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A versatile synthetic method has been developed for the formation of variously substituted polycyclic pyrimidoazepine derivatives, formed by nucleophilic substitution reactions on the corresponding chloro-substituted compounds; the reactions can be promoted either by conventional heating in basic solutions or by microwave heating in solvent-free systems. Thus, (6RS)-6,11-dimethyl-3,5,6,11-tetra­hydro-4H-benzo[b]pyrimido[5,4-f]azepin-4-one, C14H15N3O, (I), was isolated from a solution containing (6RS)-4-chloro-8-hy­droxy-6,11-dimethyl-6,11-di­hydro-5H-benzo[b]pyrimido[5,4-f]azepine and benzene-1,2-di­amine; (6RS)-4-but­oxy-6,11-dimethyl-6,11-di­hydro-5H-benzo[b]pyrimido[5,4-f]azepin-8-ol, C18H23N3O2, (II), was formed by reaction of the corresponding 6-chloro compound with butanol, and (RS)-4-di­methyl­amino-6,11-dimethyl-6,11-di­hydro-5H-benzo[b]pyrimido[5,4-f]azepin-8-ol, C16H20N4O, (III), was formed by reaction of the chloro analogue with alkaline di­methyl­formamide. (6RS)-N-Benzyl-8-meth­oxy-6,11-dimethyl-6,11-di­hydro-5H-benzo[b]pyrimido[5,4-f]aze­pin-4-amine, C22H24N4O, (IV), (6RS)-N-benzyl-6-methyl-1,2,6,7-tetra­hydro­pyrimido[5′,4′:6,7]azepino[3,2,1-hi]indol-8-amine, C22H22N4, (V), and (7RS)-N-benzyl-7-methyl-2,3,7,8-tetra­hydro-1H-pyrimido[5′,4′:6,7]azepino[3,2,1-ij]quinolin-9-amine, C23H24N4, (VI), were all formed by reaction of the corresponding chloro compounds with benzyl­amine under microwave irradiation. In each of compounds (I)–(IV) and (VI), the azepine ring adopts a conformation close to the boat form, with the C-methyl group in a quasi-equatorial site, whereas the corresponding ring in (V) adopts a conformation inter­mediate between the twist-boat and twist-chair forms, with the C-methyl group in a quasi-axial site. No two of the structures of (I)–(VI) exhibit the same range of inter­molecular hydrogen bonds: different types of sheet are formed in each of (I), (II), (V) and (VI), and different types of chain in each of (III) and (IV).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616004654/yf3101sup1.cif
Contains datablocks global, I, II, III, IV, V, VI

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616004654/yf3101Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616004654/yf3101Isup8.cml
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616004654/yf3101IIsup3.hkl
Contains datablock II

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616004654/yf3101IIsup9.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616004654/yf3101IIIsup10.cml
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616004654/yf3101IIIsup4.hkl
Contains datablock III

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616004654/yf3101IVsup11.cml
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616004654/yf3101IVsup5.hkl
Contains datablock IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616004654/yf3101Vsup6.hkl
Contains datablock V

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616004654/yf3101VIsup7.hkl
Contains datablock VI

CCDC references: 1469144; 1469143; 1469142; 1469141; 1469140; 1469139

Computing details top

Data collection: COLLECT (Hooft, 1999) for (I); APEX2 (Bruker, 2007) for (II), (III), (IV), (V), (VI). Cell refinement: DIRAX/LSQ (Duisenberg et al., 2000) for (I); SAINT (Bruker, 2007) for (II), (III), (IV), (V), (VI). Data reduction: EVALCCD (Duisenberg et al., 2003) for (I); SAINT (Bruker, 2012) for (II), (III), (IV), (V), (VI). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

(I) 6,11-Dimethyl-3,5,6,11-tetrahydro-4H-benzo[b]pyrimido[5,4-f]azepin-4-one top
Crystal data top
C14H15N3OF(000) = 512
Mr = 241.29Dx = 1.369 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 17.0839 (16) ÅCell parameters from 2683 reflections
b = 4.2350 (3) Åθ = 2.7–27.5°
c = 16.2258 (18) ŵ = 0.09 mm1
β = 94.047 (8)°T = 120 K
V = 1171.01 (19) Å3Block, colourless
Z = 40.25 × 0.18 × 0.16 mm
Data collection top
Bruker–Nonius KappaCCD
diffractometer
2681 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode1502 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.115
φ and ω scansθmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 2122
Tmin = 0.851, Tmax = 0.986k = 55
17222 measured reflectionsl = 2020
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.061H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.141 w = 1/[σ2(Fo2) + (0.054P)2 + 0.5675P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2681 reflectionsΔρmax = 0.28 e Å3
168 parametersΔρmin = 0.27 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.08849 (12)0.4412 (5)0.30295 (13)0.0240 (5)
C20.02938 (15)0.3079 (7)0.33612 (16)0.0253 (6)
H20.01890.29400.30360.030*
N30.03210 (12)0.1899 (6)0.41247 (13)0.0230 (5)
H30.0079 (16)0.095 (7)0.4311 (17)0.028*
C40.09824 (14)0.2217 (6)0.46586 (15)0.0212 (6)
O40.09755 (10)0.1224 (5)0.53850 (11)0.0290 (5)
C4A0.16404 (14)0.3752 (6)0.43355 (14)0.0181 (6)
C50.23085 (13)0.4446 (6)0.49697 (15)0.0198 (6)
H5A0.25050.24110.52020.024*
H5B0.20950.56530.54260.024*
C60.30038 (13)0.6269 (6)0.46742 (14)0.0182 (6)
H60.28010.83370.44520.022*
C6A0.33746 (14)0.4584 (6)0.39826 (15)0.0189 (6)
C70.41255 (14)0.3254 (6)0.40727 (16)0.0220 (6)
H70.44070.33270.45980.026*
C80.44722 (14)0.1833 (6)0.34197 (16)0.0241 (6)
H80.49790.09120.35010.029*
C90.40718 (15)0.1773 (6)0.26497 (16)0.0238 (6)
H90.43070.08440.21950.029*
C100.33256 (14)0.3071 (6)0.25404 (15)0.0214 (6)
H100.30550.30350.20080.026*
C10A0.29676 (14)0.4426 (6)0.32008 (15)0.0185 (6)
N110.21940 (11)0.5721 (5)0.30672 (12)0.0186 (5)
C11A0.15830 (14)0.4585 (6)0.35098 (15)0.0192 (6)
C610.35772 (14)0.6979 (7)0.54163 (15)0.0230 (6)
H61A0.40300.81380.52320.034*
H61B0.37560.49930.56760.034*
H61C0.33140.82620.58170.034*
C1110.19808 (15)0.7032 (7)0.22439 (15)0.0236 (6)
H11A0.15820.86760.22870.035*
H11B0.17710.53490.18780.035*
H11C0.24470.79470.20180.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0169 (11)0.0323 (13)0.0221 (12)0.0030 (10)0.0028 (9)0.0020 (10)
C20.0167 (13)0.0376 (16)0.0214 (14)0.0021 (12)0.0007 (11)0.0014 (13)
N30.0148 (11)0.0351 (14)0.0193 (12)0.0062 (10)0.0018 (9)0.0048 (10)
C40.0164 (13)0.0259 (15)0.0213 (14)0.0003 (11)0.0013 (11)0.0011 (12)
O40.0201 (9)0.0470 (14)0.0199 (10)0.0077 (9)0.0023 (7)0.0072 (9)
C4A0.0164 (12)0.0215 (14)0.0166 (13)0.0003 (11)0.0014 (10)0.0006 (11)
C50.0183 (12)0.0226 (13)0.0186 (13)0.0002 (11)0.0017 (10)0.0024 (11)
C60.0171 (12)0.0217 (14)0.0155 (13)0.0028 (10)0.0004 (10)0.0021 (11)
C6A0.0193 (13)0.0178 (13)0.0199 (13)0.0044 (11)0.0036 (10)0.0016 (11)
C70.0196 (13)0.0246 (15)0.0216 (14)0.0044 (11)0.0004 (11)0.0030 (12)
C80.0160 (13)0.0268 (14)0.0300 (15)0.0004 (11)0.0051 (11)0.0004 (13)
C90.0248 (14)0.0262 (15)0.0214 (14)0.0014 (12)0.0093 (11)0.0028 (12)
C100.0240 (14)0.0226 (14)0.0176 (13)0.0058 (12)0.0021 (10)0.0000 (11)
C10A0.0180 (12)0.0178 (13)0.0196 (13)0.0049 (11)0.0015 (10)0.0007 (11)
N110.0179 (11)0.0234 (12)0.0145 (10)0.0034 (9)0.0006 (8)0.0028 (9)
C11A0.0180 (13)0.0197 (14)0.0201 (13)0.0005 (11)0.0031 (10)0.0028 (11)
C610.0217 (13)0.0275 (15)0.0194 (13)0.0053 (11)0.0009 (10)0.0028 (12)
C1110.0224 (13)0.0290 (15)0.0191 (13)0.0045 (12)0.0004 (11)0.0074 (12)
Geometric parameters (Å, º) top
N1—C21.306 (3)C7—C81.387 (4)
N1—C11A1.380 (3)C7—H70.9500
C2—N31.334 (3)C8—C91.382 (4)
C2—H20.9500C8—H80.9500
N3—C41.381 (3)C9—C101.388 (4)
N3—H30.86 (3)C9—H90.9500
C4—O41.252 (3)C10—C10A1.394 (3)
C4—C4A1.430 (3)C10—H100.9500
C4A—C11A1.382 (3)C10A—N111.433 (3)
C4A—C51.511 (3)N11—C11A1.394 (3)
C5—C61.522 (3)N11—C1111.469 (3)
C5—H5A0.9900C61—H61A0.9800
C5—H5B0.9900C61—H61B0.9800
C6—C6A1.507 (3)C61—H61C0.9800
C6—C611.528 (3)C111—H11A0.9800
C6—H61.0000C111—H11B0.9800
C6A—C71.399 (3)C111—H11C0.9800
C6A—C10A1.405 (3)
C2—N1—C11A116.9 (2)C9—C8—C7119.2 (2)
N1—C2—N3124.6 (2)C9—C8—H8120.4
N1—C2—H2117.7C7—C8—H8120.4
N3—C2—H2117.7C8—C9—C10120.0 (2)
C2—N3—C4121.3 (2)C8—C9—H9120.0
C2—N3—H3121.5 (18)C10—C9—H9120.0
C4—N3—H3117.2 (18)C9—C10—C10A120.9 (2)
O4—C4—N3119.7 (2)C9—C10—H10119.6
O4—C4—C4A123.9 (2)C10A—C10—H10119.6
N3—C4—C4A116.4 (2)C10—C10A—C6A119.9 (2)
C11A—C4A—C4117.9 (2)C10—C10A—N11119.4 (2)
C11A—C4A—C5127.5 (2)C6A—C10A—N11120.7 (2)
C4—C4A—C5114.5 (2)C11A—N11—C10A120.4 (2)
C4A—C5—C6116.9 (2)C11A—N11—C111116.90 (19)
C4A—C5—H5A108.1C10A—N11—C111116.69 (19)
C6—C5—H5A108.1N1—C11A—C4A122.2 (2)
C4A—C5—H5B108.1N1—C11A—N11112.1 (2)
C6—C5—H5B108.1C4A—C11A—N11125.7 (2)
H5A—C5—H5B107.3C6—C61—H61A109.5
C6A—C6—C5111.9 (2)C6—C61—H61B109.5
C6A—C6—C61113.6 (2)H61A—C61—H61B109.5
C5—C6—C61108.84 (19)C6—C61—H61C109.5
C6A—C6—H6107.4H61A—C61—H61C109.5
C5—C6—H6107.4H61B—C61—H61C109.5
C61—C6—H6107.4N11—C111—H11A109.5
C7—C6A—C10A117.8 (2)N11—C111—H11B109.5
C7—C6A—C6122.9 (2)H11A—C111—H11B109.5
C10A—C6A—C6119.2 (2)N11—C111—H11C109.5
C8—C7—C6A122.2 (2)H11A—C111—H11C109.5
C8—C7—H7118.9H11B—C111—H11C109.5
C6A—C7—H7118.9
C11A—N1—C2—N30.2 (4)C9—C10—C10A—C6A2.2 (4)
N1—C2—N3—C44.9 (4)C9—C10—C10A—N11179.5 (2)
C2—N3—C4—O4176.4 (3)C7—C6A—C10A—C102.2 (3)
C2—N3—C4—C4A2.6 (4)C6—C6A—C10A—C10175.5 (2)
O4—C4—C4A—C11A176.7 (3)C7—C6A—C10A—N11179.5 (2)
N3—C4—C4A—C11A4.4 (3)C6—C6A—C10A—N112.8 (3)
O4—C4—C4A—C56.8 (4)C10—C10A—N11—C11A121.3 (3)
N3—C4—C4A—C5172.1 (2)C6A—C10A—N11—C11A60.4 (3)
C11A—C4A—C5—C60.1 (4)C10—C10A—N11—C11130.6 (3)
C4—C4A—C5—C6176.1 (2)C6A—C10A—N11—C111147.7 (2)
C4A—C5—C6—C6A58.6 (3)C2—N1—C11A—C4A7.7 (4)
C4A—C5—C6—C61175.1 (2)C2—N1—C11A—N11173.3 (2)
C5—C6—C6A—C7111.9 (3)C4—C4A—C11A—N19.7 (4)
C61—C6—C6A—C711.8 (3)C5—C4A—C11A—N1166.2 (2)
C5—C6—C6A—C10A70.6 (3)C4—C4A—C11A—N11171.4 (2)
C61—C6—C6A—C10A165.7 (2)C5—C4A—C11A—N1112.7 (4)
C10A—C6A—C7—C80.5 (4)C10A—N11—C11A—N1141.6 (2)
C6—C6A—C7—C8177.1 (2)C111—N11—C11A—N110.3 (3)
C6A—C7—C8—C91.2 (4)C10A—N11—C11A—C4A39.5 (4)
C7—C8—C9—C101.2 (4)C111—N11—C11A—C4A168.7 (2)
C8—C9—C10—C10A0.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O4i0.87 (3)1.88 (3)2.745 (3)175 (3)
C2—H2···N1ii0.952.523.304 (3)140
Symmetry codes: (i) x, y, z+1; (ii) x, y1/2, z+1/2.
(II) 4-Butoxy-6,11-dimethyl-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepin-8-ol top
Crystal data top
C18H23N3O2F(000) = 672
Mr = 313.39Dx = 1.211 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 11.4233 (4) ÅCell parameters from 2981 reflections
b = 7.3707 (3) Åθ = 4.3–66.7°
c = 20.4624 (7) ŵ = 0.64 mm1
β = 93.561 (2)°T = 100 K
V = 1719.56 (11) Å3Block, colourless
Z = 40.14 × 0.12 × 0.12 mm
Data collection top
Bruker D8 Venture
diffractometer
2981 independent reflections
Radiation source: high brilliance microfocus sealed tube1931 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.058
φ and ω scansθmax = 66.7°, θmin = 4.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1313
Tmin = 0.776, Tmax = 0.926k = 88
15100 measured reflectionsl = 2324
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.050 w = 1/[σ2(Fo2) + (0.0517P)2 + 0.7285P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.125(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.27 e Å3
2981 reflectionsΔρmin = 0.24 e Å3
215 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0056 (5)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.04553 (18)0.7842 (3)0.52658 (9)0.0337 (5)
C20.1058 (2)0.8294 (4)0.47593 (11)0.0360 (6)
H20.07680.92930.45040.043*
N30.20316 (18)0.7500 (3)0.45668 (9)0.0327 (5)
C40.2386 (2)0.6061 (3)0.49265 (11)0.0300 (6)
C4A0.1849 (2)0.5437 (3)0.54795 (10)0.0289 (6)
C50.2318 (2)0.3718 (3)0.57956 (11)0.0345 (6)
H5A0.31420.39370.59550.041*
H5B0.23250.27690.54540.041*
C60.1659 (2)0.2967 (3)0.63673 (11)0.0338 (6)
H60.08310.27400.61980.041*
C6A0.1618 (2)0.4369 (3)0.69070 (11)0.0285 (6)
C70.2273 (2)0.4235 (3)0.75010 (11)0.0305 (6)
H70.28060.32540.75700.037*
C80.2165 (2)0.5504 (3)0.79962 (11)0.0294 (6)
C90.1374 (2)0.6907 (3)0.79041 (11)0.0306 (6)
H90.12660.77450.82480.037*
C100.0734 (2)0.7093 (3)0.73068 (10)0.0289 (6)
H100.02010.80750.72400.035*
C10A0.0872 (2)0.5848 (3)0.68071 (10)0.0274 (6)
N110.02281 (17)0.6077 (3)0.61835 (8)0.0296 (5)
C11A0.0873 (2)0.6441 (3)0.56392 (10)0.0293 (6)
O410.33093 (14)0.5083 (2)0.47471 (7)0.0333 (4)
C410.3787 (2)0.5467 (4)0.41240 (11)0.0348 (6)
H41A0.42820.65690.41570.042*
H41B0.31450.56720.37840.042*
C420.4504 (2)0.3862 (4)0.39495 (11)0.0347 (6)
H42A0.40250.27480.39750.042*
H42B0.51860.37460.42700.042*
C430.4938 (2)0.4031 (4)0.32635 (12)0.0378 (7)
H43A0.42540.41150.29430.045*
H43B0.53960.51660.32350.045*
C440.5694 (3)0.2447 (4)0.30838 (14)0.0533 (8)
H44A0.63930.23930.33860.080*
H44B0.59310.26020.26350.080*
H44C0.52470.13180.31140.080*
O810.28456 (15)0.5270 (2)0.85678 (7)0.0347 (5)
H810.261 (2)0.616 (4)0.8913 (13)0.052*
C610.2172 (3)0.1160 (4)0.65817 (12)0.0439 (7)
H61A0.30030.13140.67190.066*
H61B0.20950.03010.62160.066*
H61C0.17510.06920.69490.066*
C1110.0909 (2)0.6984 (4)0.62020 (12)0.0361 (7)
H11A0.07860.82830.62830.054*
H11B0.13460.64610.65540.054*
H11C0.13550.68160.57820.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0404 (13)0.0364 (12)0.0246 (11)0.0050 (10)0.0055 (9)0.0028 (9)
C20.0437 (16)0.0367 (15)0.0279 (13)0.0057 (13)0.0059 (12)0.0038 (11)
N30.0377 (13)0.0341 (12)0.0267 (11)0.0030 (10)0.0049 (9)0.0006 (9)
C40.0297 (14)0.0351 (15)0.0251 (12)0.0030 (12)0.0018 (11)0.0026 (11)
C4A0.0355 (14)0.0306 (14)0.0206 (12)0.0019 (12)0.0037 (10)0.0003 (10)
C50.0460 (16)0.0351 (15)0.0230 (12)0.0052 (13)0.0073 (11)0.0008 (11)
C60.0457 (16)0.0320 (14)0.0244 (12)0.0025 (13)0.0073 (11)0.0015 (11)
C6A0.0327 (14)0.0309 (14)0.0228 (12)0.0030 (12)0.0083 (10)0.0026 (10)
C70.0342 (14)0.0283 (14)0.0299 (13)0.0024 (12)0.0087 (11)0.0022 (11)
C80.0322 (14)0.0341 (14)0.0224 (12)0.0025 (12)0.0050 (10)0.0040 (11)
C90.0362 (15)0.0309 (14)0.0252 (12)0.0009 (12)0.0070 (10)0.0019 (10)
C100.0325 (14)0.0297 (14)0.0253 (12)0.0002 (11)0.0071 (10)0.0009 (10)
C10A0.0304 (14)0.0308 (14)0.0215 (12)0.0021 (12)0.0043 (10)0.0029 (10)
N110.0319 (12)0.0357 (12)0.0217 (10)0.0023 (10)0.0054 (9)0.0001 (9)
C11A0.0346 (15)0.0302 (14)0.0231 (12)0.0005 (12)0.0016 (10)0.0005 (11)
O410.0373 (10)0.0414 (10)0.0219 (8)0.0047 (9)0.0067 (7)0.0023 (7)
C410.0371 (15)0.0410 (15)0.0273 (13)0.0002 (13)0.0103 (11)0.0025 (11)
C420.0335 (14)0.0415 (16)0.0296 (13)0.0001 (13)0.0058 (11)0.0000 (12)
C430.0405 (16)0.0408 (16)0.0331 (14)0.0028 (13)0.0099 (12)0.0051 (12)
C440.0545 (19)0.0499 (19)0.0581 (19)0.0024 (16)0.0252 (15)0.0107 (16)
O810.0404 (11)0.0418 (11)0.0220 (9)0.0035 (9)0.0015 (7)0.0013 (8)
C610.0572 (19)0.0395 (17)0.0356 (14)0.0027 (15)0.0064 (13)0.0013 (12)
C1110.0323 (15)0.0463 (17)0.0305 (13)0.0038 (13)0.0076 (11)0.0020 (12)
Geometric parameters (Å, º) top
N1—C21.322 (3)C10—H100.9500
N1—C11A1.354 (3)C10A—N111.443 (3)
C2—N31.337 (3)N11—C11A1.399 (3)
C2—H20.9500N11—C1111.463 (3)
N3—C41.339 (3)O41—C411.445 (3)
C4—O411.347 (3)C41—C421.495 (3)
C4—C4A1.398 (3)C41—H41A0.9900
C4A—C11A1.394 (3)C41—H41B0.9900
C4A—C51.506 (3)C42—C431.523 (3)
C5—C61.533 (3)C42—H42A0.9900
C5—H5A0.9900C42—H42B0.9900
C5—H5B0.9900C43—C441.511 (4)
C6—C611.509 (3)C43—H43A0.9900
C6—C6A1.515 (3)C43—H43B0.9900
C6—H61.0000C44—H44A0.9800
C6A—C71.391 (3)C44—H44B0.9800
C6A—C10A1.391 (3)C44—H44C0.9800
C7—C81.391 (3)O81—H811.01 (3)
C7—H70.9500C61—H61A0.9800
C8—O811.375 (3)C61—H61B0.9800
C8—C91.378 (3)C61—H61C0.9800
C9—C101.392 (3)C111—H11A0.9800
C9—H90.9500C111—H11B0.9800
C10—C10A1.390 (3)C111—H11C0.9800
C2—N1—C11A116.9 (2)C10A—N11—C111115.79 (18)
N1—C2—N3127.1 (2)N1—C11A—C4A122.1 (2)
N1—C2—H2116.4N1—C11A—N11114.3 (2)
N3—C2—H2116.4C4A—C11A—N11123.6 (2)
C2—N3—C4114.4 (2)C4—O41—C41118.71 (18)
N3—C4—O41119.3 (2)O41—C41—C42107.4 (2)
N3—C4—C4A124.9 (2)O41—C41—H41A110.2
O41—C4—C4A115.8 (2)C42—C41—H41A110.2
C11A—C4A—C4114.4 (2)O41—C41—H41B110.2
C11A—C4A—C5127.9 (2)C42—C41—H41B110.2
C4—C4A—C5117.5 (2)H41A—C41—H41B108.5
C4A—C5—C6117.0 (2)C41—C42—C43111.7 (2)
C4A—C5—H5A108.1C41—C42—H42A109.3
C6—C5—H5A108.1C43—C42—H42A109.3
C4A—C5—H5B108.1C41—C42—H42B109.3
C6—C5—H5B108.1C43—C42—H42B109.3
H5A—C5—H5B107.3H42A—C42—H42B107.9
C61—C6—C6A114.8 (2)C44—C43—C42112.6 (2)
C61—C6—C5109.9 (2)C44—C43—H43A109.1
C6A—C6—C5110.4 (2)C42—C43—H43A109.1
C61—C6—H6107.2C44—C43—H43B109.1
C6A—C6—H6107.2C42—C43—H43B109.1
C5—C6—H6107.2H43A—C43—H43B107.8
C7—C6A—C10A118.4 (2)C43—C44—H44A109.5
C7—C6A—C6123.3 (2)C43—C44—H44B109.5
C10A—C6A—C6118.3 (2)H44A—C44—H44B109.5
C8—C7—C6A121.4 (2)C43—C44—H44C109.5
C8—C7—H7119.3H44A—C44—H44C109.5
C6A—C7—H7119.3H44B—C44—H44C109.5
O81—C8—C9122.8 (2)C8—O81—H81110.6 (15)
O81—C8—C7117.6 (2)C6—C61—H61A109.5
C9—C8—C7119.5 (2)C6—C61—H61B109.5
C8—C9—C10119.9 (2)H61A—C61—H61B109.5
C8—C9—H9120.0C6—C61—H61C109.5
C10—C9—H9120.0H61A—C61—H61C109.5
C10A—C10—C9120.2 (2)H61B—C61—H61C109.5
C10A—C10—H10119.9N11—C111—H11A109.5
C9—C10—H10119.9N11—C111—H11B109.5
C10—C10A—C6A120.4 (2)H11A—C111—H11B109.5
C10—C10A—N11119.9 (2)N11—C111—H11C109.5
C6A—C10A—N11119.7 (2)H11A—C111—H11C109.5
C11A—N11—C10A117.49 (19)H11B—C111—H11C109.5
C11A—N11—C111116.42 (19)
C11A—N1—C2—N31.1 (4)C9—C10—C10A—N11178.4 (2)
N1—C2—N3—C42.2 (4)C7—C6A—C10A—C104.1 (3)
C2—N3—C4—O41175.3 (2)C6—C6A—C10A—C10174.8 (2)
C2—N3—C4—C4A2.9 (3)C7—C6A—C10A—N11176.8 (2)
N3—C4—C4A—C11A0.4 (4)C6—C6A—C10A—N114.4 (3)
O41—C4—C4A—C11A177.9 (2)C10—C10A—N11—C11A114.5 (2)
N3—C4—C4A—C5175.8 (2)C6A—C10A—N11—C11A66.3 (3)
O41—C4—C4A—C52.5 (3)C10—C10A—N11—C11129.5 (3)
C11A—C4A—C5—C60.5 (4)C6A—C10A—N11—C111149.7 (2)
C4—C4A—C5—C6175.2 (2)C2—N1—C11A—C4A4.0 (3)
C4A—C5—C6—C61174.6 (2)C2—N1—C11A—N11177.3 (2)
C4A—C5—C6—C6A57.8 (3)C4—C4A—C11A—N13.2 (3)
C61—C6—C6A—C717.1 (3)C5—C4A—C11A—N1171.6 (2)
C5—C6—C6A—C7107.7 (3)C4—C4A—C11A—N11178.2 (2)
C61—C6—C6A—C10A161.7 (2)C5—C4A—C11A—N117.0 (4)
C5—C6—C6A—C10A73.5 (3)C10A—N11—C11A—N1132.0 (2)
C10A—C6A—C7—C82.2 (3)C111—N11—C11A—N111.8 (3)
C6—C6A—C7—C8176.7 (2)C10A—N11—C11A—C4A49.3 (3)
C6A—C7—C8—O81180.0 (2)C111—N11—C11A—C4A166.9 (2)
C6A—C7—C8—C91.4 (4)N3—C4—O41—C418.4 (3)
O81—C8—C9—C10178.3 (2)C4A—C4—O41—C41170.0 (2)
C7—C8—C9—C103.2 (3)C4—O41—C41—C42161.8 (2)
C8—C9—C10—C10A1.3 (4)O41—C41—C42—C43173.6 (2)
C9—C10—C10A—C6A2.4 (3)C41—C42—C43—C44178.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O81—H81···N3i1.01 (3)1.82 (3)2.825 (2)171 (2)
C2—H2···N1ii0.952.593.330 (4)135
C10—H10···Cg1iii0.952.853.743 (2)156
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x, y+2, z+1; (iii) x, y+1/2, z+3/2.
(III) 4-Dimethylamino-6,11-dimethyl-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepin-8-ol top
Crystal data top
C16H20N4ODx = 1.295 Mg m3
Mr = 284.36Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 3368 reflections
a = 18.886 (3) Åθ = 2.1–27.6°
b = 7.9898 (15) ŵ = 0.08 mm1
c = 19.335 (3) ÅT = 100 K
V = 2917.6 (8) Å3Block, colourless
Z = 80.14 × 0.12 × 0.12 mm
F(000) = 1216
Data collection top
Bruker D8 Venture
diffractometer
3367 independent reflections
Radiation source: high brilliance microfocus sealed tube2463 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.086
φ and ω scansθmax = 27.6°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 2422
Tmin = 0.851, Tmax = 0.990k = 108
26680 measured reflectionsl = 2324
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.054H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.125 w = 1/[σ2(Fo2) + (0.0497P)2 + 2.3537P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3367 reflectionsΔρmax = 0.38 e Å3
197 parametersΔρmin = 0.30 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.04780 (8)0.79803 (19)0.52021 (7)0.0177 (3)
C20.08206 (10)0.8796 (2)0.56877 (9)0.0193 (4)
H20.05550.90650.60900.023*
N30.14911 (8)0.92899 (19)0.56880 (7)0.0166 (3)
C40.18543 (9)0.9001 (2)0.50950 (9)0.0138 (4)
C4A0.15192 (9)0.8382 (2)0.44936 (9)0.0140 (4)
C50.18613 (10)0.8667 (2)0.37926 (9)0.0173 (4)
H5A0.22090.77630.37100.021*
H5B0.21260.97370.38080.021*
C60.13485 (10)0.8725 (2)0.31767 (9)0.0179 (4)
H60.09190.93730.33170.021*
C6A0.11285 (9)0.6941 (2)0.30312 (9)0.0151 (4)
C70.13781 (10)0.6056 (2)0.24613 (9)0.0172 (4)
H70.16820.65980.21400.021*
C80.11920 (10)0.4399 (2)0.23524 (9)0.0182 (4)
C90.07558 (10)0.3592 (2)0.28244 (9)0.0220 (4)
H90.06190.24620.27500.026*
C100.05222 (10)0.4446 (2)0.34042 (9)0.0194 (4)
H100.02320.38880.37320.023*
C10A0.07080 (9)0.6111 (2)0.35119 (9)0.0156 (4)
N110.04268 (8)0.6971 (2)0.41004 (7)0.0165 (3)
C11A0.08264 (9)0.7773 (2)0.45912 (9)0.0141 (4)
N40.25566 (8)0.94162 (19)0.51069 (7)0.0156 (3)
C410.28411 (10)1.0212 (2)0.57289 (9)0.0206 (4)
H41A0.28480.94000.61090.031*
H41B0.25421.11650.58570.031*
H41C0.33241.06050.56380.031*
C420.30805 (10)0.8396 (3)0.47434 (11)0.0248 (5)
H42A0.28450.74370.45270.037*
H42B0.34360.79950.50730.037*
H42C0.33120.90720.43860.037*
C610.16899 (11)0.9607 (3)0.25648 (10)0.0248 (4)
H61A0.13650.95860.21700.037*
H61B0.21310.90330.24410.037*
H61C0.17941.07700.26890.037*
O810.14351 (8)0.35198 (17)0.17950 (7)0.0241 (3)
H810.1532 (12)0.422 (3)0.1462 (13)0.036*
C1110.03182 (9)0.6633 (3)0.42602 (10)0.0198 (4)
H11A0.05270.76140.44860.030*
H11B0.03500.56660.45710.030*
H11C0.05750.63930.38310.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0180 (7)0.0191 (8)0.0160 (7)0.0002 (6)0.0046 (6)0.0008 (6)
C20.0245 (10)0.0178 (9)0.0155 (9)0.0004 (8)0.0062 (8)0.0014 (7)
N30.0213 (8)0.0153 (8)0.0133 (7)0.0009 (6)0.0013 (6)0.0005 (6)
C40.0190 (8)0.0089 (8)0.0134 (8)0.0006 (7)0.0010 (7)0.0020 (7)
C4A0.0163 (9)0.0129 (9)0.0128 (8)0.0007 (7)0.0014 (7)0.0010 (7)
C50.0197 (9)0.0184 (9)0.0140 (8)0.0065 (8)0.0037 (7)0.0023 (7)
C60.0220 (9)0.0174 (9)0.0143 (8)0.0031 (8)0.0022 (7)0.0017 (7)
C6A0.0157 (8)0.0169 (9)0.0128 (8)0.0016 (7)0.0041 (7)0.0027 (7)
C70.0201 (9)0.0199 (10)0.0115 (8)0.0041 (8)0.0014 (7)0.0031 (7)
C80.0246 (10)0.0198 (10)0.0101 (8)0.0003 (8)0.0032 (7)0.0003 (7)
C90.0275 (10)0.0175 (10)0.0210 (9)0.0065 (8)0.0035 (8)0.0005 (8)
C100.0200 (9)0.0211 (10)0.0172 (9)0.0069 (8)0.0009 (8)0.0033 (8)
C10A0.0136 (8)0.0207 (10)0.0124 (8)0.0017 (7)0.0032 (7)0.0014 (7)
N110.0131 (7)0.0217 (8)0.0148 (7)0.0043 (6)0.0011 (6)0.0007 (6)
C11A0.0168 (9)0.0129 (8)0.0127 (8)0.0011 (7)0.0011 (7)0.0021 (7)
N40.0162 (7)0.0155 (8)0.0150 (7)0.0018 (6)0.0007 (6)0.0018 (6)
C410.0250 (10)0.0201 (10)0.0167 (9)0.0066 (8)0.0040 (8)0.0004 (8)
C420.0171 (9)0.0246 (11)0.0327 (11)0.0006 (8)0.0026 (8)0.0049 (9)
C610.0317 (11)0.0221 (10)0.0205 (9)0.0034 (9)0.0046 (9)0.0046 (8)
O810.0408 (8)0.0179 (7)0.0138 (6)0.0023 (6)0.0016 (6)0.0001 (6)
C1110.0124 (8)0.0268 (11)0.0204 (9)0.0014 (8)0.0011 (7)0.0029 (8)
Geometric parameters (Å, º) top
N1—C21.313 (2)C9—H90.9500
N1—C11A1.362 (2)C10—C10A1.392 (3)
C2—N31.326 (2)C10—H100.9500
C2—H20.9500C10A—N111.431 (2)
N3—C41.356 (2)N11—C11A1.371 (2)
C4—N41.367 (2)N11—C1111.466 (2)
C4—C4A1.413 (2)N4—C421.462 (2)
C4A—C11A1.409 (2)N4—C411.463 (2)
C4A—C51.519 (2)C41—H41A0.9800
C5—C61.536 (2)C41—H41B0.9800
C5—H5A0.9900C41—H41C0.9800
C5—H5B0.9900C42—H42A0.9800
C6—C6A1.511 (3)C42—H42B0.9800
C6—C611.520 (2)C42—H42C0.9800
C6—H61.0000C61—H61A0.9800
C6A—C10A1.391 (2)C61—H61B0.9800
C6A—C71.392 (2)C61—H61C0.9800
C7—C81.386 (3)O81—H810.87 (3)
C7—H70.9500C111—H11A0.9800
C8—O811.366 (2)C111—H11B0.9800
C8—C91.388 (3)C111—H11C0.9800
C9—C101.384 (3)
C2—N1—C11A116.26 (15)C6A—C10A—C10119.98 (17)
N1—C2—N3128.19 (17)C6A—C10A—N11120.96 (16)
N1—C2—H2115.9C10—C10A—N11118.96 (16)
N3—C2—H2115.9C11A—N11—C10A124.76 (14)
C2—N3—C4115.59 (15)C11A—N11—C111117.93 (14)
N3—C4—N4115.79 (15)C10A—N11—C111115.82 (14)
N3—C4—C4A121.92 (16)N1—C11A—N11113.03 (15)
N4—C4—C4A122.22 (15)N1—C11A—C4A121.50 (16)
C11A—C4A—C4115.26 (15)N11—C11A—C4A125.45 (15)
C11A—C4A—C5124.50 (15)C4—N4—C42120.86 (15)
C4—C4A—C5119.44 (15)C4—N4—C41118.40 (14)
C4A—C5—C6115.37 (15)C42—N4—C41112.90 (15)
C4A—C5—H5A108.4N4—C41—H41A109.5
C6—C5—H5A108.4N4—C41—H41B109.5
C4A—C5—H5B108.4H41A—C41—H41B109.5
C6—C5—H5B108.4N4—C41—H41C109.5
H5A—C5—H5B107.5H41A—C41—H41C109.5
C6A—C6—C61114.13 (15)H41B—C41—H41C109.5
C6A—C6—C5106.83 (15)N4—C42—H42A109.5
C61—C6—C5110.48 (15)N4—C42—H42B109.5
C6A—C6—H6108.4H42A—C42—H42B109.5
C61—C6—H6108.4N4—C42—H42C109.5
C5—C6—H6108.4H42A—C42—H42C109.5
C10A—C6A—C7118.70 (17)H42B—C42—H42C109.5
C10A—C6A—C6118.84 (16)C6—C61—H61A109.5
C7—C6A—C6122.26 (16)C6—C61—H61B109.5
C8—C7—C6A121.33 (17)H61A—C61—H61B109.5
C8—C7—H7119.3C6—C61—H61C109.5
C6A—C7—H7119.3H61A—C61—H61C109.5
O81—C8—C7121.72 (17)H61B—C61—H61C109.5
O81—C8—C9118.65 (17)C8—O81—H81108.7 (16)
C7—C8—C9119.63 (17)N11—C111—H11A109.5
C10—C9—C8119.50 (18)N11—C111—H11B109.5
C10—C9—H9120.2H11A—C111—H11B109.5
C8—C9—H9120.2N11—C111—H11C109.5
C9—C10—C10A120.80 (17)H11A—C111—H11C109.5
C9—C10—H10119.6H11B—C111—H11C109.5
C10A—C10—H10119.6
C11A—N1—C2—N38.0 (3)C6—C6A—C10A—C10177.35 (16)
N1—C2—N3—C44.2 (3)C7—C6A—C10A—N11178.83 (15)
C2—N3—C4—N4176.23 (16)C6—C6A—C10A—N116.3 (2)
C2—N3—C4—C4A6.6 (2)C9—C10—C10A—C6A0.5 (3)
N3—C4—C4A—C11A12.4 (2)C9—C10—C10A—N11176.97 (16)
N4—C4—C4A—C11A170.66 (16)C6A—C10A—N11—C11A58.5 (2)
N3—C4—C4A—C5157.82 (16)C10—C10A—N11—C11A125.05 (19)
N4—C4—C4A—C519.2 (3)C6A—C10A—N11—C111135.75 (17)
C11A—C4A—C5—C616.5 (3)C10—C10A—N11—C11140.7 (2)
C4—C4A—C5—C6152.75 (17)C2—N1—C11A—N11177.55 (16)
C4A—C5—C6—C6A75.52 (19)C2—N1—C11A—C4A0.8 (3)
C4A—C5—C6—C61159.81 (16)C10A—N11—C11A—N1158.61 (16)
C61—C6—C6A—C10A169.43 (16)C111—N11—C11A—N16.8 (2)
C5—C6—C6A—C10A68.1 (2)C10A—N11—C11A—C4A23.1 (3)
C61—C6—C6A—C715.9 (2)C111—N11—C11A—C4A171.49 (17)
C5—C6—C6A—C7106.56 (18)C4—C4A—C11A—N18.4 (2)
C10A—C6A—C7—C82.7 (3)C5—C4A—C11A—N1161.18 (17)
C6—C6A—C7—C8177.38 (17)C4—C4A—C11A—N11173.38 (17)
C6A—C7—C8—O81179.92 (16)C5—C4A—C11A—N1117.0 (3)
C6A—C7—C8—C90.9 (3)N3—C4—N4—C42143.42 (17)
O81—C8—C9—C10177.96 (16)C4A—C4—N4—C4239.4 (2)
C7—C8—C9—C101.1 (3)N3—C4—N4—C413.6 (2)
C8—C9—C10—C10A1.3 (3)C4A—C4—N4—C41173.59 (16)
C7—C6A—C10A—C102.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O81—H81···N3i0.87 (2)1.91 (2)2.767 (2)165 (2)
Symmetry code: (i) x, y+3/2, z1/2.
(IV) N-Benzyl-8-methoxy-6,11-dimethyl-6,11-dihydro-5H- benzo[b]pyrimido[5,4-f]azepin-4-amine top
Crystal data top
C22H24N4OF(000) = 768
Mr = 360.45Dx = 1.321 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.2994 (8) ÅCell parameters from 4129 reflections
b = 9.1501 (5) Åθ = 2.6–27.5°
c = 16.1710 (9) ŵ = 0.08 mm1
β = 95.289 (2)°T = 120 K
V = 1812.15 (18) Å3Block, colourless
Z = 40.12 × 0.10 × 0.10 mm
Data collection top
Bruker D8 Venture
diffractometer
4129 independent reflections
Radiation source: high brilliance microfocus sealed tube2975 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.054
φ and ω scansθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1515
Tmin = 0.810, Tmax = 0.992k = 1111
17697 measured reflectionsl = 2018
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.0492P)2 + 0.6796P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
4129 reflectionsΔρmax = 0.27 e Å3
250 parametersΔρmin = 0.31 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.75768 (11)0.99419 (15)0.32499 (8)0.0225 (3)
C20.69211 (14)1.05234 (18)0.26418 (10)0.0245 (4)
H20.72541.11920.22930.029*
N30.58567 (11)1.02960 (15)0.24529 (8)0.0234 (3)
C40.53870 (13)0.94285 (17)0.29928 (9)0.0203 (3)
C4A0.59727 (12)0.87925 (16)0.36957 (9)0.0181 (3)
C50.53193 (12)0.80706 (17)0.43256 (9)0.0203 (3)
H5A0.50640.71130.40990.024*
H5B0.46630.86760.43830.024*
C60.58936 (12)0.78159 (17)0.51958 (9)0.0188 (3)
H60.62640.87450.53870.023*
C6A0.67552 (12)0.66548 (17)0.51472 (9)0.0178 (3)
C70.66718 (12)0.52862 (16)0.54999 (9)0.0185 (3)
H70.60700.50810.58100.022*
C80.74465 (13)0.42021 (17)0.54131 (9)0.0195 (3)
C90.83323 (13)0.44871 (18)0.49662 (10)0.0217 (3)
H90.88660.37550.49020.026*
C100.84261 (13)0.58612 (18)0.46132 (9)0.0215 (3)
H100.90320.60610.43060.026*
C10A0.76574 (12)0.69503 (17)0.46976 (9)0.0182 (3)
N110.78283 (10)0.83762 (14)0.43713 (8)0.0198 (3)
C11A0.70991 (13)0.90192 (16)0.37663 (9)0.0191 (3)
N410.42875 (11)0.92135 (16)0.28584 (8)0.0246 (3)
H410.4009 (15)0.850 (2)0.3140 (12)0.030*
C470.35857 (14)0.9848 (2)0.21697 (11)0.0323 (4)
H47A0.34670.91240.17150.039*
H47B0.39481.07140.19510.039*
C410.25032 (13)1.02897 (19)0.24581 (9)0.0231 (4)
C420.15889 (14)0.93957 (19)0.23225 (10)0.0267 (4)
H420.16400.84980.20340.032*
C430.06023 (14)0.9806 (2)0.26057 (11)0.0295 (4)
H430.00170.91890.25080.035*
C440.05150 (14)1.1104 (2)0.30279 (11)0.0290 (4)
H440.01611.13810.32220.035*
C450.14194 (15)1.20014 (19)0.31663 (11)0.0287 (4)
H450.13671.28940.34600.034*
C460.24011 (14)1.15986 (19)0.28766 (10)0.0255 (4)
H460.30141.22290.29660.031*
C610.50284 (13)0.74562 (18)0.57861 (10)0.0213 (3)
H61A0.53850.72600.63420.032*
H61B0.46160.65920.55830.032*
H61C0.45300.82870.58110.032*
O810.72694 (9)0.28897 (11)0.57929 (7)0.0228 (3)
C810.78753 (14)0.16654 (18)0.55387 (11)0.0270 (4)
H81A0.86530.18100.57120.040*
H81B0.77700.15700.49330.040*
H81C0.76200.07750.57970.040*
C1110.89737 (13)0.88409 (18)0.43998 (10)0.0249 (4)
H11A0.90090.99100.43840.037*
H11B0.93050.84370.39210.037*
H11C0.93720.84850.49130.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0265 (7)0.0208 (7)0.0207 (7)0.0032 (6)0.0048 (6)0.0013 (6)
C20.0317 (10)0.0227 (9)0.0201 (8)0.0029 (7)0.0068 (7)0.0021 (7)
N30.0279 (8)0.0230 (7)0.0200 (7)0.0002 (6)0.0052 (6)0.0011 (6)
C40.0257 (8)0.0169 (8)0.0190 (8)0.0007 (6)0.0051 (6)0.0032 (6)
C4A0.0216 (8)0.0152 (7)0.0179 (7)0.0013 (6)0.0034 (6)0.0008 (6)
C50.0200 (8)0.0202 (8)0.0211 (8)0.0006 (6)0.0034 (6)0.0025 (6)
C60.0204 (8)0.0166 (8)0.0197 (8)0.0014 (6)0.0039 (6)0.0003 (6)
C6A0.0199 (8)0.0193 (8)0.0140 (7)0.0015 (6)0.0002 (6)0.0035 (6)
C70.0187 (8)0.0203 (8)0.0166 (7)0.0025 (6)0.0025 (6)0.0018 (6)
C80.0232 (8)0.0188 (8)0.0161 (7)0.0007 (6)0.0004 (6)0.0011 (6)
C90.0213 (8)0.0227 (8)0.0211 (8)0.0038 (7)0.0023 (6)0.0016 (7)
C100.0198 (8)0.0260 (9)0.0189 (8)0.0004 (7)0.0035 (6)0.0011 (7)
C10A0.0206 (8)0.0190 (8)0.0148 (7)0.0018 (6)0.0008 (6)0.0011 (6)
N110.0188 (7)0.0196 (7)0.0212 (7)0.0032 (5)0.0034 (5)0.0015 (5)
C11A0.0253 (8)0.0152 (7)0.0172 (7)0.0000 (6)0.0047 (6)0.0031 (6)
N410.0225 (7)0.0294 (8)0.0220 (7)0.0020 (6)0.0018 (6)0.0058 (6)
C470.0282 (9)0.0492 (12)0.0196 (8)0.0097 (8)0.0028 (7)0.0055 (8)
C410.0234 (8)0.0296 (9)0.0160 (8)0.0029 (7)0.0000 (6)0.0066 (7)
C420.0341 (10)0.0247 (9)0.0206 (8)0.0002 (7)0.0004 (7)0.0010 (7)
C430.0267 (9)0.0329 (10)0.0282 (9)0.0078 (8)0.0004 (7)0.0064 (8)
C440.0251 (9)0.0357 (10)0.0264 (9)0.0056 (8)0.0037 (7)0.0075 (8)
C450.0367 (10)0.0238 (9)0.0252 (9)0.0056 (8)0.0003 (7)0.0002 (7)
C460.0249 (9)0.0272 (9)0.0231 (8)0.0034 (7)0.0047 (7)0.0061 (7)
C610.0221 (8)0.0222 (8)0.0201 (8)0.0002 (7)0.0047 (6)0.0025 (7)
O810.0271 (6)0.0164 (6)0.0258 (6)0.0020 (5)0.0068 (5)0.0018 (5)
C810.0326 (10)0.0201 (9)0.0288 (9)0.0054 (7)0.0059 (7)0.0013 (7)
C1110.0210 (9)0.0268 (9)0.0269 (9)0.0048 (7)0.0022 (7)0.0019 (7)
Geometric parameters (Å, º) top
N1—C21.325 (2)N11—C1111.4681 (19)
N1—C11A1.3585 (19)N41—C471.465 (2)
C2—N31.333 (2)N41—H410.883 (19)
C2—H20.9500C47—C411.506 (2)
N3—C41.349 (2)C47—H47A0.9900
C4—N411.364 (2)C47—H47B0.9900
C4—C4A1.414 (2)C41—C461.387 (2)
C4A—C11A1.395 (2)C41—C421.392 (2)
C4A—C51.507 (2)C42—C431.388 (2)
C5—C61.533 (2)C42—H420.9500
C5—H5A0.9900C43—C441.379 (3)
C5—H5B0.9900C43—H430.9500
C6—C6A1.508 (2)C44—C451.384 (3)
C6—C611.529 (2)C44—H440.9500
C6—H61.0000C45—C461.385 (2)
C6A—C71.384 (2)C45—H450.9500
C6A—C10A1.408 (2)C46—H460.9500
C7—C81.391 (2)C61—H61A0.9800
C7—H70.9500C61—H61B0.9800
C8—O811.3752 (18)C61—H61C0.9800
C8—C91.386 (2)O81—C811.4268 (19)
C9—C101.390 (2)C81—H81A0.9800
C9—H90.9500C81—H81B0.9800
C10—C10A1.389 (2)C81—H81C0.9800
C10—H100.9500C111—H11A0.9800
C10A—N111.430 (2)C111—H11B0.9800
N11—C11A1.395 (2)C111—H11C0.9800
C2—N1—C11A115.96 (14)C4—N41—C47124.76 (14)
N1—C2—N3128.71 (15)C4—N41—H41116.8 (12)
N1—C2—H2115.6C47—N41—H41117.1 (12)
N3—C2—H2115.6N41—C47—C41110.29 (13)
C2—N3—C4114.44 (14)N41—C47—H47A109.6
N3—C4—N41117.34 (14)C41—C47—H47A109.6
N3—C4—C4A123.08 (14)N41—C47—H47B109.6
N41—C4—C4A119.54 (14)C41—C47—H47B109.6
C11A—C4A—C4115.67 (14)H47A—C47—H47B108.1
C11A—C4A—C5126.68 (14)C46—C41—C42118.44 (15)
C4—C4A—C5117.38 (13)C46—C41—C47120.35 (16)
C4A—C5—C6117.25 (13)C42—C41—C47121.20 (16)
C4A—C5—H5A108.0C43—C42—C41120.50 (16)
C6—C5—H5A108.0C43—C42—H42119.8
C4A—C5—H5B108.0C41—C42—H42119.8
C6—C5—H5B108.0C44—C43—C42120.45 (16)
H5A—C5—H5B107.2C44—C43—H43119.8
C6A—C6—C61114.44 (13)C42—C43—H43119.8
C6A—C6—C5109.02 (12)C43—C44—C45119.53 (16)
C61—C6—C5108.51 (12)C43—C44—H44120.2
C6A—C6—H6108.2C45—C44—H44120.2
C61—C6—H6108.2C44—C45—C46120.03 (16)
C5—C6—H6108.2C44—C45—H45120.0
C7—C6A—C10A118.59 (14)C46—C45—H45120.0
C7—C6A—C6122.48 (13)C45—C46—C41121.05 (16)
C10A—C6A—C6118.87 (13)C45—C46—H46119.5
C6A—C7—C8121.74 (14)C41—C46—H46119.5
C6A—C7—H7119.1C6—C61—H61A109.5
C8—C7—H7119.1C6—C61—H61B109.5
O81—C8—C9124.15 (14)H61A—C61—H61B109.5
O81—C8—C7116.06 (13)C6—C61—H61C109.5
C9—C8—C7119.79 (14)H61A—C61—H61C109.5
C8—C9—C10118.89 (15)H61B—C61—H61C109.5
C8—C9—H9120.6C8—O81—C81116.65 (12)
C10—C9—H9120.6O81—C81—H81A109.5
C10A—C10—C9121.71 (14)O81—C81—H81B109.5
C10A—C10—H10119.1H81A—C81—H81B109.5
C9—C10—H10119.1O81—C81—H81C109.5
C10—C10A—C6A119.28 (14)H81A—C81—H81C109.5
C10—C10A—N11119.59 (13)H81B—C81—H81C109.5
C6A—C10A—N11121.02 (13)N11—C111—H11A109.5
C11A—N11—C10A122.46 (13)N11—C111—H11B109.5
C11A—N11—C111116.92 (13)H11A—C111—H11B109.5
C10A—N11—C111115.20 (13)N11—C111—H11C109.5
N1—C11A—N11114.00 (13)H11A—C111—H11C109.5
N1—C11A—C4A121.64 (14)H11B—C111—H11C109.5
N11—C11A—C4A124.34 (14)
C11A—N1—C2—N32.0 (2)C10—C10A—N11—C11A120.11 (16)
N1—C2—N3—C44.7 (2)C6A—C10A—N11—C11A63.8 (2)
C2—N3—C4—N41176.72 (14)C10—C10A—N11—C11133.1 (2)
C2—N3—C4—C4A0.9 (2)C6A—C10A—N11—C111143.05 (15)
N3—C4—C4A—C11A5.0 (2)C2—N1—C11A—N11176.95 (13)
N41—C4—C4A—C11A177.49 (14)C2—N1—C11A—C4A4.8 (2)
N3—C4—C4A—C5169.47 (14)C10A—N11—C11A—N1149.18 (13)
N41—C4—C4A—C58.1 (2)C111—N11—C11A—N13.57 (19)
C11A—C4A—C5—C612.5 (2)C10A—N11—C11A—C4A32.6 (2)
C4—C4A—C5—C6161.25 (14)C111—N11—C11A—C4A174.61 (14)
C4A—C5—C6—C6A69.32 (17)C4—C4A—C11A—N17.9 (2)
C4A—C5—C6—C61165.45 (13)C5—C4A—C11A—N1165.94 (14)
C61—C6—C6A—C79.9 (2)C4—C4A—C11A—N11174.03 (14)
C5—C6—C6A—C7111.75 (16)C5—C4A—C11A—N1112.1 (2)
C61—C6—C6A—C10A172.72 (14)N3—C4—N41—C470.4 (2)
C5—C6—C6A—C10A65.58 (17)C4A—C4—N41—C47178.04 (15)
C10A—C6A—C7—C80.7 (2)C4—N41—C47—C41141.85 (16)
C6—C6A—C7—C8176.65 (14)N41—C47—C41—C4680.7 (2)
C6A—C7—C8—O81179.95 (13)N41—C47—C41—C4298.48 (19)
C6A—C7—C8—C90.3 (2)C46—C41—C42—C430.4 (2)
O81—C8—C9—C10179.69 (14)C47—C41—C42—C43178.80 (15)
C7—C8—C9—C100.1 (2)C41—C42—C43—C440.2 (2)
C8—C9—C10—C10A0.0 (2)C42—C43—C44—C450.2 (3)
C9—C10—C10A—C6A0.4 (2)C43—C44—C45—C460.5 (3)
C9—C10—C10A—N11175.77 (14)C44—C45—C46—C411.1 (2)
C7—C6A—C10A—C100.7 (2)C42—C41—C46—C451.1 (2)
C6—C6A—C10A—C10176.69 (14)C47—C41—C46—C45178.18 (15)
C7—C6A—C10A—N11175.40 (14)C9—C8—O81—C8116.1 (2)
C6—C6A—C10A—N117.2 (2)C7—C8—O81—C81164.17 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O81i0.952.573.386 (2)144
C45—H45···Cg1ii0.952.993.7583 (19)139
C46—H46···Cg2iii0.952.993.7583 (19)139
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x+1, y+2, z+1; (iii) x+1, y+1/2, z+1/2.
(V) N-Benzyl-6-methyl-1,2,6,7-tetrahydropyrimido[5',4':6,7]azepino[3,2,1-hi]indol-8-amine top
Crystal data top
C22H22N4F(000) = 364
Mr = 342.44Dx = 1.298 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
a = 7.7594 (4) ÅCell parameters from 3037 reflections
b = 8.5383 (6) Åθ = 5.8–66.7°
c = 13.4525 (8) ŵ = 0.61 mm1
β = 100.483 (3)°T = 120 K
V = 876.38 (9) Å3Block, colourless
Z = 20.14 × 0.12 × 0.09 mm
Data collection top
Bruker D8 Venture
diffractometer
3037 independent reflections
Radiation source: high brilliance microfocus sealed tube2972 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.023
φ and ω scansθmax = 66.7°, θmin = 5.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 99
Tmin = 0.847, Tmax = 0.946k = 1010
11308 measured reflectionsl = 1315
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.030 w = 1/[σ2(Fo2) + (0.0471P)2 + 0.1235P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.078(Δ/σ)max < 0.001
S = 1.09Δρmax = 0.13 e Å3
3037 reflectionsΔρmin = 0.16 e Å3
239 parametersAbsolute structure: Flack x determined using 1344 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute structure parameter: 0.11 (15)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.9711 (3)0.4769 (2)0.63564 (15)0.0225 (4)
H1A1.09300.50880.63340.027*
H1B0.95510.36620.61390.027*
C20.9309 (3)0.4984 (3)0.74184 (15)0.0263 (5)
H2A0.93190.39660.77730.032*
H2B1.01670.56950.78260.032*
C2A0.7500 (3)0.5692 (2)0.72271 (15)0.0215 (4)
C2B0.7065 (3)0.6209 (2)0.62191 (15)0.0189 (4)
C30.6354 (3)0.5884 (2)0.78933 (15)0.0251 (4)
H30.66530.55170.85700.030*
C40.4750 (3)0.6625 (2)0.75572 (16)0.0260 (5)
H40.39370.67550.80000.031*
C50.4355 (3)0.7167 (2)0.65737 (15)0.0230 (4)
H50.32700.76910.63610.028*
C5A0.5480 (2)0.6983 (2)0.58739 (14)0.0196 (4)
C60.4924 (2)0.7680 (2)0.48346 (14)0.0191 (4)
H60.42640.86600.49260.023*
C70.6523 (2)0.8183 (2)0.43823 (14)0.0195 (4)
H7A0.61270.89130.38150.023*
H7B0.73470.87600.49040.023*
C7A0.7484 (2)0.6849 (2)0.40052 (14)0.0188 (4)
C80.7593 (2)0.6641 (2)0.29771 (14)0.0206 (4)
N90.8576 (2)0.5504 (2)0.26604 (12)0.0230 (4)
C100.9481 (2)0.4622 (2)0.33878 (15)0.0218 (4)
H101.02170.38520.31720.026*
N110.9494 (2)0.46753 (19)0.43733 (12)0.0209 (4)
C11A0.8440 (2)0.5786 (2)0.46714 (14)0.0184 (4)
N120.8439 (2)0.57966 (19)0.57005 (12)0.0187 (3)
C610.3671 (2)0.6644 (2)0.41068 (15)0.0233 (4)
H61A0.42830.56890.39630.035*
H61B0.32670.72150.34750.035*
H61C0.26620.63650.44150.035*
N810.6761 (2)0.7646 (2)0.22618 (13)0.0271 (4)
H810.609 (3)0.830 (3)0.2442 (19)0.033*
C870.6467 (3)0.7349 (3)0.11770 (15)0.0290 (5)
H87A0.70860.63780.10450.035*
H87B0.69530.82250.08330.035*
C810.4535 (3)0.7179 (3)0.07542 (15)0.0253 (4)
C820.3479 (3)0.6203 (3)0.12198 (18)0.0350 (5)
H820.39870.56010.17920.042*
C830.1696 (4)0.6108 (4)0.0853 (2)0.0481 (7)
H830.09830.54570.11840.058*
C840.0945 (3)0.6954 (4)0.00074 (18)0.0477 (7)
H840.02780.68760.02450.057*
C850.1973 (3)0.7908 (3)0.04666 (17)0.0384 (6)
H850.14640.84870.10490.046*
C860.3760 (3)0.8023 (3)0.00906 (15)0.0285 (5)
H860.44620.86910.04180.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0191 (9)0.0241 (10)0.0234 (10)0.0048 (8)0.0015 (7)0.0020 (8)
C20.0244 (10)0.0305 (11)0.0233 (10)0.0015 (8)0.0023 (8)0.0012 (9)
C2A0.0232 (10)0.0200 (9)0.0208 (9)0.0010 (8)0.0032 (7)0.0016 (8)
C2B0.0193 (9)0.0173 (9)0.0212 (10)0.0022 (7)0.0064 (8)0.0039 (7)
C30.0299 (11)0.0263 (10)0.0198 (10)0.0025 (8)0.0059 (8)0.0012 (8)
C40.0284 (11)0.0265 (11)0.0254 (10)0.0018 (9)0.0112 (8)0.0057 (9)
C50.0213 (10)0.0201 (10)0.0287 (11)0.0003 (7)0.0071 (8)0.0027 (8)
C5A0.0205 (10)0.0152 (9)0.0238 (10)0.0016 (7)0.0054 (8)0.0021 (7)
C60.0167 (9)0.0157 (9)0.0257 (10)0.0022 (7)0.0054 (7)0.0014 (7)
C70.0204 (10)0.0164 (9)0.0217 (9)0.0005 (8)0.0038 (7)0.0012 (8)
C7A0.0150 (9)0.0184 (9)0.0232 (10)0.0021 (7)0.0041 (7)0.0001 (7)
C80.0168 (9)0.0222 (10)0.0223 (10)0.0042 (8)0.0022 (7)0.0004 (8)
N90.0196 (8)0.0256 (9)0.0246 (8)0.0016 (7)0.0060 (7)0.0031 (7)
C100.0172 (9)0.0239 (9)0.0254 (10)0.0004 (8)0.0064 (7)0.0029 (8)
N110.0172 (8)0.0214 (8)0.0245 (9)0.0003 (7)0.0051 (6)0.0025 (7)
C11A0.0136 (9)0.0187 (9)0.0229 (10)0.0040 (7)0.0037 (7)0.0014 (8)
N120.0163 (8)0.0203 (8)0.0197 (8)0.0018 (6)0.0040 (6)0.0004 (6)
C610.0179 (10)0.0229 (10)0.0283 (10)0.0016 (8)0.0025 (8)0.0035 (8)
N810.0289 (9)0.0302 (9)0.0217 (9)0.0057 (8)0.0029 (7)0.0003 (7)
C870.0286 (11)0.0381 (12)0.0202 (10)0.0003 (9)0.0046 (8)0.0026 (9)
C810.0285 (11)0.0292 (11)0.0189 (9)0.0006 (8)0.0060 (8)0.0029 (8)
C820.0391 (13)0.0423 (14)0.0244 (11)0.0102 (10)0.0080 (9)0.0002 (9)
C830.0420 (14)0.070 (2)0.0351 (14)0.0254 (13)0.0154 (11)0.0133 (12)
C840.0269 (12)0.084 (2)0.0314 (13)0.0058 (13)0.0033 (10)0.0199 (14)
C850.0337 (12)0.0554 (16)0.0241 (11)0.0128 (11)0.0003 (9)0.0094 (10)
C860.0336 (12)0.0313 (11)0.0204 (10)0.0036 (9)0.0047 (8)0.0038 (8)
Geometric parameters (Å, º) top
C1—N121.485 (2)C8—N91.351 (3)
C1—C21.528 (3)C8—N811.361 (3)
C1—H1A0.9900N9—C101.330 (3)
C1—H1B0.9900C10—N111.325 (3)
C2—C2A1.507 (3)C10—H100.9500
C2—H2A0.9900N11—C11A1.359 (3)
C2—H2B0.9900C11A—N121.385 (2)
C2A—C31.383 (3)C61—H61A0.9800
C2A—C2B1.408 (3)C61—H61B0.9800
C2B—C5A1.399 (3)C61—H61C0.9800
C2B—N121.421 (2)N81—C871.458 (3)
C3—C41.396 (3)N81—H810.83 (3)
C3—H30.9500C87—C811.510 (3)
C4—C51.382 (3)C87—H87A0.9900
C4—H40.9500C87—H87B0.9900
C5—C5A1.404 (3)C81—C861.387 (3)
C5—H50.9500C81—C821.394 (3)
C5A—C61.509 (3)C82—C831.385 (4)
C6—C611.529 (3)C82—H820.9500
C6—C71.539 (3)C83—C841.384 (4)
C6—H61.0000C83—H830.9500
C7—C7A1.500 (3)C84—C851.375 (4)
C7—H7A0.9900C84—H840.9500
C7—H7B0.9900C85—C861.390 (3)
C7A—C11A1.391 (3)C85—H850.9500
C7A—C81.412 (3)C86—H860.9500
N12—C1—C2104.94 (16)N9—C8—C7A122.48 (18)
N12—C1—H1A110.8N81—C8—C7A120.54 (18)
C2—C1—H1A110.8C10—N9—C8115.35 (16)
N12—C1—H1B110.8N11—C10—N9128.58 (19)
C2—C1—H1B110.8N11—C10—H10115.7
H1A—C1—H1B108.8N9—C10—H10115.7
C2A—C2—C1103.34 (16)C10—N11—C11A115.09 (17)
C2A—C2—H2A111.1N11—C11A—N12114.18 (16)
C1—C2—H2A111.1N11—C11A—C7A122.95 (17)
C2A—C2—H2B111.1N12—C11A—C7A122.85 (17)
C1—C2—H2B111.1C11A—N12—C2B129.03 (16)
H2A—C2—H2B109.1C11A—N12—C1117.95 (15)
C3—C2A—C2B121.14 (19)C2B—N12—C1109.38 (15)
C3—C2A—C2128.76 (19)C6—C61—H61A109.5
C2B—C2A—C2110.10 (17)C6—C61—H61B109.5
C5A—C2B—C2A120.71 (18)H61A—C61—H61B109.5
C5A—C2B—N12130.32 (18)C6—C61—H61C109.5
C2A—C2B—N12108.97 (17)H61A—C61—H61C109.5
C2A—C3—C4118.99 (19)H61B—C61—H61C109.5
C2A—C3—H3120.5C8—N81—C87124.44 (19)
C4—C3—H3120.5C8—N81—H81117.4 (18)
C5—C4—C3119.39 (18)C87—N81—H81114.6 (18)
C5—C4—H4120.3N81—C87—C81110.95 (17)
C3—C4—H4120.3N81—C87—H87A109.4
C4—C5—C5A123.21 (19)C81—C87—H87A109.4
C4—C5—H5118.4N81—C87—H87B109.4
C5A—C5—H5118.4C81—C87—H87B109.4
C2B—C5A—C5116.52 (18)H87A—C87—H87B108.0
C2B—C5A—C6125.46 (17)C86—C81—C82118.4 (2)
C5—C5A—C6117.98 (17)C86—C81—C87120.73 (19)
C5A—C6—C61113.99 (16)C82—C81—C87120.82 (19)
C5A—C6—C7111.17 (15)C83—C82—C81120.4 (2)
C61—C6—C7111.86 (16)C83—C82—H82119.8
C5A—C6—H6106.4C81—C82—H82119.8
C61—C6—H6106.4C84—C83—C82120.4 (2)
C7—C6—H6106.4C84—C83—H83119.8
C7A—C7—C6114.07 (16)C82—C83—H83119.8
C7A—C7—H7A108.7C85—C84—C83119.8 (2)
C6—C7—H7A108.7C85—C84—H84120.1
C7A—C7—H7B108.7C83—C84—H84120.1
C6—C7—H7B108.7C84—C85—C86119.8 (2)
H7A—C7—H7B107.6C84—C85—H85120.1
C11A—C7A—C8115.41 (17)C86—C85—H85120.1
C11A—C7A—C7121.16 (17)C81—C86—C85121.1 (2)
C8—C7A—C7123.28 (17)C81—C86—H86119.5
N9—C8—N81116.91 (18)C85—C86—H86119.5
N12—C1—C2—C2A17.6 (2)C8—N9—C10—N112.8 (3)
C1—C2—C2A—C3167.5 (2)N9—C10—N11—C11A0.2 (3)
C1—C2—C2A—C2B13.6 (2)C10—N11—C11A—N12178.51 (16)
C3—C2A—C2B—C5A2.3 (3)C10—N11—C11A—C7A3.3 (3)
C2—C2A—C2B—C5A176.74 (17)C8—C7A—C11A—N113.7 (3)
C3—C2A—C2B—N12177.29 (18)C7—C7A—C11A—N11171.97 (17)
C2—C2A—C2B—N123.7 (2)C8—C7A—C11A—N12178.21 (17)
C2B—C2A—C3—C40.9 (3)C7—C7A—C11A—N126.1 (3)
C2—C2A—C3—C4177.9 (2)N11—C11A—N12—C2B148.68 (18)
C2A—C3—C4—C50.9 (3)C7A—C11A—N12—C2B33.1 (3)
C3—C4—C5—C5A1.4 (3)N11—C11A—N12—C17.3 (2)
C2A—C2B—C5A—C51.7 (3)C7A—C11A—N12—C1170.90 (16)
N12—C2B—C5A—C5177.75 (18)C5A—C2B—N12—C11A13.6 (3)
C2A—C2B—C5A—C6175.82 (17)C2A—C2B—N12—C11A165.95 (18)
N12—C2B—C5A—C64.7 (3)C5A—C2B—N12—C1171.18 (19)
C4—C5—C5A—C2B0.1 (3)C2A—C2B—N12—C18.3 (2)
C4—C5—C5A—C6177.83 (18)C2—C1—N12—C11A176.99 (16)
C2B—C5A—C6—C6199.4 (2)C2—C1—N12—C2B16.5 (2)
C5—C5A—C6—C6183.1 (2)N9—C8—N81—C8717.2 (3)
C2B—C5A—C6—C728.2 (3)C7A—C8—N81—C87165.79 (18)
C5—C5A—C6—C7149.33 (17)C8—N81—C87—C81114.1 (2)
C5A—C6—C7—C7A75.8 (2)N81—C87—C81—C86129.7 (2)
C61—C6—C7—C7A52.9 (2)N81—C87—C81—C8248.5 (3)
C6—C7—C7A—C11A69.5 (2)C86—C81—C82—C831.1 (3)
C6—C7—C7A—C8115.19 (19)C87—C81—C82—C83177.1 (2)
C11A—C7A—C8—N90.9 (3)C81—C82—C83—C841.4 (4)
C7—C7A—C8—N9174.70 (17)C82—C83—C84—C850.6 (4)
C11A—C7A—C8—N81177.71 (17)C83—C84—C85—C860.3 (4)
C7—C7A—C8—N812.1 (3)C82—C81—C86—C850.2 (3)
N81—C8—N9—C10174.85 (17)C87—C81—C86—C85178.1 (2)
C7A—C8—N9—C102.1 (3)C84—C85—C86—C810.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7B···N11i0.992.593.478 (2)150
C1—H1B···Cg3ii0.992.943.758 (2)140
C5—H5···Cg3iii0.952.903.712 (2)144
C7—H7A···Cg4iii0.992.733.6068 (19)147
Symmetry codes: (i) x+2, y+1/2, z+1; (ii) x+2, y1/2, z+1; (iii) x+1, y+1/2, z+1.
(VI) N-Benzyl-7-methyl-2,3,7,8-tetrahydro-1H-pyrimido[5',4':6,7]azepino[3,2,1-ij]quinolin-9-amine top
Crystal data top
C23H24N4Dx = 1.284 Mg m3
Mr = 356.46Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PccnCell parameters from 4188 reflections
a = 15.083 (3) Åθ = 2.6–27.5°
b = 27.563 (4) ŵ = 0.08 mm1
c = 8.8681 (13) ÅT = 120 K
V = 3686.8 (11) Å3Block, colourless
Z = 80.12 × 0.12 × 0.10 mm
F(000) = 1520
Data collection top
Bruker D8 Venture
diffractometer
4188 independent reflections
Radiation source: high brilliance microfocus sealed tube3293 reflections with I > 2σ(I)
Multilayer monochromatorRint = 0.056
φ and ω scansθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1917
Tmin = 0.874, Tmax = 0.992k = 3335
31735 measured reflectionsl = 1110
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.0438P)2 + 1.5761P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
4188 reflectionsΔρmax = 0.22 e Å3
248 parametersΔρmin = 0.25 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.47010 (9)0.60015 (5)0.26984 (16)0.0154 (3)
H1A0.43130.62070.33330.018*
H1B0.43360.57360.22740.018*
C20.50895 (9)0.63038 (5)0.14229 (16)0.0192 (3)
H2A0.46080.64250.07640.023*
H2B0.54940.61020.08060.023*
C30.55978 (9)0.67308 (5)0.20986 (17)0.0196 (3)
H3A0.60350.68480.13500.024*
H3B0.51770.69990.23010.024*
C3A0.60788 (9)0.66061 (5)0.35447 (16)0.0166 (3)
C3B0.59796 (8)0.61583 (4)0.42804 (16)0.0132 (3)
C40.66180 (9)0.69556 (5)0.42200 (19)0.0221 (3)
H40.66900.72620.37470.026*
C50.70484 (10)0.68633 (5)0.55619 (19)0.0258 (4)
H50.74290.71020.59860.031*
C60.69272 (9)0.64231 (5)0.62949 (18)0.0225 (3)
H60.72210.63630.72240.027*
C6A0.63786 (8)0.60700 (5)0.56786 (16)0.0149 (3)
C70.61821 (9)0.55973 (5)0.64707 (15)0.0149 (3)
H70.55290.55390.64070.018*
C80.66481 (9)0.51785 (4)0.56658 (15)0.0144 (3)
H8A0.72930.52460.56640.017*
H8B0.65540.48800.62660.017*
C8A0.63663 (8)0.50767 (4)0.40670 (15)0.0122 (3)
C90.66845 (8)0.46463 (4)0.33830 (15)0.0130 (3)
N100.64346 (7)0.44984 (4)0.19932 (13)0.0150 (2)
C110.58159 (9)0.47731 (4)0.13419 (16)0.0150 (3)
H110.55970.46600.04000.018*
N120.54690 (7)0.51830 (4)0.18438 (13)0.0149 (3)
C12A0.57729 (8)0.53462 (4)0.31946 (15)0.0123 (3)
N130.54186 (7)0.57961 (4)0.36274 (13)0.0131 (2)
C710.64401 (10)0.55957 (5)0.81365 (16)0.0225 (3)
H71A0.70850.56270.82290.034*
H71B0.62480.52910.86010.034*
H71C0.61530.58690.86490.034*
N910.72699 (8)0.43561 (4)0.41223 (15)0.0163 (3)
H910.7449 (11)0.4442 (5)0.500 (2)0.020*
C970.75188 (9)0.38722 (4)0.36001 (17)0.0168 (3)
H97A0.81060.37890.40270.020*
H97B0.75790.38790.24890.020*
C910.68631 (9)0.34779 (4)0.40250 (16)0.0160 (3)
C920.70590 (10)0.31655 (5)0.52123 (17)0.0199 (3)
H920.76060.31990.57330.024*
C930.64675 (10)0.28055 (5)0.56481 (19)0.0250 (3)
H930.66070.25970.64680.030*
C940.56714 (10)0.27515 (5)0.48809 (19)0.0250 (4)
H940.52660.25040.51680.030*
C950.54712 (10)0.30593 (5)0.36942 (19)0.0246 (3)
H950.49260.30230.31700.030*
C960.60593 (9)0.34196 (5)0.32660 (17)0.0200 (3)
H960.59150.36290.24500.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0115 (6)0.0191 (6)0.0156 (7)0.0028 (5)0.0019 (5)0.0010 (5)
C20.0187 (7)0.0229 (7)0.0159 (8)0.0039 (5)0.0010 (6)0.0037 (6)
C30.0193 (7)0.0182 (6)0.0213 (8)0.0018 (5)0.0034 (6)0.0056 (6)
C3A0.0128 (6)0.0168 (6)0.0201 (8)0.0031 (5)0.0046 (6)0.0009 (5)
C3B0.0105 (6)0.0135 (6)0.0155 (7)0.0018 (5)0.0019 (5)0.0029 (5)
C40.0180 (7)0.0129 (6)0.0352 (9)0.0003 (5)0.0023 (6)0.0006 (6)
C50.0206 (7)0.0169 (7)0.0400 (10)0.0023 (6)0.0087 (7)0.0070 (6)
C60.0205 (7)0.0207 (7)0.0263 (9)0.0029 (5)0.0090 (6)0.0053 (6)
C6A0.0132 (6)0.0152 (6)0.0163 (8)0.0032 (5)0.0006 (5)0.0043 (5)
C70.0143 (6)0.0190 (6)0.0114 (7)0.0001 (5)0.0008 (5)0.0016 (5)
C80.0156 (6)0.0145 (6)0.0131 (7)0.0008 (5)0.0018 (5)0.0019 (5)
C8A0.0119 (6)0.0127 (6)0.0120 (7)0.0027 (5)0.0010 (5)0.0006 (5)
C90.0120 (6)0.0144 (6)0.0126 (7)0.0037 (5)0.0013 (5)0.0015 (5)
N100.0172 (6)0.0156 (5)0.0123 (6)0.0010 (4)0.0000 (5)0.0010 (4)
C110.0184 (7)0.0162 (6)0.0104 (7)0.0032 (5)0.0017 (5)0.0008 (5)
N120.0163 (6)0.0155 (5)0.0128 (6)0.0008 (4)0.0028 (5)0.0004 (4)
C12A0.0117 (6)0.0137 (6)0.0114 (7)0.0037 (5)0.0015 (5)0.0003 (5)
N130.0121 (5)0.0137 (5)0.0134 (6)0.0006 (4)0.0017 (4)0.0001 (4)
C710.0247 (8)0.0302 (8)0.0126 (8)0.0027 (6)0.0005 (6)0.0033 (6)
N910.0193 (6)0.0136 (5)0.0159 (7)0.0017 (4)0.0056 (5)0.0024 (5)
C970.0146 (6)0.0151 (6)0.0208 (8)0.0024 (5)0.0004 (6)0.0014 (5)
C910.0167 (7)0.0134 (6)0.0180 (8)0.0030 (5)0.0044 (6)0.0057 (5)
C920.0204 (7)0.0168 (6)0.0225 (8)0.0040 (5)0.0006 (6)0.0032 (6)
C930.0314 (8)0.0161 (7)0.0276 (9)0.0037 (6)0.0081 (7)0.0018 (6)
C940.0253 (8)0.0155 (6)0.0342 (10)0.0037 (6)0.0119 (7)0.0052 (6)
C950.0188 (7)0.0235 (7)0.0314 (9)0.0025 (6)0.0017 (6)0.0089 (6)
C960.0195 (7)0.0196 (6)0.0210 (8)0.0009 (5)0.0004 (6)0.0023 (6)
Geometric parameters (Å, º) top
C1—N131.4734 (16)C8A—C91.4162 (18)
C1—C21.5221 (19)C9—N101.3518 (18)
C1—H1A0.9900C9—N911.3598 (17)
C1—H1B0.9900N10—C111.3331 (17)
C2—C31.527 (2)C11—N121.3223 (17)
C2—H2A0.9900C11—H110.9500
C2—H2B0.9900N12—C12A1.3593 (17)
C3—C3A1.513 (2)C12A—N131.4036 (16)
C3—H3A0.9900C71—H71A0.9800
C3—H3B0.9900C71—H71B0.9800
C3A—C41.3958 (19)C71—H71C0.9800
C3A—C3B1.4042 (18)N91—C971.4607 (16)
C3B—C6A1.400 (2)N91—H910.855 (17)
C3B—N131.4311 (16)C97—C911.5171 (18)
C4—C51.379 (2)C97—H97A0.9900
C4—H40.9500C97—H97B0.9900
C5—C61.389 (2)C91—C921.392 (2)
C5—H50.9500C91—C961.396 (2)
C6—C6A1.3894 (19)C92—C931.389 (2)
C6—H60.9500C92—H920.9500
C6A—C71.5096 (18)C93—C941.388 (2)
C7—C711.5277 (19)C93—H930.9500
C7—C81.5284 (18)C94—C951.385 (2)
C7—H71.0000C94—H940.9500
C8—C8A1.5066 (19)C95—C961.385 (2)
C8—H8A0.9900C95—H950.9500
C8—H8B0.9900C96—H960.9500
C8A—C12A1.3969 (18)
N13—C1—C2110.07 (11)C12A—C8A—C8127.08 (12)
N13—C1—H1A109.6C9—C8A—C8117.61 (11)
C2—C1—H1A109.6N10—C9—N91116.32 (12)
N13—C1—H1B109.6N10—C9—C8A123.27 (12)
C2—C1—H1B109.6N91—C9—C8A120.42 (12)
H1A—C1—H1B108.2C11—N10—C9114.77 (11)
C1—C2—C3108.87 (12)N12—C11—N10128.05 (13)
C1—C2—H2A109.9N12—C11—H11116.0
C3—C2—H2A109.9N10—C11—H11116.0
C1—C2—H2B109.9C11—N12—C12A116.49 (11)
C3—C2—H2B109.9N12—C12A—C8A121.87 (11)
H2A—C2—H2B108.3N12—C12A—N13113.89 (11)
C3A—C3—C2113.47 (11)C8A—C12A—N13124.21 (12)
C3A—C3—H3A108.9C12A—N13—C3B120.12 (10)
C2—C3—H3A108.9C12A—N13—C1117.79 (11)
C3A—C3—H3B108.9C3B—N13—C1113.11 (10)
C2—C3—H3B108.9C7—C71—H71A109.5
H3A—C3—H3B107.7C7—C71—H71B109.5
C4—C3A—C3B118.00 (13)H71A—C71—H71B109.5
C4—C3A—C3119.10 (12)C7—C71—H71C109.5
C3B—C3A—C3122.85 (12)H71A—C71—H71C109.5
C6A—C3B—C3A121.25 (12)H71B—C71—H71C109.5
C6A—C3B—N13119.43 (11)C9—N91—C97123.44 (12)
C3A—C3B—N13119.22 (12)C9—N91—H91118.7 (10)
C5—C4—C3A121.14 (13)C97—N91—H91117.3 (10)
C5—C4—H4119.4N91—C97—C91114.07 (11)
C3A—C4—H4119.4N91—C97—H97A108.7
C4—C5—C6120.20 (13)C91—C97—H97A108.7
C4—C5—H5119.9N91—C97—H97B108.7
C6—C5—H5119.9C91—C97—H97B108.7
C5—C6—C6A120.42 (14)H97A—C97—H97B107.6
C5—C6—H6119.8C92—C91—C96118.56 (13)
C6A—C6—H6119.8C92—C91—C97119.52 (13)
C6—C6A—C3B118.86 (13)C96—C91—C97121.93 (13)
C6—C6A—C7122.57 (13)C93—C92—C91121.06 (14)
C3B—C6A—C7118.55 (11)C93—C92—H92119.5
C6A—C7—C71113.73 (11)C91—C92—H92119.5
C6A—C7—C8110.14 (11)C94—C93—C92119.73 (14)
C71—C7—C8109.41 (11)C94—C93—H93120.1
C6A—C7—H7107.8C92—C93—H93120.1
C71—C7—H7107.8C95—C94—C93119.68 (13)
C8—C7—H7107.8C95—C94—H94120.2
C8A—C8—C7116.77 (11)C93—C94—H94120.2
C8A—C8—H8A108.1C96—C95—C94120.54 (14)
C7—C8—H8A108.1C96—C95—H95119.7
C8A—C8—H8B108.1C94—C95—H95119.7
C7—C8—H8B108.1C95—C96—C91120.44 (14)
H8A—C8—H8B107.3C95—C96—H96119.8
C12A—C8A—C9115.18 (12)C91—C96—H96119.8
N13—C1—C2—C363.04 (14)C9—N10—C11—N124.9 (2)
C1—C2—C3—C3A36.42 (15)N10—C11—N12—C12A0.4 (2)
C2—C3—C3A—C4175.61 (13)C11—N12—C12A—C8A5.04 (18)
C2—C3—C3A—C3B7.09 (19)C11—N12—C12A—N13176.53 (11)
C4—C3A—C3B—C6A2.6 (2)C9—C8A—C12A—N125.37 (18)
C3—C3A—C3B—C6A174.77 (12)C8—C8A—C12A—N12170.31 (12)
C4—C3A—C3B—N13178.94 (12)C9—C8A—C12A—N13176.37 (11)
C3—C3A—C3B—N131.62 (19)C8—C8A—C12A—N138.0 (2)
C3B—C3A—C4—C50.6 (2)N12—C12A—N13—C3B137.57 (12)
C3—C3A—C4—C5178.05 (13)C8A—C12A—N13—C3B44.05 (18)
C3A—C4—C5—C62.2 (2)N12—C12A—N13—C17.39 (16)
C4—C5—C6—C6A0.6 (2)C8A—C12A—N13—C1170.99 (12)
C5—C6—C6A—C3B2.5 (2)C6A—C3B—N13—C12A64.73 (17)
C5—C6—C6A—C7176.39 (13)C3A—C3B—N13—C12A118.82 (13)
C3A—C3B—C6A—C64.1 (2)C6A—C3B—N13—C1148.80 (12)
N13—C3B—C6A—C6179.51 (12)C3A—C3B—N13—C127.65 (16)
C3A—C3B—C6A—C7174.84 (12)C2—C1—N13—C12A88.19 (14)
N13—C3B—C6A—C71.54 (18)C2—C1—N13—C3B59.12 (14)
C6—C6A—C7—C7114.54 (19)N10—C9—N91—C979.89 (19)
C3B—C6A—C7—C71164.37 (12)C8A—C9—N91—C97169.98 (12)
C6—C6A—C7—C8108.68 (15)C9—N91—C97—C9181.94 (17)
C3B—C6A—C7—C872.41 (15)N91—C97—C91—C92102.99 (14)
C6A—C7—C8—C8A63.28 (15)N91—C97—C91—C9676.50 (17)
C71—C7—C8—C8A171.01 (11)C96—C91—C92—C930.6 (2)
C7—C8—C8A—C12A5.31 (19)C97—C91—C92—C93178.92 (12)
C7—C8—C8A—C9170.28 (11)C91—C92—C93—C940.7 (2)
C12A—C8A—C9—N100.53 (18)C92—C93—C94—C950.5 (2)
C8—C8A—C9—N10175.57 (12)C93—C94—C95—C960.1 (2)
C12A—C8A—C9—N91179.60 (11)C94—C95—C96—C910.0 (2)
C8—C8A—C9—N914.29 (18)C92—C91—C96—C950.2 (2)
N91—C9—N10—C11175.67 (11)C97—C91—C96—C95179.25 (13)
C8A—C9—N10—C114.20 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N91—H91···N10i0.857 (17)2.446 (17)3.2332 (18)152.9 (14)
C11—H11···N12ii0.952.593.4281 (19)147
C1—H1A···Cg5iii0.992.853.8018 (17)162
C7—H7···Cg6iii1.002.883.7965 (16)153
Symmetry codes: (i) x+3/2, y, z+1/2; (ii) x+1, y+1, z; (iii) x+1, y+1, z+1.
Parameters (Å, °) for hydrogen bonds and short intermolecular contacts top
CompoundD—H···AD—HH···AD···AD—H···A
(I)N3—H3···O4i0.87 (3)1.88 (3)2.745 (3)175 (3)
C2—H2···N1ii0.952.523.304 (3)140
(II)O81—H81···N3iii1.01 (3)1.82 (3)2.825 (2)171 (2)
C2—H2···N1iv0.952.593.330 (4)135
C10—H10···Cg1v0.952.853.743 (2)156
(III)O81—H81···N3vi0.87 (2)1.91 (2)2.767 (2)165 (2)
(IV)C2—H2···.O81vi0.952.573.386 (2)144
C45—H45···Cg1vii0.952.993.7583 (19)139
C46—H46···Cg2viii0.952.993.7583 (19)139
(V)C7—H7B···N11ix0.992.593.478 (2)150
C1—H1B···Cg3x0.992.943.758 (2)140
C5—H5···Cg3xi0.952.903.712 (2)144
C7—H7A···Cg4xi0.992.733.6068 (19)147
(VI)N91—H91···N10xii0.857 (17)2.446 (17)3.2332 (18)152.9 (14)
C11—H11···N12xiii0.952.593.4281 (19)147
C1—H1A···Cg5xiv0.992.853.8018 (17)162
C7—H7···Cg6xiv1.002.883.7965 (16)153
Cg1–Cg6 represent the centroids of the C6A/C7–C10/C10A, N1/C2/N3/C4–C6, N9/C8/C7A/C11A/N11/C10, C2A/C2B/C5A/C5/C4/C3, C91–C96 and N10/C9/C8A/C12A/N12/C11 rings, respectively. The perpendicular distances of the H atoms from the ring planes in the C—H···π interactions are (Å): 2.82 for (II), H45 2.94 and H46 2.95 for (IV); H1B 2.76, H5 2.68 and H7A 2.69 for (V); H1A 2.82, H7 2.83 for (VI).

Symmetry codes: (i) -x, -y, -z+1; (ii) -x, y-1/2, -z+1/2; (iii) x, -y+3/2, z+1/2; (iv) -x, -y+2, -z+1; (v) -x, y+1/2, -z+3/2; (vi) x, -y+3/2, z-1/2; (vii) -x+1, -y+2, -z+1; (viii) -x+1, y+1/2, -z+1/2; (ix) -x+2, y+1/2, -z+1; (x) -x+2, y-1/2, -z+1; (xi) -x+1, y+1/2, -z+1; (xii) -x+3/2, y, z+1/2; (xiii) -x+1, -y+1, -z; (xiv) -x+1, -y+1, -z+1.
Selected geometric parameters (Å, °) top
Compound(I)(II)(III)(IV)(V)(VI)
Ring-puckering parameters
(a)Five-membered ring
Q20.176 (2)
φ247.2 (7)
(b)Six-membered ring
Q0.5135 (14)
θ129.17 (16)
φ250.8 (2)
(c)Seven-membered rings
Q0.830 (2)0.880 (2)0.8709 (18)0.8444 (16)0.6813 (18)0.8585 (14)
φ234.00 (19)29.60 (16)51.24 (13)45.62 (11)302.24 (18)35.11 (10)
φ3290.3 (6)295.1 (5)283.4 (3)291.1 (3)85.0 (3)292.7 (3)
Dihedral angles
54.37 (12)57.43 (11)47.49 (8)51.02 (7)28.05 (8)52.90 (6)
Notes: (i) ring-puckering angles are calculated for the following atom sequences: five-membered ring N12–C1–C2–C2A–C2B; six-membered ring N13–C1–C2–C3–C3A–C3B; seven-membered rings N11–C10A–C6A–C6–C5–C4A–C11A for (I)–(IV), N12–C2B–C5A–C6–C7–C7A–C11A for (V) and N13–C3B–C6A–C7–C8–C8A–C12A for (VI); (ii) dihedral denotes the dihedral angle between the mean planes of the fused phenyl and pyrimidine rings.
Selected torsion angles in (IV)–(VI) (Å, °) top
(IV)C4A—C4—N41—C47178.04 (15)
C4—N41—C47—C41-141.85 (16)
N41—C47—C41—C42-98.48 (19)
(V)C7A—C8—N81—C87-165.79 (18)
C8—N81—C87—C81114.1 (2)
N81—C87—C81—C82-48.5 (3)
(VI)C8A—C9—N91—C97169.98 (12)
C9—N91—C97—C91-81.94 (17)
N91—C97—C91—C92-102.99 (14)
Note: (i) The IUPAC names for compounds (IV)–(VI) lead to different atom labels for comparable sequences of atoms, but the equivalence of the torsion angles reported for (IV)–(VI) is shown by Figs. 4–6.
 

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