Disappearance of intramolecular stacking due to one-atom movement or increment of a `propyl­ene linker' in pyrazolo­[3,4-d]­pyrimidine-based ­flexible models

In the crystal structures of 4,6-di­methyl­thio-1-[3-(4,6-di­methyl­thio-2H-pyra­zolo­[3,4-d]­py­rimi­din-2-yl)­propyl]-1H-py­ra­­zolo­[3,4-d]­py­rimi­dine, C₁₇H₂₀N₈S₄, and 1-[4-(4-meth­oxy-6-methyl­thio-1H-pyra­zolo­[3,4-d]py­rimi­din-1-yl)­butyl]-5-meth­yl-6-methyl­thio-4,5-di­hydro-1H-pyra­zolo­[3,4-d]py­rimi­din-4-one, C₁₈H₂₂N₈O₂S₂, only intermolecular stacking due to aromatic [pi]-[pi] interactions between pyrazolo­[3,4-d]­pyrimidinerings is present.

Computing details

For both compounds, data collection: XSCANS (Siemens, 1992); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990). Program(s) used to refine structure: SHELXL93 (Sheldrick, 1993) for (4); SHELXL97 (Sheldrick, 1997) for (5). For both compounds, molecular graphics: NRCVAX (Gabe et al., 1989). Software used to prepare material for publication: SHELXL93 for (4); SHELXL97 for (5).

(4) 1-[4,6-dimethylthio-2H-pyrazolo[3,4-d]pyrimidin-2-yl]-4,6-dimethylthio-1H- pyrazolo[3,4-d]pyrimidine

Crystal data

C17H20N8S4	Dx = 1.465 Mg m^−3
Mr = 464.65	Melting point: 180 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.620 (2) Å	Cell parameters from 42 reflections
b = 10.411 (2) Å	θ = 4.7–13.1°
c = 26.813 (5) Å	µ = 0.47 mm^−1
β = 97.92 (2)°	T = 293 K
V = 2106.8 (8) Å^3	Rhombehedral, colourless
Z = 4	0.5 × 0.5 × 0.5 mm
F(000) = 968

Data collection

Siemens P4 diffractometer	2893 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 25.0°, θmin = 2.1°
ω–scan	h = 0→9
Absorption correction: ψ scan (local program; Karcher, 1981)	k = 0→12
Tmin = 0.749, Tmax = 0.778	l = −31→31
3697 measured reflections	3 standard reflections every 97 reflections
3697 independent reflections	intensity decay: nil

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.142	Calculated w = 1/[σ^2(Fo^2) + (0.1195P)^2 + 1.4563P] where P = (Fo^2 + 2Fc^2)/3
S = 0.84	(Δ/σ)max < 0.001
3684 reflections	Δρmax = 0.50 e Å^−3
267 parameters	Δρmin = −0.24 e Å^−3
0 restraints	Extinction correction: SHELXL93 (Sheldrick, 1993), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0066 (12)

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 on F² for ALL reflections except for 13 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor(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.

All the H atoms were placed in geometrical idealized positions and allowed to ride on their parent atoms, to which each was bonded for the final cycles of refinement.

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

	x	y	z	Uiso*/Ueq
N1	0.6765 (3)	0.7323 (2)	0.27058 (10)	0.0567 (6)
N2	0.6687 (3)	0.6147 (2)	0.24806 (9)	0.0546 (6)
C3	0.6296 (4)	0.5188 (3)	0.27724 (11)	0.0552 (7)
H3	0.6191 (4)	0.4323 (3)	0.26873 (11)	0.066*
C3A	0.6076 (4)	0.5743 (3)	0.32313 (11)	0.0519 (6)
C4	0.5678 (4)	0.5361 (3)	0.37090 (11)	0.0546 (7)
S4	0.52861 (13)	0.37328 (8)	0.38199 (3)	0.0668 (3)
CS4	0.5173 (7)	0.3728 (4)	0.44831 (14)	0.0915 (13)
HS4A	0.476 (4)	0.2907 (12)	0.4580 (3)	0.137*
HS4B	0.437 (4)	0.439 (2)	0.4561 (2)	0.137*
HS4C	0.6330 (11)	0.389 (3)	0.46636 (14)	0.137*
N5	0.5591 (4)	0.6212 (3)	0.40670 (9)	0.0586 (6)
C6	0.5897 (4)	0.7470 (3)	0.39526 (12)	0.0571 (7)
S6	0.57146 (15)	0.84538 (9)	0.44724 (3)	0.0769 (3)
CS6	0.5919 (6)	1.0034 (4)	0.4224 (2)	0.0850 (11)
HS6A	0.7103 (13)	1.0157 (11)	0.4148 (11)	0.128*
HS6B	0.567 (4)	1.0659 (4)	0.4467 (5)	0.128*
HS6C	0.509 (3)	1.0134 (11)	0.3921 (7)	0.128*
N7	0.6293 (3)	0.7968 (2)	0.35316 (9)	0.0562 (6)
C7A	0.6375 (4)	0.7067 (3)	0.31652 (11)	0.0517 (6)
N1'	0.3980 (3)	0.5145 (2)	0.11726 (9)	0.0553 (6)
N2'	0.4251 (4)	0.5241 (3)	0.06768 (9)	0.0641 (7)
C3'	0.4362 (5)	0.4053 (3)	0.05171 (11)	0.0626 (8)
H3'	0.4538 (5)	0.3832 (3)	0.01917 (11)	0.075*
C3'A	0.4178 (4)	0.3152 (3)	0.09027 (10)	0.0522 (6)
C4'	0.4195 (4)	0.1828 (3)	0.09828 (10)	0.0505 (6)
S4'	0.44824 (14)	0.08063 (8)	0.04922 (3)	0.0700 (3)
CS4'	0.4605 (6)	−0.0718 (3)	0.07966 (14)	0.0786 (10)
HS4D	0.5710 (18)	−0.0788 (12)	0.1015 (9)	0.118*
HS4E	0.453 (4)	−0.1387 (3)	0.0548 (2)	0.118*
HS4F	0.364 (2)	−0.0802 (12)	0.0991 (9)	0.118*
N5'	0.3991 (3)	0.1360 (2)	0.14339 (8)	0.0519 (6)
C6'	0.3743 (4)	0.2208 (3)	0.18009 (10)	0.0506 (6)
S6'	0.34088 (11)	0.15980 (7)	0.23887 (3)	0.0592 (3)
CS6'	0.3691 (5)	−0.0101 (3)	0.23178 (13)	0.0671 (8)
HS6D	0.348 (4)	−0.0531 (4)	0.2620 (4)	0.101*
HS6E	0.4878 (11)	−0.0275 (4)	0.2255 (10)	0.101*
HS6F	0.287 (2)	−0.0407 (5)	0.2040 (6)	0.101*
N7'	0.3715 (3)	0.3477 (2)	0.17775 (9)	0.0521 (6)
C7'A	0.3946 (4)	0.3903 (3)	0.13179 (10)	0.0505 (6)
C8	0.7079 (4)	0.6063 (3)	0.19635 (11)	0.0606 (7)
H8A	0.7015 (4)	0.5172 (3)	0.18565 (11)	0.073*
H8B	0.8277 (4)	0.6364 (3)	0.19510 (11)	0.073*
C9	0.5800 (4)	0.6852 (3)	0.16051 (11)	0.0591 (7)
H9A	0.5692 (4)	0.7696 (3)	0.17511 (11)	0.071*
H9B	0.6297 (4)	0.6966 (3)	0.12940 (11)	0.071*
C10	0.3986 (4)	0.6287 (3)	0.14827 (12)	0.0600 (8)
H10A	0.3537 (4)	0.6070 (3)	0.17934 (12)	0.072*
H10B	0.3200 (4)	0.6923 (3)	0.13074 (12)	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.078 (2)	0.0427 (12)	0.0505 (13)	−0.0017 (11)	0.0118 (11)	−0.0015 (10)
N2	0.0745 (15)	0.0433 (12)	0.0470 (13)	0.0038 (11)	0.0115 (11)	−0.0036 (10)
C3	0.073 (2)	0.0432 (14)	0.0488 (15)	0.0018 (13)	0.0060 (13)	−0.0006 (12)
C3A	0.063 (2)	0.0458 (15)	0.0463 (14)	0.0005 (12)	0.0051 (12)	0.0002 (11)
C4	0.063 (2)	0.050 (2)	0.050 (2)	−0.0019 (13)	0.0050 (12)	0.0020 (12)
S4	0.0962 (6)	0.0473 (5)	0.0581 (5)	−0.0031 (4)	0.0150 (4)	0.0050 (3)
CS4	0.142 (4)	0.079 (3)	0.055 (2)	−0.008 (2)	0.016 (2)	0.016 (2)
N5	0.074 (2)	0.0537 (14)	0.0487 (13)	−0.0033 (12)	0.0112 (11)	−0.0025 (11)
C6	0.068 (2)	0.052 (2)	0.052 (2)	−0.0037 (13)	0.0099 (13)	−0.0053 (13)
S6	0.1145 (8)	0.0630 (6)	0.0581 (5)	−0.0143 (5)	0.0293 (5)	−0.0147 (4)
CS6	0.121 (3)	0.056 (2)	0.082 (2)	−0.009 (2)	0.029 (2)	−0.014 (2)
N7	0.0728 (15)	0.0464 (13)	0.0503 (13)	−0.0019 (11)	0.0118 (11)	−0.0058 (11)
C7A	0.060 (2)	0.0452 (15)	0.0499 (15)	−0.0013 (12)	0.0082 (12)	−0.0018 (12)
N1'	0.075 (2)	0.0464 (13)	0.0457 (12)	−0.0013 (11)	0.0110 (11)	0.0057 (10)
N2'	0.098 (2)	0.0514 (14)	0.0431 (13)	−0.0026 (13)	0.0110 (13)	0.0074 (11)
C3'	0.095 (2)	0.054 (2)	0.0391 (14)	−0.006 (2)	0.0089 (14)	0.0025 (12)
C3'A	0.070 (2)	0.0463 (15)	0.0404 (13)	−0.0007 (12)	0.0081 (12)	0.0034 (11)
C4'	0.066 (2)	0.0481 (15)	0.0384 (13)	−0.0036 (12)	0.0094 (11)	0.0003 (11)
S4'	0.1196 (8)	0.0501 (5)	0.0433 (4)	0.0001 (4)	0.0217 (4)	−0.0020 (3)
CS4'	0.123 (3)	0.053 (2)	0.066 (2)	0.002 (2)	0.034 (2)	0.002 (2)
N5'	0.0686 (14)	0.0491 (13)	0.0392 (12)	−0.0038 (11)	0.0117 (10)	0.0003 (10)
C6'	0.0591 (15)	0.051 (2)	0.0419 (14)	−0.0044 (12)	0.0099 (11)	0.0046 (11)
S6'	0.0832 (5)	0.0554 (5)	0.0419 (4)	0.0003 (4)	0.0195 (3)	0.0077 (3)
CS6'	0.093 (2)	0.053 (2)	0.059 (2)	−0.001 (2)	0.022 (2)	0.0131 (14)
N7'	0.0699 (15)	0.0465 (13)	0.0418 (12)	0.0016 (11)	0.0145 (10)	0.0033 (9)
C7'A	0.064 (2)	0.0465 (14)	0.0411 (13)	0.0025 (12)	0.0066 (11)	0.0034 (11)
C8	0.079 (2)	0.057 (2)	0.047 (2)	0.0041 (15)	0.0140 (14)	−0.0043 (13)
C9	0.092 (2)	0.0400 (14)	0.048 (2)	−0.0001 (14)	0.0184 (14)	0.0036 (12)
C10	0.081 (2)	0.046 (2)	0.055 (2)	0.0105 (14)	0.0164 (14)	0.0041 (13)

Geometric parameters (Å, º)

N1—C7A	1.333 (4)	C3'—C3'A	1.417 (4)
N1—N2	1.363 (3)	C3'—H3'	0.93
N2—C3	1.327 (4)	C3'A—C4'	1.395 (4)
N2—C8	1.461 (4)	C3'A—C7'A	1.391 (4)
C3—C3A	1.390 (4)	C4'—N5'	1.333 (3)
C3—H3	0.93	C4'—S4'	1.729 (3)
C3A—C7A	1.412 (4)	S4'—CS4'	1.782 (4)
C3A—C4	1.413 (4)	CS4'—HS4D	0.96
C4—N5	1.315 (4)	CS4'—HS4E	0.96
C4—S4	1.754 (3)	CS4'—HS4F	0.96
S4—CS4	1.792 (4)	N5'—C6'	1.355 (4)
CS4—HS4A	0.96	C6'—N7'	1.323 (4)
CS4—HS4B	0.96	C6'—S6'	1.750 (3)
CS4—HS4C	0.96	S6'—CS6'	1.795 (3)
N5—C6	1.372 (4)	CS6'—HS6D	0.96
C6—N7	1.314 (4)	CS6'—HS6E	0.96
C6—S6	1.750 (3)	CS6'—HS6F	0.96
S6—CS6	1.790 (4)	N7'—C7'A	1.344 (3)
CS6—HS6A	0.96	C8—C9	1.513 (4)
CS6—HS6B	0.96	C8—H8A	0.97
CS6—HS6C	0.96	C8—H8B	0.97
N7—C7A	1.366 (4)	C9—C10	1.496 (5)
N1'—C7'A	1.352 (4)	C9—H9A	0.97
N1'—N2'	1.377 (3)	C9—H9B	0.97
N1'—C10	1.450 (4)	C10—H10A	0.97
N2'—C3'	1.315 (4)	C10—H10B	0.97
C7A—N1—N2	103.2 (2)	C7'A—C3'A—C3'	104.4 (3)
C3—N2—N1	114.5 (2)	N5'—C4'—C3'A	120.1 (3)
C3—N2—C8	127.3 (2)	N5'—C4'—S4'	120.5 (2)
N1—N2—C8	118.2 (2)	C3'A—C4'—S4'	119.4 (2)
N2—C3—C3A	105.9 (3)	C4'—S4'—CS4'	101.8 (2)
N2—C3—H3	127.1 (2)	S4'—CS4'—HS4D	109.5 (2)
C3A—C3—H3	127.1 (2)	S4'—CS4'—HS4E	109.47 (12)
C3—C3A—C7A	104.7 (3)	HS4D—CS4'—HS4E	109.5
C3—C3A—C4	138.8 (3)	S4'—CS4'—HS4F	109.47 (13)
C7A—C3A—C4	116.5 (3)	HS4D—CS4'—HS4F	109.5
N5—C4—C3A	120.7 (3)	HS4E—CS4'—HS4F	109.5
N5—C4—S4	120.0 (2)	C4'—N5'—C6'	117.8 (2)
C3A—C4—S4	119.2 (2)	N7'—C6'—N5'	128.3 (3)
C4—S4—CS4	101.7 (2)	N7'—C6'—S6'	113.7 (2)
S4—CS4—HS4A	109.47 (14)	N5'—C6'—S6'	118.0 (2)
S4—CS4—HS4B	109.5 (2)	C6'—S6'—CS6'	103.2 (2)
HS4A—CS4—HS4B	109.5	S6'—CS6'—HS6D	109.47 (11)
S4—CS4—HS4C	109.5 (2)	S6'—CS6'—HS6E	109.47 (12)
HS4A—CS4—HS4C	109.5	HS6D—CS6'—HS6E	109.5
HS4B—CS4—HS4C	109.5	S6'—CS6'—HS6F	109.47 (12)
C4—N5—C6	116.9 (3)	HS6D—CS6'—HS6F	109.5
N7—C6—N5	129.4 (3)	HS6E—CS6'—HS6F	109.5
N7—C6—S6	120.4 (2)	C6'—N7'—C7'A	111.7 (2)
N5—C6—S6	110.2 (2)	N7'—C7'A—N1'	126.2 (3)
C6—S6—CS6	102.7 (2)	N7'—C7'A—C3'A	126.5 (3)
S6—CS6—HS6A	109.5 (2)	N1'—C7'A—C3'A	107.3 (2)
S6—CS6—HS6B	109.47 (13)	N2—C8—C9	111.8 (2)
HS6A—CS6—HS6B	109.5	N2—C8—H8A	109.2 (2)
S6—CS6—HS6C	109.47 (14)	C9—C8—H8A	109.2 (2)
HS6A—CS6—HS6C	109.5	N2—C8—H8B	109.2 (2)
HS6B—CS6—HS6C	109.5	C9—C8—H8B	109.2 (2)
C6—N7—C7A	112.7 (3)	H8A—C8—H8B	107.9
N1—C7A—N7	124.4 (3)	C10—C9—C8	114.9 (3)
N1—C7A—C3A	111.8 (2)	C10—C9—H9A	108.6 (2)
N7—C7A—C3A	123.8 (3)	C8—C9—H9A	108.6 (2)
C7'A—N1'—N2'	111.0 (2)	C10—C9—H9B	108.6 (2)
C7'A—N1'—C10	128.1 (2)	C8—C9—H9B	108.6 (2)
N2'—N1'—C10	120.4 (2)	H9A—C9—H9B	107.5
C3'—N2'—N1'	105.7 (2)	N1'—C10—C9	112.2 (3)
N2'—C3'—C3'A	111.6 (3)	N1'—C10—H10A	109.2 (2)
N2'—C3'—H3'	124.2 (2)	C9—C10—H10A	109.2 (2)
C3'A—C3'—H3'	124.2 (2)	N1'—C10—H10B	109.2 (2)
C4'—C3'A—C7'A	115.6 (3)	C9—C10—H10B	109.2 (2)
C4'—C3'A—C3'	140.1 (3)	H10A—C10—H10B	107.9
C7A—N1—N2—C3	−0.7 (3)	N2'—C3'—C3'A—C7'A	−0.1 (4)
C7A—N1—N2—C8	−179.1 (2)	C7'A—C3'A—C4'—N5'	0.2 (4)
N1—N2—C3—C3A	0.4 (3)	C3'—C3'A—C4'—N5'	178.6 (4)
C8—N2—C3—C3A	178.6 (3)	C7'A—C3'A—C4'—S4'	−179.8 (2)
N2—C3—C3A—C7A	0.1 (3)	C3'—C3'A—C4'—S4'	−1.3 (6)
N2—C3—C3A—C4	−179.3 (3)	N5'—C4'—S4'—CS4'	−5.0 (3)
C3—C3A—C4—N5	179.6 (3)	C3'A—C4'—S4'—CS4'	174.9 (3)
C7A—C3A—C4—N5	0.3 (4)	C3'A—C4'—N5'—C6'	1.0 (4)
C3—C3A—C4—S4	−0.8 (5)	S4'—C4'—N5'—C6'	−179.0 (2)
C7A—C3A—C4—S4	179.9 (2)	C4'—N5'—C6'—N7'	−1.8 (4)
N5—C4—S4—CS4	−8.3 (3)	C4'—N5'—C6'—S6'	178.1 (2)
C3A—C4—S4—CS4	172.1 (3)	N7'—C6'—S6'—CS6'	−175.6 (2)
C3A—C4—N5—C6	0.1 (4)	N5'—C6'—S6'—CS6'	4.4 (3)
S4—C4—N5—C6	−179.4 (2)	N5'—C6'—N7'—C7'A	1.0 (4)
C4—N5—C6—N7	−0.8 (5)	S6'—C6'—N7'—C7'A	−178.9 (2)
C4—N5—C6—S6	179.8 (2)	C6'—N7'—C7'A—N1'	179.8 (3)
N7—C6—S6—CS6	6.5 (3)	C6'—N7'—C7'A—C3'A	0.5 (4)
N5—C6—S6—CS6	−174.0 (2)	N2'—N1'—C7'A—N7'	179.7 (3)
N5—C6—N7—C7A	0.9 (5)	C10—N1'—C7'A—N7'	7.9 (5)
S6—C6—N7—C7A	−179.8 (2)	N2'—N1'—C7'A—C3'A	−0.8 (3)
N2—N1—C7A—N7	179.9 (3)	C10—N1'—C7'A—C3'A	−172.7 (3)
N2—N1—C7A—C3A	0.7 (3)	C4'—C3'A—C7'A—N7'	−1.0 (5)
C6—N7—C7A—N1	−179.5 (3)	C3'—C3'A—C7'A—N7'	−180.0 (3)
C6—N7—C7A—C3A	−0.3 (4)	C4'—C3'A—C7'A—N1'	179.5 (3)
C3—C3A—C7A—N1	−0.5 (3)	C3'—C3'A—C7'A—N1'	0.5 (3)
C4—C3A—C7A—N1	179.0 (3)	C3—N2—C8—C9	120.9 (3)
C3—C3A—C7A—N7	−179.7 (3)	N1—N2—C8—C9	−60.9 (4)
C4—C3A—C7A—N7	−0.2 (4)	N2—C8—C9—C10	−74.3 (3)
C7'A—N1'—N2'—C3'	0.7 (4)	C7'A—N1'—C10—C9	100.5 (4)
C10—N1'—N2'—C3'	173.3 (3)	N2'—N1'—C10—C9	−70.6 (4)
N1'—N2'—C3'—C3'A	−0.4 (4)	C8—C9—C10—N1'	−69.9 (3)
N2'—C3'—C3'A—C4'	−178.7 (4)

(5) 1-[4-(4-methoxy-6-methylthio-1H-pyrazolo[3,4-d]pyrimidin-1-yl)butyl]- 5-methyl-6-methylthio-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-4-one

Crystal data

C18H22N8O2S2	Dx = 1.423 Mg m^−3
Mr = 446.56	Melting point: 150 K
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 31.736 (7) Å	Cell parameters from 39 reflections
b = 8.308 (2) Å	θ = 4.9–12.8°
c = 17.467 (4) Å	µ = 0.29 mm^−1
β = 115.12 (2)°	T = 293 K
V = 4169.8 (17) Å^3	Trapezoidal, colourless
Z = 8	0.8 × 0.6 × 0.5 mm
F(000) = 1872

Data collection

Siemens P4 diffractometer	3189 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 25.0°, θmin = 2.4°
ω–scan	h = 0→37
Absorption correction: ψ scan (local program; Karcher, 1981)	k = 0→9
Tmin = 0.772, Tmax = 0.835	l = −20→18
3616 measured reflections	3 standard reflections every 97 reflections
3616 independent reflections	intensity decay: nil

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.121	w = 1/[σ^2(Fo^2) + (0.0685P)^2 + 1.3387P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3616 reflections	Δρmax = 0.28 e Å^−3
276 parameters	Δρmin = −0.22 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0068 (5)

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	0.08564 (6)	0.62969 (18)	−0.28542 (10)	0.0591 (4)
N2	0.09756 (6)	0.7441 (2)	−0.32902 (11)	0.0705 (4)
C3	0.09214 (8)	0.8831 (3)	−0.29923 (14)	0.0688 (5)
H3	0.0979	0.9821	−0.3177	0.083*
C3A	0.07636 (6)	0.8636 (2)	−0.23533 (12)	0.0568 (4)
C4	0.06206 (6)	0.9544 (2)	−0.18356 (12)	0.0549 (4)
O4	0.06165 (5)	1.11449 (15)	−0.19000 (10)	0.0693 (4)
CO4	0.04383 (8)	1.2044 (3)	−0.13974 (15)	0.0752 (6)
HO4A	0.0432	1.3168	−0.1528	0.113*
HO4B	0.0635	1.1877	−0.0809	0.113*
HO4C	0.0129	1.1686	−0.1520	0.113*
N5	0.04876 (5)	0.88416 (17)	−0.12953 (10)	0.0551 (4)
C6	0.04910 (6)	0.7220 (2)	−0.12731 (11)	0.0542 (4)
S6	0.03384 (2)	0.62550 (6)	−0.05308 (4)	0.0699 (2)
CS6	0.01876 (9)	0.7890 (3)	−0.00360 (16)	0.0864 (7)
HS6A	0.0093	0.7481	0.0381	0.130*
HS6B	−0.0064	0.8488	−0.0454	0.130*
HS6C	0.0452	0.8582	0.0232	0.130*
N7	0.05989 (5)	0.62061 (18)	−0.17441 (10)	0.0574 (4)
C7A	0.07327 (6)	0.6979 (2)	−0.22805 (11)	0.0540 (4)
N1'	0.21661 (5)	0.19233 (19)	−0.16005 (9)	0.0570 (4)
N2'	0.22763 (6)	0.0909 (2)	−0.21125 (10)	0.0673 (4)
C3'	0.22196 (7)	−0.0549 (3)	−0.18828 (12)	0.0678 (5)
H3'	0.2271	−0.1484	−0.2124	0.081*
C3'A	0.20724 (6)	−0.0533 (2)	−0.12306 (11)	0.0581 (4)
C4'	0.19595 (7)	−0.1701 (2)	−0.07508 (12)	0.0619 (5)
O4'	0.19753 (6)	−0.31573 (18)	−0.07920 (11)	0.0862 (5)
N5'	0.18098 (5)	−0.09753 (18)	−0.01662 (9)	0.0574 (4)
C5'	0.17019 (9)	−0.2054 (3)	0.03898 (15)	0.0774 (6)
H5'1	0.1785	−0.3136	0.0318	0.116*
H5'2	0.1375	−0.2002	0.0248	0.116*
H5'3	0.1875	−0.1729	0.0967	0.116*
C6'	0.17761 (6)	0.0666 (2)	−0.01024 (10)	0.0511 (4)
S6'	0.154665 (17)	0.13194 (6)	0.06014 (3)	0.06088 (19)
CS6'	0.15532 (8)	0.3456 (3)	0.04607 (14)	0.0684 (5)
HS6D	0.1412	0.3981	0.0784	0.103*
HS6E	0.1382	0.3714	−0.0127	0.103*
HS6F	0.1869	0.3818	0.0650	0.103*
N7'	0.18896 (5)	0.17353 (18)	−0.05219 (9)	0.0532 (3)
C7'A	0.20397 (6)	0.1076 (2)	−0.10772 (10)	0.0519 (4)
C8	0.08687 (7)	0.4594 (2)	−0.30225 (13)	0.0657 (5)
H8A	0.0862	0.4455	−0.3579	0.079*
H8B	0.0594	0.4080	−0.3023	0.079*
C9	0.12961 (7)	0.3788 (2)	−0.23766 (12)	0.0611 (5)
H9A	0.1258	0.2631	−0.2446	0.073*
H9B	0.1323	0.4052	−0.1817	0.073*
C10	0.17456 (6)	0.4267 (2)	−0.24342 (11)	0.0597 (4)
H10A	0.1744	0.3835	−0.2951	0.072*
H10B	0.1761	0.5431	−0.2459	0.072*
C11	0.21670 (6)	0.3659 (2)	−0.16919 (12)	0.0587 (4)
H11A	0.2444	0.3975	−0.1758	0.070*
H11B	0.2181	0.4160	−0.1180	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0683 (9)	0.0549 (9)	0.0614 (9)	0.0026 (7)	0.0346 (7)	−0.0009 (7)
N2	0.0866 (11)	0.0689 (11)	0.0694 (10)	0.0038 (8)	0.0460 (9)	0.0066 (8)
C3	0.0837 (13)	0.0626 (12)	0.0735 (12)	0.0059 (9)	0.0464 (11)	0.0100 (9)
C3A	0.0581 (9)	0.0518 (10)	0.0639 (10)	0.0047 (7)	0.0292 (8)	0.0068 (8)
C4	0.0541 (9)	0.0475 (10)	0.0645 (10)	0.0018 (7)	0.0264 (8)	0.0032 (7)
O4	0.0872 (9)	0.0456 (7)	0.0887 (10)	0.0050 (6)	0.0504 (8)	0.0072 (6)
CO4	0.0965 (15)	0.0497 (11)	0.0857 (14)	0.0093 (10)	0.0446 (12)	−0.0030 (10)
N5	0.0574 (8)	0.0496 (8)	0.0620 (9)	0.0017 (6)	0.0289 (7)	0.0017 (6)
C6	0.0540 (9)	0.0504 (10)	0.0604 (10)	−0.0001 (7)	0.0265 (8)	0.0011 (7)
S6	0.0917 (4)	0.0570 (3)	0.0802 (4)	0.0014 (2)	0.0549 (3)	0.0063 (2)
CS6	0.1172 (18)	0.0799 (15)	0.0858 (14)	0.0203 (13)	0.0658 (14)	0.0088 (12)
N7	0.0645 (9)	0.0490 (8)	0.0650 (9)	−0.0012 (6)	0.0335 (7)	−0.0003 (6)
C7A	0.0532 (9)	0.0521 (10)	0.0590 (9)	0.0022 (7)	0.0260 (7)	0.0010 (7)
N1'	0.0695 (9)	0.0587 (9)	0.0528 (8)	0.0089 (7)	0.0356 (7)	−0.0018 (7)
N2'	0.0825 (10)	0.0721 (11)	0.0604 (9)	0.0118 (8)	0.0429 (8)	−0.0074 (8)
C3'	0.0805 (12)	0.0679 (13)	0.0613 (10)	0.0129 (10)	0.0362 (9)	−0.0135 (9)
C3'A	0.0671 (10)	0.0550 (10)	0.0530 (9)	0.0097 (8)	0.0262 (8)	−0.0061 (8)
C4'	0.0729 (11)	0.0510 (11)	0.0586 (10)	0.0082 (8)	0.0247 (9)	−0.0055 (8)
O4'	0.1227 (12)	0.0478 (8)	0.0925 (11)	0.0073 (8)	0.0500 (10)	−0.0075 (7)
N5'	0.0693 (9)	0.0488 (8)	0.0548 (8)	0.0050 (6)	0.0271 (7)	0.0030 (6)
C5'	0.1006 (15)	0.0556 (12)	0.0846 (14)	0.0015 (10)	0.0477 (12)	0.0127 (10)
C6'	0.0571 (9)	0.0493 (9)	0.0467 (8)	0.0044 (7)	0.0217 (7)	−0.0008 (7)
S6'	0.0752 (3)	0.0635 (3)	0.0556 (3)	0.0044 (2)	0.0389 (2)	0.00198 (19)
CS6'	0.0860 (13)	0.0624 (11)	0.0710 (12)	0.0039 (9)	0.0471 (10)	−0.0100 (9)
N7'	0.0690 (8)	0.0486 (8)	0.0491 (7)	0.0064 (6)	0.0318 (6)	−0.0008 (6)
C7'A	0.0585 (9)	0.0534 (10)	0.0465 (8)	0.0089 (7)	0.0249 (7)	−0.0019 (7)
C8	0.0713 (11)	0.0605 (11)	0.0701 (11)	−0.0038 (9)	0.0347 (9)	−0.0120 (9)
C9	0.0747 (11)	0.0497 (10)	0.0686 (11)	0.0003 (8)	0.0399 (9)	0.0018 (8)
C10	0.0731 (11)	0.0551 (10)	0.0593 (10)	0.0006 (8)	0.0360 (9)	0.0023 (8)
C11	0.0676 (10)	0.0594 (11)	0.0589 (10)	−0.0026 (8)	0.0364 (9)	−0.0026 (8)

Geometric parameters (Å, º)

N1—C7A	1.347 (2)	N1'—C11	1.451 (2)
N1—N2	1.368 (2)	N2'—C3'	1.313 (3)
N1—C8	1.449 (2)	C3'—C3'A	1.403 (3)
N2—C3	1.307 (3)	C3'A—C7'A	1.375 (3)
C3—C3A	1.413 (3)	C3'A—C4'	1.424 (3)
C3A—C7A	1.390 (3)	C4'—O4'	1.214 (3)
C3A—C4	1.393 (3)	C4'—N5'	1.430 (2)
C4—N5	1.322 (2)	N5'—C6'	1.376 (2)
C4—O4	1.334 (2)	N5'—C5'	1.465 (3)
O4—CO4	1.439 (2)	C6'—N7'	1.296 (2)
N5—C6	1.348 (2)	C6'—S6'	1.7597 (17)
C6—N7	1.320 (2)	S6'—CS6'	1.794 (2)
C6—S6	1.7582 (18)	N7'—C7'A	1.364 (2)
S6—CS6	1.781 (2)	C8—C9	1.504 (3)
N7—C7A	1.345 (2)	C9—C10	1.525 (2)
N1'—C7'A	1.343 (2)	C10—C11	1.501 (3)
N1'—N2'	1.378 (2)
C7A—N1—N2	111.02 (14)	C3'—N2'—N1'	105.11 (15)
C7A—N1—C8	127.11 (16)	N2'—C3'—C3'A	112.04 (17)
N2—N1—C8	121.87 (16)	C7'A—C3'A—C3'	104.26 (18)
C3—N2—N1	106.13 (16)	C7'A—C3'A—C4'	119.27 (16)
N2—C3—C3A	111.33 (18)	C3'—C3'A—C4'	136.47 (18)
C7A—C3A—C4	114.96 (16)	O4'—C4'—C3'A	128.11 (19)
C7A—C3A—C3	104.37 (17)	O4'—C4'—N5'	119.82 (19)
C4—C3A—C3	140.60 (18)	C3'A—C4'—N5'	112.07 (16)
N5—C4—O4	120.37 (16)	C6'—N5'—C4'	122.45 (16)
N5—C4—C3A	120.99 (16)	C6'—N5'—C5'	120.29 (16)
O4—C4—C3A	118.63 (16)	C4'—N5'—C5'	117.24 (16)
C4—O4—CO4	117.27 (15)	N7'—C6'—N5'	125.72 (15)
C4—N5—C6	117.44 (16)	N7'—C6'—S6'	118.69 (13)
N7—C6—N5	128.38 (16)	N5'—C6'—S6'	115.58 (13)
N7—C6—S6	113.22 (13)	C6'—S6'—CS6'	100.22 (9)
N5—C6—S6	118.40 (13)	C6'—N7'—C7'A	113.03 (15)
C6—S6—CS6	103.00 (10)	N1'—C7'A—N7'	124.65 (16)
C6—N7—C7A	111.83 (15)	N1'—C7'A—C3'A	107.94 (15)
N7—C7A—N1	126.56 (16)	N7'—C7'A—C3'A	127.37 (17)
N7—C7A—C3A	126.31 (17)	N1—C8—C9	112.09 (16)
N1—C7A—C3A	107.13 (15)	C8—C9—C10	113.92 (16)
C7'A—N1'—N2'	110.64 (15)	C11—C10—C9	111.76 (15)
C7'A—N1'—C11	127.69 (14)	N1'—C11—C10	112.76 (15)
N2'—N1'—C11	121.56 (15)
C7A—N1—N2—C3	−0.6 (2)	C7'A—C3'A—C4'—O4'	−178.8 (2)
C8—N1—N2—C3	179.28 (18)	C3'—C3'A—C4'—O4'	1.7 (4)
N1—N2—C3—C3A	−0.2 (2)	C7'A—C3'A—C4'—N5'	1.6 (2)
N2—C3—C3A—C7A	0.8 (2)	C3'—C3'A—C4'—N5'	−177.9 (2)
N2—C3—C3A—C4	−175.7 (2)	O4'—C4'—N5'—C6'	−178.70 (18)
C7A—C3A—C4—N5	2.9 (2)	C3'A—C4'—N5'—C6'	1.0 (2)
C3—C3A—C4—N5	179.2 (2)	O4'—C4'—N5'—C5'	2.8 (3)
C7A—C3A—C4—O4	−176.53 (16)	C3'A—C4'—N5'—C5'	−177.55 (16)
C3—C3A—C4—O4	−0.3 (4)	C4'—N5'—C6'—N7'	−3.0 (3)
N5—C4—O4—CO4	−3.4 (3)	C5'—N5'—C6'—N7'	175.49 (17)
C3A—C4—O4—CO4	176.02 (17)	C4'—N5'—C6'—S6'	175.72 (13)
O4—C4—N5—C6	178.70 (15)	C5'—N5'—C6'—S6'	−5.8 (2)
C3A—C4—N5—C6	−0.7 (2)	N7'—C6'—S6'—CS6'	0.22 (16)
C4—N5—C6—N7	−2.1 (3)	N5'—C6'—S6'—CS6'	−178.56 (14)
C4—N5—C6—S6	177.46 (12)	N5'—C6'—N7'—C7'A	1.9 (2)
N7—C6—S6—CS6	−177.38 (14)	S6'—C6'—N7'—C7'A	−176.75 (11)
N5—C6—S6—CS6	2.95 (17)	N2'—N1'—C7'A—N7'	−176.75 (15)
N5—C6—N7—C7A	2.2 (3)	C11—N1'—C7'A—N7'	−0.5 (3)
S6—C6—N7—C7A	−177.39 (12)	N2'—N1'—C7'A—C3'A	0.9 (2)
C6—N7—C7A—N1	−178.67 (16)	C11—N1'—C7'A—C3'A	177.14 (16)
C6—N7—C7A—C3A	0.5 (3)	C6'—N7'—C7'A—N1'	178.24 (15)
N2—N1—C7A—N7	−179.61 (16)	C6'—N7'—C7'A—C3'A	1.0 (3)
C8—N1—C7A—N7	0.5 (3)	C3'—C3'A—C7'A—N1'	−0.7 (2)
N2—N1—C7A—C3A	1.1 (2)	C4'—C3'A—C7'A—N1'	179.58 (15)
C8—N1—C7A—C3A	−178.75 (17)	C3'—C3'A—C7'A—N7'	176.84 (17)
C4—C3A—C7A—N7	−2.9 (3)	C4'—C3'A—C7'A—N7'	−2.8 (3)
C3—C3A—C7A—N7	179.58 (17)	C7A—N1—C8—C9	−78.9 (2)
C4—C3A—C7A—N1	176.40 (14)	N2—N1—C8—C9	101.3 (2)
C3—C3A—C7A—N1	−1.2 (2)	N1—C8—C9—C10	−70.2 (2)
C7'A—N1'—N2'—C3'	−0.7 (2)	C8—C9—C10—C11	170.26 (16)
C11—N1'—N2'—C3'	−177.18 (16)	C7'A—N1'—C11—C10	−99.0 (2)
N1'—N2'—C3'—C3'A	0.2 (2)	N2'—N1'—C11—C10	76.9 (2)
N2'—C3'—C3'A—C7'A	0.3 (2)	C9—C10—C11—N1'	57.8 (2)
N2'—C3'—C3'A—C4'	179.9 (2)