Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0021889804017832/do5007sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0021889804017832/do5007298gHNIWsup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0021889804017832/do5007250gHNIWsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0021889804017832/do5007200gHNIWsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0021889804017832/do5007150gHNIWsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0021889804017832/do5007100gHNIWsup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0021889804017832/do5007298eHNIWsup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0021889804017832/do5007250eHNIWsup8.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0021889804017832/do5007200eHNIWsup9.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0021889804017832/do5007150eHNIWsup10.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0021889804017832/do5007100eHNIWsup11.hkl |
CCDC references: 251401; 251402; 251403; 251404; 251405; 251406; 251407; 251408; 251409; 251410
For all compounds, data collection: Siemens SMART; cell refinement: Siemens SAINT; data reduction: Siemens SAINT. Program(s) used to solve structure: SHELXS86 (Sheldrick, 1990) for 298gHNIW, 250gHNIW, 200gHNIW, 150gHNIW, 100gHNIW; SHELXS97 (Sheldrick, 1990) for 298eHNIW, 250eHNIW, 200eHNIW, 150eHNIW, 100eHNIW. Program(s) used to refine structure: SHELXL93 (Sheldrick, 1993) for 298gHNIW, 250gHNIW, 200gHNIW, 150gHNIW, 100gHNIW; SHELXL97 (Sheldrick, 1997) for 298eHNIW, 250eHNIW, 200eHNIW, 150eHNIW, 100eHNIW. For all compounds, molecular graphics: Siemens SHELXTL. Software used to prepare material for publication: Siemens SHELXTL and the Toledo cifomatic for 298gHNIW, 250gHNIW, 200gHNIW, 150gHNIW, 100gHNIW; Siemens SHELXTL for 298eHNIW, 250eHNIW, 200eHNIW, 150eHNIW, 100eHNIW.
C6H6N12O12 | F(000) = 888 |
Mr = 438.23 | Dx = 1.915 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 13.2272 (7) Å | Cell parameters from 5732 reflections |
b = 8.1692 (5) Å | θ = 3.1–20.4° |
c = 14.8920 (8) Å | µ = 0.18 mm−1 |
β = 109.164 (1)° | T = 298 K |
V = 1520.0 (2) Å3 | Block |
Z = 4 | 0.37 × 0.33 × 0.18 mm |
Platform diffractometer | 3746 independent reflections |
Radiation source: Sealed Tube | 2671 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
ω scans | θmax = 28.3°, θmin = 2.5° |
Absorption correction: empirical :Multipole Expansion Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | h = −17→7 |
Tmin = 0.627, Tmax = 0.990 | k = −10→10 |
10300 measured reflections | l = −19→19 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Calculated w = 1/[σ2(Fo2) + (0.0607P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.115 | (Δ/σ)max = −0.001 |
S = 1.02 | Δρmax = 0.27 e Å−3 |
3746 reflections | Δρmin = −0.22 e Å−3 |
296 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0127 (15) |
Primary atom site location: structure-invariant direct methods |
C6H6N12O12 | V = 1520.0 (2) Å3 |
Mr = 438.23 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 13.2272 (7) Å | µ = 0.18 mm−1 |
b = 8.1692 (5) Å | T = 298 K |
c = 14.8920 (8) Å | 0.37 × 0.33 × 0.18 mm |
β = 109.164 (1)° |
Platform diffractometer | 3746 independent reflections |
Absorption correction: empirical :Multipole Expansion Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | 2671 reflections with I > 2σ(I) |
Tmin = 0.627, Tmax = 0.990 | Rint = 0.039 |
10300 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 296 parameters |
wR(F2) = 0.115 | 0 restraints |
S = 1.02 | Δρmax = 0.27 e Å−3 |
3746 reflections | Δρmin = −0.22 e Å−3 |
Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS. No formal measure of the extent of decay is printed out by this program. The final unit cell is obtained from the refinement of the XYZ weighted centroids of reflections above 20 σ(I). |
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 0 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_obs 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. |
x | y | z | Uiso*/Ueq | ||
N1 | 1.01349 (11) | 0.4574 (2) | 0.34558 (8) | 0.0285 (3) | |
C1 | 1.10707 (13) | 0.5134 (2) | 0.32341 (10) | 0.0286 (3) | |
H1 | 1.1698 (15) | 0.455 (2) | 0.3558 (12) | 0.034 (4)* | |
O1 | 1.11604 (13) | 0.2992 (2) | 0.46269 (9) | 0.0597 (4) | |
O2 | 0.95367 (12) | 0.3504 (2) | 0.45602 (8) | 0.0495 (4) | |
C2 | 0.93689 (12) | 0.5926 (2) | 0.32615 (10) | 0.0260 (3) | |
H2 | 0.9006 (15) | 0.5929 (19) | 0.3688 (12) | 0.031 (4)* | |
N2 | 1.03025 (14) | 0.3637 (2) | 0.42837 (9) | 0.0380 (4) | |
N3 | 1.11598 (10) | 0.6861 (2) | 0.34891 (8) | 0.0286 (3) | |
C3 | 1.00665 (12) | 0.7500 (2) | 0.32963 (10) | 0.0261 (3) | |
H3 | 1.0065 (14) | 0.825 (2) | 0.3780 (12) | 0.031 (4)* | |
O3 | 1.18378 (13) | 0.8665 (2) | 0.46544 (10) | 0.0611 (4) | |
C4 | 1.08410 (12) | 0.5012 (2) | 0.21178 (10) | 0.0278 (3) | |
H4 | 1.1372 (15) | 0.437 (2) | 0.2000 (11) | 0.033 (4)* | |
O4 | 1.26246 (12) | 0.6317 (2) | 0.47409 (10) | 0.0634 (4) | |
N4 | 1.19287 (12) | 0.7302 (2) | 0.43760 (10) | 0.0412 (4) | |
N5 | 0.97052 (11) | 0.82907 (14) | 0.23881 (8) | 0.0295 (3) | |
C5 | 0.90143 (13) | 0.5741 (2) | 0.15363 (10) | 0.0257 (3) | |
H5 | 0.8471 (14) | 0.5608 (18) | 0.0980 (11) | 0.023 (4)* | |
O5 | 0.9853 (2) | 1.0716 (2) | 0.30754 (11) | 0.0832 (6) | |
C6 | 0.96894 (13) | 0.7334 (2) | 0.15718 (10) | 0.0265 (3) | |
H6 | 0.9407 (13) | 0.796 (2) | 0.1022 (12) | 0.028 (4)* | |
O6 | 0.93915 (14) | 1.0574 (2) | 0.15360 (9) | 0.0641 (5) | |
N6 | 0.96633 (14) | 0.9988 (2) | 0.23263 (11) | 0.0480 (4) | |
N7 | 0.85936 (10) | 0.5784 (2) | 0.23148 (8) | 0.0283 (3) | |
O7 | 0.75611 (14) | 0.4420 (3) | 0.29756 (11) | 0.0865 (6) | |
O8 | 0.72838 (13) | 0.4108 (2) | 0.14741 (10) | 0.0717 (5) | |
N8 | 0.77517 (13) | 0.4669 (2) | 0.22496 (11) | 0.0496 (4) | |
O9 | 0.87675 (12) | 0.3432 (2) | 0.02050 (8) | 0.0488 (4) | |
N9 | 0.97772 (11) | 0.43594 (14) | 0.16436 (8) | 0.0272 (3) | |
N10 | 0.96690 (13) | 0.3580 (2) | 0.07474 (9) | 0.0365 (3) | |
O10 | 1.04827 (12) | 0.3081 (2) | 0.06365 (9) | 0.0538 (4) | |
N11 | 1.07285 (11) | 0.66059 (15) | 0.16574 (8) | 0.0281 (3) | |
O11 | 1.24831 (11) | 0.6909 (2) | 0.20907 (11) | 0.0597 (4) | |
N12 | 1.16158 (12) | 0.7583 (2) | 0.17901 (10) | 0.0404 (4) | |
O12 | 1.14506 (12) | 0.9007 (2) | 0.15740 (10) | 0.0567 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0341 (7) | 0.0303 (7) | 0.0225 (6) | 0.0030 (5) | 0.0111 (5) | 0.0049 (5) |
C1 | 0.0261 (8) | 0.0355 (8) | 0.0235 (7) | 0.0054 (7) | 0.0073 (6) | 0.0018 (6) |
O1 | 0.0704 (11) | 0.0606 (9) | 0.0406 (7) | 0.0185 (8) | 0.0079 (7) | 0.0218 (6) |
O2 | 0.0736 (10) | 0.0457 (7) | 0.0390 (7) | −0.0129 (6) | 0.0320 (7) | 0.0031 (5) |
C2 | 0.0256 (8) | 0.0313 (8) | 0.0234 (7) | −0.0013 (6) | 0.0111 (6) | −0.0009 (5) |
N2 | 0.0606 (11) | 0.0301 (7) | 0.0228 (6) | −0.0030 (7) | 0.0132 (7) | 0.0011 (5) |
N3 | 0.0231 (7) | 0.0382 (7) | 0.0215 (6) | −0.0040 (5) | 0.0032 (5) | −0.0044 (5) |
C3 | 0.0280 (8) | 0.0266 (7) | 0.0241 (7) | −0.0011 (6) | 0.0089 (6) | −0.0042 (5) |
O3 | 0.0622 (10) | 0.0599 (9) | 0.0489 (8) | −0.0188 (7) | 0.0017 (7) | −0.0224 (6) |
C4 | 0.0280 (8) | 0.0342 (8) | 0.0230 (7) | 0.0037 (7) | 0.0106 (6) | 0.0002 (6) |
O4 | 0.0368 (8) | 0.0915 (11) | 0.0440 (8) | 0.0089 (8) | −0.0108 (6) | −0.0067 (7) |
N4 | 0.0310 (8) | 0.0612 (10) | 0.0270 (7) | −0.0136 (7) | 0.0038 (6) | −0.0069 (6) |
N5 | 0.0376 (8) | 0.0206 (6) | 0.0292 (6) | −0.0001 (5) | 0.0094 (6) | 0.0005 (4) |
C5 | 0.0256 (8) | 0.0272 (7) | 0.0216 (7) | −0.0031 (6) | 0.0041 (6) | 0.0006 (5) |
O5 | 0.155 (2) | 0.0293 (7) | 0.0565 (9) | −0.0053 (9) | 0.0228 (10) | −0.0145 (6) |
C6 | 0.0305 (8) | 0.0251 (7) | 0.0227 (7) | −0.0029 (6) | 0.0072 (6) | 0.0016 (5) |
O6 | 0.1053 (14) | 0.0298 (7) | 0.0538 (8) | 0.0049 (7) | 0.0217 (9) | 0.0143 (6) |
N6 | 0.0676 (11) | 0.0239 (7) | 0.0500 (9) | −0.0011 (7) | 0.0158 (8) | −0.0003 (6) |
N7 | 0.0202 (6) | 0.0370 (7) | 0.0276 (6) | −0.0063 (5) | 0.0079 (5) | −0.0015 (5) |
O7 | 0.0648 (11) | 0.148 (2) | 0.0541 (9) | −0.0623 (11) | 0.0301 (8) | −0.0068 (10) |
O8 | 0.0593 (10) | 0.1030 (13) | 0.0484 (8) | −0.0524 (9) | 0.0118 (7) | −0.0152 (8) |
N8 | 0.0351 (9) | 0.0717 (11) | 0.0422 (9) | −0.0248 (8) | 0.0129 (7) | −0.0040 (7) |
O9 | 0.0596 (9) | 0.0513 (8) | 0.0287 (6) | −0.0102 (6) | 0.0052 (6) | −0.0113 (5) |
N9 | 0.0349 (7) | 0.0277 (6) | 0.0190 (6) | −0.0015 (5) | 0.0090 (5) | −0.0031 (4) |
N10 | 0.0565 (10) | 0.0305 (7) | 0.0258 (7) | −0.0054 (6) | 0.0182 (7) | −0.0028 (5) |
O10 | 0.0632 (10) | 0.0624 (9) | 0.0457 (7) | 0.0010 (7) | 0.0315 (7) | −0.0181 (6) |
N11 | 0.0270 (7) | 0.0338 (7) | 0.0250 (6) | −0.0051 (5) | 0.0105 (5) | 0.0010 (5) |
O11 | 0.0289 (8) | 0.0847 (11) | 0.0660 (9) | −0.0088 (7) | 0.0161 (7) | 0.0029 (8) |
N12 | 0.0366 (9) | 0.0537 (10) | 0.0343 (8) | −0.0162 (7) | 0.0160 (7) | −0.0040 (6) |
O12 | 0.0601 (10) | 0.0457 (8) | 0.0701 (9) | −0.0222 (7) | 0.0293 (8) | −0.0008 (6) |
N1—N2 | 1.405 (2) | N5—C6 | 1.440 (2) |
N1—C1 | 1.456 (2) | C5—N7 | 1.442 (2) |
N1—C2 | 1.462 (2) | C5—N9 | 1.487 (2) |
C1—N3 | 1.456 (2) | C5—C6 | 1.569 (2) |
C1—C4 | 1.592 (2) | O5—N6 | 1.215 (2) |
O1—N2 | 1.202 (2) | C6—N11 | 1.464 (2) |
O2—N2 | 1.217 (2) | O6—N6 | 1.211 (2) |
C2—N7 | 1.450 (2) | N7—N8 | 1.417 (2) |
C2—C3 | 1.573 (2) | O7—N8 | 1.205 (2) |
N3—N4 | 1.424 (2) | O8—N8 | 1.207 (2) |
N3—C3 | 1.474 (2) | O9—N10 | 1.207 (2) |
C3—N5 | 1.432 (2) | N9—N10 | 1.443 (2) |
O3—N4 | 1.208 (2) | N10—O10 | 1.212 (2) |
C4—N9 | 1.453 (2) | N11—N12 | 1.379 (2) |
C4—N11 | 1.457 (2) | O11—N12 | 1.218 (2) |
O4—N4 | 1.209 (2) | N12—O12 | 1.208 (2) |
N5—N6 | 1.390 (2) | ||
N2—N1—C1 | 117.97 (13) | N7—C5—N9 | 111.08 (11) |
N2—N1—C2 | 118.98 (12) | N7—C5—C6 | 108.55 (11) |
C1—N1—C2 | 107.65 (11) | N9—C5—C6 | 105.50 (12) |
N1—C1—N3 | 104.32 (12) | N5—C6—N11 | 113.20 (12) |
N1—C1—C4 | 109.40 (12) | N5—C6—C5 | 109.22 (12) |
N3—C1—C4 | 107.72 (11) | N11—C6—C5 | 100.00 (11) |
N7—C2—N1 | 110.78 (11) | O6—N6—O5 | 127.3 (2) |
N7—C2—C3 | 108.50 (11) | O6—N6—N5 | 116.82 (14) |
N1—C2—C3 | 104.49 (12) | O5—N6—N5 | 115.82 (14) |
O1—N2—O2 | 126.23 (14) | N8—N7—C5 | 115.55 (12) |
O1—N2—N1 | 117.82 (15) | N8—N7—C2 | 114.02 (12) |
O2—N2—N1 | 115.86 (15) | C5—N7—C2 | 116.57 (12) |
N4—N3—C1 | 117.34 (12) | O7—N8—O8 | 127.0 (2) |
N4—N3—C3 | 116.58 (12) | O7—N8—N7 | 115.99 (14) |
C1—N3—C3 | 107.59 (11) | O8—N8—N7 | 117.00 (14) |
N5—C3—N3 | 110.21 (12) | N10—N9—C4 | 113.43 (12) |
N5—C3—C2 | 109.10 (12) | N10—N9—C5 | 112.20 (11) |
N3—C3—C2 | 104.13 (11) | C4—N9—C5 | 106.78 (11) |
N9—C4—N11 | 99.57 (11) | O9—N10—O10 | 126.99 (14) |
N9—C4—C1 | 110.67 (12) | O9—N10—N9 | 116.08 (14) |
N11—C4—C1 | 112.99 (12) | O10—N10—N9 | 116.85 (14) |
O3—N4—O4 | 127.3 (2) | N12—N11—C4 | 119.97 (13) |
O3—N4—N3 | 115.50 (15) | N12—N11—C6 | 120.52 (12) |
O4—N4—N3 | 117.07 (15) | C4—N11—C6 | 110.61 (11) |
N6—N5—C3 | 120.42 (12) | O12—N12—O11 | 126.9 (2) |
N6—N5—C6 | 119.79 (12) | O12—N12—N11 | 116.65 (15) |
C3—N5—C6 | 117.42 (11) | O11—N12—N11 | 116.46 (15) |
C6H6N12O12 | F(000) = 888 |
Mr = 438.23 | Dx = 1.929 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 13.1670 (3) Å | Cell parameters from 6062 reflections |
b = 8.1676 (1) Å | θ = 3.1–22.2° |
c = 14.8436 (1) Å | µ = 0.19 mm−1 |
β = 109.001 (1)° | T = 250 K |
V = 1509.34 (4) Å3 | Block |
Z = 4 | 0.37 × 0.33 × 0.18 mm |
Platform diffractometer | 3714 independent reflections |
Radiation source: Sealed Tube | 2772 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
ω scans | θmax = 28.3°, θmin = 2.5° |
Absorption correction: empirical :Multipole Expansion Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | h = −17→7 |
Tmin = 0.743, Tmax = 0.990 | k = −10→10 |
10203 measured reflections | l = −19→19 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Calculated w = 1/[σ2(Fo2) + (0.0556P)2 + 0.1184P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.109 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.31 e Å−3 |
3714 reflections | Δρmin = −0.22 e Å−3 |
296 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0096 (13) |
Primary atom site location: structure-invariant direct methods |
C6H6N12O12 | V = 1509.34 (4) Å3 |
Mr = 438.23 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 13.1670 (3) Å | µ = 0.19 mm−1 |
b = 8.1676 (1) Å | T = 250 K |
c = 14.8436 (1) Å | 0.37 × 0.33 × 0.18 mm |
β = 109.001 (1)° |
Platform diffractometer | 3714 independent reflections |
Absorption correction: empirical :Multipole Expansion Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | 2772 reflections with I > 2σ(I) |
Tmin = 0.743, Tmax = 0.990 | Rint = 0.037 |
10203 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 296 parameters |
wR(F2) = 0.109 | 0 restraints |
S = 1.03 | Δρmax = 0.31 e Å−3 |
3714 reflections | Δρmin = −0.22 e Å−3 |
Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS. No formal measure of the extent of decay is printed out by this program. The final unit cell is obtained from the refinement of the XYZ weighted centroids of reflections above 20 σ(I). |
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 0 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_obs 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. |
x | y | z | Uiso*/Ueq | ||
C1 | 1.10712 (12) | 0.5120 (2) | 0.32352 (10) | 0.0224 (3) | |
C2 | 0.93654 (12) | 0.5942 (2) | 0.32656 (10) | 0.0208 (3) | |
C3 | 1.00748 (12) | 0.7505 (2) | 0.32999 (10) | 0.0211 (3) | |
C4 | 1.08408 (12) | 0.4996 (2) | 0.21162 (10) | 0.0226 (3) | |
C5 | 0.90099 (12) | 0.5748 (2) | 0.15356 (10) | 0.0205 (3) | |
C6 | 0.96961 (12) | 0.7335 (2) | 0.15709 (10) | 0.0214 (3) | |
N1 | 1.01287 (10) | 0.45789 (14) | 0.34580 (8) | 0.0231 (3) | |
N2 | 1.02870 (13) | 0.3641 (2) | 0.42844 (9) | 0.0301 (3) | |
N3 | 1.11678 (10) | 0.68546 (15) | 0.34901 (8) | 0.0228 (3) | |
N4 | 1.19387 (11) | 0.7288 (2) | 0.43789 (9) | 0.0329 (3) | |
N5 | 0.97169 (11) | 0.82949 (14) | 0.23886 (8) | 0.0233 (3) | |
N6 | 0.96819 (13) | 0.9995 (2) | 0.23260 (10) | 0.0383 (4) | |
N7 | 0.85886 (10) | 0.58036 (15) | 0.23191 (8) | 0.0227 (3) | |
N8 | 0.77392 (12) | 0.4701 (2) | 0.22545 (11) | 0.0406 (4) | |
N9 | 0.97693 (11) | 0.43579 (14) | 0.16438 (8) | 0.0218 (3) | |
N10 | 0.96593 (12) | 0.3580 (2) | 0.07439 (9) | 0.0287 (3) | |
N11 | 1.07362 (10) | 0.65945 (15) | 0.16537 (8) | 0.0228 (3) | |
N12 | 1.16289 (11) | 0.7559 (2) | 0.17898 (9) | 0.0325 (3) | |
O1 | 1.11490 (12) | 0.2990 (2) | 0.46309 (9) | 0.0473 (4) | |
O2 | 0.95137 (11) | 0.35137 (15) | 0.45605 (8) | 0.0398 (3) | |
O3 | 1.18566 (12) | 0.8657 (2) | 0.46546 (9) | 0.0481 (4) | |
O4 | 1.26315 (11) | 0.6294 (2) | 0.47468 (9) | 0.0510 (4) | |
O5 | 0.9872 (2) | 1.0726 (2) | 0.30750 (10) | 0.0685 (6) | |
O6 | 0.94194 (14) | 1.05779 (14) | 0.15356 (9) | 0.0515 (4) | |
O7 | 0.75388 (13) | 0.4468 (2) | 0.29855 (10) | 0.0707 (5) | |
O8 | 0.72656 (13) | 0.4137 (2) | 0.14787 (10) | 0.0584 (5) | |
O9 | 0.87529 (11) | 0.34288 (15) | 0.02060 (8) | 0.0387 (3) | |
O10 | 1.04726 (11) | 0.3087 (2) | 0.06240 (9) | 0.0429 (3) | |
O11 | 1.24989 (10) | 0.6878 (2) | 0.20908 (10) | 0.0474 (4) | |
O12 | 1.14703 (12) | 0.8992 (2) | 0.15747 (10) | 0.0455 (3) | |
H1 | 1.1707 (15) | 0.452 (2) | 0.3554 (12) | 0.027 (4)* | |
H2 | 0.9007 (14) | 0.5964 (19) | 0.3689 (12) | 0.022 (4)* | |
H3 | 1.0077 (14) | 0.8239 (19) | 0.3789 (12) | 0.022 (4)* | |
H4 | 1.1382 (15) | 0.433 (2) | 0.1986 (12) | 0.027 (4)* | |
H5 | 0.8463 (14) | 0.5621 (18) | 0.0976 (11) | 0.018 (4)* | |
H6 | 0.9414 (13) | 0.7959 (19) | 0.1018 (12) | 0.021 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0207 (7) | 0.0270 (7) | 0.0196 (7) | 0.0043 (6) | 0.0067 (6) | 0.0012 (5) |
C2 | 0.0196 (7) | 0.0247 (7) | 0.0200 (7) | −0.0016 (6) | 0.0090 (6) | −0.0009 (5) |
C3 | 0.0221 (7) | 0.0217 (7) | 0.0199 (7) | −0.0010 (6) | 0.0074 (6) | −0.0023 (5) |
C4 | 0.0238 (8) | 0.0255 (7) | 0.0193 (7) | 0.0019 (6) | 0.0082 (6) | −0.0003 (5) |
C5 | 0.0191 (7) | 0.0220 (7) | 0.0185 (7) | −0.0018 (6) | 0.0034 (6) | −0.0002 (5) |
C6 | 0.0239 (8) | 0.0206 (7) | 0.0187 (7) | −0.0015 (6) | 0.0057 (6) | 0.0014 (5) |
N1 | 0.0291 (7) | 0.0232 (6) | 0.0184 (6) | 0.0017 (5) | 0.0097 (5) | 0.0044 (4) |
N2 | 0.0468 (9) | 0.0240 (6) | 0.0192 (6) | −0.0022 (6) | 0.0103 (6) | 0.0008 (5) |
N3 | 0.0190 (6) | 0.0304 (7) | 0.0167 (6) | −0.0036 (5) | 0.0027 (5) | −0.0033 (4) |
N4 | 0.0244 (7) | 0.0479 (9) | 0.0236 (7) | −0.0101 (6) | 0.0038 (6) | −0.0054 (6) |
N5 | 0.0297 (7) | 0.0148 (6) | 0.0244 (6) | 0.0002 (5) | 0.0076 (5) | 0.0003 (4) |
N6 | 0.0540 (10) | 0.0186 (6) | 0.0407 (8) | −0.0001 (6) | 0.0131 (7) | −0.0004 (5) |
N7 | 0.0159 (6) | 0.0282 (6) | 0.0240 (6) | −0.0040 (5) | 0.0067 (5) | −0.0014 (5) |
N8 | 0.0268 (8) | 0.0602 (10) | 0.0354 (8) | −0.0201 (7) | 0.0109 (6) | −0.0026 (7) |
N9 | 0.0280 (7) | 0.0211 (6) | 0.0166 (6) | −0.0012 (5) | 0.0078 (5) | −0.0027 (4) |
N10 | 0.0447 (9) | 0.0230 (6) | 0.0216 (6) | −0.0036 (6) | 0.0153 (6) | −0.0026 (5) |
N11 | 0.0214 (6) | 0.0267 (6) | 0.0215 (6) | −0.0045 (5) | 0.0088 (5) | 0.0010 (4) |
N12 | 0.0288 (8) | 0.0439 (9) | 0.0279 (7) | −0.0124 (6) | 0.0134 (6) | −0.0037 (6) |
O1 | 0.0564 (9) | 0.0472 (8) | 0.0330 (7) | 0.0149 (7) | 0.0070 (6) | 0.0165 (5) |
O2 | 0.0580 (9) | 0.0362 (7) | 0.0330 (6) | −0.0117 (6) | 0.0256 (6) | 0.0024 (5) |
O3 | 0.0492 (9) | 0.0452 (8) | 0.0405 (7) | −0.0148 (6) | 0.0017 (6) | −0.0175 (6) |
O4 | 0.0311 (7) | 0.0718 (10) | 0.0366 (7) | 0.0080 (7) | −0.0074 (6) | −0.0051 (6) |
O5 | 0.129 (2) | 0.0233 (7) | 0.0452 (8) | −0.0028 (8) | 0.0181 (9) | −0.0117 (5) |
O6 | 0.0844 (12) | 0.0237 (6) | 0.0441 (7) | 0.0046 (6) | 0.0177 (8) | 0.0119 (5) |
O7 | 0.0521 (10) | 0.1225 (15) | 0.0440 (8) | −0.0516 (10) | 0.0245 (7) | −0.0065 (8) |
O8 | 0.0481 (9) | 0.0840 (11) | 0.0400 (8) | −0.0436 (8) | 0.0103 (7) | −0.0127 (7) |
O9 | 0.0467 (8) | 0.0402 (7) | 0.0242 (6) | −0.0085 (6) | 0.0046 (6) | −0.0098 (5) |
O10 | 0.0505 (9) | 0.0483 (8) | 0.0375 (7) | 0.0012 (6) | 0.0249 (6) | −0.0142 (5) |
O11 | 0.0228 (7) | 0.0661 (9) | 0.0534 (8) | −0.0077 (6) | 0.0123 (6) | 0.0025 (7) |
O12 | 0.0481 (9) | 0.0355 (7) | 0.0578 (8) | −0.0175 (6) | 0.0240 (7) | −0.0008 (5) |
C1—N1 | 1.453 (2) | N2—O2 | 1.220 (2) |
C1—N3 | 1.461 (2) | N3—N4 | 1.423 (2) |
C1—C4 | 1.592 (2) | N4—O3 | 1.207 (2) |
C2—N7 | 1.448 (2) | N4—O4 | 1.211 (2) |
C2—N1 | 1.464 (2) | N5—N6 | 1.392 (2) |
C2—C3 | 1.573 (2) | N6—O6 | 1.208 (2) |
C3—N5 | 1.433 (2) | N6—O5 | 1.214 (2) |
C3—N3 | 1.473 (2) | N7—N8 | 1.415 (2) |
C4—N9 | 1.453 (2) | N8—O8 | 1.208 (2) |
C4—N11 | 1.460 (2) | N8—O7 | 1.212 (2) |
C5—N7 | 1.443 (2) | N9—N10 | 1.443 (2) |
C5—N9 | 1.486 (2) | N10—O9 | 1.207 (2) |
C5—C6 | 1.571 (2) | N10—O10 | 1.210 (2) |
C6—N5 | 1.438 (2) | N11—N12 | 1.374 (2) |
C6—N11 | 1.465 (2) | N12—O12 | 1.213 (2) |
N1—N2 | 1.403 (2) | N12—O11 | 1.219 (2) |
N2—O1 | 1.206 (2) | ||
N1—C1—N3 | 104.16 (11) | O3—N4—O4 | 127.28 (15) |
N1—C1—C4 | 109.36 (12) | O3—N4—N3 | 115.42 (14) |
N3—C1—C4 | 107.61 (11) | O4—N4—N3 | 117.16 (14) |
N7—C2—N1 | 110.66 (11) | N6—N5—C3 | 120.38 (11) |
N7—C2—C3 | 108.61 (11) | N6—N5—C6 | 119.78 (11) |
N1—C2—C3 | 104.38 (12) | C3—N5—C6 | 117.50 (11) |
N5—C3—N3 | 110.12 (11) | O6—N6—O5 | 127.18 (15) |
N5—C3—C2 | 109.00 (11) | O6—N6—N5 | 116.81 (13) |
N3—C3—C2 | 104.25 (11) | O5—N6—N5 | 115.92 (13) |
N9—C4—N11 | 99.54 (11) | N8—N7—C5 | 115.34 (11) |
N9—C4—C1 | 110.59 (11) | N8—N7—C2 | 114.12 (12) |
N11—C4—C1 | 113.00 (11) | C5—N7—C2 | 116.68 (12) |
N7—C5—N9 | 111.02 (11) | O8—N8—O7 | 126.73 (15) |
N7—C5—C6 | 108.34 (11) | O8—N8—N7 | 117.31 (13) |
N9—C5—C6 | 105.50 (12) | O7—N8—N7 | 115.90 (14) |
N5—C6—N11 | 113.20 (12) | N10—N9—C4 | 113.20 (12) |
N5—C6—C5 | 109.31 (11) | N10—N9—C5 | 112.02 (11) |
N11—C6—C5 | 100.00 (11) | C4—N9—C5 | 106.95 (11) |
N2—N1—C1 | 118.04 (12) | O9—N10—O10 | 126.90 (13) |
N2—N1—C2 | 118.87 (12) | O9—N10—N9 | 115.91 (13) |
C1—N1—C2 | 107.89 (11) | O10—N10—N9 | 117.10 (14) |
O1—N2—O2 | 126.28 (14) | N12—N11—C4 | 119.86 (12) |
O1—N2—N1 | 117.70 (14) | N12—N11—C6 | 120.48 (12) |
O2—N2—N1 | 115.95 (14) | C4—N11—C6 | 110.55 (11) |
N4—N3—C1 | 117.20 (12) | O12—N12—O11 | 126.61 (15) |
N4—N3—C3 | 116.46 (12) | O12—N12—N11 | 116.65 (14) |
C1—N3—C3 | 107.64 (11) | O11—N12—N11 | 116.71 (14) |
C6H6N12O12 | F(000) = 888 |
Mr = 438.23 | Dx = 1.938 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 13.1156 (7) Å | Cell parameters from 6489 reflections |
b = 8.1713 (4) Å | θ = 3.1–26.7° |
c = 14.8059 (8) Å | µ = 0.19 mm−1 |
β = 108.841 (1)° | T = 200 K |
V = 1501.75 (14) Å3 | Block |
Z = 4 | 0.37 × 0.33 × 0.18 mm |
Platform diffractometer | 3686 independent reflections |
Radiation source: Sealed Tube | 2875 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
ω scans | θmax = 28.3°, θmin = 2.5° |
Absorption correction: empirical :Multipole Expansion Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | h = −17→7 |
Tmin = 0.737, Tmax = 0.990 | k = −10→10 |
10149 measured reflections | l = −19→19 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Calculated w = 1/[σ2(Fo2) + (0.051P)2 + 0.1409P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.101 | (Δ/σ)max = 0.001 |
S = 1.04 | Δρmax = 0.34 e Å−3 |
3686 reflections | Δρmin = −0.24 e Å−3 |
296 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0078 (11) |
Primary atom site location: structure-invariant direct methods |
C6H6N12O12 | V = 1501.75 (14) Å3 |
Mr = 438.23 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 13.1156 (7) Å | µ = 0.19 mm−1 |
b = 8.1713 (4) Å | T = 200 K |
c = 14.8059 (8) Å | 0.37 × 0.33 × 0.18 mm |
β = 108.841 (1)° |
Platform diffractometer | 3686 independent reflections |
Absorption correction: empirical :Multipole Expansion Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | 2875 reflections with I > 2σ(I) |
Tmin = 0.737, Tmax = 0.990 | Rint = 0.036 |
10149 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 296 parameters |
wR(F2) = 0.101 | 0 restraints |
S = 1.04 | Δρmax = 0.34 e Å−3 |
3686 reflections | Δρmin = −0.24 e Å−3 |
Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS. No formal measure of the extent of decay is printed out by this program. The final unit cell is obtained from the refinement of the XYZ weighted centroids of reflections above 20 σ(I). |
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 0 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_obs 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. |
x | y | z | Uiso*/Ueq | ||
C1 | 1.10720 (11) | 0.5111 (2) | 0.32365 (9) | 0.0179 (3) | |
C2 | 0.93625 (11) | 0.5956 (2) | 0.32705 (9) | 0.0168 (3) | |
C3 | 1.00836 (11) | 0.7511 (2) | 0.33030 (9) | 0.0173 (3) | |
C4 | 1.08410 (12) | 0.4987 (2) | 0.21157 (9) | 0.0178 (3) | |
C5 | 0.90077 (11) | 0.5757 (2) | 0.15365 (9) | 0.0166 (3) | |
C6 | 0.97020 (11) | 0.7335 (2) | 0.15690 (9) | 0.0171 (3) | |
N1 | 1.01222 (10) | 0.45845 (14) | 0.34615 (8) | 0.0186 (3) | |
N2 | 1.02746 (11) | 0.36460 (14) | 0.42874 (8) | 0.0238 (3) | |
N3 | 1.11783 (9) | 0.68472 (14) | 0.34902 (8) | 0.0185 (2) | |
N4 | 1.19506 (10) | 0.7277 (2) | 0.43801 (8) | 0.0255 (3) | |
N5 | 0.97287 (10) | 0.83010 (13) | 0.23890 (8) | 0.0188 (3) | |
N6 | 0.96981 (12) | 0.99998 (15) | 0.23253 (9) | 0.0308 (3) | |
N7 | 0.85806 (9) | 0.58261 (13) | 0.23218 (8) | 0.0182 (2) | |
N8 | 0.77247 (11) | 0.4731 (2) | 0.22624 (10) | 0.0326 (3) | |
N9 | 0.97620 (10) | 0.43585 (13) | 0.16435 (7) | 0.0177 (2) | |
N10 | 0.96495 (11) | 0.35815 (14) | 0.07412 (8) | 0.0228 (3) | |
N11 | 1.07432 (10) | 0.65821 (14) | 0.16502 (8) | 0.0183 (2) | |
N12 | 1.16436 (10) | 0.7536 (2) | 0.17904 (8) | 0.0257 (3) | |
O1 | 1.11373 (11) | 0.29824 (15) | 0.46342 (8) | 0.0371 (3) | |
O2 | 0.94947 (10) | 0.35243 (13) | 0.45625 (7) | 0.0315 (3) | |
O3 | 1.18758 (11) | 0.86525 (15) | 0.46553 (8) | 0.0384 (3) | |
O4 | 1.26401 (10) | 0.6273 (2) | 0.47512 (8) | 0.0400 (3) | |
O5 | 0.98885 (15) | 1.07368 (14) | 0.30776 (9) | 0.0535 (4) | |
O6 | 0.94454 (12) | 1.05803 (13) | 0.15316 (8) | 0.0405 (3) | |
O7 | 0.75175 (11) | 0.4517 (2) | 0.29931 (9) | 0.0561 (4) | |
O8 | 0.72508 (11) | 0.4161 (2) | 0.14838 (9) | 0.0468 (4) | |
O9 | 0.87372 (10) | 0.34231 (13) | 0.02086 (7) | 0.0306 (3) | |
O10 | 1.04669 (10) | 0.30949 (14) | 0.06142 (8) | 0.0339 (3) | |
O11 | 1.25148 (9) | 0.6851 (2) | 0.20917 (9) | 0.0377 (3) | |
O12 | 1.14891 (10) | 0.89760 (14) | 0.15769 (8) | 0.0352 (3) | |
H1 | 1.1713 (14) | 0.4526 (19) | 0.3563 (11) | 0.018 (4)* | |
H2 | 0.8996 (14) | 0.6011 (18) | 0.3708 (11) | 0.019 (4)* | |
H3 | 1.0088 (14) | 0.827 (2) | 0.3782 (12) | 0.026 (4)* | |
H4 | 1.1379 (14) | 0.4329 (19) | 0.2004 (11) | 0.018 (4)* | |
H5 | 0.8437 (14) | 0.5633 (18) | 0.0976 (11) | 0.017 (4)* | |
H6 | 0.9434 (12) | 0.7964 (18) | 0.1026 (11) | 0.015 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0166 (7) | 0.0207 (7) | 0.0165 (6) | 0.0031 (5) | 0.0055 (5) | 0.0007 (5) |
C2 | 0.0157 (7) | 0.0201 (6) | 0.0159 (6) | −0.0014 (5) | 0.0069 (5) | −0.0007 (4) |
C3 | 0.0177 (7) | 0.0170 (6) | 0.0178 (6) | −0.0005 (5) | 0.0064 (5) | −0.0020 (5) |
C4 | 0.0183 (7) | 0.0209 (7) | 0.0149 (6) | 0.0019 (5) | 0.0065 (5) | −0.0002 (5) |
C5 | 0.0150 (7) | 0.0187 (6) | 0.0151 (6) | −0.0017 (5) | 0.0036 (5) | 0.0001 (4) |
C6 | 0.0190 (7) | 0.0164 (6) | 0.0153 (6) | −0.0013 (5) | 0.0046 (5) | 0.0011 (5) |
N1 | 0.0229 (6) | 0.0191 (6) | 0.0157 (5) | 0.0017 (5) | 0.0088 (5) | 0.0034 (4) |
N2 | 0.0371 (8) | 0.0188 (6) | 0.0153 (6) | −0.0019 (5) | 0.0082 (5) | 0.0003 (4) |
N3 | 0.0151 (6) | 0.0240 (6) | 0.0146 (5) | −0.0025 (5) | 0.0022 (4) | −0.0033 (4) |
N4 | 0.0180 (6) | 0.0369 (7) | 0.0193 (6) | −0.0066 (5) | 0.0029 (5) | −0.0036 (5) |
N5 | 0.0244 (6) | 0.0126 (5) | 0.0189 (6) | 0.0005 (4) | 0.0060 (5) | 0.0004 (4) |
N6 | 0.0426 (8) | 0.0152 (6) | 0.0333 (7) | 0.0001 (6) | 0.0103 (6) | −0.0003 (5) |
N7 | 0.0128 (6) | 0.0236 (6) | 0.0188 (6) | −0.0036 (4) | 0.0058 (5) | −0.0013 (4) |
N8 | 0.0223 (7) | 0.0475 (8) | 0.0286 (7) | −0.0155 (6) | 0.0088 (6) | −0.0019 (6) |
N9 | 0.0230 (6) | 0.0174 (5) | 0.0137 (5) | −0.0004 (5) | 0.0072 (5) | −0.0027 (4) |
N10 | 0.0353 (8) | 0.0187 (6) | 0.0166 (6) | −0.0034 (5) | 0.0115 (5) | −0.0016 (4) |
N11 | 0.0167 (6) | 0.0222 (6) | 0.0171 (5) | −0.0033 (5) | 0.0072 (4) | 0.0009 (4) |
N12 | 0.0227 (7) | 0.0343 (7) | 0.0223 (6) | −0.0094 (5) | 0.0101 (5) | −0.0028 (5) |
O1 | 0.0453 (8) | 0.0366 (6) | 0.0257 (6) | 0.0112 (6) | 0.0064 (5) | 0.0120 (5) |
O2 | 0.0448 (8) | 0.0297 (6) | 0.0263 (6) | −0.0089 (5) | 0.0201 (5) | 0.0015 (4) |
O3 | 0.0386 (8) | 0.0362 (7) | 0.0330 (6) | −0.0105 (5) | 0.0013 (5) | −0.0132 (5) |
O4 | 0.0245 (6) | 0.0557 (8) | 0.0299 (6) | 0.0066 (6) | −0.0049 (5) | −0.0033 (5) |
O5 | 0.1003 (13) | 0.0196 (6) | 0.0352 (7) | −0.0021 (6) | 0.0143 (7) | −0.0087 (5) |
O6 | 0.0652 (10) | 0.0207 (6) | 0.0340 (6) | 0.0027 (6) | 0.0136 (6) | 0.0094 (4) |
O7 | 0.0398 (8) | 0.0994 (12) | 0.0343 (7) | −0.0389 (8) | 0.0190 (6) | −0.0051 (7) |
O8 | 0.0387 (8) | 0.0665 (9) | 0.0325 (7) | −0.0342 (7) | 0.0077 (6) | −0.0108 (6) |
O9 | 0.0364 (7) | 0.0314 (6) | 0.0198 (5) | −0.0067 (5) | 0.0031 (5) | −0.0074 (4) |
O10 | 0.0391 (7) | 0.0383 (6) | 0.0303 (6) | 0.0010 (5) | 0.0194 (5) | −0.0106 (5) |
O11 | 0.0183 (6) | 0.0515 (8) | 0.0434 (7) | −0.0048 (5) | 0.0104 (5) | 0.0022 (5) |
O12 | 0.0375 (7) | 0.0281 (6) | 0.0439 (7) | −0.0129 (5) | 0.0184 (6) | −0.0003 (5) |
C1—N1 | 1.455 (2) | N2—O2 | 1.221 (2) |
C1—N3 | 1.462 (2) | N3—N4 | 1.422 (2) |
C1—C4 | 1.591 (2) | N4—O3 | 1.211 (2) |
C2—N7 | 1.451 (2) | N4—O4 | 1.213 (2) |
C2—N1 | 1.465 (2) | N5—N6 | 1.391 (2) |
C2—C3 | 1.576 (2) | N6—O6 | 1.210 (2) |
C3—N5 | 1.434 (2) | N6—O5 | 1.219 (2) |
C3—N3 | 1.475 (2) | N7—N8 | 1.416 (2) |
C4—N9 | 1.455 (2) | N8—O7 | 1.210 (2) |
C4—N11 | 1.460 (2) | N8—O8 | 1.212 (2) |
C5—N7 | 1.446 (2) | N9—N10 | 1.4431 (15) |
C5—N9 | 1.486 (2) | N10—O9 | 1.209 (2) |
C5—C6 | 1.570 (2) | N10—O10 | 1.214 (2) |
C6—N5 | 1.439 (2) | N11—N12 | 1.373 (2) |
C6—N11 | 1.467 (2) | N12—O12 | 1.218 (2) |
N1—N2 | 1.402 (2) | N12—O11 | 1.220 (2) |
N2—O1 | 1.209 (2) | ||
N1—C1—N3 | 104.23 (10) | O3—N4—O4 | 127.24 (13) |
N1—C1—C4 | 109.35 (11) | O3—N4—N3 | 115.46 (12) |
N3—C1—C4 | 107.45 (10) | O4—N4—N3 | 117.16 (12) |
N7—C2—N1 | 110.77 (10) | N6—N5—C3 | 120.41 (11) |
N7—C2—C3 | 108.56 (10) | N6—N5—C6 | 119.86 (10) |
N1—C2—C3 | 104.30 (11) | C3—N5—C6 | 117.47 (10) |
N5—C3—N3 | 110.02 (11) | O6—N6—O5 | 127.21 (13) |
N5—C3—C2 | 108.98 (11) | O6—N6—N5 | 116.74 (12) |
N3—C3—C2 | 104.31 (10) | O5—N6—N5 | 115.99 (12) |
N9—C4—N11 | 99.49 (10) | N8—N7—C5 | 115.51 (11) |
N9—C4—C1 | 110.60 (11) | N8—N7—C2 | 113.88 (11) |
N11—C4—C1 | 113.18 (10) | C5—N7—C2 | 116.43 (11) |
N7—C5—N9 | 111.22 (10) | O7—N8—O8 | 126.89 (14) |
N7—C5—C6 | 108.35 (10) | O7—N8—N7 | 115.99 (12) |
N9—C5—C6 | 105.58 (11) | O8—N8—N7 | 117.05 (12) |
N5—C6—N11 | 113.11 (11) | N10—N9—C4 | 113.14 (11) |
N5—C6—C5 | 109.39 (11) | N10—N9—C5 | 111.97 (10) |
N11—C6—C5 | 99.99 (10) | C4—N9—C5 | 106.87 (10) |
N2—N1—C1 | 118.05 (11) | O9—N10—O10 | 126.99 (12) |
N2—N1—C2 | 118.90 (11) | O9—N10—N9 | 115.77 (12) |
C1—N1—C2 | 107.98 (10) | O10—N10—N9 | 117.15 (12) |
O1—N2—O2 | 126.26 (12) | N12—N11—C4 | 119.66 (11) |
O1—N2—N1 | 117.77 (12) | N12—N11—C6 | 120.44 (11) |
O2—N2—N1 | 115.89 (13) | C4—N11—C6 | 110.52 (10) |
N4—N3—C1 | 117.22 (11) | O12—N12—O11 | 126.54 (13) |
N4—N3—C3 | 116.23 (11) | O12—N12—N11 | 116.48 (13) |
C1—N3—C3 | 107.60 (10) | O11—N12—N11 | 116.94 (12) |
C6H6N12O12 | F(000) = 888 |
Mr = 438.23 | Dx = 1.947 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 13.0698 (4) Å | Cell parameters from 6836 reflections |
b = 8.1737 (3) Å | θ = 3.1–26.7° |
c = 14.7718 (5) Å | µ = 0.19 mm−1 |
β = 108.696 (1)° | T = 150 K |
V = 1494.78 (9) Å3 | Block |
Z = 4 | 0.37 × 0.33 × 0.18 mm |
Platform diffractometer | 3678 independent reflections |
Radiation source: Sealed Tube | 2981 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
ω scans | θmax = 28.3°, θmin = 2.5° |
Absorption correction: empirical :Multipole Expansion Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | h = −17→7 |
Tmin = 0.776, Tmax = 0.990 | k = −10→10 |
10088 measured reflections | l = −19→19 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | Calculated w = 1/[σ2(Fo2) + (0.0493P)2 + 0.1643P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.095 | (Δ/σ)max = −0.001 |
S = 1.04 | Δρmax = 0.32 e Å−3 |
3678 reflections | Δρmin = −0.26 e Å−3 |
296 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0074 (11) |
Primary atom site location: structure-invariant direct methods |
C6H6N12O12 | V = 1494.78 (9) Å3 |
Mr = 438.23 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 13.0698 (4) Å | µ = 0.19 mm−1 |
b = 8.1737 (3) Å | T = 150 K |
c = 14.7718 (5) Å | 0.37 × 0.33 × 0.18 mm |
β = 108.696 (1)° |
Platform diffractometer | 3678 independent reflections |
Absorption correction: empirical :Multipole Expansion Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | 2981 reflections with I > 2σ(I) |
Tmin = 0.776, Tmax = 0.990 | Rint = 0.034 |
10088 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 296 parameters |
wR(F2) = 0.095 | 0 restraints |
S = 1.04 | Δρmax = 0.32 e Å−3 |
3678 reflections | Δρmin = −0.26 e Å−3 |
Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS. No formal measure of the extent of decay is printed out by this program. The final unit cell is obtained from the refinement of the XYZ weighted centroids of reflections above 20 σ(I). |
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 0 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_obs 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. |
x | y | z | Uiso*/Ueq | ||
C1 | 1.10726 (11) | 0.5103 (2) | 0.32378 (9) | 0.0142 (3) | |
C2 | 0.93615 (11) | 0.59724 (15) | 0.32746 (9) | 0.0136 (3) | |
C3 | 1.00915 (11) | 0.75182 (15) | 0.33048 (9) | 0.0139 (3) | |
C4 | 1.08430 (11) | 0.49759 (15) | 0.21156 (9) | 0.0143 (3) | |
C5 | 0.90041 (11) | 0.57671 (15) | 0.15361 (9) | 0.0136 (3) | |
C6 | 0.97084 (11) | 0.73366 (15) | 0.15673 (9) | 0.0139 (3) | |
N1 | 1.01165 (9) | 0.45888 (13) | 0.34637 (7) | 0.0148 (2) | |
N2 | 1.02649 (10) | 0.36479 (13) | 0.42896 (8) | 0.0187 (3) | |
N3 | 1.11873 (9) | 0.68410 (13) | 0.34911 (7) | 0.0149 (2) | |
N4 | 1.19613 (9) | 0.72646 (15) | 0.43823 (8) | 0.0197 (3) | |
N5 | 0.97397 (9) | 0.83042 (12) | 0.23902 (7) | 0.0150 (2) | |
N6 | 0.97140 (11) | 1.00083 (14) | 0.23260 (9) | 0.0235 (3) | |
N7 | 0.85770 (9) | 0.58446 (13) | 0.23261 (7) | 0.0146 (2) | |
N8 | 0.77116 (10) | 0.4758 (2) | 0.22663 (9) | 0.0250 (3) | |
N9 | 0.97559 (9) | 0.43555 (13) | 0.16437 (7) | 0.0142 (2) | |
N10 | 0.96409 (10) | 0.35832 (13) | 0.07394 (7) | 0.0178 (2) | |
N11 | 1.07511 (9) | 0.65711 (13) | 0.16477 (7) | 0.0145 (2) | |
N12 | 1.16552 (10) | 0.75212 (14) | 0.17898 (8) | 0.0196 (3) | |
O1 | 1.11291 (9) | 0.29777 (13) | 0.46367 (7) | 0.0280 (3) | |
O2 | 0.94769 (9) | 0.35343 (12) | 0.45644 (7) | 0.0241 (2) | |
O3 | 1.18930 (9) | 0.86484 (13) | 0.46548 (7) | 0.0294 (3) | |
O4 | 1.26482 (9) | 0.62540 (14) | 0.47553 (7) | 0.0300 (3) | |
O5 | 0.99010 (13) | 1.07447 (13) | 0.30782 (8) | 0.0405 (3) | |
O6 | 0.94683 (10) | 1.05842 (12) | 0.15298 (7) | 0.0307 (3) | |
O7 | 0.75003 (10) | 0.4560 (2) | 0.30015 (8) | 0.0428 (3) | |
O8 | 0.72381 (10) | 0.41806 (15) | 0.14881 (8) | 0.0355 (3) | |
O9 | 0.87237 (9) | 0.34196 (12) | 0.02101 (7) | 0.0239 (2) | |
O10 | 1.04614 (9) | 0.31042 (13) | 0.06036 (7) | 0.0258 (2) | |
O11 | 1.25286 (8) | 0.68271 (14) | 0.20910 (8) | 0.0288 (3) | |
O12 | 1.15046 (9) | 0.89649 (12) | 0.15786 (8) | 0.0270 (3) | |
H1 | 1.1714 (13) | 0.4487 (18) | 0.3565 (11) | 0.016 (4)* | |
H2 | 0.8981 (13) | 0.6033 (18) | 0.3717 (11) | 0.016 (4)* | |
H3 | 1.0101 (13) | 0.8252 (18) | 0.3785 (11) | 0.016 (4)* | |
H4 | 1.1383 (13) | 0.4288 (18) | 0.1998 (10) | 0.015 (4)* | |
H5 | 0.8442 (13) | 0.5661 (17) | 0.0961 (11) | 0.012 (4)* | |
H6 | 0.9455 (12) | 0.7951 (18) | 0.1022 (11) | 0.013 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0137 (6) | 0.0167 (6) | 0.0126 (6) | 0.0022 (5) | 0.0048 (5) | 0.0009 (4) |
C2 | 0.0131 (6) | 0.0152 (6) | 0.0133 (6) | −0.0005 (5) | 0.0053 (5) | −0.0005 (4) |
C3 | 0.0141 (6) | 0.0142 (6) | 0.0138 (6) | −0.0007 (5) | 0.0051 (5) | −0.0010 (4) |
C4 | 0.0152 (6) | 0.0158 (6) | 0.0125 (6) | 0.0010 (5) | 0.0055 (5) | 0.0001 (4) |
C5 | 0.0135 (6) | 0.0151 (6) | 0.0118 (6) | −0.0011 (5) | 0.0034 (5) | −0.0002 (4) |
C6 | 0.0148 (6) | 0.0144 (6) | 0.0122 (6) | −0.0011 (5) | 0.0040 (5) | 0.0008 (4) |
N1 | 0.0171 (6) | 0.0154 (5) | 0.0130 (5) | 0.0014 (4) | 0.0063 (4) | 0.0029 (4) |
N2 | 0.0284 (7) | 0.0152 (5) | 0.0125 (5) | −0.0016 (5) | 0.0068 (5) | −0.0002 (4) |
N3 | 0.0122 (5) | 0.0187 (5) | 0.0120 (5) | −0.0019 (4) | 0.0015 (4) | −0.0024 (4) |
N4 | 0.0146 (6) | 0.0283 (6) | 0.0151 (5) | −0.0054 (5) | 0.0030 (4) | −0.0021 (4) |
N5 | 0.0202 (6) | 0.0096 (5) | 0.0149 (5) | 0.0001 (4) | 0.0053 (4) | 0.0004 (4) |
N6 | 0.0323 (7) | 0.0118 (5) | 0.0254 (6) | −0.0003 (5) | 0.0078 (5) | −0.0003 (4) |
N7 | 0.0106 (5) | 0.0188 (5) | 0.0149 (5) | −0.0037 (4) | 0.0049 (4) | −0.0012 (4) |
N8 | 0.0173 (6) | 0.0359 (7) | 0.0220 (6) | −0.0109 (5) | 0.0064 (5) | −0.0015 (5) |
N9 | 0.0178 (6) | 0.0148 (5) | 0.0105 (5) | 0.0002 (4) | 0.0053 (4) | −0.0018 (4) |
N10 | 0.0277 (7) | 0.0150 (5) | 0.0123 (5) | −0.0028 (5) | 0.0085 (5) | −0.0012 (4) |
N11 | 0.0140 (5) | 0.0167 (5) | 0.0134 (5) | −0.0026 (4) | 0.0052 (4) | 0.0006 (4) |
N12 | 0.0176 (6) | 0.0266 (6) | 0.0164 (5) | −0.0069 (5) | 0.0077 (5) | −0.0018 (4) |
O1 | 0.0340 (6) | 0.0273 (5) | 0.0201 (5) | 0.0086 (5) | 0.0049 (5) | 0.0083 (4) |
O2 | 0.0335 (6) | 0.0236 (5) | 0.0202 (5) | −0.0071 (4) | 0.0154 (5) | 0.0009 (4) |
O3 | 0.0295 (6) | 0.0280 (6) | 0.0258 (5) | −0.0081 (5) | 0.0022 (5) | −0.0097 (4) |
O4 | 0.0196 (6) | 0.0414 (6) | 0.0223 (5) | 0.0049 (5) | −0.0029 (4) | −0.0017 (4) |
O5 | 0.0740 (10) | 0.0160 (5) | 0.0273 (6) | −0.0016 (5) | 0.0102 (6) | −0.0078 (4) |
O6 | 0.0488 (8) | 0.0164 (5) | 0.0257 (6) | 0.0022 (5) | 0.0104 (5) | 0.0072 (4) |
O7 | 0.0321 (7) | 0.0741 (9) | 0.0265 (6) | −0.0284 (7) | 0.0156 (5) | −0.0038 (6) |
O8 | 0.0292 (6) | 0.0503 (7) | 0.0251 (6) | −0.0244 (5) | 0.0061 (5) | −0.0077 (5) |
O9 | 0.0280 (6) | 0.0247 (5) | 0.0161 (5) | −0.0053 (4) | 0.0031 (4) | −0.0050 (4) |
O10 | 0.0294 (6) | 0.0300 (6) | 0.0227 (5) | 0.0009 (5) | 0.0151 (5) | −0.0076 (4) |
O11 | 0.0152 (5) | 0.0385 (6) | 0.0326 (6) | −0.0020 (5) | 0.0075 (4) | 0.0022 (5) |
O12 | 0.0286 (6) | 0.0217 (5) | 0.0334 (6) | −0.0093 (4) | 0.0137 (5) | −0.0002 (4) |
C1—N1 | 1.455 (2) | N2—O2 | 1.226 (2) |
C1—N3 | 1.464 (2) | N3—N4 | 1.422 (2) |
C1—C4 | 1.591 (2) | N4—O3 | 1.213 (2) |
C2—N7 | 1.451 (2) | N4—O4 | 1.214 (2) |
C2—N1 | 1.468 (2) | N5—N6 | 1.3958 (15) |
C2—C3 | 1.575 (2) | N6—O6 | 1.211 (2) |
C3—N5 | 1.432 (2) | N6—O5 | 1.218 (2) |
C3—N3 | 1.477 (2) | N7—N8 | 1.419 (2) |
C4—N9 | 1.458 (2) | N8—O8 | 1.213 (2) |
C4—N11 | 1.463 (2) | N8—O7 | 1.214 (2) |
C5—N7 | 1.447 (2) | N9—N10 | 1.4411 (14) |
C5—N9 | 1.491 (2) | N10—O9 | 1.210 (2) |
C5—C6 | 1.571 (2) | N10—O10 | 1.217 (2) |
C6—N5 | 1.440 (2) | N11—N12 | 1.373 (2) |
C6—N11 | 1.469 (2) | N12—O12 | 1.220 (2) |
N1—N2 | 1.4021 (14) | N12—O11 | 1.224 (2) |
N2—O1 | 1.211 (2) | ||
N1—C1—N3 | 104.28 (10) | O3—N4—O4 | 127.29 (12) |
N1—C1—C4 | 109.34 (10) | O3—N4—N3 | 115.34 (11) |
N3—C1—C4 | 107.42 (9) | O4—N4—N3 | 117.22 (11) |
N7—C2—N1 | 110.62 (10) | N6—N5—C3 | 120.35 (10) |
N7—C2—C3 | 108.61 (10) | N6—N5—C6 | 119.82 (10) |
N1—C2—C3 | 104.38 (10) | C3—N5—C6 | 117.62 (10) |
N5—C3—N3 | 110.06 (10) | O6—N6—O5 | 127.41 (12) |
N5—C3—C2 | 108.95 (10) | O6—N6—N5 | 116.56 (11) |
N3—C3—C2 | 104.31 (10) | O5—N6—N5 | 115.97 (11) |
N9—C4—N11 | 99.46 (10) | N8—N7—C5 | 115.36 (10) |
N9—C4—C1 | 110.51 (10) | N8—N7—C2 | 114.06 (10) |
N11—C4—C1 | 113.19 (10) | C5—N7—C2 | 116.50 (10) |
N7—C5—N9 | 111.06 (10) | O8—N8—O7 | 127.07 (13) |
N7—C5—C6 | 108.32 (10) | O8—N8—N7 | 117.19 (11) |
N9—C5—C6 | 105.60 (10) | O7—N8—N7 | 115.67 (11) |
N5—C6—N11 | 113.02 (10) | N10—N9—C4 | 113.05 (10) |
N5—C6—C5 | 109.34 (10) | N10—N9—C5 | 111.77 (10) |
N11—C6—C5 | 100.03 (9) | C4—N9—C5 | 106.84 (10) |
N2—N1—C1 | 117.94 (11) | O9—N10—O10 | 126.91 (11) |
N2—N1—C2 | 119.04 (10) | O9—N10—N9 | 115.75 (11) |
C1—N1—C2 | 107.96 (10) | O10—N10—N9 | 117.25 (11) |
O1—N2—O2 | 126.45 (11) | N12—N11—C4 | 119.73 (11) |
O1—N2—N1 | 117.81 (11) | N12—N11—C6 | 120.14 (10) |
O2—N2—N1 | 115.66 (11) | C4—N11—C6 | 110.57 (10) |
N4—N3—C1 | 117.18 (10) | O12—N12—O11 | 126.62 (12) |
N4—N3—C3 | 116.16 (10) | O12—N12—N11 | 116.59 (12) |
C1—N3—C3 | 107.60 (10) | O11—N12—N11 | 116.76 (11) |
C6H6N12O12 | F(000) = 888 |
Mr = 438.23 | Dx = 1.954 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 13.0342 (3) Å | Cell parameters from 7099 reflections |
b = 8.1773 (2) Å | θ = 3.1–26.7° |
c = 14.7465 (2) Å | µ = 0.19 mm−1 |
β = 108.566 (1)° | T = 100 K |
V = 1489.95 (5) Å3 | Block |
Z = 4 | 0.37 × 0.33 × 0.18 mm |
Platform diffractometer | 3658 independent reflections |
Radiation source: Sealed Tube | 3005 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
ω scans | θmax = 28.3°, θmin = 2.5° |
Absorption correction: empirical :Multipole Expansion Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | h = −17→7 |
Tmin = 0.772, Tmax = 0.990 | k = −10→10 |
9973 measured reflections | l = −19→19 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | Calculated w = 1/[σ2(Fo2) + (0.0525P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.093 | (Δ/σ)max = 0.001 |
S = 1.04 | Δρmax = 0.38 e Å−3 |
3658 reflections | Δρmin = −0.28 e Å−3 |
296 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0083 (11) |
Primary atom site location: structure-invariant direct methods |
C6H6N12O12 | V = 1489.95 (5) Å3 |
Mr = 438.23 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 13.0342 (3) Å | µ = 0.19 mm−1 |
b = 8.1773 (2) Å | T = 100 K |
c = 14.7465 (2) Å | 0.37 × 0.33 × 0.18 mm |
β = 108.566 (1)° |
Platform diffractometer | 3658 independent reflections |
Absorption correction: empirical :Multipole Expansion Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | 3005 reflections with I > 2σ(I) |
Tmin = 0.772, Tmax = 0.990 | Rint = 0.036 |
9973 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 296 parameters |
wR(F2) = 0.093 | 0 restraints |
S = 1.04 | Δρmax = 0.38 e Å−3 |
3658 reflections | Δρmin = −0.28 e Å−3 |
Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS. No formal measure of the extent of decay is printed out by this program. The final unit cell is obtained from the refinement of the XYZ weighted centroids of reflections above 20 σ(I). |
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 0 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_obs 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. |
x | y | z | Uiso*/Ueq | ||
C1 | 1.10727 (11) | 0.50974 (14) | 0.32381 (8) | 0.0105 (2) | |
C2 | 0.93592 (10) | 0.59834 (14) | 0.32778 (8) | 0.0100 (2) | |
C3 | 1.00962 (10) | 0.75247 (14) | 0.33073 (8) | 0.0099 (2) | |
C4 | 1.08423 (11) | 0.49692 (14) | 0.21143 (8) | 0.0104 (2) | |
C5 | 0.90035 (11) | 0.57728 (14) | 0.15385 (9) | 0.0100 (2) | |
C6 | 0.97135 (10) | 0.73394 (14) | 0.15666 (8) | 0.0100 (2) | |
N1 | 1.01135 (9) | 0.45952 (12) | 0.34664 (7) | 0.0111 (2) | |
N2 | 1.02541 (10) | 0.36499 (13) | 0.42906 (7) | 0.0133 (2) | |
N3 | 1.11940 (9) | 0.68354 (12) | 0.34915 (7) | 0.0105 (2) | |
N4 | 1.19704 (9) | 0.72571 (13) | 0.43841 (7) | 0.0138 (2) | |
N5 | 0.97493 (9) | 0.83092 (12) | 0.23918 (7) | 0.0107 (2) | |
N6 | 0.97257 (10) | 1.00135 (13) | 0.23254 (8) | 0.0165 (2) | |
N7 | 0.85735 (9) | 0.58604 (12) | 0.23289 (7) | 0.0110 (2) | |
N8 | 0.77013 (9) | 0.47805 (14) | 0.22725 (8) | 0.0171 (2) | |
N9 | 0.97526 (9) | 0.43563 (12) | 0.16447 (7) | 0.0102 (2) | |
N10 | 0.96331 (9) | 0.35854 (12) | 0.07362 (7) | 0.0125 (2) | |
N11 | 1.07558 (9) | 0.65640 (12) | 0.16451 (7) | 0.0105 (2) | |
N12 | 1.16654 (9) | 0.75069 (13) | 0.17876 (7) | 0.0138 (2) | |
O1 | 1.11202 (9) | 0.29716 (12) | 0.46395 (7) | 0.0198 (2) | |
O2 | 0.94622 (8) | 0.35409 (11) | 0.45655 (6) | 0.0171 (2) | |
O3 | 1.19055 (9) | 0.86472 (12) | 0.46543 (7) | 0.0206 (2) | |
O4 | 1.26541 (8) | 0.62406 (12) | 0.47593 (7) | 0.0212 (2) | |
O5 | 0.99071 (11) | 1.07556 (12) | 0.30786 (7) | 0.0282 (3) | |
O6 | 0.94865 (9) | 1.05874 (11) | 0.15268 (7) | 0.0215 (2) | |
O7 | 0.74863 (9) | 0.45946 (15) | 0.30095 (7) | 0.0294 (3) | |
O8 | 0.72269 (9) | 0.41955 (13) | 0.14925 (7) | 0.0247 (2) | |
O9 | 0.87133 (8) | 0.34172 (11) | 0.02114 (6) | 0.0168 (2) | |
O10 | 1.04581 (8) | 0.31104 (12) | 0.05955 (6) | 0.0182 (2) | |
O11 | 1.25407 (8) | 0.68108 (12) | 0.20910 (7) | 0.0202 (2) | |
O12 | 1.15173 (8) | 0.89558 (11) | 0.15797 (7) | 0.0188 (2) | |
H1 | 1.1707 (13) | 0.4509 (18) | 0.3561 (10) | 0.012 (4)* | |
H2 | 0.9008 (13) | 0.6025 (17) | 0.3731 (11) | 0.012 (4)* | |
H3 | 1.0112 (12) | 0.8277 (18) | 0.3802 (11) | 0.012 (4)* | |
H4 | 1.1377 (13) | 0.4298 (18) | 0.1997 (10) | 0.011 (4)* | |
H5 | 0.8460 (13) | 0.5697 (17) | 0.0968 (10) | 0.008 (3)* | |
H6 | 0.9426 (12) | 0.7980 (17) | 0.1008 (10) | 0.007 (3)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0101 (6) | 0.0116 (6) | 0.0106 (6) | 0.0009 (5) | 0.0042 (5) | 0.0004 (4) |
C2 | 0.0096 (6) | 0.0113 (6) | 0.0097 (6) | 0.0004 (4) | 0.0041 (5) | 0.0003 (4) |
C3 | 0.0098 (6) | 0.0096 (5) | 0.0105 (6) | −0.0004 (4) | 0.0036 (5) | −0.0005 (4) |
C4 | 0.0112 (6) | 0.0114 (6) | 0.0097 (6) | 0.0008 (5) | 0.0046 (5) | 0.0005 (4) |
C5 | 0.0096 (6) | 0.0112 (5) | 0.0090 (6) | 0.0000 (4) | 0.0027 (5) | 0.0004 (4) |
C6 | 0.0107 (6) | 0.0098 (5) | 0.0094 (5) | −0.0006 (4) | 0.0030 (5) | −0.0003 (4) |
N1 | 0.0124 (6) | 0.0121 (5) | 0.0100 (5) | 0.0014 (4) | 0.0051 (4) | 0.0025 (4) |
N2 | 0.0198 (6) | 0.0112 (5) | 0.0091 (5) | −0.0014 (4) | 0.0048 (4) | −0.0009 (4) |
N3 | 0.0085 (5) | 0.0126 (5) | 0.0087 (5) | −0.0012 (4) | 0.0006 (4) | −0.0015 (3) |
N4 | 0.0100 (5) | 0.0198 (5) | 0.0111 (5) | −0.0039 (4) | 0.0025 (4) | −0.0018 (4) |
N5 | 0.0152 (6) | 0.0062 (5) | 0.0108 (5) | 0.0007 (4) | 0.0041 (4) | 0.0006 (3) |
N6 | 0.0218 (6) | 0.0093 (5) | 0.0182 (6) | 0.0000 (4) | 0.0061 (5) | −0.0004 (4) |
N7 | 0.0081 (5) | 0.0142 (5) | 0.0110 (5) | −0.0028 (4) | 0.0037 (4) | −0.0009 (4) |
N8 | 0.0113 (6) | 0.0241 (6) | 0.0162 (5) | −0.0061 (5) | 0.0047 (4) | −0.0004 (4) |
N9 | 0.0122 (6) | 0.0104 (5) | 0.0085 (5) | −0.0001 (4) | 0.0039 (4) | −0.0019 (3) |
N10 | 0.0187 (6) | 0.0101 (5) | 0.0097 (5) | −0.0020 (4) | 0.0060 (4) | −0.0007 (4) |
N11 | 0.0087 (5) | 0.0118 (5) | 0.0115 (5) | −0.0012 (4) | 0.0040 (4) | 0.0009 (4) |
N12 | 0.0122 (6) | 0.0188 (5) | 0.0115 (5) | −0.0043 (4) | 0.0054 (4) | −0.0018 (4) |
O1 | 0.0227 (6) | 0.0203 (5) | 0.0146 (5) | 0.0058 (4) | 0.0035 (4) | 0.0049 (4) |
O2 | 0.0219 (6) | 0.0175 (5) | 0.0153 (5) | −0.0047 (4) | 0.0108 (4) | 0.0002 (3) |
O3 | 0.0204 (6) | 0.0190 (5) | 0.0192 (5) | −0.0055 (4) | 0.0020 (4) | −0.0068 (4) |
O4 | 0.0135 (5) | 0.0284 (5) | 0.0170 (5) | 0.0040 (4) | −0.0017 (4) | −0.0002 (4) |
O5 | 0.0502 (8) | 0.0119 (5) | 0.0194 (5) | −0.0012 (5) | 0.0069 (5) | −0.0054 (3) |
O6 | 0.0333 (6) | 0.0126 (5) | 0.0182 (5) | 0.0018 (4) | 0.0075 (4) | 0.0055 (3) |
O7 | 0.0215 (6) | 0.0515 (7) | 0.0184 (5) | −0.0178 (5) | 0.0108 (4) | −0.0021 (5) |
O8 | 0.0207 (6) | 0.0345 (6) | 0.0173 (5) | −0.0161 (5) | 0.0037 (4) | −0.0055 (4) |
O9 | 0.0188 (5) | 0.0173 (5) | 0.0123 (4) | −0.0040 (4) | 0.0021 (4) | −0.0032 (3) |
O10 | 0.0202 (6) | 0.0209 (5) | 0.0169 (5) | 0.0012 (4) | 0.0105 (4) | −0.0047 (3) |
O11 | 0.0099 (5) | 0.0273 (5) | 0.0234 (5) | −0.0006 (4) | 0.0054 (4) | 0.0020 (4) |
O12 | 0.0206 (6) | 0.0141 (5) | 0.0236 (5) | −0.0060 (4) | 0.0096 (4) | 0.0000 (3) |
C1—N1 | 1.454 (2) | N2—O2 | 1.2264 (15) |
C1—N3 | 1.4652 (15) | N3—N4 | 1.4239 (14) |
C1—C4 | 1.591 (2) | N4—O4 | 1.2154 (15) |
C2—N7 | 1.451 (2) | N4—O3 | 1.2164 (14) |
C2—N1 | 1.469 (2) | N5—N6 | 1.3968 (14) |
C2—C3 | 1.577 (2) | N6—O6 | 1.2126 (14) |
C3—N5 | 1.4318 (15) | N6—O5 | 1.2208 (14) |
C3—N3 | 1.480 (2) | N7—N8 | 1.4210 (15) |
C4—N9 | 1.457 (2) | N8—O7 | 1.2151 (14) |
C4—N11 | 1.4638 (15) | N8—O8 | 1.2170 (15) |
C5—N7 | 1.447 (2) | N9—N10 | 1.4434 (13) |
C5—N9 | 1.491 (2) | N10—O9 | 1.2101 (15) |
C5—C6 | 1.573 (2) | N10—O10 | 1.2217 (15) |
C6—N5 | 1.4407 (14) | N11—N12 | 1.3732 (15) |
C6—N11 | 1.470 (2) | N12—O12 | 1.2236 (14) |
N1—N2 | 1.4024 (14) | N12—O11 | 1.2251 (15) |
N2—O1 | 1.2153 (15) | ||
N1—C1—N3 | 104.23 (9) | O4—N4—O3 | 127.40 (11) |
N1—C1—C4 | 109.37 (10) | O4—N4—N3 | 117.22 (10) |
N3—C1—C4 | 107.39 (9) | O3—N4—N3 | 115.22 (10) |
N7—C2—N1 | 110.69 (9) | N6—N5—C3 | 120.43 (9) |
N7—C2—C3 | 108.59 (9) | N6—N5—C6 | 119.73 (9) |
N1—C2—C3 | 104.32 (10) | C3—N5—C6 | 117.73 (9) |
N5—C3—N3 | 109.89 (10) | O6—N6—O5 | 127.34 (11) |
N5—C3—C2 | 108.99 (10) | O6—N6—N5 | 116.57 (10) |
N3—C3—C2 | 104.21 (9) | O5—N6—N5 | 116.02 (10) |
N9—C4—N11 | 99.50 (9) | N8—N7—C5 | 115.47 (9) |
N9—C4—C1 | 110.49 (10) | N8—N7—C2 | 113.92 (9) |
N11—C4—C1 | 113.22 (9) | C5—N7—C2 | 116.42 (10) |
N7—C5—N9 | 111.26 (9) | O7—N8—O8 | 127.13 (12) |
N7—C5—C6 | 108.30 (9) | O7—N8—N7 | 115.69 (10) |
N9—C5—C6 | 105.66 (10) | O8—N8—N7 | 117.12 (10) |
N5—C6—N11 | 112.98 (10) | N10—N9—C4 | 113.10 (9) |
N5—C6—C5 | 109.33 (9) | N10—N9—C5 | 111.62 (9) |
N11—C6—C5 | 99.90 (9) | C4—N9—C5 | 106.82 (9) |
N2—N1—C1 | 118.15 (10) | O9—N10—O10 | 126.99 (10) |
N2—N1—C2 | 119.00 (10) | O9—N10—N9 | 115.81 (10) |
C1—N1—C2 | 108.12 (9) | O10—N10—N9 | 117.12 (10) |
O1—N2—O2 | 126.36 (11) | N12—N11—C4 | 119.68 (10) |
O1—N2—N1 | 117.77 (10) | N12—N11—C6 | 120.07 (10) |
O2—N2—N1 | 115.79 (11) | C4—N11—C6 | 110.59 (9) |
N4—N3—C1 | 117.25 (10) | O12—N12—O11 | 126.56 (11) |
N4—N3—C3 | 116.00 (9) | O12—N12—N11 | 116.47 (11) |
C1—N3—C3 | 107.64 (10) | O11—N12—N11 | 116.95 (10) |
C6H6N12O12 | F(000) = 888 |
Mr = 438.23 | Dx = 2.035 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8628 (11) Å | Cell parameters from 2430 reflections |
b = 12.5928 (16) Å | θ = 4.5–51.2° |
c = 13.3947 (17) Å | µ = 0.20 mm−1 |
β = 106.920 (2)° | T = 298 K |
V = 1430.2 (3) Å3 | Block, colorless |
Z = 4 | 0.30 × 0.20 × 0.20 mm |
Radiation source: fine-focus sealed tube | 2174 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
Absorption correction: empirical Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | θmax = 29.7°, θmin = 2.3° |
Tmin = 0.858, Tmax = 1.000 | h = −12→11 |
9342 measured reflections | k = −16→17 |
3735 independent reflections | l = −18→15 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.0526P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.058 |
3735 reflections | Δρmax = 0.26 e Å−3 |
296 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0094 (13) |
C6H6N12O12 | V = 1430.2 (3) Å3 |
Mr = 438.23 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.8628 (11) Å | µ = 0.20 mm−1 |
b = 12.5928 (16) Å | T = 298 K |
c = 13.3947 (17) Å | 0.30 × 0.20 × 0.20 mm |
β = 106.920 (2)° |
Absorption correction: empirical Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | 3735 independent reflections |
Tmin = 0.858, Tmax = 1.000 | 2174 reflections with I > 2σ(I) |
9342 measured reflections | Rint = 0.050 |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.116 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.26 e Å−3 |
3735 reflections | Δρmin = −0.25 e Å−3 |
296 parameters |
Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS. No formal measure of the extent of decay is printed out by this program. The final unit cell is obtained from the refinement of the XYZ weighted centroids of reflections above 15 σ(I). |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.4311 (3) | −0.23426 (18) | 0.21368 (18) | 0.0226 (5) | |
H1 | 0.389 (3) | −0.297 (2) | 0.1834 (18) | 0.029 (7)* | |
C3 | 0.6578 (3) | −0.11856 (18) | 0.22188 (17) | 0.0235 (5) | |
H3 | 0.746 (3) | −0.1124 (17) | 0.1963 (17) | 0.024 (6)* | |
C5 | 0.5852 (3) | −0.06188 (18) | 0.37374 (18) | 0.0229 (5) | |
H5 | 0.628 (3) | −0.0344 (17) | 0.4418 (18) | 0.023 (6)* | |
C7 | 0.5456 (3) | −0.01946 (18) | 0.19291 (17) | 0.0231 (5) | |
H7 | 0.582 (3) | 0.0302 (17) | 0.1539 (16) | 0.021 (6)* | |
C9 | 0.3175 (3) | −0.13616 (18) | 0.18368 (18) | 0.0235 (5) | |
H9 | 0.221 (3) | −0.1552 (18) | 0.1344 (17) | 0.024 (6)* | |
C11 | 0.4378 (3) | −0.13681 (17) | 0.36616 (18) | 0.0220 (5) | |
H11 | 0.420 (3) | −0.1383 (18) | 0.4300 (18) | 0.030 (7)* | |
N1 | 0.6462 (3) | −0.29780 (17) | 0.14733 (16) | 0.0334 (5) | |
N2 | 0.5678 (2) | −0.21221 (14) | 0.17942 (14) | 0.0242 (5) | |
N3 | 0.7865 (2) | −0.19742 (16) | 0.39606 (16) | 0.0301 (5) | |
N4 | 0.7066 (2) | −0.11325 (14) | 0.33720 (14) | 0.0238 (4) | |
N5 | 0.4523 (2) | 0.10326 (15) | 0.30473 (16) | 0.0265 (5) | |
N6 | 0.5518 (2) | 0.02215 (14) | 0.29654 (13) | 0.0221 (4) | |
N7 | 0.3128 (3) | −0.01271 (17) | 0.03894 (15) | 0.0308 (5) | |
N8 | 0.3894 (2) | −0.05447 (15) | 0.13678 (14) | 0.0260 (5) | |
N9 | 0.1521 (3) | −0.10523 (16) | 0.30145 (18) | 0.0322 (5) | |
N10 | 0.3028 (2) | −0.09681 (15) | 0.28366 (14) | 0.0233 (4) | |
N11 | 0.4182 (2) | −0.33030 (15) | 0.37243 (17) | 0.0299 (5) | |
N12 | 0.4725 (2) | −0.24022 (13) | 0.32829 (14) | 0.0222 (4) | |
O1 | 0.5890 (3) | −0.38519 (15) | 0.14840 (18) | 0.0583 (6) | |
O2 | 0.7598 (2) | −0.27482 (15) | 0.11910 (14) | 0.0425 (5) | |
O3 | 0.8488 (2) | −0.26021 (14) | 0.35129 (15) | 0.0425 (5) | |
O4 | 0.7889 (2) | −0.19887 (15) | 0.48707 (14) | 0.0452 (5) | |
O5 | 0.4238 (2) | 0.11200 (13) | 0.38849 (13) | 0.0364 (4) | |
O6 | 0.4058 (2) | 0.16054 (12) | 0.22897 (13) | 0.0333 (4) | |
O7 | 0.1913 (3) | −0.05533 (17) | −0.00819 (14) | 0.0549 (6) | |
O8 | 0.3753 (2) | 0.06240 (14) | 0.00985 (13) | 0.0380 (5) | |
O9 | 0.0395 (2) | −0.11530 (14) | 0.22564 (15) | 0.0407 (5) | |
O10 | 0.1525 (2) | −0.09586 (16) | 0.39190 (16) | 0.0529 (6) | |
O11 | 0.4019 (2) | −0.31862 (14) | 0.45821 (15) | 0.0457 (5) | |
O12 | 0.4020 (2) | −0.41139 (13) | 0.32126 (14) | 0.0389 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0235 (13) | 0.0202 (12) | 0.0234 (13) | −0.0010 (10) | 0.0058 (10) | −0.0026 (10) |
C3 | 0.0213 (13) | 0.0297 (13) | 0.0199 (12) | 0.0009 (11) | 0.0067 (10) | 0.0016 (10) |
C5 | 0.0251 (13) | 0.0238 (12) | 0.0173 (12) | −0.0005 (10) | 0.0025 (10) | −0.0012 (10) |
C7 | 0.0226 (13) | 0.0269 (12) | 0.0204 (12) | −0.0018 (11) | 0.0073 (10) | 0.0026 (10) |
C9 | 0.0202 (13) | 0.0250 (12) | 0.0226 (12) | −0.0009 (10) | 0.0020 (10) | −0.0012 (10) |
C11 | 0.0247 (14) | 0.0213 (11) | 0.0194 (12) | 0.0009 (10) | 0.0056 (10) | −0.0006 (9) |
N1 | 0.0348 (13) | 0.0339 (13) | 0.0313 (12) | 0.0101 (11) | 0.0093 (10) | −0.0023 (9) |
N2 | 0.0239 (12) | 0.0253 (10) | 0.0238 (11) | 0.0011 (9) | 0.0075 (9) | −0.0066 (8) |
N3 | 0.0245 (12) | 0.0336 (12) | 0.0282 (12) | 0.0043 (10) | 0.0016 (9) | 0.0034 (9) |
N4 | 0.0200 (10) | 0.0276 (10) | 0.0216 (10) | 0.0027 (9) | 0.0024 (8) | 0.0017 (8) |
N5 | 0.0227 (11) | 0.0238 (10) | 0.0323 (12) | −0.0051 (9) | 0.0069 (9) | −0.0028 (9) |
N6 | 0.0244 (11) | 0.0202 (10) | 0.0214 (10) | 0.0004 (9) | 0.0060 (8) | −0.0004 (8) |
N7 | 0.0341 (13) | 0.0345 (12) | 0.0215 (11) | 0.0109 (11) | 0.0044 (10) | −0.0002 (9) |
N8 | 0.0233 (12) | 0.0313 (11) | 0.0191 (10) | 0.0005 (9) | −0.0005 (8) | 0.0064 (8) |
N9 | 0.0277 (13) | 0.0268 (11) | 0.0461 (14) | 0.0025 (10) | 0.0169 (11) | 0.0069 (10) |
N10 | 0.0183 (11) | 0.0270 (10) | 0.0261 (11) | 0.0001 (8) | 0.0086 (8) | −0.0006 (8) |
N11 | 0.0255 (12) | 0.0238 (11) | 0.0394 (13) | 0.0002 (9) | 0.0079 (10) | 0.0065 (10) |
N12 | 0.0267 (11) | 0.0183 (9) | 0.0216 (10) | −0.0008 (8) | 0.0071 (8) | −0.0002 (7) |
O1 | 0.0538 (15) | 0.0287 (11) | 0.0991 (18) | 0.0040 (10) | 0.0331 (13) | −0.0134 (11) |
O2 | 0.0406 (12) | 0.0514 (12) | 0.0433 (11) | 0.0144 (10) | 0.0244 (10) | 0.0020 (9) |
O3 | 0.0395 (12) | 0.0467 (11) | 0.0433 (11) | 0.0198 (10) | 0.0153 (9) | 0.0084 (9) |
O4 | 0.0521 (13) | 0.0574 (12) | 0.0206 (10) | 0.0130 (10) | 0.0021 (8) | 0.0093 (9) |
O5 | 0.0429 (12) | 0.0379 (10) | 0.0316 (10) | 0.0030 (9) | 0.0161 (8) | −0.0081 (8) |
O6 | 0.0345 (11) | 0.0251 (9) | 0.0392 (10) | 0.0037 (8) | 0.0089 (8) | 0.0079 (8) |
O7 | 0.0479 (13) | 0.0612 (14) | 0.0373 (11) | −0.0059 (11) | −0.0165 (10) | 0.0009 (10) |
O8 | 0.0431 (12) | 0.0428 (11) | 0.0310 (10) | 0.0096 (9) | 0.0153 (9) | 0.0150 (8) |
O9 | 0.0201 (10) | 0.0395 (10) | 0.0595 (13) | −0.0018 (9) | 0.0068 (9) | 0.0067 (9) |
O10 | 0.0460 (13) | 0.0737 (15) | 0.0507 (13) | 0.0092 (11) | 0.0324 (10) | 0.0042 (11) |
O11 | 0.0643 (15) | 0.0405 (11) | 0.0418 (12) | −0.0018 (10) | 0.0306 (10) | 0.0095 (9) |
O12 | 0.0412 (12) | 0.0206 (9) | 0.0520 (12) | −0.0046 (8) | 0.0092 (9) | −0.0026 (8) |
C1—N2 | 1.442 (3) | C11—H11 | 0.91 (2) |
C1—N12 | 1.473 (3) | N1—O2 | 1.210 (3) |
C1—C9 | 1.571 (3) | N1—O1 | 1.213 (3) |
C1—H1 | 0.92 (2) | N1—N2 | 1.415 (3) |
C3—N2 | 1.445 (3) | N3—O4 | 1.213 (2) |
C3—N4 | 1.480 (3) | N3—O3 | 1.218 (3) |
C3—C7 | 1.573 (3) | N3—N4 | 1.386 (3) |
C3—H3 | 0.94 (2) | N5—O6 | 1.215 (2) |
C5—N6 | 1.449 (3) | N5—O5 | 1.225 (2) |
C5—N4 | 1.457 (3) | N5—N6 | 1.374 (3) |
C5—C11 | 1.590 (3) | N7—O7 | 1.204 (3) |
C5—H5 | 0.95 (2) | N7—O8 | 1.216 (3) |
C7—N8 | 1.439 (3) | N7—N8 | 1.392 (3) |
C7—N6 | 1.470 (3) | N9—O9 | 1.205 (3) |
C7—H7 | 0.93 (2) | N9—O10 | 1.216 (3) |
C9—N8 | 1.446 (3) | N9—N10 | 1.427 (3) |
C9—N10 | 1.469 (3) | N11—O11 | 1.208 (3) |
C9—H9 | 0.95 (2) | N11—O12 | 1.215 (2) |
C11—N10 | 1.462 (3) | N11—N12 | 1.426 (3) |
C11—N12 | 1.462 (3) | ||
N2—C1—N12 | 111.38 (19) | O2—N1—O1 | 127.5 (2) |
N2—C1—C9 | 107.63 (18) | O2—N1—N2 | 116.1 (2) |
N12—C1—C9 | 104.66 (17) | O1—N1—N2 | 116.4 (2) |
N2—C1—H1 | 107.1 (15) | N1—N2—C1 | 118.82 (19) |
N12—C1—H1 | 111.2 (14) | N1—N2—C3 | 118.54 (19) |
C9—C1—H1 | 114.9 (15) | C1—N2—C3 | 116.80 (18) |
N2—C3—N4 | 114.07 (18) | O4—N3—O3 | 127.4 (2) |
N2—C3—C7 | 108.27 (18) | O4—N3—N4 | 116.1 (2) |
N4—C3—C7 | 101.14 (17) | O3—N3—N4 | 116.51 (19) |
N2—C3—H3 | 110.2 (13) | N3—N4—C5 | 116.98 (17) |
N4—C3—H3 | 110.9 (14) | N3—N4—C3 | 120.32 (17) |
C7—C3—H3 | 112.1 (13) | C5—N4—C3 | 110.55 (18) |
N6—C5—N4 | 95.85 (16) | O6—N5—O5 | 127.0 (2) |
N6—C5—C11 | 113.24 (19) | O6—N5—N6 | 116.36 (19) |
N4—C5—C11 | 112.85 (18) | O5—N5—N6 | 116.62 (19) |
N6—C5—H5 | 111.3 (13) | N5—N6—C5 | 119.24 (18) |
N4—C5—H5 | 110.9 (14) | N5—N6—C7 | 119.45 (18) |
C11—C5—H5 | 111.8 (14) | C5—N6—C7 | 110.95 (17) |
N8—C7—N6 | 111.65 (19) | O7—N7—O8 | 126.9 (2) |
N8—C7—C3 | 109.22 (18) | O7—N7—N8 | 116.2 (2) |
N6—C7—C3 | 101.70 (17) | O8—N7—N8 | 116.9 (2) |
N8—C7—H7 | 110.4 (14) | N7—N8—C7 | 120.53 (19) |
N6—C7—H7 | 111.5 (13) | N7—N8—C9 | 121.45 (19) |
C3—C7—H7 | 112.1 (14) | C7—N8—C9 | 118.00 (18) |
N8—C9—N10 | 108.86 (18) | O9—N9—O10 | 127.7 (2) |
N8—C9—C1 | 109.86 (19) | O9—N9—N10 | 116.9 (2) |
N10—C9—C1 | 104.62 (17) | O10—N9—N10 | 115.3 (2) |
N8—C9—H9 | 107.4 (14) | N9—N10—C11 | 116.61 (18) |
N10—C9—H9 | 114.9 (14) | N9—N10—C9 | 117.57 (19) |
C1—C9—H9 | 111.1 (14) | C11—N10—C9 | 107.63 (17) |
N10—C11—N12 | 104.66 (18) | O11—N11—O12 | 127.7 (2) |
N10—C11—C5 | 108.67 (18) | O11—N11—N12 | 116.46 (19) |
N12—C11—C5 | 107.39 (18) | O12—N11—N12 | 115.7 (2) |
N10—C11—H11 | 112.8 (15) | N11—N12—C11 | 115.75 (18) |
N12—C11—H11 | 114.7 (15) | N11—N12—C1 | 117.46 (18) |
C5—C11—H11 | 108.3 (15) | C11—N12—C1 | 107.61 (17) |
C6H6N12O12 | F(000) = 888 |
Mr = 438.23 | Dx = 2.050 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8408 (9) Å | Cell parameters from 2341 reflections |
b = 12.5622 (12) Å | θ = 4.6–51.3° |
c = 13.3577 (13) Å | µ = 0.20 mm−1 |
β = 106.820 (2)° | T = 250 K |
V = 1420.0 (2) Å3 | Block, colorless |
Z = 4 | 0.30 × 0.20 × 0.20 mm |
Radiation source: fine-focus sealed tube | 2338 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
Absorption correction: empirical Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | θmax = 29.7°, θmin = 2.3° |
Tmin = 0.872, Tmax = 1.000 | h = −10→12 |
9290 measured reflections | k = −16→17 |
3712 independent reflections | l = −15→18 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.0526P)2 + 0.0546P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.038 |
3712 reflections | Δρmax = 0.35 e Å−3 |
296 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0080 (13) |
C6H6N12O12 | V = 1420.0 (2) Å3 |
Mr = 438.23 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.8408 (9) Å | µ = 0.20 mm−1 |
b = 12.5622 (12) Å | T = 250 K |
c = 13.3577 (13) Å | 0.30 × 0.20 × 0.20 mm |
β = 106.820 (2)° |
Absorption correction: empirical Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | 3712 independent reflections |
Tmin = 0.872, Tmax = 1.000 | 2338 reflections with I > 2σ(I) |
9290 measured reflections | Rint = 0.046 |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.35 e Å−3 |
3712 reflections | Δρmin = −0.27 e Å−3 |
296 parameters |
Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS. No formal measure of the extent of decay is printed out by this program. The final unit cell is obtained from the refinement of the XYZ weighted centroids of reflections above 15 σ(I). |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.4318 (3) | −0.23479 (17) | 0.21376 (16) | 0.0195 (5) | |
H1 | 0.387 (3) | −0.2951 (18) | 0.1852 (16) | 0.016 (6)* | |
C3 | 0.6590 (3) | −0.11850 (17) | 0.22197 (16) | 0.0200 (5) | |
H3 | 0.747 (3) | −0.1165 (16) | 0.1952 (17) | 0.024 (6)* | |
C5 | 0.5857 (3) | −0.06175 (17) | 0.37419 (17) | 0.0198 (5) | |
H5 | 0.628 (3) | −0.0340 (17) | 0.4418 (18) | 0.022 (6)* | |
C7 | 0.5462 (3) | −0.01940 (17) | 0.19285 (16) | 0.0199 (5) | |
H7 | 0.579 (2) | 0.0313 (15) | 0.1532 (15) | 0.009 (5)* | |
C9 | 0.3173 (3) | −0.13629 (17) | 0.18320 (17) | 0.0202 (5) | |
H9 | 0.219 (3) | −0.1546 (16) | 0.1381 (16) | 0.015 (5)* | |
C11 | 0.4380 (3) | −0.13684 (16) | 0.36628 (17) | 0.0192 (5) | |
H11 | 0.414 (2) | −0.1421 (16) | 0.4273 (16) | 0.015 (5)* | |
N1 | 0.6466 (2) | −0.29818 (15) | 0.14683 (15) | 0.0280 (5) | |
N2 | 0.5682 (2) | −0.21250 (14) | 0.17918 (13) | 0.0212 (4) | |
N3 | 0.7865 (2) | −0.19793 (15) | 0.39555 (14) | 0.0255 (4) | |
N4 | 0.7066 (2) | −0.11341 (13) | 0.33711 (13) | 0.0195 (4) | |
N5 | 0.4517 (2) | 0.10351 (13) | 0.30484 (15) | 0.0224 (4) | |
N6 | 0.5518 (2) | 0.02239 (13) | 0.29651 (13) | 0.0188 (4) | |
N7 | 0.3134 (2) | −0.01223 (15) | 0.03873 (14) | 0.0263 (4) | |
N8 | 0.3895 (2) | −0.05428 (14) | 0.13648 (13) | 0.0220 (4) | |
N9 | 0.1512 (2) | −0.10572 (15) | 0.30174 (16) | 0.0271 (5) | |
N10 | 0.3028 (2) | −0.09683 (14) | 0.28387 (13) | 0.0207 (4) | |
N11 | 0.4181 (2) | −0.33109 (14) | 0.37247 (15) | 0.0247 (4) | |
N12 | 0.4726 (2) | −0.24073 (12) | 0.32868 (13) | 0.0190 (4) | |
O1 | 0.5896 (2) | −0.38588 (13) | 0.14767 (16) | 0.0477 (5) | |
O2 | 0.7608 (2) | −0.27506 (14) | 0.11842 (13) | 0.0354 (4) | |
O3 | 0.8486 (2) | −0.26118 (13) | 0.35111 (13) | 0.0353 (4) | |
O4 | 0.7893 (2) | −0.19960 (14) | 0.48719 (12) | 0.0372 (4) | |
O5 | 0.4228 (2) | 0.11217 (12) | 0.38878 (12) | 0.0302 (4) | |
O6 | 0.4048 (2) | 0.16068 (12) | 0.22868 (12) | 0.0288 (4) | |
O7 | 0.1910 (2) | −0.05510 (15) | −0.00904 (13) | 0.0455 (5) | |
O8 | 0.3756 (2) | 0.06320 (13) | 0.00969 (12) | 0.0329 (4) | |
O9 | 0.0387 (2) | −0.11577 (13) | 0.22548 (14) | 0.0354 (4) | |
O10 | 0.1516 (2) | −0.09596 (15) | 0.39247 (14) | 0.0453 (5) | |
O11 | 0.4016 (2) | −0.31922 (13) | 0.45840 (13) | 0.0378 (5) | |
O12 | 0.4018 (2) | −0.41231 (12) | 0.32130 (13) | 0.0334 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0193 (11) | 0.0192 (11) | 0.0194 (11) | −0.0013 (9) | 0.0048 (9) | −0.0026 (9) |
C3 | 0.0187 (11) | 0.0230 (11) | 0.0193 (11) | 0.0013 (9) | 0.0072 (9) | 0.0012 (9) |
C5 | 0.0217 (12) | 0.0213 (11) | 0.0156 (11) | −0.0018 (9) | 0.0042 (9) | −0.0023 (9) |
C7 | 0.0191 (12) | 0.0225 (11) | 0.0177 (11) | −0.0027 (9) | 0.0046 (9) | 0.0013 (9) |
C9 | 0.0138 (11) | 0.0235 (11) | 0.0219 (11) | −0.0003 (9) | 0.0029 (9) | −0.0013 (9) |
C11 | 0.0226 (12) | 0.0204 (11) | 0.0158 (11) | 0.0003 (9) | 0.0074 (9) | 0.0007 (8) |
N1 | 0.0276 (11) | 0.0293 (11) | 0.0277 (11) | 0.0094 (9) | 0.0088 (9) | −0.0020 (8) |
N2 | 0.0207 (10) | 0.0234 (9) | 0.0203 (10) | 0.0020 (8) | 0.0073 (8) | −0.0040 (7) |
N3 | 0.0218 (10) | 0.0298 (11) | 0.0233 (11) | 0.0033 (9) | 0.0040 (8) | 0.0025 (8) |
N4 | 0.0171 (9) | 0.0210 (9) | 0.0190 (9) | 0.0019 (8) | 0.0030 (7) | 0.0023 (7) |
N5 | 0.0209 (10) | 0.0177 (9) | 0.0277 (11) | −0.0036 (8) | 0.0059 (8) | −0.0033 (8) |
N6 | 0.0197 (10) | 0.0182 (9) | 0.0186 (9) | 0.0000 (8) | 0.0056 (7) | 0.0005 (7) |
N7 | 0.0267 (11) | 0.0300 (11) | 0.0203 (10) | 0.0102 (9) | 0.0041 (9) | 0.0001 (8) |
N8 | 0.0211 (10) | 0.0257 (10) | 0.0167 (9) | −0.0001 (8) | 0.0016 (8) | 0.0053 (8) |
N9 | 0.0228 (11) | 0.0219 (10) | 0.0407 (13) | 0.0030 (8) | 0.0155 (10) | 0.0041 (8) |
N10 | 0.0172 (9) | 0.0236 (9) | 0.0223 (10) | 0.0008 (8) | 0.0071 (8) | 0.0005 (7) |
N11 | 0.0215 (10) | 0.0222 (10) | 0.0298 (11) | −0.0002 (8) | 0.0068 (8) | 0.0049 (8) |
N12 | 0.0215 (10) | 0.0151 (8) | 0.0214 (10) | −0.0006 (8) | 0.0076 (8) | 0.0011 (7) |
O1 | 0.0453 (12) | 0.0235 (10) | 0.0800 (15) | 0.0008 (9) | 0.0274 (11) | −0.0108 (9) |
O2 | 0.0333 (10) | 0.0417 (10) | 0.0373 (10) | 0.0109 (9) | 0.0199 (8) | 0.0024 (8) |
O3 | 0.0336 (10) | 0.0376 (10) | 0.0362 (10) | 0.0152 (8) | 0.0127 (8) | 0.0064 (8) |
O4 | 0.0445 (11) | 0.0449 (10) | 0.0189 (9) | 0.0112 (9) | 0.0039 (7) | 0.0072 (8) |
O5 | 0.0351 (10) | 0.0336 (9) | 0.0254 (9) | 0.0016 (8) | 0.0142 (7) | −0.0066 (7) |
O6 | 0.0288 (10) | 0.0230 (8) | 0.0337 (9) | 0.0019 (7) | 0.0076 (7) | 0.0076 (7) |
O7 | 0.0394 (11) | 0.0490 (12) | 0.0332 (10) | −0.0038 (10) | −0.0130 (9) | 0.0021 (9) |
O8 | 0.0392 (11) | 0.0359 (10) | 0.0259 (9) | 0.0073 (8) | 0.0132 (8) | 0.0127 (7) |
O9 | 0.0187 (9) | 0.0339 (9) | 0.0514 (11) | −0.0021 (8) | 0.0066 (8) | 0.0061 (8) |
O10 | 0.0413 (12) | 0.0621 (13) | 0.0423 (11) | 0.0074 (10) | 0.0274 (9) | 0.0030 (9) |
O11 | 0.0517 (12) | 0.0337 (10) | 0.0352 (10) | −0.0019 (9) | 0.0241 (9) | 0.0065 (8) |
O12 | 0.0364 (10) | 0.0191 (8) | 0.0415 (10) | −0.0024 (7) | 0.0065 (8) | −0.0008 (7) |
C1—N2 | 1.438 (3) | C11—H11 | 0.90 (2) |
C1—N12 | 1.474 (3) | N1—O2 | 1.212 (3) |
C1—C9 | 1.576 (3) | N1—O1 | 1.213 (2) |
C1—H1 | 0.89 (2) | N1—N2 | 1.414 (2) |
C3—N2 | 1.449 (3) | N3—O3 | 1.214 (2) |
C3—N4 | 1.474 (3) | N3—O4 | 1.217 (2) |
C3—C7 | 1.572 (3) | N3—N4 | 1.385 (2) |
C3—H3 | 0.94 (2) | N5—O6 | 1.216 (2) |
C5—N6 | 1.450 (3) | N5—O5 | 1.225 (2) |
C5—N4 | 1.454 (3) | N5—N6 | 1.375 (2) |
C5—C11 | 1.589 (3) | N7—O7 | 1.212 (3) |
C5—H5 | 0.94 (2) | N7—O8 | 1.214 (2) |
C7—N8 | 1.441 (3) | N7—N8 | 1.389 (2) |
C7—N6 | 1.468 (3) | N9—O9 | 1.207 (3) |
C7—H7 | 0.93 (2) | N9—O10 | 1.217 (2) |
C9—N8 | 1.445 (3) | N9—N10 | 1.433 (3) |
C9—N10 | 1.473 (3) | N11—O11 | 1.208 (2) |
C9—H9 | 0.93 (2) | N11—O12 | 1.213 (2) |
C11—N10 | 1.460 (3) | N11—N12 | 1.423 (2) |
C11—N12 | 1.462 (3) | ||
N2—C1—N12 | 111.69 (18) | O2—N1—O1 | 127.3 (2) |
N2—C1—C9 | 107.42 (17) | O2—N1—N2 | 116.09 (19) |
N12—C1—C9 | 104.75 (16) | O1—N1—N2 | 116.54 (19) |
N2—C1—H1 | 110.1 (14) | N1—N2—C1 | 118.74 (17) |
N12—C1—H1 | 110.4 (13) | N1—N2—C3 | 118.46 (17) |
C9—C1—H1 | 112.4 (14) | C1—N2—C3 | 116.87 (16) |
N2—C3—N4 | 113.92 (17) | O3—N3—O4 | 126.88 (19) |
N2—C3—C7 | 107.99 (17) | O3—N3—N4 | 117.10 (18) |
N4—C3—C7 | 101.13 (16) | O4—N3—N4 | 116.00 (18) |
N2—C3—H3 | 107.1 (13) | N3—N4—C5 | 117.12 (16) |
N4—C3—H3 | 112.1 (14) | N3—N4—C3 | 120.01 (16) |
C7—C3—H3 | 114.6 (13) | C5—N4—C3 | 111.02 (16) |
N6—C5—N4 | 95.84 (15) | O6—N5—O5 | 127.05 (19) |
N6—C5—C11 | 112.90 (18) | O6—N5—N6 | 116.22 (17) |
N4—C5—C11 | 112.53 (17) | O5—N5—N6 | 116.70 (17) |
N6—C5—H5 | 111.1 (13) | N5—N6—C5 | 119.14 (16) |
N4—C5—H5 | 111.3 (14) | N5—N6—C7 | 119.64 (17) |
C11—C5—H5 | 112.2 (13) | C5—N6—C7 | 110.96 (16) |
N8—C7—N6 | 111.48 (17) | O7—N7—O8 | 126.6 (2) |
N8—C7—C3 | 109.49 (17) | O7—N7—N8 | 116.22 (19) |
N6—C7—C3 | 101.77 (16) | O8—N7—N8 | 117.15 (19) |
N8—C7—H7 | 108.7 (13) | N7—N8—C7 | 120.44 (17) |
N6—C7—H7 | 111.3 (12) | N7—N8—C9 | 121.55 (18) |
C3—C7—H7 | 114.1 (12) | C7—N8—C9 | 117.98 (17) |
N8—C9—N10 | 108.67 (17) | O9—N9—O10 | 128.0 (2) |
N8—C9—C1 | 109.94 (17) | O9—N9—N10 | 116.74 (18) |
N10—C9—C1 | 104.29 (16) | O10—N9—N10 | 115.10 (19) |
N8—C9—H9 | 110.0 (13) | N9—N10—C11 | 116.68 (16) |
N10—C9—H9 | 111.3 (13) | N9—N10—C9 | 117.31 (17) |
C1—C9—H9 | 112.5 (13) | C11—N10—C9 | 107.69 (16) |
N10—C11—N12 | 104.79 (17) | O11—N11—O12 | 127.73 (19) |
N10—C11—C5 | 108.86 (17) | O11—N11—N12 | 116.14 (17) |
N12—C11—C5 | 107.65 (17) | O12—N11—N12 | 116.01 (18) |
N10—C11—H11 | 110.7 (14) | N11—N12—C11 | 116.20 (17) |
N12—C11—H11 | 111.8 (13) | N11—N12—C1 | 117.31 (17) |
C5—C11—H11 | 112.6 (14) | C11—N12—C1 | 107.47 (16) |
C6H6N12O12 | F(000) = 888 |
Mr = 438.23 | Dx = 2.061 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8212 (10) Å | Cell parameters from 2367 reflections |
b = 12.5368 (14) Å | θ = 4.6–51.4° |
c = 13.3330 (15) Å | µ = 0.20 mm−1 |
β = 106.740 (2)° | T = 200 K |
V = 1412.0 (3) Å3 | Block, colorless |
Z = 4 | 0.30 × 0.20 × 0.20 mm |
Radiation source: fine-focus sealed tube | 2355 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
Absorption correction: empirical Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | θmax = 29.8°, θmin = 2.3° |
Tmin = 0.878, Tmax = 1.000 | h = −10→12 |
9186 measured reflections | k = −16→17 |
3681 independent reflections | l = −15→18 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.053P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max = 0.039 |
3681 reflections | Δρmax = 0.33 e Å−3 |
296 parameters | Δρmin = −0.32 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0084 (12) |
C6H6N12O12 | V = 1412.0 (3) Å3 |
Mr = 438.23 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.8212 (10) Å | µ = 0.20 mm−1 |
b = 12.5368 (14) Å | T = 200 K |
c = 13.3330 (15) Å | 0.30 × 0.20 × 0.20 mm |
β = 106.740 (2)° |
Absorption correction: empirical Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | 3681 independent reflections |
Tmin = 0.878, Tmax = 1.000 | 2355 reflections with I > 2σ(I) |
9186 measured reflections | Rint = 0.044 |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | Δρmax = 0.33 e Å−3 |
3681 reflections | Δρmin = −0.32 e Å−3 |
296 parameters |
Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS. No formal measure of the extent of decay is printed out by this program. The final unit cell is obtained from the refinement of the XYZ weighted centroids of reflections above 15 σ(I). |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.4318 (2) | −0.23488 (16) | 0.21342 (15) | 0.0159 (4) | |
H1 | 0.385 (2) | −0.2953 (17) | 0.1843 (16) | 0.018 (5)* | |
C3 | 0.6595 (2) | −0.11861 (15) | 0.22155 (15) | 0.0169 (4) | |
H3 | 0.752 (3) | −0.1157 (14) | 0.1953 (15) | 0.016 (5)* | |
C5 | 0.5861 (2) | −0.06165 (15) | 0.37452 (15) | 0.0163 (4) | |
H5 | 0.627 (3) | −0.0362 (16) | 0.4427 (17) | 0.018 (5)* | |
C7 | 0.5464 (2) | −0.01934 (15) | 0.19260 (15) | 0.0161 (4) | |
H7 | 0.581 (2) | 0.0306 (16) | 0.1512 (15) | 0.018 (5)* | |
C9 | 0.3170 (2) | −0.13641 (16) | 0.18327 (15) | 0.0173 (4) | |
H9 | 0.218 (3) | −0.1539 (15) | 0.1347 (15) | 0.016 (5)* | |
C11 | 0.4379 (2) | −0.13712 (15) | 0.36653 (15) | 0.0158 (4) | |
H11 | 0.419 (2) | −0.1406 (15) | 0.4273 (15) | 0.012 (5)* | |
N1 | 0.6470 (2) | −0.29860 (14) | 0.14643 (13) | 0.0229 (4) | |
N2 | 0.56852 (19) | −0.21268 (12) | 0.17872 (12) | 0.0175 (4) | |
N3 | 0.7870 (2) | −0.19838 (13) | 0.39572 (13) | 0.0212 (4) | |
N4 | 0.70748 (19) | −0.11347 (12) | 0.33729 (12) | 0.0169 (4) | |
N5 | 0.4512 (2) | 0.10388 (12) | 0.30481 (13) | 0.0189 (4) | |
N6 | 0.55232 (19) | 0.02268 (12) | 0.29673 (12) | 0.0154 (3) | |
N7 | 0.3129 (2) | −0.01225 (14) | 0.03851 (12) | 0.0216 (4) | |
N8 | 0.38965 (19) | −0.05413 (13) | 0.13632 (12) | 0.0185 (4) | |
N9 | 0.1509 (2) | −0.10619 (13) | 0.30209 (14) | 0.0224 (4) | |
N10 | 0.30230 (19) | −0.09672 (13) | 0.28369 (12) | 0.0171 (4) | |
N11 | 0.4183 (2) | −0.33170 (13) | 0.37268 (14) | 0.0209 (4) | |
N12 | 0.4729 (2) | −0.24091 (12) | 0.32864 (12) | 0.0161 (4) | |
O1 | 0.5897 (2) | −0.38654 (12) | 0.14692 (14) | 0.0393 (4) | |
O2 | 0.76165 (19) | −0.27533 (12) | 0.11781 (12) | 0.0285 (4) | |
O3 | 0.84835 (18) | −0.26200 (12) | 0.35037 (12) | 0.0287 (4) | |
O4 | 0.78985 (19) | −0.20028 (12) | 0.48761 (11) | 0.0303 (4) | |
O5 | 0.42199 (18) | 0.11248 (11) | 0.38889 (11) | 0.0249 (3) | |
O6 | 0.40408 (17) | 0.16102 (11) | 0.22832 (11) | 0.0236 (3) | |
O7 | 0.1908 (2) | −0.05507 (13) | −0.00986 (12) | 0.0375 (4) | |
O8 | 0.37611 (18) | 0.06385 (11) | 0.00934 (11) | 0.0261 (4) | |
O9 | 0.03782 (17) | −0.11619 (11) | 0.22545 (12) | 0.0286 (4) | |
O10 | 0.1514 (2) | −0.09648 (13) | 0.39299 (13) | 0.0368 (4) | |
O11 | 0.4016 (2) | −0.32000 (11) | 0.45896 (12) | 0.0311 (4) | |
O12 | 0.40199 (18) | −0.41308 (11) | 0.32130 (11) | 0.0269 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0154 (10) | 0.0156 (10) | 0.0163 (10) | −0.0008 (8) | 0.0038 (8) | −0.0012 (8) |
C3 | 0.0163 (10) | 0.0194 (10) | 0.0155 (10) | −0.0013 (8) | 0.0053 (8) | 0.0006 (8) |
C5 | 0.0175 (10) | 0.0180 (10) | 0.0127 (10) | 0.0003 (8) | 0.0031 (8) | −0.0005 (8) |
C7 | 0.0148 (10) | 0.0192 (10) | 0.0145 (10) | −0.0015 (8) | 0.0045 (8) | 0.0012 (8) |
C9 | 0.0148 (10) | 0.0186 (10) | 0.0172 (10) | −0.0010 (8) | 0.0027 (8) | −0.0003 (8) |
C11 | 0.0158 (10) | 0.0190 (10) | 0.0128 (10) | 0.0015 (8) | 0.0042 (8) | 0.0004 (8) |
N1 | 0.0225 (10) | 0.0233 (10) | 0.0231 (10) | 0.0069 (8) | 0.0070 (8) | −0.0023 (7) |
N2 | 0.0171 (9) | 0.0177 (8) | 0.0190 (9) | 0.0003 (7) | 0.0071 (7) | −0.0042 (7) |
N3 | 0.0171 (9) | 0.0249 (9) | 0.0196 (9) | 0.0020 (8) | 0.0021 (7) | 0.0015 (7) |
N4 | 0.0148 (8) | 0.0191 (8) | 0.0156 (8) | 0.0022 (7) | 0.0025 (7) | 0.0013 (7) |
N5 | 0.0166 (9) | 0.0165 (8) | 0.0233 (9) | −0.0031 (7) | 0.0051 (7) | −0.0025 (7) |
N6 | 0.0173 (9) | 0.0132 (8) | 0.0159 (8) | 0.0005 (7) | 0.0051 (7) | −0.0004 (6) |
N7 | 0.0230 (10) | 0.0254 (9) | 0.0150 (9) | 0.0076 (8) | 0.0034 (7) | 0.0003 (7) |
N8 | 0.0162 (9) | 0.0226 (9) | 0.0147 (8) | −0.0013 (7) | 0.0012 (7) | 0.0033 (7) |
N9 | 0.0211 (10) | 0.0174 (9) | 0.0321 (11) | 0.0019 (7) | 0.0132 (8) | 0.0037 (7) |
N10 | 0.0137 (8) | 0.0200 (8) | 0.0185 (9) | 0.0014 (7) | 0.0061 (7) | 0.0005 (7) |
N11 | 0.0173 (9) | 0.0183 (9) | 0.0269 (10) | −0.0001 (7) | 0.0061 (8) | 0.0045 (7) |
N12 | 0.0184 (9) | 0.0134 (8) | 0.0171 (8) | −0.0014 (7) | 0.0064 (7) | 0.0003 (6) |
O1 | 0.0381 (10) | 0.0197 (8) | 0.0654 (12) | 0.0008 (8) | 0.0234 (9) | −0.0088 (8) |
O2 | 0.0267 (9) | 0.0344 (9) | 0.0293 (8) | 0.0074 (7) | 0.0159 (7) | 0.0022 (7) |
O3 | 0.0254 (8) | 0.0317 (8) | 0.0307 (9) | 0.0122 (7) | 0.0109 (7) | 0.0049 (7) |
O4 | 0.0357 (10) | 0.0374 (9) | 0.0151 (8) | 0.0073 (8) | 0.0031 (6) | 0.0063 (7) |
O5 | 0.0285 (9) | 0.0279 (8) | 0.0214 (8) | 0.0005 (7) | 0.0120 (6) | −0.0066 (6) |
O6 | 0.0216 (8) | 0.0201 (7) | 0.0286 (8) | 0.0020 (6) | 0.0065 (6) | 0.0064 (6) |
O7 | 0.0333 (10) | 0.0415 (10) | 0.0263 (9) | −0.0036 (8) | −0.0093 (7) | −0.0003 (7) |
O8 | 0.0294 (9) | 0.0294 (8) | 0.0215 (8) | 0.0057 (7) | 0.0106 (7) | 0.0095 (6) |
O9 | 0.0149 (8) | 0.0271 (8) | 0.0419 (9) | −0.0017 (7) | 0.0053 (7) | 0.0065 (7) |
O10 | 0.0320 (10) | 0.0520 (11) | 0.0339 (10) | 0.0082 (8) | 0.0215 (8) | 0.0036 (8) |
O11 | 0.0424 (11) | 0.0284 (8) | 0.0284 (9) | −0.0017 (7) | 0.0196 (8) | 0.0056 (7) |
O12 | 0.0281 (9) | 0.0160 (7) | 0.0342 (9) | −0.0029 (6) | 0.0053 (7) | −0.0022 (6) |
C1—N2 | 1.438 (2) | C11—H11 | 0.876 (19) |
C1—N12 | 1.475 (2) | N1—O1 | 1.214 (2) |
C1—C9 | 1.574 (3) | N1—O2 | 1.215 (2) |
C1—H1 | 0.90 (2) | N1—N2 | 1.413 (2) |
C3—N2 | 1.448 (2) | N3—O3 | 1.218 (2) |
C3—N4 | 1.479 (2) | N3—O4 | 1.218 (2) |
C3—C7 | 1.572 (3) | N3—N4 | 1.385 (2) |
C3—H3 | 0.97 (2) | N5—O6 | 1.217 (2) |
C5—N6 | 1.451 (2) | N5—O5 | 1.225 (2) |
C5—N4 | 1.456 (2) | N5—N6 | 1.378 (2) |
C5—C11 | 1.592 (3) | N7—O7 | 1.209 (2) |
C5—H5 | 0.93 (2) | N7—O8 | 1.224 (2) |
C7—N8 | 1.438 (2) | N7—N8 | 1.388 (2) |
C7—N6 | 1.472 (2) | N9—O9 | 1.211 (2) |
C7—H7 | 0.94 (2) | N9—O10 | 1.217 (2) |
C9—N8 | 1.448 (2) | N9—N10 | 1.431 (2) |
C9—N10 | 1.469 (2) | N11—O11 | 1.210 (2) |
C9—H9 | 0.95 (2) | N11—O12 | 1.214 (2) |
C11—N12 | 1.461 (2) | N11—N12 | 1.427 (2) |
C11—N10 | 1.465 (2) | ||
N2—C1—N12 | 111.57 (16) | O1—N1—O2 | 127.28 (17) |
N2—C1—C9 | 107.67 (15) | O1—N1—N2 | 116.70 (17) |
N12—C1—C9 | 104.67 (15) | O2—N1—N2 | 115.97 (16) |
N2—C1—H1 | 110.3 (13) | N1—N2—C1 | 118.73 (15) |
N12—C1—H1 | 110.6 (13) | N1—N2—C3 | 118.43 (16) |
C9—C1—H1 | 111.8 (13) | C1—N2—C3 | 116.87 (15) |
N2—C3—N4 | 113.97 (15) | O3—N3—O4 | 127.08 (17) |
N2—C3—C7 | 107.90 (15) | O3—N3—N4 | 116.72 (16) |
N4—C3—C7 | 101.07 (14) | O4—N3—N4 | 116.19 (16) |
N2—C3—H3 | 108.3 (11) | N3—N4—C5 | 117.00 (15) |
N4—C3—H3 | 110.8 (11) | N3—N4—C3 | 119.98 (14) |
C7—C3—H3 | 114.8 (11) | C5—N4—C3 | 110.96 (15) |
N6—C5—N4 | 95.80 (14) | O6—N5—O5 | 127.12 (17) |
N6—C5—C11 | 112.93 (16) | O6—N5—N6 | 116.23 (16) |
N4—C5—C11 | 112.47 (15) | O5—N5—N6 | 116.61 (16) |
N6—C5—H5 | 112.9 (12) | N5—N6—C5 | 119.14 (15) |
N4—C5—H5 | 111.5 (13) | N5—N6—C7 | 119.37 (15) |
C11—C5—H5 | 110.5 (13) | C5—N6—C7 | 110.97 (14) |
N8—C7—N6 | 111.59 (16) | O7—N7—O8 | 126.42 (17) |
N8—C7—C3 | 109.57 (15) | O7—N7—N8 | 116.85 (17) |
N6—C7—C3 | 101.79 (14) | O8—N7—N8 | 116.72 (17) |
N8—C7—H7 | 108.8 (13) | N7—N8—C7 | 120.75 (16) |
N6—C7—H7 | 112.7 (12) | N7—N8—C9 | 121.24 (16) |
C3—C7—H7 | 112.3 (12) | C7—N8—C9 | 117.98 (15) |
N8—C9—N10 | 108.61 (16) | O9—N9—O10 | 128.10 (19) |
N8—C9—C1 | 109.69 (16) | O9—N9—N10 | 116.51 (16) |
N10—C9—C1 | 104.61 (15) | O10—N9—N10 | 115.23 (17) |
N8—C9—H9 | 107.6 (12) | N9—N10—C11 | 116.22 (15) |
N10—C9—H9 | 113.3 (12) | N9—N10—C9 | 117.40 (15) |
C1—C9—H9 | 112.9 (12) | C11—N10—C9 | 107.63 (15) |
N12—C11—N10 | 104.78 (15) | O11—N11—O12 | 127.69 (17) |
N12—C11—C5 | 107.53 (15) | O11—N11—N12 | 116.26 (16) |
N10—C11—C5 | 108.74 (15) | O12—N11—N12 | 115.93 (16) |
N12—C11—H11 | 113.1 (13) | N11—N12—C11 | 116.00 (15) |
N10—C11—H11 | 112.4 (13) | N11—N12—C1 | 117.30 (15) |
C5—C11—H11 | 110.1 (13) | C11—N12—C1 | 107.55 (15) |
C6H6N12O12 | F(000) = 888 |
Mr = 438.23 | Dx = 2.077 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8004 (10) Å | Cell parameters from 2396 reflections |
b = 12.4992 (14) Å | θ = 4.6–55.7° |
c = 13.2985 (15) Å | µ = 0.20 mm−1 |
β = 106.622 (2)° | T = 150 K |
V = 1401.7 (3) Å3 | Block, colorless |
Z = 4 | 0.30 × 0.20 × 0.20 mm |
Radiation source: fine-focus sealed tube | 2398 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
Absorption correction: empirical Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | θmax = 29.6°, θmin = 2.3° |
Tmin = 0.880, Tmax = 1.000 | h = −10→12 |
9177 measured reflections | k = −16→17 |
3669 independent reflections | l = −15→18 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.0493P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max = 0.036 |
3669 reflections | Δρmax = 0.35 e Å−3 |
296 parameters | Δρmin = −0.32 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0085 (12) |
C6H6N12O12 | V = 1401.7 (3) Å3 |
Mr = 438.23 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.8004 (10) Å | µ = 0.20 mm−1 |
b = 12.4992 (14) Å | T = 150 K |
c = 13.2985 (15) Å | 0.30 × 0.20 × 0.20 mm |
β = 106.622 (2)° |
Absorption correction: empirical Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | 3669 independent reflections |
Tmin = 0.880, Tmax = 1.000 | 2398 reflections with I > 2σ(I) |
9177 measured reflections | Rint = 0.046 |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.98 | Δρmax = 0.35 e Å−3 |
3669 reflections | Δρmin = −0.32 e Å−3 |
296 parameters |
Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS. No formal measure of the extent of decay is printed out by this program. The final unit cell is obtained from the refinement of the XYZ weighted centroids of reflections above 15 σ(I). |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.4317 (2) | −0.23561 (16) | 0.21320 (15) | 0.0133 (4) | |
H1 | 0.389 (2) | −0.2981 (17) | 0.1851 (15) | 0.014 (5)* | |
C3 | 0.6597 (2) | −0.11876 (15) | 0.22120 (14) | 0.0139 (4) | |
H3 | 0.750 (2) | −0.1159 (14) | 0.1947 (15) | 0.012 (5)* | |
C5 | 0.5863 (2) | −0.06174 (15) | 0.37475 (15) | 0.0145 (4) | |
H5 | 0.629 (3) | −0.0347 (17) | 0.4449 (18) | 0.021 (6)* | |
C7 | 0.5467 (2) | −0.01899 (15) | 0.19250 (15) | 0.0137 (4) | |
H7 | 0.580 (2) | 0.0341 (16) | 0.1534 (16) | 0.017 (5)* | |
C9 | 0.3168 (2) | −0.13679 (15) | 0.18290 (15) | 0.0138 (4) | |
H9 | 0.218 (3) | −0.1537 (15) | 0.1347 (15) | 0.011 (5)* | |
C11 | 0.4380 (2) | −0.13701 (15) | 0.36692 (15) | 0.0128 (4) | |
H11 | 0.413 (3) | −0.1419 (16) | 0.4292 (16) | 0.017 (5)* | |
N1 | 0.6476 (2) | −0.29880 (13) | 0.14577 (13) | 0.0187 (4) | |
N2 | 0.56883 (19) | −0.21303 (12) | 0.17848 (12) | 0.0144 (4) | |
N3 | 0.78692 (19) | −0.19912 (13) | 0.39526 (13) | 0.0168 (4) | |
N4 | 0.70805 (19) | −0.11377 (12) | 0.33725 (12) | 0.0138 (3) | |
N5 | 0.4507 (2) | 0.10364 (12) | 0.30450 (13) | 0.0155 (4) | |
N6 | 0.55269 (19) | 0.02294 (12) | 0.29645 (12) | 0.0126 (3) | |
N7 | 0.3132 (2) | −0.01169 (13) | 0.03827 (12) | 0.0176 (4) | |
N8 | 0.38946 (19) | −0.05407 (13) | 0.13608 (12) | 0.0148 (4) | |
N9 | 0.1505 (2) | −0.10646 (13) | 0.30242 (14) | 0.0185 (4) | |
N10 | 0.30240 (19) | −0.09690 (13) | 0.28396 (12) | 0.0135 (3) | |
N11 | 0.4182 (2) | −0.33230 (13) | 0.37287 (13) | 0.0173 (4) | |
N12 | 0.4731 (2) | −0.24137 (12) | 0.32882 (12) | 0.0134 (3) | |
O1 | 0.58986 (19) | −0.38730 (11) | 0.14617 (13) | 0.0297 (4) | |
O2 | 0.76277 (18) | −0.27567 (12) | 0.11731 (11) | 0.0229 (3) | |
O3 | 0.84850 (18) | −0.26291 (11) | 0.35006 (11) | 0.0226 (3) | |
O4 | 0.79001 (18) | −0.20093 (12) | 0.48790 (11) | 0.0240 (3) | |
O5 | 0.42133 (17) | 0.11261 (11) | 0.38900 (10) | 0.0196 (3) | |
O6 | 0.40305 (17) | 0.16120 (10) | 0.22807 (11) | 0.0188 (3) | |
O7 | 0.19062 (19) | −0.05483 (12) | −0.01069 (11) | 0.0287 (4) | |
O8 | 0.37638 (18) | 0.06450 (11) | 0.00893 (11) | 0.0207 (3) | |
O9 | 0.03745 (17) | −0.11666 (11) | 0.22556 (12) | 0.0230 (3) | |
O10 | 0.15030 (19) | −0.09702 (12) | 0.39345 (12) | 0.0289 (4) | |
O11 | 0.40164 (19) | −0.32067 (11) | 0.45951 (11) | 0.0245 (4) | |
O12 | 0.40215 (17) | −0.41404 (11) | 0.32126 (11) | 0.0214 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0137 (10) | 0.0142 (10) | 0.0118 (10) | −0.0014 (8) | 0.0035 (8) | −0.0018 (8) |
C3 | 0.0145 (10) | 0.0154 (10) | 0.0117 (10) | −0.0005 (8) | 0.0033 (8) | 0.0006 (8) |
C5 | 0.0166 (10) | 0.0158 (10) | 0.0106 (10) | −0.0005 (8) | 0.0031 (8) | −0.0004 (8) |
C7 | 0.0137 (10) | 0.0155 (9) | 0.0119 (10) | −0.0020 (8) | 0.0036 (8) | 0.0001 (8) |
C9 | 0.0124 (10) | 0.0160 (9) | 0.0125 (10) | −0.0005 (8) | 0.0026 (8) | −0.0003 (8) |
C11 | 0.0128 (10) | 0.0141 (9) | 0.0118 (10) | 0.0008 (8) | 0.0038 (8) | 0.0001 (7) |
N1 | 0.0208 (9) | 0.0190 (9) | 0.0163 (9) | 0.0055 (8) | 0.0053 (7) | −0.0015 (7) |
N2 | 0.0155 (9) | 0.0146 (8) | 0.0144 (9) | −0.0007 (7) | 0.0064 (7) | −0.0038 (7) |
N3 | 0.0134 (8) | 0.0200 (9) | 0.0154 (9) | 0.0014 (7) | 0.0018 (7) | 0.0017 (7) |
N4 | 0.0126 (8) | 0.0153 (8) | 0.0133 (8) | 0.0022 (7) | 0.0034 (7) | 0.0012 (7) |
N5 | 0.0146 (8) | 0.0149 (8) | 0.0173 (9) | −0.0033 (7) | 0.0047 (7) | −0.0017 (7) |
N6 | 0.0147 (8) | 0.0104 (8) | 0.0131 (8) | 0.0012 (7) | 0.0049 (7) | −0.0003 (6) |
N7 | 0.0200 (10) | 0.0205 (9) | 0.0122 (9) | 0.0061 (8) | 0.0044 (7) | 0.0000 (7) |
N8 | 0.0139 (9) | 0.0189 (8) | 0.0098 (8) | −0.0007 (7) | 0.0004 (7) | 0.0035 (7) |
N9 | 0.0177 (9) | 0.0155 (9) | 0.0246 (10) | 0.0010 (7) | 0.0099 (8) | 0.0040 (7) |
N10 | 0.0111 (8) | 0.0175 (8) | 0.0129 (8) | 0.0015 (7) | 0.0050 (6) | 0.0016 (6) |
N11 | 0.0155 (9) | 0.0163 (8) | 0.0203 (9) | −0.0010 (7) | 0.0056 (7) | 0.0027 (7) |
N12 | 0.0166 (9) | 0.0113 (8) | 0.0134 (8) | −0.0007 (7) | 0.0062 (7) | 0.0002 (6) |
O1 | 0.0284 (9) | 0.0158 (8) | 0.0488 (10) | −0.0013 (7) | 0.0173 (8) | −0.0065 (7) |
O2 | 0.0207 (8) | 0.0287 (8) | 0.0232 (8) | 0.0055 (7) | 0.0128 (7) | 0.0013 (6) |
O3 | 0.0225 (8) | 0.0243 (8) | 0.0231 (8) | 0.0094 (7) | 0.0097 (6) | 0.0022 (6) |
O4 | 0.0289 (9) | 0.0294 (8) | 0.0120 (7) | 0.0057 (7) | 0.0033 (6) | 0.0040 (6) |
O5 | 0.0228 (8) | 0.0232 (8) | 0.0155 (7) | 0.0008 (6) | 0.0096 (6) | −0.0044 (6) |
O6 | 0.0192 (8) | 0.0162 (7) | 0.0212 (8) | 0.0005 (6) | 0.0062 (6) | 0.0040 (6) |
O7 | 0.0254 (9) | 0.0324 (9) | 0.0201 (8) | −0.0034 (7) | −0.0068 (7) | −0.0009 (7) |
O8 | 0.0254 (8) | 0.0215 (8) | 0.0171 (8) | 0.0040 (7) | 0.0088 (6) | 0.0074 (6) |
O9 | 0.0132 (7) | 0.0222 (8) | 0.0330 (9) | −0.0019 (6) | 0.0057 (7) | 0.0036 (7) |
O10 | 0.0272 (9) | 0.0410 (10) | 0.0247 (9) | 0.0053 (8) | 0.0175 (7) | 0.0025 (7) |
O11 | 0.0341 (9) | 0.0233 (8) | 0.0209 (8) | −0.0003 (7) | 0.0158 (7) | 0.0035 (6) |
O12 | 0.0227 (8) | 0.0138 (7) | 0.0256 (8) | −0.0020 (6) | 0.0038 (6) | −0.0028 (6) |
C1—N2 | 1.438 (2) | C11—H11 | 0.92 (2) |
C1—N12 | 1.477 (2) | N1—O2 | 1.214 (2) |
C1—C9 | 1.574 (3) | N1—O1 | 1.218 (2) |
C1—H1 | 0.90 (2) | N1—N2 | 1.411 (2) |
C3—N2 | 1.446 (2) | N3—O3 | 1.215 (2) |
C3—N4 | 1.480 (2) | N3—O4 | 1.225 (2) |
C3—C7 | 1.573 (3) | N3—N4 | 1.381 (2) |
C3—H3 | 0.96 (2) | N5—O6 | 1.218 (2) |
C5—N6 | 1.455 (2) | N5—O5 | 1.228 (2) |
C5—N4 | 1.458 (2) | N5—N6 | 1.375 (2) |
C5—C11 | 1.587 (3) | N7—O7 | 1.215 (2) |
C5—H5 | 0.96 (2) | N7—O8 | 1.222 (2) |
C7—N8 | 1.441 (2) | N7—N8 | 1.387 (2) |
C7—N6 | 1.465 (2) | N9—O9 | 1.212 (2) |
C7—H7 | 0.94 (2) | N9—O10 | 1.217 (2) |
C9—N8 | 1.447 (2) | N9—N10 | 1.431 (2) |
C9—N10 | 1.472 (2) | N11—O11 | 1.211 (2) |
C9—H9 | 0.94 (2) | N11—O12 | 1.216 (2) |
C11—N10 | 1.463 (2) | N11—N12 | 1.425 (2) |
C11—N12 | 1.464 (2) | ||
N2—C1—N12 | 111.36 (16) | O2—N1—O1 | 127.17 (17) |
N2—C1—C9 | 107.49 (15) | O2—N1—N2 | 116.28 (16) |
N12—C1—C9 | 104.70 (15) | O1—N1—N2 | 116.50 (17) |
N2—C1—H1 | 108.8 (13) | N1—N2—C1 | 118.76 (15) |
N12—C1—H1 | 109.9 (13) | N1—N2—C3 | 118.34 (15) |
C9—C1—H1 | 114.6 (13) | C1—N2—C3 | 117.04 (15) |
N2—C3—N4 | 113.92 (15) | O3—N3—O4 | 126.91 (17) |
N2—C3—C7 | 108.06 (15) | O3—N3—N4 | 117.02 (15) |
N4—C3—C7 | 101.11 (14) | O4—N3—N4 | 116.04 (15) |
N2—C3—H3 | 108.0 (11) | N3—N4—C5 | 117.03 (14) |
N4—C3—H3 | 111.2 (12) | N3—N4—C3 | 119.88 (14) |
C7—C3—H3 | 114.5 (11) | C5—N4—C3 | 110.82 (15) |
N6—C5—N4 | 95.64 (14) | O6—N5—O5 | 126.70 (17) |
N6—C5—C11 | 112.92 (16) | O6—N5—N6 | 116.42 (15) |
N4—C5—C11 | 112.56 (15) | O5—N5—N6 | 116.82 (15) |
N6—C5—H5 | 112.5 (13) | N5—N6—C5 | 118.79 (15) |
N4—C5—H5 | 111.6 (13) | N5—N6—C7 | 119.19 (15) |
C11—C5—H5 | 110.9 (13) | C5—N6—C7 | 111.12 (14) |
N8—C7—N6 | 111.74 (16) | O7—N7—O8 | 126.17 (17) |
N8—C7—C3 | 109.38 (15) | O7—N7—N8 | 116.76 (16) |
N6—C7—C3 | 101.83 (14) | O8—N7—N8 | 117.06 (16) |
N8—C7—H7 | 109.4 (13) | N7—N8—C7 | 120.47 (15) |
N6—C7—H7 | 109.7 (12) | N7—N8—C9 | 121.44 (16) |
C3—C7—H7 | 114.7 (13) | C7—N8—C9 | 118.05 (15) |
N8—C9—N10 | 108.35 (16) | O9—N9—O10 | 127.91 (18) |
N8—C9—C1 | 109.89 (15) | O9—N9—N10 | 116.47 (16) |
N10—C9—C1 | 104.40 (14) | O10—N9—N10 | 115.46 (17) |
N8—C9—H9 | 107.6 (12) | N9—N10—C11 | 116.27 (14) |
N10—C9—H9 | 113.1 (12) | N9—N10—C9 | 117.17 (15) |
C1—C9—H9 | 113.4 (12) | C11—N10—C9 | 107.91 (15) |
N10—C11—N12 | 104.57 (15) | O11—N11—O12 | 127.72 (16) |
N10—C11—C5 | 108.92 (15) | O11—N11—N12 | 116.27 (15) |
N12—C11—C5 | 107.48 (15) | O12—N11—N12 | 115.86 (16) |
N10—C11—H11 | 110.6 (13) | N11—N12—C11 | 116.02 (15) |
N12—C11—H11 | 112.4 (13) | N11—N12—C1 | 117.08 (15) |
C5—C11—H11 | 112.5 (13) | C11—N12—C1 | 107.66 (15) |
C6H6N12O12 | F(000) = 888 |
Mr = 438.23 | Dx = 2.083 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.7910 (18) Å | Cell parameters from 3033 reflections |
b = 12.481 (3) Å | θ = 4.6–58.3° |
c = 13.285 (3) Å | µ = 0.20 mm−1 |
β = 106.55 (3)° | T = 100 K |
V = 1397.2 (5) Å3 | Block, colorless |
Z = 4 | 0.30 × 0.20 × 0.20 mm |
Radiation source: fine-focus sealed tube | 2666 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
Absorption correction: empirical Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | θmax = 29.8°, θmin = 2.3° |
Tmin = 0.936, Tmax = 1.000 | h = −12→10 |
9849 measured reflections | k = −15→17 |
3651 independent reflections | l = −18→15 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.092 | w = 1/[σ2(Fo2) + (0.0372P)2 + 0.6042P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.112 |
3651 reflections | Δρmax = 0.37 e Å−3 |
296 parameters | Δρmin = −0.32 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0065 (9) |
C6H6N12O12 | V = 1397.2 (5) Å3 |
Mr = 438.23 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.7910 (18) Å | µ = 0.20 mm−1 |
b = 12.481 (3) Å | T = 100 K |
c = 13.285 (3) Å | 0.30 × 0.20 × 0.20 mm |
β = 106.55 (3)° |
Absorption correction: empirical Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | 3651 independent reflections |
Tmin = 0.936, Tmax = 1.000 | 2666 reflections with I > 2σ(I) |
9849 measured reflections | Rint = 0.040 |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.092 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | (Δ/σ)max = 0.112 |
3651 reflections | Δρmax = 0.37 e Å−3 |
296 parameters | Δρmin = −0.32 e Å−3 |
Experimental. The decay correction was applied simultaneously with the absorption correction in SADABS. No formal measure of the extent of decay is printed out by this program. The final unit cell is obtained from the refinement of the XYZ weighted centroids of reflections above 15 σ(I). |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.4318 (2) | −0.23594 (15) | 0.21295 (14) | 0.0097 (4) | |
H1 | 0.386 (2) | −0.3002 (17) | 0.1853 (16) | 0.012 (5)* | |
C3 | 0.6608 (2) | −0.11870 (14) | 0.22128 (14) | 0.0107 (4) | |
H3 | 0.748 (2) | −0.1154 (14) | 0.1950 (14) | 0.006 (5)* | |
C5 | 0.5867 (2) | −0.06174 (14) | 0.37491 (15) | 0.0101 (4) | |
H5 | 0.626 (2) | −0.0337 (15) | 0.4414 (15) | 0.002 (4)* | |
C7 | 0.5471 (2) | −0.01879 (14) | 0.19224 (14) | 0.0099 (4) | |
H7 | 0.584 (2) | 0.0322 (16) | 0.1536 (16) | 0.012 (5)* | |
C9 | 0.3167 (2) | −0.13679 (14) | 0.18275 (14) | 0.0101 (4) | |
H9 | 0.215 (2) | −0.1538 (14) | 0.1343 (14) | 0.000 (4)* | |
C11 | 0.4376 (2) | −0.13737 (14) | 0.36686 (14) | 0.0098 (4) | |
H11 | 0.418 (2) | −0.1410 (15) | 0.4300 (15) | 0.003 (4)* | |
N1 | 0.64823 (19) | −0.29931 (12) | 0.14541 (12) | 0.0139 (3) | |
N2 | 0.56941 (17) | −0.21328 (12) | 0.17818 (12) | 0.0111 (3) | |
N3 | 0.78711 (18) | −0.19951 (12) | 0.39532 (12) | 0.0128 (3) | |
N4 | 0.70831 (18) | −0.11394 (12) | 0.33713 (12) | 0.0105 (3) | |
N5 | 0.45091 (18) | 0.10406 (12) | 0.30470 (12) | 0.0113 (3) | |
N6 | 0.55296 (18) | 0.02314 (11) | 0.29666 (11) | 0.0097 (3) | |
N7 | 0.31335 (18) | −0.01129 (12) | 0.03787 (12) | 0.0123 (3) | |
N8 | 0.39019 (18) | −0.05405 (12) | 0.13583 (12) | 0.0109 (3) | |
N9 | 0.14986 (18) | −0.10703 (12) | 0.30257 (13) | 0.0133 (3) | |
N10 | 0.30229 (17) | −0.09702 (12) | 0.28399 (11) | 0.0105 (3) | |
N11 | 0.41827 (18) | −0.33289 (12) | 0.37300 (12) | 0.0131 (3) | |
N12 | 0.47317 (18) | −0.24187 (11) | 0.32874 (11) | 0.0100 (3) | |
O1 | 0.59001 (17) | −0.38801 (11) | 0.14527 (12) | 0.0225 (3) | |
O2 | 0.76376 (16) | −0.27594 (11) | 0.11673 (10) | 0.0166 (3) | |
O3 | 0.84853 (16) | −0.26379 (10) | 0.34949 (10) | 0.0164 (3) | |
O4 | 0.79028 (16) | −0.20162 (11) | 0.48817 (10) | 0.0177 (3) | |
O5 | 0.42046 (16) | 0.11271 (10) | 0.38926 (10) | 0.0150 (3) | |
O6 | 0.40260 (15) | 0.16107 (10) | 0.22766 (10) | 0.0140 (3) | |
O7 | 0.19078 (17) | −0.05467 (11) | −0.01134 (11) | 0.0211 (3) | |
O8 | 0.37694 (16) | 0.06506 (10) | 0.00896 (10) | 0.0153 (3) | |
O9 | 0.03681 (15) | −0.11716 (10) | 0.22562 (11) | 0.0168 (3) | |
O10 | 0.14941 (17) | −0.09752 (12) | 0.39367 (11) | 0.0220 (3) | |
O11 | 0.40149 (17) | −0.32144 (11) | 0.45976 (10) | 0.0180 (3) | |
O12 | 0.40197 (16) | −0.41481 (10) | 0.32114 (10) | 0.0159 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0099 (8) | 0.0106 (9) | 0.0095 (9) | −0.0005 (7) | 0.0043 (7) | −0.0006 (7) |
C3 | 0.0099 (9) | 0.0120 (9) | 0.0102 (9) | 0.0006 (7) | 0.0028 (7) | 0.0007 (7) |
C5 | 0.0105 (9) | 0.0103 (9) | 0.0092 (9) | 0.0015 (7) | 0.0025 (7) | −0.0001 (7) |
C7 | 0.0091 (8) | 0.0129 (9) | 0.0078 (9) | −0.0001 (7) | 0.0027 (7) | 0.0005 (7) |
C9 | 0.0094 (9) | 0.0104 (8) | 0.0102 (9) | −0.0010 (7) | 0.0025 (7) | 0.0001 (7) |
C11 | 0.0114 (9) | 0.0103 (8) | 0.0079 (9) | 0.0007 (7) | 0.0031 (7) | −0.0001 (7) |
N1 | 0.0145 (8) | 0.0151 (8) | 0.0117 (8) | 0.0040 (7) | 0.0029 (6) | −0.0011 (6) |
N2 | 0.0100 (7) | 0.0116 (7) | 0.0127 (8) | 0.0001 (6) | 0.0047 (6) | −0.0026 (6) |
N3 | 0.0095 (7) | 0.0142 (8) | 0.0142 (8) | 0.0001 (6) | 0.0025 (6) | 0.0010 (6) |
N4 | 0.0102 (7) | 0.0111 (7) | 0.0099 (7) | 0.0020 (6) | 0.0024 (6) | 0.0006 (6) |
N5 | 0.0089 (7) | 0.0109 (7) | 0.0140 (8) | −0.0024 (6) | 0.0030 (6) | −0.0010 (6) |
N6 | 0.0110 (7) | 0.0082 (7) | 0.0102 (7) | 0.0011 (6) | 0.0037 (6) | 0.0001 (6) |
N7 | 0.0131 (8) | 0.0141 (8) | 0.0094 (8) | 0.0046 (7) | 0.0025 (6) | −0.0008 (6) |
N8 | 0.0098 (7) | 0.0140 (8) | 0.0076 (7) | −0.0007 (6) | 0.0003 (6) | 0.0022 (6) |
N9 | 0.0107 (8) | 0.0115 (8) | 0.0198 (9) | 0.0008 (6) | 0.0079 (7) | 0.0024 (6) |
N10 | 0.0073 (7) | 0.0136 (8) | 0.0112 (8) | −0.0004 (6) | 0.0038 (6) | 0.0000 (6) |
N11 | 0.0104 (8) | 0.0124 (8) | 0.0164 (8) | 0.0002 (6) | 0.0037 (6) | 0.0031 (6) |
N12 | 0.0115 (7) | 0.0091 (7) | 0.0097 (8) | −0.0011 (6) | 0.0037 (6) | 0.0006 (6) |
O1 | 0.0219 (8) | 0.0126 (7) | 0.0358 (9) | −0.0011 (6) | 0.0127 (7) | −0.0042 (6) |
O2 | 0.0150 (7) | 0.0210 (7) | 0.0166 (7) | 0.0028 (6) | 0.0089 (6) | 0.0010 (6) |
O3 | 0.0145 (7) | 0.0188 (7) | 0.0171 (7) | 0.0064 (6) | 0.0064 (6) | 0.0015 (6) |
O4 | 0.0197 (7) | 0.0220 (7) | 0.0101 (7) | 0.0037 (6) | 0.0021 (5) | 0.0027 (6) |
O5 | 0.0169 (7) | 0.0169 (7) | 0.0129 (7) | 0.0001 (6) | 0.0071 (5) | −0.0032 (5) |
O6 | 0.0131 (7) | 0.0129 (6) | 0.0160 (7) | 0.0004 (5) | 0.0039 (5) | 0.0031 (5) |
O7 | 0.0175 (7) | 0.0233 (8) | 0.0165 (7) | −0.0024 (6) | −0.0050 (6) | −0.0010 (6) |
O8 | 0.0179 (7) | 0.0152 (7) | 0.0144 (7) | 0.0022 (6) | 0.0073 (6) | 0.0051 (5) |
O9 | 0.0093 (6) | 0.0162 (7) | 0.0239 (8) | −0.0004 (6) | 0.0034 (6) | 0.0026 (6) |
O10 | 0.0211 (8) | 0.0296 (8) | 0.0198 (8) | 0.0035 (7) | 0.0131 (6) | 0.0015 (6) |
O11 | 0.0242 (8) | 0.0180 (7) | 0.0153 (7) | 0.0000 (6) | 0.0113 (6) | 0.0032 (5) |
O12 | 0.0164 (7) | 0.0104 (6) | 0.0194 (7) | −0.0008 (5) | 0.0027 (6) | −0.0010 (5) |
C1—N2 | 1.441 (2) | N1—N2 | 1.412 (2) |
C1—N12 | 1.478 (2) | N3—O3 | 1.222 (2) |
C1—C9 | 1.576 (3) | N3—O4 | 1.226 (2) |
C3—N2 | 1.451 (2) | N3—N4 | 1.383 (2) |
C3—N4 | 1.477 (2) | N5—O6 | 1.2191 (19) |
C3—C7 | 1.576 (3) | N5—O5 | 1.2315 (19) |
C5—N6 | 1.454 (2) | N5—N6 | 1.375 (2) |
C5—N4 | 1.458 (2) | N7—O7 | 1.217 (2) |
C5—C11 | 1.593 (3) | N7—O8 | 1.221 (2) |
C7—N8 | 1.439 (2) | N7—N8 | 1.391 (2) |
C7—N6 | 1.470 (2) | N9—O9 | 1.212 (2) |
C9—N8 | 1.450 (2) | N9—O10 | 1.217 (2) |
C9—N10 | 1.473 (2) | N9—N10 | 1.435 (2) |
C11—N10 | 1.461 (2) | N11—O11 | 1.211 (2) |
C11—N12 | 1.465 (2) | N11—O12 | 1.218 (2) |
N1—O2 | 1.217 (2) | N11—N12 | 1.425 (2) |
N1—O1 | 1.219 (2) | ||
N2—C1—N12 | 111.28 (15) | N3—N4—C5 | 116.89 (14) |
N2—C1—C9 | 107.52 (14) | N3—N4—C3 | 119.96 (14) |
N12—C1—C9 | 104.72 (14) | C5—N4—C3 | 111.06 (14) |
N2—C3—N4 | 113.86 (14) | O6—N5—O5 | 126.90 (16) |
N2—C3—C7 | 107.82 (14) | O6—N5—N6 | 116.25 (14) |
N4—C3—C7 | 101.23 (13) | O5—N5—N6 | 116.83 (15) |
N6—C5—N4 | 95.71 (13) | N5—N6—C5 | 118.95 (14) |
N6—C5—C11 | 112.78 (15) | N5—N6—C7 | 119.12 (14) |
N4—C5—C11 | 112.44 (14) | C5—N6—C7 | 111.13 (13) |
N8—C7—N6 | 111.78 (14) | O7—N7—O8 | 126.38 (16) |
N8—C7—C3 | 109.43 (15) | O7—N7—N8 | 116.86 (15) |
N6—C7—C3 | 101.63 (13) | O8—N7—N8 | 116.75 (15) |
N8—C9—N10 | 108.50 (14) | N7—N8—C7 | 120.54 (14) |
N8—C9—C1 | 109.65 (14) | N7—N8—C9 | 121.23 (14) |
N10—C9—C1 | 104.36 (14) | C7—N8—C9 | 118.21 (15) |
N10—C11—N12 | 104.74 (14) | O9—N9—O10 | 127.91 (16) |
N10—C11—C5 | 108.90 (14) | O9—N9—N10 | 116.44 (14) |
N12—C11—C5 | 107.37 (14) | O10—N9—N10 | 115.47 (15) |
O2—N1—O1 | 127.17 (16) | N9—N10—C11 | 116.12 (14) |
O2—N1—N2 | 116.15 (15) | N9—N10—C9 | 117.07 (14) |
O1—N1—N2 | 116.62 (15) | C11—N10—C9 | 107.97 (14) |
N1—N2—C1 | 118.70 (14) | O11—N11—O12 | 127.62 (16) |
N1—N2—C3 | 118.37 (14) | O11—N11—N12 | 116.48 (15) |
C1—N2—C3 | 117.03 (14) | O12—N11—N12 | 115.77 (15) |
O3—N3—O4 | 126.91 (16) | N11—N12—C11 | 115.89 (14) |
O3—N3—N4 | 116.78 (15) | N11—N12—C1 | 117.21 (14) |
O4—N3—N4 | 116.30 (14) | C11—N12—C1 | 107.56 (14) |
Experimental details
(298gHNIW) | (250gHNIW) | (200gHNIW) | (150gHNIW) | |
Crystal data | ||||
Chemical formula | C6H6N12O12 | C6H6N12O12 | C6H6N12O12 | C6H6N12O12 |
Mr | 438.23 | 438.23 | 438.23 | 438.23 |
Crystal system, space group | Monoclinic, P21/n | Monoclinic, P21/n | Monoclinic, P21/n | Monoclinic, P21/n |
Temperature (K) | 298 | 250 | 200 | 150 |
a, b, c (Å) | 13.2272 (7), 8.1692 (5), 14.8920 (8) | 13.1670 (3), 8.1676 (1), 14.8436 (1) | 13.1156 (7), 8.1713 (4), 14.8059 (8) | 13.0698 (4), 8.1737 (3), 14.7718 (5) |
β (°) | 109.164 (1) | 109.001 (1) | 108.841 (1) | 108.696 (1) |
V (Å3) | 1520.0 (2) | 1509.34 (4) | 1501.75 (14) | 1494.78 (9) |
Z | 4 | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.18 | 0.19 | 0.19 | 0.19 |
Crystal size (mm) | 0.37 × 0.33 × 0.18 | 0.37 × 0.33 × 0.18 | 0.37 × 0.33 × 0.18 | 0.37 × 0.33 × 0.18 |
Data collection | ||||
Diffractometer | Platform diffractometer | Platform diffractometer | Platform diffractometer | Platform diffractometer |
Absorption correction | Empirical :Multipole Expansion Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | Empirical :Multipole Expansion Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | Empirical :Multipole Expansion Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | Empirical :Multipole Expansion Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany |
Tmin, Tmax | 0.627, 0.990 | 0.743, 0.990 | 0.737, 0.990 | 0.776, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10300, 3746, 2671 | 10203, 3714, 2772 | 10149, 3686, 2875 | 10088, 3678, 2981 |
Rint | 0.039 | 0.037 | 0.036 | 0.034 |
(sin θ/λ)max (Å−1) | 0.667 | 0.667 | 0.666 | 0.667 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.115, 1.02 | 0.039, 0.109, 1.03 | 0.037, 0.101, 1.04 | 0.035, 0.095, 1.04 |
No. of reflections | 3746 | 3714 | 3686 | 3678 |
No. of parameters | 296 | 296 | 296 | 296 |
H-atom treatment | ? | ? | ? | ? |
(Δ/σ)max | −0.001 | < 0.001 | 0.001 | −0.001 |
Δρmax, Δρmin (e Å−3) | 0.27, −0.22 | 0.31, −0.22 | 0.34, −0.24 | 0.32, −0.26 |
(100gHNIW) | (298eHNIW) | (250eHNIW) | (200eHNIW) | |
Crystal data | ||||
Chemical formula | C6H6N12O12 | C6H6N12O12 | C6H6N12O12 | C6H6N12O12 |
Mr | 438.23 | 438.23 | 438.23 | 438.23 |
Crystal system, space group | Monoclinic, P21/n | Monoclinic, P21/n | Monoclinic, P21/n | Monoclinic, P21/n |
Temperature (K) | 100 | 298 | 250 | 200 |
a, b, c (Å) | 13.0342 (3), 8.1773 (2), 14.7465 (2) | 8.8628 (11), 12.5928 (16), 13.3947 (17) | 8.8408 (9), 12.5622 (12), 13.3577 (13) | 8.8212 (10), 12.5368 (14), 13.3330 (15) |
β (°) | 108.566 (1) | 106.920 (2) | 106.820 (2) | 106.740 (2) |
V (Å3) | 1489.95 (5) | 1430.2 (3) | 1420.0 (2) | 1412.0 (3) |
Z | 4 | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.19 | 0.20 | 0.20 | 0.20 |
Crystal size (mm) | 0.37 × 0.33 × 0.18 | 0.30 × 0.20 × 0.20 | 0.30 × 0.20 × 0.20 | 0.30 × 0.20 × 0.20 |
Data collection | ||||
Diffractometer | Platform diffractometer | ? | ? | ? |
Absorption correction | Empirical :Multipole Expansion Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | Empirical Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | Empirical Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | Empirical Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany |
Tmin, Tmax | 0.772, 0.990 | 0.858, 1.000 | 0.872, 1.000 | 0.878, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9973, 3658, 3005 | 9342, 3735, 2174 | 9290, 3712, 2338 | 9186, 3681, 2355 |
Rint | 0.036 | 0.050 | 0.046 | 0.044 |
(sin θ/λ)max (Å−1) | 0.666 | 0.698 | 0.697 | 0.699 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.093, 1.04 | 0.056, 0.116, 1.00 | 0.054, 0.113, 1.00 | 0.045, 0.104, 0.97 |
No. of reflections | 3658 | 3735 | 3712 | 3681 |
No. of parameters | 296 | 296 | 296 | 296 |
H-atom treatment | ? | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
(Δ/σ)max | 0.001 | 0.058 | 0.038 | 0.039 |
Δρmax, Δρmin (e Å−3) | 0.38, −0.28 | 0.26, −0.25 | 0.35, −0.27 | 0.33, −0.32 |
(150eHNIW) | (100eHNIW) | |
Crystal data | ||
Chemical formula | C6H6N12O12 | C6H6N12O12 |
Mr | 438.23 | 438.23 |
Crystal system, space group | Monoclinic, P21/n | Monoclinic, P21/n |
Temperature (K) | 150 | 100 |
a, b, c (Å) | 8.8004 (10), 12.4992 (14), 13.2985 (15) | 8.7910 (18), 12.481 (3), 13.285 (3) |
β (°) | 106.622 (2) | 106.55 (3) |
V (Å3) | 1401.7 (3) | 1397.2 (5) |
Z | 4 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.20 | 0.20 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 | 0.30 × 0.20 × 0.20 |
Data collection | ||
Diffractometer | ? | ? |
Absorption correction | Empirical Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany | Empirical Sheldrick G.M. (1996) SADABS, Univ. Goettingen, Germany |
Tmin, Tmax | 0.880, 1.000 | 0.936, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9177, 3669, 2398 | 9849, 3651, 2666 |
Rint | 0.046 | 0.040 |
(sin θ/λ)max (Å−1) | 0.694 | 0.698 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.100, 0.98 | 0.044, 0.092, 1.02 |
No. of reflections | 3669 | 3651 |
No. of parameters | 296 | 296 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
(Δ/σ)max | 0.036 | 0.112 |
Δρmax, Δρmin (e Å−3) | 0.35, −0.32 | 0.37, −0.32 |
Computer programs: Siemens SMART, Siemens SAINT, SHELXS86 (Sheldrick, 1990), SHELXS97 (Sheldrick, 1990), SHELXL93 (Sheldrick, 1993), SHELXL97 (Sheldrick, 1997), Siemens SHELXTL and the Toledo cifomatic.