Five concomitant polymorphs of a green fluorescent protein chromophore (GFPc) analogue: understanding variations in photoluminescence with π-stacking interactions

The synthetically modified green fluorescent protein chromophore analogue 3,4,5-tri­meth­oxybenzyl­idene imidazolinone (1) yielded five polymorphs (I, II, III, IV, V) concomitantly irrespective of the solvent used for crystallization. The pentamorphic modification of 1 is solely due to the interplay of iso-energetic weak intermolecular interactions in molecular associations as well as the conformational flexibility offered by a C—C single bond, which connects the electron-deficient moiety imidazolinone with the electron-rich tri­meth­oxybenzyl­idene group. A common structural feature observed in all the polymorphs is the formation of a `zero-dimensional' centrosymmetric dimeric unit through a short and linear C—H...O hydrogen bond engaging phenyl C—H and imidazolinone carbonyl oxygen. However, the networking of these dimeric units showed a subtle difference in all the polymorphs. The 2D isostructurality was observed between polymorphs I, II and III, while the other two polymorphs IV and V revealed only `zero-dimensional' isostructurality. The different fluorescence emissions of Form I (blue) and Forms II to V (yellow) were attributed to the differences in π-stacking interactions. It shows that one can modulate the photophysical properties of these smart materials by slightly altering their crystal structure. Such an approach will aid in developing new multi-colour organic fluorescent materials of varying crystal structures for live-cell imaging and fluorescent sensing applications.

Computing details

For all structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014); molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.

(Form_I)

Crystal data

C15H18N2O4	F(000) = 1232
Mr = 290.31	Dx = 1.343 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.7410 (4) Å	Cell parameters from 4617 reflections
b = 7.7542 (3) Å	θ = 3.1–30.5°
c = 29.3961 (11) Å	µ = 0.10 mm^−1
β = 98.600 (1)°	T = 100 K
V = 2871.57 (18) Å^3	BLOCK, yellow
Z = 8	0.12 × 0.09 × 0.07 mm

Data collection

Bruker D8 VENTURE Kappa Duo PHOTON II CPAD diffractometer	4321 independent reflections
Radiation source: micro-focus sealed tube, Incoatech IµS HB	3469 reflections with I > 2σ(I)
Multilayer mirrors monochromator	Rint = 0.044
Detector resolution: 7.39 pixels mm^-1	θmax = 30.5°, θmin = 3.1°
φ and ω scans	h = −12→18
Absorption correction: multi-scan SADABS (Bruker, 2006)	k = −11→9
Tmin = 0.988, Tmax = 0.993	l = −41→41
13345 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.127	w = 1/[σ^2(Fo^2) + (0.0443P)^2 + 2.8645P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
4321 reflections	Δρmax = 0.41 e Å^−3
195 parameters	Δρmin = −0.28 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
O1	0.35202 (9)	0.04278 (14)	0.47836 (4)	0.0214 (2)
O2	0.22267 (9)	0.73353 (13)	0.28496 (3)	0.0185 (2)
O3	0.14505 (9)	0.97970 (13)	0.33281 (3)	0.0180 (2)
O4	0.11166 (9)	0.92960 (13)	0.41965 (3)	0.0186 (2)
N1	0.41857 (10)	−0.02598 (15)	0.41136 (4)	0.0164 (2)
N2	0.36524 (10)	0.20249 (15)	0.36602 (4)	0.0156 (2)
C1	0.23687 (11)	0.51371 (18)	0.39727 (5)	0.0141 (3)
C2	0.25098 (11)	0.54141 (18)	0.35129 (5)	0.0148 (3)
H2	0.2837	0.4558	0.3350	0.018*
C3	0.21660 (11)	0.69512 (18)	0.32987 (4)	0.0139 (3)
C4	0.17130 (11)	0.82467 (18)	0.35390 (5)	0.0143 (3)
C5	0.15675 (11)	0.79584 (18)	0.39952 (5)	0.0147 (3)
C6	0.18760 (11)	0.64024 (18)	0.42089 (4)	0.0147 (3)
H6	0.1753	0.6195	0.4515	0.018*
C7	0.27309 (12)	0.35744 (18)	0.42238 (5)	0.0155 (3)
H7	0.2546	0.3476	0.4524	0.019*
C8	0.32927 (11)	0.22519 (18)	0.40873 (5)	0.0151 (3)
C9	0.36436 (11)	0.07515 (19)	0.43876 (5)	0.0159 (3)
C10	0.41519 (11)	0.05607 (18)	0.36907 (5)	0.0151 (3)
C11	0.46338 (12)	−0.02340 (19)	0.33125 (5)	0.0195 (3)
H11A	0.4597	0.0580	0.3055	0.029*
H11B	0.4245	−0.1288	0.3209	0.029*
H11C	0.5377	−0.0519	0.3423	0.029*
C12	0.47035 (13)	−0.18811 (19)	0.42624 (5)	0.0209 (3)
H12A	0.5054	−0.1771	0.4581	0.031*
H12B	0.5233	−0.2161	0.4064	0.031*
H12C	0.4172	−0.2802	0.4242	0.031*
C13	0.25646 (13)	0.5990 (2)	0.25730 (5)	0.0216 (3)
H13A	0.3305	0.5695	0.2687	0.032*
H13B	0.2503	0.6380	0.2253	0.032*
H13C	0.2117	0.4971	0.2590	0.032*
C14	0.03479 (13)	0.9957 (2)	0.31621 (6)	0.0251 (3)
H14A	0.0123	0.9012	0.2948	0.038*
H14B	0.0214	1.1063	0.3002	0.038*
H14C	−0.0053	0.9908	0.3421	0.038*
C15	0.09917 (13)	0.9075 (2)	0.46675 (5)	0.0211 (3)
H15A	0.0492	0.8133	0.4694	0.032*
H15B	0.0717	1.0143	0.4783	0.032*
H15C	0.1680	0.8798	0.4849	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0250 (6)	0.0231 (5)	0.0164 (5)	0.0026 (4)	0.0043 (4)	0.0046 (4)
O2	0.0286 (6)	0.0163 (5)	0.0122 (4)	0.0025 (4)	0.0084 (4)	0.0004 (4)
O3	0.0217 (6)	0.0139 (5)	0.0192 (5)	0.0008 (4)	0.0056 (4)	0.0032 (4)
O4	0.0249 (6)	0.0184 (5)	0.0136 (4)	0.0055 (4)	0.0066 (4)	−0.0009 (4)
N1	0.0165 (6)	0.0149 (6)	0.0177 (6)	0.0010 (5)	0.0020 (5)	0.0010 (4)
N2	0.0154 (6)	0.0161 (5)	0.0156 (5)	−0.0003 (5)	0.0034 (4)	0.0004 (4)
C1	0.0116 (6)	0.0168 (6)	0.0136 (6)	−0.0004 (5)	0.0008 (5)	0.0003 (5)
C2	0.0140 (7)	0.0162 (6)	0.0147 (6)	0.0017 (5)	0.0033 (5)	−0.0010 (5)
C3	0.0136 (6)	0.0162 (6)	0.0127 (6)	−0.0020 (5)	0.0044 (5)	−0.0001 (5)
C4	0.0137 (6)	0.0139 (6)	0.0156 (6)	−0.0002 (5)	0.0034 (5)	0.0016 (5)
C5	0.0135 (6)	0.0161 (6)	0.0150 (6)	−0.0009 (5)	0.0038 (5)	−0.0020 (5)
C6	0.0143 (7)	0.0188 (7)	0.0111 (6)	0.0008 (5)	0.0023 (5)	0.0005 (5)
C7	0.0156 (7)	0.0184 (7)	0.0123 (6)	−0.0007 (5)	0.0013 (5)	0.0012 (5)
C8	0.0144 (7)	0.0162 (6)	0.0143 (6)	−0.0007 (5)	0.0008 (5)	0.0014 (5)
C9	0.0144 (7)	0.0171 (6)	0.0160 (6)	−0.0008 (5)	0.0015 (5)	0.0009 (5)
C10	0.0128 (6)	0.0169 (6)	0.0152 (6)	−0.0035 (5)	0.0013 (5)	0.0002 (5)
C11	0.0194 (7)	0.0197 (7)	0.0202 (7)	0.0010 (6)	0.0055 (6)	−0.0027 (5)
C12	0.0224 (8)	0.0151 (7)	0.0249 (7)	0.0038 (6)	0.0027 (6)	0.0042 (5)
C13	0.0263 (8)	0.0249 (7)	0.0140 (6)	0.0075 (6)	0.0045 (6)	−0.0026 (5)
C14	0.0247 (8)	0.0236 (8)	0.0262 (8)	0.0039 (7)	0.0016 (6)	0.0081 (6)
C15	0.0256 (8)	0.0237 (7)	0.0156 (6)	0.0056 (6)	0.0085 (6)	−0.0011 (5)

Geometric parameters (Å, º)

O1—C9	1.2239 (16)	C6—H6	0.9500
O2—C3	1.3669 (15)	C7—C8	1.346 (2)
O2—C13	1.4280 (17)	C7—H7	0.9500
O3—C4	1.3709 (16)	C8—C9	1.4882 (19)
O3—C14	1.422 (2)	C10—C11	1.4822 (19)
O4—C5	1.3630 (16)	C11—H11A	0.9800
O4—C15	1.4274 (16)	C11—H11B	0.9800
N1—C9	1.3810 (18)	C11—H11C	0.9800
N1—C10	1.3912 (17)	C12—H12A	0.9800
N1—C12	1.4563 (19)	C12—H12B	0.9800
N2—C10	1.2982 (18)	C12—H12C	0.9800
N2—C8	1.4104 (17)	C13—H13A	0.9800
C1—C6	1.4033 (19)	C13—H13B	0.9800
C1—C2	1.4065 (18)	C13—H13C	0.9800
C1—C7	1.4575 (19)	C14—H14A	0.9800
C2—C3	1.3879 (19)	C14—H14B	0.9800
C2—H2	0.9500	C14—H14C	0.9800
C3—C4	1.4011 (19)	C15—H15A	0.9800
C4—C5	1.3990 (18)	C15—H15B	0.9800
C5—C6	1.3896 (19)	C15—H15C	0.9800
C3—O2—C13	117.13 (11)	N2—C10—N1	114.27 (12)
C4—O3—C14	113.18 (11)	N2—C10—C11	124.44 (13)
C5—O4—C15	116.44 (11)	N1—C10—C11	121.27 (13)
C9—N1—C10	108.07 (12)	C10—C11—H11A	109.5
C9—N1—C12	123.95 (12)	C10—C11—H11B	109.5
C10—N1—C12	127.97 (12)	H11A—C11—H11B	109.5
C10—N2—C8	105.60 (11)	C10—C11—H11C	109.5
C6—C1—C2	119.98 (13)	H11A—C11—H11C	109.5
C6—C1—C7	117.51 (12)	H11B—C11—H11C	109.5
C2—C1—C7	122.50 (12)	N1—C12—H12A	109.5
C3—C2—C1	119.34 (12)	N1—C12—H12B	109.5
C3—C2—H2	120.3	H12A—C12—H12B	109.5
C1—C2—H2	120.3	N1—C12—H12C	109.5
O2—C3—C2	124.45 (12)	H12A—C12—H12C	109.5
O2—C3—C4	114.69 (12)	H12B—C12—H12C	109.5
C2—C3—C4	120.86 (12)	O2—C13—H13A	109.5
O3—C4—C5	121.02 (12)	O2—C13—H13B	109.5
O3—C4—C3	119.45 (12)	H13A—C13—H13B	109.5
C5—C4—C3	119.49 (12)	O2—C13—H13C	109.5
O4—C5—C6	125.00 (12)	H13A—C13—H13C	109.5
O4—C5—C4	114.81 (12)	H13B—C13—H13C	109.5
C6—C5—C4	120.20 (12)	O3—C14—H14A	109.5
C5—C6—C1	120.05 (12)	O3—C14—H14B	109.5
C5—C6—H6	120.0	H14A—C14—H14B	109.5
C1—C6—H6	120.0	O3—C14—H14C	109.5
C8—C7—C1	128.67 (12)	H14A—C14—H14C	109.5
C8—C7—H7	115.7	H14B—C14—H14C	109.5
C1—C7—H7	115.7	O4—C15—H15A	109.5
C7—C8—N2	128.22 (13)	O4—C15—H15B	109.5
C7—C8—C9	123.02 (12)	H15A—C15—H15B	109.5
N2—C8—C9	108.76 (12)	O4—C15—H15C	109.5
O1—C9—N1	125.81 (13)	H15A—C15—H15C	109.5
O1—C9—C8	130.89 (13)	H15B—C15—H15C	109.5
N1—C9—C8	103.30 (11)
C6—C1—C2—C3	0.6 (2)	C7—C1—C6—C5	176.44 (13)
C7—C1—C2—C3	−178.53 (13)	C6—C1—C7—C8	−174.24 (15)
C13—O2—C3—C2	6.8 (2)	C2—C1—C7—C8	4.9 (2)
C13—O2—C3—C4	−172.82 (13)	C1—C7—C8—N2	−1.7 (3)
C1—C2—C3—O2	−177.55 (13)	C1—C7—C8—C9	177.82 (14)
C1—C2—C3—C4	2.1 (2)	C10—N2—C8—C7	−179.81 (15)
C14—O3—C4—C5	−80.83 (17)	C10—N2—C8—C9	0.62 (16)
C14—O3—C4—C3	101.28 (15)	C10—N1—C9—O1	−179.55 (14)
O2—C3—C4—O3	−4.97 (19)	C12—N1—C9—O1	−0.5 (2)
C2—C3—C4—O3	175.39 (13)	C10—N1—C9—C8	−0.34 (15)
O2—C3—C4—C5	177.11 (13)	C12—N1—C9—C8	178.74 (13)
C2—C3—C4—C5	−2.5 (2)	C7—C8—C9—O1	−0.6 (3)
C15—O4—C5—C6	2.2 (2)	N2—C8—C9—O1	179.00 (15)
C15—O4—C5—C4	−177.74 (13)	C7—C8—C9—N1	−179.76 (14)
O3—C4—C5—O4	2.4 (2)	N2—C8—C9—N1	−0.16 (15)
C3—C4—C5—O4	−179.71 (13)	C8—N2—C10—N1	−0.89 (16)
O3—C4—C5—C6	−177.52 (13)	C8—N2—C10—C11	177.71 (13)
C3—C4—C5—C6	0.4 (2)	C9—N1—C10—N2	0.81 (17)
O4—C5—C6—C1	−177.69 (13)	C12—N1—C10—N2	−178.22 (14)
C4—C5—C6—C1	2.2 (2)	C9—N1—C10—C11	−177.84 (13)
C2—C1—C6—C5	−2.7 (2)	C12—N1—C10—C11	3.1 (2)

(Form_II)

Crystal data

C15H18N2O4	F(000) = 616
Mr = 290.31	Dx = 1.364 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.3324 (9) Å	Cell parameters from 6892 reflections
b = 29.277 (3) Å	θ = 2.8–26.3°
c = 7.4171 (8) Å	µ = 0.10 mm^−1
β = 117.402 (4)°	T = 100 K
V = 1413.6 (3) Å^3	BLOCK, yellow
Z = 4	0.12 × 0.09 × 0.06 mm

Data collection

Bruker D8 VENTURE Kappa Duo PHOTON II CPAD diffractometer	2775 independent reflections
Radiation source: micro-focus sealed tube, Incoatech IµS HB	2269 reflections with I > 2σ(I)
Multilayer mirrors monochromator	Rint = 0.120
Detector resolution: 7.39 pixels mm^-1	θmax = 26.0°, θmin = 2.8°
φ and ω scans	h = −9→9
Absorption correction: multi-scan SADABS (Bruker, 2006)	k = −36→36
Tmin = 0.988, Tmax = 0.994	l = −9→9
39409 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.076	H-atom parameters constrained
wR(F^2) = 0.150	w = 1/[σ^2(Fo^2) + (0.0397P)^2 + 2.4518P] where P = (Fo^2 + 2Fc^2)/3
S = 1.18	(Δ/σ)max < 0.001
2775 reflections	Δρmax = 0.30 e Å^−3
195 parameters	Δρmin = −0.30 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
O1	0.2776 (3)	0.97789 (7)	0.1814 (3)	0.0186 (5)
O2	0.4041 (3)	0.78732 (6)	0.9653 (3)	0.0164 (5)
O3	0.6050 (3)	0.83479 (7)	1.3062 (3)	0.0157 (5)
O4	0.7304 (3)	0.92033 (7)	1.3028 (3)	0.0163 (5)
N1	0.1011 (4)	0.91167 (8)	0.0296 (4)	0.0135 (5)
N2	0.1777 (4)	0.86602 (8)	0.2997 (3)	0.0120 (5)
C1	0.4568 (4)	0.89725 (10)	0.7512 (4)	0.0120 (6)
C2	0.3988 (4)	0.85204 (9)	0.7562 (4)	0.0125 (6)
H2	0.3233	0.8356	0.6335	0.015*
C3	0.4525 (4)	0.83141 (10)	0.9420 (4)	0.0137 (6)
C4	0.5632 (5)	0.85506 (10)	1.1242 (4)	0.0129 (6)
C5	0.6223 (4)	0.89994 (10)	1.1184 (4)	0.0133 (6)
C6	0.5726 (4)	0.92118 (10)	0.9329 (4)	0.0145 (6)
H6	0.6166	0.9515	0.9296	0.017*
C7	0.3998 (4)	0.92200 (10)	0.5615 (4)	0.0133 (6)
H7	0.4569	0.9517	0.5756	0.016*
C8	0.2775 (4)	0.90843 (9)	0.3696 (4)	0.0127 (6)
C9	0.2272 (4)	0.93860 (10)	0.1917 (4)	0.0136 (6)
C10	0.0802 (4)	0.86950 (10)	0.1043 (4)	0.0125 (6)
C11	−0.0413 (5)	0.83238 (10)	−0.0353 (4)	0.0157 (6)
H11A	−0.0442	0.8059	0.0440	0.024*
H11B	0.0219	0.8237	−0.1215	0.024*
H11C	−0.1819	0.8430	−0.1208	0.024*
C12	0.0069 (5)	0.92687 (11)	−0.1820 (4)	0.0168 (7)
H12A	0.1125	0.9291	−0.2277	0.025*
H12B	−0.0569	0.9568	−0.1930	0.025*
H12C	−0.0981	0.9048	−0.2670	0.025*
C13	0.3216 (5)	0.75888 (10)	0.7895 (5)	0.0214 (7)
H13A	0.4117	0.7598	0.7247	0.032*
H13B	0.1845	0.7699	0.6937	0.032*
H13C	0.3117	0.7274	0.8291	0.032*
C14	0.7874 (5)	0.80786 (12)	1.3884 (5)	0.0251 (8)
H14A	0.9059	0.8274	1.4161	0.038*
H14B	0.7763	0.7841	1.2907	0.038*
H14C	0.8055	0.7935	1.5150	0.038*
C15	0.7793 (5)	0.96752 (10)	1.3016 (5)	0.0186 (7)
H15A	0.6538	0.9846	1.2167	0.028*
H15B	0.8773	0.9709	1.2468	0.028*
H15C	0.8404	0.9795	1.4406	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0210 (12)	0.0135 (11)	0.0186 (11)	−0.0002 (9)	0.0068 (9)	0.0043 (9)
O2	0.0258 (12)	0.0092 (10)	0.0138 (10)	−0.0050 (9)	0.0087 (9)	−0.0023 (8)
O3	0.0217 (12)	0.0153 (11)	0.0114 (10)	−0.0002 (9)	0.0087 (9)	0.0010 (8)
O4	0.0216 (12)	0.0099 (10)	0.0125 (10)	−0.0033 (9)	0.0035 (9)	−0.0019 (8)
N1	0.0146 (13)	0.0133 (12)	0.0116 (12)	0.0021 (10)	0.0052 (10)	0.0027 (10)
N2	0.0099 (12)	0.0102 (12)	0.0132 (13)	0.0012 (10)	0.0031 (10)	0.0015 (10)
C1	0.0084 (14)	0.0123 (14)	0.0134 (14)	0.0047 (11)	0.0035 (12)	0.0021 (11)
C2	0.0121 (15)	0.0110 (14)	0.0124 (14)	0.0003 (11)	0.0038 (12)	−0.0027 (11)
C3	0.0115 (15)	0.0115 (14)	0.0187 (15)	−0.0012 (11)	0.0073 (12)	−0.0014 (12)
C4	0.0143 (15)	0.0149 (15)	0.0111 (14)	0.0026 (12)	0.0074 (12)	0.0032 (11)
C5	0.0119 (15)	0.0141 (14)	0.0133 (14)	−0.0008 (12)	0.0053 (12)	−0.0023 (12)
C6	0.0118 (15)	0.0105 (14)	0.0215 (16)	0.0018 (12)	0.0079 (13)	0.0009 (12)
C7	0.0117 (15)	0.0097 (13)	0.0198 (15)	0.0019 (11)	0.0084 (13)	0.0024 (12)
C8	0.0123 (15)	0.0118 (14)	0.0153 (15)	0.0016 (11)	0.0075 (12)	0.0013 (11)
C9	0.0109 (15)	0.0119 (14)	0.0191 (15)	0.0021 (12)	0.0079 (13)	0.0007 (12)
C10	0.0113 (14)	0.0109 (14)	0.0167 (15)	0.0029 (11)	0.0075 (12)	0.0005 (11)
C11	0.0145 (16)	0.0151 (15)	0.0143 (15)	0.0010 (12)	0.0038 (12)	−0.0007 (12)
C12	0.0179 (16)	0.0204 (16)	0.0116 (15)	0.0009 (13)	0.0064 (13)	0.0046 (12)
C13	0.0315 (19)	0.0119 (15)	0.0140 (15)	−0.0001 (13)	0.0047 (14)	−0.0027 (12)
C14	0.0216 (18)	0.0294 (19)	0.0195 (17)	0.0060 (14)	0.0053 (14)	0.0118 (14)
C15	0.0221 (17)	0.0124 (15)	0.0160 (15)	−0.0050 (13)	0.0043 (13)	−0.0026 (12)

Geometric parameters (Å, º)

O1—C9	1.221 (4)	N2—C8	1.413 (4)
O2—C3	1.371 (3)	C1—C2	1.396 (4)
O2—C13	1.426 (3)	C1—C6	1.405 (4)
O3—C4	1.374 (3)	C1—C7	1.462 (4)
O3—C14	1.425 (4)	C2—C3	1.386 (4)
O4—C5	1.363 (3)	C3—C4	1.398 (4)
O4—C15	1.428 (3)	C4—C5	1.390 (4)
N1—C9	1.378 (4)	C5—C6	1.396 (4)
N1—C10	1.390 (4)	C7—C8	1.347 (4)
N1—C12	1.463 (4)	C8—C9	1.486 (4)
N2—C10	1.292 (4)	C10—C11	1.482 (4)
C3—O2—C13	117.4 (2)	C5—C4—C3	119.3 (3)
C4—O3—C14	113.6 (2)	O4—C5—C4	115.4 (3)
C5—O4—C15	116.7 (2)	O4—C5—C6	124.1 (3)
C9—N1—C10	108.3 (2)	C4—C5—C6	120.5 (3)
C9—N1—C12	123.9 (2)	C5—C6—C1	119.4 (3)
C10—N1—C12	127.8 (2)	C8—C7—C1	128.9 (3)
C10—N2—C8	105.6 (2)	C7—C8—N2	128.9 (3)
C2—C1—C6	120.3 (3)	C7—C8—C9	122.4 (3)
C2—C1—C7	122.7 (3)	N2—C8—C9	108.7 (2)
C6—C1—C7	117.1 (3)	O1—C9—N1	125.8 (3)
C3—C2—C1	119.3 (3)	O1—C9—C8	131.0 (3)
O2—C3—C2	124.4 (3)	N1—C9—C8	103.1 (2)
O2—C3—C4	114.4 (2)	N2—C10—N1	114.3 (3)
C2—C3—C4	121.2 (3)	N2—C10—C11	124.8 (3)
O3—C4—C5	120.5 (3)	N1—C10—C11	120.9 (3)
O3—C4—C3	120.2 (3)
C6—C1—C2—C3	1.4 (4)	C7—C1—C6—C5	176.8 (3)
C7—C1—C2—C3	−177.7 (3)	C2—C1—C7—C8	5.0 (5)
C13—O2—C3—C2	10.1 (4)	C6—C1—C7—C8	−174.2 (3)
C13—O2—C3—C4	−170.0 (3)	C1—C7—C8—N2	−2.6 (5)
C1—C2—C3—O2	−179.9 (3)	C1—C7—C8—C9	177.4 (3)
C1—C2—C3—C4	0.1 (4)	C10—N2—C8—C7	−179.5 (3)
C14—O3—C4—C5	−96.5 (3)	C10—N2—C8—C9	0.5 (3)
C14—O3—C4—C3	86.5 (3)	C10—N1—C9—O1	−179.6 (3)
O2—C3—C4—O3	−3.6 (4)	C12—N1—C9—O1	−0.4 (5)
C2—C3—C4—O3	176.4 (3)	C10—N1—C9—C8	−0.5 (3)
O2—C3—C4—C5	179.3 (3)	C12—N1—C9—C8	178.8 (3)
C2—C3—C4—C5	−0.7 (4)	C7—C8—C9—O1	−0.9 (5)
C15—O4—C5—C4	−175.2 (3)	N2—C8—C9—O1	179.1 (3)
C15—O4—C5—C6	5.4 (4)	C7—C8—C9—N1	−180.0 (3)
O3—C4—C5—O4	3.2 (4)	N2—C8—C9—N1	0.0 (3)
C3—C4—C5—O4	−179.7 (3)	C8—N2—C10—N1	−0.8 (3)
O3—C4—C5—C6	−177.4 (3)	C8—N2—C10—C11	177.7 (3)
C3—C4—C5—C6	−0.3 (4)	C9—N1—C10—N2	0.8 (3)
O4—C5—C6—C1	−178.8 (3)	C12—N1—C10—N2	−178.4 (3)
C4—C5—C6—C1	1.8 (4)	C9—N1—C10—C11	−177.7 (3)
C2—C1—C6—C5	−2.4 (4)	C12—N1—C10—C11	3.1 (4)

(Form_III)

Crystal data

C15H18N2O4	Z = 2
Mr = 290.31	F(000) = 308
Triclinic, P1	Dx = 1.391 Mg m^−3
a = 7.1190 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.2678 (3) Å	Cell parameters from 9906 reflections
c = 15.0171 (6) Å	θ = 3.2–37.1°
α = 78.012 (1)°	µ = 0.10 mm^−1
β = 82.182 (1)°	T = 100 K
γ = 66.007 (1)°	PLATE, yellow
V = 693.20 (4) Å^3	0.12 × 0.08 × 0.04 mm

Data collection

Bruker D8 VENTURE Kappa Duo PHOTON II CPAD diffractometer	4011 independent reflections
Radiation source: micro-focus sealed tube, Incoatech IµS HB	3461 reflections with I > 2σ(I)
Multilayer mirrors monochromator	Rint = 0.039
Detector resolution: 7.39 pixels mm^-1	θmax = 30.0°, θmin = 3.2°
φ and ω scans	h = −8→10
Absorption correction: multi-scan SADABS (Bruker, 2006)	k = −10→10
Tmin = 0.988, Tmax = 0.996	l = −21→21
22228 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.112	w = 1/[σ^2(Fo^2) + (0.0586P)^2 + 0.2144P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
4011 reflections	Δρmax = 0.48 e Å^−3
195 parameters	Δρmin = −0.30 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
O1	0.81963 (12)	0.29469 (13)	0.95650 (5)	0.01747 (17)
O2	0.06520 (11)	0.58906 (12)	0.57070 (5)	0.01501 (17)
O3	−0.28911 (11)	0.74708 (12)	0.66698 (5)	0.01531 (17)
O4	−0.29726 (11)	0.79718 (12)	0.83926 (5)	0.01540 (17)
N1	0.98824 (13)	0.17433 (14)	0.82395 (6)	0.01343 (18)
N2	0.72544 (13)	0.28964 (14)	0.73082 (6)	0.01298 (18)
C1	0.26486 (15)	0.54624 (15)	0.79181 (7)	0.01134 (19)
C2	0.26745 (15)	0.52784 (15)	0.70045 (7)	0.01201 (19)
H2	0.3943	0.4674	0.6673	0.014*
C3	0.08186 (15)	0.59920 (15)	0.65902 (7)	0.01180 (19)
C4	−0.10695 (15)	0.68780 (15)	0.70721 (7)	0.01173 (19)
C5	−0.10799 (15)	0.70804 (15)	0.79790 (7)	0.01152 (19)
C6	0.07724 (15)	0.63842 (15)	0.84014 (7)	0.01192 (19)
H6	0.0763	0.6534	0.9016	0.014*
C7	0.45142 (15)	0.46688 (15)	0.84168 (7)	0.01204 (19)
H7	0.4329	0.4991	0.9013	0.014*
C8	0.64674 (15)	0.35400 (15)	0.81513 (7)	0.01175 (19)
C9	0.81888 (15)	0.27775 (16)	0.87709 (7)	0.01271 (19)
C10	0.92215 (16)	0.18899 (15)	0.73883 (7)	0.01233 (19)
C11	1.07177 (16)	0.09910 (17)	0.66514 (8)	0.0165 (2)
H11A	0.9980	0.1194	0.6110	0.025*
H11B	1.1464	−0.0475	0.6858	0.025*
H11C	1.1697	0.1660	0.6499	0.025*
C12	1.19573 (16)	0.06867 (17)	0.85576 (8)	0.0173 (2)
H12A	1.2480	0.1690	0.8643	0.026*
H12B	1.2857	−0.0124	0.8105	0.026*
H12C	1.1932	−0.0218	0.9138	0.026*
C13	0.25332 (16)	0.51777 (18)	0.51663 (7)	0.0159 (2)
H13A	0.3259	0.6084	0.5136	0.024*
H13B	0.2233	0.5170	0.4550	0.024*
H13C	0.3400	0.3789	0.5442	0.024*
C14	−0.34953 (17)	0.94381 (18)	0.61103 (8)	0.0212 (2)
H14A	−0.3678	1.0465	0.6482	0.032*
H14B	−0.4796	0.9765	0.5841	0.032*
H14C	−0.2427	0.9436	0.5624	0.032*
C15	−0.30221 (17)	0.80397 (18)	0.93380 (7)	0.0178 (2)
H15A	−0.2275	0.6663	0.9666	0.027*
H15B	−0.4455	0.8555	0.9583	0.027*
H15C	−0.2370	0.8948	0.9415	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0176 (4)	0.0206 (4)	0.0134 (4)	−0.0052 (3)	−0.0047 (3)	−0.0032 (3)
O2	0.0113 (3)	0.0225 (4)	0.0106 (3)	−0.0045 (3)	−0.0009 (3)	−0.0057 (3)
O3	0.0109 (3)	0.0185 (4)	0.0161 (4)	−0.0052 (3)	−0.0042 (3)	−0.0012 (3)
O4	0.0104 (3)	0.0203 (4)	0.0126 (3)	−0.0023 (3)	0.0007 (3)	−0.0051 (3)
N1	0.0110 (4)	0.0134 (4)	0.0144 (4)	−0.0028 (3)	−0.0033 (3)	−0.0016 (3)
N2	0.0130 (4)	0.0131 (4)	0.0114 (4)	−0.0034 (3)	−0.0010 (3)	−0.0025 (3)
C1	0.0115 (4)	0.0103 (4)	0.0118 (4)	−0.0038 (3)	−0.0020 (3)	−0.0010 (3)
C2	0.0106 (4)	0.0121 (4)	0.0119 (4)	−0.0027 (3)	−0.0011 (3)	−0.0024 (3)
C3	0.0124 (4)	0.0118 (4)	0.0109 (4)	−0.0040 (4)	−0.0015 (3)	−0.0023 (3)
C4	0.0100 (4)	0.0121 (4)	0.0126 (4)	−0.0040 (3)	−0.0024 (3)	−0.0007 (4)
C5	0.0104 (4)	0.0103 (4)	0.0127 (4)	−0.0032 (3)	0.0005 (3)	−0.0018 (3)
C6	0.0121 (4)	0.0117 (4)	0.0113 (4)	−0.0038 (4)	−0.0016 (3)	−0.0016 (3)
C7	0.0128 (4)	0.0122 (5)	0.0111 (4)	−0.0048 (4)	−0.0023 (3)	−0.0009 (3)
C8	0.0125 (4)	0.0117 (4)	0.0108 (4)	−0.0044 (4)	−0.0031 (3)	−0.0004 (3)
C9	0.0126 (4)	0.0117 (4)	0.0133 (4)	−0.0045 (4)	−0.0030 (3)	−0.0002 (4)
C10	0.0146 (4)	0.0099 (4)	0.0123 (4)	−0.0051 (4)	−0.0025 (3)	0.0003 (3)
C11	0.0151 (4)	0.0154 (5)	0.0170 (5)	−0.0042 (4)	0.0012 (4)	−0.0031 (4)
C12	0.0114 (4)	0.0164 (5)	0.0219 (5)	−0.0024 (4)	−0.0059 (4)	−0.0017 (4)
C13	0.0127 (4)	0.0207 (5)	0.0124 (5)	−0.0046 (4)	0.0010 (4)	−0.0040 (4)
C14	0.0175 (5)	0.0199 (6)	0.0213 (5)	−0.0020 (4)	−0.0085 (4)	0.0003 (4)
C15	0.0159 (5)	0.0214 (5)	0.0132 (5)	−0.0037 (4)	0.0021 (4)	−0.0065 (4)

Geometric parameters (Å, º)

O1—C9	1.2250 (12)	C6—H6	0.9500
O2—C3	1.3672 (12)	C7—C8	1.3501 (14)
O2—C13	1.4268 (12)	C7—H7	0.9500
O3—C4	1.3722 (11)	C8—C9	1.4894 (13)
O3—C14	1.4263 (14)	C10—C11	1.4832 (14)
O4—C5	1.3603 (12)	C11—H11A	0.9800
O4—C15	1.4259 (13)	C11—H11B	0.9800
N1—C9	1.3806 (13)	C11—H11C	0.9800
N1—C10	1.3902 (13)	C12—H12A	0.9800
N1—C12	1.4550 (13)	C12—H12B	0.9800
N2—C10	1.2988 (13)	C12—H12C	0.9800
N2—C8	1.4056 (13)	C13—H13A	0.9800
C1—C2	1.4028 (13)	C13—H13B	0.9800
C1—C6	1.4036 (13)	C13—H13C	0.9800
C1—C7	1.4580 (13)	C14—H14A	0.9800
C2—C3	1.3906 (13)	C14—H14B	0.9800
C2—H2	0.9500	C14—H14C	0.9800
C3—C4	1.4036 (13)	C15—H15A	0.9800
C4—C5	1.3986 (14)	C15—H15B	0.9800
C5—C6	1.3960 (13)	C15—H15C	0.9800
C3—O2—C13	116.41 (8)	N2—C10—N1	114.35 (9)
C4—O3—C14	113.52 (8)	N2—C10—C11	125.04 (9)
C5—O4—C15	116.29 (8)	N1—C10—C11	120.59 (9)
C9—N1—C10	107.97 (8)	C10—C11—H11A	109.5
C9—N1—C12	123.88 (9)	C10—C11—H11B	109.5
C10—N1—C12	128.15 (9)	H11A—C11—H11B	109.5
C10—N2—C8	105.57 (8)	C10—C11—H11C	109.5
C2—C1—C6	120.26 (9)	H11A—C11—H11C	109.5
C2—C1—C7	122.70 (9)	H11B—C11—H11C	109.5
C6—C1—C7	117.01 (9)	N1—C12—H12A	109.5
C3—C2—C1	119.14 (9)	N1—C12—H12B	109.5
C3—C2—H2	120.4	H12A—C12—H12B	109.5
C1—C2—H2	120.4	N1—C12—H12C	109.5
O2—C3—C2	124.37 (9)	H12A—C12—H12C	109.5
O2—C3—C4	114.51 (8)	H12B—C12—H12C	109.5
C2—C3—C4	121.11 (9)	O2—C13—H13A	109.5
O3—C4—C5	120.18 (9)	O2—C13—H13B	109.5
O3—C4—C3	120.41 (9)	H13A—C13—H13B	109.5
C5—C4—C3	119.36 (9)	O2—C13—H13C	109.5
O4—C5—C6	124.33 (9)	H13A—C13—H13C	109.5
O4—C5—C4	115.55 (9)	H13B—C13—H13C	109.5
C6—C5—C4	120.13 (9)	O3—C14—H14A	109.5
C5—C6—C1	119.97 (9)	O3—C14—H14B	109.5
C5—C6—H6	120.0	H14A—C14—H14B	109.5
C1—C6—H6	120.0	O3—C14—H14C	109.5
C8—C7—C1	129.11 (9)	H14A—C14—H14C	109.5
C8—C7—H7	115.4	H14B—C14—H14C	109.5
C1—C7—H7	115.4	O4—C15—H15A	109.5
C7—C8—N2	129.26 (9)	O4—C15—H15B	109.5
C7—C8—C9	121.89 (9)	H15A—C15—H15B	109.5
N2—C8—C9	108.85 (8)	O4—C15—H15C	109.5
O1—C9—N1	125.86 (9)	H15A—C15—H15C	109.5
O1—C9—C8	130.88 (9)	H15B—C15—H15C	109.5
N1—C9—C8	103.25 (8)
C6—C1—C2—C3	−0.98 (15)	C7—C1—C6—C5	−176.66 (9)
C7—C1—C2—C3	177.02 (9)	C2—C1—C7—C8	−5.68 (17)
C13—O2—C3—C2	−6.18 (15)	C6—C1—C7—C8	172.37 (10)
C13—O2—C3—C4	174.34 (9)	C1—C7—C8—N2	3.15 (19)
C1—C2—C3—O2	−179.81 (9)	C1—C7—C8—C9	−177.26 (10)
C1—C2—C3—C4	−0.36 (16)	C10—N2—C8—C7	178.72 (11)
C14—O3—C4—C5	99.49 (11)	C10—N2—C8—C9	−0.91 (11)
C14—O3—C4—C3	−82.97 (12)	C10—N1—C9—O1	179.24 (10)
O2—C3—C4—O3	3.15 (14)	C12—N1—C9—O1	0.04 (17)
C2—C3—C4—O3	−176.35 (9)	C10—N1—C9—C8	0.19 (11)
O2—C3—C4—C5	−179.28 (9)	C12—N1—C9—C8	−179.01 (9)
C2—C3—C4—C5	1.22 (16)	C7—C8—C9—O1	1.79 (18)
C15—O4—C5—C6	−4.80 (15)	N2—C8—C9—O1	−178.55 (11)
C15—O4—C5—C4	175.05 (9)	C7—C8—C9—N1	−179.23 (10)
O3—C4—C5—O4	−3.02 (14)	N2—C8—C9—N1	0.43 (11)
C3—C4—C5—O4	179.41 (9)	C8—N2—C10—N1	1.09 (12)
O3—C4—C5—C6	176.84 (9)	C8—N2—C10—C11	−177.23 (10)
C3—C4—C5—C6	−0.74 (15)	C9—N1—C10—N2	−0.84 (13)
O4—C5—C6—C1	179.27 (9)	C12—N1—C10—N2	178.31 (10)
C4—C5—C6—C1	−0.58 (15)	C9—N1—C10—C11	177.57 (9)
C2—C1—C6—C5	1.45 (15)	C12—N1—C10—C11	−3.28 (16)

(Form_IV)

Crystal data

C15H18N2O4	F(000) = 616
Mr = 290.31	Dx = 1.363 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.3901 (5) Å	Cell parameters from 9889 reflections
b = 25.1748 (18) Å	θ = 2.8–34.2°
c = 8.0438 (6) Å	µ = 0.10 mm^−1
β = 108.992 (3)°	T = 100 K
V = 1415.04 (18) Å^3	PLATE, yellow
Z = 4	0.12 × 0.09 × 0.04 mm

Data collection

Bruker D8 VENTURE Kappa Duo PHOTON II CPAD diffractometer	3416 independent reflections
Radiation source: micro-focus sealed tube, Incoatech IµS HB	3144 reflections with I > 2σ(I)
Multilayer mirrors monochromator	Rint = 0.066
Detector resolution: 7.39 pixels mm^-1	θmax = 28.0°, θmin = 2.8°
φ and ω scans	h = −9→9
Absorption correction: multi-scan SADABS (Bruker, 2006)	k = −33→33
Tmin = 0.988, Tmax = 0.996	l = −10→10
39710 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.124	w = 1/[σ^2(Fo^2) + (0.0389P)^2 + 1.3482P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max < 0.001
3416 reflections	Δρmax = 0.39 e Å^−3
195 parameters	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
O4	0.18263 (17)	0.70119 (5)	0.18927 (16)	0.0208 (3)
O3	0.56109 (18)	0.72390 (5)	0.28392 (16)	0.0180 (3)
O2	0.81817 (16)	0.66805 (5)	0.52338 (15)	0.0175 (3)
O1	0.15837 (17)	0.45183 (5)	0.71735 (16)	0.0196 (3)
N2	0.61798 (19)	0.50668 (5)	0.77611 (17)	0.0142 (3)
N1	0.4796 (2)	0.43858 (5)	0.87184 (18)	0.0154 (3)
C1	0.3835 (2)	0.59312 (6)	0.5082 (2)	0.0132 (3)
C6	0.2458 (2)	0.62511 (6)	0.3885 (2)	0.0146 (3)
H6	0.1137	0.6167	0.3582	0.018*
C5	0.3038 (2)	0.66923 (6)	0.3144 (2)	0.0155 (3)
C4	0.4974 (2)	0.68241 (6)	0.3614 (2)	0.0143 (3)
C3	0.6334 (2)	0.65101 (6)	0.4838 (2)	0.0133 (3)
C2	0.5780 (2)	0.60630 (6)	0.5563 (2)	0.0133 (3)
H2	0.6712	0.5848	0.6378	0.016*
C7	0.3157 (2)	0.54613 (6)	0.5767 (2)	0.0133 (3)
H7	0.1814	0.5403	0.5336	0.016*
C8	0.4180 (2)	0.50979 (6)	0.6930 (2)	0.0136 (3)
C9	0.3255 (2)	0.46459 (6)	0.7537 (2)	0.0141 (3)
C10	0.6463 (2)	0.46478 (6)	0.8755 (2)	0.0142 (3)
C11	0.8379 (2)	0.44501 (7)	0.9846 (2)	0.0185 (3)
H11A	0.9348	0.4575	0.9347	0.028*
H11B	0.8371	0.4061	0.9861	0.028*
H11C	0.8679	0.4584	1.1049	0.028*
C12	0.4581 (3)	0.39235 (7)	0.9717 (2)	0.0195 (3)
H12A	0.3919	0.4026	1.0544	0.029*
H12B	0.5847	0.3780	1.0369	0.029*
H12C	0.3831	0.3652	0.8911	0.029*
C15	−0.0166 (3)	0.69738 (8)	0.1644 (3)	0.0299 (4)
H13A	−0.0639	0.6625	0.1151	0.045*
H13B	−0.0853	0.7253	0.0833	0.045*
H13C	−0.0379	0.7018	0.2777	0.045*
C14	0.5027 (3)	0.77537 (7)	0.3205 (2)	0.0228 (4)
H14A	0.3714	0.7822	0.2440	0.034*
H14B	0.5885	0.8022	0.2988	0.034*
H14C	0.5081	0.7771	0.4437	0.034*
C13	0.9569 (2)	0.64053 (8)	0.6620 (2)	0.0230 (4)
H15A	0.9219	0.6427	0.7693	0.034*
H15B	1.0829	0.6568	0.6829	0.034*
H15C	0.9613	0.6032	0.6290	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0180 (6)	0.0207 (6)	0.0215 (6)	0.0022 (5)	0.0035 (5)	0.0107 (5)
O3	0.0268 (6)	0.0110 (5)	0.0206 (6)	−0.0003 (5)	0.0137 (5)	0.0034 (4)
O2	0.0154 (6)	0.0171 (6)	0.0194 (6)	−0.0022 (4)	0.0046 (5)	0.0044 (5)
O1	0.0186 (6)	0.0180 (6)	0.0227 (6)	−0.0031 (5)	0.0075 (5)	0.0012 (5)
N2	0.0184 (7)	0.0113 (6)	0.0134 (6)	0.0010 (5)	0.0058 (5)	−0.0003 (5)
N1	0.0215 (7)	0.0114 (6)	0.0139 (6)	−0.0010 (5)	0.0068 (5)	0.0016 (5)
C1	0.0180 (7)	0.0105 (7)	0.0125 (7)	0.0006 (6)	0.0068 (6)	−0.0006 (5)
C6	0.0160 (7)	0.0138 (7)	0.0144 (7)	−0.0003 (6)	0.0055 (6)	−0.0005 (6)
C5	0.0199 (8)	0.0132 (7)	0.0133 (7)	0.0034 (6)	0.0054 (6)	0.0014 (6)
C4	0.0228 (8)	0.0094 (7)	0.0136 (7)	0.0000 (6)	0.0098 (6)	0.0006 (5)
C3	0.0166 (7)	0.0118 (7)	0.0129 (7)	−0.0003 (6)	0.0068 (6)	−0.0019 (6)
C2	0.0179 (8)	0.0107 (7)	0.0118 (7)	0.0017 (5)	0.0054 (6)	0.0006 (5)
C7	0.0164 (7)	0.0109 (7)	0.0143 (7)	−0.0010 (5)	0.0073 (6)	−0.0005 (6)
C8	0.0177 (8)	0.0112 (7)	0.0135 (7)	−0.0013 (6)	0.0075 (6)	−0.0017 (6)
C9	0.0207 (8)	0.0104 (7)	0.0131 (7)	−0.0008 (6)	0.0079 (6)	−0.0006 (6)
C10	0.0200 (8)	0.0117 (7)	0.0126 (7)	−0.0004 (6)	0.0076 (6)	−0.0018 (6)
C11	0.0214 (8)	0.0159 (8)	0.0167 (8)	0.0015 (6)	0.0043 (6)	0.0011 (6)
C12	0.0277 (9)	0.0130 (7)	0.0190 (8)	−0.0024 (6)	0.0090 (7)	0.0037 (6)
C15	0.0203 (9)	0.0313 (10)	0.0363 (11)	0.0065 (7)	0.0071 (8)	0.0163 (9)
C14	0.0315 (10)	0.0112 (7)	0.0284 (9)	−0.0018 (7)	0.0132 (8)	−0.0007 (7)
C13	0.0157 (8)	0.0286 (9)	0.0230 (9)	0.0016 (7)	0.0039 (7)	0.0071 (7)

Geometric parameters (Å, º)

O4—C5	1.3693 (19)	C2—H2	0.9500
O4—C15	1.423 (2)	C7—C8	1.351 (2)
O3—C4	1.3753 (18)	C7—H7	0.9500
O3—C14	1.426 (2)	C8—C9	1.489 (2)
O2—C3	1.3660 (19)	C10—C11	1.488 (2)
O2—C13	1.425 (2)	C11—H11A	0.9800
O1—C9	1.216 (2)	C11—H11B	0.9800
N2—C10	1.299 (2)	C11—H11C	0.9800
N2—C8	1.412 (2)	C12—H12A	0.9800
N1—C9	1.387 (2)	C12—H12B	0.9800
N1—C10	1.389 (2)	C12—H12C	0.9800
N1—C12	1.452 (2)	C15—H13A	0.9800
C1—C2	1.401 (2)	C15—H13B	0.9800
C1—C6	1.405 (2)	C15—H13C	0.9800
C1—C7	1.461 (2)	C14—H14A	0.9800
C6—C5	1.392 (2)	C14—H14B	0.9800
C6—H6	0.9500	C14—H14C	0.9800
C5—C4	1.396 (2)	C13—H15A	0.9800
C4—C3	1.400 (2)	C13—H15B	0.9800
C3—C2	1.389 (2)	C13—H15C	0.9800
C5—O4—C15	117.58 (13)	N2—C10—N1	114.11 (14)
C4—O3—C14	115.20 (12)	N2—C10—C11	124.51 (15)
C3—O2—C13	116.10 (13)	N1—C10—C11	121.38 (14)
C10—N2—C8	105.70 (13)	C10—C11—H11A	109.5
C9—N1—C10	108.37 (13)	C10—C11—H11B	109.5
C9—N1—C12	122.94 (14)	H11A—C11—H11B	109.5
C10—N1—C12	128.69 (14)	C10—C11—H11C	109.5
C2—C1—C6	120.14 (14)	H11A—C11—H11C	109.5
C2—C1—C7	122.35 (14)	H11B—C11—H11C	109.5
C6—C1—C7	117.51 (14)	N1—C12—H12A	109.5
C5—C6—C1	119.72 (15)	N1—C12—H12B	109.5
C5—C6—H6	120.1	H12A—C12—H12B	109.5
C1—C6—H6	120.1	N1—C12—H12C	109.5
O4—C5—C6	124.37 (15)	H12A—C12—H12C	109.5
O4—C5—C4	115.27 (14)	H12B—C12—H12C	109.5
C6—C5—C4	120.32 (15)	O4—C15—H13A	109.5
O3—C4—C5	121.98 (14)	O4—C15—H13B	109.5
O3—C4—C3	118.30 (14)	H13A—C15—H13B	109.5
C5—C4—C3	119.63 (14)	O4—C15—H13C	109.5
O2—C3—C2	124.44 (14)	H13A—C15—H13C	109.5
O2—C3—C4	114.90 (14)	H13B—C15—H13C	109.5
C2—C3—C4	120.66 (15)	O3—C14—H14A	109.5
C3—C2—C1	119.50 (14)	O3—C14—H14B	109.5
C3—C2—H2	120.2	H14A—C14—H14B	109.5
C1—C2—H2	120.2	O3—C14—H14C	109.5
C8—C7—C1	128.76 (15)	H14A—C14—H14C	109.5
C8—C7—H7	115.6	H14B—C14—H14C	109.5
C1—C7—H7	115.6	O2—C13—H15A	109.5
C7—C8—N2	129.02 (14)	O2—C13—H15B	109.5
C7—C8—C9	122.09 (15)	H15A—C13—H15B	109.5
N2—C8—C9	108.89 (13)	O2—C13—H15C	109.5
O1—C9—N1	125.70 (14)	H15A—C13—H15C	109.5
O1—C9—C8	131.41 (15)	H15B—C13—H15C	109.5
N1—C9—C8	102.89 (13)
C2—C1—C6—C5	1.6 (2)	C7—C1—C2—C3	178.76 (14)
C7—C1—C6—C5	−177.58 (14)	C2—C1—C7—C8	1.5 (3)
C15—O4—C5—C6	16.0 (2)	C6—C1—C7—C8	−179.35 (16)
C15—O4—C5—C4	−166.35 (16)	C1—C7—C8—N2	−1.8 (3)
C1—C6—C5—O4	176.16 (15)	C1—C7—C8—C9	178.17 (14)
C1—C6—C5—C4	−1.4 (2)	C10—N2—C8—C7	−179.88 (16)
C14—O3—C4—C5	66.5 (2)	C10—N2—C8—C9	0.16 (16)
C14—O3—C4—C3	−117.04 (16)	C10—N1—C9—O1	179.31 (15)
O4—C5—C4—O3	−1.4 (2)	C12—N1—C9—O1	−1.4 (2)
C6—C5—C4—O3	176.36 (14)	C10—N1—C9—C8	−1.86 (16)
O4—C5—C4—C3	−177.80 (14)	C12—N1—C9—C8	177.39 (14)
C6—C5—C4—C3	0.0 (2)	C7—C8—C9—O1	−0.1 (3)
C13—O2—C3—C2	−6.8 (2)	N2—C8—C9—O1	179.82 (16)
C13—O2—C3—C4	173.08 (14)	C7—C8—C9—N1	−178.88 (14)
O3—C4—C3—O2	4.9 (2)	N2—C8—C9—N1	1.08 (16)
C5—C4—C3—O2	−178.61 (14)	C8—N2—C10—N1	−1.43 (17)
O3—C4—C3—C2	−175.25 (14)	C8—N2—C10—C11	178.14 (14)
C5—C4—C3—C2	1.3 (2)	C9—N1—C10—N2	2.22 (18)
O2—C3—C2—C1	178.81 (14)	C12—N1—C10—N2	−176.97 (15)
C4—C3—C2—C1	−1.1 (2)	C9—N1—C10—C11	−177.37 (14)
C6—C1—C2—C3	−0.4 (2)	C12—N1—C10—C11	3.4 (2)

(Form_V)

Crystal data

C15H18N2O4	Z = 8
Mr = 290.31	F(000) = 1232
Triclinic, P1	Dx = 1.353 Mg m^−3
a = 13.1277 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.977 (2) Å	Cell parameters from 9928 reflections
c = 17.802 (3) Å	θ = 2.3–29.5°
α = 80.629 (5)°	µ = 0.10 mm^−1
β = 82.485 (5)°	T = 100 K
γ = 62.419 (5)°	PLATE, yellow
V = 2850.9 (7) Å^3	0.22 × 0.11 × 0.08 mm

Data collection

Bruker D8 VENTURE Kappa Duo PHOTON II CPAD diffractometer	15991 independent reflections
Radiation source: micro-focus sealed tube, Incoatech IµS HB	13406 reflections with I > 2σ(I)
Multilayer mirrors monochromator	Rint = 0.058
Detector resolution: 7.39 pixels mm^-1	θmax = 29.6°, θmin = 2.3°
φ and ω scans	h = −18→18
Absorption correction: multi-scan SADABS (Bruker, 2006)	k = −19→19
Tmin = 0.979, Tmax = 0.992	l = −24→24
171837 measured reflections

Refinement

Refinement on F^2	76 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.065	H-atom parameters constrained
wR(F^2) = 0.147	w = 1/[σ^2(Fo^2) + (0.0456P)^2 + 2.2488P] where P = (Fo^2 + 2Fc^2)/3
S = 1.16	(Δ/σ)max = 0.001
15991 reflections	Δρmax = 0.57 e Å^−3
831 parameters	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	Occ. (<1)
O1A	0.37442 (12)	0.22526 (11)	1.17909 (8)	0.0303 (3)
O2A	0.40766 (12)	0.02252 (11)	0.78871 (8)	0.0280 (3)
O3A	0.51539 (13)	0.12996 (12)	0.70170 (8)	0.0334 (3)
O4A	0.56271 (13)	0.26833 (12)	0.75772 (8)	0.0324 (3)
N1A	0.31375 (13)	0.07259 (12)	1.06539 (9)	0.0221 (3)
N2A	0.29191 (13)	0.10893 (12)	1.18744 (9)	0.0229 (3)
C1A	0.43440 (14)	0.17169 (14)	0.93235 (10)	0.0214 (3)
C2A	0.40434 (15)	0.10313 (14)	0.90109 (11)	0.0225 (3)
H2A	0.3671	0.0654	0.9325	0.027*
C3A	0.42923 (15)	0.09064 (14)	0.82403 (11)	0.0232 (3)
C4A	0.48244 (15)	0.14752 (15)	0.77700 (11)	0.0246 (4)
C5A	0.51013 (15)	0.21727 (15)	0.80815 (11)	0.0247 (4)
C6A	0.48736 (15)	0.22905 (14)	0.88524 (11)	0.0233 (3)
H6A	0.5075	0.2758	0.9062	0.028*
C7A	0.41347 (15)	0.18619 (14)	1.01317 (11)	0.0220 (3)
H7A	0.4409	0.2317	1.0285	0.026*
C8A	0.36071 (15)	0.14427 (14)	1.06942 (10)	0.0218 (3)
C9A	0.34692 (14)	0.16798 (14)	1.14955 (11)	0.0219 (3)
C10A	0.27619 (14)	0.05413 (14)	1.13487 (10)	0.0213 (3)
C11A	0.21955 (16)	−0.01762 (16)	1.15820 (11)	0.0266 (4)
H11G	0.1376	0.0267	1.1713	0.040*
H11H	0.2557	−0.0685	1.2027	0.040*
H11I	0.2281	−0.0585	1.1160	0.040*
C12A	0.25956 (17)	0.10473 (16)	1.26894 (11)	0.0283 (4)
H12G	0.3210	0.0422	1.2961	0.042*
H12H	0.1881	0.0974	1.2782	0.042*
H12I	0.2478	0.1717	1.2873	0.042*
C13A	0.34910 (17)	−0.03300 (16)	0.83483 (11)	0.0274 (4)
H13G	0.3974	−0.0817	0.8759	0.041*
H13H	0.3336	−0.0755	0.8033	0.041*
H13I	0.2762	0.0202	0.8568	0.041*
C14A	0.4237 (2)	0.1811 (2)	0.65143 (13)	0.0414 (5)
H14G	0.3637	0.1583	0.6700	0.062*
H14H	0.4532	0.1599	0.6002	0.062*
H14I	0.3911	0.2602	0.6496	0.062*
C15A	0.5967 (2)	0.33727 (18)	0.78827 (14)	0.0390 (5)
H15G	0.5286	0.3959	0.8104	0.058*
H15H	0.6340	0.3685	0.7474	0.058*
H15I	0.6508	0.2945	0.8279	0.058*
O2B	0.92455 (13)	0.63852 (12)	0.24997 (7)	0.0292 (3)
O3B	1.06757 (12)	0.72443 (10)	0.20938 (7)	0.0254 (3)
O4B	1.15014 (11)	0.78775 (11)	0.31315 (7)	0.0240 (3)
C1B	0.96858 (14)	0.68295 (13)	0.43952 (9)	0.0175 (3)
C2B	0.92859 (15)	0.64861 (13)	0.38489 (9)	0.0192 (3)
H2B	0.8807	0.6137	0.4002	0.023*
C3B	0.95993 (15)	0.66630 (14)	0.30796 (9)	0.0207 (3)
C4B	1.03277 (15)	0.71543 (14)	0.28531 (9)	0.0200 (3)
C5B	1.07362 (14)	0.74774 (13)	0.34024 (9)	0.0190 (3)
C6B	1.04008 (14)	0.73351 (14)	0.41705 (9)	0.0187 (3)
H6B	1.0656	0.7580	0.4541	0.022*
C7B	0.94005 (14)	0.66734 (13)	0.52074 (9)	0.0183 (3)
H7B	0.9739	0.6925	0.5519	0.022*
C8B	0.87349 (14)	0.62313 (13)	0.55932 (9)	0.0183 (3)
C10B	0.76139 (14)	0.54659 (13)	0.59473 (10)	0.0189 (3)
N2B	0.78799 (13)	0.56622 (12)	0.66167 (8)	0.0211 (3)
N1B	0.8099 (3)	0.5782 (3)	0.53239 (19)	0.0186 (7)	0.9
O1B	0.90225 (13)	0.63908 (12)	0.68930 (8)	0.0258 (3)	0.9
C9B	0.8579 (3)	0.6158 (3)	0.6436 (2)	0.0182 (8)	0.9
C9BA	0.789 (3)	0.591 (3)	0.536 (2)	0.016 (6)	0.1
O1BA	0.7731 (9)	0.5808 (9)	0.4750 (6)	0.016 (2)	0.1
N1BA	0.8773 (19)	0.6011 (18)	0.6448 (14)	0.004 (4)	0.1
C11B	0.68713 (15)	0.49263 (15)	0.59550 (11)	0.0240 (4)
H11D	0.6831	0.4811	0.5433	0.036*
H11E	0.6096	0.5387	0.6163	0.036*
H11F	0.7196	0.4224	0.6273	0.036*
C12B	0.75049 (17)	0.53966 (16)	0.73984 (10)	0.0248 (4)
H12D	0.8154	0.4785	0.7651	0.037*
H12E	0.6882	0.5198	0.7390	0.037*
H12F	0.7227	0.6029	0.7678	0.037*
C13B	0.85339 (19)	0.58536 (19)	0.27020 (12)	0.0330 (4)
H13D	0.8967	0.5147	0.2994	0.049*
H13E	0.8290	0.5747	0.2238	0.049*
H13F	0.7854	0.6301	0.3013	0.049*
C14B	1.0275 (2)	0.83363 (16)	0.17314 (11)	0.0307 (4)
H14D	0.9437	0.8730	0.1821	0.046*
H14E	1.0475	0.8328	0.1182	0.046*
H14F	1.0639	0.8699	0.1943	0.046*
C15B	1.18279 (17)	0.83417 (17)	0.36608 (11)	0.0270 (4)
H15D	1.1143	0.8955	0.3852	0.041*
H15E	1.2379	0.8597	0.3403	0.041*
H15F	1.2184	0.7791	0.4088	0.041*
O2C	0.69139 (12)	0.37350 (12)	0.42447 (8)	0.0304 (3)
O3C	0.60346 (12)	0.24689 (11)	0.50809 (7)	0.0271 (3)
O4C	0.49485 (12)	0.16305 (11)	0.44434 (8)	0.0265 (3)
N2C	0.66652 (13)	0.43151 (13)	0.01855 (9)	0.0251 (3)
C1C	0.57368 (14)	0.31005 (14)	0.27248 (10)	0.0207 (3)
C2C	0.62957 (15)	0.35447 (14)	0.30720 (11)	0.0228 (3)
H2C	0.6612	0.3982	0.2772	0.027*
C3C	0.63831 (15)	0.33425 (15)	0.38556 (11)	0.0229 (3)
C4C	0.59147 (15)	0.27043 (14)	0.43062 (10)	0.0222 (3)
C5C	0.53581 (14)	0.22626 (14)	0.39587 (10)	0.0212 (3)
C6C	0.52616 (14)	0.24616 (14)	0.31737 (10)	0.0207 (3)
H6C	0.4876	0.2167	0.2941	0.025*
C7C	0.56724 (15)	0.32375 (14)	0.18990 (10)	0.0222 (3)
H7C	0.5273	0.2909	0.1720	0.027*
C8C	0.61058 (15)	0.37697 (14)	0.13544 (10)	0.0214 (3)
C9C	0.6070 (2)	0.3746 (2)	0.05096 (16)	0.0214 (5)	0.9
O1C	0.56481 (13)	0.33352 (13)	0.01814 (8)	0.0321 (3)	0.95
N1C	0.6664 (3)	0.4383 (3)	0.14343 (18)	0.0208 (7)	0.9
C9CA	0.681 (2)	0.434 (2)	0.1519 (17)	0.006 (5)	0.1
O1CA	0.698 (2)	0.475 (2)	0.1999 (12)	0.024 (5)	0.05
N1CA	0.615 (2)	0.364 (2)	0.0741 (14)	0.034 (6)	0.1
C10C	0.69820 (14)	0.46766 (14)	0.07520 (10)	0.0206 (3)
C11C	0.75981 (16)	0.53553 (15)	0.05665 (11)	0.0252 (4)
H11J	0.7640	0.5623	0.1031	0.038*
H11K	0.7182	0.5973	0.0191	0.038*
H11L	0.8379	0.4918	0.0354	0.038*
C12C	0.69047 (18)	0.44906 (19)	−0.06349 (11)	0.0322 (4)
H12J	0.7730	0.4067	−0.0761	0.048*
H12K	0.6678	0.5264	−0.0790	0.048*
H12L	0.6467	0.4259	−0.0904	0.048*
C13C	0.74591 (18)	0.43344 (18)	0.37992 (12)	0.0328 (4)
H13J	0.8043	0.3878	0.3437	0.049*
H13K	0.7827	0.4554	0.4136	0.049*
H13L	0.6882	0.4982	0.3518	0.049*
C14C	0.53167 (19)	0.33723 (17)	0.55004 (11)	0.0319 (4)
H14J	0.5501	0.3978	0.5317	0.048*
H14K	0.5453	0.3156	0.6044	0.048*
H14L	0.4506	0.3600	0.5426	0.048*
C15C	0.42451 (18)	0.12840 (17)	0.41272 (12)	0.0320 (4)
H15J	0.3578	0.1921	0.3913	0.048*
H15K	0.3981	0.0865	0.4528	0.048*
H15L	0.4695	0.0828	0.3724	0.048*
O1D	0.07419 (13)	0.86772 (12)	0.54178 (7)	0.0296 (3)
O2D	0.10873 (13)	0.83184 (11)	0.98036 (7)	0.0274 (3)
O3D	0.01787 (11)	0.69735 (10)	1.02722 (7)	0.0217 (3)
O4D	−0.05284 (11)	0.61644 (10)	0.92870 (7)	0.0219 (3)
N1D	0.16229 (13)	0.96711 (12)	0.57055 (8)	0.0204 (3)
N2D	0.15506 (13)	0.93819 (12)	0.69947 (8)	0.0213 (3)
C1D	0.05115 (14)	0.78827 (13)	0.79415 (9)	0.0174 (3)
C2D	0.08989 (14)	0.82752 (14)	0.84656 (9)	0.0191 (3)
H2D	0.1253	0.8736	0.8291	0.023*
C3D	0.07572 (15)	0.79815 (14)	0.92417 (10)	0.0197 (3)
C4D	0.02462 (14)	0.72898 (14)	0.95026 (9)	0.0188 (3)
C5D	−0.01058 (14)	0.68800 (13)	0.89769 (9)	0.0184 (3)
C6D	0.00116 (14)	0.71837 (13)	0.81984 (9)	0.0180 (3)
H6D	−0.0246	0.6918	0.7843	0.022*
C7D	0.05919 (14)	0.81853 (14)	0.71217 (9)	0.0189 (3)
H7D	0.0285	0.7887	0.6823	0.023*
C8D	0.10373 (14)	0.88251 (14)	0.67243 (9)	0.0184 (3)
C9D	0.10827 (15)	0.90093 (14)	0.58731 (9)	0.0197 (3)
C10D	0.18766 (14)	0.98505 (14)	0.63844 (10)	0.0199 (3)
C11D	0.24792 (17)	1.05211 (15)	0.63853 (11)	0.0258 (4)
H11A	0.2566	1.0577	0.6913	0.039*
H11B	0.2029	1.1249	0.6125	0.039*
H11C	0.3241	1.0181	0.6119	0.039*
C12D	0.19168 (17)	1.00616 (16)	0.49376 (10)	0.0259 (4)
H12A	0.1773	1.0818	0.4922	0.039*
H12B	0.1443	1.0019	0.4575	0.039*
H12C	0.2732	0.9611	0.4800	0.039*
C13D	0.1633 (2)	0.90031 (19)	0.95627 (12)	0.0348 (5)
H13A	0.2324	0.8627	0.9235	0.052*
H13B	0.1849	0.9177	1.0010	0.052*
H13C	0.1100	0.9676	0.9277	0.052*
C14D	−0.09805 (16)	0.73912 (17)	1.06124 (10)	0.0272 (4)
H14A	−0.1377	0.8182	1.0483	0.041*
H14B	−0.0960	0.7217	1.1168	0.041*
H14C	−0.1392	0.7060	1.0418	0.041*
C15D	−0.08155 (17)	0.56618 (16)	0.87670 (10)	0.0255 (4)
H15A	−0.1487	0.6208	0.8496	0.038*
H15B	−0.0996	0.5090	0.9050	0.038*
H15C	−0.0161	0.5342	0.8398	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0315 (7)	0.0318 (7)	0.0343 (7)	−0.0187 (6)	−0.0017 (6)	−0.0076 (6)
O2A	0.0335 (7)	0.0278 (7)	0.0287 (7)	−0.0196 (6)	0.0031 (6)	−0.0048 (5)
O3A	0.0349 (8)	0.0329 (7)	0.0290 (7)	−0.0141 (6)	0.0084 (6)	−0.0066 (6)
O4A	0.0378 (8)	0.0309 (7)	0.0349 (8)	−0.0237 (6)	0.0132 (6)	−0.0068 (6)
N1A	0.0200 (7)	0.0214 (7)	0.0259 (7)	−0.0104 (6)	−0.0030 (6)	−0.0011 (6)
N2A	0.0213 (7)	0.0251 (7)	0.0235 (7)	−0.0114 (6)	−0.0016 (6)	−0.0025 (6)
C1A	0.0172 (8)	0.0176 (8)	0.0277 (9)	−0.0070 (6)	−0.0009 (6)	−0.0013 (6)
C2A	0.0186 (8)	0.0207 (8)	0.0281 (9)	−0.0100 (7)	−0.0003 (7)	−0.0001 (7)
C3A	0.0194 (8)	0.0201 (8)	0.0296 (9)	−0.0088 (7)	−0.0001 (7)	−0.0033 (7)
C4A	0.0214 (8)	0.0232 (8)	0.0269 (9)	−0.0092 (7)	0.0034 (7)	−0.0038 (7)
C5A	0.0201 (8)	0.0209 (8)	0.0319 (9)	−0.0104 (7)	0.0049 (7)	−0.0014 (7)
C6A	0.0206 (8)	0.0198 (8)	0.0306 (9)	−0.0107 (7)	0.0024 (7)	−0.0038 (7)
C7A	0.0185 (8)	0.0172 (8)	0.0300 (9)	−0.0076 (6)	−0.0040 (7)	−0.0012 (7)
C8A	0.0184 (8)	0.0191 (8)	0.0267 (9)	−0.0072 (6)	−0.0046 (6)	−0.0013 (7)
C9A	0.0170 (8)	0.0200 (8)	0.0284 (9)	−0.0078 (6)	−0.0033 (6)	−0.0025 (7)
C10A	0.0163 (7)	0.0200 (8)	0.0269 (9)	−0.0074 (6)	−0.0054 (6)	−0.0003 (7)
C11A	0.0263 (9)	0.0278 (9)	0.0307 (10)	−0.0168 (8)	−0.0010 (7)	−0.0025 (7)
C12A	0.0286 (9)	0.0313 (10)	0.0240 (9)	−0.0129 (8)	−0.0022 (7)	−0.0028 (7)
C13A	0.0293 (9)	0.0271 (9)	0.0322 (10)	−0.0186 (8)	−0.0015 (8)	−0.0025 (8)
C14A	0.0525 (14)	0.0563 (14)	0.0304 (11)	−0.0389 (12)	0.0007 (10)	−0.0025 (10)
C15A	0.0460 (13)	0.0340 (11)	0.0467 (13)	−0.0294 (10)	0.0216 (10)	−0.0147 (9)
O2B	0.0449 (8)	0.0387 (8)	0.0163 (6)	−0.0287 (7)	0.0013 (5)	−0.0069 (5)
O3B	0.0366 (7)	0.0254 (6)	0.0137 (6)	−0.0153 (6)	0.0051 (5)	−0.0024 (5)
O4B	0.0267 (6)	0.0350 (7)	0.0163 (6)	−0.0203 (6)	0.0020 (5)	−0.0011 (5)
C1B	0.0181 (7)	0.0167 (7)	0.0157 (7)	−0.0068 (6)	0.0003 (6)	−0.0011 (6)
C2B	0.0227 (8)	0.0191 (8)	0.0167 (7)	−0.0108 (7)	0.0010 (6)	−0.0020 (6)
C3B	0.0266 (8)	0.0200 (8)	0.0162 (7)	−0.0108 (7)	0.0003 (6)	−0.0047 (6)
C4B	0.0248 (8)	0.0191 (8)	0.0138 (7)	−0.0092 (7)	0.0028 (6)	−0.0013 (6)
C5B	0.0180 (7)	0.0190 (8)	0.0190 (8)	−0.0085 (6)	0.0002 (6)	−0.0003 (6)
C6B	0.0199 (8)	0.0203 (8)	0.0160 (7)	−0.0094 (6)	−0.0013 (6)	−0.0014 (6)
C7B	0.0212 (8)	0.0184 (7)	0.0151 (7)	−0.0088 (6)	−0.0020 (6)	−0.0010 (6)
C8B	0.0208 (8)	0.0182 (7)	0.0149 (7)	−0.0082 (6)	−0.0017 (6)	−0.0008 (6)
C10B	0.0180 (7)	0.0159 (7)	0.0220 (8)	−0.0072 (6)	−0.0036 (6)	0.0000 (6)
N2B	0.0235 (7)	0.0237 (7)	0.0166 (7)	−0.0123 (6)	−0.0002 (5)	0.0002 (5)
N1B	0.0186 (11)	0.0189 (10)	0.0183 (9)	−0.0086 (8)	−0.0017 (7)	−0.0009 (6)
O1B	0.0328 (7)	0.0333 (7)	0.0187 (6)	−0.0214 (6)	−0.0006 (5)	−0.0029 (5)
C9B	0.0177 (11)	0.0189 (11)	0.0169 (10)	−0.0074 (8)	−0.0009 (7)	−0.0015 (7)
C9BA	0.016 (7)	0.016 (7)	0.016 (7)	−0.007 (3)	−0.0011 (11)	−0.0022 (13)
O1BA	0.017 (3)	0.017 (3)	0.015 (3)	−0.0089 (19)	−0.0015 (18)	−0.0028 (18)
N1BA	0.004 (4)	0.004 (4)	0.003 (4)	−0.002 (2)	0.0000 (10)	−0.0002 (11)
C11B	0.0217 (8)	0.0243 (8)	0.0285 (9)	−0.0128 (7)	−0.0025 (7)	−0.0016 (7)
C12B	0.0303 (9)	0.0286 (9)	0.0166 (8)	−0.0164 (8)	0.0035 (7)	0.0005 (7)
C13B	0.0379 (11)	0.0476 (12)	0.0276 (10)	−0.0301 (10)	0.0064 (8)	−0.0149 (9)
C14B	0.0493 (12)	0.0291 (10)	0.0172 (8)	−0.0223 (9)	−0.0028 (8)	0.0033 (7)
C15B	0.0307 (9)	0.0357 (10)	0.0228 (9)	−0.0227 (8)	0.0018 (7)	−0.0034 (7)
O2C	0.0324 (7)	0.0398 (8)	0.0308 (7)	−0.0263 (7)	−0.0022 (6)	−0.0030 (6)
O3C	0.0282 (7)	0.0284 (7)	0.0242 (6)	−0.0128 (6)	−0.0068 (5)	0.0024 (5)
O4C	0.0298 (7)	0.0299 (7)	0.0261 (7)	−0.0211 (6)	−0.0024 (5)	0.0042 (5)
N2C	0.0241 (7)	0.0327 (8)	0.0215 (7)	−0.0155 (7)	−0.0007 (6)	−0.0025 (6)
C1C	0.0169 (7)	0.0198 (8)	0.0238 (8)	−0.0076 (6)	0.0020 (6)	−0.0035 (6)
C2C	0.0194 (8)	0.0222 (8)	0.0284 (9)	−0.0119 (7)	0.0022 (7)	−0.0024 (7)
C3C	0.0171 (8)	0.0246 (8)	0.0291 (9)	−0.0108 (7)	−0.0016 (7)	−0.0041 (7)
C4C	0.0191 (8)	0.0226 (8)	0.0234 (8)	−0.0088 (7)	−0.0027 (6)	0.0004 (7)
C5C	0.0168 (7)	0.0200 (8)	0.0261 (9)	−0.0092 (6)	−0.0007 (6)	0.0015 (7)
C6C	0.0174 (7)	0.0203 (8)	0.0256 (8)	−0.0097 (6)	0.0011 (6)	−0.0042 (6)
C7C	0.0188 (8)	0.0231 (8)	0.0261 (9)	−0.0109 (7)	0.0022 (6)	−0.0047 (7)
C8C	0.0210 (8)	0.0231 (8)	0.0212 (8)	−0.0110 (7)	0.0018 (6)	−0.0046 (7)
C9C	0.0209 (8)	0.0245 (8)	0.0192 (8)	−0.0109 (6)	−0.0009 (7)	−0.0016 (7)
O1C	0.0358 (7)	0.0445 (8)	0.0266 (7)	−0.0269 (7)	−0.0010 (6)	−0.0058 (6)
N1C	0.0211 (11)	0.0215 (9)	0.0200 (10)	−0.0101 (7)	−0.0010 (7)	−0.0014 (6)
C9CA	0.006 (5)	0.006 (5)	0.006 (5)	−0.003 (2)	−0.0002 (11)	−0.0003 (12)
O1CA	0.024 (5)	0.024 (5)	0.024 (5)	−0.011 (3)	−0.001 (2)	−0.002 (2)
N1CA	0.034 (6)	0.034 (6)	0.035 (6)	−0.016 (3)	−0.0023 (11)	−0.0039 (12)
C10C	0.0181 (8)	0.0200 (8)	0.0214 (8)	−0.0072 (6)	−0.0005 (6)	−0.0016 (6)
C11C	0.0268 (9)	0.0247 (9)	0.0262 (9)	−0.0148 (7)	−0.0003 (7)	0.0003 (7)
C12C	0.0329 (10)	0.0497 (12)	0.0194 (9)	−0.0240 (10)	−0.0013 (7)	−0.0019 (8)
C13C	0.0339 (10)	0.0404 (11)	0.0372 (11)	−0.0281 (9)	0.0067 (8)	−0.0108 (9)
C14C	0.0408 (11)	0.0360 (11)	0.0234 (9)	−0.0213 (9)	−0.0022 (8)	−0.0024 (8)
C15C	0.0294 (10)	0.0362 (11)	0.0381 (11)	−0.0236 (9)	−0.0048 (8)	0.0055 (9)
O1D	0.0426 (8)	0.0392 (8)	0.0188 (6)	−0.0288 (7)	0.0002 (5)	−0.0038 (5)
O2D	0.0437 (8)	0.0377 (7)	0.0158 (6)	−0.0316 (7)	−0.0063 (5)	0.0026 (5)
O3D	0.0243 (6)	0.0293 (6)	0.0147 (5)	−0.0159 (5)	−0.0029 (5)	0.0024 (5)
O4D	0.0297 (6)	0.0280 (6)	0.0165 (6)	−0.0211 (6)	−0.0007 (5)	−0.0001 (5)
N1D	0.0233 (7)	0.0228 (7)	0.0174 (7)	−0.0134 (6)	0.0006 (5)	−0.0006 (5)
N2D	0.0246 (7)	0.0217 (7)	0.0200 (7)	−0.0130 (6)	−0.0018 (6)	−0.0009 (6)
C1D	0.0165 (7)	0.0191 (7)	0.0162 (7)	−0.0081 (6)	−0.0002 (6)	−0.0012 (6)
C2D	0.0205 (8)	0.0205 (8)	0.0195 (8)	−0.0126 (7)	−0.0015 (6)	−0.0002 (6)
C3D	0.0220 (8)	0.0228 (8)	0.0177 (8)	−0.0125 (7)	−0.0033 (6)	−0.0019 (6)
C4D	0.0196 (8)	0.0210 (8)	0.0161 (7)	−0.0103 (6)	−0.0017 (6)	0.0006 (6)
C5D	0.0173 (7)	0.0201 (8)	0.0193 (8)	−0.0106 (6)	−0.0009 (6)	0.0008 (6)
C6D	0.0190 (7)	0.0198 (8)	0.0179 (7)	−0.0107 (6)	−0.0015 (6)	−0.0030 (6)
C7D	0.0200 (8)	0.0212 (8)	0.0174 (7)	−0.0108 (7)	−0.0003 (6)	−0.0034 (6)
C8D	0.0190 (7)	0.0204 (8)	0.0155 (7)	−0.0089 (6)	0.0005 (6)	−0.0026 (6)
C9D	0.0219 (8)	0.0220 (8)	0.0166 (7)	−0.0121 (7)	0.0016 (6)	−0.0010 (6)
C10D	0.0182 (7)	0.0185 (8)	0.0232 (8)	−0.0085 (6)	−0.0031 (6)	−0.0009 (6)
C11D	0.0287 (9)	0.0248 (9)	0.0294 (9)	−0.0172 (8)	−0.0052 (7)	0.0013 (7)
C12D	0.0337 (10)	0.0293 (9)	0.0193 (8)	−0.0200 (8)	0.0029 (7)	−0.0001 (7)
C13D	0.0574 (14)	0.0440 (12)	0.0246 (9)	−0.0410 (11)	−0.0103 (9)	0.0021 (8)
C14D	0.0278 (9)	0.0402 (11)	0.0166 (8)	−0.0191 (8)	0.0015 (7)	−0.0021 (7)
C15D	0.0348 (10)	0.0295 (9)	0.0221 (8)	−0.0233 (8)	0.0017 (7)	−0.0045 (7)

Geometric parameters (Å, º)

O1A—C9A	1.226 (2)	O2C—C3C	1.368 (2)
O2A—C3A	1.369 (2)	O2C—C13C	1.426 (2)
O2A—C13A	1.431 (2)	O3C—C4C	1.377 (2)
O3A—C4A	1.379 (2)	O3C—C14C	1.436 (2)
O3A—C14A	1.428 (3)	O4C—C5C	1.373 (2)
O4A—C5A	1.370 (2)	O4C—C15C	1.429 (2)
O4A—C15A	1.434 (3)	N2C—C9C	1.373 (3)
N1A—C10A	1.301 (2)	N2C—C10C	1.384 (2)
N1A—C8A	1.413 (2)	N2C—C12C	1.458 (2)
N2A—C9A	1.379 (2)	N2C—N1CA	1.56 (3)
N2A—C10A	1.391 (2)	C1C—C2C	1.404 (2)
N2A—C12A	1.457 (2)	C1C—C6C	1.406 (2)
C1A—C2A	1.402 (2)	C1C—C7C	1.460 (2)
C1A—C6A	1.405 (2)	C2C—C3C	1.387 (3)
C1A—C7A	1.458 (3)	C2C—H2C	0.9500
C2A—C3A	1.388 (3)	C3C—C4C	1.401 (2)
C2A—H2A	0.9500	C4C—C5C	1.399 (2)
C3A—C4A	1.402 (2)	C5C—C6C	1.390 (2)
C4A—C5A	1.395 (3)	C6C—H6C	0.9500
C5A—C6A	1.386 (3)	C7C—C8C	1.353 (2)
C6A—H6A	0.9500	C7C—H7C	0.9500
C7A—C8A	1.352 (3)	C8C—N1CA	1.13 (2)
C7A—H7A	0.9500	C8C—N1C	1.393 (4)
C8A—C9A	1.486 (3)	C8C—C9C	1.517 (3)
C10A—C11A	1.485 (2)	C8C—C9CA	1.56 (3)
C11A—H11G	0.9800	C9C—O1C	1.211 (3)
C11A—H11H	0.9800	N1C—C10C	1.297 (4)
C11A—H11I	0.9800	C9CA—O1CA	1.19 (4)
C12A—H12G	0.9800	C9CA—C10C	1.39 (3)
C12A—H12H	0.9800	C10C—C11C	1.484 (2)
C12A—H12I	0.9800	C11C—H11J	0.9800
C13A—H13G	0.9800	C11C—H11K	0.9800
C13A—H13H	0.9800	C11C—H11L	0.9800
C13A—H13I	0.9800	C12C—H12J	0.9800
C14A—H14G	0.9800	C12C—H12K	0.9800
C14A—H14H	0.9800	C12C—H12L	0.9800
C14A—H14I	0.9800	C13C—H13J	0.9800
C15A—H15G	0.9800	C13C—H13K	0.9800
C15A—H15H	0.9800	C13C—H13L	0.9800
C15A—H15I	0.9800	C14C—H14J	0.9800
O2B—C3B	1.362 (2)	C14C—H14K	0.9800
O2B—C13B	1.422 (2)	C14C—H14L	0.9800
O3B—C4B	1.3741 (19)	C15C—H15J	0.9800
O3B—C14B	1.431 (2)	C15C—H15K	0.9800
O4B—C5B	1.364 (2)	C15C—H15L	0.9800
O4B—C15B	1.433 (2)	O1D—C9D	1.218 (2)
C1B—C6B	1.402 (2)	O2D—C3D	1.366 (2)
C1B—C2B	1.404 (2)	O2D—C13D	1.426 (2)
C1B—C7B	1.452 (2)	O3D—C4D	1.374 (2)
C2B—C3B	1.394 (2)	O3D—C14D	1.440 (2)
C2B—H2B	0.9500	O4D—C5D	1.3663 (19)
C3B—C4B	1.402 (2)	O4D—C15D	1.429 (2)
C4B—C5B	1.398 (2)	N1D—C9D	1.382 (2)
C5B—C6B	1.392 (2)	N1D—C10D	1.384 (2)
C6B—H6B	0.9500	N1D—C12D	1.459 (2)
C7B—C8B	1.350 (2)	N2D—C10D	1.303 (2)
C7B—H7B	0.9500	N2D—C8D	1.409 (2)
C8B—N1B	1.417 (4)	C1D—C6D	1.401 (2)
C8B—C9B	1.481 (4)	C1D—C2D	1.407 (2)
C8B—C9BA	1.50 (4)	C1D—C7D	1.456 (2)
C8B—N1BA	1.50 (2)	C2D—C3D	1.390 (2)
C10B—C9BA	1.23 (4)	C2D—H2D	0.9500
C10B—N1B	1.323 (4)	C3D—C4D	1.405 (2)
C10B—N2B	1.386 (2)	C4D—C5D	1.397 (2)
C10B—C11B	1.481 (2)	C5D—C6D	1.392 (2)
N2B—C9B	1.366 (4)	C6D—H6D	0.9500
N2B—N1BA	1.45 (2)	C7D—C8D	1.346 (2)
N2B—C12B	1.462 (2)	C7D—H7D	0.9500
O1B—C9B	1.221 (4)	C8D—C9D	1.493 (2)
C9BA—O1BA	1.17 (4)	C10D—C11D	1.481 (2)
C11B—H11D	0.9800	C11D—H11A	0.9800
C11B—H11E	0.9800	C11D—H11B	0.9800
C11B—H11F	0.9800	C11D—H11C	0.9800
C12B—H12D	0.9800	C12D—H12A	0.9800
C12B—H12E	0.9800	C12D—H12B	0.9800
C12B—H12F	0.9800	C12D—H12C	0.9800
C13B—H13D	0.9800	C13D—H13A	0.9800
C13B—H13E	0.9800	C13D—H13B	0.9800
C13B—H13F	0.9800	C13D—H13C	0.9800
C14B—H14D	0.9800	C14D—H14A	0.9800
C14B—H14E	0.9800	C14D—H14B	0.9800
C14B—H14F	0.9800	C14D—H14C	0.9800
C15B—H15D	0.9800	C15D—H15A	0.9800
C15B—H15E	0.9800	C15D—H15B	0.9800
C15B—H15F	0.9800	C15D—H15C	0.9800
C3A—O2A—C13A	116.24 (15)	C3C—O2C—C13C	116.74 (15)
C4A—O3A—C14A	114.73 (16)	C4C—O3C—C14C	113.58 (14)
C5A—O4A—C15A	116.67 (16)	C5C—O4C—C15C	116.81 (14)
C10A—N1A—C8A	105.21 (15)	C9C—N2C—C10C	109.56 (17)
C9A—N2A—C10A	108.13 (15)	C9C—N2C—C12C	123.42 (18)
C9A—N2A—C12A	124.57 (16)	C10C—N2C—C12C	127.02 (16)
C10A—N2A—C12A	127.29 (15)	C10C—N2C—N1CA	95.6 (9)
C2A—C1A—C6A	119.84 (17)	C12C—N2C—N1CA	137.1 (9)
C2A—C1A—C7A	122.51 (16)	C2C—C1C—C6C	119.88 (16)
C6A—C1A—C7A	117.65 (16)	C2C—C1C—C7C	122.08 (16)
C3A—C2A—C1A	119.74 (16)	C6C—C1C—C7C	117.99 (16)
C3A—C2A—H2A	120.1	C3C—C2C—C1C	119.67 (16)
C1A—C2A—H2A	120.1	C3C—C2C—H2C	120.2
O2A—C3A—C2A	124.26 (16)	C1C—C2C—H2C	120.2
O2A—C3A—C4A	115.25 (16)	O2C—C3C—C2C	123.96 (16)
C2A—C3A—C4A	120.47 (17)	O2C—C3C—C4C	115.27 (16)
O3A—C4A—C5A	119.20 (16)	C2C—C3C—C4C	120.77 (16)
O3A—C4A—C3A	121.12 (17)	O3C—C4C—C5C	119.51 (15)
C5A—C4A—C3A	119.51 (17)	O3C—C4C—C3C	121.01 (16)
O4A—C5A—C6A	124.40 (17)	C5C—C4C—C3C	119.44 (16)
O4A—C5A—C4A	115.06 (17)	O4C—C5C—C6C	124.35 (16)
C6A—C5A—C4A	120.51 (16)	O4C—C5C—C4C	115.28 (16)
C5A—C6A—C1A	119.89 (17)	C6C—C5C—C4C	120.37 (16)
C5A—C6A—H6A	120.1	C5C—C6C—C1C	119.87 (16)
C1A—C6A—H6A	120.1	C5C—C6C—H6C	120.1
C8A—C7A—C1A	129.38 (17)	C1C—C6C—H6C	120.1
C8A—C7A—H7A	115.3	C8C—C7C—C1C	128.68 (16)
C1A—C7A—H7A	115.3	C8C—C7C—H7C	115.7
C7A—C8A—N1A	128.90 (17)	C1C—C7C—H7C	115.7
C7A—C8A—C9A	122.08 (16)	N1CA—C8C—C7C	118.9 (14)
N1A—C8A—C9A	108.99 (15)	C7C—C8C—N1C	129.3 (2)
O1A—C9A—N2A	125.16 (17)	C7C—C8C—C9C	122.38 (17)
O1A—C9A—C8A	131.53 (17)	N1C—C8C—C9C	108.3 (2)
N2A—C9A—C8A	103.31 (14)	N1CA—C8C—C9CA	115.3 (17)
N1A—C10A—N2A	114.35 (15)	C7C—C8C—C9CA	124.2 (11)
N1A—C10A—C11A	124.35 (16)	O1C—C9C—N2C	127.2 (2)
N2A—C10A—C11A	121.30 (16)	O1C—C9C—C8C	130.8 (2)
C10A—C11A—H11G	109.5	N2C—C9C—C8C	102.01 (18)
C10A—C11A—H11H	109.5	C10C—N1C—C8C	106.8 (2)
H11G—C11A—H11H	109.5	O1CA—C9CA—C10C	120 (3)
C10A—C11A—H11I	109.5	O1CA—C9CA—C8C	143 (3)
H11G—C11A—H11I	109.5	C10C—C9CA—C8C	94.0 (18)
H11H—C11A—H11I	109.5	C8C—N1CA—N2C	112.5 (19)
N2A—C12A—H12G	109.5	N1C—C10C—N2C	113.3 (2)
N2A—C12A—H12H	109.5	N2C—C10C—C9CA	120.8 (13)
H12G—C12A—H12H	109.5	N1C—C10C—C11C	125.2 (2)
N2A—C12A—H12I	109.5	N2C—C10C—C11C	121.46 (16)
H12G—C12A—H12I	109.5	C9CA—C10C—C11C	117.6 (13)
H12H—C12A—H12I	109.5	C10C—C11C—H11J	109.5
O2A—C13A—H13G	109.5	C10C—C11C—H11K	109.5
O2A—C13A—H13H	109.5	H11J—C11C—H11K	109.5
H13G—C13A—H13H	109.5	C10C—C11C—H11L	109.5
O2A—C13A—H13I	109.5	H11J—C11C—H11L	109.5
H13G—C13A—H13I	109.5	H11K—C11C—H11L	109.5
H13H—C13A—H13I	109.5	N2C—C12C—H12J	109.5
O3A—C14A—H14G	109.5	N2C—C12C—H12K	109.5
O3A—C14A—H14H	109.5	H12J—C12C—H12K	109.5
H14G—C14A—H14H	109.5	N2C—C12C—H12L	109.5
O3A—C14A—H14I	109.5	H12J—C12C—H12L	109.5
H14G—C14A—H14I	109.5	H12K—C12C—H12L	109.5
H14H—C14A—H14I	109.5	O2C—C13C—H13J	109.5
O4A—C15A—H15G	109.5	O2C—C13C—H13K	109.5
O4A—C15A—H15H	109.5	H13J—C13C—H13K	109.5
H15G—C15A—H15H	109.5	O2C—C13C—H13L	109.5
O4A—C15A—H15I	109.5	H13J—C13C—H13L	109.5
H15G—C15A—H15I	109.5	H13K—C13C—H13L	109.5
H15H—C15A—H15I	109.5	O3C—C14C—H14J	109.5
C3B—O2B—C13B	117.17 (14)	O3C—C14C—H14K	109.5
C4B—O3B—C14B	114.70 (14)	H14J—C14C—H14K	109.5
C5B—O4B—C15B	116.87 (13)	O3C—C14C—H14L	109.5
C6B—C1B—C2B	120.40 (15)	H14J—C14C—H14L	109.5
C6B—C1B—C7B	116.98 (15)	H14K—C14C—H14L	109.5
C2B—C1B—C7B	122.61 (15)	O4C—C15C—H15J	109.5
C3B—C2B—C1B	119.23 (15)	O4C—C15C—H15K	109.5
C3B—C2B—H2B	120.4	H15J—C15C—H15K	109.5
C1B—C2B—H2B	120.4	O4C—C15C—H15L	109.5
O2B—C3B—C2B	124.40 (16)	H15J—C15C—H15L	109.5
O2B—C3B—C4B	115.05 (15)	H15K—C15C—H15L	109.5
C2B—C3B—C4B	120.55 (15)	C3D—O2D—C13D	116.61 (14)
O3B—C4B—C5B	121.70 (15)	C4D—O3D—C14D	113.87 (13)
O3B—C4B—C3B	118.41 (15)	C5D—O4D—C15D	116.90 (13)
C5B—C4B—C3B	119.77 (15)	C9D—N1D—C10D	108.32 (14)
O4B—C5B—C6B	124.37 (15)	C9D—N1D—C12D	125.00 (15)
O4B—C5B—C4B	115.37 (14)	C10D—N1D—C12D	126.62 (15)
C6B—C5B—C4B	120.19 (15)	C10D—N2D—C8D	105.11 (14)
C5B—C6B—C1B	119.81 (15)	C6D—C1D—C2D	120.38 (15)
C5B—C6B—H6B	120.1	C6D—C1D—C7D	117.14 (14)
C1B—C6B—H6B	120.1	C2D—C1D—C7D	122.48 (15)
C8B—C7B—C1B	130.82 (16)	C3D—C2D—C1D	119.26 (15)
C8B—C7B—H7B	114.6	C3D—C2D—H2D	120.4
C1B—C7B—H7B	114.6	C1D—C2D—H2D	120.4
C7B—C8B—N1B	130.36 (19)	O2D—C3D—C2D	124.62 (15)
C7B—C8B—C9B	120.7 (2)	O2D—C3D—C4D	114.79 (14)
N1B—C8B—C9B	109.0 (2)	C2D—C3D—C4D	120.59 (15)
C7B—C8B—C9BA	133.8 (14)	O3D—C4D—C5D	121.49 (15)
C7B—C8B—N1BA	117.7 (9)	O3D—C4D—C3D	118.66 (14)
C9BA—C8B—N1BA	108.5 (17)	C5D—C4D—C3D	119.69 (15)
C9BA—C10B—N2B	115.2 (18)	O4D—C5D—C6D	124.60 (15)
N1B—C10B—N2B	113.9 (2)	O4D—C5D—C4D	115.09 (14)
C9BA—C10B—C11B	122.4 (18)	C6D—C5D—C4D	120.28 (15)
N1B—C10B—C11B	124.6 (2)	C5D—C6D—C1D	119.76 (15)
N2B—C10B—C11B	121.55 (15)	C5D—C6D—H6D	120.1
C9B—N2B—C10B	108.6 (2)	C1D—C6D—H6D	120.1
C10B—N2B—N1BA	109.3 (10)	C8D—C7D—C1D	129.54 (16)
C9B—N2B—C12B	123.7 (2)	C8D—C7D—H7D	115.2
C10B—N2B—C12B	127.67 (15)	C1D—C7D—H7D	115.2
N1BA—N2B—C12B	122.2 (10)	C7D—C8D—N2D	129.04 (15)
C10B—N1B—C8B	104.6 (2)	C7D—C8D—C9D	121.82 (15)
O1B—C9B—N2B	125.6 (3)	N2D—C8D—C9D	109.11 (14)
O1B—C9B—C8B	130.3 (3)	O1D—C9D—N1D	126.72 (16)
N2B—C9B—C8B	103.9 (3)	O1D—C9D—C8D	130.42 (16)
O1BA—C9BA—C10B	123 (3)	N1D—C9D—C8D	102.86 (14)
O1BA—C9BA—C8B	130 (3)	N2D—C10D—N1D	114.60 (15)
C10B—C9BA—C8B	105 (3)	N2D—C10D—C11D	124.69 (16)
N2B—N1BA—C8B	98.9 (15)	N1D—C10D—C11D	120.71 (15)
C10B—C11B—H11D	109.5	C10D—C11D—H11A	109.5
C10B—C11B—H11E	109.5	C10D—C11D—H11B	109.5
H11D—C11B—H11E	109.5	H11A—C11D—H11B	109.5
C10B—C11B—H11F	109.5	C10D—C11D—H11C	109.5
H11D—C11B—H11F	109.5	H11A—C11D—H11C	109.5
H11E—C11B—H11F	109.5	H11B—C11D—H11C	109.5
N2B—C12B—H12D	109.5	N1D—C12D—H12A	109.5
N2B—C12B—H12E	109.5	N1D—C12D—H12B	109.5
H12D—C12B—H12E	109.5	H12A—C12D—H12B	109.5
N2B—C12B—H12F	109.5	N1D—C12D—H12C	109.5
H12D—C12B—H12F	109.5	H12A—C12D—H12C	109.5
H12E—C12B—H12F	109.5	H12B—C12D—H12C	109.5
O2B—C13B—H13D	109.5	O2D—C13D—H13A	109.5
O2B—C13B—H13E	109.5	O2D—C13D—H13B	109.5
H13D—C13B—H13E	109.5	H13A—C13D—H13B	109.5
O2B—C13B—H13F	109.5	O2D—C13D—H13C	109.5
H13D—C13B—H13F	109.5	H13A—C13D—H13C	109.5
H13E—C13B—H13F	109.5	H13B—C13D—H13C	109.5
O3B—C14B—H14D	109.5	O3D—C14D—H14A	109.5
O3B—C14B—H14E	109.5	O3D—C14D—H14B	109.5
H14D—C14B—H14E	109.5	H14A—C14D—H14B	109.5
O3B—C14B—H14F	109.5	O3D—C14D—H14C	109.5
H14D—C14B—H14F	109.5	H14A—C14D—H14C	109.5
H14E—C14B—H14F	109.5	H14B—C14D—H14C	109.5
O4B—C15B—H15D	109.5	O4D—C15D—H15A	109.5
O4B—C15B—H15E	109.5	O4D—C15D—H15B	109.5
H15D—C15B—H15E	109.5	H15A—C15D—H15B	109.5
O4B—C15B—H15F	109.5	O4D—C15D—H15C	109.5
H15D—C15B—H15F	109.5	H15A—C15D—H15C	109.5
H15E—C15B—H15F	109.5	H15B—C15D—H15C	109.5
C6A—C1A—C2A—C3A	1.3 (3)	C6C—C1C—C2C—C3C	0.5 (3)
C7A—C1A—C2A—C3A	−178.35 (16)	C7C—C1C—C2C—C3C	−176.67 (16)
C13A—O2A—C3A—C2A	4.0 (3)	C13C—O2C—C3C—C2C	−3.6 (3)
C13A—O2A—C3A—C4A	−177.51 (16)	C13C—O2C—C3C—C4C	176.43 (17)
C1A—C2A—C3A—O2A	177.29 (16)	C1C—C2C—C3C—O2C	179.74 (16)
C1A—C2A—C3A—C4A	−1.1 (3)	C1C—C2C—C3C—C4C	−0.3 (3)
C14A—O3A—C4A—C5A	−107.0 (2)	C14C—O3C—C4C—C5C	−108.64 (19)
C14A—O3A—C4A—C3A	77.7 (2)	C14C—O3C—C4C—C3C	74.0 (2)
O2A—C3A—C4A—O3A	−3.4 (3)	O2C—C3C—C4C—O3C	−2.4 (2)
C2A—C3A—C4A—O3A	175.17 (17)	C2C—C3C—C4C—O3C	177.67 (16)
O2A—C3A—C4A—C5A	−178.67 (16)	O2C—C3C—C4C—C5C	−179.74 (16)
C2A—C3A—C4A—C5A	−0.2 (3)	C2C—C3C—C4C—C5C	0.3 (3)
C15A—O4A—C5A—C6A	0.7 (3)	C15C—O4C—C5C—C6C	−8.8 (3)
C15A—O4A—C5A—C4A	−177.54 (18)	C15C—O4C—C5C—C4C	172.00 (16)
O3A—C4A—C5A—O4A	4.1 (3)	O3C—C4C—C5C—O4C	1.3 (2)
C3A—C4A—C5A—O4A	179.48 (16)	C3C—C4C—C5C—O4C	178.68 (15)
O3A—C4A—C5A—C6A	−174.22 (17)	O3C—C4C—C5C—C6C	−177.89 (16)
C3A—C4A—C5A—C6A	1.2 (3)	C3C—C4C—C5C—C6C	−0.5 (3)
O4A—C5A—C6A—C1A	−179.09 (17)	O4C—C5C—C6C—C1C	−178.42 (16)
C4A—C5A—C6A—C1A	−1.0 (3)	C4C—C5C—C6C—C1C	0.7 (3)
C2A—C1A—C6A—C5A	−0.3 (3)	C2C—C1C—C6C—C5C	−0.7 (3)
C7A—C1A—C6A—C5A	179.39 (16)	C7C—C1C—C6C—C5C	176.60 (16)
C2A—C1A—C7A—C8A	−3.1 (3)	C2C—C1C—C7C—C8C	0.3 (3)
C6A—C1A—C7A—C8A	177.26 (18)	C6C—C1C—C7C—C8C	−176.96 (18)
C1A—C7A—C8A—N1A	1.7 (3)	C1C—C7C—C8C—N1CA	166.3 (14)
C1A—C7A—C8A—C9A	179.96 (16)	C1C—C7C—C8C—N1C	−4.4 (4)
C10A—N1A—C8A—C7A	178.17 (18)	C1C—C7C—C8C—C9C	173.77 (18)
C10A—N1A—C8A—C9A	−0.28 (18)	C1C—C7C—C8C—C9CA	1.5 (13)
C10A—N2A—C9A—O1A	−179.62 (17)	C10C—N2C—C9C—O1C	178.5 (2)
C12A—N2A—C9A—O1A	−0.9 (3)	C12C—N2C—C9C—O1C	−1.5 (4)
C10A—N2A—C9A—C8A	0.81 (18)	C10C—N2C—C9C—C8C	−2.2 (2)
C12A—N2A—C9A—C8A	179.53 (16)	C12C—N2C—C9C—C8C	177.89 (17)
C7A—C8A—C9A—O1A	1.5 (3)	C7C—C8C—C9C—O1C	3.4 (4)
N1A—C8A—C9A—O1A	−179.88 (18)	N1C—C8C—C9C—O1C	−178.0 (3)
C7A—C8A—C9A—N2A	−178.93 (16)	C7C—C8C—C9C—N2C	−175.87 (17)
N1A—C8A—C9A—N2A	−0.35 (18)	N1C—C8C—C9C—N2C	2.7 (2)
C8A—N1A—C10A—N2A	0.8 (2)	C7C—C8C—N1C—C10C	176.2 (2)
C8A—N1A—C10A—C11A	−179.90 (16)	C9C—C8C—N1C—C10C	−2.2 (3)
C9A—N2A—C10A—N1A	−1.1 (2)	N1CA—C8C—C9CA—O1CA	170 (4)
C12A—N2A—C10A—N1A	−179.79 (16)	C7C—C8C—C9CA—O1CA	−25 (5)
C9A—N2A—C10A—C11A	179.61 (16)	N1CA—C8C—C9CA—C10C	14 (2)
C12A—N2A—C10A—C11A	0.9 (3)	C7C—C8C—C9CA—C10C	179.1 (6)
C6B—C1B—C2B—C3B	−0.6 (2)	C7C—C8C—N1CA—N2C	179.7 (8)
C7B—C1B—C2B—C3B	−179.86 (16)	C9CA—C8C—N1CA—N2C	−14 (2)
C13B—O2B—C3B—C2B	−1.7 (3)	C10C—N2C—N1CA—C8C	7.8 (18)
C13B—O2B—C3B—C4B	178.10 (17)	C12C—N2C—N1CA—C8C	−178.5 (8)
C1B—C2B—C3B—O2B	−178.64 (16)	C8C—N1C—C10C—N2C	0.8 (3)
C1B—C2B—C3B—C4B	1.5 (3)	C8C—N1C—C10C—C11C	179.29 (18)
C14B—O3B—C4B—C5B	−68.5 (2)	C9C—N2C—C10C—N1C	1.0 (3)
C14B—O3B—C4B—C3B	115.49 (18)	C12C—N2C—C10C—N1C	−179.0 (2)
O2B—C3B—C4B—O3B	−4.2 (2)	C12C—N2C—C10C—C9CA	−172.4 (14)
C2B—C3B—C4B—O3B	175.62 (15)	N1CA—N2C—C10C—C9CA	2.3 (17)
O2B—C3B—C4B—C5B	179.64 (15)	C9C—N2C—C10C—C11C	−177.52 (18)
C2B—C3B—C4B—C5B	−0.5 (3)	C12C—N2C—C10C—C11C	2.4 (3)
C15B—O4B—C5B—C6B	−10.6 (2)	N1CA—N2C—C10C—C11C	177.1 (9)
C15B—O4B—C5B—C4B	172.43 (15)	O1CA—C9CA—C10C—N2C	−172 (2)
O3B—C4B—C5B—O4B	−0.4 (2)	C8C—C9CA—C10C—N2C	−8.3 (18)
C3B—C4B—C5B—O4B	175.63 (15)	O1CA—C9CA—C10C—C11C	13 (3)
O3B—C4B—C5B—C6B	−177.46 (15)	C8C—C9CA—C10C—C11C	176.7 (5)
C3B—C4B—C5B—C6B	−1.5 (3)	C6D—C1D—C2D—C3D	−1.4 (2)
O4B—C5B—C6B—C1B	−174.44 (15)	C7D—C1D—C2D—C3D	177.75 (16)
C4B—C5B—C6B—C1B	2.4 (2)	C13D—O2D—C3D—C2D	−1.2 (3)
C2B—C1B—C6B—C5B	−1.3 (2)	C13D—O2D—C3D—C4D	178.68 (17)
C7B—C1B—C6B—C5B	177.96 (15)	C1D—C2D—C3D—O2D	−179.35 (16)
C6B—C1B—C7B—C8B	179.21 (17)	C1D—C2D—C3D—C4D	0.8 (3)
C2B—C1B—C7B—C8B	−1.5 (3)	C14D—O3D—C4D—C5D	−71.0 (2)
C1B—C7B—C8B—N1B	−0.3 (3)	C14D—O3D—C4D—C3D	113.52 (18)
C1B—C7B—C8B—C9B	179.7 (2)	O2D—C3D—C4D—O3D	−3.3 (2)
C1B—C7B—C8B—C9BA	−12.0 (18)	C2D—C3D—C4D—O3D	176.56 (15)
C1B—C7B—C8B—N1BA	169.6 (9)	O2D—C3D—C4D—C5D	−178.87 (15)
N1B—C10B—N2B—C9B	0.9 (3)	C2D—C3D—C4D—C5D	1.0 (3)
C11B—C10B—N2B—C9B	179.6 (2)	C15D—O4D—C5D—C6D	3.0 (2)
C9BA—C10B—N2B—N1BA	−20.5 (19)	C15D—O4D—C5D—C4D	−175.32 (15)
C11B—C10B—N2B—N1BA	169.7 (9)	O3D—C4D—C5D—O4D	0.8 (2)
C9BA—C10B—N2B—C12B	169.7 (17)	C3D—C4D—C5D—O4D	176.24 (15)
N1B—C10B—N2B—C12B	−178.8 (2)	O3D—C4D—C5D—C6D	−177.62 (15)
C11B—C10B—N2B—C12B	−0.1 (3)	C3D—C4D—C5D—C6D	−2.2 (3)
N2B—C10B—N1B—C8B	−0.4 (3)	O4D—C5D—C6D—C1D	−176.71 (15)
C11B—C10B—N1B—C8B	−179.02 (17)	C4D—C5D—C6D—C1D	1.6 (2)
C7B—C8B—N1B—C10B	179.69 (19)	C2D—C1D—C6D—C5D	0.3 (2)
C9B—C8B—N1B—C10B	−0.3 (3)	C7D—C1D—C6D—C5D	−178.96 (15)
C10B—N2B—C9B—O1B	−175.8 (3)	C6D—C1D—C7D—C8D	−179.19 (17)
C12B—N2B—C9B—O1B	3.9 (4)	C2D—C1D—C7D—C8D	1.6 (3)
C10B—N2B—C9B—C8B	−1.0 (3)	C1D—C7D—C8D—N2D	−0.1 (3)
C12B—N2B—C9B—C8B	178.79 (17)	C1D—C7D—C8D—C9D	177.62 (16)
C7B—C8B—C9B—O1B	−4.6 (5)	C10D—N2D—C8D—C7D	177.74 (18)
N1B—C8B—C9B—O1B	175.3 (3)	C10D—N2D—C8D—C9D	−0.17 (18)
C7B—C8B—C9B—N2B	−179.19 (18)	C10D—N1D—C9D—O1D	−179.55 (18)
N1B—C8B—C9B—N2B	0.8 (3)	C12D—N1D—C9D—O1D	−2.2 (3)
N2B—C10B—C9BA—O1BA	179 (2)	C10D—N1D—C9D—C8D	0.42 (18)
C11B—C10B—C9BA—O1BA	−11 (4)	C12D—N1D—C9D—C8D	177.74 (16)
N2B—C10B—C9BA—C8B	16 (2)	C7D—C8D—C9D—O1D	1.7 (3)
C11B—C10B—C9BA—C8B	−174.0 (8)	N2D—C8D—C9D—O1D	179.81 (19)
C7B—C8B—C9BA—O1BA	13 (4)	C7D—C8D—C9D—N1D	−178.25 (16)
N1BA—C8B—C9BA—O1BA	−168 (3)	N2D—C8D—C9D—N1D	−0.16 (18)
C7B—C8B—C9BA—C10B	174.7 (8)	C8D—N2D—C10D—N1D	0.5 (2)
N1BA—C8B—C9BA—C10B	−7 (3)	C8D—N2D—C10D—C11D	−179.10 (16)
C10B—N2B—N1BA—C8B	13.0 (13)	C9D—N1D—C10D—N2D	−0.6 (2)
C12B—N2B—N1BA—C8B	−176.5 (5)	C12D—N1D—C10D—N2D	−177.86 (17)
C7B—C8B—N1BA—N2B	174.5 (6)	C9D—N1D—C10D—C11D	178.99 (16)
C9BA—C8B—N1BA—N2B	−4.2 (19)	C12D—N1D—C10D—C11D	1.7 (3)