A concise, efficient and versatile synthesis of amino-substituted benzo[b]pyrimido[5,4-f]azepines: synthesis and spectroscopic characterization, together with the mol­ecular and supra­molecular structures of three products and one inter­mediate

A concise, efficient and versatile synthesis of amino-substituted benzo[b]pyrimido[5,4-f]azepines is described: starting from a 5-allyl-4,6-di­chloro­pyrimidine, the synthesis involves base-catalysed amino­lysis followed by intra­molecular Friedel–Crafts cyclization. Four new amino-substituted benzo[b]pyrimido[5,4-f]azepines are reported, and all the products and reaction inter­mediates have been fully characterized by IR, ¹H and ¹³C NMR spectroscopy and mass spectrometry, and the mol­ecular and supra­molecular structures of three products and one inter­mediate have been determined. In each of N,2,6,11-tetra­methyl-N-phenyl-6,11-di­hydro-5H-benzo[b]pyrimido[5,4-f]azepin-4-amine, C₂₂H₂₄N₅, (III), 4-(1H-benzo[d]imidazol-1-yl)-6,11-dimethyl-6,11-di­hydro-5H-benzo[b]pyrimido[5,4-f]azepine, which crystallizes as a 0.374-hydrate, C₂₁H₁₉N₅·0.374H₂O, (VIIIa), and 6,7,9,11-tetra­methyl-4-(5-methyl-1H-benzo[d]imidazol-1-yl)-6,11-di­hydro-5H-benzo[b]pyrimido[5,4-f]azepine, C₂₄H₂₅N₅, (VIIIc), the azepine ring adopts a boat conformation, but with a different configuration at the stereogenic centre in (VIIIc), as compared with (III) and (VIIIa). In the inter­mediate 5-allyl-6-(1H-benzo[d]imidazol-1-yl)-N-methyl-N-(4-methyl­phen­yl)pyrimidin-4-amine, C₂₂N₂₁N₅, (VIIb), the immediate precursor of 4-(1H-benzo[d]imidazol-1-yl)-6,8,11-trimethyl-6,11-di­hydro-5H-benzo[b]pyrimido[5,4-f]azepine, (VIIIb), the allyl group is disordered over two sets of atomic sites having occupancies of 0.688 (5) and 0.312 (5). The mol­ecules of (III) are linked into chains by a C—H...π(pyrimidine) hydrogen bond, and those of (VIIb) are linked into complex sheets by three hydrogen bonds, one of the C—H...N type and two of C—H...π(arene) type. The mol­ecules of the organic component in (VIIIa) are linked into a chain of rings by two C—H...π(arene) hydrogen bonds, and these chains are linked into sheets by the water components; a single weak C—H...N hydrogen bond links mol­ecules of (VIIIc) into centrosymmetric R₂²(10) dimers. Comparisons are made with some related compounds.

Computing details

Data collection: COLLECT (Bruker, 2008) for (III); APEX2 (Bruker 2014) for (VIIb), (VIIIa); APEX3 (Bruker, 2016) for (VIIIc). Cell refinement: DIRAX/LSQ (Duisenberg, 1992) for (III); APEX2 (Bruker 2014) for (VIIb), (VIIIa); SAINT (Bruker, 2016) for (VIIIc). Data reduction: EVALCCD (Duisenberg et al., 2003) for (III); SAINT (Bruker, 2013) for (VIIb), (VIIIa); SAINT (Bruker, 2016) for (VIIIc). For all structures, program(s) used to solve structure: SIR92 (Altomare et al., 1994); 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).

N,2,6,11-Tetramethyl-N-phenyl-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepin-4-amine (III)

Crystal data

C22H24N4	Dx = 1.239 Mg m^−3
Mr = 344.45	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 4234 reflections
a = 11.2020 (19) Å	θ = 2.7–27.5°
b = 16.609 (3) Å	µ = 0.08 mm^−1
c = 19.850 (6) Å	T = 120 K
V = 3693.2 (14) Å^3	Block, colourless
Z = 8	0.32 × 0.16 × 0.16 mm
F(000) = 1472

Data collection

Bruker–Nonius KappaCCD diffractometer	3635 independent reflections
Radiation source: sealed tube	2278 reflections with I > 2σ(I)
Horizonally mounted graphite crystal monochromator	Rint = 0.121
Detector resolution: 9 pixels mm^-1	θmax = 26.1°, θmin = 3.6°
φ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS2008; Bruker, 2008)	k = −20→20
Tmin = 0.881, Tmax = 0.988	l = −24→24
34307 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.056	w = 1/[σ^2(Fo^2) + (0.0151P)^2 + 4.0628P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.109	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.24 e Å^−3
3635 reflections	Δρmin = −0.24 e Å^−3
240 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0053 (3)

Special details

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.

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

	x	y	z	Uiso*/Ueq
N1	0.28278 (17)	0.28956 (12)	0.36310 (10)	0.0197 (5)
C2	0.3141 (2)	0.35742 (14)	0.39407 (12)	0.0200 (5)
N3	0.41965 (18)	0.37266 (11)	0.42248 (10)	0.0207 (5)
C4	0.5006 (2)	0.31252 (14)	0.41939 (11)	0.0175 (5)
C4A	0.4779 (2)	0.23681 (14)	0.39019 (12)	0.0176 (5)
C5	0.5661 (2)	0.16913 (14)	0.40057 (12)	0.0204 (5)
H5A	0.6051	0.1768	0.4449	0.025*
H5B	0.6289	0.1735	0.3657	0.025*
C6	0.5142 (2)	0.08315 (14)	0.39807 (12)	0.0216 (6)
H6	0.4385	0.0826	0.4248	0.026*
C6A	0.4842 (2)	0.06217 (14)	0.32603 (12)	0.0195 (5)
C7	0.5444 (2)	0.00169 (14)	0.29046 (13)	0.0245 (6)
H7	0.6070	−0.0270	0.3120	0.029*
C8	0.5145 (2)	−0.01719 (16)	0.22470 (13)	0.0289 (6)
H8	0.5550	−0.0594	0.2019	0.035*
C9	0.4259 (2)	0.02527 (16)	0.19239 (14)	0.0294 (6)
H9	0.4060	0.0129	0.1470	0.035*
C10	0.3658 (2)	0.08607 (15)	0.22599 (12)	0.0254 (6)
H10	0.3054	0.1158	0.2034	0.030*
C10A	0.3934 (2)	0.10388 (13)	0.29288 (12)	0.0201 (5)
N11	0.32113 (17)	0.16129 (12)	0.32803 (10)	0.0211 (5)
C11A	0.3645 (2)	0.22941 (13)	0.36037 (12)	0.0180 (5)
C21	0.2240 (2)	0.42414 (16)	0.39324 (14)	0.0303 (6)
H21A	0.1465	0.4034	0.4081	0.046*
H21B	0.2168	0.4455	0.3474	0.046*
H21C	0.2500	0.4672	0.4237	0.046*
N41	0.60941 (18)	0.32791 (12)	0.45169 (10)	0.0208 (5)
C41	0.7186 (2)	0.31411 (14)	0.41603 (12)	0.0195 (5)
C42	0.7251 (2)	0.32332 (14)	0.34628 (12)	0.0196 (5)
H42	0.6560	0.3381	0.3214	0.024*
C43	0.8328 (2)	0.31091 (14)	0.31324 (13)	0.0237 (6)
H43	0.8365	0.3164	0.2656	0.028*
C44	0.9345 (2)	0.29072 (15)	0.34879 (14)	0.0277 (6)
H44	1.0082	0.2833	0.3259	0.033*
C45	0.9283 (2)	0.28141 (15)	0.41784 (14)	0.0276 (6)
H45	0.9981	0.2679	0.4426	0.033*
C46	0.8210 (2)	0.29173 (15)	0.45120 (13)	0.0249 (6)
H46	0.8170	0.2835	0.4985	0.030*
C47	0.6128 (2)	0.39612 (15)	0.49882 (13)	0.0269 (6)
H47A	0.5426	0.3942	0.5282	0.040*
H47B	0.6127	0.4467	0.4734	0.040*
H47C	0.6854	0.3929	0.5262	0.040*
C61	0.6014 (2)	0.02508 (16)	0.43093 (14)	0.0323 (7)
H61A	0.6793	0.0293	0.4087	0.048*
H61B	0.5713	−0.0301	0.4265	0.048*
H61C	0.6100	0.0386	0.4787	0.048*
C111	0.1928 (2)	0.15959 (16)	0.31141 (14)	0.0276 (6)
H11A	0.1771	0.1964	0.2739	0.041*
H11B	0.1464	0.1764	0.3508	0.041*
H11C	0.1697	0.1048	0.2985	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0207 (11)	0.0192 (11)	0.0193 (11)	0.0020 (9)	0.0026 (8)	−0.0010 (9)
C2	0.0210 (13)	0.0231 (14)	0.0158 (12)	0.0023 (10)	0.0038 (10)	0.0008 (10)
N3	0.0250 (12)	0.0178 (10)	0.0193 (11)	0.0021 (9)	0.0044 (9)	0.0006 (9)
C4	0.0181 (12)	0.0213 (13)	0.0130 (12)	−0.0007 (10)	0.0015 (10)	0.0023 (10)
C4A	0.0201 (12)	0.0180 (12)	0.0146 (12)	0.0004 (10)	0.0045 (10)	0.0008 (10)
C5	0.0204 (12)	0.0190 (13)	0.0219 (13)	0.0013 (10)	−0.0024 (10)	−0.0008 (10)
C6	0.0232 (13)	0.0186 (13)	0.0230 (14)	0.0005 (11)	−0.0017 (11)	−0.0001 (10)
C6A	0.0208 (13)	0.0138 (12)	0.0239 (13)	−0.0042 (10)	0.0051 (10)	0.0007 (10)
C7	0.0212 (13)	0.0195 (13)	0.0328 (15)	−0.0034 (11)	0.0043 (11)	−0.0010 (11)
C8	0.0278 (15)	0.0242 (14)	0.0347 (16)	−0.0027 (12)	0.0071 (12)	−0.0118 (12)
C9	0.0330 (15)	0.0296 (15)	0.0256 (14)	−0.0065 (12)	−0.0015 (12)	−0.0077 (12)
C10	0.0260 (14)	0.0228 (14)	0.0273 (14)	−0.0029 (11)	−0.0033 (11)	−0.0031 (11)
C10A	0.0206 (13)	0.0149 (12)	0.0249 (14)	−0.0045 (10)	0.0029 (11)	−0.0025 (10)
N11	0.0158 (10)	0.0196 (11)	0.0279 (12)	0.0002 (9)	−0.0021 (9)	−0.0053 (9)
C11A	0.0214 (13)	0.0170 (12)	0.0155 (12)	−0.0003 (10)	0.0029 (10)	0.0012 (10)
C21	0.0262 (15)	0.0293 (15)	0.0356 (16)	0.0060 (12)	0.0014 (12)	−0.0063 (13)
N41	0.0215 (11)	0.0217 (11)	0.0191 (11)	−0.0016 (9)	0.0001 (9)	−0.0038 (9)
C41	0.0222 (13)	0.0139 (12)	0.0224 (13)	−0.0019 (10)	−0.0024 (10)	−0.0005 (10)
C42	0.0225 (13)	0.0151 (12)	0.0213 (13)	−0.0009 (10)	−0.0032 (10)	0.0019 (10)
C43	0.0279 (14)	0.0207 (13)	0.0225 (14)	−0.0018 (11)	0.0041 (11)	−0.0018 (11)
C44	0.0226 (14)	0.0234 (14)	0.0369 (16)	0.0017 (11)	0.0050 (12)	−0.0014 (12)
C45	0.0211 (14)	0.0246 (14)	0.0372 (16)	0.0008 (11)	−0.0061 (12)	0.0033 (12)
C46	0.0271 (14)	0.0267 (14)	0.0210 (13)	−0.0005 (11)	−0.0041 (11)	0.0045 (11)
C47	0.0315 (15)	0.0257 (14)	0.0234 (14)	−0.0021 (12)	−0.0035 (12)	−0.0085 (11)
C61	0.0364 (16)	0.0257 (14)	0.0348 (16)	0.0036 (13)	−0.0057 (13)	0.0034 (12)
C111	0.0182 (13)	0.0283 (15)	0.0365 (16)	−0.0006 (11)	−0.0054 (12)	−0.0055 (12)

Geometric parameters (Å, º)

N1—C2	1.331 (3)	N11—C111	1.475 (3)
N1—C11A	1.356 (3)	C21—H21A	0.9800
C2—N3	1.334 (3)	C21—H21B	0.9800
C2—C21	1.499 (3)	C21—H21C	0.9800
N3—C4	1.351 (3)	N41—C41	1.432 (3)
C4—N41	1.400 (3)	N41—C47	1.470 (3)
C4—C4A	1.408 (3)	C41—C46	1.393 (3)
C4A—C11A	1.407 (3)	C41—C42	1.395 (3)
C4A—C5	1.511 (3)	C42—C43	1.388 (3)
C5—C6	1.543 (3)	C42—H42	0.9500
C5—H5A	0.9900	C43—C44	1.382 (4)
C5—H5B	0.9900	C43—H43	0.9500
C6—C6A	1.510 (3)	C44—C45	1.381 (4)
C6—C61	1.520 (3)	C44—H44	0.9500
C6—H6	1.0000	C45—C46	1.383 (4)
C6A—C10A	1.396 (3)	C45—H45	0.9500
C6A—C7	1.400 (3)	C46—H46	0.9500
C7—C8	1.384 (4)	C47—H47A	0.9800
C7—H7	0.9500	C47—H47B	0.9800
C8—C9	1.376 (4)	C47—H47C	0.9800
C8—H8	0.9500	C61—H61A	0.9800
C9—C10	1.385 (4)	C61—H61B	0.9800
C9—H9	0.9500	C61—H61C	0.9800
C10—C10A	1.395 (3)	C111—H11A	0.9800
C10—H10	0.9500	C111—H11B	0.9800
C10A—N11	1.432 (3)	C111—H11C	0.9800
N11—C11A	1.388 (3)
C2—N1—C11A	117.7 (2)	N11—C11A—C4A	125.5 (2)
N1—C2—N3	126.1 (2)	C2—C21—H21A	109.5
N1—C2—C21	116.3 (2)	C2—C21—H21B	109.5
N3—C2—C21	117.4 (2)	H21A—C21—H21B	109.5
C2—N3—C4	115.8 (2)	C2—C21—H21C	109.5
N3—C4—N41	115.4 (2)	H21A—C21—H21C	109.5
N3—C4—C4A	123.9 (2)	H21B—C21—H21C	109.5
N41—C4—C4A	120.6 (2)	C4—N41—C41	119.20 (18)
C11A—C4A—C4	114.5 (2)	C4—N41—C47	117.0 (2)
C11A—C4A—C5	125.7 (2)	C41—N41—C47	114.6 (2)
C4—C4A—C5	119.3 (2)	C46—C41—C42	118.9 (2)
C4A—C5—C6	115.9 (2)	C46—C41—N41	119.9 (2)
C4A—C5—H5A	108.3	C42—C41—N41	121.2 (2)
C6—C5—H5A	108.3	C43—C42—C41	119.9 (2)
C4A—C5—H5B	108.3	C43—C42—H42	120.1
C6—C5—H5B	108.3	C41—C42—H42	120.1
H5A—C5—H5B	107.4	C44—C43—C42	120.7 (2)
C6A—C6—C61	113.8 (2)	C44—C43—H43	119.6
C6A—C6—C5	109.14 (19)	C42—C43—H43	119.6
C61—C6—C5	109.3 (2)	C45—C44—C43	119.5 (2)
C6A—C6—H6	108.2	C45—C44—H44	120.3
C61—C6—H6	108.2	C43—C44—H44	120.3
C5—C6—H6	108.2	C44—C45—C46	120.3 (2)
C10A—C6A—C7	118.0 (2)	C44—C45—H45	119.8
C10A—C6A—C6	119.6 (2)	C46—C45—H45	119.8
C7—C6A—C6	122.4 (2)	C45—C46—C41	120.6 (2)
C8—C7—C6A	121.5 (2)	C45—C46—H46	119.7
C8—C7—H7	119.3	C41—C46—H46	119.7
C6A—C7—H7	119.3	N41—C47—H47A	109.5
C9—C8—C7	119.9 (2)	N41—C47—H47B	109.5
C9—C8—H8	120.1	H47A—C47—H47B	109.5
C7—C8—H8	120.1	N41—C47—H47C	109.5
C8—C9—C10	120.0 (2)	H47A—C47—H47C	109.5
C8—C9—H9	120.0	H47B—C47—H47C	109.5
C10—C9—H9	120.0	C6—C61—H61A	109.5
C9—C10—C10A	120.3 (2)	C6—C61—H61B	109.5
C9—C10—H10	119.8	H61A—C61—H61B	109.5
C10A—C10—H10	119.8	C6—C61—H61C	109.5
C10—C10A—C6A	120.3 (2)	H61A—C61—H61C	109.5
C10—C10A—N11	118.7 (2)	H61B—C61—H61C	109.5
C6A—C10A—N11	120.9 (2)	N11—C111—H11A	109.5
C11A—N11—C10A	124.76 (19)	N11—C111—H11B	109.5
C11A—N11—C111	117.37 (19)	H11A—C111—H11B	109.5
C10A—N11—C111	115.40 (19)	N11—C111—H11C	109.5
N1—C11A—N11	112.5 (2)	H11A—C111—H11C	109.5
N1—C11A—C4A	121.9 (2)	H11B—C111—H11C	109.5
C11A—N1—C2—N3	0.7 (4)	C6A—C10A—N11—C11A	59.2 (3)
C11A—N1—C2—C21	177.1 (2)	C10—C10A—N11—C111	36.3 (3)
N1—C2—N3—C4	−0.5 (4)	C6A—C10A—N11—C111	−139.1 (2)
C21—C2—N3—C4	−176.9 (2)	C2—N1—C11A—N11	178.9 (2)
C2—N3—C4—N41	−177.6 (2)	C2—N1—C11A—C4A	1.3 (3)
C2—N3—C4—C4A	−1.7 (3)	C10A—N11—C11A—N1	152.5 (2)
N3—C4—C4A—C11A	3.4 (3)	C111—N11—C11A—N1	−8.8 (3)
N41—C4—C4A—C11A	179.1 (2)	C10A—N11—C11A—C4A	−30.0 (4)
N3—C4—C4A—C5	−168.9 (2)	C111—N11—C11A—C4A	168.7 (2)
N41—C4—C4A—C5	6.7 (3)	C4—C4A—C11A—N1	−3.2 (3)
C11A—C4A—C5—C6	−19.2 (3)	C5—C4A—C11A—N1	168.6 (2)
C4—C4A—C5—C6	152.3 (2)	C4—C4A—C11A—N11	179.5 (2)
C4A—C5—C6—C6A	73.1 (3)	C5—C4A—C11A—N11	−8.7 (4)
C4A—C5—C6—C61	−161.9 (2)	N3—C4—N41—C41	−129.9 (2)
C61—C6—C6A—C10A	171.4 (2)	C4A—C4—N41—C41	54.1 (3)
C5—C6—C6A—C10A	−66.2 (3)	N3—C4—N41—C47	15.3 (3)
C61—C6—C6A—C7	−8.5 (3)	C4A—C4—N41—C47	−160.8 (2)
C5—C6—C6A—C7	113.9 (2)	C4—N41—C41—C46	−149.8 (2)
C10A—C6A—C7—C8	−0.7 (3)	C47—N41—C41—C46	64.3 (3)
C6—C6A—C7—C8	179.2 (2)	C4—N41—C41—C42	30.8 (3)
C6A—C7—C8—C9	1.6 (4)	C47—N41—C41—C42	−115.1 (2)
C7—C8—C9—C10	−0.8 (4)	C46—C41—C42—C43	−0.6 (4)
C8—C9—C10—C10A	−0.9 (4)	N41—C41—C42—C43	178.9 (2)
C9—C10—C10A—C6A	1.9 (4)	C41—C42—C43—C44	−1.1 (4)
C9—C10—C10A—N11	−173.6 (2)	C42—C43—C44—C45	1.2 (4)
C7—C6A—C10A—C10	−1.1 (3)	C43—C44—C45—C46	0.4 (4)
C6—C6A—C10A—C10	179.0 (2)	C44—C45—C46—C41	−2.0 (4)
C7—C6A—C10A—N11	174.3 (2)	C42—C41—C46—C45	2.1 (4)
C6—C6A—C10A—N11	−5.6 (3)	N41—C41—C46—C45	−177.3 (2)
C10—C10A—N11—C11A	−125.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C46—H46···Cg1^i	0.95	2.72	3.564 (3)	148

Symmetry code: (i) x+1/2, −y+1/2, −z+1.

5-Allyl-6-(1H-benzo[d]imidazol-1-yl)-N-methyl-N-(4-methylphenyl)pyrimidin-4-amine (VIIb)

Crystal data

C22H21N5	F(000) = 752
Mr = 355.44	Dx = 1.318 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.425 (2) Å	Cell parameters from 4120 reflections
b = 11.184 (3) Å	θ = 2.2–27.8°
c = 17.321 (6) Å	µ = 0.08 mm^−1
β = 101.091 (11)°	T = 100 K
V = 1791.7 (9) Å^3	Block, colourless
Z = 4	0.12 × 0.12 × 0.10 mm

Data collection

Bruker D8 Venture diffractometer	4120 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube	3558 reflections with I > 2σ(I)
Multilayer mirror monochromator	Rint = 0.032
φ and ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS2016; Bruker, 2016)	h = −11→12
Tmin = 0.827, Tmax = 0.901	k = −14→14
20400 measured reflections	l = −21→22

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.111	w = 1/[σ^2(Fo^2) + (0.0513P)^2 + 0.9508P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
4120 reflections	Δρmax = 0.28 e Å^−3
265 parameters	Δρmin = −0.35 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.85273 (12)	0.11048 (10)	0.43802 (6)	0.0196 (2)
C2	0.92438 (15)	0.14439 (12)	0.38272 (8)	0.0220 (3)
H2	0.9807	0.0846	0.3638	0.026*
N3	0.92637 (13)	0.25200 (10)	0.35092 (7)	0.0211 (2)
C4	0.83142 (14)	0.32934 (11)	0.37194 (7)	0.0169 (3)
C5	0.73975 (13)	0.30547 (11)	0.42370 (7)	0.0166 (3)
C6	0.76533 (13)	0.19224 (11)	0.46169 (7)	0.0162 (3)
N41	0.82808 (12)	0.44064 (10)	0.33194 (6)	0.0172 (2)
C42	0.83232 (14)	0.45092 (12)	0.25318 (8)	0.0206 (3)
H42	0.8268	0.3840	0.2190	0.025*
N43	0.84449 (12)	0.56035 (10)	0.22975 (7)	0.0213 (2)
C43A	0.85275 (13)	0.62931 (12)	0.29758 (7)	0.0176 (3)
C44	0.86851 (14)	0.75300 (12)	0.30728 (8)	0.0214 (3)
H44	0.8751	0.8037	0.2641	0.026*
C45	0.87416 (14)	0.79896 (12)	0.38195 (9)	0.0243 (3)
H45	0.8834	0.8829	0.3900	0.029*
C46	0.86661 (14)	0.72432 (12)	0.44604 (8)	0.0227 (3)
H46	0.8718	0.7590	0.4966	0.027*
C47	0.85180 (13)	0.60132 (12)	0.43789 (8)	0.0190 (3)
H47	0.8478	0.5507	0.4815	0.023*
C47A	0.84314 (12)	0.55619 (11)	0.36224 (7)	0.0156 (2)
C51A	0.60826 (15)	0.38072 (13)	0.42720 (9)	0.0269 (3)	0.688 (5)
H51A	0.6130	0.4576	0.3995	0.032*	0.688 (5)
H51B	0.6015	0.3975	0.4825	0.032*	0.688 (5)
C52A	0.4738 (3)	0.3047 (2)	0.38521 (14)	0.0176 (5)	0.688 (5)
H52A	0.4791	0.2653	0.3373	0.021*	0.688 (5)
C53A	0.3549 (2)	0.2937 (2)	0.41387 (13)	0.0280 (7)	0.688 (5)
H53A	0.3473	0.3323	0.4618	0.034*	0.688 (5)
H53B	0.2767	0.2471	0.3867	0.034*	0.688 (5)
C51B	0.60826 (15)	0.38072 (13)	0.42720 (9)	0.0269 (3)	0.312 (5)
H51C	0.6351	0.4292	0.4756	0.032*	0.312 (5)
H51D	0.6010	0.4376	0.3828	0.032*	0.312 (5)
C52B	0.4659 (5)	0.3430 (4)	0.4263 (3)	0.0217 (13)	0.312 (5)
H52B	0.4050	0.3840	0.4553	0.026*	0.312 (5)
C53B	0.4213 (6)	0.2498 (6)	0.3844 (3)	0.0267 (14)	0.312 (5)
H53C	0.4841	0.2102	0.3559	0.032*	0.312 (5)
H53D	0.3257	0.2211	0.3821	0.032*	0.312 (5)
N61	0.69502 (12)	0.15641 (9)	0.52017 (6)	0.0176 (2)
C61	0.66733 (13)	0.23718 (11)	0.57940 (7)	0.0160 (2)
C62	0.54003 (14)	0.22746 (12)	0.60864 (8)	0.0192 (3)
H62	0.4703	0.1687	0.5879	0.023*
C63	0.51479 (14)	0.30306 (12)	0.66788 (8)	0.0196 (3)
H63	0.4280	0.2946	0.6876	0.024*
C64	0.61386 (14)	0.39146 (11)	0.69922 (7)	0.0189 (3)
C65	0.74114 (14)	0.40003 (12)	0.66962 (8)	0.0200 (3)
H65	0.8105	0.4593	0.6900	0.024*
C66	0.76852 (13)	0.32378 (11)	0.61094 (8)	0.0180 (3)
H66	0.8565	0.3306	0.5922	0.022*
C67	0.69961 (16)	0.02896 (11)	0.54070 (8)	0.0244 (3)
H67A	0.6812	−0.0190	0.4925	0.037*
H67B	0.6255	0.0117	0.5718	0.037*
H67C	0.7952	0.0091	0.5715	0.037*
C68	0.58358 (15)	0.47459 (13)	0.76267 (8)	0.0251 (3)
H68A	0.6400	0.4494	0.8136	0.038*
H68B	0.4803	0.4720	0.7644	0.038*
H68C	0.6107	0.5563	0.7512	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0217 (6)	0.0165 (5)	0.0193 (5)	0.0010 (4)	0.0007 (4)	−0.0032 (4)
C2	0.0251 (7)	0.0195 (6)	0.0210 (6)	0.0017 (5)	0.0035 (5)	−0.0058 (5)
N3	0.0246 (6)	0.0199 (5)	0.0191 (5)	0.0000 (4)	0.0052 (4)	−0.0051 (4)
C4	0.0181 (6)	0.0170 (6)	0.0141 (6)	−0.0022 (5)	−0.0005 (5)	−0.0025 (5)
C5	0.0143 (6)	0.0170 (6)	0.0169 (6)	−0.0003 (4)	−0.0011 (5)	0.0003 (5)
C6	0.0137 (6)	0.0173 (6)	0.0153 (6)	−0.0018 (4)	−0.0028 (4)	−0.0009 (5)
N41	0.0197 (5)	0.0179 (5)	0.0140 (5)	−0.0027 (4)	0.0033 (4)	−0.0014 (4)
C42	0.0232 (6)	0.0243 (6)	0.0147 (6)	−0.0033 (5)	0.0049 (5)	−0.0024 (5)
N43	0.0219 (6)	0.0249 (6)	0.0179 (5)	−0.0026 (5)	0.0053 (4)	0.0008 (4)
C43A	0.0114 (5)	0.0222 (6)	0.0190 (6)	−0.0011 (5)	0.0025 (5)	0.0008 (5)
C44	0.0152 (6)	0.0206 (6)	0.0281 (7)	−0.0007 (5)	0.0036 (5)	0.0042 (5)
C45	0.0179 (6)	0.0167 (6)	0.0362 (8)	0.0004 (5)	0.0002 (6)	−0.0029 (5)
C46	0.0183 (6)	0.0246 (7)	0.0235 (7)	0.0028 (5)	−0.0005 (5)	−0.0079 (5)
C47	0.0161 (6)	0.0226 (6)	0.0174 (6)	0.0029 (5)	0.0014 (5)	−0.0010 (5)
C47A	0.0106 (5)	0.0173 (6)	0.0183 (6)	0.0000 (4)	0.0015 (4)	−0.0014 (5)
C51A	0.0173 (6)	0.0285 (7)	0.0364 (8)	0.0080 (5)	0.0089 (6)	0.0182 (6)
C52A	0.0168 (10)	0.0191 (11)	0.0167 (11)	0.0017 (9)	0.0027 (8)	−0.0006 (9)
C53A	0.0187 (12)	0.0402 (13)	0.0247 (11)	−0.0026 (9)	0.0030 (9)	0.0044 (9)
C51B	0.0173 (6)	0.0285 (7)	0.0364 (8)	0.0080 (5)	0.0089 (6)	0.0182 (6)
C52B	0.020 (2)	0.022 (2)	0.023 (3)	0.0079 (17)	0.0048 (18)	0.004 (2)
C53B	0.020 (3)	0.028 (3)	0.030 (3)	−0.003 (2)	0.000 (2)	0.005 (2)
N61	0.0186 (5)	0.0140 (5)	0.0195 (5)	0.0010 (4)	0.0023 (4)	0.0031 (4)
C61	0.0156 (6)	0.0152 (5)	0.0162 (6)	0.0027 (4)	0.0003 (4)	0.0049 (4)
C62	0.0150 (6)	0.0204 (6)	0.0206 (6)	−0.0025 (5)	−0.0004 (5)	0.0043 (5)
C63	0.0136 (6)	0.0246 (6)	0.0205 (6)	0.0011 (5)	0.0030 (5)	0.0060 (5)
C64	0.0174 (6)	0.0205 (6)	0.0174 (6)	0.0041 (5)	0.0003 (5)	0.0032 (5)
C65	0.0155 (6)	0.0197 (6)	0.0233 (7)	−0.0013 (5)	0.0002 (5)	0.0003 (5)
C66	0.0124 (6)	0.0197 (6)	0.0216 (6)	0.0007 (5)	0.0027 (5)	0.0032 (5)
C67	0.0332 (8)	0.0153 (6)	0.0245 (7)	0.0020 (5)	0.0047 (6)	0.0047 (5)
C68	0.0237 (7)	0.0289 (7)	0.0224 (7)	0.0028 (6)	0.0035 (5)	−0.0017 (6)

Geometric parameters (Å, º)

N1—C2	1.3289 (18)	C52A—C53A	1.316 (4)
N1—C6	1.3464 (17)	C52A—H52A	0.9500
C2—N3	1.3253 (18)	C53A—H53A	0.9500
C2—H2	0.9500	C53A—H53B	0.9500
N3—C4	1.3442 (17)	C52B—C53B	1.293 (9)
C4—C5	1.3854 (18)	C52B—H52B	0.9500
C4—N41	1.4220 (16)	C53B—H53C	0.9500
C5—C6	1.4260 (17)	C53B—H53D	0.9500
C5—C51A	1.5089 (18)	N61—C61	1.4281 (17)
C6—N61	1.3727 (17)	N61—C67	1.4677 (16)
N41—C42	1.3774 (17)	C61—C62	1.3934 (18)
N41—C47A	1.3917 (16)	C61—C66	1.3948 (18)
C42—N43	1.3014 (18)	C62—C63	1.3851 (19)
C42—H42	0.9500	C62—H62	0.9500
N43—C43A	1.3950 (17)	C63—C64	1.3960 (19)
C43A—C44	1.3980 (18)	C63—H63	0.9500
C43A—C47A	1.4038 (18)	C64—C65	1.3957 (18)
C44—C45	1.383 (2)	C64—C68	1.5080 (19)
C44—H44	0.9500	C65—C66	1.3884 (19)
C45—C46	1.402 (2)	C65—H65	0.9500
C45—H45	0.9500	C66—H66	0.9500
C46—C47	1.3872 (19)	C67—H67A	0.9800
C46—H46	0.9500	C67—H67B	0.9800
C47—C47A	1.3918 (18)	C67—H67C	0.9800
C47—H47	0.9500	C68—H68A	0.9800
C51A—C52A	1.582 (3)	C68—H68B	0.9800
C51A—H51A	0.9900	C68—H68C	0.9800
C51A—H51B	0.9900
C2—N1—C6	116.81 (11)	H51A—C51A—H51B	108.7
N3—C2—N1	127.49 (12)	C53A—C52A—C51A	122.8 (2)
N3—C2—H2	116.3	C53A—C52A—H52A	118.6
N1—C2—H2	116.3	C51A—C52A—H52A	118.6
C2—N3—C4	114.10 (12)	C52A—C53A—H53A	120.0
N3—C4—C5	125.58 (12)	C52A—C53A—H53B	120.0
N3—C4—N41	112.63 (11)	H53A—C53A—H53B	120.0
C5—C4—N41	121.72 (11)	C53B—C52B—H52B	121.5
C4—C5—C6	113.49 (11)	C52B—C53B—H53C	120.0
C4—C5—C51A	122.54 (11)	C52B—C53B—H53D	120.0
C6—C5—C51A	122.95 (11)	H53C—C53B—H53D	120.0
N1—C6—N61	115.91 (11)	C6—N61—C61	121.76 (10)
N1—C6—C5	121.44 (12)	C6—N61—C67	117.80 (11)
N61—C6—C5	122.48 (11)	C61—N61—C67	116.19 (10)
C42—N41—C47A	106.00 (11)	C62—C61—C66	118.91 (12)
C42—N41—C4	123.61 (11)	C62—C61—N61	120.06 (11)
C47A—N41—C4	129.64 (11)	C66—C61—N61	121.00 (11)
N43—C42—N41	114.11 (12)	C63—C62—C61	120.29 (12)
N43—C42—H42	122.9	C63—C62—H62	119.9
N41—C42—H42	122.9	C61—C62—H62	119.9
C42—N43—C43A	104.55 (11)	C62—C63—C64	121.53 (12)
N43—C43A—C44	129.48 (12)	C62—C63—H63	119.2
N43—C43A—C47A	110.38 (11)	C64—C63—H63	119.2
C44—C43A—C47A	120.14 (12)	C65—C64—C63	117.63 (12)
C45—C44—C43A	117.66 (12)	C65—C64—C68	121.46 (12)
C45—C44—H44	121.2	C63—C64—C68	120.92 (12)
C43A—C44—H44	121.2	C66—C65—C64	121.37 (12)
C44—C45—C46	121.37 (12)	C66—C65—H65	119.3
C44—C45—H45	119.3	C64—C65—H65	119.3
C46—C45—H45	119.3	C65—C66—C61	120.26 (12)
C47—C46—C45	121.97 (13)	C65—C66—H66	119.9
C47—C46—H46	119.0	C61—C66—H66	119.9
C45—C46—H46	119.0	N61—C67—H67A	109.5
C46—C47—C47A	116.23 (12)	N61—C67—H67B	109.5
C46—C47—H47	121.9	H67A—C67—H67B	109.5
C47A—C47—H47	121.9	N61—C67—H67C	109.5
N41—C47A—C47	132.46 (12)	H67A—C67—H67C	109.5
N41—C47A—C43A	104.93 (11)	H67B—C67—H67C	109.5
C47—C47A—C43A	122.60 (12)	C64—C68—H68A	109.5
C5—C51A—C52A	105.86 (13)	C64—C68—H68B	109.5
C5—C51A—H51A	110.6	H68A—C68—H68B	109.5
C52A—C51A—H51A	110.6	C64—C68—H68C	109.5
C5—C51A—H51B	110.6	H68A—C68—H68C	109.5
C52A—C51A—H51B	110.6	H68B—C68—H68C	109.5
C6—N1—C2—N3	4.1 (2)	C42—N41—C47A—C43A	1.12 (13)
N1—C2—N3—C4	−8.1 (2)	C4—N41—C47A—C43A	171.35 (12)
C2—N3—C4—C5	1.83 (19)	C46—C47—C47A—N41	−179.93 (13)
C2—N3—C4—N41	−175.23 (11)	C46—C47—C47A—C43A	1.75 (18)
N3—C4—C5—C6	6.89 (18)	N43—C43A—C47A—N41	−0.27 (13)
N41—C4—C5—C6	−176.31 (11)	C44—C43A—C47A—N41	179.83 (11)
N3—C4—C5—C51A	−161.86 (13)	N43—C43A—C47A—C47	178.45 (11)
N41—C4—C5—C51A	14.94 (19)	C44—C43A—C47A—C47	−1.45 (18)
C2—N1—C6—N61	−178.48 (11)	C4—C5—C51A—C52A	104.52 (16)
C2—N1—C6—C5	6.16 (18)	C6—C5—C51A—C52A	−63.17 (17)
C4—C5—C6—N1	−10.93 (17)	C5—C51A—C52A—C53A	135.9 (2)
C51A—C5—C6—N1	157.76 (13)	N1—C6—N61—C61	144.86 (11)
C4—C5—C6—N61	174.01 (11)	C5—C6—N61—C61	−39.82 (17)
C51A—C5—C6—N61	−17.30 (19)	N1—C6—N61—C67	−11.06 (17)
N3—C4—N41—C42	41.55 (17)	C5—C6—N61—C67	164.25 (12)
C5—C4—N41—C42	−135.64 (13)	C6—N61—C61—C62	144.49 (12)
N3—C4—N41—C47A	−127.15 (13)	C67—N61—C61—C62	−59.22 (16)
C5—C4—N41—C47A	55.66 (18)	C6—N61—C61—C66	−37.87 (17)
C47A—N41—C42—N43	−1.74 (15)	C67—N61—C61—C66	118.42 (13)
C4—N41—C42—N43	−172.71 (11)	C66—C61—C62—C63	0.21 (18)
N41—C42—N43—C43A	1.53 (15)	N61—C61—C62—C63	177.90 (11)
C42—N43—C43A—C44	179.15 (13)	C61—C62—C63—C64	0.83 (19)
C42—N43—C43A—C47A	−0.74 (14)	C62—C63—C64—C65	−1.02 (19)
N43—C43A—C44—C45	−179.83 (12)	C62—C63—C64—C68	178.86 (12)
C47A—C43A—C44—C45	0.04 (18)	C63—C64—C65—C66	0.18 (19)
C43A—C44—C45—C46	0.95 (19)	C68—C64—C65—C66	−179.69 (12)
C44—C45—C46—C47	−0.6 (2)	C64—C65—C66—C61	0.84 (19)
C45—C46—C47—C47A	−0.73 (19)	C62—C61—C66—C65	−1.03 (18)
C42—N41—C47A—C47	−177.42 (13)	N61—C61—C66—C65	−178.69 (11)
C4—N41—C47A—C47	−7.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N43^i	0.95	2.54	3.325 (2)	140
C63—H63···Cg2^ii	0.95	2.73	3.4689 (19)	136
C66—H66···Cg2^iii	0.95	2.63	3.4616 (18)	146

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

4-(1H-Benzo[d]imidazol-1-yl)-6,11-dimethyl-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepine 0.374-hydrate (VIIIa)

Crystal data

C21H19N5·0.374H2O	F(000) = 735
Mr = 348.15	Dx = 1.373 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.1086 (5) Å	Cell parameters from 3871 reflections
b = 8.7806 (3) Å	θ = 2.4–27.5°
c = 17.7753 (9) Å	µ = 0.09 mm^−1
β = 103.651 (2)°	T = 100 K
V = 1684.83 (13) Å^3	Block, colourless
Z = 4	0.13 × 0.10 × 0.08 mm

Data collection

Bruker D8 Venture diffractometer	3868 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube	2711 reflections with I > 2σ(I)
Multilayer mirror monochromator	Rint = 0.051
φ and ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS2015; Bruker, 2015)	h = −14→14
Tmin = 0.832, Tmax = 0.993	k = −11→9
12545 measured reflections	l = −22→23

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.048P)^2 + 0.4718P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3868 reflections	Δρmax = 0.21 e Å^−3
247 parameters	Δρmin = −0.26 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.32067 (13)	0.58303 (16)	0.39329 (9)	0.0253 (3)
C2	0.19917 (16)	0.5575 (2)	0.37653 (11)	0.0273 (4)
H2	0.1574	0.5815	0.4159	0.033*
N3	0.12951 (13)	0.50222 (16)	0.31087 (9)	0.0252 (3)
C4	0.19232 (15)	0.47720 (17)	0.25649 (10)	0.0205 (4)
C4A	0.31713 (15)	0.50520 (17)	0.26273 (10)	0.0197 (4)
C5	0.36758 (15)	0.49987 (19)	0.19083 (10)	0.0236 (4)
H5B	0.3007	0.5293	0.1457	0.028*
H5A	0.3915	0.3937	0.1826	0.028*
C6	0.47989 (15)	0.60372 (19)	0.19372 (10)	0.0226 (4)
H6	0.4644	0.7025	0.2178	0.027*
C6A	0.59149 (15)	0.52944 (18)	0.24631 (11)	0.0237 (4)
C7	0.68634 (16)	0.46295 (19)	0.21789 (13)	0.0308 (5)
H7	0.6816	0.4651	0.1638	0.037*
C8	0.78738 (17)	0.3939 (2)	0.26720 (14)	0.0384 (5)
H8	0.8511	0.3499	0.2469	0.046*
C9	0.79488 (16)	0.3893 (2)	0.34587 (14)	0.0371 (5)
H9	0.8646	0.3438	0.3798	0.045*
C10	0.70083 (16)	0.45107 (19)	0.37542 (12)	0.0298 (5)
H10	0.7057	0.4464	0.4294	0.036*
C10A	0.59866 (15)	0.52031 (18)	0.32585 (11)	0.0239 (4)
N11	0.50659 (13)	0.58955 (15)	0.35900 (8)	0.0235 (3)
C11A	0.38147 (15)	0.55698 (17)	0.33734 (10)	0.0209 (4)
N41	0.11810 (12)	0.41909 (15)	0.18570 (8)	0.0205 (3)
C42	0.13352 (16)	0.28123 (19)	0.15209 (11)	0.0278 (4)
H42	0.2007	0.2145	0.1723	0.033*
N43	0.04769 (13)	0.25079 (16)	0.09017 (9)	0.0276 (4)
C43A	−0.03192 (15)	0.37600 (18)	0.08117 (10)	0.0197 (4)
C44	−0.13957 (16)	0.40407 (19)	0.02440 (10)	0.0244 (4)
H44	−0.1696	0.3326	−0.0158	0.029*
C45	−0.20093 (17)	0.5388 (2)	0.02850 (11)	0.0275 (4)
H45	−0.2747	0.5605	−0.0095	0.033*
C46	−0.15679 (16)	0.6445 (2)	0.08761 (10)	0.0255 (4)
H46	−0.2007	0.7373	0.0880	0.031*
C47	−0.05152 (14)	0.61810 (18)	0.14521 (10)	0.0193 (4)
H47	−0.0224	0.6892	0.1857	0.023*
C47A	0.00946 (14)	0.48146 (17)	0.14062 (9)	0.0163 (3)
C61	0.49531 (16)	0.6370 (2)	0.11247 (11)	0.0280 (4)
H61A	0.5696	0.6992	0.1157	0.042*
H61C	0.4225	0.6921	0.0833	0.042*
H61B	0.5038	0.5409	0.0861	0.042*
C111	0.55216 (17)	0.6643 (2)	0.43446 (10)	0.0308 (5)
H11C	0.4957	0.7470	0.4401	0.046*
H11A	0.6350	0.7060	0.4375	0.046*
H11B	0.5561	0.5898	0.4760	0.046*
O1	−0.0627 (3)	0.0022 (5)	0.0018 (2)	0.0490 (16)	0.374 (4)
H1A	0.0005	0.0616	0.0191	0.074*	0.374 (4)
H1B	−0.0466	−0.0577	−0.0336	0.074*	0.374 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0270 (8)	0.0215 (7)	0.0235 (8)	0.0050 (6)	−0.0018 (7)	−0.0012 (6)
C2	0.0272 (10)	0.0276 (9)	0.0244 (10)	0.0078 (8)	0.0009 (8)	−0.0004 (8)
N3	0.0222 (7)	0.0248 (7)	0.0262 (9)	0.0047 (6)	0.0012 (7)	−0.0020 (6)
C4	0.0188 (8)	0.0145 (7)	0.0238 (9)	0.0025 (6)	−0.0038 (7)	−0.0025 (7)
C4A	0.0184 (8)	0.0132 (7)	0.0240 (9)	0.0026 (7)	−0.0023 (7)	−0.0015 (7)
C5	0.0188 (8)	0.0226 (8)	0.0262 (10)	0.0008 (7)	−0.0010 (7)	−0.0058 (7)
C6	0.0192 (8)	0.0182 (8)	0.0273 (10)	0.0012 (7)	−0.0006 (7)	−0.0011 (7)
C6A	0.0168 (8)	0.0129 (7)	0.0379 (11)	−0.0037 (7)	−0.0004 (8)	0.0037 (7)
C7	0.0220 (9)	0.0222 (9)	0.0482 (13)	−0.0009 (8)	0.0081 (9)	0.0086 (8)
C8	0.0219 (9)	0.0254 (10)	0.0684 (16)	0.0035 (8)	0.0115 (10)	0.0183 (10)
C9	0.0168 (9)	0.0241 (9)	0.0641 (16)	−0.0015 (8)	−0.0030 (9)	0.0229 (10)
C10	0.0213 (9)	0.0181 (8)	0.0432 (12)	−0.0067 (7)	−0.0065 (8)	0.0113 (8)
C10A	0.0166 (8)	0.0131 (7)	0.0364 (11)	−0.0051 (7)	−0.0049 (8)	0.0042 (7)
N11	0.0221 (7)	0.0174 (7)	0.0242 (8)	−0.0021 (6)	−0.0081 (6)	−0.0006 (6)
C11A	0.0215 (8)	0.0108 (7)	0.0247 (10)	0.0023 (6)	−0.0057 (7)	0.0012 (7)
N41	0.0151 (7)	0.0156 (7)	0.0276 (8)	0.0014 (5)	−0.0014 (6)	−0.0053 (6)
C42	0.0245 (9)	0.0163 (8)	0.0392 (12)	0.0023 (7)	0.0006 (8)	−0.0074 (8)
N43	0.0274 (8)	0.0173 (7)	0.0348 (9)	0.0000 (6)	0.0009 (7)	−0.0079 (7)
C43A	0.0203 (8)	0.0153 (7)	0.0233 (9)	−0.0031 (7)	0.0047 (7)	−0.0013 (7)
C44	0.0257 (9)	0.0239 (8)	0.0209 (9)	−0.0080 (7)	0.0001 (8)	−0.0044 (7)
C45	0.0239 (9)	0.0304 (9)	0.0227 (10)	0.0008 (8)	−0.0056 (8)	0.0000 (8)
C46	0.0233 (9)	0.0227 (8)	0.0280 (10)	0.0047 (7)	0.0012 (8)	−0.0012 (7)
C47	0.0174 (8)	0.0188 (8)	0.0212 (9)	−0.0011 (7)	0.0034 (7)	−0.0038 (7)
C47A	0.0135 (7)	0.0175 (8)	0.0173 (9)	−0.0027 (6)	0.0024 (7)	−0.0006 (6)
C61	0.0239 (9)	0.0269 (9)	0.0309 (11)	0.0043 (8)	0.0021 (8)	−0.0005 (8)
C111	0.0337 (10)	0.0289 (9)	0.0225 (10)	−0.0127 (8)	−0.0081 (8)	0.0036 (8)
O1	0.027 (2)	0.065 (3)	0.053 (3)	−0.003 (2)	0.0038 (19)	−0.044 (2)

Geometric parameters (Å, º)

N1—C2	1.331 (2)	N11—C11A	1.382 (2)
N1—C11A	1.347 (2)	N11—C111	1.472 (2)
C2—N3	1.331 (2)	N41—C42	1.378 (2)
C2—H2	0.9500	N41—C47A	1.394 (2)
N3—C4	1.337 (2)	C42—N43	1.303 (2)
C4—C4A	1.387 (2)	C42—H42	0.9500
C4—N41	1.426 (2)	N43—C43A	1.396 (2)
C4A—C11A	1.424 (2)	C43A—C44	1.393 (2)
C4A—C5	1.513 (2)	C43A—C47A	1.399 (2)
C5—C6	1.536 (2)	C44—C45	1.376 (3)
C5—H5B	0.9900	C44—H44	0.9500
C5—H5A	0.9900	C45—C46	1.401 (2)
C6—C6A	1.513 (2)	C45—H45	0.9500
C6—C61	1.522 (3)	C46—C47	1.380 (2)
C6—H6	1.0000	C46—H46	0.9500
C6A—C7	1.399 (3)	C47—C47A	1.390 (2)
C6A—C10A	1.399 (3)	C47—H47	0.9500
C7—C8	1.390 (3)	C61—H61A	0.9800
C7—H7	0.9500	C61—H61C	0.9800
C8—C9	1.382 (3)	C61—H61B	0.9800
C8—H8	0.9500	C111—H11C	0.9800
C9—C10	1.386 (3)	C111—H11A	0.9800
C9—H9	0.9500	C111—H11B	0.9800
C10—C10A	1.401 (2)	O1—H1A	0.8702
C10—H10	0.9500	O1—H1B	0.8701
C10A—N11	1.431 (2)
C2—N1—C11A	117.70 (15)	C10A—N11—C111	116.06 (14)
N3—C2—N1	127.37 (18)	N1—C11A—N11	113.94 (15)
N3—C2—H2	116.3	N1—C11A—C4A	120.85 (15)
N1—C2—H2	116.3	N11—C11A—C4A	125.19 (16)
C2—N3—C4	113.54 (15)	C42—N41—C47A	105.97 (13)
N3—C4—C4A	126.55 (16)	C42—N41—C4	126.27 (14)
N3—C4—N41	113.89 (14)	C47A—N41—C4	127.49 (13)
C4A—C4—N41	119.54 (16)	N43—C42—N41	113.92 (15)
C4—C4A—C11A	113.81 (16)	N43—C42—H42	123.0
C4—C4A—C5	119.33 (15)	N41—C42—H42	123.0
C11A—C4A—C5	126.30 (15)	C42—N43—C43A	104.64 (14)
C4A—C5—C6	114.40 (14)	C44—C43A—N43	129.40 (15)
C4A—C5—H5B	108.7	C44—C43A—C47A	120.21 (15)
C6—C5—H5B	108.7	N43—C43A—C47A	110.39 (14)
C4A—C5—H5A	108.7	C45—C44—C43A	117.73 (16)
C6—C5—H5A	108.7	C45—C44—H44	121.1
H5B—C5—H5A	107.6	C43A—C44—H44	121.1
C6A—C6—C61	114.18 (14)	C44—C45—C46	121.29 (17)
C6A—C6—C5	107.78 (14)	C44—C45—H45	119.4
C61—C6—C5	110.75 (14)	C46—C45—H45	119.4
C6A—C6—H6	108.0	C47—C46—C45	122.01 (16)
C61—C6—H6	108.0	C47—C46—H46	119.0
C5—C6—H6	108.0	C45—C46—H46	119.0
C7—C6A—C10A	118.21 (16)	C46—C47—C47A	116.18 (15)
C7—C6A—C6	122.27 (17)	C46—C47—H47	121.9
C10A—C6A—C6	119.46 (15)	C47A—C47—H47	121.9
C8—C7—C6A	121.3 (2)	C47—C47A—N41	132.34 (15)
C8—C7—H7	119.4	C47—C47A—C43A	122.56 (15)
C6A—C7—H7	119.4	N41—C47A—C43A	105.06 (13)
C9—C8—C7	119.85 (19)	C6—C61—H61A	109.5
C9—C8—H8	120.1	C6—C61—H61C	109.5
C7—C8—H8	120.1	H61A—C61—H61C	109.5
C8—C9—C10	120.11 (18)	C6—C61—H61B	109.5
C8—C9—H9	119.9	H61A—C61—H61B	109.5
C10—C9—H9	119.9	H61C—C61—H61B	109.5
C9—C10—C10A	120.2 (2)	N11—C111—H11C	109.5
C9—C10—H10	119.9	N11—C111—H11A	109.5
C10A—C10—H10	119.9	H11C—C111—H11A	109.5
C6A—C10A—C10	120.33 (17)	N11—C111—H11B	109.5
C6A—C10A—N11	121.05 (15)	H11C—C111—H11B	109.5
C10—C10A—N11	118.50 (17)	H11A—C111—H11B	109.5
C11A—N11—C10A	124.55 (14)	H1A—O1—H1B	109.5
C11A—N11—C111	116.96 (15)
C11A—N1—C2—N3	3.1 (3)	C10A—N11—C11A—N1	154.19 (15)
N1—C2—N3—C4	−2.9 (3)	C111—N11—C11A—N1	−7.3 (2)
C2—N3—C4—C4A	−1.0 (2)	C10A—N11—C11A—C4A	−27.8 (2)
C2—N3—C4—N41	−179.51 (14)	C111—N11—C11A—C4A	170.65 (15)
N3—C4—C4A—C11A	4.0 (2)	C4—C4A—C11A—N1	−3.6 (2)
N41—C4—C4A—C11A	−177.55 (13)	C5—C4A—C11A—N1	167.63 (15)
N3—C4—C4A—C5	−167.93 (16)	C4—C4A—C11A—N11	178.50 (15)
N41—C4—C4A—C5	10.5 (2)	C5—C4A—C11A—N11	−10.2 (3)
C4—C4A—C5—C6	150.99 (15)	N3—C4—N41—C42	−119.01 (18)
C11A—C4A—C5—C6	−19.8 (2)	C4A—C4—N41—C42	62.4 (2)
C4A—C5—C6—C6A	75.17 (18)	N3—C4—N41—C47A	54.2 (2)
C4A—C5—C6—C61	−159.28 (14)	C4A—C4—N41—C47A	−124.41 (17)
C61—C6—C6A—C7	−15.3 (2)	C47A—N41—C42—N43	1.0 (2)
C5—C6—C6A—C7	108.24 (18)	C4—N41—C42—N43	175.39 (16)
C61—C6—C6A—C10A	167.59 (15)	N41—C42—N43—C43A	−0.3 (2)
C5—C6—C6A—C10A	−68.92 (19)	C42—N43—C43A—C44	179.99 (18)
C10A—C6A—C7—C8	−2.1 (2)	C42—N43—C43A—C47A	−0.5 (2)
C6—C6A—C7—C8	−179.29 (16)	N43—C43A—C44—C45	−179.40 (17)
C6A—C7—C8—C9	0.4 (3)	C47A—C43A—C44—C45	1.2 (3)
C7—C8—C9—C10	1.2 (3)	C43A—C44—C45—C46	0.1 (3)
C8—C9—C10—C10A	−0.9 (3)	C44—C45—C46—C47	−1.2 (3)
C7—C6A—C10A—C10	2.3 (2)	C45—C46—C47—C47A	1.0 (3)
C6—C6A—C10A—C10	179.57 (14)	C46—C47—C47A—N41	177.65 (17)
C7—C6A—C10A—N11	178.24 (14)	C46—C47—C47A—C43A	0.3 (2)
C6—C6A—C10A—N11	−4.5 (2)	C42—N41—C47A—C47	−178.84 (18)
C9—C10—C10A—C6A	−0.8 (2)	C4—N41—C47A—C47	6.8 (3)
C9—C10—C10A—N11	−176.87 (15)	C42—N41—C47A—C43A	−1.19 (18)
C6A—C10A—N11—C11A	57.8 (2)	C4—N41—C47A—C43A	−175.52 (16)
C10—C10A—N11—C11A	−126.17 (17)	C44—C43A—C47A—C47	−1.4 (2)
C6A—C10A—N11—C111	−140.51 (16)	N43—C43A—C47A—C47	179.03 (15)
C10—C10A—N11—C111	35.5 (2)	C44—C43A—C47A—N41	−179.37 (15)
C2—N1—C11A—N11	178.62 (14)	N43—C43A—C47A—N41	1.09 (18)
C2—N1—C11A—C4A	0.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N43	0.87	2.08	2.798 (4)	140
O1—H1B···N43^i	0.87	1.97	2.786 (4)	156
C2—H2···O1^ii	0.95	2.11	2.960 (4)	148
C6—H6···Cg3^iii	1.00	2.82	3.6820 (18)	145
C42—H42···Cg3^iv	0.95	2.54	3.4311 (19)	156

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

6,7,9,11-Tetramethyl-4-(5-methyl-1H-benzo[d]imidazol-1-yl)-6,11-dihydro-5H-benzo[b]pyrimido[5,4-f]azepine (VIIIc)

Crystal data

C24H25N5	Z = 2
Mr = 383.49	F(000) = 408
Triclinic, P1	Dx = 1.282 Mg m^−3
a = 9.7866 (13) Å	Cu Kα radiation, λ = 1.54184 Å
b = 10.2122 (15) Å	Cell parameters from 3263 reflections
c = 10.9551 (14) Å	θ = 4.4–63.8°
α = 97.816 (9)°	µ = 0.61 mm^−1
β = 112.433 (8)°	T = 100 K
γ = 94.149 (8)°	Prism, colourless
V = 993.4 (2) Å^3	0.41 × 0.27 × 0.17 mm

Data collection

Bruker D8 Venture diffractometer	3263 independent reflections
Radiation source: INCOATEC high brilliance microfocus sealed tube	2474 reflections with I > 2σ(I)
Multilayer mirror monochromator	Rint = 0.059
φ and ω scans	θmax = 63.8°, θmin = 4.4°
Absorption correction: multi-scan (SADABS2015; Bruker, 2015)	h = −11→11
Tmin = 0.901, Tmax = 0.992	k = −11→11
19629 measured reflections	l = −12→12

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.050	w = 1/[σ^2(Fo^2) + (0.0528P)^2 + 0.9104P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.136	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.28 e Å^−3
3263 reflections	Δρmin = −0.25 e Å^−3
268 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0099 (9)

Special details

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.

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

	x	y	z	Uiso*/Ueq
N1	−0.1130 (2)	0.58699 (19)	0.05702 (19)	0.0252 (5)
C2	−0.1140 (3)	0.6697 (2)	−0.0270 (2)	0.0258 (6)
H2	−0.2039	0.6627	−0.1043	0.031*
N3	−0.0040 (2)	0.76115 (19)	−0.01530 (19)	0.0248 (5)
C4	0.1164 (3)	0.7733 (2)	0.0998 (2)	0.0229 (5)
C4A	0.1337 (2)	0.6998 (2)	0.2011 (2)	0.0232 (5)
C5	0.2666 (3)	0.7385 (2)	0.3333 (2)	0.0257 (6)
H5A	0.3000	0.8352	0.3463	0.031*
H5B	0.3488	0.6906	0.3272	0.031*
C6	0.2421 (3)	0.7108 (2)	0.4583 (2)	0.0253 (6)
H6	0.3333	0.7556	0.5374	0.030*
C6A	0.2371 (3)	0.5633 (2)	0.4616 (2)	0.0226 (5)
C7	0.3450 (3)	0.5142 (2)	0.5655 (2)	0.0240 (5)
C8	0.3398 (3)	0.3778 (2)	0.5630 (2)	0.0256 (6)
H8	0.4110	0.3462	0.6356	0.031*
C9	0.2342 (3)	0.2857 (2)	0.4584 (2)	0.0257 (6)
C10	0.1292 (3)	0.3340 (2)	0.3548 (2)	0.0235 (5)
H10	0.0571	0.2730	0.2811	0.028*
C10A	0.1277 (2)	0.4709 (2)	0.3572 (2)	0.0230 (5)
N11	0.0044 (2)	0.51016 (19)	0.25248 (19)	0.0241 (5)
C11A	0.0121 (3)	0.5987 (2)	0.1708 (2)	0.0233 (5)
N41	0.2302 (2)	0.87818 (19)	0.11704 (19)	0.0233 (5)
C42	0.2160 (3)	1.0118 (2)	0.1298 (2)	0.0257 (6)
H42	0.1248	1.0442	0.1213	0.031*
N43	0.3382 (2)	1.0901 (2)	0.1546 (2)	0.0290 (5)
C43A	0.4430 (3)	1.0034 (2)	0.1578 (2)	0.0248 (5)
C44	0.5925 (3)	1.0313 (2)	0.1783 (2)	0.0275 (6)
H44	0.6382	1.1209	0.1958	0.033*
C45	0.6731 (3)	0.9270 (3)	0.1727 (2)	0.0276 (6)
C46	0.6033 (3)	0.7947 (3)	0.1447 (2)	0.0288 (6)
H46	0.6598	0.7239	0.1395	0.035*
C47	0.4553 (3)	0.7639 (2)	0.1244 (2)	0.0273 (6)
H47	0.4090	0.6742	0.1045	0.033*
C47A	0.3782 (3)	0.8708 (2)	0.1347 (2)	0.0228 (5)
C48	0.8360 (3)	0.9547 (3)	0.1985 (3)	0.0340 (6)
H48A	0.8554	1.0403	0.1730	0.051*
H48B	0.8620	0.8834	0.1452	0.051*
H48C	0.8966	0.9584	0.2940	0.051*
C61	0.1106 (3)	0.7722 (2)	0.4737 (3)	0.0313 (6)
H61A	0.0172	0.7257	0.4027	0.047*
H61B	0.1202	0.8668	0.4669	0.047*
H61C	0.1100	0.7634	0.5615	0.047*
C71	0.4671 (3)	0.6052 (2)	0.6827 (2)	0.0300 (6)
H71A	0.5259	0.5518	0.7466	0.045*
H71B	0.4225	0.6682	0.7272	0.045*
H71C	0.5321	0.6546	0.6502	0.045*
C91	0.2372 (3)	0.1386 (2)	0.4580 (3)	0.0337 (6)
H91A	0.1408	0.0896	0.3947	0.051*
H91B	0.2563	0.1205	0.5483	0.051*
H91C	0.3164	0.1100	0.4308	0.051*
C111	−0.1420 (3)	0.4335 (3)	0.2196 (3)	0.0287 (6)
H11A	−0.2199	0.4914	0.1915	0.043*
H11B	−0.1426	0.3994	0.2989	0.043*
H11C	−0.1612	0.3585	0.1465	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0228 (11)	0.0271 (11)	0.0240 (10)	0.0037 (9)	0.0070 (8)	0.0052 (9)
C2	0.0239 (13)	0.0264 (13)	0.0238 (12)	0.0040 (11)	0.0052 (10)	0.0062 (10)
N3	0.0218 (11)	0.0267 (11)	0.0253 (11)	0.0051 (9)	0.0075 (9)	0.0069 (9)
C4	0.0225 (12)	0.0228 (12)	0.0250 (12)	0.0052 (10)	0.0108 (10)	0.0039 (10)
C4A	0.0210 (12)	0.0241 (13)	0.0241 (12)	0.0027 (10)	0.0088 (10)	0.0033 (10)
C5	0.0241 (13)	0.0248 (13)	0.0258 (13)	0.0001 (10)	0.0077 (10)	0.0053 (10)
C6	0.0266 (13)	0.0243 (13)	0.0232 (12)	−0.0005 (10)	0.0078 (10)	0.0060 (10)
C6A	0.0227 (12)	0.0261 (13)	0.0217 (12)	0.0019 (10)	0.0115 (10)	0.0052 (10)
C7	0.0230 (12)	0.0278 (13)	0.0234 (12)	0.0022 (10)	0.0115 (10)	0.0052 (10)
C8	0.0217 (12)	0.0297 (14)	0.0253 (13)	0.0040 (10)	0.0080 (10)	0.0086 (11)
C9	0.0263 (13)	0.0247 (13)	0.0290 (13)	0.0032 (10)	0.0127 (11)	0.0085 (11)
C10	0.0240 (12)	0.0229 (13)	0.0214 (12)	−0.0015 (10)	0.0077 (10)	0.0031 (10)
C10A	0.0208 (12)	0.0265 (13)	0.0227 (12)	0.0032 (10)	0.0088 (10)	0.0075 (10)
N11	0.0191 (10)	0.0262 (11)	0.0250 (10)	−0.0001 (8)	0.0062 (8)	0.0075 (9)
C11A	0.0245 (12)	0.0225 (13)	0.0244 (12)	0.0053 (10)	0.0104 (10)	0.0055 (10)
N41	0.0204 (10)	0.0237 (11)	0.0262 (11)	0.0025 (8)	0.0089 (8)	0.0072 (8)
C42	0.0255 (13)	0.0247 (13)	0.0285 (13)	0.0053 (11)	0.0114 (10)	0.0066 (10)
N43	0.0257 (11)	0.0255 (11)	0.0358 (12)	0.0040 (9)	0.0120 (9)	0.0058 (9)
C43A	0.0263 (13)	0.0268 (13)	0.0222 (12)	0.0040 (11)	0.0103 (10)	0.0053 (10)
C44	0.0264 (13)	0.0270 (14)	0.0271 (13)	−0.0012 (11)	0.0103 (11)	0.0015 (11)
C45	0.0252 (13)	0.0352 (15)	0.0223 (12)	0.0030 (11)	0.0097 (10)	0.0047 (11)
C46	0.0276 (13)	0.0315 (14)	0.0294 (13)	0.0098 (11)	0.0118 (11)	0.0082 (11)
C47	0.0281 (13)	0.0253 (13)	0.0305 (13)	0.0034 (11)	0.0132 (11)	0.0067 (11)
C47A	0.0225 (12)	0.0256 (13)	0.0216 (12)	0.0032 (10)	0.0092 (10)	0.0065 (10)
C48	0.0254 (13)	0.0400 (16)	0.0366 (15)	0.0031 (12)	0.0124 (11)	0.0072 (12)
C61	0.0390 (15)	0.0257 (13)	0.0310 (14)	0.0049 (11)	0.0155 (12)	0.0062 (11)
C71	0.0265 (13)	0.0305 (14)	0.0286 (13)	0.0012 (11)	0.0059 (11)	0.0077 (11)
C91	0.0383 (15)	0.0262 (14)	0.0331 (14)	0.0038 (12)	0.0097 (12)	0.0068 (11)
C111	0.0227 (13)	0.0316 (14)	0.0313 (13)	−0.0012 (11)	0.0101 (11)	0.0084 (11)

Geometric parameters (Å, º)

N1—C2	1.329 (3)	N41—C47A	1.395 (3)
N1—C11A	1.356 (3)	C42—N43	1.304 (3)
C2—N3	1.328 (3)	C42—H42	0.9500
C2—H2	0.9500	N43—C43A	1.396 (3)
N3—C4	1.341 (3)	C43A—C44	1.394 (3)
C4—C4A	1.387 (3)	C43A—C47A	1.401 (3)
C4—N41	1.427 (3)	C44—C45	1.378 (3)
C4A—C11A	1.421 (3)	C44—H44	0.9500
C4A—C5	1.509 (3)	C45—C46	1.408 (4)
C5—C6	1.536 (3)	C45—C48	1.507 (3)
C5—H5A	0.9900	C46—C47	1.384 (3)
C5—H5B	0.9900	C46—H46	0.9500
C6—C6A	1.509 (3)	C47—C47A	1.387 (3)
C6—C61	1.528 (3)	C47—H47	0.9500
C6—H6	1.0000	C48—H48A	0.9800
C6A—C10A	1.403 (3)	C48—H48B	0.9800
C6A—C7	1.405 (3)	C48—H48C	0.9800
C7—C8	1.386 (3)	C61—H61A	0.9800
C7—C71	1.512 (3)	C61—H61B	0.9800
C8—C9	1.388 (3)	C61—H61C	0.9800
C8—H8	0.9500	C71—H71A	0.9800
C9—C10	1.387 (3)	C71—H71B	0.9800
C9—C91	1.504 (3)	C71—H71C	0.9800
C10—C10A	1.396 (3)	C91—H91A	0.9800
C10—H10	0.9500	C91—H91B	0.9800
C10A—N11	1.439 (3)	C91—H91C	0.9800
N11—C11A	1.373 (3)	C111—H11A	0.9800
N11—C111	1.471 (3)	C111—H11B	0.9800
N41—C42	1.375 (3)	C111—H11C	0.9800
C2—N1—C11A	117.3 (2)	N43—C42—H42	122.8
N3—C2—N1	127.6 (2)	N41—C42—H42	122.8
N3—C2—H2	116.2	C42—N43—C43A	104.3 (2)
N1—C2—H2	116.2	C44—C43A—N43	129.8 (2)
C2—N3—C4	113.8 (2)	C44—C43A—C47A	119.7 (2)
N3—C4—C4A	126.2 (2)	N43—C43A—C47A	110.5 (2)
N3—C4—N41	113.9 (2)	C45—C44—C43A	119.2 (2)
C4A—C4—N41	119.9 (2)	C45—C44—H44	120.4
C4—C4A—C11A	113.9 (2)	C43A—C44—H44	120.4
C4—C4A—C5	119.8 (2)	C44—C45—C46	119.8 (2)
C11A—C4A—C5	126.1 (2)	C44—C45—C48	120.1 (2)
C4A—C5—C6	116.3 (2)	C46—C45—C48	120.1 (2)
C4A—C5—H5A	108.2	C47—C46—C45	122.4 (2)
C6—C5—H5A	108.2	C47—C46—H46	118.8
C4A—C5—H5B	108.2	C45—C46—H46	118.8
C6—C5—H5B	108.2	C46—C47—C47A	116.6 (2)
H5A—C5—H5B	107.4	C46—C47—H47	121.7
C6A—C6—C61	114.6 (2)	C47A—C47—H47	121.7
C6A—C6—C5	109.48 (19)	C47—C47A—N41	132.5 (2)
C61—C6—C5	113.21 (19)	C47—C47A—C43A	122.3 (2)
C6A—C6—H6	106.3	N41—C47A—C43A	105.0 (2)
C61—C6—H6	106.3	C45—C48—H48A	109.5
C5—C6—H6	106.3	C45—C48—H48B	109.5
C10A—C6A—C7	118.2 (2)	H48A—C48—H48B	109.5
C10A—C6A—C6	120.5 (2)	C45—C48—H48C	109.5
C7—C6A—C6	121.3 (2)	H48A—C48—H48C	109.5
C8—C7—C6A	119.7 (2)	H48B—C48—H48C	109.5
C8—C7—C71	117.9 (2)	C6—C61—H61A	109.5
C6A—C7—C71	122.3 (2)	C6—C61—H61B	109.5
C7—C8—C9	122.4 (2)	H61A—C61—H61B	109.5
C7—C8—H8	118.8	C6—C61—H61C	109.5
C9—C8—H8	118.8	H61A—C61—H61C	109.5
C10—C9—C8	117.9 (2)	H61B—C61—H61C	109.5
C10—C9—C91	121.8 (2)	C7—C71—H71A	109.5
C8—C9—C91	120.3 (2)	C7—C71—H71B	109.5
C9—C10—C10A	121.0 (2)	H71A—C71—H71B	109.5
C9—C10—H10	119.5	C7—C71—H71C	109.5
C10A—C10—H10	119.5	H71A—C71—H71C	109.5
C10—C10A—C6A	120.7 (2)	H71B—C71—H71C	109.5
C10—C10A—N11	116.3 (2)	C9—C91—H91A	109.5
C6A—C10A—N11	122.8 (2)	C9—C91—H91B	109.5
C11A—N11—C10A	126.84 (19)	H91A—C91—H91B	109.5
C11A—N11—C111	117.29 (19)	C9—C91—H91C	109.5
C10A—N11—C111	115.35 (18)	H91A—C91—H91C	109.5
N1—C11A—N11	113.8 (2)	H91B—C91—H91C	109.5
N1—C11A—C4A	121.0 (2)	N11—C111—H11A	109.5
N11—C11A—C4A	125.2 (2)	N11—C111—H11B	109.5
C42—N41—C47A	105.81 (18)	H11A—C111—H11B	109.5
C42—N41—C4	125.15 (19)	N11—C111—H11C	109.5
C47A—N41—C4	128.86 (19)	H11A—C111—H11C	109.5
N43—C42—N41	114.4 (2)	H11B—C111—H11C	109.5
C11A—N1—C2—N3	2.5 (4)	C2—N1—C11A—N11	179.8 (2)
N1—C2—N3—C4	−4.3 (4)	C2—N1—C11A—C4A	2.8 (3)
C2—N3—C4—C4A	0.8 (3)	C10A—N11—C11A—N1	160.9 (2)
C2—N3—C4—N41	−175.54 (19)	C111—N11—C11A—N1	−10.4 (3)
N3—C4—C4A—C11A	3.7 (3)	C10A—N11—C11A—C4A	−22.3 (4)
N41—C4—C4A—C11A	179.9 (2)	C111—N11—C11A—C4A	166.4 (2)
N3—C4—C4A—C5	−171.1 (2)	C4—C4A—C11A—N1	−5.5 (3)
N41—C4—C4A—C5	5.1 (3)	C5—C4A—C11A—N1	168.9 (2)
C4—C4A—C5—C6	148.2 (2)	C4—C4A—C11A—N11	177.9 (2)
C11A—C4A—C5—C6	−26.0 (3)	C5—C4A—C11A—N11	−7.7 (4)
C4A—C5—C6—C6A	75.0 (3)	N3—C4—N41—C42	64.4 (3)
C4A—C5—C6—C61	−54.2 (3)	C4A—C4—N41—C42	−112.2 (3)
C61—C6—C6A—C10A	67.8 (3)	N3—C4—N41—C47A	−121.0 (2)
C5—C6—C6A—C10A	−60.6 (3)	C4A—C4—N41—C47A	62.3 (3)
C61—C6—C6A—C7	−115.0 (2)	C47A—N41—C42—N43	−0.5 (3)
C5—C6—C6A—C7	116.5 (2)	C4—N41—C42—N43	175.1 (2)
C10A—C6A—C7—C8	−0.7 (3)	N41—C42—N43—C43A	0.5 (3)
C6—C6A—C7—C8	−177.9 (2)	C42—N43—C43A—C44	178.9 (2)
C10A—C6A—C7—C71	−179.8 (2)	C42—N43—C43A—C47A	−0.3 (3)
C6—C6A—C7—C71	3.0 (3)	N43—C43A—C44—C45	−177.9 (2)
C6A—C7—C8—C9	2.4 (4)	C47A—C43A—C44—C45	1.3 (3)
C71—C7—C8—C9	−178.5 (2)	C43A—C44—C45—C46	0.9 (3)
C7—C8—C9—C10	−1.4 (4)	C43A—C44—C45—C48	−178.2 (2)
C7—C8—C9—C91	177.6 (2)	C44—C45—C46—C47	−1.2 (4)
C8—C9—C10—C10A	−1.4 (4)	C48—C45—C46—C47	177.9 (2)
C91—C9—C10—C10A	179.7 (2)	C45—C46—C47—C47A	−0.8 (4)
C9—C10—C10A—C6A	3.0 (4)	C46—C47—C47A—N41	177.7 (2)
C9—C10—C10A—N11	−173.3 (2)	C46—C47—C47A—C43A	3.0 (3)
C7—C6A—C10A—C10	−1.9 (3)	C42—N41—C47A—C47	−175.1 (2)
C6—C6A—C10A—C10	175.3 (2)	C4—N41—C47A—C47	9.5 (4)
C7—C6A—C10A—N11	174.2 (2)	C42—N41—C47A—C43A	0.3 (2)
C6—C6A—C10A—N11	−8.6 (3)	C4—N41—C47A—C43A	−175.1 (2)
C10—C10A—N11—C11A	−130.0 (2)	C44—C43A—C47A—C47	−3.4 (3)
C6A—C10A—N11—C11A	53.7 (3)	N43—C43A—C47A—C47	176.0 (2)
C10—C10A—N11—C111	41.4 (3)	C44—C43A—C47A—N41	−179.3 (2)
C6A—C10A—N11—C111	−134.9 (2)	N43—C43A—C47A—N41	0.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C42—H42···N3^i	0.95	2.57	3.280 (3)	131

Symmetry code: (i) −x, −y+2, −z.