Using structural mimics for accessing and exploring structural landscapes of poorly soluble molecular solids

The importance of using structural mimics for mapping out the structural landscape of a poorly soluble active pharmaceutical ingredient was investigated using erlotinib as an example. A mimic was synthesized by preserving the main molecular functionalities responsible for creating the most probable structural arrangements in the solid state. Calculated molecular electrostatic potentials on both erlotinib and the mimic showed very comparable values indicating that the latter would be able to form hydrogen bonds of similar probability and strength as those of erlotinib. In order to establish the binding preference in co-crystallization experiments, the mimic molecule was co-crystallized with US Food and Drug Administration approved dicarboxylic acids. The crystal structures of the mimic and of four co-crystals thereof were obtained. The mimic forms hydrogen bonds in a way that closely resembles those found in the crystal structure of erlotinib. The four co-crystals display self-consistent hydrogen-bond interactions. Thermal and solubility data for the co-crystals demonstrate that by making systematic and controllable changes to the solid forms of the mimic, it is also possible to alter the behaviour and properties of the new solid forms. The use of a suitable structural mimic can allow for a systematic structural examination of a compound that is otherwise not amenable to such investigations by facilitating the elucidation and mapping out of a closely related structural landscape.

Computing details

For all structures, data collection: Bruker APEX2; cell refinement: Bruker SAINT; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick 2008). Program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014) for MP1601, MP1609, MP1611, MP1614; SHELXL2013 (Sheldrick, 2013) for MP1604. For all structures, molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.

(MP1601)

Crystal data

C18H16N3O2·Cl	Dx = 1.381 Mg m^−3
Mr = 341.79	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9849 reflections
a = 9.507 (2) Å	θ = 2.3–26.1°
b = 7.9958 (17) Å	µ = 0.25 mm^−1
c = 43.262 (9) Å	T = 130 K
V = 3288.6 (12) Å^3	Block, colourless
Z = 8	0.49 × 0.30 × 0.15 mm
F(000) = 1424

Data collection

Bruker APEX-II CCD diffractometer	3440 independent reflections
Radiation source: Fine-focus sealed tube	2741 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
φ and ω scans	θmax = 26.8°, θmin = 0.9°
Absorption correction: multi-scan SADABS	h = −11→11
Tmin = 0.89, Tmax = 0.96	k = −9→10
44653 measured reflections	l = −53→54

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: mixed
wR(F^2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0435P)^2 + 2.0184P] where P = (Fo^2 + 2Fc^2)/3
3440 reflections	(Δ/σ)max = 0.001
227 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.39 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
N1	0.61043 (16)	0.5662 (2)	0.37679 (3)	0.0204 (3)
H1	0.707 (3)	0.574 (3)	0.3806 (6)	0.050 (7)*
C2	0.56235 (18)	0.4826 (2)	0.35244 (4)	0.0220 (4)
H2	0.6295	0.4294	0.3395	0.026*
N3	0.42816 (15)	0.4677 (2)	0.34488 (3)	0.0216 (3)
C4	0.33158 (18)	0.5386 (2)	0.36391 (4)	0.0191 (4)
C5	0.27757 (18)	0.6876 (2)	0.41456 (4)	0.0191 (4)
H5	0.179	0.677	0.4116	0.023*
C6	0.32851 (18)	0.7690 (2)	0.44030 (4)	0.0189 (4)
C7	0.47767 (18)	0.7891 (2)	0.44460 (4)	0.0193 (4)
C8	0.57063 (17)	0.7212 (2)	0.42374 (4)	0.0191 (4)
H8	0.6692	0.7325	0.4267	0.023*
C9	0.51783 (18)	0.6349 (2)	0.39794 (4)	0.0184 (4)
C10	0.37196 (18)	0.6196 (2)	0.39250 (4)	0.0183 (4)
H11	0.131 (2)	0.568 (3)	0.3676 (5)	0.034 (6)*
N11	0.19569 (16)	0.5314 (2)	0.35527 (3)	0.0210 (3)
C12	0.14402 (18)	0.4718 (2)	0.32624 (4)	0.0198 (4)
C13	0.01653 (18)	0.3863 (2)	0.32640 (4)	0.0197 (4)
H13	−0.0294	0.3637	0.3455	0.024*
C14	−0.04463 (19)	0.3332 (2)	0.29848 (4)	0.0213 (4)
C15	0.0252 (2)	0.3641 (3)	0.27057 (4)	0.0257 (4)
H15	−0.0135	0.3253	0.2516	0.031*
C16	0.1514 (2)	0.4520 (3)	0.27069 (4)	0.0281 (4)
H16	0.1976	0.4744	0.2517	0.034*
C17	0.21101 (19)	0.5075 (3)	0.29817 (4)	0.0252 (4)
H17	0.2964	0.5692	0.2979	0.03*
C18	−0.1822 (2)	0.2567 (2)	0.29888 (4)	0.0237 (4)
C19	−0.2992 (2)	0.2029 (3)	0.29934 (5)	0.0293 (5)
H19	−0.3924	0.1601	0.2997	0.035*
O20	0.24816 (13)	0.83706 (17)	0.46320 (3)	0.0242 (3)
C21	0.09758 (18)	0.8180 (3)	0.46041 (4)	0.0264 (4)
H21A	0.0656	0.8705	0.4412	0.04*
H21B	0.0513	0.8718	0.478	0.04*
H21C	0.0737	0.6988	0.4601	0.04*
O22	0.51524 (13)	0.87877 (17)	0.46991 (3)	0.0245 (3)
C23	0.66261 (19)	0.9183 (3)	0.47316 (4)	0.0277 (4)
H23A	0.7163	0.8149	0.476	0.042*
H23B	0.676	0.9912	0.4911	0.042*
H23C	0.6956	0.9758	0.4545	0.042*
Cl24	0.91894 (4)	0.63367 (6)	0.39344 (2)	0.02598 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0155 (7)	0.0237 (8)	0.0221 (8)	0.0010 (7)	0.0004 (6)	−0.0015 (7)
C2	0.0212 (9)	0.0226 (9)	0.0222 (9)	0.0020 (8)	0.0018 (7)	−0.0002 (8)
N3	0.0194 (8)	0.0231 (8)	0.0225 (8)	0.0022 (7)	−0.0008 (6)	−0.0018 (7)
C4	0.0180 (8)	0.0190 (9)	0.0203 (9)	−0.0012 (7)	0.0005 (7)	0.0028 (8)
C5	0.0151 (8)	0.0214 (9)	0.0207 (8)	−0.0005 (7)	−0.0012 (7)	0.0012 (8)
C6	0.0189 (8)	0.0200 (9)	0.0179 (8)	0.0006 (8)	0.0019 (7)	0.0017 (8)
C7	0.0217 (9)	0.0193 (9)	0.0169 (8)	−0.0016 (8)	−0.0033 (7)	0.0001 (8)
C8	0.0149 (8)	0.0206 (9)	0.0218 (9)	−0.0017 (7)	−0.0027 (7)	0.0014 (8)
C9	0.0181 (8)	0.0176 (9)	0.0194 (8)	0.0006 (7)	0.0018 (7)	0.0039 (8)
C10	0.0188 (9)	0.0170 (9)	0.0190 (8)	0.0001 (7)	−0.0008 (7)	0.0018 (7)
N11	0.0163 (7)	0.0289 (9)	0.0178 (7)	−0.0004 (7)	−0.0011 (6)	−0.0026 (7)
C12	0.0199 (9)	0.0212 (9)	0.0182 (8)	0.0017 (8)	−0.0033 (7)	−0.0009 (8)
C13	0.0201 (9)	0.0208 (9)	0.0182 (8)	0.0008 (8)	−0.0002 (7)	0.0010 (8)
C14	0.0212 (9)	0.0193 (9)	0.0235 (9)	0.0012 (8)	−0.0031 (7)	−0.0013 (8)
C15	0.0252 (9)	0.0333 (11)	0.0186 (9)	0.0014 (9)	−0.0034 (7)	−0.0043 (9)
C16	0.0269 (10)	0.0365 (11)	0.0208 (9)	−0.0006 (9)	0.0030 (8)	0.0007 (9)
C17	0.0199 (9)	0.0317 (11)	0.0240 (9)	−0.0037 (8)	0.0000 (7)	0.0016 (9)
C18	0.0303 (10)	0.0214 (9)	0.0193 (9)	0.0010 (9)	−0.0046 (7)	−0.0029 (8)
C19	0.0274 (10)	0.0277 (10)	0.0328 (11)	−0.0067 (9)	−0.0035 (8)	−0.0027 (9)
O20	0.0184 (6)	0.0321 (7)	0.0221 (6)	0.0007 (6)	0.0023 (5)	−0.0066 (6)
C21	0.0178 (9)	0.0347 (11)	0.0268 (9)	0.0017 (8)	0.0036 (7)	−0.0024 (9)
O22	0.0202 (6)	0.0310 (7)	0.0224 (7)	−0.0034 (6)	−0.0022 (5)	−0.0051 (6)
C23	0.0208 (9)	0.0352 (11)	0.0271 (10)	−0.0058 (9)	−0.0036 (8)	−0.0062 (9)
Cl24	0.0149 (2)	0.0340 (3)	0.0290 (3)	−0.00064 (19)	−0.00027 (17)	−0.0003 (2)

Geometric parameters (Å, º)

N1—C2	1.329 (2)	C12—C17	1.401 (2)
N1—C9	1.384 (2)	C13—C14	1.406 (2)
N1—H1	0.94 (3)	C13—H13	0.95
C2—N3	1.322 (2)	C14—C15	1.400 (3)
C2—H2	0.95	C14—C18	1.444 (3)
N3—C4	1.357 (2)	C15—C16	1.390 (3)
C4—N11	1.346 (2)	C15—H15	0.95
C4—C10	1.448 (2)	C16—C17	1.390 (3)
C5—C6	1.378 (2)	C16—H16	0.95
C5—C10	1.418 (2)	C17—H17	0.95
C5—H5	0.95	C18—C19	1.193 (3)
C6—O20	1.364 (2)	C19—H19	0.95
C6—C7	1.439 (2)	O20—C21	1.445 (2)
C7—O22	1.356 (2)	C21—H21A	0.98
C7—C8	1.375 (2)	C21—H21B	0.98
C8—C9	1.405 (2)	C21—H21C	0.98
C8—H8	0.95	O22—C23	1.443 (2)
C9—C10	1.412 (2)	C23—H23A	0.98
N11—C12	1.430 (2)	C23—H23B	0.98
N11—H11	0.87 (2)	C23—H23C	0.98
C12—C13	1.392 (3)
C2—N1—C9	120.35 (16)	C17—C12—N11	122.50 (16)
C2—N1—H1	120.6 (15)	C12—C13—C14	120.28 (16)
C9—N1—H1	118.9 (15)	C12—C13—H13	119.9
N3—C2—N1	124.98 (17)	C14—C13—H13	119.9
N3—C2—H2	117.5	C15—C14—C13	119.42 (17)
N1—C2—H2	117.5	C15—C14—C18	120.98 (16)
C2—N3—C4	117.71 (15)	C13—C14—C18	119.49 (16)
N11—C4—N3	117.59 (16)	C16—C15—C14	119.70 (17)
N11—C4—C10	120.70 (16)	C16—C15—H15	120.2
N3—C4—C10	121.71 (16)	C14—C15—H15	120.2
C6—C5—C10	120.16 (16)	C15—C16—C17	121.11 (17)
C6—C5—H5	119.9	C15—C16—H16	119.4
C10—C5—H5	119.9	C17—C16—H16	119.4
O20—C6—C5	125.35 (16)	C16—C17—C12	119.39 (17)
O20—C6—C7	114.39 (15)	C16—C17—H17	120.3
C5—C6—C7	120.25 (15)	C12—C17—H17	120.3
O22—C7—C8	124.71 (16)	C19—C18—C14	176.1 (2)
O22—C7—C6	115.02 (15)	C18—C19—H19	180.0
C8—C7—C6	120.27 (16)	C6—O20—C21	116.87 (14)
C7—C8—C9	119.07 (16)	O20—C21—H21A	109.5
C7—C8—H8	120.5	O20—C21—H21B	109.5
C9—C8—H8	120.5	H21A—C21—H21B	109.5
N1—C9—C8	119.55 (16)	O20—C21—H21C	109.5
N1—C9—C10	118.71 (16)	H21A—C21—H21C	109.5
C8—C9—C10	121.72 (16)	H21B—C21—H21C	109.5
C9—C10—C5	118.44 (16)	C7—O22—C23	116.74 (14)
C9—C10—C4	116.19 (15)	O22—C23—H23A	109.5
C5—C10—C4	125.34 (16)	O22—C23—H23B	109.5
C4—N11—C12	125.98 (16)	H23A—C23—H23B	109.5
C4—N11—H11	120.0 (15)	O22—C23—H23C	109.5
C12—N11—H11	114.0 (15)	H23A—C23—H23C	109.5
C13—C12—C17	120.04 (16)	H23B—C23—H23C	109.5
C13—C12—N11	117.28 (15)
C9—N1—C2—N3	5.3 (3)	N11—C4—C10—C9	−173.99 (16)
N1—C2—N3—C4	−2.2 (3)	N3—C4—C10—C9	5.9 (3)
C2—N3—C4—N11	176.37 (17)	N11—C4—C10—C5	4.2 (3)
C2—N3—C4—C10	−3.5 (3)	N3—C4—C10—C5	−175.95 (17)
C10—C5—C6—O20	−179.04 (17)	N3—C4—N11—C12	−7.2 (3)
C10—C5—C6—C7	1.5 (3)	C10—C4—N11—C12	172.68 (17)
O20—C6—C7—O22	−2.8 (2)	C4—N11—C12—C13	144.60 (18)
C5—C6—C7—O22	176.68 (16)	C4—N11—C12—C17	−40.3 (3)
O20—C6—C7—C8	177.74 (16)	C17—C12—C13—C14	0.9 (3)
C5—C6—C7—C8	−2.8 (3)	N11—C12—C13—C14	176.14 (16)
O22—C7—C8—C9	−178.21 (16)	C12—C13—C14—C15	1.2 (3)
C6—C7—C8—C9	1.2 (3)	C12—C13—C14—C18	−175.01 (17)
C2—N1—C9—C8	179.27 (16)	C13—C14—C15—C16	−2.2 (3)
C2—N1—C9—C10	−2.3 (3)	C18—C14—C15—C16	173.96 (18)
C7—C8—C9—N1	179.93 (16)	C14—C15—C16—C17	1.1 (3)
C7—C8—C9—C10	1.6 (3)	C15—C16—C17—C12	1.1 (3)
N1—C9—C10—C5	178.86 (16)	C13—C12—C17—C16	−2.1 (3)
C8—C9—C10—C5	−2.8 (3)	N11—C12—C17—C16	−177.07 (18)
N1—C9—C10—C4	−2.8 (2)	C5—C6—O20—C21	1.6 (3)
C8—C9—C10—C4	175.50 (16)	C7—C6—O20—C21	−178.90 (16)
C6—C5—C10—C9	1.2 (3)	C8—C7—O22—C23	6.3 (3)
C6—C5—C10—C4	−176.94 (17)	C6—C7—O22—C23	−173.08 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl24	0.94 (3)	2.14 (3)	3.0681 (17)	169 (2)
N11—H11···Cl24^i	0.87 (2)	2.36 (2)	3.2121 (17)	167 (2)

Symmetry code: (i) x−1, y, z.

(MP1604)

Crystal data

2(C18H16N3O2)·C6H8O4·C6H10O4·CH4O	Z = 2
Mr = 934.98	F(000) = 988
Triclinic, P1	Dx = 1.393 Mg m^−3
a = 9.304 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 15.756 (8) Å	Cell parameters from 3033 reflections
c = 15.829 (7) Å	θ = 2.3–24.9°
α = 94.54 (2)°	µ = 0.10 mm^−1
β = 93.95 (2)°	T = 130 K
γ = 104.56 (2)°	Blocks, colourless
V = 2229.4 (18) Å^3	0.44 × 0.30 × 0.17 mm

Data collection

Bruker APEX-II CCD diffractometer	8806 independent reflections
Radiation source: Fine-focus sealed tube	4654 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.115
φ and ω scans	θmax = 26.6°, θmin = 1.3°
Absorption correction: multi-scan SADABS	h = −11→11
Tmin = 0.96, Tmax = 0.98	k = −19→19
35562 measured reflections	l = −19→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.065	Hydrogen site location: mixed
wR(F^2) = 0.198	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0887P)^2] where P = (Fo^2 + 2Fc^2)/3
8806 reflections	(Δ/σ)max = 0.001
646 parameters	Δρmax = 0.48 e Å^−3
5 restraints	Δρmin = −0.38 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
N1	0.6662 (3)	0.18681 (18)	0.77454 (17)	0.0233 (7)
H1	0.681 (5)	0.193 (3)	0.715 (2)	0.057 (13)*
C2	0.5454 (4)	0.1311 (2)	0.7921 (2)	0.0252 (8)
H2	0.4819	0.0967	0.7455	0.03*
N3	0.5035 (3)	0.11826 (18)	0.86899 (17)	0.0243 (7)
C4	0.5897 (4)	0.1676 (2)	0.9349 (2)	0.0210 (8)
C5	0.8181 (4)	0.2863 (2)	0.9882 (2)	0.0226 (8)
H5	0.7956	0.2825	1.0457	0.027*
C6	0.9428 (4)	0.3442 (2)	0.9699 (2)	0.0219 (8)
C7	0.9787 (4)	0.3497 (2)	0.8842 (2)	0.0205 (8)
C8	0.8884 (4)	0.2977 (2)	0.8198 (2)	0.0227 (8)
H8	0.9126	0.301	0.7626	0.027*
C9	0.7594 (4)	0.2393 (2)	0.83913 (19)	0.0198 (8)
C10	0.7218 (4)	0.2315 (2)	0.92261 (19)	0.0204 (8)
H11	0.607 (4)	0.193 (3)	1.058 (2)	0.044 (12)*
N11	0.5492 (3)	0.15582 (19)	1.01379 (18)	0.0245 (7)
C12	0.4287 (4)	0.0953 (2)	1.0418 (2)	0.0232 (8)
C13	0.4316 (4)	0.0930 (2)	1.1295 (2)	0.0245 (8)
H13	0.5123	0.1309	1.1652	0.029*
C14	0.3195 (4)	0.0365 (2)	1.1658 (2)	0.0293 (9)
C15	0.2024 (4)	−0.0179 (2)	1.1132 (2)	0.0336 (9)
H15	0.1231	−0.0568	1.1366	0.04*
C16	0.2021 (5)	−0.0150 (2)	1.0272 (2)	0.0380 (10)
H16	0.1216	−0.0527	0.9912	0.046*
C17	0.3136 (4)	0.0402 (2)	0.9912 (2)	0.0341 (9)
H17	0.3108	0.0402	0.931	0.041*
C18	0.3309 (4)	0.0337 (2)	1.2559 (2)	0.0354 (10)
C19	0.3483 (5)	0.0289 (3)	1.3293 (3)	0.0509 (12)
H19	0.3624	0.025	1.3888	0.061*
O20	1.0398 (3)	0.40036 (15)	1.02769 (13)	0.0277 (6)
C21	0.9977 (4)	0.4064 (2)	1.1127 (2)	0.0280 (9)
H21A	0.902	0.4217	1.1125	0.042*
H21B	1.0741	0.4519	1.1482	0.042*
H21C	0.9882	0.3495	1.1359	0.042*
O22	1.1057 (3)	0.40882 (15)	0.87362 (13)	0.0254 (6)
C23	1.1396 (4)	0.4219 (2)	0.7875 (2)	0.0281 (9)
H23A	1.1443	0.3659	0.7577	0.042*
H23B	1.2359	0.4653	0.788	0.042*
H23C	1.0615	0.4435	0.7583	0.042*
H24	0.568 (5)	0.402 (3)	1.073 (2)	0.066 (14)*
N24	0.5623 (3)	0.40509 (19)	1.01208 (18)	0.0260 (7)
C25	0.6648 (4)	0.4553 (2)	0.9720 (2)	0.0265 (8)
H25	0.7459	0.4951	1.0059	0.032*
N26	0.6648 (3)	0.45541 (18)	0.88867 (17)	0.0254 (7)
C27	0.5539 (4)	0.3985 (2)	0.8411 (2)	0.0229 (8)
C28	0.3248 (4)	0.2740 (2)	0.8317 (2)	0.0242 (8)
H28	0.3203	0.2664	0.7713	0.029*
C29	0.2198 (4)	0.2218 (2)	0.8727 (2)	0.0225 (8)
C30	0.2230 (4)	0.2338 (2)	0.9627 (2)	0.0231 (8)
C31	0.3362 (4)	0.2940 (2)	1.0082 (2)	0.0246 (8)
H31	0.3411	0.3005	1.0686	0.03*
C32	0.4453 (4)	0.3460 (2)	0.9661 (2)	0.0219 (8)
C33	0.4396 (4)	0.3389 (2)	0.8773 (2)	0.0223 (8)
H34	0.485 (4)	0.360 (2)	0.724 (2)	0.028 (10)*
N34	0.5571 (3)	0.39817 (19)	0.75652 (18)	0.0249 (7)
C35	0.6682 (4)	0.4573 (2)	0.7176 (2)	0.0242 (8)
C36	0.6774 (4)	0.5464 (2)	0.7279 (2)	0.0261 (8)
H36	0.6111	0.5683	0.7613	0.031*
C37	0.7850 (4)	0.6032 (2)	0.6886 (2)	0.0280 (9)
C38	0.8813 (4)	0.5702 (2)	0.6406 (2)	0.0313 (9)
H38	0.9562	0.6095	0.6145	0.038*
C39	0.8697 (4)	0.4824 (2)	0.6304 (2)	0.0310 (9)
H39	0.9358	0.4603	0.5969	0.037*
C40	0.7618 (4)	0.4252 (2)	0.6686 (2)	0.0277 (9)
H40	0.7526	0.3636	0.661	0.033*
C41	0.7927 (5)	0.6952 (3)	0.6962 (2)	0.0396 (11)
C42	0.7942 (6)	0.7694 (3)	0.7012 (3)	0.0616 (15)
H42	0.7954	0.8301	0.7052	0.074*
O43	0.1059 (3)	0.15688 (15)	0.83480 (14)	0.0278 (6)
C44	0.0984 (4)	0.1412 (2)	0.7442 (2)	0.0324 (9)
H44A	0.0925	0.195	0.7186	0.049*
H44B	0.0097	0.0937	0.7237	0.049*
H44C	0.1879	0.1242	0.7281	0.049*
O45	0.1087 (3)	0.18256 (15)	0.99632 (14)	0.0297 (6)
C46	0.1123 (4)	0.1918 (2)	1.0869 (2)	0.0334 (9)
H46A	0.193	0.1691	1.1115	0.05*
H46B	0.0169	0.1585	1.1042	0.05*
H46C	0.1294	0.2542	1.1074	0.05*
O47	0.9328 (3)	0.26142 (16)	0.60987 (14)	0.0298 (6)
O48	0.6959 (3)	0.19518 (16)	0.60562 (14)	0.0307 (6)
C49	0.8127 (4)	0.2235 (2)	0.5699 (2)	0.0241 (8)
C50	0.8003 (4)	0.2123 (2)	0.47383 (19)	0.0256 (8)
H50A	0.7339	0.1536	0.4531	0.031*
H50B	0.8999	0.2151	0.4542	0.031*
C51	0.7384 (4)	0.2837 (2)	0.4365 (2)	0.0270 (9)
H51A	0.6403	0.282	0.4579	0.032*
H51B	0.8064	0.3421	0.4563	0.032*
C52	0.7203 (4)	0.2727 (2)	0.34023 (19)	0.0265 (8)
H52A	0.8182	0.2735	0.3189	0.032*
H52B	0.6513	0.2145	0.3206	0.032*
C53	0.6612 (4)	0.3433 (2)	0.3027 (2)	0.0312 (9)
H53A	0.7299	0.4012	0.3235	0.037*
H53B	0.5635	0.342	0.3244	0.037*
C54	0.6418 (4)	0.3363 (2)	0.2067 (2)	0.0241 (8)
O55	0.5912 (3)	0.39546 (16)	0.17526 (14)	0.0295 (6)
O56	0.6743 (3)	0.27537 (15)	0.16538 (14)	0.0310 (6)
H57	0.916 (5)	0.696 (3)	0.439 (3)	0.09 (2)*
O57	0.8451 (3)	0.66976 (18)	0.46871 (16)	0.0376 (7)
O58	0.6968 (3)	0.68517 (17)	0.36078 (15)	0.0359 (7)
C59	0.7146 (4)	0.6617 (2)	0.4309 (2)	0.0263 (8)
C60	0.5907 (4)	0.6203 (2)	0.4806 (2)	0.0258 (8)
H60A	0.4981	0.6342	0.4582	0.031*
H60B	0.6136	0.6457	0.5407	0.031*
C61	0.5654 (4)	0.5210 (2)	0.4765 (2)	0.0247 (8)
H61A	0.5474	0.4959	0.4162	0.03*
H61B	0.6563	0.5072	0.5015	0.03*
H62	0.479 (4)	0.833 (3)	0.445 (3)	0.077 (17)*
O62	0.5681 (3)	0.83802 (19)	0.47393 (17)	0.0425 (7)
O63	0.6431 (3)	0.9375 (2)	0.3863 (2)	0.0609 (10)
C64	0.6705 (4)	0.8968 (2)	0.4431 (2)	0.0317 (9)
C65	0.8222 (4)	0.9052 (2)	0.4820 (2)	0.0304 (9)
H65A	0.8664	0.8628	0.4503	0.037*
H65B	0.8168	0.8897	0.5413	0.037*
C66	0.9216 (4)	0.9964 (2)	0.4823 (2)	0.0325 (9)
H66A	0.8804	1.0384	0.5166	0.039*
H66B	0.9228	1.0132	0.4233	0.039*
C67	0.8009 (6)	0.0793 (3)	0.2371 (3)	0.0607 (14)
H67A	0.8625	0.1104	0.2884	0.091*
H67B	0.8379	0.029	0.2171	0.091*
H67C	0.6973	0.0583	0.2502	0.091*
H68	0.768 (9)	0.180 (4)	0.192 (5)	0.22 (4)*
O68	0.8081 (4)	0.1374 (2)	0.17298 (18)	0.0526 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0260 (19)	0.0235 (16)	0.0186 (15)	0.0027 (14)	0.0029 (13)	0.0018 (12)
C2	0.026 (2)	0.0267 (19)	0.0210 (18)	0.0036 (17)	0.0006 (16)	−0.0004 (15)
N3	0.0247 (19)	0.0251 (16)	0.0215 (15)	0.0035 (14)	0.0013 (13)	0.0033 (12)
C4	0.021 (2)	0.0205 (18)	0.0211 (18)	0.0035 (16)	0.0045 (15)	0.0034 (14)
C5	0.026 (2)	0.0228 (18)	0.0189 (17)	0.0054 (17)	0.0061 (15)	0.0021 (14)
C6	0.024 (2)	0.0215 (18)	0.0184 (17)	0.0042 (16)	0.0003 (15)	0.0015 (14)
C7	0.019 (2)	0.0176 (17)	0.0234 (18)	−0.0003 (16)	0.0061 (15)	0.0053 (14)
C8	0.030 (2)	0.0208 (18)	0.0179 (17)	0.0064 (16)	0.0047 (15)	0.0050 (14)
C9	0.022 (2)	0.0170 (17)	0.0190 (17)	0.0024 (15)	0.0024 (15)	0.0017 (13)
C10	0.022 (2)	0.0189 (17)	0.0193 (17)	0.0039 (16)	0.0037 (15)	0.0020 (13)
N11	0.025 (2)	0.0249 (16)	0.0205 (15)	0.0011 (14)	0.0022 (14)	0.0044 (13)
C12	0.021 (2)	0.0211 (18)	0.0262 (18)	0.0011 (16)	0.0070 (16)	0.0037 (14)
C13	0.022 (2)	0.0256 (19)	0.0267 (19)	0.0052 (16)	0.0067 (16)	0.0052 (15)
C14	0.035 (3)	0.029 (2)	0.027 (2)	0.0095 (19)	0.0148 (17)	0.0099 (16)
C15	0.029 (3)	0.028 (2)	0.040 (2)	−0.0013 (18)	0.0125 (19)	0.0041 (17)
C16	0.034 (3)	0.034 (2)	0.036 (2)	−0.009 (2)	0.0082 (19)	−0.0026 (17)
C17	0.029 (3)	0.039 (2)	0.028 (2)	−0.0021 (19)	0.0035 (18)	0.0031 (17)
C18	0.037 (3)	0.033 (2)	0.036 (2)	0.0061 (19)	0.0116 (19)	0.0075 (17)
C19	0.062 (3)	0.058 (3)	0.036 (2)	0.017 (3)	0.013 (2)	0.011 (2)
O20	0.0254 (16)	0.0333 (14)	0.0173 (12)	−0.0036 (12)	0.0011 (11)	−0.0023 (10)
C21	0.030 (2)	0.031 (2)	0.0194 (18)	0.0015 (18)	0.0032 (16)	−0.0029 (15)
O22	0.0267 (16)	0.0275 (13)	0.0197 (12)	0.0008 (12)	0.0070 (11)	0.0048 (10)
C23	0.029 (2)	0.033 (2)	0.0214 (18)	0.0046 (18)	0.0090 (16)	0.0078 (15)
N24	0.028 (2)	0.0273 (17)	0.0212 (16)	0.0045 (15)	0.0009 (14)	0.0053 (13)
C25	0.025 (2)	0.0251 (19)	0.0263 (19)	0.0015 (17)	−0.0006 (16)	0.0043 (15)
N26	0.0237 (19)	0.0274 (16)	0.0215 (15)	0.0000 (14)	−0.0016 (13)	0.0048 (12)
C27	0.024 (2)	0.0244 (18)	0.0204 (17)	0.0047 (17)	0.0019 (15)	0.0059 (14)
C28	0.024 (2)	0.0258 (19)	0.0223 (18)	0.0049 (17)	0.0018 (16)	0.0048 (15)
C29	0.019 (2)	0.0213 (18)	0.0258 (18)	0.0017 (16)	0.0019 (15)	0.0064 (14)
C30	0.020 (2)	0.0257 (19)	0.0246 (18)	0.0037 (16)	0.0076 (16)	0.0105 (15)
C31	0.025 (2)	0.030 (2)	0.0192 (17)	0.0071 (17)	0.0029 (16)	0.0067 (15)
C32	0.023 (2)	0.0216 (18)	0.0208 (17)	0.0057 (16)	−0.0006 (15)	0.0048 (14)
C33	0.022 (2)	0.0213 (18)	0.0235 (18)	0.0048 (16)	0.0017 (15)	0.0067 (14)
N34	0.0205 (19)	0.0272 (17)	0.0212 (16)	−0.0054 (14)	0.0019 (14)	0.0046 (13)
C35	0.024 (2)	0.0270 (19)	0.0183 (17)	0.0014 (17)	−0.0006 (15)	0.0038 (14)
C36	0.026 (2)	0.030 (2)	0.0192 (17)	0.0016 (17)	0.0011 (15)	0.0043 (15)
C37	0.030 (2)	0.027 (2)	0.0227 (18)	0.0021 (18)	−0.0043 (17)	0.0028 (15)
C38	0.026 (2)	0.038 (2)	0.0241 (19)	−0.0044 (18)	−0.0002 (17)	0.0119 (16)
C39	0.024 (2)	0.041 (2)	0.0268 (19)	0.0031 (18)	0.0041 (16)	0.0117 (17)
C40	0.028 (2)	0.030 (2)	0.0252 (18)	0.0056 (18)	0.0032 (16)	0.0064 (15)
C41	0.053 (3)	0.034 (2)	0.025 (2)	−0.002 (2)	0.0018 (19)	0.0046 (17)
C42	0.110 (5)	0.034 (3)	0.039 (3)	0.014 (3)	0.006 (3)	0.006 (2)
O43	0.0275 (16)	0.0280 (14)	0.0224 (12)	−0.0041 (12)	0.0038 (11)	0.0045 (10)
C44	0.037 (3)	0.031 (2)	0.0229 (19)	−0.0014 (19)	0.0018 (17)	0.0010 (15)
O45	0.0292 (16)	0.0337 (14)	0.0237 (13)	0.0002 (12)	0.0069 (11)	0.0097 (11)
C46	0.035 (3)	0.041 (2)	0.0226 (19)	0.0009 (19)	0.0123 (17)	0.0097 (16)
O47	0.0238 (16)	0.0389 (15)	0.0216 (13)	−0.0021 (12)	−0.0002 (11)	0.0086 (11)
O48	0.0214 (16)	0.0444 (16)	0.0207 (13)	−0.0034 (12)	0.0040 (11)	0.0076 (11)
C49	0.026 (2)	0.0245 (19)	0.0190 (18)	0.0006 (17)	0.0010 (17)	0.0044 (14)
C50	0.029 (2)	0.029 (2)	0.0178 (17)	0.0064 (17)	0.0015 (15)	0.0028 (14)
C51	0.032 (2)	0.029 (2)	0.0197 (18)	0.0061 (17)	0.0042 (16)	0.0019 (14)
C52	0.031 (2)	0.031 (2)	0.0181 (17)	0.0080 (17)	0.0042 (16)	0.0016 (14)
C53	0.041 (3)	0.034 (2)	0.0191 (18)	0.0103 (19)	0.0035 (17)	0.0031 (15)
C54	0.024 (2)	0.027 (2)	0.0162 (17)	−0.0043 (17)	0.0024 (15)	0.0029 (15)
O55	0.0338 (17)	0.0350 (14)	0.0199 (12)	0.0081 (13)	0.0018 (11)	0.0074 (10)
O56	0.0404 (18)	0.0290 (14)	0.0212 (13)	0.0045 (13)	0.0043 (12)	0.0015 (11)
O57	0.0248 (18)	0.0530 (18)	0.0310 (15)	−0.0019 (14)	0.0027 (13)	0.0181 (13)
O58	0.0298 (17)	0.0485 (17)	0.0236 (14)	−0.0026 (13)	0.0008 (11)	0.0113 (12)
C59	0.025 (2)	0.0269 (19)	0.0227 (19)	0.0005 (17)	−0.0014 (16)	0.0017 (15)
C60	0.025 (2)	0.029 (2)	0.0213 (18)	−0.0003 (17)	0.0045 (16)	0.0058 (15)
C61	0.021 (2)	0.0270 (19)	0.0234 (18)	−0.0010 (16)	0.0026 (15)	0.0075 (14)
O62	0.0279 (19)	0.0521 (18)	0.0410 (16)	−0.0042 (15)	−0.0016 (14)	0.0169 (13)
O63	0.033 (2)	0.074 (2)	0.066 (2)	−0.0120 (16)	−0.0105 (16)	0.0406 (18)
C64	0.029 (3)	0.031 (2)	0.029 (2)	−0.0043 (19)	0.0041 (18)	0.0055 (17)
C65	0.026 (2)	0.033 (2)	0.028 (2)	0.0015 (18)	−0.0004 (17)	0.0037 (16)
C66	0.029 (2)	0.031 (2)	0.034 (2)	0.0025 (19)	0.0005 (18)	0.0054 (17)
C67	0.085 (4)	0.049 (3)	0.051 (3)	0.025 (3)	−0.004 (3)	0.008 (2)
O68	0.055 (2)	0.064 (2)	0.0421 (17)	0.0155 (18)	0.0166 (15)	0.0096 (15)

Geometric parameters (Å, º)

N1—C2	1.303 (4)	C35—C36	1.380 (5)
N1—C9	1.365 (4)	C36—C37	1.383 (5)
N1—H1	0.97 (3)	C36—H36	0.95
C2—N3	1.318 (4)	C37—C38	1.384 (5)
C2—H2	0.95	C37—C41	1.428 (5)
N3—C4	1.333 (4)	C38—C39	1.357 (5)
C4—N11	1.342 (4)	C38—H38	0.95
C4—C10	1.416 (5)	C39—C40	1.380 (5)
C5—C6	1.349 (5)	C39—H39	0.95
C5—C10	1.403 (5)	C40—H40	0.95
C5—H5	0.95	C41—C42	1.162 (6)
C6—O20	1.338 (4)	C42—H42	0.95
C6—C7	1.423 (4)	O43—C44	1.430 (4)
C7—O22	1.339 (4)	C44—H44A	0.98
C7—C8	1.350 (5)	C44—H44B	0.98
C8—C9	1.386 (5)	C44—H44C	0.98
C8—H8	0.95	O45—C46	1.428 (4)
C9—C10	1.397 (4)	C46—H46A	0.98
N11—C12	1.400 (4)	C46—H46B	0.98
N11—H11	0.92 (4)	C46—H46C	0.98
C12—C17	1.359 (5)	O47—C49	1.231 (4)
C12—C13	1.390 (4)	O48—C49	1.257 (4)
C13—C14	1.381 (5)	C49—C50	1.510 (4)
C13—H13	0.95	C50—C51	1.527 (5)
C14—C15	1.381 (5)	C50—H50A	0.99
C14—C18	1.427 (5)	C50—H50B	0.99
C15—C16	1.366 (5)	C51—C52	1.513 (4)
C15—H15	0.95	C51—H51A	0.99
C16—C17	1.366 (5)	C51—H51B	0.99
C16—H16	0.95	C52—C53	1.503 (5)
C17—H17	0.95	C52—H52A	0.99
C18—C19	1.174 (5)	C52—H52B	0.99
C19—H19	0.95	C53—C54	1.511 (4)
O20—C21	1.431 (4)	C53—H53A	0.99
C21—H21A	0.98	C53—H53B	0.99
C21—H21B	0.98	C54—O56	1.231 (4)
C21—H21C	0.98	C54—O55	1.265 (4)
O22—C23	1.439 (4)	O57—C59	1.288 (4)
C23—H23A	0.98	O57—H57	0.87 (3)
C23—H23B	0.98	O58—C59	1.211 (4)
C23—H23C	0.98	C59—C60	1.483 (5)
N24—C25	1.312 (4)	C60—C61	1.517 (5)
N24—C32	1.362 (4)	C60—H60A	0.99
N24—H24	0.97 (3)	C60—H60B	0.99
C25—N26	1.320 (4)	C61—C61^i	1.508 (6)
C25—H25	0.95	C61—H61A	0.99
N26—C27	1.325 (4)	C61—H61B	0.99
C27—N34	1.342 (4)	O62—C64	1.302 (4)
C27—C33	1.417 (5)	O62—H62	0.90 (3)
C28—C29	1.348 (5)	O63—C64	1.195 (4)
C28—C33	1.391 (5)	C64—C65	1.470 (5)
C28—H28	0.95	C65—C66	1.500 (5)
C29—O43	1.341 (4)	C65—H65A	0.99
C29—C30	1.421 (4)	C65—H65B	0.99
C30—O45	1.334 (4)	C66—C66^ii	1.500 (7)
C30—C31	1.346 (5)	C66—H66A	0.99
C31—C32	1.382 (5)	C66—H66B	0.99
C31—H31	0.95	C67—O68	1.413 (5)
C32—C33	1.397 (4)	C67—H67A	0.98
N34—C35	1.419 (4)	C67—H67B	0.98
N34—H34	0.88 (4)	C67—H67C	0.98
C35—C40	1.367 (5)	O68—H68	0.88 (3)
C2—N1—C9	119.5 (3)	C35—C36—H36	120.6
C2—N1—H1	118 (2)	C37—C36—H36	120.6
C9—N1—H1	122 (3)	C38—C37—C36	119.8 (3)
N1—C2—N3	125.7 (3)	C38—C37—C41	120.7 (4)
N1—C2—H2	117.2	C36—C37—C41	119.5 (4)
N3—C2—H2	117.2	C39—C38—C37	120.7 (4)
C2—N3—C4	117.8 (3)	C39—C38—H38	119.7
N3—C4—N11	118.9 (3)	C37—C38—H38	119.7
N3—C4—C10	121.0 (3)	C38—C39—C40	119.9 (4)
N11—C4—C10	120.1 (3)	C38—C39—H39	120.1
C6—C5—C10	120.1 (3)	C40—C39—H39	120.1
C6—C5—H5	120.0	C35—C40—C39	119.8 (3)
C10—C5—H5	120.0	C35—C40—H40	120.1
O20—C6—C5	124.5 (3)	C39—C40—H40	120.1
O20—C6—C7	115.0 (3)	C42—C41—C37	177.7 (5)
C5—C6—C7	120.5 (3)	C41—C42—H42	180.0
O22—C7—C8	123.9 (3)	C29—O43—C44	116.9 (3)
O22—C7—C6	115.3 (3)	O43—C44—H44A	109.5
C8—C7—C6	120.8 (3)	O43—C44—H44B	109.5
C7—C8—C9	118.3 (3)	H44A—C44—H44B	109.5
C7—C8—H8	120.9	O43—C44—H44C	109.5
C9—C8—H8	120.9	H44A—C44—H44C	109.5
N1—C9—C8	119.0 (3)	H44B—C44—H44C	109.5
N1—C9—C10	118.7 (3)	C30—O45—C46	116.3 (3)
C8—C9—C10	122.3 (3)	O45—C46—H46A	109.5
C9—C10—C5	118.0 (3)	O45—C46—H46B	109.5
C9—C10—C4	117.3 (3)	H46A—C46—H46B	109.5
C5—C10—C4	124.7 (3)	O45—C46—H46C	109.5
C4—N11—C12	130.4 (3)	H46A—C46—H46C	109.5
C4—N11—H11	118 (2)	H46B—C46—H46C	109.5
C12—N11—H11	112 (2)	O47—C49—O48	122.6 (3)
C17—C12—C13	119.1 (3)	O47—C49—C50	120.0 (3)
C17—C12—N11	125.7 (3)	O48—C49—C50	117.4 (3)
C13—C12—N11	115.2 (3)	C49—C50—C51	111.2 (3)
C14—C13—C12	121.3 (3)	C49—C50—H50A	109.4
C14—C13—H13	119.4	C51—C50—H50A	109.4
C12—C13—H13	119.4	C49—C50—H50B	109.4
C13—C14—C15	118.7 (3)	C51—C50—H50B	109.4
C13—C14—C18	119.2 (4)	H50A—C50—H50B	108.0
C15—C14—C18	122.1 (3)	C52—C51—C50	112.5 (3)
C16—C15—C14	119.2 (4)	C52—C51—H51A	109.1
C16—C15—H15	120.4	C50—C51—H51A	109.1
C14—C15—H15	120.4	C52—C51—H51B	109.1
C15—C16—C17	122.2 (4)	C50—C51—H51B	109.1
C15—C16—H16	118.9	H51A—C51—H51B	107.8
C17—C16—H16	118.9	C53—C52—C51	113.0 (3)
C12—C17—C16	119.6 (4)	C53—C52—H52A	109.0
C12—C17—H17	120.2	C51—C52—H52A	109.0
C16—C17—H17	120.2	C53—C52—H52B	109.0
C19—C18—C14	175.4 (5)	C51—C52—H52B	109.0
C18—C19—H19	180.0	H52A—C52—H52B	107.8
C6—O20—C21	117.0 (3)	C52—C53—C54	115.5 (3)
O20—C21—H21A	109.5	C52—C53—H53A	108.4
O20—C21—H21B	109.5	C54—C53—H53A	108.4
H21A—C21—H21B	109.5	C52—C53—H53B	108.4
O20—C21—H21C	109.5	C54—C53—H53B	108.4
H21A—C21—H21C	109.5	H53A—C53—H53B	107.5
H21B—C21—H21C	109.5	O56—C54—O55	125.2 (3)
C7—O22—C23	117.0 (3)	O56—C54—C53	119.4 (3)
O22—C23—H23A	109.5	O55—C54—C53	115.4 (3)
O22—C23—H23B	109.5	C59—O57—H57	112 (3)
H23A—C23—H23B	109.5	O58—C59—O57	122.2 (3)
O22—C23—H23C	109.5	O58—C59—C60	123.9 (3)
H23A—C23—H23C	109.5	O57—C59—C60	113.8 (3)
H23B—C23—H23C	109.5	C59—C60—C61	112.2 (3)
C25—N24—C32	119.3 (3)	C59—C60—H60A	109.2
C25—N24—H24	124 (3)	C61—C60—H60A	109.2
C32—N24—H24	116 (3)	C59—C60—H60B	109.2
N24—C25—N26	125.6 (3)	C61—C60—H60B	109.2
N24—C25—H25	117.2	H60A—C60—H60B	107.9
N26—C25—H25	117.2	C61^i—C61—C60	111.9 (4)
C25—N26—C27	117.4 (3)	C61^i—C61—H61A	109.2
N26—C27—N34	116.7 (3)	C60—C61—H61A	109.2
N26—C27—C33	122.0 (3)	C61^i—C61—H61B	109.2
N34—C27—C33	121.3 (3)	C60—C61—H61B	109.2
C29—C28—C33	120.4 (3)	H61A—C61—H61B	107.9
C29—C28—H28	119.8	C64—O62—H62	110 (3)
C33—C28—H28	119.8	O63—C64—O62	122.5 (4)
O43—C29—C28	125.0 (3)	O63—C64—C65	123.6 (4)
O43—C29—C30	114.5 (3)	O62—C64—C65	113.8 (3)
C28—C29—C30	120.4 (3)	C64—C65—C66	112.6 (3)
O45—C30—C31	124.4 (3)	C64—C65—H65A	109.1
O45—C30—C29	115.5 (3)	C66—C65—H65A	109.1
C31—C30—C29	120.0 (3)	C64—C65—H65B	109.1
C30—C31—C32	119.2 (3)	C66—C65—H65B	109.1
C30—C31—H31	120.4	H65A—C65—H65B	107.8
C32—C31—H31	120.4	C65—C66—C66^ii	112.5 (4)
N24—C32—C31	119.3 (3)	C65—C66—H66A	109.1
N24—C32—C33	119.1 (3)	C66^ii—C66—H66A	109.1
C31—C32—C33	121.6 (3)	C65—C66—H66B	109.1
C28—C33—C32	118.2 (3)	C66^ii—C66—H66B	109.1
C28—C33—C27	125.3 (3)	H66A—C66—H66B	107.8
C32—C33—C27	116.6 (3)	O68—C67—H67A	109.5
C27—N34—C35	123.2 (3)	O68—C67—H67B	109.5
C27—N34—H34	118 (2)	H67A—C67—H67B	109.5
C35—N34—H34	119 (2)	O68—C67—H67C	109.5
C40—C35—C36	121.0 (3)	H67A—C67—H67C	109.5
C40—C35—N34	119.6 (3)	H67B—C67—H67C	109.5
C36—C35—N34	119.3 (3)	C67—O68—H68	107 (6)
C35—C36—C37	118.7 (3)
C9—N1—C2—N3	−1.6 (5)	C28—C29—C30—O45	175.9 (3)
N1—C2—N3—C4	1.6 (5)	O43—C29—C30—C31	176.6 (3)
C2—N3—C4—N11	179.9 (3)	C28—C29—C30—C31	−4.1 (5)
C2—N3—C4—C10	−0.1 (5)	O45—C30—C31—C32	−177.3 (3)
C10—C5—C6—O20	178.6 (3)	C29—C30—C31—C32	2.7 (5)
C10—C5—C6—C7	−0.8 (5)	C25—N24—C32—C31	−179.1 (3)
O20—C6—C7—O22	1.3 (4)	C25—N24—C32—C33	1.7 (5)
C5—C6—C7—O22	−179.3 (3)	C30—C31—C32—N24	−178.1 (3)
O20—C6—C7—C8	−178.8 (3)	C30—C31—C32—C33	1.1 (5)
C5—C6—C7—C8	0.6 (5)	C29—C28—C33—C32	2.2 (5)
O22—C7—C8—C9	−179.7 (3)	C29—C28—C33—C27	−178.6 (3)
C6—C7—C8—C9	0.4 (5)	N24—C32—C33—C28	175.6 (3)
C2—N1—C9—C8	179.3 (3)	C31—C32—C33—C28	−3.6 (5)
C2—N1—C9—C10	0.0 (5)	N24—C32—C33—C27	−3.6 (5)
C7—C8—C9—N1	179.4 (3)	C31—C32—C33—C27	177.2 (3)
C7—C8—C9—C10	−1.3 (5)	N26—C27—C33—C28	−176.1 (3)
N1—C9—C10—C5	−179.6 (3)	N34—C27—C33—C28	2.1 (5)
C8—C9—C10—C5	1.1 (5)	N26—C27—C33—C32	3.1 (5)
N1—C9—C10—C4	1.3 (5)	N34—C27—C33—C32	−178.8 (3)
C8—C9—C10—C4	−178.0 (3)	N26—C27—N34—C35	−2.6 (5)
C6—C5—C10—C9	0.0 (5)	C33—C27—N34—C35	179.2 (3)
C6—C5—C10—C4	178.9 (3)	C27—N34—C35—C40	116.9 (4)
N3—C4—C10—C9	−1.3 (5)	C27—N34—C35—C36	−64.9 (5)
N11—C4—C10—C9	178.7 (3)	C40—C35—C36—C37	−0.9 (5)
N3—C4—C10—C5	179.7 (3)	N34—C35—C36—C37	−179.1 (3)
N11—C4—C10—C5	−0.2 (5)	C35—C36—C37—C38	−0.4 (5)
N3—C4—N11—C12	3.0 (5)	C35—C36—C37—C41	177.9 (3)
C10—C4—N11—C12	−177.1 (3)	C36—C37—C38—C39	1.1 (5)
C4—N11—C12—C17	−8.5 (6)	C41—C37—C38—C39	−177.2 (3)
C4—N11—C12—C13	171.2 (3)	C37—C38—C39—C40	−0.5 (5)
C17—C12—C13—C14	−0.5 (5)	C36—C35—C40—C39	1.5 (5)
N11—C12—C13—C14	179.7 (3)	N34—C35—C40—C39	179.7 (3)
C12—C13—C14—C15	−0.4 (5)	C38—C39—C40—C35	−0.8 (5)
C12—C13—C14—C18	177.2 (3)	C28—C29—O43—C44	1.4 (5)
C13—C14—C15—C16	0.8 (6)	C30—C29—O43—C44	−179.2 (3)
C18—C14—C15—C16	−176.7 (4)	C31—C30—O45—C46	−1.9 (5)
C14—C15—C16—C17	−0.3 (6)	C29—C30—O45—C46	178.2 (3)
C13—C12—C17—C16	1.1 (6)	O47—C49—C50—C51	−97.3 (4)
N11—C12—C17—C16	−179.2 (3)	O48—C49—C50—C51	80.6 (4)
C15—C16—C17—C12	−0.7 (6)	C49—C50—C51—C52	−178.3 (3)
C5—C6—O20—C21	−8.2 (5)	C50—C51—C52—C53	−179.3 (3)
C7—C6—O20—C21	171.2 (3)	C51—C52—C53—C54	179.5 (3)
C8—C7—O22—C23	5.4 (5)	C52—C53—C54—O56	−0.1 (5)
C6—C7—O22—C23	−174.7 (3)	C52—C53—C54—O55	179.6 (3)
C32—N24—C25—N26	1.2 (5)	O58—C59—C60—C61	101.4 (4)
N24—C25—N26—C27	−1.8 (5)	O57—C59—C60—C61	−77.9 (4)
C25—N26—C27—N34	−178.7 (3)	C59—C60—C61—C61^i	−177.2 (4)
C25—N26—C27—C33	−0.5 (5)	O63—C64—C65—C66	32.3 (5)
C33—C28—C29—O43	−179.2 (3)	O62—C64—C65—C66	−150.3 (3)
C33—C28—C29—C30	1.5 (5)	C64—C65—C66—C66^ii	−177.0 (4)
O43—C29—C30—O45	−3.5 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O48	0.97 (3)	1.75 (3)	2.717 (4)	175 (4)
N11—H11···O56^iii	0.92 (4)	2.01 (4)	2.908 (4)	164 (3)
N24—H24···O55^iii	0.97 (3)	1.63 (3)	2.599 (4)	175 (4)
N34—H34···O58^i	0.88 (4)	2.02 (4)	2.863 (4)	159 (3)
O57—H57···O47^iv	0.87 (3)	1.67 (3)	2.536 (4)	171 (5)
O62—H62···O48^i	0.90 (3)	1.70 (3)	2.592 (4)	170 (5)
O68—H68···O56	0.88 (3)	1.98 (5)	2.770 (4)	148 (8)

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

(MP1609)

Crystal data

C18H15N3O2·0.5(C4H6O4)	F(000) = 764
Mr = 364.37	Dx = 1.371 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.145 (4) Å	Cell parameters from 3472 reflections
b = 18.472 (7) Å	θ = 3.0–25.2°
c = 9.421 (3) Å	µ = 0.10 mm^−1
β = 91.423 (19)°	T = 130 K
V = 1764.9 (11) Å^3	Blocks, colourless
Z = 4	0.27 × 0.24 × 0.16 mm

Data collection

Bruker APEX-II CCD diffractometer	3419 independent reflections
Radiation source: Fine-focus sealed tube	2215 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.094
φ and ω scans	θmax = 26.1°, θmin = 2.0°
Absorption correction: multi-scan SADABS	h = −12→12
Tmin = 0.97, Tmax = 0.98	k = −22→22
28660 measured reflections	l = −11→11

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.131	w = 1/[σ^2(Fo^2) + (0.0603P)^2 + 0.2707P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3419 reflections	Δρmax = 0.26 e Å^−3
255 parameters	Δρmin = −0.23 e Å^−3
1 restraint	Extinction correction: SHELXL-2014/7 (Sheldrick 2014)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0050 (11)

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
N1	0.51651 (18)	0.53982 (9)	0.77636 (18)	0.0273 (4)
C2	0.4391 (2)	0.48388 (12)	0.7941 (2)	0.0288 (5)
H2	0.4561	0.4557	0.8769	0.035*
N3	0.33813 (18)	0.46140 (9)	0.70914 (18)	0.0281 (4)
C4	0.3150 (2)	0.49941 (11)	0.5901 (2)	0.0243 (5)
C5	0.3707 (2)	0.60615 (11)	0.4354 (2)	0.0247 (5)
H5	0.3042	0.5936	0.3671	0.03*
C6	0.4460 (2)	0.66645 (11)	0.4161 (2)	0.0254 (5)
C7	0.5452 (2)	0.68637 (11)	0.5188 (2)	0.0265 (5)
C8	0.5674 (2)	0.64392 (11)	0.6369 (2)	0.0272 (5)
H8	0.6341	0.6568	0.7049	0.033*
C9	0.4911 (2)	0.58153 (11)	0.6565 (2)	0.0253 (5)
C10	0.3916 (2)	0.56205 (11)	0.5574 (2)	0.0237 (5)
H11	0.207 (2)	0.5055 (12)	0.419 (2)	0.031 (6)*
N11	0.21595 (18)	0.47807 (9)	0.49875 (19)	0.0256 (4)
C12	0.1267 (2)	0.41941 (11)	0.5067 (2)	0.0266 (5)
C13	0.0353 (2)	0.41364 (11)	0.3935 (2)	0.0272 (5)
H13	0.0356	0.4487	0.3198	0.033*
C14	−0.0561 (2)	0.35748 (11)	0.3869 (2)	0.0283 (5)
C15	−0.0570 (2)	0.30668 (12)	0.4970 (2)	0.0350 (6)
H15	−0.1182	0.2678	0.4944	0.042*
C16	0.0322 (2)	0.31368 (13)	0.6094 (3)	0.0389 (6)
H16	0.0306	0.2792	0.6842	0.047*
C17	0.1244 (2)	0.36943 (12)	0.6170 (2)	0.0336 (6)
H17	0.1843	0.3733	0.6957	0.04*
C18	−0.1490 (2)	0.35361 (12)	0.2677 (2)	0.0310 (5)
C19	−0.2273 (3)	0.35234 (13)	0.1714 (3)	0.0403 (6)
H19	−0.2897	0.3513	0.0945	0.048*
O20	0.43352 (15)	0.71195 (8)	0.30247 (15)	0.0321 (4)
C21	0.3405 (2)	0.69172 (12)	0.1930 (2)	0.0347 (6)
H21A	0.3645	0.6443	0.1548	0.052*
H21B	0.3413	0.7278	0.1168	0.052*
H21C	0.2521	0.6891	0.2323	0.052*
O22	0.61062 (15)	0.74870 (8)	0.48992 (15)	0.0343 (4)
C23	0.7077 (2)	0.77249 (13)	0.5941 (2)	0.0382 (6)
H23A	0.666	0.7782	0.6862	0.057*
H23B	0.7447	0.8189	0.5645	0.057*
H23C	0.7783	0.7364	0.6025	0.057*
O24	0.82302 (15)	0.46782 (8)	0.81886 (16)	0.0362 (4)
H25	0.654 (3)	0.5508 (16)	0.870 (3)	0.077 (10)*
O25	0.72992 (16)	0.55982 (9)	0.93348 (17)	0.0362 (4)
C26	0.8266 (2)	0.51419 (11)	0.9120 (2)	0.0270 (5)
C27	0.9433 (2)	0.52588 (12)	1.0112 (2)	0.0320 (5)
H27A	0.9139	0.5209	1.1102	0.038*
H27B	0.9756	0.576	0.9993	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0247 (10)	0.0293 (10)	0.0277 (10)	0.0030 (8)	−0.0027 (8)	−0.0014 (8)
C2	0.0260 (12)	0.0308 (13)	0.0295 (12)	0.0025 (10)	−0.0029 (10)	0.0051 (9)
N3	0.0265 (10)	0.0271 (10)	0.0305 (10)	0.0020 (8)	−0.0025 (9)	0.0020 (8)
C4	0.0215 (11)	0.0251 (12)	0.0263 (11)	0.0048 (9)	−0.0003 (9)	−0.0031 (9)
C5	0.0222 (11)	0.0255 (12)	0.0262 (11)	0.0025 (9)	−0.0040 (9)	−0.0031 (9)
C6	0.0257 (12)	0.0236 (11)	0.0269 (11)	0.0026 (9)	−0.0015 (10)	−0.0019 (9)
C7	0.0257 (12)	0.0220 (12)	0.0318 (12)	−0.0001 (9)	0.0017 (10)	−0.0037 (9)
C8	0.0234 (12)	0.0266 (12)	0.0314 (12)	−0.0008 (9)	−0.0026 (10)	−0.0076 (9)
C9	0.0232 (11)	0.0264 (12)	0.0264 (11)	0.0042 (9)	0.0011 (10)	−0.0034 (9)
C10	0.0214 (11)	0.0234 (11)	0.0263 (11)	0.0036 (9)	−0.0002 (9)	−0.0018 (9)
N11	0.0273 (10)	0.0233 (10)	0.0260 (10)	−0.0020 (8)	−0.0022 (8)	0.0014 (8)
C12	0.0233 (12)	0.0240 (12)	0.0324 (12)	0.0026 (9)	0.0013 (10)	−0.0035 (9)
C13	0.0281 (12)	0.0245 (12)	0.0291 (12)	0.0002 (9)	0.0013 (10)	0.0000 (9)
C14	0.0251 (12)	0.0274 (12)	0.0323 (12)	−0.0003 (10)	0.0010 (10)	−0.0055 (9)
C15	0.0318 (14)	0.0300 (13)	0.0431 (13)	−0.0078 (10)	−0.0011 (12)	0.0029 (10)
C16	0.0393 (15)	0.0353 (14)	0.0418 (14)	−0.0075 (11)	−0.0031 (12)	0.0119 (11)
C17	0.0316 (13)	0.0317 (13)	0.0371 (13)	−0.0044 (10)	−0.0064 (11)	0.0043 (10)
C18	0.0301 (13)	0.0260 (12)	0.0371 (13)	−0.0008 (10)	0.0037 (12)	−0.0031 (10)
C19	0.0399 (15)	0.0388 (15)	0.0419 (14)	0.0027 (12)	−0.0079 (13)	−0.0093 (11)
O20	0.0331 (9)	0.0295 (9)	0.0332 (8)	−0.0062 (7)	−0.0101 (7)	0.0053 (7)
C21	0.0385 (14)	0.0348 (14)	0.0304 (12)	−0.0047 (11)	−0.0098 (11)	0.0041 (10)
O22	0.0340 (9)	0.0314 (9)	0.0371 (9)	−0.0096 (7)	−0.0077 (8)	0.0017 (7)
C23	0.0364 (14)	0.0397 (14)	0.0381 (13)	−0.0120 (11)	−0.0068 (12)	−0.0018 (11)
O24	0.0341 (10)	0.0346 (9)	0.0393 (9)	0.0009 (7)	−0.0082 (8)	−0.0073 (7)
O25	0.0280 (9)	0.0432 (10)	0.0369 (9)	0.0053 (8)	−0.0077 (8)	−0.0073 (7)
C26	0.0281 (12)	0.0258 (12)	0.0271 (11)	−0.0013 (10)	−0.0010 (10)	0.0043 (9)
C27	0.0312 (13)	0.0343 (13)	0.0303 (12)	0.0008 (10)	−0.0044 (11)	−0.0036 (10)

Geometric parameters (Å, º)

N1—C2	1.311 (3)	C14—C18	1.450 (3)
N1—C9	1.386 (3)	C15—C16	1.382 (3)
C2—N3	1.349 (3)	C15—H15	0.95
C2—H2	0.95	C16—C17	1.391 (3)
N3—C4	1.339 (3)	C16—H16	0.95
C4—N11	1.365 (3)	C17—H17	0.95
C4—C10	1.432 (3)	C18—C19	1.191 (3)
C5—C6	1.365 (3)	C19—H19	0.95
C5—C10	1.421 (3)	O20—C21	1.430 (3)
C5—H5	0.95	C21—H21A	0.98
C6—O20	1.364 (2)	C21—H21B	0.98
C6—C7	1.427 (3)	C21—H21C	0.98
C7—O22	1.360 (2)	O22—C23	1.441 (2)
C7—C8	1.376 (3)	C23—H23A	0.98
C8—C9	1.403 (3)	C23—H23B	0.98
C8—H8	0.95	C23—H23C	0.98
C9—C10	1.404 (3)	O24—C26	1.226 (2)
N11—C12	1.415 (3)	O25—C26	1.313 (3)
N11—H11	0.91 (2)	O25—H25	0.98 (2)
C12—C17	1.391 (3)	C26—C27	1.506 (3)
C12—C13	1.400 (3)	C27—C27^i	1.514 (4)
C13—C14	1.391 (3)	C27—H27A	0.99
C13—H13	0.95	C27—H27B	0.99
C14—C15	1.399 (3)
C2—N1—C9	116.22 (18)	C15—C14—C18	121.7 (2)
N1—C2—N3	127.97 (19)	C16—C15—C14	119.3 (2)
N1—C2—H2	116.0	C16—C15—H15	120.3
N3—C2—H2	116.0	C14—C15—H15	120.3
C4—N3—C2	116.75 (18)	C15—C16—C17	122.3 (2)
N3—C4—N11	119.20 (19)	C15—C16—H16	118.9
N3—C4—C10	121.26 (19)	C17—C16—H16	118.9
N11—C4—C10	119.55 (18)	C12—C17—C16	118.5 (2)
C6—C5—C10	120.2 (2)	C12—C17—H17	120.7
C6—C5—H5	119.9	C16—C17—H17	120.7
C10—C5—H5	119.9	C19—C18—C14	177.9 (2)
O20—C6—C5	124.47 (19)	C18—C19—H19	180.0
O20—C6—C7	115.05 (18)	C6—O20—C21	116.84 (16)
C5—C6—C7	120.48 (19)	O20—C21—H21A	109.5
O22—C7—C8	124.98 (19)	O20—C21—H21B	109.5
O22—C7—C6	114.97 (18)	H21A—C21—H21B	109.5
C8—C7—C6	120.04 (19)	O20—C21—H21C	109.5
C7—C8—C9	119.6 (2)	H21A—C21—H21C	109.5
C7—C8—H8	120.2	H21B—C21—H21C	109.5
C9—C8—H8	120.2	C7—O22—C23	116.77 (16)
N1—C9—C8	118.13 (19)	O22—C23—H23A	109.5
N1—C9—C10	121.01 (19)	O22—C23—H23B	109.5
C8—C9—C10	120.87 (19)	H23A—C23—H23B	109.5
C9—C10—C5	118.77 (19)	O22—C23—H23C	109.5
C9—C10—C4	116.71 (18)	H23A—C23—H23C	109.5
C5—C10—C4	124.50 (19)	H23B—C23—H23C	109.5
C4—N11—C12	130.53 (18)	C26—O25—H25	112.2 (18)
C4—N11—H11	114.6 (14)	O24—C26—O25	123.3 (2)
C12—N11—H11	114.9 (14)	O24—C26—C27	123.6 (2)
C17—C12—C13	119.7 (2)	O25—C26—C27	113.03 (19)
C17—C12—N11	124.8 (2)	C26—C27—C27^i	114.2 (2)
C13—C12—N11	115.52 (19)	C26—C27—H27A	108.7
C14—C13—C12	121.3 (2)	C27^i—C27—H27A	108.7
C14—C13—H13	119.4	C26—C27—H27B	108.7
C12—C13—H13	119.4	C27^i—C27—H27B	108.7
C13—C14—C15	118.9 (2)	H27A—C27—H27B	107.6
C13—C14—C18	119.4 (2)
C9—N1—C2—N3	0.7 (3)	N11—C4—C10—C9	179.36 (18)
N1—C2—N3—C4	1.7 (3)	N3—C4—C10—C5	−178.25 (19)
C2—N3—C4—N11	178.54 (18)	N11—C4—C10—C5	1.4 (3)
C2—N3—C4—C10	−1.8 (3)	N3—C4—N11—C12	0.1 (3)
C10—C5—C6—O20	179.86 (18)	C10—C4—N11—C12	−179.5 (2)
C10—C5—C6—C7	−0.8 (3)	C4—N11—C12—C17	−0.1 (4)
O20—C6—C7—O22	1.4 (3)	C4—N11—C12—C13	179.4 (2)
C5—C6—C7—O22	−177.96 (18)	C17—C12—C13—C14	−1.9 (3)
O20—C6—C7—C8	−179.25 (18)	N11—C12—C13—C14	178.63 (18)
C5—C6—C7—C8	1.3 (3)	C12—C13—C14—C15	0.9 (3)
O22—C7—C8—C9	178.49 (19)	C12—C13—C14—C18	179.98 (19)
C6—C7—C8—C9	−0.7 (3)	C13—C14—C15—C16	0.3 (3)
C2—N1—C9—C8	176.97 (19)	C18—C14—C15—C16	−178.8 (2)
C2—N1—C9—C10	−2.9 (3)	C14—C15—C16—C17	−0.5 (4)
C7—C8—C9—N1	179.71 (18)	C13—C12—C17—C16	1.6 (3)
C7—C8—C9—C10	−0.4 (3)	N11—C12—C17—C16	−179.0 (2)
N1—C9—C10—C5	−179.17 (18)	C15—C16—C17—C12	−0.4 (4)
C8—C9—C10—C5	0.9 (3)	C5—C6—O20—C21	−4.2 (3)
N1—C9—C10—C4	2.7 (3)	C7—C6—O20—C21	176.47 (18)
C8—C9—C10—C4	−177.15 (18)	C8—C7—O22—C23	−1.9 (3)
C6—C5—C10—C9	−0.3 (3)	C6—C7—O22—C23	177.35 (18)
C6—C5—C10—C4	177.59 (19)	O24—C26—C27—C27^i	−1.2 (4)
N3—C4—C10—C9	−0.3 (3)	O25—C26—C27—C27^i	−179.9 (2)

Symmetry code: (i) −x+2, −y+1, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O25—H25···N1	0.98 (2)	1.64 (2)	2.618 (2)	174 (3)
N11—H11···O24^ii	0.91 (2)	2.31 (2)	3.170 (3)	158.5 (19)

Symmetry code: (ii) −x+1, −y+1, −z+1.

(MP1611)

Crystal data

C18H15N3O2·0.5(C8H14O4)	Z = 2
Mr = 392.42	F(000) = 414
Triclinic, P1	Dx = 1.308 Mg m^−3
a = 7.889 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.157 (4) Å	Cell parameters from 2665 reflections
c = 14.832 (7) Å	θ = 2.4–24.4°
α = 86.153 (19)°	µ = 0.09 mm^−1
β = 83.38 (2)°	T = 130 K
γ = 69.517 (18)°	Blocks, colourless
V = 996.6 (8) Å^3	0.28 × 0.20 × 0.12 mm

Data collection

Bruker APEX-II CCD diffractometer	3506 independent reflections
Radiation source: Fine-focus sealed tube	2377 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
φ and ω scans	θmax = 25.6°, θmin = 1.4°
Absorption correction: multi-scan SADABS	h = −9→9
Tmin = 0.97, Tmax = 0.99	k = −11→11
15029 measured reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: mixed
wR(F^2) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0759P)^2] where P = (Fo^2 + 2Fc^2)/3
3506 reflections	(Δ/σ)max < 0.001
272 parameters	Δρmax = 0.33 e Å^−3
1 restraint	Δρmin = −0.33 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
N1	0.5049 (3)	0.6611 (2)	0.62907 (12)	0.0233 (5)
C2	0.4289 (3)	0.7651 (3)	0.56568 (16)	0.0225 (6)
H2	0.3233	0.8496	0.5856	0.027*
N3	0.4840 (2)	0.7643 (2)	0.47696 (12)	0.0215 (5)
C4	0.6265 (3)	0.6404 (3)	0.44643 (15)	0.0192 (5)
C5	0.8736 (3)	0.3863 (3)	0.48137 (15)	0.0193 (6)
H5	0.9162	0.3721	0.4189	0.023*
C6	0.9591 (3)	0.2779 (3)	0.54546 (15)	0.0213 (6)
C7	0.9013 (3)	0.3019 (3)	0.64031 (15)	0.0230 (6)
C8	0.7531 (3)	0.4288 (3)	0.66750 (15)	0.0238 (6)
H8	0.7138	0.444	0.7302	0.029*
C9	0.6595 (3)	0.5364 (3)	0.60203 (15)	0.0201 (6)
C10	0.7220 (3)	0.5187 (3)	0.50867 (14)	0.0174 (5)
H11	0.752 (3)	0.532 (3)	0.3311 (15)	0.031 (7)*
N11	0.6772 (3)	0.6318 (2)	0.35628 (12)	0.0187 (5)
C12	0.6008 (3)	0.7479 (3)	0.28883 (14)	0.0188 (5)
C13	0.5686 (3)	0.6988 (3)	0.20754 (14)	0.0205 (6)
H13	0.5911	0.5912	0.2	0.025*
C14	0.5034 (3)	0.8064 (3)	0.13660 (15)	0.0220 (6)
C15	0.4714 (3)	0.9632 (3)	0.14857 (16)	0.0275 (6)
H15	0.4277	1.0376	0.1013	0.033*
C16	0.5035 (3)	1.0109 (3)	0.22978 (16)	0.0280 (6)
H16	0.4802	1.1185	0.2376	0.034*
C17	0.5691 (3)	0.9048 (3)	0.30013 (16)	0.0230 (6)
H17	0.5918	0.9393	0.355	0.028*
C18	0.4684 (3)	0.7559 (3)	0.05265 (16)	0.0272 (6)
C19	0.4407 (3)	0.7144 (3)	−0.01672 (17)	0.0345 (7)
H19	0.4186	0.6813	−0.0722	0.041*
O20	1.1032 (2)	0.14567 (19)	0.52593 (10)	0.0281 (4)
C21	1.1560 (3)	0.1125 (3)	0.43072 (16)	0.0320 (7)
H21A	1.0515	0.109	0.4022	0.048*
H21B	1.2548	0.0116	0.4247	0.048*
H21C	1.1974	0.1945	0.4008	0.048*
O22	1.0030 (2)	0.1916 (2)	0.69722 (10)	0.0319 (5)
C23	0.9730 (4)	0.2246 (4)	0.79337 (16)	0.0411 (8)
H23A	0.982	0.3267	0.8018	0.062*
H23B	1.0651	0.144	0.8258	0.062*
H23C	0.8517	0.2251	0.8174	0.062*
H24	0.384 (5)	0.677 (4)	0.7194 (18)	0.099 (13)*
O24	0.3148 (2)	0.7039 (2)	0.78516 (11)	0.0325 (5)
O25	0.0956 (2)	0.6337 (2)	0.73686 (11)	0.0302 (5)
C26	0.1490 (3)	0.7026 (3)	0.79021 (16)	0.0248 (6)
C27	0.0194 (3)	0.7900 (3)	0.86841 (16)	0.0288 (6)
H27A	−0.0722	0.8842	0.8439	0.035*
H27B	0.0886	0.8247	0.9088	0.035*
C28	−0.0786 (3)	0.6909 (3)	0.92413 (16)	0.0302 (6)
H28A	−0.1681	0.7567	0.9704	0.036*
H28B	−0.1464	0.6553	0.8834	0.036*
C29	0.0493 (3)	0.5487 (3)	0.97159 (16)	0.0291 (6)
H29A	0.1186	0.5841	1.0116	0.035*
H29B	0.1376	0.4819	0.9252	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0215 (11)	0.0239 (12)	0.0255 (11)	−0.0097 (10)	−0.0006 (9)	−0.0004 (10)
C2	0.0202 (13)	0.0209 (14)	0.0273 (13)	−0.0088 (11)	0.0024 (10)	−0.0050 (11)
N3	0.0168 (11)	0.0228 (12)	0.0243 (11)	−0.0066 (10)	0.0005 (8)	−0.0018 (9)
C4	0.0157 (13)	0.0194 (13)	0.0249 (13)	−0.0092 (11)	−0.0006 (10)	−0.0018 (11)
C5	0.0155 (12)	0.0232 (14)	0.0194 (12)	−0.0076 (11)	−0.0003 (10)	0.0011 (11)
C6	0.0140 (13)	0.0199 (14)	0.0284 (14)	−0.0047 (11)	−0.0010 (10)	0.0013 (11)
C7	0.0180 (13)	0.0267 (15)	0.0257 (13)	−0.0099 (12)	−0.0055 (10)	0.0078 (12)
C8	0.0210 (14)	0.0337 (16)	0.0187 (12)	−0.0136 (13)	−0.0010 (10)	0.0051 (12)
C9	0.0166 (13)	0.0197 (14)	0.0253 (13)	−0.0085 (11)	−0.0002 (10)	−0.0010 (11)
C10	0.0157 (12)	0.0176 (13)	0.0203 (12)	−0.0074 (11)	−0.0038 (10)	0.0026 (10)
N11	0.0201 (11)	0.0151 (11)	0.0179 (11)	−0.0024 (10)	−0.0016 (8)	−0.0002 (9)
C12	0.0125 (12)	0.0208 (14)	0.0208 (12)	−0.0045 (11)	0.0011 (9)	0.0023 (11)
C13	0.0161 (12)	0.0196 (13)	0.0251 (13)	−0.0064 (11)	0.0008 (10)	0.0010 (11)
C14	0.0158 (12)	0.0263 (15)	0.0232 (13)	−0.0075 (11)	−0.0010 (10)	0.0030 (11)
C15	0.0243 (14)	0.0256 (15)	0.0297 (14)	−0.0069 (12)	−0.0018 (11)	0.0094 (12)
C16	0.0313 (15)	0.0178 (14)	0.0331 (15)	−0.0073 (12)	−0.0010 (12)	0.0011 (12)
C17	0.0236 (14)	0.0203 (14)	0.0265 (13)	−0.0098 (12)	−0.0008 (10)	−0.0020 (11)
C18	0.0231 (14)	0.0324 (16)	0.0257 (14)	−0.0103 (12)	−0.0027 (11)	0.0071 (12)
C19	0.0340 (16)	0.0467 (19)	0.0272 (15)	−0.0190 (14)	−0.0068 (12)	0.0029 (13)
O20	0.0224 (10)	0.0253 (11)	0.0283 (10)	0.0012 (8)	−0.0020 (7)	0.0042 (8)
C21	0.0254 (14)	0.0259 (16)	0.0359 (16)	0.0008 (12)	0.0006 (11)	0.0016 (13)
O22	0.0257 (10)	0.0387 (11)	0.0260 (10)	−0.0055 (9)	−0.0069 (7)	0.0120 (8)
C23	0.0288 (16)	0.064 (2)	0.0251 (15)	−0.0109 (15)	−0.0070 (12)	0.0137 (14)
O24	0.0306 (10)	0.0447 (12)	0.0240 (10)	−0.0169 (9)	0.0038 (8)	−0.0042 (9)
O25	0.0267 (10)	0.0335 (11)	0.0294 (10)	−0.0076 (9)	−0.0076 (8)	−0.0025 (9)
C26	0.0257 (14)	0.0240 (14)	0.0212 (13)	−0.0055 (12)	−0.0017 (11)	0.0058 (11)
C27	0.0251 (14)	0.0260 (15)	0.0291 (14)	−0.0020 (12)	0.0008 (11)	−0.0013 (12)
C28	0.0277 (14)	0.0312 (16)	0.0259 (14)	−0.0053 (13)	0.0043 (11)	0.0011 (12)
C29	0.0247 (14)	0.0327 (16)	0.0256 (14)	−0.0059 (13)	0.0007 (11)	0.0020 (12)

Geometric parameters (Å, º)

N1—C2	1.327 (3)	C16—C17	1.392 (3)
N1—C9	1.387 (3)	C16—H16	0.95
C2—N3	1.337 (3)	C17—H17	0.95
C2—H2	0.95	C18—C19	1.189 (3)
N3—C4	1.347 (3)	C19—H19	0.95
C4—N11	1.350 (3)	O20—C21	1.447 (3)
C4—C10	1.448 (3)	C21—H21A	0.98
C5—C6	1.377 (3)	C21—H21B	0.98
C5—C10	1.416 (3)	C21—H21C	0.98
C5—H5	0.95	O22—C23	1.453 (3)
C6—O20	1.360 (3)	C23—H23A	0.98
C6—C7	1.435 (3)	C23—H23B	0.98
C7—O22	1.361 (3)	C23—H23C	0.98
C7—C8	1.372 (3)	O24—C26	1.305 (3)
C8—C9	1.410 (3)	O24—H24	1.06 (2)
C8—H8	0.95	O25—C26	1.237 (3)
C9—C10	1.416 (3)	C26—C27	1.520 (3)
N11—C12	1.429 (3)	C27—C28	1.532 (3)
N11—H11	0.97 (3)	C27—H27A	0.99
C12—C17	1.388 (3)	C27—H27B	0.99
C12—C13	1.394 (3)	C28—C29	1.526 (3)
C13—C14	1.405 (3)	C28—H28A	0.99
C13—H13	0.95	C28—H28B	0.99
C14—C15	1.387 (3)	C29—C29^i	1.531 (5)
C14—C18	1.445 (3)	C29—H29A	0.99
C15—C16	1.387 (3)	C29—H29B	0.99
C15—H15	0.95
C2—N1—C9	117.6 (2)	C17—C16—H16	119.2
N1—C2—N3	127.3 (2)	C12—C17—C16	119.0 (2)
N1—C2—H2	116.3	C12—C17—H17	120.5
N3—C2—H2	116.3	C16—C17—H17	120.5
C2—N3—C4	117.3 (2)	C19—C18—C14	179.5 (3)
N3—C4—N11	118.4 (2)	C18—C19—H19	180.0
N3—C4—C10	120.8 (2)	C6—O20—C21	116.38 (17)
N11—C4—C10	120.8 (2)	O20—C21—H21A	109.5
C6—C5—C10	119.9 (2)	O20—C21—H21B	109.5
C6—C5—H5	120.0	H21A—C21—H21B	109.5
C10—C5—H5	120.0	O20—C21—H21C	109.5
O20—C6—C5	124.3 (2)	H21A—C21—H21C	109.5
O20—C6—C7	115.17 (19)	H21B—C21—H21C	109.5
C5—C6—C7	120.5 (2)	C7—O22—C23	117.3 (2)
O22—C7—C8	125.0 (2)	O22—C23—H23A	109.5
O22—C7—C6	115.0 (2)	O22—C23—H23B	109.5
C8—C7—C6	120.0 (2)	H23A—C23—H23B	109.5
C7—C8—C9	119.8 (2)	O22—C23—H23C	109.5
C7—C8—H8	120.1	H23A—C23—H23C	109.5
C9—C8—H8	120.1	H23B—C23—H23C	109.5
N1—C9—C8	119.9 (2)	C26—O24—H24	112.4 (19)
N1—C9—C10	119.6 (2)	O25—C26—O24	124.0 (2)
C8—C9—C10	120.5 (2)	O25—C26—C27	120.0 (2)
C9—C10—C5	119.1 (2)	O24—C26—C27	116.1 (2)
C9—C10—C4	117.2 (2)	C26—C27—C28	112.8 (2)
C5—C10—C4	123.8 (2)	C26—C27—H27A	109.0
C4—N11—C12	126.0 (2)	C28—C27—H27A	109.0
C4—N11—H11	119.3 (14)	C26—C27—H27B	109.0
C12—N11—H11	113.3 (14)	C28—C27—H27B	109.0
C17—C12—C13	119.9 (2)	H27A—C27—H27B	107.8
C17—C12—N11	121.9 (2)	C29—C28—C27	113.5 (2)
C13—C12—N11	118.1 (2)	C29—C28—H28A	108.9
C12—C13—C14	120.8 (2)	C27—C28—H28A	108.9
C12—C13—H13	119.6	C29—C28—H28B	108.9
C14—C13—H13	119.6	C27—C28—H28B	108.9
C15—C14—C13	118.9 (2)	H28A—C28—H28B	107.7
C15—C14—C18	120.2 (2)	C28—C29—C29^i	113.4 (3)
C13—C14—C18	120.9 (2)	C28—C29—H29A	108.9
C16—C15—C14	119.8 (2)	C29^i—C29—H29A	108.9
C16—C15—H15	120.1	C28—C29—H29B	108.9
C14—C15—H15	120.1	C29^i—C29—H29B	108.9
C15—C16—C17	121.6 (2)	H29A—C29—H29B	107.7
C15—C16—H16	119.2
C9—N1—C2—N3	0.1 (3)	N3—C4—C10—C5	−179.4 (2)
N1—C2—N3—C4	4.1 (3)	N11—C4—C10—C5	1.2 (3)
C2—N3—C4—N11	175.64 (19)	N3—C4—N11—C12	4.3 (3)
C2—N3—C4—C10	−3.8 (3)	C10—C4—N11—C12	−176.24 (19)
C10—C5—C6—O20	178.7 (2)	C4—N11—C12—C17	45.9 (3)
C10—C5—C6—C7	−3.0 (3)	C4—N11—C12—C13	−138.1 (2)
O20—C6—C7—O22	2.2 (3)	C17—C12—C13—C14	−0.3 (3)
C5—C6—C7—O22	−176.24 (19)	N11—C12—C13—C14	−176.40 (19)
O20—C6—C7—C8	−177.7 (2)	C12—C13—C14—C15	0.1 (3)
C5—C6—C7—C8	3.8 (3)	C12—C13—C14—C18	−179.4 (2)
O22—C7—C8—C9	179.3 (2)	C13—C14—C15—C16	−0.2 (3)
C6—C7—C8—C9	−0.8 (3)	C18—C14—C15—C16	179.3 (2)
C2—N1—C9—C8	175.46 (19)	C14—C15—C16—C17	0.6 (4)
C2—N1—C9—C10	−4.4 (3)	C13—C12—C17—C16	0.6 (3)
C7—C8—C9—N1	177.2 (2)	N11—C12—C17—C16	176.6 (2)
C7—C8—C9—C10	−3.0 (3)	C15—C16—C17—C12	−0.8 (4)
N1—C9—C10—C5	−176.38 (19)	C5—C6—O20—C21	−6.0 (3)
C8—C9—C10—C5	3.8 (3)	C7—C6—O20—C21	175.57 (18)
N1—C9—C10—C4	4.4 (3)	C8—C7—O22—C23	−11.4 (3)
C8—C9—C10—C4	−175.47 (19)	C6—C7—O22—C23	168.65 (19)
C6—C5—C10—C9	−0.8 (3)	O25—C26—C27—C28	50.7 (3)
C6—C5—C10—C4	178.4 (2)	O24—C26—C27—C28	−128.2 (2)
N3—C4—C10—C9	−0.2 (3)	C26—C27—C28—C29	63.3 (3)
N11—C4—C10—C9	−179.63 (19)	C27—C28—C29—C29^i	179.1 (3)

Symmetry code: (i) −x, −y+1, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O24—H24···N1	1.06 (2)	1.54 (3)	2.583 (3)	168 (3)
N11—H11···O25^ii	0.97 (3)	1.85 (3)	2.804 (3)	168 (2)

Symmetry code: (ii) −x+1, −y+1, −z+1.

(MP1614)

Crystal data

C18H15N3O2·0.5(C12H22O4)	F(000) = 892
Mr = 420.48	Dx = 1.319 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.5496 (16) Å	Cell parameters from 4114 reflections
b = 16.434 (4) Å	θ = 2.4–22.1°
c = 17.094 (4) Å	µ = 0.09 mm^−1
β = 93.547 (12)°	T = 130 K
V = 2116.8 (8) Å^3	Blocks, colourless
Z = 4	0.26 × 0.17 × 0.08 mm

Data collection

Bruker APEX-II CCD diffractometer	3787 independent reflections
Radiation source: Fine-focus sealed tube	2480 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.097
φ and ω scans	θmax = 25.2°, θmin = 1.7°
Absorption correction: multi-scan SADABS	h = −9→8
Tmin = 0.98, Tmax = 0.99	k = −19→19
36479 measured reflections	l = −20→20

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.158	w = 1/[σ^2(Fo^2) + (0.0776P)^2 + 0.6292P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3787 reflections	Δρmax = 0.36 e Å^−3
291 parameters	Δρmin = −0.23 e Å^−3
1 restraint	Extinction correction: SHELXL-2014/7 (Sheldrick 2014
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0082 (14)

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
N1	0.6254 (3)	0.65958 (13)	0.48852 (13)	0.0293 (6)
C2	0.7057 (4)	0.64947 (17)	0.55798 (17)	0.0344 (7)
H2	0.7081	0.6954	0.5918	0.041*
N3	0.7847 (3)	0.58218 (14)	0.58695 (13)	0.0323 (6)
C4	0.7814 (3)	0.51752 (15)	0.54094 (15)	0.0246 (6)
C5	0.7046 (3)	0.45603 (16)	0.40816 (15)	0.0251 (6)
H5	0.7578	0.4055	0.4231	0.03*
C6	0.6300 (3)	0.46588 (15)	0.33421 (15)	0.0272 (6)
C7	0.5480 (3)	0.54088 (16)	0.31148 (15)	0.0270 (6)
C8	0.5459 (3)	0.60287 (16)	0.36330 (15)	0.0271 (6)
H8	0.4905	0.6528	0.3482	0.033*
C9	0.6248 (3)	0.59394 (15)	0.43919 (15)	0.0231 (6)
C10	0.7032 (3)	0.52037 (15)	0.46265 (15)	0.0235 (6)
H11	0.844 (3)	0.4048 (18)	0.5368 (17)	0.039 (9)*
N11	0.8545 (3)	0.44731 (14)	0.56861 (13)	0.0269 (5)
C12	0.9348 (3)	0.42888 (16)	0.64288 (15)	0.0267 (6)
C13	1.0138 (3)	0.35264 (16)	0.65014 (15)	0.0260 (6)
H13	1.0121	0.3174	0.606	0.031*
C14	1.0952 (3)	0.32727 (17)	0.72108 (16)	0.0292 (6)
C15	1.0975 (3)	0.37897 (18)	0.78553 (16)	0.0354 (7)
H15	1.151	0.3621	0.8346	0.042*
C16	1.0217 (3)	0.45443 (18)	0.77759 (16)	0.0364 (7)
H16	1.0254	0.49	0.8215	0.044*
C17	0.9400 (3)	0.48033 (18)	0.70726 (15)	0.0325 (7)
H17	0.8879	0.5329	0.7031	0.039*
C18	1.1834 (3)	0.25032 (18)	0.72682 (15)	0.0319 (7)
C19	1.2620 (4)	0.1888 (2)	0.73251 (17)	0.0398 (8)
H19	1.3256	0.1389	0.7371	0.048*
O20	0.6278 (2)	0.40878 (11)	0.27656 (10)	0.0345 (5)
C21	0.7238 (4)	0.33589 (17)	0.29364 (19)	0.0433 (8)
H21A	0.8485	0.349	0.3073	0.065*
H21B	0.7158	0.3003	0.2476	0.065*
H21C	0.6733	0.3081	0.3378	0.065*
O22	0.4801 (2)	0.54319 (11)	0.23643 (10)	0.0340 (5)
C23	0.4111 (4)	0.61974 (18)	0.20932 (17)	0.0403 (8)
H23A	0.3111	0.6353	0.24	0.06*
H23B	0.3707	0.6153	0.1539	0.06*
H23C	0.5042	0.6612	0.2154	0.06*
O24	0.2162 (2)	0.71648 (11)	0.50407 (12)	0.0404 (5)
H25	0.503 (5)	0.737 (2)	0.463 (2)	0.096 (14)*
O25	0.4281 (3)	0.78249 (12)	0.44477 (13)	0.0455 (6)
C26	0.2657 (4)	0.77359 (18)	0.46550 (17)	0.0335 (7)
C27	0.1432 (4)	0.84005 (17)	0.43659 (17)	0.0371 (7)
H27A	0.0938	0.8262	0.3833	0.045*
H27B	0.2116	0.8912	0.4329	0.045*
C28	−0.0082 (4)	0.85381 (18)	0.48929 (17)	0.0385 (7)
H28A	−0.0699	0.8015	0.4968	0.046*
H28B	0.0408	0.8725	0.5413	0.046*
C29	−0.1411 (4)	0.91585 (18)	0.45635 (16)	0.0364 (7)
H29A	−0.1936	0.896	0.4054	0.044*
H29B	−0.0783	0.9674	0.4467	0.044*
C30	−0.2888 (3)	0.93252 (17)	0.51023 (16)	0.0338 (7)
H30A	−0.3473	0.8806	0.5227	0.041*
H30B	−0.2376	0.956	0.5599	0.041*
C31	−0.4260 (3)	0.99058 (18)	0.47367 (16)	0.0370 (7)
H31A	−0.3665	1.042	0.4604	0.044*
H31B	−0.4775	0.9666	0.4242	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0296 (12)	0.0266 (13)	0.0314 (13)	0.0020 (10)	0.0006 (10)	−0.0025 (10)
C2	0.0389 (16)	0.0305 (16)	0.0336 (17)	0.0017 (13)	−0.0003 (13)	−0.0076 (13)
N3	0.0329 (13)	0.0304 (14)	0.0333 (14)	0.0056 (10)	0.0001 (10)	−0.0014 (11)
C4	0.0215 (13)	0.0250 (15)	0.0273 (15)	0.0000 (11)	0.0029 (11)	0.0038 (12)
C5	0.0214 (13)	0.0221 (14)	0.0313 (15)	−0.0006 (11)	−0.0009 (11)	0.0021 (12)
C6	0.0247 (14)	0.0243 (15)	0.0322 (16)	−0.0051 (12)	−0.0001 (12)	−0.0061 (12)
C7	0.0199 (13)	0.0311 (16)	0.0294 (15)	−0.0027 (12)	−0.0042 (11)	0.0036 (13)
C8	0.0212 (14)	0.0268 (15)	0.0330 (16)	0.0012 (11)	−0.0015 (12)	0.0027 (13)
C9	0.0167 (13)	0.0236 (14)	0.0291 (15)	−0.0009 (11)	0.0018 (11)	0.0015 (12)
C10	0.0182 (13)	0.0257 (15)	0.0268 (14)	−0.0032 (11)	0.0025 (11)	0.0010 (12)
N11	0.0259 (12)	0.0279 (13)	0.0266 (13)	0.0016 (10)	−0.0021 (10)	−0.0003 (11)
C12	0.0177 (13)	0.0346 (16)	0.0278 (15)	−0.0010 (11)	0.0015 (11)	0.0035 (12)
C13	0.0224 (13)	0.0316 (15)	0.0241 (14)	−0.0009 (12)	0.0013 (11)	0.0027 (12)
C14	0.0210 (13)	0.0367 (17)	0.0297 (16)	−0.0009 (12)	0.0008 (11)	0.0063 (13)
C15	0.0301 (15)	0.0492 (19)	0.0263 (16)	0.0015 (14)	−0.0015 (12)	0.0042 (14)
C16	0.0374 (16)	0.0458 (19)	0.0258 (15)	0.0017 (14)	−0.0009 (12)	−0.0041 (14)
C17	0.0310 (15)	0.0384 (17)	0.0278 (16)	0.0033 (13)	−0.0010 (12)	−0.0008 (13)
C18	0.0302 (15)	0.0394 (18)	0.0252 (16)	−0.0037 (14)	−0.0057 (12)	0.0064 (13)
C19	0.0398 (17)	0.0418 (19)	0.0362 (18)	0.0035 (15)	−0.0105 (14)	0.0043 (15)
O20	0.0416 (11)	0.0261 (11)	0.0350 (11)	0.0004 (9)	−0.0048 (9)	−0.0050 (9)
C21	0.0543 (19)	0.0274 (17)	0.0475 (19)	0.0058 (14)	−0.0027 (15)	−0.0068 (14)
O22	0.0361 (11)	0.0334 (11)	0.0309 (11)	0.0033 (9)	−0.0110 (9)	0.0009 (9)
C23	0.0428 (17)	0.0406 (18)	0.0360 (17)	0.0052 (14)	−0.0096 (14)	0.0055 (14)
O24	0.0427 (12)	0.0308 (12)	0.0469 (13)	0.0014 (9)	−0.0034 (10)	0.0107 (10)
O25	0.0357 (12)	0.0328 (12)	0.0690 (16)	0.0066 (10)	0.0102 (11)	0.0077 (11)
C26	0.0357 (17)	0.0311 (17)	0.0337 (17)	0.0025 (13)	0.0009 (13)	−0.0061 (14)
C27	0.0379 (16)	0.0352 (17)	0.0380 (17)	0.0053 (13)	0.0009 (13)	0.0015 (14)
C28	0.0392 (16)	0.0366 (17)	0.0398 (18)	0.0059 (14)	0.0019 (14)	0.0017 (14)
C29	0.0371 (16)	0.0376 (17)	0.0340 (17)	0.0051 (13)	−0.0026 (13)	0.0000 (13)
C30	0.0307 (15)	0.0328 (16)	0.0374 (17)	0.0053 (13)	−0.0025 (13)	0.0003 (13)
C31	0.0365 (16)	0.0453 (18)	0.0288 (16)	0.0056 (14)	−0.0020 (12)	0.0014 (14)

Geometric parameters (Å, º)

N1—C2	1.310 (3)	C18—C19	1.174 (4)
N1—C9	1.369 (3)	C19—H19	0.95
C2—N3	1.337 (3)	O20—C21	1.421 (3)
C2—H2	0.95	C21—H21A	0.98
N3—C4	1.321 (3)	C21—H21B	0.98
C4—N11	1.352 (3)	C21—H21C	0.98
C4—C10	1.430 (3)	O22—C23	1.428 (3)
C5—C6	1.361 (3)	C23—H23A	0.98
C5—C10	1.410 (3)	C23—H23B	0.98
C5—H5	0.95	C23—H23C	0.98
C6—O20	1.360 (3)	O24—C26	1.219 (3)
C6—C7	1.422 (4)	O25—C26	1.305 (3)
C7—C8	1.351 (4)	O25—H25	0.98 (3)
C7—O22	1.352 (3)	C26—C27	1.495 (4)
C8—C9	1.402 (3)	C27—C28	1.515 (4)
C8—H8	0.95	C27—H27A	0.99
C9—C10	1.394 (3)	C27—H27B	0.99
N11—C12	1.406 (3)	C28—C29	1.515 (4)
N11—H11	0.89 (3)	C28—H28A	0.99
C12—C17	1.386 (4)	C28—H28B	0.99
C12—C13	1.390 (4)	C29—C30	1.515 (4)
C13—C14	1.389 (3)	C29—H29A	0.99
C13—H13	0.95	C29—H29B	0.99
C14—C15	1.390 (4)	C30—C31	1.514 (4)
C14—C18	1.430 (4)	C30—H30A	0.99
C15—C16	1.369 (4)	C30—H30B	0.99
C15—H15	0.95	C31—C31^i	1.510 (5)
C16—C17	1.384 (4)	C31—H31A	0.99
C16—H16	0.95	C31—H31B	0.99
C17—H17	0.95
C2—N1—C9	116.2 (2)	C6—O20—C21	116.7 (2)
N1—C2—N3	127.7 (3)	O20—C21—H21A	109.5
N1—C2—H2	116.2	O20—C21—H21B	109.5
N3—C2—H2	116.2	H21A—C21—H21B	109.5
C4—N3—C2	116.9 (2)	O20—C21—H21C	109.5
N3—C4—N11	119.1 (2)	H21A—C21—H21C	109.5
N3—C4—C10	121.5 (2)	H21B—C21—H21C	109.5
N11—C4—C10	119.4 (2)	C7—O22—C23	116.2 (2)
C6—C5—C10	120.3 (2)	O22—C23—H23A	109.5
C6—C5—H5	119.8	O22—C23—H23B	109.5
C10—C5—H5	119.8	H23A—C23—H23B	109.5
O20—C6—C5	125.2 (2)	O22—C23—H23C	109.5
O20—C6—C7	114.5 (2)	H23A—C23—H23C	109.5
C5—C6—C7	120.3 (2)	H23B—C23—H23C	109.5
C8—C7—O22	125.6 (2)	C26—O25—H25	111 (2)
C8—C7—C6	119.8 (2)	O24—C26—O25	123.9 (3)
O22—C7—C6	114.6 (2)	O24—C26—C27	122.5 (3)
C7—C8—C9	120.4 (2)	O25—C26—C27	113.6 (3)
C7—C8—H8	119.8	C26—C27—C28	112.7 (2)
C9—C8—H8	119.8	C26—C27—H27A	109.0
N1—C9—C10	121.4 (2)	C28—C27—H27A	109.0
N1—C9—C8	118.2 (2)	C26—C27—H27B	109.0
C10—C9—C8	120.4 (2)	C28—C27—H27B	109.0
C9—C10—C5	118.7 (2)	H27A—C27—H27B	107.8
C9—C10—C4	116.2 (2)	C29—C28—C27	112.7 (2)
C5—C10—C4	125.1 (2)	C29—C28—H28A	109.0
C4—N11—C12	130.1 (2)	C27—C28—H28A	109.0
C4—N11—H11	116.2 (18)	C29—C28—H28B	109.0
C12—N11—H11	113.6 (18)	C27—C28—H28B	109.0
C17—C12—C13	119.2 (2)	H28A—C28—H28B	107.8
C17—C12—N11	125.1 (2)	C28—C29—C30	113.1 (2)
C13—C12—N11	115.7 (2)	C28—C29—H29A	109.0
C14—C13—C12	120.8 (3)	C30—C29—H29A	109.0
C14—C13—H13	119.6	C28—C29—H29B	109.0
C12—C13—H13	119.6	C30—C29—H29B	109.0
C13—C14—C15	119.4 (3)	H29A—C29—H29B	107.8
C13—C14—C18	120.3 (2)	C31—C30—C29	111.9 (2)
C15—C14—C18	120.2 (2)	C31—C30—H30A	109.2
C16—C15—C14	119.4 (3)	C29—C30—H30A	109.2
C16—C15—H15	120.3	C31—C30—H30B	109.2
C14—C15—H15	120.3	C29—C30—H30B	109.2
C15—C16—C17	121.7 (3)	H30A—C30—H30B	107.9
C15—C16—H16	119.1	C31^i—C31—C30	113.3 (3)
C17—C16—H16	119.1	C31^i—C31—H31A	108.9
C16—C17—C12	119.4 (3)	C30—C31—H31A	108.9
C16—C17—H17	120.3	C31^i—C31—H31B	108.9
C12—C17—H17	120.3	C30—C31—H31B	108.9
C19—C18—C14	177.3 (3)	H31A—C31—H31B	107.7
C18—C19—H19	180.0
C9—N1—C2—N3	−1.2 (4)	N11—C4—C10—C5	−4.1 (4)
N1—C2—N3—C4	−0.5 (4)	N3—C4—N11—C12	1.8 (4)
C2—N3—C4—N11	−177.9 (2)	C10—C4—N11—C12	−178.5 (2)
C2—N3—C4—C10	2.5 (4)	C4—N11—C12—C17	6.4 (4)
C10—C5—C6—O20	178.3 (2)	C4—N11—C12—C13	−173.6 (2)
C10—C5—C6—C7	−0.8 (4)	C17—C12—C13—C14	0.9 (4)
O20—C6—C7—C8	−178.5 (2)	N11—C12—C13—C14	−179.1 (2)
C5—C6—C7—C8	0.7 (4)	C12—C13—C14—C15	0.0 (4)
O20—C6—C7—O22	0.4 (3)	C12—C13—C14—C18	−177.0 (2)
C5—C6—C7—O22	179.5 (2)	C13—C14—C15—C16	−1.0 (4)
O22—C7—C8—C9	−178.3 (2)	C18—C14—C15—C16	176.0 (2)
C6—C7—C8—C9	0.4 (4)	C14—C15—C16—C17	1.1 (4)
C2—N1—C9—C10	1.0 (4)	C15—C16—C17—C12	−0.2 (4)
C2—N1—C9—C8	−177.8 (2)	C13—C12—C17—C16	−0.8 (4)
C7—C8—C9—N1	177.4 (2)	N11—C12—C17—C16	179.3 (2)
C7—C8—C9—C10	−1.4 (4)	C5—C6—O20—C21	−5.4 (4)
N1—C9—C10—C5	−177.5 (2)	C7—C6—O20—C21	173.7 (2)
C8—C9—C10—C5	1.3 (3)	C8—C7—O22—C23	4.2 (4)
N1—C9—C10—C4	0.8 (3)	C6—C7—O22—C23	−174.5 (2)
C8—C9—C10—C4	179.5 (2)	O24—C26—C27—C28	28.8 (4)
C6—C5—C10—C9	−0.2 (4)	O25—C26—C27—C28	−151.9 (2)
C6—C5—C10—C4	−178.3 (2)	C26—C27—C28—C29	−174.9 (2)
N3—C4—C10—C9	−2.6 (3)	C27—C28—C29—C30	−177.6 (2)
N11—C4—C10—C9	177.7 (2)	C28—C29—C30—C31	−176.3 (2)
N3—C4—C10—C5	175.5 (2)	C29—C30—C31—C31^i	−179.2 (3)

Symmetry code: (i) −x−1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O24^ii	0.89 (3)	2.15 (3)	2.999 (3)	160 (3)
O25—H25···N1	0.98 (3)	1.61 (3)	2.592 (3)	177 (4)

Symmetry code: (ii) −x+1, −y+1, −z+1.