Structural insight from intermolecular interactions and energy framework analyses of 2-substituted 6,7,8,9-tetra­hydro-11H-pyrido[2,1-b]quinazolin-11-ones

The crystal structures of three mackinazolinone derivatives (2-amino-6,7,8,9-tetra­hydro-11H-pyrido[2,1-b]quinazolin-11-one at room temperature, and 2-nitro-6,7,8,9-tetra­hydro-11H-pyrido[2,1-b]quinazolin-11-one and N-(11-oxo-6,8,9,11-tetra­hydro-7H-pyrido[2,1-b]quinazolin-2-yl)benzamide at 100 K) are explored using X-ray crystallography. To delineate the different intermolecular interactions and the respective interaction energies in the crystal architectures, energy framework analyses were carried out using the CE-B3LYP/6-31G(d,p) method implemented in the CrystalExplorer software. In the structures the different molecules are linked by C—H...O, C—H...N and N—H...O hydrogen bonds. Together with these hydrogen bonds, C—H...π and C—O...π interactions are involved in the formation of a three-dimensional crystal network. A Hirshfeld surface analysis allows the visualization of the two-dimensional fingerprint plots and the quantification of the contributions of H...H, H...C/C...H and H...O/O...H contacts throughout the different crystal structures. To obtain additional information on the intrinsic properties of our targets and to compare the experimental crystal structures with their respective conformations in the gas phase, quantum chemical calculations at the B3LYP-D3BJ/6-311++G(d,p) level of theory, including Grimme's D3 correction term and BJ damping functions, were carried out to account for intramolecular dispersion inter­actions. The identified energy gaps between the highest occupied and the lowest unoccupied molecular orbitals (HOMO–LUMO gap) of our targets in the gas phase and in two implicit solvents (methanol and di­methyl sulfoxide) allow us to quantify the impact of different substituents on the reactivity of mackinazolinone derivatives.

Computing details

For all structures, data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2018). Molecular graphics: PLATON (Spek, 2020) for (2), (4); PLATON (Spek, 2009) for (3). Software used to prepare material for publication: publCIF (Westrip, 2010) for (2), (4).

(2)

Crystal data

C12H13N3O	F(000) = 456
Mr = 215.25	Dx = 1.361 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 9.6282 (3) Å	Cell parameters from 1630 reflections
b = 9.5416 (4) Å	θ = 3.9–75.5°
c = 11.6064 (4) Å	µ = 0.73 mm^−1
β = 99.863 (3)°	T = 298 K
V = 1050.50 (7) Å^3	Rod, colourless
Z = 4	0.20 × 0.20 × 0.20 mm

Data collection

Xcalibur, Ruby diffractometer	2124 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1439 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 10.2576 pixels mm^-1	θmax = 75.6°, θmin = 5.5°
ω scans	h = −11→9
Absorption correction: multi-scan CrysAlisPro, Oxford Diffraction, 2009	k = −11→10
Tmin = 0.881, Tmax = 1.000	l = −13→14
4385 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.173	w = 1/[σ^2(Fo^2) + (0.0917P)^2 + 0.143P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
2124 reflections	Δρmax = 0.38 e Å^−3
152 parameters	Δρmin = −0.20 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O	0.56471 (18)	0.1894 (2)	0.45187 (15)	0.0694 (6)
N'	0.0906 (2)	0.3549 (3)	0.5509 (2)	0.0620 (6)
H1A'	0.037 (3)	0.403 (3)	0.597 (3)	0.077 (9)*
H1B'	0.097 (4)	0.393 (4)	0.471 (4)	0.115*
C1	0.3202 (2)	0.2522 (2)	0.54959 (17)	0.0475 (5)
H1	0.315603	0.276579	0.471443	0.057*
C2	0.2111 (2)	0.2883 (2)	0.60774 (19)	0.0475 (5)
C3	0.2217 (2)	0.2515 (3)	0.72608 (19)	0.0522 (6)
H3	0.150765	0.277993	0.766783	0.063*
C4	0.3342 (2)	0.1776 (3)	0.78212 (19)	0.0525 (6)
H4	0.337699	0.152424	0.859966	0.063*
C4A	0.4454 (2)	0.1388 (2)	0.72413 (18)	0.0446 (5)
N5	0.55998 (17)	0.0647 (2)	0.78495 (16)	0.0495 (5)
C5A	0.6664 (2)	0.0421 (2)	0.7317 (2)	0.0469 (5)
C6	0.7900 (2)	−0.0381 (3)	0.7958 (2)	0.0596 (6)
H6A	0.778191	−0.136667	0.776212	0.071*
H6B	0.792178	−0.028570	0.879309	0.071*
C7	0.9294 (2)	0.0125 (3)	0.7662 (2)	0.0619 (7)
H7A	0.945205	0.109713	0.789179	0.074*
H7B	1.006434	−0.043182	0.807489	0.074*
C8	0.9218 (2)	−0.0025 (3)	0.6360 (3)	0.0674 (7)
H8A	1.010449	0.027690	0.615188	0.081*
H8B	0.908424	−0.100502	0.614754	0.081*
C9	0.8036 (2)	0.0821 (3)	0.5678 (2)	0.0582 (6)
H9A	0.836517	0.177325	0.560826	0.070*
H9B	0.780856	0.043574	0.489540	0.070*
N10	0.67213 (17)	0.08683 (19)	0.61957 (16)	0.0472 (5)
C11	0.5587 (2)	0.1536 (2)	0.55063 (19)	0.0481 (5)
C11A	0.4374 (2)	0.1791 (2)	0.60824 (17)	0.0429 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O	0.0717 (11)	0.0925 (14)	0.0493 (9)	0.0214 (10)	0.0251 (8)	0.0157 (9)
N'	0.0526 (11)	0.0819 (16)	0.0495 (11)	0.0195 (11)	0.0031 (9)	−0.0031 (11)
C1	0.0518 (12)	0.0556 (13)	0.0338 (10)	0.0024 (11)	0.0035 (8)	−0.0003 (9)
C2	0.0415 (10)	0.0528 (13)	0.0464 (11)	0.0000 (10)	0.0028 (9)	−0.0083 (10)
C3	0.0430 (11)	0.0683 (16)	0.0461 (12)	0.0027 (11)	0.0101 (9)	−0.0045 (11)
C4	0.0480 (11)	0.0713 (16)	0.0388 (11)	−0.0001 (11)	0.0090 (9)	0.0037 (11)
C4A	0.0421 (10)	0.0501 (12)	0.0406 (11)	−0.0016 (9)	0.0042 (8)	0.0022 (9)
N5	0.0407 (9)	0.0599 (12)	0.0469 (10)	0.0006 (8)	0.0046 (8)	0.0063 (9)
C5A	0.0450 (11)	0.0452 (12)	0.0483 (12)	−0.0007 (10)	0.0015 (9)	0.0026 (10)
C6	0.0522 (13)	0.0580 (15)	0.0658 (16)	0.0084 (11)	0.0024 (11)	0.0081 (12)
C7	0.0465 (12)	0.0640 (15)	0.0720 (17)	0.0043 (12)	0.0006 (11)	0.0000 (13)
C8	0.0482 (13)	0.0771 (18)	0.0766 (18)	0.0041 (13)	0.0099 (12)	−0.0082 (15)
C9	0.0510 (12)	0.0662 (15)	0.0608 (15)	0.0033 (12)	0.0196 (11)	0.0003 (12)
N10	0.0422 (9)	0.0493 (10)	0.0509 (10)	0.0041 (8)	0.0099 (8)	0.0000 (8)
C11	0.0530 (12)	0.0523 (13)	0.0389 (11)	0.0020 (10)	0.0077 (9)	0.0018 (9)
C11A	0.0427 (10)	0.0452 (11)	0.0401 (11)	−0.0015 (9)	0.0052 (8)	−0.0033 (9)

Geometric parameters (Å, º)

O—C11	1.207 (3)	N5—C5A	1.302 (3)
N'—C2	1.387 (3)	C5A—N10	1.380 (3)
C1—C2	1.386 (3)	C5A—C6	1.500 (3)
C1—C11A	1.399 (3)	C6—C7	1.520 (3)
C2—C3	1.404 (3)	C7—C8	1.507 (4)
C3—C4	1.360 (3)	C8—C9	1.505 (4)
C4—C4A	1.408 (3)	C9—N10	1.491 (3)
C4A—C11A	1.388 (3)	N10—C11	1.392 (3)
C4A—N5	1.396 (3)	C11—C11A	1.463 (3)
C2—C1—C11A	120.12 (19)	C5A—C6—C7	112.4 (2)
C1—C2—N'	121.7 (2)	C8—C7—C6	107.7 (2)
C1—C2—C3	118.68 (19)	C9—C8—C7	112.2 (2)
N'—C2—C3	119.6 (2)	N10—C9—C8	114.9 (2)
C4—C3—C2	121.1 (2)	C5A—N10—C11	121.96 (18)
C3—C4—C4A	121.0 (2)	C5A—N10—C9	122.97 (18)
C11A—C4A—N5	122.55 (19)	C11—N10—C9	114.74 (18)
C11A—C4A—C4	118.00 (19)	O—C11—N10	121.0 (2)
N5—C4A—C4	119.44 (19)	O—C11—C11A	124.0 (2)
C5A—N5—C4A	117.51 (18)	N10—C11—C11A	115.02 (18)
N5—C5A—N10	123.95 (19)	C4A—C11A—C1	121.04 (19)
N5—C5A—C6	118.1 (2)	C4A—C11A—C11	118.73 (19)
N10—C5A—C6	118.0 (2)	C1—C11A—C11	120.07 (19)
C11A—C1—C2—N'	−177.0 (2)	N5—C5A—N10—C9	169.0 (2)
C11A—C1—C2—C3	0.7 (3)	C6—C5A—N10—C9	−11.4 (3)
C1—C2—C3—C4	−2.3 (4)	C8—C9—N10—C5A	12.5 (3)
N'—C2—C3—C4	175.5 (2)	C8—C9—N10—C11	−174.0 (2)
C2—C3—C4—C4A	1.6 (4)	C5A—N10—C11—O	−178.5 (2)
C3—C4—C4A—C11A	0.5 (3)	C9—N10—C11—O	7.9 (3)
C3—C4—C4A—N5	179.1 (2)	C5A—N10—C11—C11A	3.2 (3)
C11A—C4A—N5—C5A	4.8 (3)	C9—N10—C11—C11A	−170.37 (19)
C4—C4A—N5—C5A	−173.7 (2)	N5—C4A—C11A—C1	179.4 (2)
C4A—N5—C5A—N10	−0.1 (3)	C4—C4A—C11A—C1	−2.1 (3)
C4A—N5—C5A—C6	−179.7 (2)	N5—C4A—C11A—C11	−5.3 (3)
N5—C5A—C6—C7	−145.6 (2)	C4—C4A—C11A—C11	173.2 (2)
N10—C5A—C6—C7	34.8 (3)	C2—C1—C11A—C4A	1.4 (3)
C5A—C6—C7—C8	−58.3 (3)	C2—C1—C11A—C11	−173.8 (2)
C6—C7—C8—C9	59.8 (3)	O—C11—C11A—C4A	−177.0 (2)
C7—C8—C9—N10	−37.3 (3)	N10—C11—C11A—C4A	1.2 (3)
N5—C5A—N10—C11	−4.0 (3)	O—C11—C11A—C1	−1.7 (4)
C6—C5A—N10—C11	175.6 (2)	N10—C11—C11A—C1	176.57 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N′—H1A′···N5^i	0.93 (3)	2.36 (3)	3.268 (3)	167 (3)
N′—H1B′···N5^ii	1.00 (4)	2.17 (4)	3.146 (3)	164 (3)
C3—H3···O^iii	0.93	2.45	3.291 (3)	150

Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) x−1/2, −y+1/2, z+1/2.

(3)

Crystal data

C12H11N3O3	F(000) = 512
Mr = 245.24	Dx = 1.494 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 13.0177 (3) Å	Cell parameters from 2233 reflections
b = 5.6433 (14) Å	θ = 3.5–75.5°
c = 15.4366 (4) Å	µ = 0.92 mm^−1
β = 105.949 (3)°	T = 100 K
V = 1090.4 (3) Å^3	Plate, colourless
Z = 4	0.50 × 0.40 × 0.15 mm

Data collection

Xcalibur, Ruby diffractometer	2226 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1777 reflections with I > 2σ(I)
Detector resolution: 10.2576 pixels mm^-1	Rint = 0.023
ω scans	θmax = 75.7°, θmin = 4.0°
Absorption correction: multi-scan CrysAlisPro, Oxford Diffraction, 2009	h = −12→16
Tmin = 0.710, Tmax = 1.000	k = −4→6
4411 measured reflections	l = −19→15

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.0746P)^2 + 0.0703P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
2226 reflections	Δρmax = 0.29 e Å^−3
163 parameters	Δρmin = −0.24 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O	0.33031 (8)	−0.32586 (19)	0.26740 (7)	0.0253 (3)
O'1	0.61695 (9)	−0.0346 (3)	0.13807 (8)	0.0403 (3)
O'2	0.71362 (9)	0.2653 (2)	0.19815 (8)	0.0344 (3)
N'	0.64191 (10)	0.1218 (3)	0.19517 (8)	0.0270 (3)
C1	0.50654 (11)	−0.0287 (3)	0.26350 (9)	0.0211 (3)
H1	0.495910	−0.160067	0.223516	0.025*
C2	0.58166 (10)	0.1408 (3)	0.26255 (9)	0.0210 (3)
C3	0.60190 (11)	0.3344 (3)	0.32164 (10)	0.0220 (3)
H3	0.655000	0.447849	0.319370	0.026*
C4	0.54309 (11)	0.3569 (3)	0.38326 (9)	0.0207 (3)
H4	0.556516	0.485256	0.424665	0.025*
C4A	0.46322 (10)	0.1898 (2)	0.38484 (9)	0.0178 (3)
N5	0.40190 (9)	0.2257 (2)	0.44384 (8)	0.0191 (3)
C5A	0.32489 (10)	0.0765 (2)	0.44146 (9)	0.0181 (3)
C6	0.25885 (11)	0.1215 (3)	0.50637 (9)	0.0210 (3)
H6A	0.253274	0.294703	0.514151	0.025*
H6B	0.296691	0.053883	0.565747	0.025*
C7	0.14660 (11)	0.0174 (3)	0.47687 (10)	0.0256 (3)
H7A	0.111516	0.032355	0.525966	0.031*
H7B	0.102938	0.103073	0.423405	0.031*
C8	0.15657 (12)	−0.2414 (3)	0.45431 (10)	0.0257 (3)
H8A	0.085130	−0.316611	0.438814	0.031*
H8B	0.202489	−0.324203	0.507484	0.031*
C9	0.20458 (11)	−0.2650 (3)	0.37553 (10)	0.0228 (3)
H9A	0.223240	−0.433154	0.369520	0.027*
H9B	0.150309	−0.218812	0.319467	0.027*
N10	0.30152 (9)	−0.1171 (2)	0.38558 (8)	0.0183 (3)
C11	0.35736 (11)	−0.1648 (3)	0.32178 (9)	0.0196 (3)
C11A	0.44587 (10)	−0.0026 (2)	0.32518 (9)	0.0180 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O	0.0293 (5)	0.0234 (5)	0.0239 (5)	−0.0033 (4)	0.0087 (4)	−0.0074 (4)
O'1	0.0335 (6)	0.0644 (9)	0.0275 (6)	−0.0036 (6)	0.0162 (5)	−0.0176 (6)
O'2	0.0334 (6)	0.0417 (7)	0.0361 (7)	−0.0019 (5)	0.0227 (5)	0.0018 (5)
N'	0.0225 (6)	0.0400 (8)	0.0202 (6)	0.0056 (5)	0.0087 (5)	0.0003 (6)
C1	0.0210 (6)	0.0254 (7)	0.0158 (6)	0.0055 (6)	0.0035 (5)	−0.0024 (6)
C2	0.0184 (6)	0.0299 (8)	0.0162 (6)	0.0068 (6)	0.0074 (5)	0.0020 (6)
C3	0.0182 (6)	0.0261 (7)	0.0228 (7)	0.0004 (6)	0.0073 (5)	0.0024 (6)
C4	0.0211 (6)	0.0212 (7)	0.0210 (7)	0.0004 (5)	0.0076 (5)	−0.0029 (5)
C4A	0.0181 (6)	0.0195 (7)	0.0159 (6)	0.0026 (5)	0.0048 (5)	−0.0001 (5)
N5	0.0205 (6)	0.0202 (6)	0.0180 (6)	0.0003 (5)	0.0080 (4)	−0.0019 (5)
C5A	0.0197 (6)	0.0188 (7)	0.0161 (6)	0.0026 (5)	0.0056 (5)	0.0011 (5)
C6	0.0229 (7)	0.0218 (7)	0.0209 (7)	−0.0001 (5)	0.0105 (5)	−0.0018 (6)
C7	0.0212 (7)	0.0325 (8)	0.0259 (7)	0.0006 (6)	0.0110 (6)	0.0001 (6)
C8	0.0256 (7)	0.0292 (8)	0.0239 (7)	−0.0073 (6)	0.0094 (6)	−0.0002 (6)
C9	0.0251 (7)	0.0223 (7)	0.0218 (7)	−0.0063 (6)	0.0079 (5)	−0.0005 (6)
N10	0.0194 (5)	0.0186 (6)	0.0171 (5)	−0.0014 (5)	0.0055 (4)	0.0009 (5)
C11	0.0213 (6)	0.0196 (7)	0.0172 (6)	0.0025 (5)	0.0043 (5)	−0.0001 (5)
C11A	0.0180 (6)	0.0199 (7)	0.0160 (6)	0.0037 (5)	0.0042 (5)	0.0005 (5)

Geometric parameters (Å, º)

O—C11	1.2218 (17)	C4A—C11A	1.4013 (19)
O'1—N'	1.2264 (18)	N5—C5A	1.3018 (18)
O'2—N'	1.2272 (17)	C5A—N10	1.3737 (18)
N'—C2	1.4687 (16)	C5A—C6	1.5102 (17)
C1—C2	1.371 (2)	C6—C7	1.5238 (19)
C1—C11A	1.4020 (18)	C7—C8	1.515 (2)
C2—C3	1.401 (2)	C8—C9	1.5182 (19)
C3—C4	1.3811 (18)	C9—N10	1.4851 (17)
C4—C4A	1.4088 (19)	N10—C11	1.4015 (16)
C4A—N5	1.3812 (16)	C11—C11A	1.4608 (19)
O'1—N'—O'2	123.41 (12)	N10—C5A—C6	118.82 (12)
O'1—N'—C2	118.29 (13)	C5A—C6—C7	114.27 (12)
O'2—N'—C2	118.29 (13)	C8—C7—C6	107.72 (12)
C2—C1—C11A	118.07 (13)	C7—C8—C9	110.43 (12)
C1—C2—C3	122.97 (12)	N10—C9—C8	113.07 (11)
C1—C2—N'	118.55 (13)	C5A—N10—C11	121.71 (12)
C3—C2—N'	118.47 (13)	C5A—N10—C9	123.23 (11)
C4—C3—C2	118.66 (13)	C11—N10—C9	114.13 (11)
C3—C4—C4A	120.11 (13)	O—C11—N10	121.21 (13)
N5—C4A—C11A	121.95 (12)	O—C11—C11A	124.50 (13)
N5—C4A—C4	118.43 (12)	N10—C11—C11A	114.26 (12)
C11A—C4A—C4	119.59 (12)	C4A—C11A—C1	120.56 (13)
C5A—N5—C4A	117.81 (12)	C4A—C11A—C11	119.48 (12)
N5—C5A—N10	124.63 (12)	C1—C11A—C11	119.72 (13)
N5—C5A—C6	116.55 (12)
C11A—C1—C2—C3	1.6 (2)	N5—C5A—N10—C11	−3.1 (2)
C11A—C1—C2—N'	−176.95 (12)	C6—C5A—N10—C11	177.88 (12)
O'1—N'—C2—C1	5.5 (2)	N5—C5A—N10—C9	−171.42 (12)
O'2—N'—C2—C1	−175.52 (13)	C6—C5A—N10—C9	9.57 (19)
O'1—N'—C2—C3	−173.09 (13)	C8—C9—N10—C5A	−20.92 (19)
O'2—N'—C2—C3	5.9 (2)	C8—C9—N10—C11	169.96 (12)
C1—C2—C3—C4	−0.5 (2)	C5A—N10—C11—O	−173.86 (13)
N'—C2—C3—C4	178.02 (12)	C9—N10—C11—O	−4.55 (19)
C2—C3—C4—C4A	−1.2 (2)	C5A—N10—C11—C11A	4.33 (18)
C3—C4—C4A—N5	−176.29 (12)	C9—N10—C11—C11A	173.64 (11)
C3—C4—C4A—C11A	1.7 (2)	N5—C4A—C11A—C1	177.31 (12)
C11A—C4A—N5—C5A	−1.33 (19)	C4—C4A—C11A—C1	−0.6 (2)
C4—C4A—N5—C5A	176.63 (12)	N5—C4A—C11A—C11	2.94 (19)
C4A—N5—C5A—N10	1.3 (2)	C4—C4A—C11A—C11	−175.00 (12)
C4A—N5—C5A—C6	−179.62 (11)	C2—C1—C11A—C4A	−1.0 (2)
N5—C5A—C6—C7	155.44 (13)	C2—C1—C11A—C11	173.38 (12)
N10—C5A—C6—C7	−25.47 (18)	O—C11—C11A—C4A	173.87 (13)
C5A—C6—C7—C8	51.56 (16)	N10—C11—C11A—C4A	−4.26 (18)
C6—C7—C8—C9	−63.01 (16)	O—C11—C11A—C1	−0.5 (2)
C7—C8—C9—N10	47.86 (17)	N10—C11—C11A—C1	−178.67 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O′2^i	0.95	2.54	3.4899 (19)	175
C4—H4···N5^ii	0.95	2.54	3.4834 (19)	170
C9—H9B···O^iii	0.99	2.64	3.2659 (18)	121

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1/2, y+1/2, −z+1/2.

(4)

Crystal data

C19H17N3O2	F(000) = 1344
Mr = 319.35	Dx = 1.376 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 10.6548 (3) Å	Cell parameters from 4480 reflections
b = 12.6232 (3) Å	θ = 3.5–75.7°
c = 22.9326 (6) Å	µ = 0.74 mm^−1
β = 91.457 (3)°	T = 100 K
V = 3083.38 (14) Å^3	Prismatic, colourless
Z = 8	0.30 × 0.20 × 0.20 mm

Data collection

Xcalibur, Ruby diffractometer	6257 independent reflections
Radiation source: Enhance (Cu) X-ray Source	4394 reflections with I > 2σ(I)
Detector resolution: 10.2576 pixels mm^-1	Rint = 0.037
ω scans	θmax = 75.8°, θmin = 3.9°
Absorption correction: multi-scan CrysAlisPro, Oxford Diffraction, 2009	h = −13→9
Tmin = 0.798, Tmax = 1.000	k = −9→15
13441 measured reflections	l = −28→28

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.0697P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max < 0.001
6257 reflections	Δρmax = 0.23 e Å^−3
440 parameters	Δρmin = −0.27 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N'	0.20635 (14)	−0.06986 (11)	−0.01815 (7)	0.0177 (3)
H1A'	0.243 (2)	−0.1357 (17)	−0.0176 (9)	0.031 (6)*
O'	0.20915 (12)	0.10014 (9)	0.01560 (5)	0.0216 (3)
C1	0.04761 (16)	0.03155 (13)	−0.07541 (7)	0.0169 (3)
H1	0.070309	0.096016	−0.056555	0.020*
C1'	0.37132 (16)	−0.01400 (13)	0.05138 (7)	0.0173 (4)
O1	−0.08754 (12)	0.21519 (9)	−0.11290 (5)	0.0218 (3)
C2	0.10840 (16)	−0.06185 (13)	−0.06059 (7)	0.0165 (3)
C2'	0.43847 (17)	−0.10833 (14)	0.04804 (8)	0.0203 (4)
H2'	0.406911	−0.164921	0.024618	0.024*
C3	0.07318 (17)	−0.15684 (13)	−0.08966 (7)	0.0185 (4)
H3	0.115032	−0.221074	−0.079785	0.022*
C3'	0.55187 (18)	−0.11987 (14)	0.07898 (8)	0.0225 (4)
H3'	0.597616	−0.184257	0.076574	0.027*
C4	−0.02049 (17)	−0.15734 (13)	−0.13186 (7)	0.0189 (4)
H4	−0.042669	−0.221818	−0.150840	0.023*
C4'	0.59791 (18)	−0.03771 (14)	0.11319 (8)	0.0240 (4)
H4'	0.676061	−0.045246	0.133642	0.029*
C4A	−0.08388 (17)	−0.06353 (13)	−0.14727 (7)	0.0175 (4)
N5	−0.17937 (14)	−0.06669 (11)	−0.18972 (6)	0.0182 (3)
C5'	0.53021 (19)	0.05577 (15)	0.11772 (8)	0.0250 (4)
H5'	0.561161	0.111505	0.141919	0.030*
C5A	−0.23902 (17)	0.02073 (13)	−0.20157 (7)	0.0176 (4)
C6	−0.34776 (17)	0.01584 (13)	−0.24478 (8)	0.0209 (4)
H6A	−0.421815	−0.012891	−0.224901	0.025*
H6B	−0.326548	−0.034087	−0.276329	0.025*
C6'	0.41745 (18)	0.06779 (14)	0.08693 (8)	0.0223 (4)
H6'	0.371369	0.131894	0.090014	0.027*
C7	−0.38289 (18)	0.12224 (14)	−0.27193 (8)	0.0219 (4)
H7A	−0.316206	0.145906	−0.298248	0.026*
H7B	−0.462260	0.115665	−0.295041	0.026*
C8	−0.39839 (18)	0.20187 (14)	−0.22323 (8)	0.0224 (4)
H8A	−0.428443	0.270087	−0.239665	0.027*
H8B	−0.461693	0.175808	−0.195805	0.027*
C9	−0.27460 (17)	0.21828 (13)	−0.19110 (8)	0.0218 (4)
H9A	−0.218914	0.260947	−0.215806	0.026*
H9B	−0.289290	0.259078	−0.155042	0.026*
N10	−0.21016 (14)	0.11761 (11)	−0.17538 (6)	0.0176 (3)
C11	−0.11300 (16)	0.12743 (13)	−0.13402 (7)	0.0168 (3)
C11A	−0.04797 (16)	0.02991 (13)	−0.11862 (7)	0.0161 (3)
C12	0.25443 (17)	0.01106 (13)	0.01536 (7)	0.0174 (4)
O'A	1.12370 (12)	0.57114 (9)	−0.13152 (5)	0.0214 (3)
N'A	0.99853 (14)	0.43176 (11)	−0.10650 (7)	0.0187 (3)
H'A	0.9816 (19)	0.3648 (16)	−0.1111 (8)	0.022*
C1A	0.84051 (16)	0.41220 (13)	−0.03504 (7)	0.0167 (3)
H1A	0.850020	0.337626	−0.038318	0.020*
O1A	0.68461 (12)	0.28595 (9)	0.03716 (5)	0.0214 (3)
C1'A	1.15860 (16)	0.40492 (14)	−0.17763 (7)	0.0190 (4)
C2A	0.91416 (16)	0.47886 (13)	−0.06757 (7)	0.0171 (4)
C2'A	1.16697 (18)	0.29544 (15)	−0.17028 (8)	0.0251 (4)
H2'A	1.133319	0.262817	−0.136777	0.030*
C3A	0.89915 (17)	0.58995 (13)	−0.06187 (7)	0.0182 (4)
H3A	0.950511	0.636426	−0.083460	0.022*
C3'A	1.2246 (2)	0.23461 (15)	−0.21209 (9)	0.0307 (5)
H3'A	1.229283	0.159977	−0.207151	0.037*
C4AA	0.81077 (18)	0.63121 (13)	−0.02532 (8)	0.0203 (4)
H4AA	0.800740	0.705801	−0.022521	0.024*
C4AB	0.73542 (17)	0.56399 (13)	0.00782 (7)	0.0175 (4)
C4'A	1.27577 (18)	0.28063 (16)	−0.26117 (8)	0.0270 (4)
H4'A	1.314302	0.237964	−0.289770	0.032*
N5A	0.64844 (14)	0.60700 (11)	0.04506 (6)	0.0205 (3)
C5AB	0.58566 (16)	0.54345 (13)	0.07766 (7)	0.0180 (4)
C5'A	1.26976 (19)	0.38956 (16)	−0.26775 (8)	0.0270 (4)
H5'A	1.305514	0.422234	−0.300743	0.032*
C6'A	1.21170 (18)	0.45089 (15)	−0.22629 (8)	0.0241 (4)
H6'A	1.208054	0.525575	−0.231157	0.029*
C6A	0.49754 (18)	0.59253 (14)	0.12060 (8)	0.0236 (4)
H6AA	0.447364	0.647632	0.099999	0.028*
H6AB	0.548543	0.628416	0.151412	0.028*
C7A	0.40798 (18)	0.51692 (14)	0.14971 (8)	0.0251 (4)
H7AA	0.371563	0.551288	0.184206	0.030*
H7AB	0.338510	0.497992	0.122168	0.030*
C8A	0.47884 (19)	0.41812 (15)	0.16823 (8)	0.0275 (4)
H8AA	0.549752	0.437558	0.194847	0.033*
H8AB	0.422367	0.370224	0.189482	0.033*
C9A	0.52811 (19)	0.36190 (14)	0.11529 (9)	0.0259 (4)
H9AA	0.584158	0.303483	0.128277	0.031*
H9AB	0.456728	0.330385	0.092909	0.031*
N10A	0.59807 (14)	0.43378 (11)	0.07662 (6)	0.0185 (3)
C11C	0.67862 (16)	0.38367 (13)	0.03843 (7)	0.0171 (4)
C11B	0.75229 (16)	0.45387 (13)	0.00259 (7)	0.0166 (4)
C12A	1.09334 (16)	0.47725 (13)	−0.13591 (7)	0.0187 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N'	0.0183 (7)	0.0102 (7)	0.0246 (7)	0.0015 (6)	−0.0028 (6)	−0.0005 (6)
O'	0.0247 (7)	0.0123 (6)	0.0278 (6)	0.0012 (5)	−0.0027 (6)	−0.0029 (5)
C1	0.0197 (9)	0.0102 (8)	0.0210 (8)	−0.0006 (7)	0.0013 (7)	−0.0015 (7)
C1'	0.0176 (8)	0.0149 (8)	0.0194 (8)	−0.0028 (7)	0.0022 (7)	0.0020 (7)
O1	0.0256 (7)	0.0102 (6)	0.0295 (7)	0.0011 (5)	−0.0036 (5)	−0.0025 (5)
C2	0.0167 (8)	0.0123 (8)	0.0206 (8)	−0.0010 (7)	0.0016 (7)	−0.0001 (7)
C2'	0.0229 (9)	0.0150 (8)	0.0229 (8)	−0.0019 (7)	−0.0013 (7)	−0.0015 (7)
C3	0.0226 (9)	0.0099 (8)	0.0229 (8)	0.0018 (7)	0.0016 (7)	−0.0001 (7)
C3'	0.0235 (9)	0.0171 (8)	0.0271 (9)	0.0005 (7)	0.0016 (8)	0.0045 (8)
C4	0.0259 (9)	0.0102 (8)	0.0208 (8)	−0.0014 (7)	0.0020 (7)	−0.0028 (7)
C4'	0.0241 (10)	0.0232 (9)	0.0245 (9)	−0.0038 (8)	−0.0042 (8)	0.0047 (8)
C4A	0.0197 (9)	0.0129 (8)	0.0200 (8)	−0.0012 (7)	0.0014 (7)	−0.0001 (7)
N5	0.0208 (8)	0.0122 (7)	0.0214 (7)	0.0000 (6)	−0.0016 (6)	−0.0004 (6)
C5'	0.0299 (10)	0.0182 (9)	0.0267 (9)	−0.0049 (8)	−0.0058 (8)	−0.0006 (8)
C5A	0.0213 (9)	0.0124 (8)	0.0193 (8)	−0.0001 (7)	0.0018 (7)	0.0001 (7)
C6	0.0224 (9)	0.0142 (8)	0.0259 (9)	0.0007 (7)	−0.0025 (8)	−0.0016 (7)
C6'	0.0254 (10)	0.0158 (8)	0.0256 (9)	−0.0006 (7)	−0.0015 (8)	−0.0004 (7)
C7	0.0236 (9)	0.0183 (9)	0.0235 (9)	0.0014 (7)	−0.0034 (7)	−0.0001 (8)
C8	0.0239 (9)	0.0165 (8)	0.0267 (9)	0.0040 (7)	−0.0024 (8)	0.0001 (8)
C9	0.0270 (10)	0.0102 (8)	0.0279 (9)	0.0049 (7)	−0.0053 (8)	0.0000 (7)
N10	0.0211 (8)	0.0099 (7)	0.0218 (7)	0.0020 (6)	0.0003 (6)	−0.0005 (6)
C11	0.0195 (8)	0.0105 (8)	0.0206 (8)	−0.0006 (7)	0.0020 (7)	−0.0003 (7)
C11A	0.0180 (8)	0.0093 (8)	0.0211 (8)	0.0011 (7)	0.0030 (7)	0.0002 (7)
C12	0.0198 (9)	0.0131 (8)	0.0193 (8)	−0.0009 (7)	0.0012 (7)	0.0001 (7)
O'A	0.0234 (7)	0.0157 (6)	0.0252 (6)	−0.0033 (5)	0.0004 (5)	−0.0009 (5)
N'A	0.0208 (8)	0.0113 (7)	0.0241 (7)	−0.0013 (6)	0.0023 (6)	−0.0022 (6)
C1A	0.0194 (8)	0.0092 (7)	0.0214 (8)	0.0007 (7)	−0.0038 (7)	−0.0014 (7)
O1A	0.0231 (7)	0.0103 (6)	0.0310 (7)	0.0011 (5)	0.0018 (6)	0.0001 (5)
C1'A	0.0170 (8)	0.0179 (8)	0.0218 (8)	0.0014 (7)	−0.0027 (7)	0.0007 (7)
C2A	0.0178 (8)	0.0136 (8)	0.0196 (8)	0.0023 (7)	−0.0016 (7)	−0.0022 (7)
C2'A	0.0271 (10)	0.0204 (9)	0.0282 (9)	0.0049 (8)	0.0068 (8)	0.0024 (8)
C3A	0.0218 (9)	0.0126 (8)	0.0204 (8)	−0.0009 (7)	0.0021 (7)	0.0012 (7)
C3'A	0.0345 (11)	0.0193 (9)	0.0386 (11)	0.0070 (9)	0.0078 (9)	−0.0008 (9)
C4AA	0.0277 (10)	0.0095 (8)	0.0237 (9)	0.0027 (7)	−0.0013 (8)	−0.0010 (7)
C4AB	0.0201 (9)	0.0110 (8)	0.0214 (8)	0.0019 (7)	−0.0023 (7)	−0.0017 (7)
C4'A	0.0258 (10)	0.0294 (10)	0.0258 (9)	0.0085 (8)	0.0020 (8)	−0.0018 (8)
N5A	0.0252 (8)	0.0120 (7)	0.0243 (7)	0.0021 (6)	0.0009 (7)	−0.0024 (6)
C5AB	0.0197 (9)	0.0116 (8)	0.0226 (8)	0.0020 (7)	−0.0017 (7)	−0.0018 (7)
C5'A	0.0259 (10)	0.0303 (10)	0.0249 (9)	0.0062 (8)	0.0028 (8)	0.0062 (8)
C6'A	0.0230 (9)	0.0204 (9)	0.0288 (9)	0.0027 (8)	−0.0004 (8)	0.0035 (8)
C6A	0.0258 (10)	0.0166 (9)	0.0287 (9)	0.0042 (8)	0.0043 (8)	−0.0029 (8)
C7A	0.0258 (10)	0.0206 (9)	0.0293 (10)	0.0046 (8)	0.0056 (8)	−0.0002 (8)
C8A	0.0278 (10)	0.0253 (10)	0.0297 (10)	0.0011 (8)	0.0062 (8)	0.0037 (8)
C9A	0.0282 (10)	0.0148 (8)	0.0351 (10)	−0.0001 (8)	0.0101 (9)	0.0033 (8)
N10A	0.0187 (7)	0.0116 (7)	0.0254 (7)	0.0000 (6)	0.0025 (6)	0.0001 (6)
C11C	0.0174 (8)	0.0104 (8)	0.0232 (8)	0.0016 (7)	−0.0045 (7)	−0.0022 (7)
C11B	0.0189 (8)	0.0105 (8)	0.0201 (8)	0.0006 (7)	−0.0039 (7)	−0.0019 (7)
C12A	0.0184 (8)	0.0156 (8)	0.0220 (8)	0.0004 (7)	−0.0042 (7)	0.0021 (7)

Geometric parameters (Å, º)

N'—C12	1.370 (2)	O'A—C12A	1.232 (2)
N'—C2	1.412 (2)	N'A—C12A	1.356 (2)
O'—C12	1.224 (2)	N'A—C2A	1.414 (2)
C1—C2	1.383 (2)	C1A—C2A	1.382 (2)
C1—C11A	1.403 (2)	C1A—C11B	1.395 (2)
C1'—C2'	1.392 (2)	O1A—C11C	1.235 (2)
C1'—C6'	1.397 (2)	C1'A—C6'A	1.391 (2)
C1'—C12	1.510 (2)	C1'A—C2'A	1.395 (2)
O1—C11	1.236 (2)	C1'A—C12A	1.505 (2)
C2—C3	1.418 (2)	C2A—C3A	1.418 (2)
C2'—C3'	1.393 (2)	C2'A—C3'A	1.384 (3)
C3—C4	1.372 (2)	C3A—C4AA	1.379 (2)
C3'—C4'	1.383 (2)	C3'A—C4'A	1.390 (3)
C4—C4A	1.404 (2)	C4AA—C4AB	1.405 (2)
C4'—C5'	1.388 (3)	C4AB—N5A	1.387 (2)
C4A—N5	1.391 (2)	C4AB—C11B	1.407 (2)
C4A—C11A	1.399 (2)	C4'A—C5'A	1.385 (3)
N5—C5A	1.299 (2)	N5A—C5AB	1.294 (2)
C5'—C6'	1.386 (3)	C5AB—N10A	1.391 (2)
C5A—N10	1.393 (2)	C5AB—C6A	1.511 (2)
C5A—C6	1.507 (2)	C5'A—C6'A	1.384 (3)
C6—C7	1.523 (2)	C6A—C7A	1.516 (2)
C7—C8	1.515 (2)	C7A—C8A	1.513 (2)
C8—C9	1.509 (2)	C8A—C9A	1.512 (2)
C9—N10	1.484 (2)	C9A—N10A	1.483 (2)
N10—C11	1.392 (2)	N10A—C11C	1.393 (2)
C11—C11A	1.452 (2)	C11C—C11B	1.452 (2)
C12—N'—C2	126.32 (15)	C12A—N'A—C2A	129.01 (15)
C2—C1—C11A	119.21 (16)	C2A—C1A—C11B	120.34 (16)
C2'—C1'—C6'	119.38 (17)	C6'A—C1'A—C2'A	118.97 (17)
C2'—C1'—C12	124.52 (15)	C6'A—C1'A—C12A	117.44 (16)
C6'—C1'—C12	115.93 (16)	C2'A—C1'A—C12A	123.59 (16)
C1—C2—N'	124.30 (15)	C1A—C2A—N'A	117.62 (15)
C1—C2—C3	119.24 (16)	C1A—C2A—C3A	119.04 (16)
N'—C2—C3	116.46 (15)	N'A—C2A—C3A	123.30 (16)
C1'—C2'—C3'	120.10 (16)	C3'A—C2'A—C1'A	119.61 (18)
C4—C3—C2	120.96 (16)	C4AA—C3A—C2A	120.67 (16)
C4'—C3'—C2'	120.07 (17)	C2'A—C3'A—C4'A	121.26 (18)
C3—C4—C4A	120.67 (16)	C3A—C4AA—C4AB	120.62 (16)
C3'—C4'—C5'	120.16 (18)	N5A—C4AB—C4AA	119.79 (15)
N5—C4A—C11A	122.64 (16)	N5A—C4AB—C11B	121.87 (16)
N5—C4A—C4	119.38 (15)	C4AA—C4AB—C11B	118.34 (16)
C11A—C4A—C4	117.97 (16)	C5'A—C4'A—C3'A	119.03 (18)
C5A—N5—C4A	117.87 (15)	C5AB—N5A—C4AB	118.44 (15)
C6'—C5'—C4'	120.01 (17)	N5A—C5AB—N10A	123.80 (16)
N5—C5A—N10	123.65 (16)	N5A—C5AB—C6A	117.46 (15)
N5—C5A—C6	117.83 (15)	N10A—C5AB—C6A	118.70 (15)
N10—C5A—C6	118.49 (15)	C6'A—C5'A—C4'A	120.06 (18)
C5A—C6—C7	114.18 (15)	C5'A—C6'A—C1'A	121.05 (18)
C5'—C6'—C1'	120.24 (17)	C5AB—C6A—C7A	115.93 (15)
C8—C7—C6	108.30 (14)	C8A—C7A—C6A	109.10 (15)
C9—C8—C7	109.93 (15)	C9A—C8A—C7A	110.03 (16)
N10—C9—C8	113.22 (14)	N10A—C9A—C8A	112.52 (15)
C11—N10—C5A	121.60 (14)	C5AB—N10A—C11C	121.52 (15)
C11—N10—C9	114.88 (14)	C5AB—N10A—C9A	123.32 (15)
C5A—N10—C9	123.45 (14)	C11C—N10A—C9A	115.16 (14)
O1—C11—N10	119.92 (15)	O1A—C11C—N10A	120.07 (16)
O1—C11—C11A	124.46 (16)	O1A—C11C—C11B	124.52 (16)
N10—C11—C11A	115.62 (14)	N10A—C11C—C11B	115.41 (15)
C4A—C11A—C1	121.94 (16)	C1A—C11B—C4AB	120.97 (16)
C4A—C11A—C11	118.53 (16)	C1A—C11B—C11C	120.16 (15)
C1—C11A—C11	119.52 (15)	C4AB—C11B—C11C	118.84 (16)
O'—C12—N'	123.10 (16)	O'A—C12A—N'A	124.33 (17)
O'—C12—C1'	120.64 (16)	O'A—C12A—C1'A	120.72 (16)
N'—C12—C1'	116.23 (15)	N'A—C12A—C1'A	114.91 (15)
C11A—C1—C2—N'	179.56 (15)	C11B—C1A—C2A—N'A	−177.71 (15)
C11A—C1—C2—C3	0.4 (2)	C11B—C1A—C2A—C3A	0.3 (2)
C12—N'—C2—C1	1.4 (3)	C12A—N'A—C2A—C1A	−168.46 (17)
C12—N'—C2—C3	−179.40 (16)	C12A—N'A—C2A—C3A	13.6 (3)
C6'—C1'—C2'—C3'	−1.3 (3)	C6'A—C1'A—C2'A—C3'A	−1.7 (3)
C12—C1'—C2'—C3'	173.78 (16)	C12A—C1'A—C2'A—C3'A	177.48 (17)
C1—C2—C3—C4	−0.4 (3)	C1A—C2A—C3A—C4AA	−1.3 (3)
N'—C2—C3—C4	−179.63 (16)	N'A—C2A—C3A—C4AA	176.67 (16)
C1'—C2'—C3'—C4'	0.1 (3)	C1'A—C2'A—C3'A—C4'A	0.7 (3)
C2—C3—C4—C4A	0.0 (3)	C2A—C3A—C4AA—C4AB	1.2 (3)
C2'—C3'—C4'—C5'	1.2 (3)	C3A—C4AA—C4AB—N5A	178.95 (16)
C3—C4—C4A—N5	−179.27 (16)	C3A—C4AA—C4AB—C11B	−0.2 (3)
C3—C4—C4A—C11A	0.4 (3)	C2'A—C3'A—C4'A—C5'A	0.7 (3)
C11A—C4A—N5—C5A	−2.0 (3)	C4AA—C4AB—N5A—C5AB	−175.89 (16)
C4—C4A—N5—C5A	177.71 (16)	C11B—C4AB—N5A—C5AB	3.2 (2)
C3'—C4'—C5'—C6'	−1.4 (3)	C4AB—N5A—C5AB—N10A	−1.6 (3)
C4A—N5—C5A—N10	1.9 (3)	C4AB—N5A—C5AB—C6A	176.18 (15)
C4A—N5—C5A—C6	−176.21 (15)	C3'A—C4'A—C5'A—C6'A	−1.0 (3)
N5—C5A—C6—C7	−159.86 (16)	C4'A—C5'A—C6'A—C1'A	0.0 (3)
N10—C5A—C6—C7	21.9 (2)	C2'A—C1'A—C6'A—C5'A	1.4 (3)
C4'—C5'—C6'—C1'	0.2 (3)	C12A—C1'A—C6'A—C5'A	−177.85 (17)
C2'—C1'—C6'—C5'	1.2 (3)	N5A—C5AB—C6A—C7A	168.85 (16)
C12—C1'—C6'—C5'	−174.33 (16)	N10A—C5AB—C6A—C7A	−13.3 (2)
C5A—C6—C7—C8	−51.1 (2)	C5AB—C6A—C7A—C8A	43.9 (2)
C6—C7—C8—C9	64.22 (19)	C6A—C7A—C8A—C9A	−62.8 (2)
C7—C8—C9—N10	−47.7 (2)	C7A—C8A—C9A—N10A	50.8 (2)
N5—C5A—N10—C11	0.2 (3)	N5A—C5AB—N10A—C11C	−1.7 (3)
C6—C5A—N10—C11	178.39 (16)	C6A—C5AB—N10A—C11C	−179.40 (15)
N5—C5A—N10—C9	176.99 (17)	N5A—C5AB—N10A—C9A	178.32 (17)
C6—C5A—N10—C9	−4.9 (2)	C6A—C5AB—N10A—C9A	0.6 (3)
C8—C9—N10—C11	−164.95 (15)	C8A—C9A—N10A—C5AB	−19.7 (3)
C8—C9—N10—C5A	18.1 (2)	C8A—C9A—N10A—C11C	160.24 (16)
C5A—N10—C11—O1	177.88 (16)	C5AB—N10A—C11C—O1A	−177.62 (16)
C9—N10—C11—O1	0.9 (2)	C9A—N10A—C11C—O1A	2.4 (2)
C5A—N10—C11—C11A	−2.3 (2)	C5AB—N10A—C11C—C11B	3.1 (2)
C9—N10—C11—C11A	−179.31 (14)	C9A—N10A—C11C—C11B	−176.91 (15)
N5—C4A—C11A—C1	179.25 (15)	C2A—C1A—C11B—C4AB	0.7 (2)
C4—C4A—C11A—C1	−0.4 (3)	C2A—C1A—C11B—C11C	−177.54 (15)
N5—C4A—C11A—C11	−0.1 (3)	N5A—C4AB—C11B—C1A	−179.85 (15)
C4—C4A—C11A—C11	−179.82 (15)	C4AA—C4AB—C11B—C1A	−0.8 (2)
C2—C1—C11A—C4A	0.0 (3)	N5A—C4AB—C11B—C11C	−1.6 (2)
C2—C1—C11A—C11	179.41 (15)	C4AA—C4AB—C11B—C11C	177.47 (15)
O1—C11—C11A—C4A	−178.01 (17)	O1A—C11C—C11B—C1A	−2.5 (3)
N10—C11—C11A—C4A	2.2 (2)	N10A—C11C—C11B—C1A	176.78 (15)
O1—C11—C11A—C1	2.6 (3)	O1A—C11C—C11B—C4AB	179.27 (17)
N10—C11—C11A—C1	−177.22 (15)	N10A—C11C—C11B—C4AB	−1.5 (2)
C2—N'—C12—O'	6.6 (3)	C2A—N'A—C12A—O'A	2.2 (3)
C2—N'—C12—C1'	−171.41 (15)	C2A—N'A—C12A—C1'A	−175.40 (16)
C2'—C1'—C12—O'	−171.22 (17)	C6'A—C1'A—C12A—O'A	−26.6 (2)
C6'—C1'—C12—O'	4.0 (2)	C2'A—C1'A—C12A—O'A	154.22 (18)
C2'—C1'—C12—N'	6.8 (3)	C6'A—C1'A—C12A—N'A	151.12 (16)
C6'—C1'—C12—N'	−177.94 (15)	C2'A—C1'A—C12A—N'A	−28.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N′—H1A′···O1A^i	0.92 (2)	2.10 (2)	3.0011 (18)	166.6 (19)
C1—H1···O′	0.95	2.19	2.808 (2)	122
C3—H3···O1A^i	0.95	2.47	3.257 (2)	141
N′A—H′A···O1^ii	0.87 (2)	2.03 (2)	2.8861 (18)	169.0 (19)
C1A—H1A···O1^ii	0.95	2.41	3.167 (2)	136
C3A—H3A···O′A	0.95	2.32	2.920 (2)	120
C4AA—H4AA···O′^iii	0.95	2.46	3.405 (2)	176

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