Literature DB >> 21580014

12-Eth-oxy-2,3,8,9-tetra-methoxy-benzo[c]phenanthridine dichloro-methane solvate.

Michael Ronaldson, Chad R Maheux, James M Nyangulu, T Stanley Cameron, Manuel A S Aquino.   

Abstract

The title compound, C(23)H(23)NO(5)·CH(2)Cl(2), was obtained via the alkyl-ation of the 12-hydr-oxy-2,3,8,9-tetra-methoxy-benzo[c]phenanthridine salt. The benzo[c]phenanthridine ring system is essentially planar, with a mean out-of-plane deviation of 0.026 Å. A dicloromethane mol-ecule of solvation is present and located between the sheets of phenanthridine mol-ecules, preventing any significant inter-molecular hydrogen-bonding or π-π inter-actions.

Entities:  

Year:  2009        PMID： 21580014      PMCID： PMC2980059          DOI： 10.1107/S1600536809050818

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related structures, see: Marek et al. (2002 ▶); Olugbade & Waigh (1996 ▶); Shabashov & Daugulis (2007 ▶).

Experimental

Crystal data

C23H23NO5·CH2Cl2 M = 478.37 Triclinic, a = 7.6176 (7) Å b = 12.874 (3) Å c = 13.009 (2) Å α = 107.468 (9)° β = 96.7300 (11)° γ = 103.134 (6)° V = 1161.3 (3) Å3 Z = 2 Mo Kα radiation μ = 0.32 mm−1 T = 297 K 0.45 × 0.32 × 0.28 mm

Data collection

Rigaku R-AXIS RAPID diffractometer Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.735, T max = 0.916 16719 measured reflections 4984 independent reflections 3144 reflections with F 2 > 2.0σ(F 2) R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.056 wR(F 2) = 0.071 S = 1.10 3144 reflections 299 parameters All H-atom parameters refined Δρmax = 0.23 e Å−3 Δρmin = −0.29 e Å−3 Data collection: PROCESS (Rigaku/MSC and Rigaku, 2006 ▶); cell refinement: PROCESS; data reduction: CrystalStructure (Rigaku/MSC and Rigaku, 2006 ▶); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: CrystalStructure. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050818/lh2944sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050818/lh2944Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C23H23NO5·CH2Cl2Z = 2
Mr = 478.37F(000) = 500.00
Triclinic, P1Dx = 1.368 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71070 Å
a = 7.6176 (7) ÅCell parameters from 2532 reflections
b = 12.874 (3) Åθ = 2.8–35.0°
c = 13.009 (2) ŵ = 0.32 mm−1
α = 107.468 (9)°T = 297 K
β = 96.7300 (11)°Block, colourless
γ = 103.134 (6)°0.45 × 0.32 × 0.28 mm
V = 1161.3 (3) Å3
Rigaku R-AXIS RAPID diffractometer3144 reflections with F2 > 2.0σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.042
ω scansθmax = 35.7°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −12→12
Tmin = 0.735, Tmax = 0.916k = −21→21
16719 measured reflectionsl = −21→21
4984 independent reflections
Refinement on F0 restraints
R[F2 > 2σ(F2)] = 0.056All H-atom parameters refined
wR(F2) = 0.071 Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979) 9.5043 4.1025 7.0826
S = 1.10(Δ/σ)max < 0.001
3144 reflectionsΔρmax = 0.23 e Å−3
299 parametersΔρmin = −0.29 e Å−3
Refinement. Refinement was performed using reflections with F2 > 3.0 σ(F2). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).
xyzUiso*/Ueq
CL10.57834 (14)0.48531 (8)0.12892 (8)0.1030 (3)
CL20.65852 (14)0.43659 (8)0.33198 (9)0.1048 (3)
O10.4347 (2)0.23338 (16)−0.29456 (13)0.0659 (4)
O20.7420 (2)0.34392 (16)−0.31719 (13)0.0656 (4)
O30.3983 (2)0.07039 (14)0.19755 (12)0.0597 (4)
O40.8982 (2)0.12439 (17)0.51431 (14)0.0720 (5)
O51.1964 (2)0.23385 (16)0.48175 (13)0.0674 (4)
N11.0471 (2)0.31310 (17)0.12497 (15)0.0568 (5)
C10.5648 (3)0.2258 (2)−0.11897 (17)0.0538 (5)
C20.5768 (3)0.25700 (19)−0.21031 (17)0.0533 (5)
C30.7499 (3)0.3197 (2)−0.22228 (17)0.0539 (5)
C40.9017 (3)0.3493 (2)−0.14131 (18)0.0551 (6)
C51.0462 (3)0.3431 (2)0.03733 (18)0.0582 (6)
C60.8815 (2)0.25253 (18)0.13772 (16)0.0486 (5)
C70.7164 (2)0.22220 (18)0.06207 (17)0.0492 (5)
C80.7207 (2)0.25445 (18)−0.03513 (16)0.0485 (5)
C90.8894 (3)0.31686 (18)−0.04683 (17)0.0516 (5)
C100.5508 (2)0.16038 (19)0.08156 (17)0.0526 (5)
C110.5507 (2)0.12897 (18)0.17248 (17)0.0504 (5)
C120.7184 (3)0.1245 (2)0.34684 (18)0.0543 (5)
C130.8790 (3)0.1520 (2)0.42088 (17)0.0562 (6)
C141.0466 (3)0.2147 (2)0.40409 (17)0.0535 (5)
C151.0454 (3)0.24772 (19)0.31279 (18)0.0536 (5)
C160.8821 (3)0.21968 (18)0.23475 (16)0.0494 (5)
C170.7176 (2)0.15731 (18)0.25179 (16)0.0495 (5)
C180.2535 (3)0.1832 (2)−0.2814 (2)0.0682 (7)
C190.9107 (3)0.4051 (2)−0.3347 (2)0.0717 (7)
C200.2253 (3)0.0407 (2)0.12298 (18)0.0566 (6)
C210.0823 (3)−0.0271 (2)0.1655 (2)0.0653 (7)
C220.7374 (4)0.0634 (2)0.5381 (2)0.0810 (8)
C231.3707 (3)0.2858 (2)0.4631 (2)0.0709 (7)
C240.5047 (5)0.4727 (4)0.2476 (3)0.1141 (15)
H10.44930.1844−0.11190.066*
H21.01640.3915−0.14850.091*
H31.15980.38590.02920.076*
H40.43880.14060.03030.063*
H50.60730.08340.35900.068*
H61.15690.29010.30210.060*
H70.25340.1169−0.26330.097*
H80.16780.1631−0.34840.088*
H90.21960.2357−0.22450.070*
H100.99480.3601−0.34200.088*
H110.96240.4733−0.27400.088*
H120.88810.4229−0.40010.088*
H130.19440.10750.12040.068*
H140.2328−0.00340.05160.068*
H151.37470.36040.46430.085*
H161.38740.24260.39350.085*
H171.46590.28890.51910.085*
H18−0.0328−0.05040.11620.078*
H190.07220.01840.23590.078*
H200.1167−0.09190.17120.078*
H210.6854−0.00660.47970.099*
H220.76810.04930.60460.099*
H230.65080.10660.54570.099*
H240.48860.54350.28860.228*
H250.39200.41600.22640.232*
U11U22U33U12U13U23
CL10.1017 (6)0.1080 (6)0.1040 (6)0.0293 (5)0.0281 (5)0.0396 (5)
CL20.1012 (6)0.1100 (6)0.1307 (7)0.0361 (5)0.0482 (5)0.0656 (5)
O10.0527 (9)0.0983 (12)0.0515 (8)0.0100 (8)0.0015 (7)0.0434 (8)
O20.0567 (9)0.0941 (11)0.0543 (8)0.0111 (8)0.0100 (7)0.0445 (8)
O30.0472 (8)0.0802 (10)0.0541 (8)0.0057 (7)0.0054 (6)0.0366 (7)
O40.0577 (9)0.1055 (13)0.0588 (9)0.0072 (9)0.0015 (7)0.0515 (9)
O50.0500 (8)0.0993 (12)0.0544 (8)0.0082 (8)−0.0008 (7)0.0416 (8)
N10.0493 (10)0.0692 (11)0.0509 (9)0.0070 (8)0.0029 (7)0.0286 (8)
C10.0485 (11)0.0694 (13)0.0479 (10)0.0122 (9)0.0076 (9)0.0297 (10)
C20.0497 (11)0.0662 (12)0.0449 (10)0.0116 (9)0.0042 (8)0.0253 (9)
C30.0547 (12)0.0673 (13)0.0460 (10)0.0145 (10)0.0109 (9)0.0294 (10)
C40.0541 (12)0.0649 (12)0.0497 (11)0.0113 (10)0.0105 (9)0.0279 (10)
C50.0513 (12)0.0714 (13)0.0510 (11)0.0060 (10)0.0041 (9)0.0300 (10)
C60.0472 (10)0.0551 (11)0.0430 (10)0.0102 (8)0.0044 (8)0.0204 (8)
C70.0497 (11)0.0563 (11)0.0450 (10)0.0141 (9)0.0070 (8)0.0230 (9)
C80.0491 (11)0.0570 (11)0.0420 (9)0.0134 (9)0.0067 (8)0.0224 (9)
C90.0505 (11)0.0591 (11)0.0469 (10)0.0119 (9)0.0066 (8)0.0238 (9)
C100.0470 (11)0.0650 (12)0.0468 (10)0.0115 (9)0.0033 (8)0.0254 (9)
C110.0460 (11)0.0582 (11)0.0470 (10)0.0103 (9)0.0055 (8)0.0223 (9)
C120.0489 (11)0.0662 (12)0.0515 (11)0.0109 (9)0.0075 (9)0.0298 (10)
C130.0564 (12)0.0700 (13)0.0473 (11)0.0152 (10)0.0085 (9)0.0293 (10)
C140.0504 (11)0.0677 (13)0.0434 (10)0.0133 (9)0.0037 (8)0.0245 (9)
C150.0503 (11)0.0628 (12)0.0479 (11)0.0112 (9)0.0046 (8)0.0244 (9)
C160.0508 (11)0.0573 (11)0.0433 (10)0.0150 (9)0.0075 (8)0.0223 (9)
C170.0496 (11)0.0570 (11)0.0448 (10)0.0141 (9)0.0058 (8)0.0232 (9)
C180.0452 (12)0.0979 (18)0.0603 (13)0.0052 (11)−0.0021 (10)0.0404 (13)
C190.0683 (15)0.0919 (17)0.0630 (14)0.0114 (13)0.0199 (12)0.0430 (13)
C200.0478 (11)0.0678 (13)0.0546 (12)0.0120 (10)0.0080 (9)0.0249 (10)
C210.0566 (13)0.0704 (14)0.0673 (14)0.0082 (10)0.0135 (11)0.0276 (12)
C220.0703 (16)0.111 (2)0.0660 (15)0.0031 (14)0.0095 (12)0.0538 (15)
C230.0503 (12)0.105 (2)0.0566 (13)0.0118 (12)0.0015 (10)0.0363 (13)
C240.085 (2)0.157 (3)0.128 (3)0.049 (2)0.044 (2)0.069 (2)
CL1—C241.743 (5)C14—C151.376 (3)
CL2—C241.746 (5)C15—C161.410 (3)
O1—C21.355 (2)C16—C171.407 (3)
O1—C181.439 (3)C20—C211.501 (3)
O2—C31.359 (3)C1—H10.949
O2—C191.429 (3)C4—H20.950
O3—C111.365 (2)C5—H30.950
O3—C201.439 (2)C10—H40.950
O4—C131.366 (3)C12—H50.948
O4—C221.418 (3)C15—H60.950
O5—C141.355 (2)C18—H70.951
O5—C231.427 (3)C18—H80.953
N1—C51.309 (3)C18—H90.946
N1—C61.381 (2)C19—H100.951
C1—C21.370 (3)C19—H110.950
C1—C81.412 (2)C19—H120.951
C2—C31.434 (3)C20—H130.950
C3—C41.366 (3)C20—H140.947
C4—C91.418 (3)C21—H180.950
C5—C91.424 (3)C21—H190.950
C6—C71.400 (2)C21—H200.950
C6—C161.446 (3)C22—H210.950
C7—C81.446 (3)C22—H220.950
C7—C101.424 (3)C22—H230.950
C8—C91.403 (3)C23—H150.950
C10—C111.360 (3)C23—H160.950
C11—C171.439 (2)C23—H170.950
C12—C131.368 (3)C24—H240.951
C12—C171.422 (3)C24—H250.941
C13—C141.425 (3)
CL1···CL1i3.5843 (15)H8···O4xi3.566
CL1···C83.573 (2)H8···O5iv2.644
CL2···C163.584 (2)H8···C13iv3.453
CL2···C173.579 (2)H8···C14iv3.540
CL2···C19ii3.436 (2)H8···C22iv3.224
CL2···C23iii3.524 (3)H8···C22xi3.488
O1···O5iv3.247 (2)H8···H10iii3.098
O1···C23iv3.420 (3)H8···H17iv3.417
O1···C24i3.557 (5)H8···H19xiii3.417
O2···O4v3.554 (2)H8···H20xiii3.520
O2···C22v3.526 (3)H8···H21xi2.762
O2···C23iv3.547 (3)H8···H22iv2.965
O2···C24i3.325 (5)H9···CL1i3.343
O4···O2vi3.554 (2)H9···C4iii3.232
O4···C18vii3.338 (2)H9···C21xiii3.454
O4···C19vi3.531 (3)H9···H2iii2.824
O5···O1vii3.247 (2)H9···H3iii3.429
O5···C18vii3.337 (3)H9···H10iii3.153
N1···C24viii3.520 (3)H9···H18xiii3.261
C8···CL13.573 (2)H9···H19xiii3.462
C15···C21viii3.574 (3)H9···H20xiii3.082
C16···CL23.584 (2)H9···H24i3.565
C17···CL23.579 (2)H10···CL2ii3.227
C18···O4iv3.338 (2)H10···O4v2.916
C18···O5iv3.337 (3)H10···O5v3.159
C19···CL2ii3.436 (2)H10···C13v3.286
C19···O4v3.531 (3)H10···C14v3.391
C21···C15iii3.574 (3)H10···C18viii3.528
C22···O2vi3.526 (3)H10···H8viii3.098
C22···C22ix3.498 (3)H10···H9viii3.153
C23···CL2viii3.524 (3)H10···H23v3.465
C23···O1vii3.420 (3)H11···CL2ii3.125
C23···O2vii3.547 (3)H11···N1ii2.872
C24···O1i3.557 (5)H11···C5ii3.289
C24···O2i3.325 (5)H11···C6ii3.295
C24···N1iii3.520 (3)H11···H3ii3.506
CL1···H2ii3.075H11···H6ii3.476
CL1···H3iii3.109H11···H24i3.372
CL1···H3ii3.531H11···H25i3.364
CL1···H9i3.343H12···CL2ii3.386
CL2···H10ii3.227H12···C13v3.545
CL2···H11ii3.125H12···H17iv3.166
CL2···H12ii3.386H12···H24i3.419
CL2···H15iii3.086H13···N1iii3.089
CL2···H15x3.196H13···C6iii3.334
CL2···H16iii3.222H13···C15iii3.114
O1···H17iv2.746H13···C16iii3.325
O1···H21xi3.034H13···H6iii2.885
O1···H23v3.111H13···H14xiii3.450
O1···H24i2.773H13···H16iii3.422
O2···H17iv2.613H13···H18xiii2.979
O2···H23v2.911H14···C6xi3.256
O2···H24i2.512H14···C7xi2.899
O2···H25i3.393H14···C8xi3.277
O3···H16iii2.857H14···C10xi3.145
O3···H22ix3.587H14···H4xi3.466
O4···H8vii2.408H14···H13xiii3.450
O4···H8xi3.566H14···H18xiii2.859
O4···H10vi2.916H15···CL2viii3.086
O5···H8vii2.644H15···CL2x3.196
O5···H10vi3.159H15···H15xiv3.447
O5···H19viii3.404H15···H24x3.031
O5···H21xii3.404H15···H25viii3.389
O5···H22xii3.561H16···CL2viii3.222
O5···H24x3.598H16···O3viii2.857
N1···H11ii2.872H16···C11viii3.331
N1···H13viii3.089H16···C12viii3.254
N1···H25viii2.637H16···C17viii3.473
C1···H20xi3.303H16···C20viii3.564
C2···H20xi3.586H16···H5viii2.897
C2···H23v3.372H16···H13viii3.422
C2···H24i3.149H16···H19viii3.232
C3···H20xi3.528H16···H25viii3.550
C3···H22v3.577H17···O1vii2.746
C3···H23v3.281H17···O2vii2.613
C3···H24i3.024H17···C19vii3.437
C4···H3ii3.445H17···C24x3.552
C4···H9viii3.232H17···H5viii3.318
C4···H20xi3.187H17···H8vii3.417
C5···H2ii3.453H17···H12vii3.166
C5···H11ii3.289H17···H21xii3.559
C5···H20xi3.388H17···H23viii3.081
C5···H25viii3.137H17···H24x2.692
C6···H11ii3.295H18···C16iii3.596
C6···H13viii3.334H18···C18xiii3.479
C6···H14xi3.256H18···C20xiii3.332
C7···H14xi2.899H18···H1xiii3.234
C7···H20xi3.529H18···H4xiii3.194
C8···H14xi3.277H18···H7xiii2.881
C8···H20xi2.918H18···H9xiii3.261
C9···H20xi2.849H18···H13xiii2.979
C10···H14xi3.145H18···H14xiii2.859
C11···H16iii3.331H19···O5iii3.404
C12···H7xi3.035H19···C12iii3.551
C12···H16iii3.254H19···C13iii3.227
C12···H19viii3.551H19···C14iii2.867
C13···H7xi3.297H19···C15iii2.882
C13···H8vii3.453H19···C16iii3.246
C13···H10vi3.286H19···C17iii3.555
C13···H12vi3.545H19···C18xiii3.403
C13···H19viii3.227H19···H6iii3.229
C14···H8vii3.540H19···H7xiii2.816
C14···H10vi3.391H19···H8xiii3.417
C14···H19viii2.867H19···H9xiii3.462
C15···H13viii3.114H19···H16iii3.232
C15···H19viii2.882H19···H22ix2.743
C15···H25viii3.533H20···C1xi3.303
C16···H13viii3.325H20···C2xi3.586
C16···H18viii3.596H20···C3xi3.528
C16···H19viii3.246H20···C4xi3.187
C17···H16iii3.473H20···C5xi3.388
C17···H19viii3.555H20···C7xi3.529
C18···H10iii3.528H20···C8xi2.918
C18···H18xiii3.479H20···C9xi2.849
C18···H19xiii3.403H20···C18xiii3.441
C18···H20xiii3.441H20···H7xiii3.178
C18···H21xi3.046H20···H8xiii3.520
C19···H17iv3.437H20···H9xiii3.082
C19···H24i3.340H20···H22ix2.793
C20···H6iii3.545H21···O1xi3.034
C20···H16iii3.564H21···O5xii3.404
C20···H18xiii3.332H21···C18xi3.046
C21···H7xiii3.130H21···C22ix3.101
C21···H9xiii3.454H21···H5ix3.419
C21···H22ix3.193H21···H7xi2.892
C22···H5ix3.514H21···H8xi2.762
C22···H8vii3.224H21···H17xii3.559
C22···H8xi3.488H21···H21ix2.967
C22···H21ix3.101H21···H22ix3.365
C22···H23ix3.097H21···H23ix2.525
C23···H5viii3.530H22···O3ix3.587
C23···H24x3.204H22···O5xii3.561
C24···H3iii3.351H22···C3vi3.577
C24···H6iii3.414H22···C21ix3.193
C24···H17x3.552H22···H5ix3.147
H1···H18xiii3.234H22···H8vii2.965
H2···CL1ii3.075H22···H19ix2.743
H2···C5ii3.453H22···H20ix2.793
H2···H3ii3.462H22···H21ix3.365
H2···H9viii2.824H22···H23ix3.362
H3···CL1viii3.109H23···O1vi3.111
H3···CL1ii3.531H23···O2vi2.911
H3···C4ii3.445H23···C2vi3.372
H3···C24viii3.351H23···C3vi3.281
H3···H2ii3.462H23···C22ix3.097
H3···H9viii3.429H23···H5ix3.405
H3···H11ii3.506H23···H10vi3.465
H3···H25viii2.809H23···H17iii3.081
H4···H14xi3.466H23···H21ix2.525
H4···H18xiii3.194H23···H22ix3.362
H5···C22ix3.514H23···H23ix2.960
H5···C23iii3.530H24···O1i2.773
H5···H7xi2.991H24···O2i2.512
H5···H16iii2.897H24···O5x3.598
H5···H17iii3.318H24···C2i3.149
H5···H21ix3.419H24···C3i3.024
H5···H22ix3.147H24···C19i3.340
H5···H23ix3.405H24···C23x3.204
H6···C20viii3.545H24···H9i3.565
H6···C24viii3.414H24···H11i3.372
H6···H11ii3.476H24···H12i3.419
H6···H13viii2.885H24···H15x3.031
H6···H19viii3.229H24···H17x2.692
H6···H25viii2.618H25···O2i3.393
H7···C12xi3.035H25···N1iii2.637
H7···C13xi3.297H25···C5iii3.137
H7···C21xiii3.130H25···C15iii3.533
H7···H5xi2.991H25···H3iii2.809
H7···H18xiii2.881H25···H6iii2.618
H7···H19xiii2.816H25···H11i3.364
H7···H20xiii3.178H25···H15iii3.389
H7···H21xi2.892H25···H16iii3.550
H8···O4iv2.408
C2—O1—C18117.3 (2)C9—C4—H2119.8
C3—O2—C19116.52 (18)N1—C5—H3117.2
C11—O3—C20117.65 (18)C9—C5—H3117.4
C13—O4—C22117.39 (19)C7—C10—H4119.6
C14—O5—C23117.0 (2)C11—C10—H4119.5
C5—N1—C6117.22 (18)C13—C12—H5119.8
C2—C1—C8121.2 (2)C17—C12—H5119.9
O1—C2—C1125.2 (2)C14—C15—H6119.3
O1—C2—C3114.7 (2)C16—C15—H6119.3
C1—C2—C3120.10 (19)O1—C18—H7109.3
O2—C3—C2113.76 (18)O1—C18—H8109.5
O2—C3—C4126.8 (2)O1—C18—H9109.5
C2—C3—C4119.5 (2)H7—C18—H8109.2
C3—C4—C9120.5 (2)H7—C18—H9109.7
N1—C5—C9125.4 (2)H8—C18—H9109.5
N1—C6—C7123.3 (2)O2—C19—H10109.6
N1—C6—C16117.29 (18)O2—C19—H11109.6
C7—C6—C16119.40 (19)O2—C19—H12109.6
C6—C7—C8118.13 (19)H10—C19—H11109.3
C6—C7—C10119.9 (2)H10—C19—H12109.3
C8—C7—C10121.93 (18)H11—C19—H12109.4
C1—C8—C7123.47 (19)O3—C20—H13109.9
C1—C8—C9118.4 (2)O3—C20—H14110.1
C7—C8—C9118.11 (18)C21—C20—H13109.9
C4—C9—C5121.8 (2)C21—C20—H14109.8
C4—C9—C8120.37 (19)H13—C20—H14109.7
C5—C9—C8117.8 (2)C20—C21—H18109.4
C7—C10—C11120.88 (19)C20—C21—H19109.4
O3—C11—C10124.55 (18)C20—C21—H20109.6
O3—C11—C17114.4 (2)H18—C21—H19109.5
C10—C11—C17121.05 (19)H18—C21—H20109.5
C13—C12—C17120.2 (2)H19—C21—H20109.5
O4—C13—C12125.8 (2)O4—C22—H21109.4
O4—C13—C14113.77 (19)O4—C22—H22109.6
C12—C13—C14120.4 (2)O4—C22—H23109.5
O5—C14—C13114.6 (2)H21—C22—H22109.5
O5—C14—C15126.0 (2)H21—C22—H23109.5
C13—C14—C15119.38 (19)H22—C22—H23109.5
C14—C15—C16121.4 (2)O5—C23—H15109.4
C6—C16—C15121.4 (2)O5—C23—H16109.4
C6—C16—C17119.81 (18)O5—C23—H17109.6
C15—C16—C17118.8 (2)H15—C23—H16109.5
C11—C17—C12121.28 (19)H15—C23—H17109.5
C11—C17—C16118.9 (2)H16—C23—H17109.5
C12—C17—C16119.81 (18)CL1—C24—H24108.2
O3—C20—C21107.5 (2)CL1—C24—H25108.2
CL1—C24—CL2113.8 (2)CL2—C24—H24108.3
C2—C1—H1119.3CL2—C24—H25108.3
C8—C1—H1119.5H24—C24—H25110.2
C3—C4—H2119.8
C18—O1—C2—C17.6 (3)C16—C6—C7—C8−178.9 (2)
C18—O1—C2—C3−172.5 (2)C16—C6—C7—C100.5 (3)
C19—O2—C3—C2−179.2 (2)C6—C7—C8—C1178.0 (2)
C19—O2—C3—C41.1 (3)C6—C7—C8—C9−1.6 (3)
C11—O3—C20—C21177.49 (19)C6—C7—C10—C11−0.8 (3)
C20—O3—C11—C10−0.5 (3)C8—C7—C10—C11178.6 (2)
C20—O3—C11—C17178.95 (19)C10—C7—C8—C1−1.5 (3)
C22—O4—C13—C12−1.2 (3)C10—C7—C8—C9179.0 (2)
C22—O4—C13—C14179.1 (2)C1—C8—C9—C4−0.4 (3)
C23—O5—C14—C13173.6 (2)C1—C8—C9—C5−178.7 (2)
C23—O5—C14—C15−4.8 (3)C7—C8—C9—C4179.1 (2)
C5—N1—C6—C70.3 (3)C7—C8—C9—C50.8 (3)
C5—N1—C6—C16−179.8 (2)C7—C10—C11—O3179.6 (2)
C6—N1—C5—C9−1.2 (3)C7—C10—C11—C170.1 (2)
C2—C1—C8—C7−179.0 (2)O3—C11—C17—C120.6 (3)
C2—C1—C8—C90.5 (3)O3—C11—C17—C16−178.76 (19)
C8—C1—C2—O1−179.93 (18)C10—C11—C17—C12−179.9 (2)
C8—C1—C2—C30.1 (3)C10—C11—C17—C160.8 (3)
O1—C2—C3—O2−0.6 (3)C13—C12—C17—C11179.7 (2)
O1—C2—C3—C4179.1 (2)C13—C12—C17—C16−0.9 (3)
C1—C2—C3—O2179.4 (2)C17—C12—C13—O4−179.2 (2)
C1—C2—C3—C4−0.9 (3)C17—C12—C13—C140.6 (3)
O2—C3—C4—C9−179.3 (2)O4—C13—C14—O51.5 (3)
C2—C3—C4—C91.0 (3)O4—C13—C14—C15−179.98 (16)
C3—C4—C9—C5177.9 (2)C12—C13—C14—O5−178.3 (2)
C3—C4—C9—C8−0.3 (3)C12—C13—C14—C150.2 (3)
N1—C5—C9—C4−177.7 (2)O5—C14—C15—C16177.6 (2)
N1—C5—C9—C80.6 (3)C13—C14—C15—C16−0.7 (3)
N1—C6—C7—C81.1 (3)C14—C15—C16—C6−178.8 (2)
N1—C6—C7—C10−179.5 (2)C14—C15—C16—C170.4 (3)
N1—C6—C16—C15−0.4 (3)C6—C16—C17—C11−1.0 (3)
N1—C6—C16—C17−179.6 (2)C6—C16—C17—C12179.6 (2)
C7—C6—C16—C15179.6 (2)C15—C16—C17—C11179.8 (2)
C7—C6—C16—C170.3 (3)C15—C16—C17—C120.4 (3)
  2 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Palladium-catalyzed anilide ortho-arylation and subsequent one-pot cyclization to phenanthridines.

Authors:  Dmitry Shabashov; Olafs Daugulis
Journal:  J Org Chem       Date:  2007-09-07       Impact factor: 4.354
  2 in total

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