000) = 2000
Mr = 474.08Dx = 1.261 Mg m−3
Monoclinic, P21/cMelting point = 503–505 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 15.081 (2) ÅCell parameters from 3416 reflections
b = 9.4381 (14) Åθ = 2.2–20.7°
c = 35.102 (3) ŵ = 0.16 mm−1
β = 92.041 (3)°T = 298 K
V = 4992.9 (11) Å3Block, red
Z = 80.43 × 0.32 × 0.28 mm
Data collection top
Bruker CCD area-detector
diffractometer		8790 independent reflections
Radiation source: fine-focus sealed tube3935 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
φ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −17→17
Tmin = 0.934, Tmax = 0.957k = −11→11
25441 measured reflectionsl = −41→41
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)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.216H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0388P)2 + 5.7834P]
where P = (Fo2 + 2Fc2)/3
8790 reflections(Δ/σ)max = 0.001
636 parametersΔρmax = 0.47 e Å−3
0 restraintsΔρmin = −0.38 e Å−3
Crystal data top
C28H23NO2S·0.5C3H7NOV = 4992.9 (11) Å3
Mr = 474.08Z = 8
Monoclinic, P21/cMo Kα radiation
a = 15.081 (2) ŵ = 0.16 mm−1
b = 9.4381 (14) ÅT = 298 K
c = 35.102 (3) Å0.43 × 0.32 × 0.28 mm
β = 92.041 (3)°
Data collection top
Bruker CCD area-detector
diffractometer		8790 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3935 reflections with I > 2σ(I)
Tmin = 0.934, Tmax = 0.957Rint = 0.058
25441 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0670 restraints
wR(F2) = 0.216H-atom parameters constrained
S = 1.00Δρmax = 0.47 e Å−3
8790 reflectionsΔρmin = −0.38 e Å−3
636 parameters
Special details top

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) top
xyzUiso*/UeqOcc. (<1)
N10.6520 (2)0.8962 (4)0.18639 (9)0.0471 (9)
O10.5219 (2)1.1267 (4)0.28990 (10)0.0831 (11)
O20.8552 (2)0.8958 (4)0.29221 (10)0.0787 (10)
S10.7025 (6)1.2602 (12)0.2105 (2)0.0685 (15)0.543 (6)
S1'0.8025 (4)1.2516 (13)0.2777 (3)0.0926 (19)0.457 (6)
C10.5801 (3)0.9650 (4)0.20350 (11)0.0446 (10)
C20.4947 (3)0.9692 (5)0.18048 (12)0.0530 (12)
H2A0.46770.87590.18080.064*
H2B0.50740.99120.15420.064*
C30.4284 (3)1.0774 (5)0.19476 (14)0.0585 (12)
C40.4248 (3)1.0620 (6)0.23788 (13)0.0679 (14)
H4A0.38571.13420.24750.082*
H4B0.39960.97040.24370.082*
C50.5135 (3)1.0749 (5)0.25804 (14)0.0564 (12)
C60.5905 (3)1.0203 (4)0.23887 (12)0.0459 (11)
C70.6800 (3)1.0348 (5)0.25897 (12)0.0498 (11)
H70.67401.02220.28650.060*
C80.7389 (3)0.9208 (5)0.24394 (12)0.0490 (11)
C90.8224 (3)0.8699 (5)0.26047 (14)0.0564 (12)
C100.8621 (3)0.7786 (5)0.23056 (13)0.0544 (12)
C110.9410 (3)0.7068 (6)0.23092 (16)0.0706 (15)
H110.97900.70870.25240.085*
C120.9632 (3)0.6312 (6)0.19881 (18)0.0786 (17)
H121.01700.58300.19840.094*
C130.9065 (3)0.6274 (6)0.16784 (16)0.0738 (16)
H130.92200.57520.14660.089*
C140.8258 (3)0.6994 (5)0.16693 (13)0.0599 (13)
H140.78760.69530.14560.072*
C150.8040 (3)0.7768 (4)0.19858 (13)0.0498 (11)
C160.7269 (3)0.8678 (4)0.20865 (12)0.0445 (10)
C170.6483 (3)0.8550 (5)0.14690 (11)0.0474 (11)
C180.6921 (3)0.9378 (5)0.12114 (13)0.0623 (13)
H180.71961.02130.12920.075*
C190.6952 (4)0.8976 (7)0.08379 (15)0.0793 (17)
H190.72490.95280.06640.095*
C200.6540 (4)0.7749 (8)0.07245 (15)0.0832 (18)
H200.65670.74610.04720.100*
C210.6089 (4)0.6938 (6)0.09748 (16)0.0785 (16)
H210.58020.61180.08910.094*
C220.6059 (3)0.7337 (5)0.13550 (13)0.0610 (13)
H220.57550.67900.15280.073*
C230.3377 (3)1.0490 (6)0.17598 (17)0.0883 (18)
H23A0.34111.05930.14890.132*
H23B0.29551.11540.18540.132*
H23C0.31930.95440.18180.132*
C240.4563 (3)1.2286 (5)0.18438 (16)0.0802 (16)
H24A0.45871.23700.15720.120*
H24B0.51371.24840.19580.120*
H24C0.41391.29480.19370.120*
C250.7215 (3)1.1783 (5)0.25128 (13)0.0554 (12)
C260.7775 (17)1.261 (4)0.2764 (13)0.0926 (19)0.543 (6)
H260.78941.24420.30220.111*0.543 (6)
C26'0.712 (3)1.265 (5)0.2174 (12)0.0685 (15)0.457 (6)
H26'0.67441.24400.19670.082*0.457 (6)
S20.2967 (4)−0.0878 (10)0.0720 (3)0.0936 (17)0.476 (7)
S2'0.4021 (4)0.0998 (7)0.0333 (2)0.1040 (18)0.524 (7)
N20.0808 (2)0.1273 (4)0.08187 (9)0.0493 (9)
O30.2963 (2)0.3737 (4)0.01357 (9)0.0806 (11)
O40.1601 (2)−0.1504 (4)−0.02383 (9)0.0763 (10)
C270.8141 (5)1.3828 (8)0.2523 (3)0.123 (3)
H270.86011.44350.25980.148*
C280.7699 (4)1.3866 (7)0.2198 (2)0.098 (2)
H280.77731.46030.20260.117*
C290.1360 (3)0.2450 (4)0.07598 (11)0.0442 (10)
C300.1206 (3)0.3714 (5)0.10037 (12)0.0542 (12)
H30A0.11280.33980.12630.065*
H30B0.06590.41680.09160.065*
C310.1951 (3)0.4805 (5)0.10045 (12)0.0559 (12)
C320.2206 (4)0.5062 (5)0.05950 (13)0.0661 (14)
H32A0.17190.55370.04590.079*
H32B0.27160.56880.05950.079*
C330.2422 (3)0.3727 (5)0.03884 (12)0.0572 (12)
C340.1954 (3)0.2432 (5)0.04826 (11)0.0460 (10)
C350.2177 (3)0.1104 (5)0.02597 (13)0.0569 (12)
H350.22570.1364−0.00070.068*
C360.1408 (3)0.0124 (5)0.02794 (11)0.0486 (11)
C370.1215 (3)−0.1105 (5)0.00424 (13)0.0556 (12)
C380.0437 (3)−0.1811 (5)0.02148 (13)0.0539 (12)
C39−0.0007 (3)−0.3029 (5)0.01027 (14)0.0662 (14)
H390.0160−0.3534−0.01110.079*
C40−0.0705 (3)−0.3475 (5)0.03154 (16)0.0699 (14)
H40−0.1008−0.43000.02480.084*
C41−0.0953 (3)−0.2719 (6)0.06239 (15)0.0683 (14)
H41−0.1424−0.30420.07640.082*
C42−0.0524 (3)−0.1487 (5)0.07346 (14)0.0619 (13)
H42−0.0713−0.09720.09420.074*
C430.0185 (3)−0.1034 (5)0.05336 (12)0.0498 (11)
C440.0815 (3)0.0184 (4)0.05583 (11)0.0458 (11)
C450.0243 (3)0.1215 (5)0.11418 (11)0.0468 (11)
C46−0.0549 (3)0.1942 (5)0.11302 (13)0.0583 (12)
H46−0.07190.24740.09170.070*
C47−0.1084 (3)0.1871 (6)0.14389 (15)0.0687 (14)
H47−0.16160.23710.14370.082*
C48−0.0838 (4)0.1068 (6)0.17489 (16)0.0767 (16)
H48−0.12020.10260.19570.092*
C49−0.0059 (4)0.0328 (6)0.17558 (14)0.0773 (16)
H490.0099−0.02320.19650.093*
C500.0495 (3)0.0413 (5)0.14496 (13)0.0608 (13)
H500.1033−0.00710.14540.073*
C510.1621 (4)0.6175 (5)0.11844 (14)0.0810 (16)
H51A0.14670.59950.14430.121*
H51B0.11080.65120.10420.121*
H51C0.20810.68780.11810.121*
C520.2756 (3)0.4261 (6)0.12348 (14)0.0776 (16)
H52A0.25960.40960.14930.116*
H52B0.32220.49530.12310.116*
H52C0.29570.33910.11250.116*
C530.3016 (3)0.0397 (5)0.04134 (14)0.0641 (13)
C540.391 (2)0.056 (3)0.0365 (10)0.1040 (18)0.476 (7)
H540.41150.12320.01960.125*0.476 (7)
C54'0.3161 (18)−0.075 (4)0.0645 (9)0.0936 (17)0.524 (7)
H54'0.2679−0.12570.07300.112*0.524 (7)
C550.4506 (4)−0.0278 (8)0.0567 (2)0.105 (2)
H550.5122−0.02350.05710.126*
C560.4000 (4)−0.1158 (7)0.07549 (19)0.098 (2)
H560.4238−0.19000.09000.117*
N30.6516 (7)0.3356 (7)0.0652 (2)0.135 (3)
O50.7733 (7)0.4293 (9)0.0982 (3)0.244 (5)
C570.7339 (10)0.3999 (12)0.0655 (3)0.162 (4)
H570.76070.42190.04280.194*
C580.6104 (8)0.3013 (9)0.0998 (3)0.200 (5)
H58A0.55410.25710.09420.300*
H58B0.60160.38630.11420.300*
H58C0.64770.23740.11440.300*
C590.6157 (7)0.3105 (10)0.0280 (3)0.182 (4)
H59A0.55890.26550.02950.273*
H59B0.65500.25010.01440.273*
H59C0.60890.39900.01470.273*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.044 (2)0.053 (2)0.045 (2)0.0089 (18)0.0081 (17)0.0009 (17)
N20.049 (2)0.049 (2)0.050 (2)0.0016 (19)0.0102 (17)−0.0059 (18)
N30.190 (8)0.088 (5)0.130 (6)−0.009 (5)0.038 (6)0.000 (4)
O10.089 (3)0.091 (3)0.072 (2)0.002 (2)0.026 (2)−0.025 (2)
O20.073 (2)0.091 (3)0.071 (2)0.004 (2)−0.010 (2)0.008 (2)
O30.100 (3)0.074 (3)0.070 (2)−0.009 (2)0.037 (2)−0.0011 (18)
O40.082 (2)0.083 (3)0.064 (2)0.013 (2)0.0086 (19)−0.0265 (19)
O50.287 (10)0.195 (8)0.243 (9)0.078 (7)−0.096 (8)−0.033 (7)
S10.069 (3)0.0574 (16)0.080 (3)−0.0026 (15)0.022 (2)0.012 (2)
S20.063 (3)0.102 (3)0.117 (4)0.010 (3)0.008 (2)0.033 (3)
C26'0.069 (3)0.0574 (16)0.080 (3)−0.0026 (15)0.022 (2)0.012 (2)
C54'0.063 (3)0.102 (3)0.117 (4)0.010 (3)0.008 (2)0.033 (3)
C10.042 (2)0.043 (3)0.049 (3)0.004 (2)0.010 (2)0.004 (2)
C20.047 (3)0.052 (3)0.060 (3)0.009 (2)0.004 (2)−0.006 (2)
C30.041 (3)0.059 (3)0.076 (3)0.011 (2)0.006 (2)0.001 (2)
C40.048 (3)0.077 (4)0.081 (4)0.006 (3)0.023 (3)−0.007 (3)
C50.057 (3)0.052 (3)0.061 (3)−0.003 (2)0.021 (2)−0.005 (2)
C60.044 (2)0.045 (3)0.050 (3)−0.001 (2)0.011 (2)0.002 (2)
C70.056 (3)0.051 (3)0.043 (2)−0.003 (2)0.007 (2)0.003 (2)
C80.050 (3)0.044 (3)0.052 (3)−0.001 (2)0.003 (2)0.005 (2)
C90.054 (3)0.055 (3)0.060 (3)−0.003 (2)0.001 (2)0.016 (2)
C100.045 (3)0.052 (3)0.066 (3)0.002 (2)0.004 (2)0.019 (2)
C110.051 (3)0.078 (4)0.084 (4)0.008 (3)0.005 (3)0.030 (3)
C120.057 (3)0.083 (4)0.098 (4)0.026 (3)0.028 (3)0.030 (3)
C130.063 (3)0.076 (4)0.084 (4)0.026 (3)0.023 (3)0.019 (3)
C140.054 (3)0.061 (3)0.065 (3)0.017 (3)0.009 (2)0.012 (2)
C150.047 (3)0.043 (3)0.060 (3)0.010 (2)0.016 (2)0.012 (2)
C160.043 (2)0.039 (3)0.052 (3)0.003 (2)0.006 (2)0.007 (2)
C170.044 (2)0.054 (3)0.044 (2)0.011 (2)0.007 (2)0.002 (2)
C180.060 (3)0.072 (4)0.055 (3)0.007 (3)0.012 (2)0.008 (3)
C190.080 (4)0.103 (5)0.056 (3)0.024 (4)0.019 (3)0.013 (3)
C200.086 (4)0.116 (6)0.048 (3)0.038 (4)0.006 (3)−0.006 (3)
C210.086 (4)0.074 (4)0.075 (4)0.014 (3)0.004 (3)−0.025 (3)
C220.064 (3)0.059 (3)0.061 (3)0.006 (3)0.012 (2)−0.003 (3)
C230.056 (3)0.095 (5)0.115 (5)0.015 (3)0.005 (3)−0.015 (4)
C240.072 (4)0.062 (4)0.107 (4)0.018 (3)0.008 (3)0.009 (3)
C250.050 (3)0.045 (3)0.071 (3)−0.002 (2)0.014 (2)0.002 (2)
C260.073 (4)0.086 (3)0.117 (3)−0.014 (4)−0.010 (4)−0.0083 (19)
S1'0.073 (4)0.086 (3)0.117 (3)−0.014 (4)−0.010 (4)−0.0083 (19)
C270.072 (5)0.080 (5)0.218 (9)−0.026 (4)0.008 (5)−0.019 (6)
C280.078 (4)0.062 (4)0.157 (7)−0.003 (4)0.047 (4)0.026 (4)
C290.047 (2)0.041 (3)0.045 (2)0.006 (2)0.002 (2)−0.003 (2)
C300.057 (3)0.051 (3)0.056 (3)0.000 (2)0.008 (2)−0.006 (2)
C310.067 (3)0.049 (3)0.052 (3)0.002 (3)0.008 (2)0.002 (2)
C320.084 (4)0.052 (3)0.063 (3)−0.001 (3)0.017 (3)0.001 (2)
C330.063 (3)0.060 (3)0.049 (3)0.004 (3)0.011 (2)0.004 (2)
C340.050 (2)0.044 (3)0.044 (2)0.002 (2)0.008 (2)−0.002 (2)
C350.051 (3)0.061 (3)0.060 (3)0.007 (2)0.013 (2)0.003 (2)
C360.048 (3)0.052 (3)0.046 (2)0.011 (2)0.000 (2)−0.006 (2)
C370.056 (3)0.059 (3)0.051 (3)0.016 (3)−0.007 (2)−0.007 (2)
C380.049 (3)0.050 (3)0.062 (3)0.011 (2)−0.010 (2)−0.006 (2)
C390.063 (3)0.061 (4)0.073 (3)0.014 (3)−0.017 (3)−0.018 (3)
C400.055 (3)0.058 (4)0.096 (4)0.005 (3)−0.014 (3)−0.014 (3)
C410.051 (3)0.062 (4)0.092 (4)−0.002 (3)−0.005 (3)−0.009 (3)
C420.048 (3)0.060 (3)0.078 (3)−0.002 (3)0.004 (2)−0.008 (3)
C430.044 (2)0.049 (3)0.056 (3)0.008 (2)−0.008 (2)−0.010 (2)
C440.045 (2)0.046 (3)0.046 (2)0.007 (2)−0.001 (2)−0.007 (2)
C450.051 (3)0.047 (3)0.043 (2)−0.006 (2)0.007 (2)−0.008 (2)
C460.056 (3)0.060 (3)0.059 (3)0.001 (3)0.010 (2)−0.001 (2)
C470.060 (3)0.073 (4)0.074 (4)−0.001 (3)0.016 (3)−0.007 (3)
C480.070 (4)0.090 (4)0.072 (4)−0.023 (3)0.027 (3)−0.011 (3)
C490.087 (4)0.088 (4)0.057 (3)−0.021 (4)0.006 (3)0.010 (3)
C500.060 (3)0.065 (3)0.058 (3)−0.001 (3)0.000 (2)0.007 (2)
C510.108 (4)0.055 (3)0.081 (4)−0.008 (3)0.031 (3)−0.017 (3)
C520.074 (4)0.089 (4)0.069 (3)−0.009 (3)−0.008 (3)−0.002 (3)
C530.046 (3)0.067 (4)0.080 (3)0.009 (3)0.008 (2)0.005 (3)
C540.054 (2)0.107 (4)0.152 (3)0.003 (2)0.0224 (19)0.049 (3)
S2'0.054 (2)0.107 (4)0.152 (3)0.003 (2)0.0224 (19)0.049 (3)
C550.056 (4)0.113 (6)0.147 (6)0.018 (4)0.002 (4)0.015 (5)
C560.074 (4)0.096 (5)0.123 (5)0.025 (4)−0.010 (4)0.023 (4)
C570.212 (13)0.125 (9)0.148 (9)0.054 (9)0.000 (9)0.007 (7)
C580.310 (14)0.101 (7)0.196 (10)0.007 (8)0.125 (10)0.024 (6)
C590.231 (11)0.161 (9)0.153 (9)−0.078 (8)−0.009 (8)−0.003 (7)
Geometric parameters (Å, º) top
N1—C161.377 (5)C25—C261.43 (4)
N1—C11.416 (5)C25—S1'1.659 (12)
N1—C171.439 (5)C26—C271.54 (4)
N2—C441.376 (5)C26—H260.9300
N2—C291.408 (5)S1'—C271.539 (16)
N2—C451.444 (5)C27—C281.302 (9)
N3—C571.381 (13)C27—H270.9300
N3—C591.417 (10)C28—H280.9300
N3—C581.422 (9)C29—C341.346 (5)
O1—C51.223 (5)C29—C301.491 (5)
O2—C91.228 (5)C30—C311.524 (6)
O3—C331.226 (5)C30—H30A0.9700
O4—C371.222 (5)C30—H30B0.9700
O5—C571.305 (11)C31—C321.521 (6)
S1—C281.593 (14)C31—C521.524 (6)
S1—C251.643 (11)C31—C511.530 (6)
S2—C561.581 (10)C32—C331.496 (6)
S2—C531.617 (10)C32—H32A0.9700
C26'—C281.44 (5)C32—H32B0.9700
C26'—C251.44 (4)C33—C341.456 (6)
C26'—H26'0.9300C34—C351.521 (6)
C54'—C531.37 (3)C35—C361.487 (6)
C54'—C561.37 (3)C35—C531.512 (6)
C54'—H54'0.9300C35—H350.9800
C1—C61.351 (5)C36—C441.350 (5)
C1—C21.497 (6)C36—C371.451 (6)
C2—C31.526 (6)C37—C381.496 (6)
C2—H2A0.9700C38—C391.380 (6)
C2—H2B0.9700C38—C431.402 (6)
C3—C231.521 (6)C39—C401.378 (7)
C3—C41.523 (6)C39—H390.9300
C3—C241.535 (6)C40—C411.360 (6)
C4—C51.496 (6)C40—H400.9300
C4—H4A0.9700C41—C421.380 (6)
C4—H4B0.9700C41—H410.9300
C5—C61.456 (6)C42—C431.370 (6)
C6—C71.508 (6)C42—H420.9300
C7—C81.502 (6)C43—C441.492 (6)
C7—C251.520 (6)C45—C501.362 (6)
C7—H70.9800C45—C461.376 (6)
C8—C161.342 (5)C46—C471.376 (6)
C8—C91.449 (6)C46—H460.9300
C9—C101.500 (6)C47—C481.367 (7)
C10—C111.369 (6)C47—H470.9300
C10—C151.400 (6)C48—C491.365 (7)
C11—C121.385 (7)C48—H480.9300
C11—H110.9300C49—C501.388 (6)
C12—C131.360 (7)C49—H490.9300
C12—H120.9300C50—H500.9300
C13—C141.393 (6)C51—H51A0.9600
C13—H130.9300C51—H51B0.9600
C14—C151.379 (6)C51—H51C0.9600
C14—H140.9300C52—H52A0.9600
C15—C161.497 (5)C52—H52B0.9600
C17—C221.365 (6)C52—H52C0.9600
C17—C181.381 (6)C53—C541.38 (3)
C18—C191.367 (6)C53—S2'1.652 (7)
C18—H180.9300C54—C551.37 (3)
C19—C201.367 (8)C54—H540.9300
C19—H190.9300S2'—C551.619 (10)
C20—C211.365 (8)C55—C561.319 (8)
C20—H200.9300C55—H550.9300
C21—C221.389 (6)C56—H560.9300
C21—H210.9300C57—H570.9300
C22—H220.9300C58—H58A0.9600
C23—H23A0.9600C58—H58B0.9600
C23—H23B0.9600C58—H58C0.9600
C23—H23C0.9600C59—H59A0.9600
C24—H24A0.9600C59—H59B0.9600
C24—H24B0.9600C59—H59C0.9600
C24—H24C0.9600
C16—N1—C1118.3 (3)S1—C28—H28121.2
C16—N1—C17119.8 (3)C34—C29—N2120.6 (4)
C1—N1—C17121.9 (3)C34—C29—C30123.1 (4)
C44—N2—C29118.2 (3)N2—C29—C30116.2 (3)
C44—N2—C45120.8 (3)C29—C30—C31114.3 (3)
C29—N2—C45120.9 (3)C29—C30—H30A108.7
C57—N3—C59113.2 (9)C31—C30—H30A108.7
C57—N3—C58120.9 (10)C29—C30—H30B108.7
C59—N3—C58125.9 (10)C31—C30—H30B108.7
C28—S1—C2594.8 (5)H30A—C30—H30B107.6
C56—S2—C5396.2 (4)C32—C31—C30108.5 (4)
C28—C26'—C25111 (3)C32—C31—C52109.4 (4)
C28—C26'—H26'124.3C30—C31—C52110.3 (4)
C25—C26'—H26'124.3C32—C31—C51110.6 (4)
C53—C54'—C56121.4 (18)C30—C31—C51108.8 (4)
C53—C54'—H54'119.3C52—C31—C51109.3 (4)
C56—C54'—H54'119.3C33—C32—C31113.0 (4)
C6—C1—N1120.1 (4)C33—C32—H32A109.0
C6—C1—C2123.7 (4)C31—C32—H32A109.0
N1—C1—C2116.2 (3)C33—C32—H32B109.0
C1—C2—C3113.7 (4)C31—C32—H32B109.0
C1—C2—H2A108.8H32A—C32—H32B107.8
C3—C2—H2A108.8O3—C33—C34120.8 (4)
C1—C2—H2B108.8O3—C33—C32120.4 (4)
C3—C2—H2B108.8C34—C33—C32118.7 (4)
H2A—C2—H2B107.7C29—C34—C33119.7 (4)
C23—C3—C4110.5 (4)C29—C34—C35123.2 (4)
C23—C3—C2109.2 (4)C33—C34—C35117.2 (3)
C4—C3—C2108.0 (4)C36—C35—C53110.6 (4)
C23—C3—C24108.1 (4)C36—C35—C34107.5 (3)
C4—C3—C24110.1 (4)C53—C35—C34112.2 (4)
C2—C3—C24110.8 (4)C36—C35—H35108.8
C5—C4—C3113.6 (4)C53—C35—H35108.8
C5—C4—H4A108.9C34—C35—H35108.8
C3—C4—H4A108.9C44—C36—C37108.9 (4)
C5—C4—H4B108.9C44—C36—C35123.1 (4)
C3—C4—H4B108.9C37—C36—C35127.7 (4)
H4A—C4—H4B107.7O4—C37—C36128.1 (5)
O1—C5—C6120.4 (4)O4—C37—C38126.3 (4)
O1—C5—C4121.8 (4)C36—C37—C38105.6 (4)
C6—C5—C4117.8 (4)C39—C38—C43121.4 (4)
C1—C6—C5119.6 (4)C39—C38—C37129.4 (4)
C1—C6—C7122.5 (4)C43—C38—C37109.2 (4)
C5—C6—C7117.8 (4)C40—C39—C38118.2 (5)
C8—C7—C6107.5 (3)C40—C39—H39120.9
C8—C7—C25108.9 (3)C38—C39—H39120.9
C6—C7—C25111.4 (4)C41—C40—C39120.5 (5)
C8—C7—H7109.7C41—C40—H40119.7
C6—C7—H7109.7C39—C40—H40119.7
C25—C7—H7109.7C40—C41—C42121.8 (5)
C16—C8—C9109.4 (4)C40—C41—H41119.1
C16—C8—C7122.0 (4)C42—C41—H41119.1
C9—C8—C7127.8 (4)C43—C42—C41119.0 (5)
O2—C9—C8127.9 (5)C43—C42—H42120.5
O2—C9—C10126.2 (4)C41—C42—H42120.5
C8—C9—C10105.9 (4)C42—C43—C38119.1 (4)
C11—C10—C15121.4 (5)C42—C43—C44135.9 (4)
C11—C10—C9130.3 (5)C38—C43—C44105.0 (4)
C15—C10—C9108.3 (4)C36—C44—N2122.3 (4)
C10—C11—C12118.9 (5)C36—C44—C43111.3 (4)
C10—C11—H11120.6N2—C44—C43126.4 (4)
C12—C11—H11120.6C50—C45—C46121.2 (4)
C13—C12—C11120.0 (5)C50—C45—N2119.2 (4)
C13—C12—H12120.0C46—C45—N2119.5 (4)
C11—C12—H12120.0C47—C46—C45119.0 (5)
C12—C13—C14122.0 (5)C47—C46—H46120.5
C12—C13—H13119.0C45—C46—H46120.5
C14—C13—H13119.0C48—C47—C46120.2 (5)
C15—C14—C13118.2 (5)C48—C47—H47119.9
C15—C14—H14120.9C46—C47—H47119.9
C13—C14—H14120.9C49—C48—C47120.5 (5)
C14—C15—C10119.5 (4)C49—C48—H48119.8
C14—C15—C16134.7 (4)C47—C48—H48119.8
C10—C15—C16105.8 (4)C48—C49—C50119.9 (5)
C8—C16—N1122.1 (4)C48—C49—H49120.1
C8—C16—C15110.6 (4)C50—C49—H49120.1
N1—C16—C15127.3 (4)C45—C50—C49119.2 (5)
C22—C17—C18120.9 (4)C45—C50—H50120.4
C22—C17—N1120.7 (4)C49—C50—H50120.4
C18—C17—N1118.3 (4)C31—C51—H51A109.5
C19—C18—C17120.3 (5)C31—C51—H51B109.5
C19—C18—H18119.9H51A—C51—H51B109.5
C17—C18—H18119.9C31—C51—H51C109.5
C18—C19—C20118.9 (5)H51A—C51—H51C109.5
C18—C19—H19120.5H51B—C51—H51C109.5
C20—C19—H19120.5C31—C52—H52A109.5
C21—C20—C19121.3 (5)C31—C52—H52B109.5
C21—C20—H20119.3H52A—C52—H52B109.5
C19—C20—H20119.3C31—C52—H52C109.5
C20—C21—C22120.0 (5)H52A—C52—H52C109.5
C20—C21—H21120.0H52B—C52—H52C109.5
C22—C21—H21120.0C54'—C53—C5491.3 (16)
C17—C22—C21118.6 (5)C54'—C53—C35132.6 (11)
C17—C22—H22120.7C54—C53—C35136.0 (13)
C21—C22—H22120.7C54—C53—S2103.4 (12)
C3—C23—H23A109.5C35—C53—S2120.5 (4)
C3—C23—H23B109.5C54'—C53—S2'104.2 (11)
H23A—C23—H23B109.5C35—C53—S2'123.2 (4)
C3—C23—H23C109.5S2—C53—S2'115.7 (5)
H23A—C23—H23C109.5C55—C54—C53119.9 (18)
H23B—C23—H23C109.5C55—C54—H54120.0
C3—C24—H24A109.5C53—C54—H54120.0
C3—C24—H24B109.5C55—S2'—C5393.3 (4)
H24A—C24—H24B109.5C56—C55—C54104.0 (11)
C3—C24—H24C109.5C56—C55—S2'117.6 (5)
H24A—C24—H24C109.5C56—C55—H55128.0
H24B—C24—H24C109.5C54—C55—H55128.0
C26—C25—C26'104 (3)S2'—C55—H55114.0
C26—C25—C7127.8 (18)C55—C56—C54'103.1 (12)
C26'—C25—C7128.4 (19)C55—C56—S2116.2 (6)
C26—C25—S1111.3 (18)C55—C56—H56121.9
C7—C25—S1120.9 (5)C54'—C56—H56134.7
C26'—C25—S1'105.8 (19)S2—C56—H56121.9
C7—C25—S1'124.8 (5)O5—C57—N3118.7 (13)
S1—C25—S1'113.2 (6)O5—C57—H57120.6
C25—C26—C27106 (3)N3—C57—H57120.6
C25—C26—H26126.8N3—C58—H58A109.5
C27—C26—H26126.8N3—C58—H58B109.5
C27—S1'—C2596.2 (7)H58A—C58—H58B109.5
C28—C27—S1'117.7 (7)N3—C58—H58C109.5
C28—C27—C26108.6 (15)H58A—C58—H58C109.5
C28—C27—H27125.7H58B—C58—H58C109.5
S1'—C27—H27115.5N3—C59—H59A109.5
C26—C27—H27125.7N3—C59—H59B109.5
C27—C28—C26'108.5 (18)H59A—C59—H59B109.5
C27—C28—S1117.5 (6)N3—C59—H59C109.5
C27—C28—H28121.2H59A—C59—H59C109.5
C26'—C28—H28130.3H59B—C59—H59C109.5

Experimental details

Crystal data
Chemical formulaC28H23NO2S·0.5C3H7NO
Mr474.08
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)15.081 (2), 9.4381 (14), 35.102 (3)
β (°) 92.041 (3)
V (Å3)4992.9 (11)
Z8
Radiation typeMo Kα
µ (mm−1)0.16
Crystal size (mm)0.43 × 0.32 × 0.28
Data collection
DiffractometerBruker CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.934, 0.957
No. of measured, independent and
observed [I > 2σ(I)] reflections		25441, 8790, 3935
Rint0.058
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.216, 1.00
No. of reflections8790
No. of parameters636
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.47, −0.38

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.

 

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