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The asymmetric unit of the title solvate, C21H22N2O2·CH3OH, contains one methanol solvent mol­ecule and one mol­ecule of the heterocycle that is built up by the fusion of four six-membered rings A, C, D, E and one five-membered ring B. The indole moiety (rings A and B) is essentially planar, with an r.m.s. deviation of 0.013 Å, whereas rings C and D adopt a twisted conformation with a trans-ring junction. In the crystal, two heterocyclic mol­ecules are associated with two methanol mol­ecules through mutual N—H...O and O—H...N hydrogen bonds, forming a centrosymmetric dimer.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015013286/wm5184sup1.cif
Contains datablocks I, New_Global_Publ_Block

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989015013286/wm5184Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015013286/wm5184Isup3.cml
Supplementary material

CCDC reference: 1412105

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.040
  • wR factor = 0.120
  • Data-to-parameter ratio = 15.4

checkCIF/PLATON results

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Alert level C PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 2.636 Check
Alert level G PLAT154_ALERT_1_G The su's on the Cell Angles are Equal .......... 0.00400 Degree PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check PLAT793_ALERT_4_G The Model has Chirality at C5 (Centro SPGR) R Verify PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2014 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 61 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 6 ALERT level G = General information/check it is not something unexpected 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Synthesis and crystallization top

The synthesis of the title compound was described previously (Saidov et al., 2014). Orange crystals were obtained in a methanol:chloro­form 1:1 (v/v) mixture by slow evaporation of the solvent at room temperature.

Refinement top

Carbon-bound H atoms were placed geometrically and treated as riding on their parent atoms, with C—H = 0.93 Å (aromatic), 0.97 Å (methylen) or 0.96 Å (methyl) and were refined with Uiso(H) = 1.2Ueq(C) for aromatic and methyl­ene hydrogens and Uiso(H) = 1.5Ueq(C) for methyl H atoms. The N- and O-bound H atoms were located in a difference Fourier map and were refined freely.

Related literature top

Synthetic details regarding the title compound were described by Saidov et al. (2014). For synthetic procedures of related compounds and their structures, see: Saidov et al. (2013). For another related crystal structure, see: Yu et al. (1995).

Structure description top

Synthetic details regarding the title compound were described by Saidov et al. (2014). For synthetic procedures of related compounds and their structures, see: Saidov et al. (2013). For another related crystal structure, see: Yu et al. (1995).

Synthesis and crystallization top

The synthesis of the title compound was described previously (Saidov et al., 2014). Orange crystals were obtained in a methanol:chloro­form 1:1 (v/v) mixture by slow evaporation of the solvent at room temperature.

Refinement details top

Carbon-bound H atoms were placed geometrically and treated as riding on their parent atoms, with C—H = 0.93 Å (aromatic), 0.97 Å (methylen) or 0.96 Å (methyl) and were refined with Uiso(H) = 1.2Ueq(C) for aromatic and methyl­ene hydrogens and Uiso(H) = 1.5Ueq(C) for methyl H atoms. The N- and O-bound H atoms were located in a difference Fourier map and were refined freely.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular components of the title compound, with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Hydrogen bonding between the molecular components, leading to the formation of dimers.
2,3-Dimethoxy-5,6,7,8,13,13a-hexahydro-6a,8-diazaindeno[2,1-b]phenanthrene methanol monosolvate top
Crystal data top
C21H22N2O2·CH4OZ = 2
Mr = 366.45F(000) = 392
Triclinic, P1Dx = 1.273 Mg m3
Hall symbol: -P 1Melting point: 393(2) K
a = 7.6080 (3) ÅCu Kα radiation, λ = 1.54184 Å
b = 11.8061 (5) ÅCell parameters from 7310 reflections
c = 12.3327 (5) Åθ = 4.0–75.6°
α = 65.242 (4)°µ = 0.68 mm1
β = 73.956 (4)°T = 293 K
γ = 75.724 (4)°Prism, orange
V = 955.81 (7) Å30.42 × 0.25 × 0.12 mm
Data collection top
Oxford Diffraction Xcalibur Ruby
diffractometer
3936 independent reflections
Radiation source: Enhance (Cu) X-ray Source2889 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
Detector resolution: 10.2576 pixels mm-1θmax = 75.8°, θmin = 4.0°
ω scansh = 98
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
k = 1414
Tmin = 0.843, Tmax = 1.000l = 1515
19864 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.120 w = 1/[σ2(Fo2) + (0.069P)2 + 0.0547P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.002
3936 reflectionsΔρmax = 0.17 e Å3
256 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0025 (6)
Crystal data top
C21H22N2O2·CH4Oγ = 75.724 (4)°
Mr = 366.45V = 955.81 (7) Å3
Triclinic, P1Z = 2
a = 7.6080 (3) ÅCu Kα radiation
b = 11.8061 (5) ŵ = 0.68 mm1
c = 12.3327 (5) ÅT = 293 K
α = 65.242 (4)°0.42 × 0.25 × 0.12 mm
β = 73.956 (4)°
Data collection top
Oxford Diffraction Xcalibur Ruby
diffractometer
3936 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
2889 reflections with I > 2σ(I)
Tmin = 0.843, Tmax = 1.000Rint = 0.046
19864 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.17 e Å3
3936 reflectionsΔρmin = 0.17 e Å3
256 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*/Ueq
O10.58933 (14)0.05796 (10)1.11979 (9)0.0544 (3)
O20.27998 (15)0.08093 (10)1.27098 (9)0.0582 (3)
O30.10908 (17)0.72865 (11)0.27339 (11)0.0653 (3)
N10.30388 (18)0.48439 (12)0.39691 (11)0.0499 (3)
N40.13746 (15)0.41753 (10)0.72574 (10)0.0430 (3)
C20.2862 (2)0.43976 (13)0.52151 (13)0.0457 (3)
C30.1738 (2)0.50958 (13)0.59986 (12)0.0462 (3)
H3A0.24040.57230.59510.055*
H3B0.05810.55230.57300.055*
C50.31440 (18)0.34322 (13)0.76212 (12)0.0437 (3)
H5A0.40350.40200.73380.052*
C60.3879 (2)0.25152 (14)0.69509 (13)0.0497 (3)
H6A0.51470.21470.70360.060*
H6B0.31390.18380.73050.060*
C70.37932 (19)0.32112 (14)0.56320 (13)0.0464 (3)
C80.45916 (19)0.28619 (14)0.45984 (13)0.0475 (3)
C90.5643 (2)0.17724 (16)0.44332 (16)0.0590 (4)
H9A0.59610.10630.50970.071*
C100.6200 (2)0.17645 (19)0.32772 (17)0.0669 (5)
H10A0.68950.10420.31630.080*
C110.5741 (2)0.28218 (19)0.22718 (16)0.0654 (5)
H11A0.61470.27920.14990.078*
C120.4700 (2)0.39083 (17)0.23980 (14)0.0578 (4)
H12A0.44050.46120.17240.069*
C130.4104 (2)0.39180 (15)0.35692 (13)0.0493 (3)
C140.0333 (2)0.48294 (13)0.80799 (13)0.0485 (3)
H14A0.07280.53920.77600.058*
H14B0.11130.53290.81410.058*
C150.0305 (2)0.38641 (14)0.93244 (13)0.0502 (4)
H15A0.09320.42860.98840.060*
H15B0.11740.34180.92730.060*
C160.29541 (19)0.27694 (13)0.89861 (12)0.0438 (3)
C170.13271 (19)0.29376 (13)0.97944 (13)0.0455 (3)
C180.1258 (2)0.22773 (14)1.10490 (13)0.0493 (3)
H18A0.01620.23761.15900.059*
C190.2769 (2)0.14886 (13)1.14984 (13)0.0473 (3)
C200.44399 (19)0.13467 (13)1.06780 (13)0.0452 (3)
C210.45059 (19)0.19815 (13)0.94490 (13)0.0456 (3)
H21A0.56070.18870.89090.055*
C220.7633 (2)0.04838 (16)1.04086 (15)0.0574 (4)
H22A0.85580.00201.08830.086*
H22B0.79610.13110.99280.086*
H22C0.75550.00960.98810.086*
C230.1439 (3)0.12453 (19)1.35495 (15)0.0724 (5)
H23A0.17140.07931.43500.109*
H23B0.02460.11091.35490.109*
H23C0.14330.21301.33190.109*
C240.0459 (3)0.81552 (19)0.3320 (2)0.0782 (5)
H24A0.05990.79000.39510.117*
H24B0.01220.89790.27370.117*
H24C0.14250.81780.36700.117*
H1A0.254 (2)0.5621 (17)0.3504 (15)0.060 (5)*
H30.014 (3)0.694 (2)0.2747 (18)0.085 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0513 (6)0.0577 (6)0.0479 (6)0.0017 (5)0.0120 (4)0.0179 (5)
O20.0644 (7)0.0589 (6)0.0423 (6)0.0024 (5)0.0066 (5)0.0166 (5)
O30.0602 (7)0.0617 (7)0.0753 (8)0.0148 (6)0.0117 (6)0.0251 (6)
N10.0513 (7)0.0490 (7)0.0448 (7)0.0092 (6)0.0086 (5)0.0129 (6)
N40.0425 (6)0.0410 (6)0.0441 (6)0.0033 (5)0.0078 (5)0.0168 (5)
C20.0443 (8)0.0471 (7)0.0443 (7)0.0111 (6)0.0063 (6)0.0151 (6)
C30.0470 (8)0.0412 (7)0.0476 (8)0.0066 (6)0.0094 (6)0.0141 (6)
C50.0382 (7)0.0464 (7)0.0456 (7)0.0057 (6)0.0070 (6)0.0176 (6)
C60.0483 (8)0.0512 (8)0.0455 (8)0.0031 (6)0.0102 (6)0.0195 (6)
C70.0430 (8)0.0499 (8)0.0452 (7)0.0058 (6)0.0068 (6)0.0186 (6)
C80.0409 (8)0.0554 (8)0.0490 (8)0.0098 (6)0.0074 (6)0.0217 (7)
C90.0531 (9)0.0632 (10)0.0638 (10)0.0000 (7)0.0114 (7)0.0318 (8)
C100.0594 (10)0.0801 (12)0.0719 (12)0.0031 (9)0.0079 (8)0.0462 (10)
C110.0586 (10)0.0928 (13)0.0580 (10)0.0202 (9)0.0002 (8)0.0432 (10)
C120.0548 (9)0.0743 (11)0.0481 (8)0.0198 (8)0.0061 (7)0.0238 (8)
C130.0419 (8)0.0588 (9)0.0501 (8)0.0149 (6)0.0055 (6)0.0215 (7)
C140.0467 (8)0.0461 (8)0.0540 (8)0.0009 (6)0.0090 (6)0.0240 (7)
C150.0432 (8)0.0561 (8)0.0513 (8)0.0028 (6)0.0048 (6)0.0256 (7)
C160.0422 (7)0.0452 (7)0.0456 (7)0.0079 (6)0.0063 (6)0.0194 (6)
C170.0432 (8)0.0470 (7)0.0478 (8)0.0071 (6)0.0067 (6)0.0206 (6)
C180.0466 (8)0.0526 (8)0.0470 (8)0.0082 (6)0.0010 (6)0.0219 (7)
C190.0534 (9)0.0460 (7)0.0428 (7)0.0087 (6)0.0073 (6)0.0178 (6)
C200.0466 (8)0.0438 (7)0.0481 (8)0.0045 (6)0.0115 (6)0.0201 (6)
C210.0408 (7)0.0507 (8)0.0457 (8)0.0056 (6)0.0054 (6)0.0212 (6)
C220.0457 (8)0.0602 (9)0.0602 (9)0.0036 (7)0.0108 (7)0.0192 (8)
C230.0702 (12)0.0829 (12)0.0440 (9)0.0036 (9)0.0024 (8)0.0185 (9)
C240.0810 (13)0.0703 (12)0.0934 (14)0.0119 (10)0.0234 (11)0.0362 (11)
Geometric parameters (Å, º) top
O1—C201.3658 (17)C10—H10A0.9300
O1—C221.4207 (18)C11—C121.376 (2)
O2—C191.3720 (17)C11—H11A0.9300
O2—C231.4143 (19)C12—C131.393 (2)
O3—C241.411 (2)C12—H12A0.9300
O3—H30.91 (2)C14—C151.512 (2)
N1—C131.3743 (19)C14—H14A0.9700
N1—C21.3782 (18)C14—H14B0.9700
N1—H1A0.907 (18)C15—C171.507 (2)
N4—C141.4706 (17)C15—H15A0.9700
N4—C31.4716 (17)C15—H15B0.9700
N4—C51.4849 (17)C16—C171.3885 (19)
C2—C71.355 (2)C16—C211.4040 (19)
C2—C31.4856 (19)C17—C181.403 (2)
C3—H3A0.9700C18—C191.373 (2)
C3—H3B0.9700C18—H18A0.9300
C5—C161.5115 (19)C19—C201.412 (2)
C5—C61.5374 (19)C20—C211.3735 (19)
C5—H5A0.9800C21—H21A0.9300
C6—C71.4959 (19)C22—H22A0.9600
C6—H6A0.9700C22—H22B0.9600
C6—H6B0.9700C22—H22C0.9600
C7—C81.433 (2)C23—H23A0.9600
C8—C91.399 (2)C23—H23B0.9600
C8—C131.418 (2)C23—H23C0.9600
C9—C101.374 (2)C24—H24A0.9600
C9—H9A0.9300C24—H24B0.9600
C10—C111.395 (3)C24—H24C0.9600
C20—O1—C22117.34 (11)C12—C13—C8121.50 (15)
C19—O2—C23116.67 (12)N4—C14—C15109.21 (11)
C24—O3—H3111.0 (13)N4—C14—H14A109.8
C13—N1—C2108.22 (13)C15—C14—H14A109.8
C13—N1—H1A126.7 (11)N4—C14—H14B109.8
C2—N1—H1A125.0 (11)C15—C14—H14B109.8
C14—N4—C3109.92 (10)H14A—C14—H14B108.3
C14—N4—C5111.77 (11)C17—C15—C14110.14 (12)
C3—N4—C5109.95 (10)C17—C15—H15A109.6
C7—C2—N1110.50 (13)C14—C15—H15A109.6
C7—C2—C3124.68 (13)C17—C15—H15B109.6
N1—C2—C3124.76 (13)C14—C15—H15B109.6
N4—C3—C2107.82 (11)H15A—C15—H15B108.1
N4—C3—H3A110.1C17—C16—C21119.03 (13)
C2—C3—H3A110.1C17—C16—C5122.61 (13)
N4—C3—H3B110.1C21—C16—C5118.33 (12)
C2—C3—H3B110.1C16—C17—C18119.08 (13)
H3A—C3—H3B108.5C16—C17—C15120.00 (13)
N4—C5—C16112.57 (11)C18—C17—C15120.86 (12)
N4—C5—C6108.21 (11)C19—C18—C17121.73 (13)
C16—C5—C6112.62 (11)C19—C18—H18A119.1
N4—C5—H5A107.7C17—C18—H18A119.1
C16—C5—H5A107.7O2—C19—C18124.92 (13)
C6—C5—H5A107.7O2—C19—C20115.89 (13)
C7—C6—C5109.45 (12)C18—C19—C20119.19 (13)
C7—C6—H6A109.8O1—C20—C21125.15 (13)
C5—C6—H6A109.8O1—C20—C19115.63 (12)
C7—C6—H6B109.8C21—C20—C19119.21 (13)
C5—C6—H6B109.8C20—C21—C16121.71 (13)
H6A—C6—H6B108.2C20—C21—H21A119.1
C2—C7—C8106.95 (13)C16—C21—H21A119.1
C2—C7—C6121.66 (13)O1—C22—H22A109.5
C8—C7—C6131.38 (13)O1—C22—H22B109.5
C9—C8—C13118.97 (14)H22A—C22—H22B109.5
C9—C8—C7134.61 (15)O1—C22—H22C109.5
C13—C8—C7106.42 (13)H22A—C22—H22C109.5
C10—C9—C8119.10 (17)H22B—C22—H22C109.5
C10—C9—H9A120.5O2—C23—H23A109.5
C8—C9—H9A120.5O2—C23—H23B109.5
C9—C10—C11121.15 (17)H23A—C23—H23B109.5
C9—C10—H10A119.4O2—C23—H23C109.5
C11—C10—H10A119.4H23A—C23—H23C109.5
C12—C11—C10121.47 (16)H23B—C23—H23C109.5
C12—C11—H11A119.3O3—C24—H24A109.5
C10—C11—H11A119.3O3—C24—H24B109.5
C11—C12—C13117.78 (16)H24A—C24—H24B109.5
C11—C12—H12A121.1O3—C24—H24C109.5
C13—C12—H12A121.1H24A—C24—H24C109.5
N1—C13—C12130.61 (15)H24B—C24—H24C109.5
N1—C13—C8107.89 (13)
C13—N1—C2—C70.40 (16)C7—C8—C13—N11.05 (16)
C13—N1—C2—C3177.03 (13)C9—C8—C13—C122.2 (2)
C14—N4—C3—C2177.49 (12)C7—C8—C13—C12178.47 (13)
C5—N4—C3—C254.04 (14)C3—N4—C14—C15170.60 (11)
C7—C2—C3—N416.43 (19)C5—N4—C14—C1567.03 (15)
N1—C2—C3—N4160.63 (13)N4—C14—C15—C1756.04 (16)
C14—N4—C5—C1639.91 (15)N4—C5—C16—C175.02 (19)
C3—N4—C5—C16162.27 (11)C6—C5—C16—C17127.70 (15)
C14—N4—C5—C6165.02 (11)N4—C5—C16—C21176.81 (12)
C3—N4—C5—C672.62 (13)C6—C5—C16—C2154.14 (17)
N4—C5—C6—C747.51 (15)C21—C16—C17—C182.5 (2)
C16—C5—C6—C7172.59 (11)C5—C16—C17—C18179.38 (13)
N1—C2—C7—C81.06 (17)C21—C16—C17—C15174.74 (13)
C3—C2—C7—C8176.37 (13)C5—C16—C17—C153.4 (2)
N1—C2—C7—C6178.11 (13)C14—C15—C17—C1621.95 (19)
C3—C2—C7—C64.5 (2)C14—C15—C17—C18155.21 (13)
C5—C6—C7—C211.52 (19)C16—C17—C18—C191.3 (2)
C5—C6—C7—C8167.41 (14)C15—C17—C18—C19175.89 (14)
C2—C7—C8—C9177.88 (16)C23—O2—C19—C1821.5 (2)
C6—C7—C8—C93.1 (3)C23—O2—C19—C20158.32 (15)
C2—C7—C8—C131.28 (16)C17—C18—C19—O2179.63 (13)
C6—C7—C8—C13177.76 (14)C17—C18—C19—C200.6 (2)
C13—C8—C9—C101.1 (2)C22—O1—C20—C213.5 (2)
C7—C8—C9—C10179.79 (16)C22—O1—C20—C19175.59 (13)
C8—C9—C10—C110.2 (3)O2—C19—C20—O11.91 (19)
C9—C10—C11—C120.6 (3)C18—C19—C20—O1177.89 (12)
C10—C11—C12—C130.4 (2)O2—C19—C20—C21178.95 (12)
C2—N1—C13—C12179.03 (15)C18—C19—C20—C211.3 (2)
C2—N1—C13—C80.44 (16)O1—C20—C21—C16179.02 (13)
C11—C12—C13—N1178.76 (15)C19—C20—C21—C160.0 (2)
C11—C12—C13—C81.8 (2)C17—C16—C21—C201.8 (2)
C9—C8—C13—N1178.27 (13)C5—C16—C21—C20179.92 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O30.907 (19)1.982 (19)2.880 (2)170.1 (16)
O3—H3···N4i0.91 (2)1.95 (2)2.840 (2)165 (2)
Symmetry code: (i) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O30.907 (19)1.982 (19)2.880 (2)170.1 (16)
O3—H3···N4i0.91 (2)1.95 (2)2.840 (2)165 (2)
Symmetry code: (i) x, y+1, z+1.
 

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