X-ray studies on crystalline complexes involving amino acids and peptides. XXXVIII. Crystal structures of the complexes of L-arginine and L-histidine with glutaric acid and a comparative study of amino acid-glutaric acid complexes

The complexes of glutaric acid with L-arginine and L-histidine (two crystal forms) exhibit different stoichiometries and ionization states. The aggregation patterns in two of the crystals are remarkably similar to those observed earlier in similar structures, while the pattern in the remaining one has not been seen earlier. The variability in the ionization state and stoichiometry observed in amino acid-dicarboxylic acid complexes appears to represent subtle differences in the response of a molecule to the presence in its neighbourhood of another type of molecule. The glutaric acid molecules (or glutarate or semiglutarate ions) in their complexes and in other crystals favour a fully extended conformation, albeit with frequent departures from it. The change in the chirality of the component molecules in the complex could lead to drastic changes in the aggregation pattern; alternatively, the effects of the change are accommodated through small adjustments in essentially the same pattern.

Computing details

For all compounds, data collection: CAD4; cell refinement: CAD4. Data reduction: MolEN for (I); CAD4 for A, B. For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: ORTEP III. Software used to prepare material for publication: MSWORD for (I); MS WORD for A; MS Word for B.

Figures

(I)

Crystal data

<C9N4H21O5>	F(000) = 556
Mr = 516.57	Dx = 1.326 Mg m^−3
Monoclinic, C2	Cu Kα radiation, λ = 1.54180 Å
a = 19.008 (3) Å	Cell parameters from 25 reflections
b = 5.073 (2) Å	θ = 18–30°
c = 13.6723 (19) Å	µ = 0.92 mm^−1
β = 101.109 (13)°	T = 293 K
V = 1293.5 (6) Å^3	Needle, colourless
Z = 2	0.4 × 0.05 × 0.05 mm

Data collection

CAD4 diffractometer	1161 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
Graphite monochromator	θmax = 74.8°, θmin = 3.3°
ω–2/q scans	h = −5→23
Absorption correction: empirical (North et al., 1968) North et al., 1968	k = −6→6
Tmin = 0.955, Tmax = 1.000	l = −17→16
1545 measured reflections	2 standard reflections every 60 min
1494 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.053	w = 1/[σ^2(Fo^2) + (0.0833P)^2 + 0.7082P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.158	(Δ/σ)max = 0.005
S = 1.11	Δρmax = 0.23 e Å^−3
1494 reflections	Δρmin = −0.23 e Å^−3
170 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.0053 (9)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
N1	1.00235 (17)	0.9908 (8)	0.1336 (2)	0.0397 (8)
H1C	1.0318	0.9526	0.0923	0.060*
H1B	1.0277	1.0472	0.1914	0.060*
H1A	0.9720	1.1164	0.1068	0.060*
O1	0.90552 (14)	0.7840 (7)	−0.02090 (18)	0.0455 (8)
O2	0.91373 (17)	0.3883 (7)	0.0498 (2)	0.0532 (9)
C1	0.9249 (2)	0.6314 (9)	0.0507 (3)	0.0383 (9)
C2	0.96136 (19)	0.7502 (10)	0.1507 (3)	0.0389 (9)
H2	0.9941	0.6203	0.1881	0.047*
C3	0.9056 (2)	0.8325 (10)	0.2122 (3)	0.0474 (11)
H3A	0.9299	0.9267	0.2708	0.057*
H3B	0.8722	0.9542	0.1729	0.057*
C4	0.8631 (2)	0.6061 (11)	0.2458 (3)	0.0498 (11)
H4A	0.8365	0.5155	0.1878	0.060*
H4B	0.8959	0.4808	0.2841	0.060*
C5	0.8117 (2)	0.7062 (11)	0.3087 (3)	0.0525 (12)
H5A	0.7888	0.5580	0.3348	0.063*
H5B	0.8379	0.8054	0.3647	0.063*
N6	0.75720 (19)	0.8740 (9)	0.2502 (2)	0.0523 (10)
H6	0.7502	0.8595	0.1864	0.063*
C7	0.7174 (2)	1.0480 (11)	0.2878 (3)	0.0454 (11)
N8	0.72929 (19)	1.0978 (10)	0.3847 (2)	0.0543 (11)
H8A	0.7036	1.2129	0.4080	0.065*
H8B	0.7626	1.0150	0.4244	0.065*
N9	0.6655 (2)	1.1797 (11)	0.2292 (3)	0.0625 (13)
H9A	0.6407	1.2939	0.2543	0.075*
H9B	0.6568	1.1511	0.1660	0.075*
O11	0.64854 (18)	0.4798 (10)	0.4612 (2)	0.0666 (11)
O12	0.58634 (18)	0.5705 (11)	0.3129 (2)	0.0762 (14)
C13	0.5994 (2)	0.5996 (11)	0.4052 (3)	0.0494 (11)
C14	0.5511 (2)	0.7815 (13)	0.4511 (3)	0.0587 (13)
H14A	0.5239	0.8933	0.3998	0.070*
H14B	0.5801	0.8940	0.5004	0.070*
C15	0.5000	0.6198 (19)	0.5000	0.0588 (18)
H15A	0.526 (3)	0.467 (14)	0.549 (3)	0.071*
OW	0.72442 (17)	0.7589 (9)	0.0349 (2)	0.0602 (9)
H1W	0.673 (3)	0.781 (14)	0.006 (4)	0.090*
H2W	0.734 (3)	0.571 (15)	0.024 (4)	0.090*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0399 (15)	0.034 (2)	0.0432 (15)	−0.0008 (15)	0.0027 (11)	−0.0036 (16)
O1	0.0544 (15)	0.0421 (19)	0.0378 (12)	−0.0117 (15)	0.0030 (11)	0.0047 (14)
O2	0.0531 (16)	0.0356 (19)	0.0653 (19)	−0.0015 (15)	−0.0027 (13)	−0.0017 (16)
C1	0.0392 (17)	0.032 (2)	0.0438 (19)	−0.0011 (18)	0.0088 (14)	−0.0058 (19)
C2	0.0410 (18)	0.035 (2)	0.0402 (17)	0.0020 (19)	0.0054 (13)	0.0002 (19)
C3	0.054 (2)	0.045 (3)	0.0445 (19)	−0.001 (2)	0.0146 (16)	−0.006 (2)
C4	0.057 (2)	0.041 (3)	0.055 (2)	0.004 (2)	0.0186 (18)	0.004 (2)
C5	0.052 (2)	0.054 (3)	0.054 (2)	0.002 (2)	0.0152 (18)	0.006 (2)
N6	0.0516 (18)	0.063 (3)	0.0418 (16)	0.005 (2)	0.0085 (14)	0.0000 (18)
C7	0.0431 (19)	0.052 (3)	0.0414 (18)	−0.003 (2)	0.0094 (14)	0.002 (2)
N8	0.0532 (18)	0.067 (3)	0.0421 (16)	0.015 (2)	0.0074 (14)	0.0005 (18)
N9	0.058 (2)	0.082 (4)	0.0442 (17)	0.021 (2)	0.0029 (15)	−0.003 (2)
O11	0.0608 (17)	0.090 (3)	0.0464 (15)	0.014 (2)	0.0026 (12)	−0.011 (2)
O12	0.068 (2)	0.112 (4)	0.0435 (15)	0.013 (2)	−0.0010 (13)	−0.016 (2)
C13	0.0429 (19)	0.060 (3)	0.045 (2)	−0.006 (2)	0.0069 (15)	−0.008 (2)
C14	0.061 (3)	0.058 (3)	0.061 (2)	−0.001 (3)	0.021 (2)	−0.003 (3)
C15	0.060 (4)	0.061 (5)	0.061 (4)	0.000	0.025 (3)	0.000
OW	0.0531 (17)	0.059 (2)	0.0644 (18)	0.004 (2)	0.0010 (13)	−0.004 (2)

Geometric parameters (Å, º)

N1—C2	1.491 (6)	N6—C7	1.329 (6)
O1—C1	1.247 (5)	C7—N8	1.325 (5)
O2—C1	1.251 (6)	C7—N9	1.326 (6)
C1—C2	1.532 (5)	O11—C13	1.246 (6)
C2—C3	1.533 (5)	O12—C13	1.247 (5)
C3—C4	1.526 (7)	C13—C14	1.519 (7)
C4—C5	1.508 (6)	C14—C15	1.521 (7)
C5—N6	1.455 (6)	C15—C14^i	1.521 (7)
O1—C1—O2	125.5 (4)	C7—N6—C5	124.9 (3)
O1—C1—C2	118.1 (4)	N8—C7—N9	118.2 (4)
O2—C1—C2	116.3 (4)	N8—C7—N6	121.0 (4)
N1—C2—C1	110.0 (3)	N9—C7—N6	120.9 (4)
N1—C2—C3	107.5 (4)	O11—C13—O12	122.9 (5)
C1—C2—C3	110.8 (3)	O11—C13—C14	119.0 (4)
C4—C3—C2	115.0 (4)	O12—C13—C14	118.1 (4)
C5—C4—C3	110.9 (4)	C13—C14—C15	110.0 (5)
N6—C5—C4	110.7 (3)	C14^i—C15—C14	114.7 (7)
O1—C1—C2—N1	−31.3 (5)	C5—N6—C7—N8	5.9 (7)
O2—C1—C2—N1	152.5 (4)	C5—N6—C7—N9	−175.3 (5)
O1—C1—C2—C3	87.4 (5)	O11—C13—C14—C15	−73.6 (5)
O2—C1—C2—C3	−88.8 (5)	O12—C13—C14—C15	104.0 (5)
N1—C2—C3—C4	−174.3 (3)	C13—C14—C15—C14^i	179.8 (4)
C1—C2—C3—C4	65.4 (5)	H1A—N1—C2—H2	−172.6
C2—C3—C4—C5	177.9 (3)	H1B—N1—C2—C1	−173.0
C3—C4—C5—N6	64.9 (5)	H1C—N1—C2—C3	−173.7
C4—C5—N6—C7	−160.2 (5)	O11—C13—C14—C15	−73.6 (5)

Symmetry code: (i) −x+1, y, −z+1.

(A)

Crystal data

<C11H19N3O7>	Dx = 1.407 Mg m^−3
Mr = 1221.17	Cu Kα radiation, λ = 1.54180 Å
Orthorhombic, P212121	Cell parameters from 25 reflections
a = 8.335 (1) Å	θ = 10–30°
b = 8.856 (1) Å	µ = 1.01 mm^−1
c = 19.522 (2) Å	T = 293 K
V = 1441.0 (3) Å^3	Needle, colourless
Z = 4	0.56 × 0.38 × 0.06 mm
F(000) = 648

Data collection

CAD4 diffractometer	1295 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 74.9°, θmin = 4.5°
ω–2/q scans	h = 0→9
Absorption correction: cylinder (Dwiggins, 1975) Dwiggins JR Acta Cryst.(1975)A31,146-148	k = 0→11
Tmin = 0.844, Tmax = 0.848	l = 0→24
1609 measured reflections	3 standard reflections every 60 min
1609 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.055	w = 1/[σ^2(Fo^2) + (0.0698P)^2 + 0.3704P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.144	(Δ/σ)max = 0.004
S = 1.16	Δρmax = 0.24 e Å^−3
1609 reflections	Δρmin = −0.29 e Å^−3
199 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.028 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1	0.7051 (4)	0.9085 (4)	0.50718 (17)	0.0532 (9)
O2	0.9273 (5)	0.8547 (4)	0.44986 (19)	0.0631 (11)
N1	0.7349 (5)	0.6924 (4)	0.59850 (16)	0.0380 (9)
H1C	0.7450	0.7800	0.6209	0.057*
H1B	0.7567	0.6167	0.6267	0.057*
H1A	0.6349	0.6840	0.5830	0.057*
C1	0.8250 (6)	0.8305 (4)	0.4951 (2)	0.0367 (10)
C2	0.8485 (6)	0.6900 (4)	0.5399 (2)	0.0366 (10)
H2	0.9581	0.6912	0.5581	0.044*
C3	0.8258 (6)	0.5446 (4)	0.4981 (2)	0.0386 (10)
H3A	0.7144	0.5372	0.4841	0.046*
H3B	0.8907	0.5507	0.4570	0.046*
C4	0.8701 (6)	0.4062 (4)	0.53638 (19)	0.0348 (10)
N5	1.0285 (5)	0.3733 (4)	0.55244 (17)	0.0379 (9)
H5	1.1105	0.4266	0.5410	0.045*
C6	1.0327 (7)	0.2458 (5)	0.5883 (2)	0.0429 (11)
H6	1.1245	0.1993	0.6053	0.051*
N7	0.8853 (5)	0.1969 (4)	0.59576 (17)	0.0404 (9)
H7	0.8579	0.1159	0.6171	0.048*
C8	0.7822 (6)	0.2941 (5)	0.5645 (2)	0.0401 (10)
H8	0.6711	0.2850	0.5628	0.048*
O11	0.8000 (5)	−0.0486 (3)	0.66912 (15)	0.0499 (9)
O12	0.6558 (5)	−0.1515 (3)	0.75151 (17)	0.0592 (11)
C13	0.7153 (6)	−0.0394 (5)	0.7220 (2)	0.0404 (11)
C14	0.6840 (6)	0.1155 (5)	0.7516 (2)	0.0433 (11)
H14A	0.6037	0.1078	0.7874	0.052*
H14B	0.6420	0.1810	0.7161	0.052*
C15	0.8354 (7)	0.1842 (5)	0.7810 (2)	0.0449 (12)
H15A	0.9134	0.1968	0.7445	0.054*
H15B	0.8807	0.1155	0.8145	0.054*
C16	0.8047 (8)	0.3367 (4)	0.8148 (2)	0.0484 (13)
H16A	0.7137	0.3264	0.8455	0.058*
H16B	0.8973	0.3623	0.8425	0.058*
C17	0.7721 (6)	0.4652 (5)	0.7668 (2)	0.0406 (11)
O18	0.7879 (5)	0.4615 (3)	0.70578 (15)	0.0593 (11)
O19	0.7252 (6)	0.5867 (3)	0.80052 (16)	0.0605 (11)
H19	0.7036	0.6540	0.7732	0.091*
OW	0.8968 (6)	0.1499 (4)	0.39960 (19)	0.0595 (10)
H1W	0.899 (9)	0.138 (7)	0.352 (3)	0.089*
H2W	0.897 (9)	0.064 (8)	0.414 (3)	0.089*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.051 (2)	0.0405 (16)	0.068 (2)	0.0145 (17)	0.0090 (18)	0.0228 (16)
O2	0.071 (3)	0.053 (2)	0.065 (2)	0.0167 (19)	0.021 (2)	0.0304 (18)
N1	0.054 (2)	0.0244 (14)	0.0356 (16)	0.0018 (17)	0.0024 (17)	0.0039 (14)
C1	0.048 (3)	0.0243 (19)	0.038 (2)	−0.0014 (18)	−0.006 (2)	0.0042 (16)
C2	0.053 (3)	0.0253 (18)	0.0315 (18)	−0.001 (2)	−0.006 (2)	0.0047 (16)
C3	0.058 (3)	0.0285 (19)	0.0294 (18)	0.001 (2)	−0.003 (2)	0.0007 (16)
C4	0.051 (3)	0.0238 (17)	0.0296 (18)	−0.002 (2)	0.000 (2)	−0.0026 (15)
N5	0.046 (2)	0.0249 (16)	0.0423 (19)	−0.0007 (17)	0.0036 (17)	0.0045 (15)
C6	0.055 (3)	0.030 (2)	0.043 (2)	0.005 (2)	0.004 (2)	0.0062 (19)
N7	0.060 (3)	0.0222 (15)	0.0390 (18)	−0.0060 (18)	0.0061 (18)	0.0060 (15)
C8	0.051 (3)	0.030 (2)	0.040 (2)	−0.003 (2)	0.002 (2)	−0.0033 (17)
O11	0.082 (3)	0.0223 (13)	0.0449 (16)	−0.0039 (16)	0.0140 (18)	−0.0025 (12)
O12	0.094 (3)	0.0238 (14)	0.0592 (19)	−0.0012 (18)	0.026 (2)	0.0058 (14)
C13	0.059 (3)	0.0230 (19)	0.039 (2)	0.000 (2)	0.001 (2)	0.0012 (16)
C14	0.052 (3)	0.025 (2)	0.053 (2)	0.0017 (19)	0.004 (2)	−0.0024 (19)
C15	0.059 (3)	0.027 (2)	0.048 (2)	0.007 (2)	−0.004 (2)	−0.0005 (18)
C16	0.080 (4)	0.029 (2)	0.036 (2)	−0.001 (2)	−0.007 (2)	−0.0020 (17)
C17	0.060 (3)	0.0245 (19)	0.038 (2)	−0.004 (2)	−0.003 (2)	−0.0029 (17)
O18	0.108 (3)	0.0328 (15)	0.0368 (16)	0.004 (2)	0.001 (2)	−0.0013 (13)
O19	0.109 (3)	0.0277 (14)	0.0451 (17)	0.010 (2)	−0.003 (2)	−0.0039 (13)
OW	0.079 (3)	0.045 (2)	0.055 (2)	0.002 (2)	−0.003 (2)	0.0101 (17)

Geometric parameters (Å, º)

O1—C1	1.237 (5)	N7—C8	1.361 (6)
O2—C1	1.247 (5)	O11—C13	1.253 (5)
N1—C2	1.485 (5)	O12—C13	1.251 (5)
C1—C2	1.533 (5)	C13—C14	1.511 (6)
C2—C3	1.536 (5)	C14—C15	1.514 (7)
C3—C4	1.482 (5)	C15—C16	1.525 (6)
C4—C8	1.351 (6)	C16—C17	1.499 (5)
C4—N5	1.388 (6)	C17—O18	1.200 (5)
N5—C6	1.329 (5)	C17—O19	1.320 (5)
C6—N7	1.311 (7)
O1—C1—O2	126.2 (4)	C6—N7—C8	109.5 (4)
O1—C1—C2	116.6 (4)	C4—C8—N7	107.8 (4)
O2—C1—C2	117.2 (4)	O12—C13—O11	123.4 (4)
N1—C2—C1	110.1 (4)	O12—C13—C14	118.4 (4)
N1—C2—C3	110.2 (3)	O11—C13—C14	118.2 (4)
C1—C2—C3	111.2 (3)	C13—C14—C15	111.4 (4)
C4—C3—C2	113.3 (3)	C14—C15—C16	112.3 (4)
C8—C4—N5	105.6 (4)	C17—C16—C15	115.6 (3)
C8—C4—C3	132.7 (5)	O18—C17—O19	123.3 (4)
N5—C4—C3	121.6 (4)	O18—C17—C16	125.5 (4)
C6—N5—C4	108.8 (4)	O19—C17—C16	111.2 (3)
N7—C6—N5	108.3 (4)
O1—C1—C2—N1	−10.8 (5)	N5—C4—C8—N7	−0.5 (5)
O2—C1—C2—N1	169.8 (4)	C3—C4—C8—N7	−178.0 (4)
O1—C1—C2—C3	111.6 (5)	C6—N7—C8—C4	0.5 (5)
O2—C1—C2—C3	−67.8 (5)	O12—C13—C14—C15	111.6 (5)
N1—C2—C3—C4	−66.0 (5)	O11—C13—C14—C15	−68.2 (6)
C1—C2—C3—C4	171.7 (4)	C13—C14—C15—C16	−176.7 (3)
C2—C3—C4—C8	107.2 (5)	C14—C15—C16—C17	−72.8 (6)
C2—C3—C4—N5	−70.0 (5)	C15—C16—C17—O18	−9.8 (8)
C8—C4—N5—C6	0.4 (5)	C15—C16—C17—O19	171.3 (5)
C3—C4—N5—C6	178.2 (4)	H1A—N1—C2—H2	−175.2
C4—N5—C6—N7	0.0 (5)	H1B—N1—C2—C1	−173.6
N5—C6—N7—C8	−0.3 (5)	H1C—N1—C2—C3	−176.7

(B)

Crystal data

C34H52N12O16	Z = 2
Mr = 884.88	F(000) = 468
Triclinic, P1	Dx = 1.446 Mg m^−3
a = 5.791 (1) Å	Cu Kα radiation, λ = 1.54180 Å
b = 13.110 (3) Å	Cell parameters from 25 reflections
c = 14.360 (3) Å	θ = 10–30°
α = 110.46 (2)°	µ = 0.99 mm^−1
β = 89.78 (1)°	T = 293 K
γ = 95.62 (2)°	Platy, colourless
V = 1016.0 (4) Å^3	0.8 × 0.6 × 0.5 mm

Data collection

CAD4 diffractometer	4023 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 75.1°, θmin = 3.3°
ω–2/q scans	h = 0→7
Absorption correction: numerical (Dwiggins, 1975) Dwiggins JR Acta.Cryst 1975,A31,146	k = −16→16
Tmin = 0.604, Tmax = 0.629	l = −17→17
6281 measured reflections	3 standard reflections every 60 min
4174 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.042	w = 1/[σ^2(Fo^2) + (0.0853P)^2 + 0.1628P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.124	(Δ/σ)max < 0.001
S = 1.13	Δρmax = 0.33 e Å^−3
4174 reflections	Δρmin = −0.37 e Å^−3
566 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
3 restraints	Extinction coefficient: 0.0187 (17)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
N1	1.1322 (4)	0.0507 (2)	0.39355 (19)	0.0328 (5)
H1B	1.0082	0.0265	0.3525	0.049*
H1A	1.1867	0.1171	0.3951	0.049*
H1C	1.0925	0.0538	0.4544	0.049*
O1	1.5593 (4)	0.14124 (19)	0.40499 (18)	0.0421 (5)
O2	1.6890 (4)	−0.0052 (2)	0.2905 (2)	0.0448 (6)
C1	1.5420 (5)	0.0424 (2)	0.3496 (2)	0.0312 (6)
C2	1.3162 (5)	−0.0259 (2)	0.3577 (2)	0.0286 (5)
H2	1.3428	−0.0576	0.4087	0.034*
C3	1.2419 (5)	−0.1190 (3)	0.2621 (2)	0.0330 (6)
H3A	1.2103	−0.0893	0.2109	0.040*
H3B	1.3678	−0.1646	0.2405	0.040*
C4	1.0298 (5)	−0.1877 (2)	0.2744 (2)	0.0312 (6)
N5	0.9020 (5)	−0.2579 (2)	0.1928 (2)	0.0354 (5)
H5	0.9352	−0.2694	0.1318	0.042*
C6	0.7183 (6)	−0.3050 (3)	0.2238 (3)	0.0401 (7)
H6	0.6053	−0.3562	0.1828	0.048*
N7	0.7218 (5)	−0.2675 (2)	0.3221 (2)	0.0379 (6)
H7	0.6206	−0.2861	0.3587	0.046*
C8	0.9156 (6)	−0.1936 (3)	0.3556 (2)	0.0357 (6)
H8	0.9603	−0.1548	0.4216	0.043*
N11	0.6451 (4)	0.1831 (2)	0.20463 (19)	0.0310 (5)
H11C	0.6180	0.1194	0.2141	0.047*
H11B	0.7894	0.2120	0.2253	0.047*
H11A	0.6276	0.1722	0.1402	0.047*
O11	0.2110 (4)	0.09818 (19)	0.19774 (19)	0.0418 (5)
O12	0.0773 (4)	0.2554 (2)	0.2891 (2)	0.0502 (6)
C11	0.2348 (5)	0.1981 (3)	0.2481 (2)	0.0311 (6)
C12	0.4788 (5)	0.2589 (2)	0.2617 (2)	0.0289 (5)
H12	0.5252	0.2854	0.3324	0.035*
C13	0.4758 (5)	0.3572 (3)	0.2276 (3)	0.0365 (6)
H13A	0.4046	0.3320	0.1614	0.044*
H13B	0.3787	0.4085	0.2716	0.044*
C14	0.7085 (6)	0.4164 (2)	0.2257 (2)	0.0332 (6)
N15	0.8324 (5)	0.4821 (2)	0.3097 (2)	0.0358 (5)
H15	0.7910	0.4938	0.3698	0.043*
C16	1.0293 (6)	0.5250 (3)	0.2824 (3)	0.0394 (7)
H16	1.1433	0.5729	0.3257	0.047*
N17	1.0363 (5)	0.4889 (2)	0.1846 (2)	0.0376 (6)
H17	1.1461	0.5052	0.1502	0.045*
C18	0.8364 (6)	0.4204 (3)	0.1473 (2)	0.0366 (6)
H18	0.7962	0.3836	0.0804	0.044*
N21	1.0364 (4)	0.1714 (2)	0.91599 (18)	0.0304 (5)
H21A	1.0259	0.1311	0.8515	0.046*
H21C	1.0855	0.2404	0.9236	0.046*
H21B	0.8976	0.1689	0.9424	0.046*
O21	1.4886 (4)	0.1694 (2)	0.86203 (17)	0.0451 (6)
O22	1.6074 (4)	0.1685 (2)	1.00806 (17)	0.0406 (5)
C21	1.4536 (5)	0.1594 (2)	0.9435 (2)	0.0296 (5)
C22	1.2027 (5)	0.1280 (2)	0.9666 (2)	0.0289 (5)
H22	1.1826	0.1581	1.0386	0.035*
C23	1.1633 (5)	0.0026 (3)	0.9310 (3)	0.0373 (6)
H23A	1.1795	−0.0254	0.8595	0.045*
H23B	1.2866	−0.0229	0.9600	0.045*
C24	0.9364 (5)	−0.0474 (2)	0.9538 (2)	0.0339 (6)
N25	0.8733 (5)	−0.0390 (2)	1.0482 (2)	0.0360 (5)
H25	0.9488	−0.0003	1.1025	0.043*
C26	0.6709 (6)	−0.1026 (3)	1.0402 (3)	0.0385 (7)
H26	0.5929	−0.1115	1.0941	0.046*
N27	0.5981 (5)	−0.1504 (2)	0.9473 (2)	0.0386 (6)
C28	0.7637 (6)	−0.1157 (3)	0.8920 (3)	0.0380 (7)
H28	0.7582	−0.1360	0.8232	0.046*
N31	0.5204 (4)	0.0351 (2)	0.66261 (19)	0.0330 (5)
H31C	0.5316	−0.0365	0.6441	0.050*
H31B	0.3843	0.0460	0.6411	0.050*
H31A	0.5309	0.0649	0.7286	0.050*
O31	0.9685 (4)	0.0336 (2)	0.71857 (16)	0.0418 (5)
O32	1.0943 (4)	0.0404 (2)	0.57494 (18)	0.0438 (5)
C31	0.9412 (5)	0.0497 (2)	0.6399 (2)	0.0298 (5)
C32	0.7118 (5)	0.0866 (2)	0.6191 (2)	0.0296 (6)
H32	0.6842	0.0626	0.5470	0.036*
C33	0.7135 (6)	0.2117 (3)	0.6634 (3)	0.0381 (7)
H33A	0.5665	0.2315	0.6463	0.046*
H33B	0.7260	0.2345	0.7353	0.046*
C34	0.9050 (6)	0.2729 (3)	0.6289 (2)	0.0338 (6)
N35	0.9110 (5)	0.2754 (2)	0.5337 (2)	0.0383 (6)
H35	0.8087	0.2431	0.4867	0.046*
C36	1.1052 (7)	0.3371 (3)	0.5276 (3)	0.0430 (7)
H36	1.1487	0.3518	0.4707	0.052*
N37	1.2258 (6)	0.3741 (3)	0.6117 (2)	0.0465 (7)
C38	1.1006 (6)	0.3344 (3)	0.6758 (2)	0.0424 (7)
H38	1.1441	0.3480	0.7417	0.051*
O41	0.3625 (5)	0.5231 (3)	1.0737 (2)	0.0558 (7)
O42	0.1769 (5)	0.3925 (2)	0.9464 (2)	0.0571 (7)
C43	0.3421 (6)	0.4642 (3)	0.9825 (3)	0.0385 (7)
C44	0.5250 (6)	0.4836 (3)	0.9135 (3)	0.0446 (8)
H44A	0.4491	0.5005	0.8614	0.053*
H44B	0.5951	0.4161	0.8822	0.053*
C45	0.7182 (6)	0.5750 (3)	0.9622 (2)	0.0367 (6)
H45A	0.6492	0.6419	0.9974	0.044*
H45B	0.8038	0.5558	1.0105	0.044*
C46	0.8861 (6)	0.5959 (3)	0.8875 (3)	0.0417 (7)
H46A	0.9503	0.5281	0.8508	0.050*
H46B	0.8003	0.6169	0.8403	0.050*
C47	1.0839 (5)	0.6835 (2)	0.9334 (2)	0.0350 (6)
O48	1.1069 (5)	0.7359 (2)	1.02118 (19)	0.0497 (6)
O49	1.2310 (5)	0.6991 (2)	0.8683 (2)	0.0506 (6)
H49	1.3372	0.7452	0.8975	0.076*
O51	1.4102 (5)	0.6831 (3)	0.4302 (2)	0.0590 (8)
O52	1.5795 (5)	0.8291 (2)	0.5483 (3)	0.0640 (9)
C53	1.4250 (6)	0.7517 (3)	0.5182 (3)	0.0421 (7)
C54	1.2452 (7)	0.7355 (3)	0.5909 (3)	0.0511 (9)
H54A	1.3243	0.7213	0.6439	0.061*
H54B	1.1744	0.8031	0.6206	0.061*
C55	1.0551 (7)	0.6435 (3)	0.5456 (3)	0.0438 (8)
H55A	1.1246	0.5766	0.5112	0.053*
H55B	0.9652	0.6604	0.4970	0.053*
C56	0.8948 (7)	0.6253 (4)	0.6232 (3)	0.0520 (9)
H56A	0.9867	0.6096	0.6719	0.062*
H56B	0.8268	0.6928	0.6574	0.062*
C57	0.7019 (6)	0.5345 (3)	0.5834 (3)	0.0420 (7)
O58	0.6596 (5)	0.4840 (2)	0.49561 (19)	0.0512 (6)
O59	0.5838 (6)	0.5172 (3)	0.6544 (2)	0.0648 (9)
H59	0.4664	0.4759	0.6307	0.097*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0284 (12)	0.0358 (12)	0.0312 (12)	−0.0013 (9)	0.0036 (9)	0.0095 (10)
O1	0.0392 (12)	0.0397 (12)	0.0423 (12)	−0.0127 (9)	−0.0042 (10)	0.0124 (10)
O2	0.0257 (11)	0.0527 (14)	0.0559 (14)	−0.0006 (9)	0.0066 (10)	0.0203 (11)
C1	0.0261 (13)	0.0377 (14)	0.0324 (14)	−0.0059 (11)	−0.0037 (11)	0.0178 (11)
C2	0.0257 (13)	0.0318 (13)	0.0295 (13)	−0.0018 (10)	0.0002 (10)	0.0133 (11)
C3	0.0289 (14)	0.0342 (14)	0.0325 (14)	−0.0045 (11)	0.0053 (11)	0.0097 (12)
C4	0.0323 (15)	0.0270 (13)	0.0333 (14)	−0.0023 (11)	0.0028 (11)	0.0106 (11)
N5	0.0359 (13)	0.0333 (12)	0.0328 (13)	−0.0041 (10)	0.0022 (10)	0.0084 (10)
C6	0.0369 (16)	0.0343 (16)	0.0437 (17)	−0.0075 (12)	0.0013 (13)	0.0098 (13)
N7	0.0343 (14)	0.0335 (13)	0.0437 (14)	−0.0056 (10)	0.0068 (11)	0.0131 (11)
C8	0.0365 (16)	0.0330 (14)	0.0350 (14)	−0.0066 (12)	0.0024 (12)	0.0114 (12)
N11	0.0267 (12)	0.0332 (12)	0.0329 (12)	−0.0017 (9)	0.0034 (9)	0.0125 (9)
O11	0.0352 (11)	0.0382 (12)	0.0474 (13)	−0.0102 (9)	−0.0002 (9)	0.0128 (10)
O12	0.0251 (11)	0.0568 (15)	0.0568 (15)	−0.0001 (10)	0.0075 (10)	0.0064 (12)
C11	0.0268 (13)	0.0391 (15)	0.0267 (12)	−0.0031 (11)	0.0004 (10)	0.0125 (11)
C12	0.0246 (12)	0.0332 (13)	0.0274 (12)	−0.0006 (10)	0.0011 (10)	0.0095 (10)
C13	0.0313 (15)	0.0353 (15)	0.0448 (16)	0.0004 (12)	0.0015 (12)	0.0171 (13)
C14	0.0343 (15)	0.0255 (13)	0.0405 (15)	−0.0003 (11)	0.0029 (12)	0.0131 (11)
N15	0.0363 (14)	0.0312 (12)	0.0377 (13)	−0.0018 (10)	0.0034 (11)	0.0107 (10)
C16	0.0361 (16)	0.0316 (14)	0.0469 (18)	−0.0043 (12)	0.0031 (13)	0.0113 (13)
N17	0.0333 (13)	0.0336 (13)	0.0463 (15)	−0.0027 (10)	0.0054 (11)	0.0161 (11)
C18	0.0382 (16)	0.0322 (14)	0.0381 (15)	−0.0017 (12)	0.0034 (13)	0.0120 (12)
N21	0.0257 (11)	0.0326 (12)	0.0321 (12)	−0.0010 (9)	0.0022 (9)	0.0114 (9)
O21	0.0330 (11)	0.0695 (16)	0.0339 (11)	−0.0038 (10)	0.0065 (9)	0.0222 (11)
O22	0.0245 (10)	0.0636 (15)	0.0333 (10)	−0.0008 (9)	0.0006 (8)	0.0178 (10)
C21	0.0232 (12)	0.0335 (13)	0.0274 (13)	−0.0021 (10)	0.0031 (10)	0.0064 (10)
C22	0.0237 (13)	0.0345 (14)	0.0263 (12)	−0.0029 (10)	0.0026 (10)	0.0095 (10)
C23	0.0271 (14)	0.0333 (15)	0.0519 (18)	0.0018 (11)	0.0085 (12)	0.0157 (13)
C24	0.0290 (14)	0.0293 (13)	0.0422 (16)	−0.0002 (11)	0.0033 (12)	0.0121 (12)
N25	0.0325 (13)	0.0346 (13)	0.0388 (13)	−0.0017 (10)	0.0000 (10)	0.0118 (10)
C26	0.0355 (16)	0.0369 (15)	0.0451 (17)	−0.0003 (12)	0.0083 (13)	0.0180 (13)
N27	0.0308 (13)	0.0333 (13)	0.0496 (15)	−0.0043 (10)	0.0028 (11)	0.0139 (11)
C28	0.0364 (16)	0.0362 (15)	0.0390 (15)	−0.0009 (13)	0.0033 (12)	0.0115 (12)
N31	0.0260 (12)	0.0383 (13)	0.0333 (12)	−0.0040 (9)	0.0030 (9)	0.0126 (10)
O31	0.0400 (12)	0.0582 (14)	0.0290 (10)	0.0074 (10)	0.0003 (9)	0.0169 (10)
O32	0.0266 (11)	0.0695 (16)	0.0380 (11)	0.0075 (10)	0.0095 (9)	0.0219 (11)
C31	0.0251 (12)	0.0354 (14)	0.0262 (12)	−0.0003 (10)	−0.0003 (10)	0.0082 (10)
C32	0.0238 (13)	0.0356 (14)	0.0273 (12)	−0.0030 (10)	0.0030 (10)	0.0101 (11)
C33	0.0328 (15)	0.0361 (15)	0.0460 (17)	0.0037 (12)	0.0105 (13)	0.0150 (13)
C34	0.0346 (15)	0.0322 (14)	0.0343 (14)	0.0004 (11)	0.0010 (11)	0.0120 (11)
N35	0.0408 (14)	0.0345 (13)	0.0365 (13)	−0.0065 (11)	−0.0028 (11)	0.0112 (11)
C36	0.0480 (19)	0.0375 (16)	0.0409 (17)	−0.0061 (13)	0.0078 (14)	0.0134 (13)
N37	0.0438 (16)	0.0446 (15)	0.0453 (15)	−0.0130 (12)	0.0038 (13)	0.0131 (12)
C38	0.0392 (17)	0.0469 (18)	0.0351 (15)	−0.0068 (14)	−0.0004 (13)	0.0098 (13)
O41	0.0436 (14)	0.0689 (18)	0.0446 (14)	−0.0248 (13)	0.0047 (11)	0.0151 (13)
O42	0.0447 (15)	0.0421 (13)	0.0728 (19)	−0.0178 (11)	0.0027 (13)	0.0117 (13)
C43	0.0334 (15)	0.0315 (14)	0.0498 (18)	−0.0041 (12)	−0.0009 (13)	0.0151 (13)
C44	0.0416 (18)	0.0384 (16)	0.0444 (17)	−0.0105 (14)	0.0048 (14)	0.0068 (13)
C45	0.0372 (16)	0.0325 (14)	0.0371 (15)	−0.0057 (12)	0.0029 (12)	0.0104 (12)
C46	0.0395 (17)	0.0415 (17)	0.0378 (15)	−0.0077 (13)	0.0068 (13)	0.0093 (13)
C47	0.0322 (15)	0.0341 (15)	0.0376 (15)	0.0005 (12)	0.0066 (12)	0.0121 (12)
O48	0.0493 (15)	0.0530 (14)	0.0366 (12)	−0.0165 (11)	0.0052 (11)	0.0088 (11)
O49	0.0439 (14)	0.0543 (15)	0.0426 (13)	−0.0162 (11)	0.0108 (11)	0.0090 (11)
O51	0.0546 (16)	0.0636 (17)	0.0453 (14)	−0.0256 (13)	0.0125 (12)	0.0108 (12)
O52	0.0533 (17)	0.0445 (14)	0.0728 (19)	−0.0192 (12)	0.0193 (15)	0.0005 (13)
C53	0.0374 (17)	0.0369 (16)	0.0483 (18)	−0.0068 (13)	0.0056 (14)	0.0134 (14)
C54	0.045 (2)	0.054 (2)	0.0432 (18)	−0.0159 (16)	0.0091 (15)	0.0086 (15)
C55	0.0434 (19)	0.0433 (17)	0.0408 (17)	−0.0088 (14)	0.0074 (14)	0.0136 (14)
C56	0.047 (2)	0.059 (2)	0.0396 (17)	−0.0201 (17)	0.0069 (15)	0.0102 (15)
C57	0.0396 (17)	0.0454 (18)	0.0382 (16)	−0.0062 (14)	0.0059 (13)	0.0143 (14)
O58	0.0527 (15)	0.0540 (15)	0.0405 (13)	−0.0148 (12)	0.0032 (11)	0.0140 (11)
O59	0.0574 (18)	0.083 (2)	0.0423 (14)	−0.0352 (16)	0.0057 (13)	0.0184 (14)

Geometric parameters (Å, º)

N1—C2	1.501 (4)	N25—C26	1.351 (4)
O1—C1	1.255 (4)	C26—N27	1.312 (5)
O2—C1	1.250 (4)	N27—C28	1.385 (4)
C1—C2	1.538 (4)	N31—C32	1.490 (4)
C2—C3	1.513 (4)	O31—C31	1.233 (4)
C3—C4	1.498 (4)	O32—C31	1.267 (4)
C4—C8	1.359 (4)	C31—C32	1.522 (4)
C4—N5	1.374 (4)	C32—C33	1.537 (4)
N5—C6	1.331 (4)	C33—C34	1.489 (4)
C6—N7	1.322 (5)	C34—C38	1.355 (5)
N7—C8	1.377 (4)	C34—N35	1.380 (4)
N11—C12	1.483 (4)	N35—C36	1.341 (4)
O11—C11	1.250 (4)	C36—N37	1.309 (5)
O12—C11	1.250 (4)	N37—C38	1.379 (5)
C11—C12	1.530 (4)	O41—C43	1.266 (5)
C12—C13	1.531 (4)	O42—C43	1.247 (4)
C13—C14	1.493 (4)	C43—C44	1.511 (5)
C14—C18	1.359 (5)	C44—C45	1.528 (4)
C14—N15	1.368 (4)	C45—C46	1.521 (4)
N15—C16	1.340 (4)	C46—C47	1.512 (5)
C16—N17	1.317 (5)	C47—O48	1.207 (4)
N17—C18	1.378 (4)	C47—O49	1.317 (4)
N21—C22	1.477 (4)	O51—C53	1.266 (5)
O21—C21	1.236 (4)	O52—C53	1.239 (5)
O22—C21	1.255 (4)	C53—C54	1.524 (5)
C21—C22	1.537 (4)	C54—C55	1.512 (5)
C22—C23	1.535 (4)	C55—C56	1.514 (5)
C23—C24	1.497 (4)	C56—C57	1.504 (5)
C24—C28	1.366 (5)	C57—O58	1.214 (5)
C24—N25	1.372 (4)	C57—O59	1.298 (4)
O2—C1—O1	126.8 (3)	N25—C24—C23	123.5 (3)
O2—C1—C2	117.7 (3)	C26—N25—C24	107.5 (3)
O1—C1—C2	115.5 (3)	N27—C26—N25	111.7 (3)
N1—C2—C3	112.0 (2)	C26—N27—C28	105.4 (3)
N1—C2—C1	107.8 (2)	C24—C28—N27	109.9 (3)
C3—C2—C1	113.6 (2)	O31—C31—O32	124.5 (3)
C4—C3—C2	112.1 (2)	O31—C31—C32	118.8 (3)
C8—C4—N5	106.4 (3)	O32—C31—C32	116.7 (3)
C8—C4—C3	132.9 (3)	N31—C32—C31	109.2 (2)
N5—C4—C3	120.6 (3)	N31—C32—C33	109.2 (2)
C6—N5—C4	108.7 (3)	C31—C32—C33	111.7 (2)
N7—C6—N5	109.2 (3)	C34—C33—C32	114.3 (2)
C6—N7—C8	108.2 (3)	C38—C34—N35	105.2 (3)
C4—C8—N7	107.5 (3)	C38—C34—C33	131.8 (3)
O11—C11—O12	126.5 (3)	N35—C34—C33	123.0 (3)
O11—C11—C12	118.1 (3)	C36—N35—C34	107.7 (3)
O12—C11—C12	115.4 (3)	N37—C36—N35	111.4 (3)
N11—C12—C11	109.7 (2)	C36—N37—C38	105.6 (3)
N11—C12—C13	111.3 (2)	C34—C38—N37	110.1 (3)
C11—C12—C13	109.4 (2)	O42—C43—O41	123.4 (3)
C14—C13—C12	115.0 (3)	O42—C43—C44	118.4 (3)
C18—C14—N15	106.6 (3)	O41—C43—C44	118.2 (3)
C18—C14—C13	130.1 (3)	C43—C44—C45	115.6 (3)
N15—C14—C13	123.3 (3)	C46—C45—C44	112.8 (3)
C16—N15—C14	108.4 (3)	C47—C46—C45	114.3 (3)
N17—C16—N15	109.4 (3)	O48—C47—O49	122.2 (3)
C16—N17—C18	107.9 (3)	O48—C47—C46	124.1 (3)
C14—C18—N17	107.7 (3)	O49—C47—C46	113.8 (3)
O21—C21—O22	125.4 (3)	O52—C53—O51	123.6 (3)
O21—C21—C22	117.8 (3)	O52—C53—C54	118.8 (3)
O22—C21—C22	116.7 (2)	O51—C53—C54	117.6 (3)
N21—C22—C23	110.7 (2)	C55—C54—C53	114.8 (3)
N21—C22—C21	110.6 (2)	C54—C55—C56	112.1 (3)
C23—C22—C21	107.6 (2)	C57—C56—C55	115.0 (3)
C24—C23—C22	117.4 (2)	O58—C57—O59	123.9 (3)
C28—C24—N25	105.5 (3)	O58—C57—C56	124.4 (3)
C28—C24—C23	130.8 (3)	O59—C57—C56	111.7 (3)
O2—C1—C2—N1	−155.4 (3)	O31—C31—C32—N31	−34.1 (4)
O1—C1—C2—N1	25.4 (3)	O32—C31—C32—N31	147.7 (3)
O2—C1—C2—C3	−30.6 (4)	O31—C31—C32—C33	86.8 (3)
O1—C1—C2—C3	150.2 (3)	O32—C31—C32—C33	−91.4 (3)
N1—C2—C3—C4	−61.0 (3)	N31—C32—C33—C34	177.3 (3)
C1—C2—C3—C4	176.5 (2)	C31—C32—C33—C34	56.5 (4)
C2—C3—C4—C8	−12.1 (5)	C32—C33—C34—C38	−108.5 (4)
C2—C3—C4—N5	163.5 (3)	C32—C33—C34—N35	71.3 (4)
C8—C4—N5—C6	−0.5 (4)	C38—C34—N35—C36	−0.1 (4)
C3—C4—N5—C6	−177.1 (3)	C33—C34—N35—C36	−180.0 (3)
C4—N5—C6—N7	0.4 (4)	C34—N35—C36—N37	0.4 (4)
N5—C6—N7—C8	−0.1 (4)	N35—C36—N37—C38	−0.5 (4)
N5—C4—C8—N7	0.4 (3)	N35—C34—C38—N37	−0.2 (4)
C3—C4—C8—N7	176.4 (3)	C33—C34—C38—N37	179.7 (3)
C6—N7—C8—C4	−0.2 (4)	C36—N37—C38—C34	0.4 (4)
O11—C11—C12—N11	2.9 (4)	O42—C43—C44—C45	178.2 (3)
O12—C11—C12—N11	−176.6 (3)	O41—C43—C44—C45	−0.6 (5)
O11—C11—C12—C13	125.1 (3)	C43—C44—C45—C46	−175.7 (3)
O12—C11—C12—C13	−54.4 (4)	C44—C45—C46—C47	−178.2 (3)
N11—C12—C13—C14	−51.9 (4)	C45—C46—C47—O48	−2.1 (5)
C11—C12—C13—C14	−173.2 (3)	C45—C46—C47—O49	178.5 (3)
C12—C13—C14—C18	108.6 (4)	O52—C53—C54—C55	176.2 (4)
C12—C13—C14—N15	−73.0 (4)	O51—C53—C54—C55	−5.3 (6)
C18—C14—N15—C16	0.4 (3)	C53—C54—C55—C56	175.0 (4)
C13—C14—N15—C16	−178.4 (3)	C54—C55—C56—C57	−179.7 (4)
C14—N15—C16—N17	−0.3 (4)	C55—C56—C57—O58	−6.3 (6)
N15—C16—N17—C18	0.2 (4)	C55—C56—C57—O59	174.4 (4)
N15—C14—C18—N17	−0.2 (3)	H1A—N1—C2—H2	123.2
C13—C14—C18—N17	178.4 (3)	H1B—N1—C2—C1	127.2
C16—N17—C18—C14	0.0 (4)	H1C—N1—C2—C3	121.5
O21—C21—C22—N21	−30.7 (4)	H1A—N1—C2—C1	7.2
O22—C21—C22—N21	152.1 (3)	H1B—N1—C2—C3	1.5
O21—C21—C22—C23	90.2 (3)	H1C—N1—C2—H2	3.2
O22—C21—C22—C23	−87.0 (3)	H1A—N1—C2—C3	−118.5
N21—C22—C23—C24	−64.3 (4)	H1B—N1—C2—H2	−116.8
C21—C22—C23—C24	174.8 (3)	H1C—N1—C2—C1	−112.8
C22—C23—C24—C28	118.7 (4)	H11A—N11—C12—H12	−165.4
C22—C23—C24—N25	−68.1 (4)	H11B—N11—C12—C11	−164.3
C28—C24—N25—C26	1.0 (3)	H11C—N11—C12—C13	−165.4
C23—C24—N25—C26	−173.7 (3)	H21A—N21—C22—H22	−164.3
C24—N25—C26—N27	−0.7 (4)	H21B—N21—C22—C21	−164.7
N25—C26—N27—C28	0.2 (4)	H21C—N21—C22—C23	−163.8
N25—C24—C28—N27	−0.9 (4)	H31A—N31—C32—H32	−170.5
C23—C24—C28—N27	173.2 (3)	H31B—N31—C32—C31	−169.3
C26—N27—C28—C24	0.5 (4)	H31C—N31—C32—C33	−171.7