Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804006622/cf6316sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804006622/cf6316Isup2.hkl |
CCDC reference: 239149
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.012 Å
- Disorder in solvent or counterion
- R factor = 0.037
- wR factor = 0.067
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT214_ALERT_2_A Atom C12 (Anion/Solvent) ADP max/min Ratio 7.70 oblate PLAT214_ALERT_2_A Atom C12' (Anion/Solvent) ADP max/min Ratio 7.70 oblate PLAT214_ALERT_2_A Atom C12" (Anion/Solvent) ADP max/min Ratio 7.70 oblate PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 6.09 Ratio
Alert level B PLAT250_ALERT_2_B Large U3/U1 Ratio for Average U(i,j) Tensor .... 6.93 PLAT731_ALERT_1_B Bond Calc 0.86(5), Rep 0.856(10) ...... 5.00 su-Rat N3 -H3N 1.555 1.555 PLAT731_ALERT_1_B Bond Calc 0.86(6), Rep 0.855(10) ...... 6.00 su-Rat N3' -H3N' 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.86(5), Rep 0.856(10) ...... 5.00 su-Rat N3 -H3N 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.86(6), Rep 0.855(10) ...... 6.00 su-Rat N3' -H11# 1.555 1.555
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.14 Ratio PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors .... C12 PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors .... C12' PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors .... C12" PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... O2' PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 33.00 Perc. PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 12 PLAT432_ALERT_2_C Short Inter X...Y Contact Br2 .. C5' .. 3.30 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact C1' .. O2' .. 2.96 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 11 PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.01
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C11.5 H13 Br2 N5 O1.5 Atom count from the _atom_site data: C11.495 H12.98 Br2 N5 O1.495 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G ALERT: check formula stoichiometry or atom site occupancies. From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C11.50 H13 Br2 N5 O1.50 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 46.00 45.98 0.02 H 52.00 51.92 0.08 Br 8.00 8.00 0.00 N 20.00 20.00 0.00 O 6.00 5.98 0.02 REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.49 From the CIF: _reflns_number_total 5939 Count of symmetry unique reflns 3061 Completeness (_total/calc) 194.02% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2878 Fraction of Friedel pairs measured 0.940 Are heavy atom types Z>Si present yes
4 ALERT level A = In general: serious problem 5 ALERT level B = Potentially serious problem 17 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 11 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 8 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C11H11Br2N5O·0.5CH4O | F(000) = 796 |
Mr = 405.09 | Dx = 1.864 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.646 (1) Å | Cell parameters from 38 reflections |
b = 28.050 (6) Å | θ = 3.0–15.3° |
c = 7.670 (1) Å | µ = 5.62 mm−1 |
β = 118.65 (1)° | T = 296 K |
V = 1443.5 (5) Å3 | Irregular, colourless |
Z = 4 | 0.48 × 0.30 × 0.22 mm |
Siemens P4 diffractometer | 3078 reflections with I > 2σ(I) |
Radiation source: normal-focus sealed tube | Rint = 0.037 |
Graphite monochromator | θmax = 26.5°, θmin = 1.5° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (SHELXTL; Siemens, 1994) | k = −35→35 |
Tmin = 0.104, Tmax = 0.290 | l = −9→8 |
6923 measured reflections | 3 standard reflections every 97 reflections |
5939 independent reflections | intensity decay: 7.6% |
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)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.067 | w = 1/[σ2(Fo2) + (0.023P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.80 | (Δ/σ)max = 0.001 |
5939 reflections | Δρmax = 0.29 e Å−3 |
393 parameters | Δρmin = −0.43 e Å−3 |
6 restraints | Absolute structure: Flack (1983); 2877 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.000 (11) |
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 | Occ. (<1) | |
Br1 | 0.07477 (12) | 0.31318 (3) | 0.15611 (12) | 0.0632 (2) | |
Br2 | 0.53599 (13) | 0.31463 (3) | 0.61841 (11) | 0.0643 (3) | |
O1 | 0.5937 (7) | 0.4200 (2) | −0.0777 (7) | 0.0585 (17) | |
N1 | 0.6139 (8) | 0.37401 (19) | 0.3654 (8) | 0.0336 (14) | |
N2 | 0.8398 (9) | 0.4254 (2) | 0.2423 (8) | 0.0393 (15) | |
N3 | 0.7876 (9) | 0.4169 (2) | 0.6741 (8) | 0.0407 (15) | |
N4 | 0.8379 (8) | 0.47357 (18) | 0.4973 (7) | 0.0369 (14) | |
N5 | 0.7163 (9) | 0.4963 (2) | 0.7097 (8) | 0.0536 (18) | |
H5AN | 0.7132 | 0.5259 | 0.6799 | 0.064* | |
H5BN | 0.6788 | 0.4875 | 0.7941 | 0.064* | |
C1 | 0.6538 (12) | 0.4136 (3) | 0.1039 (11) | 0.039 (2) | |
C2 | 0.5297 (12) | 0.3891 (3) | 0.1706 (11) | 0.042 (2) | |
C3 | 0.3436 (12) | 0.3725 (3) | 0.0720 (12) | 0.049 (2) | |
H3 | 0.2539 | 0.3777 | −0.0612 | 0.059* | |
C4 | 0.3084 (11) | 0.3458 (3) | 0.2048 (11) | 0.045 (2) | |
C5 | 0.4696 (12) | 0.3471 (2) | 0.3814 (11) | 0.0372 (19) | |
C6 | 0.8073 (10) | 0.3908 (2) | 0.5273 (9) | 0.0344 (17) | |
H6 | 0.8990 | 0.3640 | 0.5871 | 0.041* | |
C7 | 0.8977 (10) | 0.4278 (2) | 0.4500 (10) | 0.0372 (17) | |
C8 | 1.1223 (11) | 0.4253 (3) | 0.5398 (11) | 0.054 (3) | |
H8A | 1.1667 | 0.3926 | 0.5488 | 0.064* | |
H8B | 1.1874 | 0.4394 | 0.6713 | 0.064* | |
C9 | 1.1667 (11) | 0.4543 (3) | 0.3933 (10) | 0.055 (2) | |
H9A | 1.1869 | 0.4877 | 0.4304 | 0.067* | |
H9B | 1.2850 | 0.4422 | 0.3921 | 0.067* | |
C10 | 0.9877 (10) | 0.4480 (3) | 0.1949 (10) | 0.050 (2) | |
H10A | 0.9396 | 0.4785 | 0.1294 | 0.060* | |
H10B | 1.0171 | 0.4276 | 0.1102 | 0.060* | |
C11 | 0.7790 (10) | 0.4639 (2) | 0.6250 (9) | 0.0350 (17) | |
Br1' | 0.14905 (11) | 0.25068 (3) | 0.74252 (11) | 0.0551 (2) | |
Br2' | 0.63555 (13) | 0.25818 (3) | 1.18084 (12) | 0.0694 (3) | |
O1' | 0.8413 (8) | 0.1505 (2) | 0.6499 (8) | 0.0605 (17) | |
N1' | 0.3979 (8) | 0.19561 (18) | 0.6430 (9) | 0.0338 (14) | |
N2' | 0.5234 (9) | 0.1458 (2) | 0.4150 (9) | 0.0385 (16) | |
N3' | 0.0878 (8) | 0.1523 (2) | 0.4679 (9) | 0.0403 (16) | |
N4' | 0.2684 (8) | 0.09573 (19) | 0.4190 (8) | 0.0414 (15) | |
N5' | 0.0522 (9) | 0.07287 (19) | 0.5389 (9) | 0.0573 (19) | |
H5'C | 0.0824 | 0.0432 | 0.5453 | 0.069* | |
H5'D | −0.0338 | 0.0822 | 0.5737 | 0.069* | |
C1' | 0.6654 (12) | 0.1574 (3) | 0.5970 (12) | 0.042 (2) | |
C2' | 0.5977 (11) | 0.1822 (3) | 0.7182 (12) | 0.0401 (19) | |
C3' | 0.7063 (11) | 0.2010 (3) | 0.9035 (11) | 0.047 (2) | |
H3' | 0.8431 | 0.1978 | 0.9848 | 0.056* | |
C4' | 0.5756 (12) | 0.2260 (2) | 0.9497 (11) | 0.044 (2) | |
C5' | 0.3900 (11) | 0.2225 (2) | 0.7843 (12) | 0.042 (2) | |
C6' | 0.2387 (10) | 0.1801 (2) | 0.4503 (10) | 0.0353 (18) | |
H6' | 0.1792 | 0.2073 | 0.3606 | 0.042* | |
C7' | 0.3144 (10) | 0.1422 (2) | 0.3564 (9) | 0.0331 (16) | |
C8' | 0.2162 (13) | 0.1447 (3) | 0.1292 (10) | 0.054 (2) | |
H8'C | 0.0851 | 0.1302 | 0.0679 | 0.065* | |
H8'D | 0.2044 | 0.1774 | 0.0840 | 0.065* | |
C9' | 0.3583 (12) | 0.1168 (3) | 0.0828 (11) | 0.054 (2) | |
H9'C | 0.3204 | 0.0834 | 0.0614 | 0.065* | |
H9'D | 0.3570 | 0.1292 | −0.0359 | 0.065* | |
C10' | 0.5621 (11) | 0.1224 (3) | 0.2599 (10) | 0.054 (2) | |
H10C | 0.6260 | 0.0917 | 0.3057 | 0.065* | |
H10D | 0.6463 | 0.1424 | 0.2277 | 0.065* | |
C11' | 0.1386 (11) | 0.1045 (3) | 0.4752 (10) | 0.0414 (18) | |
O2 | 0.674 (3) | 0.0160 (8) | 0.988 (4) | 0.106 (9) | 0.33 |
H2O | 0.5853 | −0.0018 | 0.9102 | 0.127* | 0.33 |
C12 | 0.719 (13) | 0.0521 (12) | 0.874 (10) | 0.114 (8) | 0.33 |
H12A | 0.6596 | 0.0820 | 0.8782 | 0.137* | 0.33 |
H12B | 0.6654 | 0.0419 | 0.7389 | 0.137* | 0.33 |
H12C | 0.8605 | 0.0559 | 0.9322 | 0.137* | 0.33 |
O2' | 0.685 (2) | 0.0563 (5) | 0.714 (2) | 0.050 (4) | 0.33 |
H2'O | 0.6082 | 0.0351 | 0.6470 | 0.061* | 0.33 |
C12' | 0.694 (13) | 0.0579 (13) | 0.911 (6) | 0.114 (8) | 0.33 |
H12D | 0.7150 | 0.0901 | 0.9586 | 0.137* | 0.33 |
H12E | 0.8028 | 0.0384 | 1.0030 | 0.137* | 0.33 |
H12F | 0.5716 | 0.0461 | 0.9003 | 0.137* | 0.33 |
O2" | 0.498 (4) | 0.0198 (7) | 0.923 (3) | 0.116 (9) | 0.33 |
H2"O | 0.4092 | 0.0103 | 0.8157 | 0.139* | 0.33 |
C12" | 0.674 (6) | 0.0334 (12) | 0.902 (9) | 0.114 (8) | 0.33 |
H12G | 0.6688 | 0.0173 | 0.7888 | 0.137* | 0.33 |
H12H | 0.7932 | 0.0243 | 1.0193 | 0.137* | 0.33 |
H12I | 0.6737 | 0.0672 | 0.8831 | 0.137* | 0.33 |
H3N | 0.731 (6) | 0.4071 (16) | 0.741 (6) | 0.011 (14)* | |
H3N' | 0.017 (7) | 0.1669 (16) | 0.510 (8) | 0.022 (16)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0534 (5) | 0.0648 (6) | 0.0745 (6) | −0.0168 (6) | 0.0332 (5) | −0.0067 (6) |
Br2 | 0.0839 (7) | 0.0581 (6) | 0.0518 (5) | −0.0186 (6) | 0.0333 (5) | 0.0117 (5) |
O1 | 0.037 (4) | 0.107 (5) | 0.030 (3) | −0.003 (3) | 0.015 (3) | 0.016 (3) |
N1 | 0.040 (4) | 0.038 (3) | 0.024 (3) | 0.000 (3) | 0.017 (3) | 0.001 (3) |
N2 | 0.040 (4) | 0.047 (4) | 0.035 (4) | −0.004 (3) | 0.022 (3) | 0.005 (3) |
N3 | 0.052 (4) | 0.043 (4) | 0.030 (3) | −0.008 (3) | 0.022 (3) | 0.004 (3) |
N4 | 0.043 (4) | 0.035 (4) | 0.041 (3) | 0.000 (3) | 0.027 (3) | 0.008 (3) |
N5 | 0.083 (5) | 0.041 (4) | 0.062 (4) | −0.010 (4) | 0.056 (4) | −0.003 (3) |
C1 | 0.043 (6) | 0.052 (5) | 0.027 (4) | 0.004 (4) | 0.020 (4) | 0.001 (4) |
C2 | 0.040 (5) | 0.058 (5) | 0.033 (5) | −0.001 (4) | 0.022 (4) | 0.006 (4) |
C3 | 0.034 (5) | 0.072 (6) | 0.043 (5) | 0.004 (4) | 0.019 (5) | 0.008 (4) |
C4 | 0.048 (6) | 0.047 (5) | 0.053 (5) | −0.012 (4) | 0.034 (5) | −0.005 (4) |
C5 | 0.042 (5) | 0.033 (4) | 0.041 (5) | 0.003 (4) | 0.023 (5) | 0.002 (4) |
C6 | 0.034 (4) | 0.037 (4) | 0.028 (4) | 0.004 (4) | 0.011 (4) | 0.006 (3) |
C7 | 0.037 (4) | 0.039 (5) | 0.041 (4) | −0.001 (4) | 0.023 (4) | 0.010 (4) |
C8 | 0.052 (6) | 0.052 (6) | 0.050 (6) | −0.005 (4) | 0.019 (5) | −0.001 (4) |
C9 | 0.048 (6) | 0.077 (6) | 0.056 (5) | 0.002 (5) | 0.036 (5) | 0.007 (5) |
C10 | 0.034 (5) | 0.064 (6) | 0.049 (5) | −0.011 (4) | 0.018 (4) | 0.007 (4) |
C11 | 0.032 (5) | 0.041 (5) | 0.030 (4) | −0.009 (4) | 0.013 (4) | 0.000 (3) |
Br1' | 0.0479 (5) | 0.0509 (5) | 0.0729 (5) | 0.0060 (5) | 0.0341 (5) | −0.0102 (5) |
Br2' | 0.0692 (7) | 0.0747 (7) | 0.0573 (5) | 0.0033 (6) | 0.0247 (5) | −0.0232 (6) |
O1' | 0.025 (3) | 0.106 (5) | 0.054 (4) | 0.009 (3) | 0.022 (3) | −0.011 (3) |
N1' | 0.026 (4) | 0.034 (3) | 0.048 (4) | 0.001 (3) | 0.023 (3) | 0.002 (3) |
N2' | 0.030 (4) | 0.058 (4) | 0.041 (4) | 0.000 (3) | 0.028 (4) | −0.001 (3) |
N3' | 0.027 (4) | 0.051 (4) | 0.057 (4) | 0.000 (3) | 0.030 (3) | −0.011 (3) |
N4' | 0.038 (4) | 0.041 (4) | 0.059 (4) | 0.000 (3) | 0.035 (3) | −0.006 (3) |
N5' | 0.066 (5) | 0.031 (4) | 0.103 (6) | −0.001 (3) | 0.064 (5) | −0.008 (4) |
C1' | 0.037 (6) | 0.052 (5) | 0.047 (6) | 0.005 (4) | 0.029 (5) | 0.007 (4) |
C2' | 0.036 (5) | 0.046 (5) | 0.050 (5) | −0.009 (4) | 0.029 (5) | −0.006 (4) |
C3' | 0.028 (5) | 0.065 (6) | 0.042 (5) | 0.001 (4) | 0.012 (4) | 0.002 (4) |
C4' | 0.047 (6) | 0.048 (5) | 0.051 (5) | 0.001 (4) | 0.035 (5) | 0.003 (4) |
C5' | 0.051 (6) | 0.029 (4) | 0.061 (6) | 0.008 (4) | 0.038 (5) | −0.007 (4) |
C6' | 0.030 (4) | 0.041 (5) | 0.030 (4) | 0.000 (4) | 0.010 (4) | 0.006 (3) |
C7' | 0.035 (4) | 0.043 (5) | 0.024 (4) | 0.005 (4) | 0.016 (3) | 0.000 (3) |
C8' | 0.071 (7) | 0.049 (6) | 0.049 (5) | 0.002 (5) | 0.033 (5) | −0.004 (4) |
C9' | 0.068 (7) | 0.059 (5) | 0.053 (5) | −0.002 (5) | 0.044 (5) | −0.013 (4) |
C10' | 0.044 (5) | 0.084 (6) | 0.040 (5) | 0.011 (5) | 0.024 (4) | 0.001 (4) |
C11' | 0.041 (5) | 0.039 (5) | 0.046 (5) | −0.002 (4) | 0.022 (4) | −0.006 (4) |
O2 | 0.056 (14) | 0.040 (13) | 0.19 (2) | 0.015 (11) | 0.030 (16) | 0.025 (14) |
C12 | 0.18 (2) | 0.006 (13) | 0.19 (2) | 0.010 (15) | 0.108 (15) | −0.010 (14) |
O2' | 0.062 (11) | 0.028 (9) | 0.052 (10) | 0.000 (7) | 0.019 (9) | 0.014 (8) |
C12' | 0.18 (2) | 0.006 (13) | 0.19 (2) | 0.010 (15) | 0.108 (15) | −0.010 (14) |
O2" | 0.21 (3) | 0.050 (13) | 0.084 (16) | 0.001 (18) | 0.07 (2) | −0.028 (11) |
C12" | 0.18 (2) | 0.006 (13) | 0.19 (2) | 0.010 (15) | 0.108 (15) | −0.010 (14) |
Br1—C4 | 1.878 (7) | N2'—C10' | 1.506 (8) |
Br2—C5 | 1.873 (7) | N3'—C11' | 1.391 (8) |
O1—C1 | 1.252 (7) | N3'—C6' | 1.451 (8) |
N1—C2 | 1.380 (8) | N3'—H3N' | 0.855 (10) |
N1—C5 | 1.390 (8) | N4'—C11' | 1.281 (8) |
N1—C6 | 1.480 (8) | N4'—C7' | 1.489 (8) |
N2—C1 | 1.346 (8) | N5'—C11' | 1.332 (8) |
N2—C7 | 1.436 (8) | N5'—H5'C | 0.860 |
N2—C10 | 1.486 (8) | N5'—H5'D | 0.860 |
N3—C11 | 1.363 (8) | C1'—C2' | 1.440 (10) |
N3—C6 | 1.411 (8) | C2'—C3' | 1.362 (9) |
N3—H3N | 0.856 (10) | C3'—C4' | 1.400 (9) |
N4—C11 | 1.288 (7) | C3'—H3' | 0.930 |
N4—C7 | 1.465 (8) | C4'—C5' | 1.380 (10) |
N5—C11 | 1.332 (8) | C6'—C7' | 1.543 (8) |
N5—H5AN | 0.860 | C6'—H6' | 0.980 |
N5—H5BN | 0.860 | C7'—C8' | 1.533 (9) |
C1—C2 | 1.449 (10) | C8'—C9' | 1.513 (10) |
C2—C3 | 1.335 (10) | C8'—H8'C | 0.970 |
C3—C4 | 1.390 (9) | C8'—H8'D | 0.970 |
C3—H3 | 0.930 | C9'—C10' | 1.506 (10) |
C4—C5 | 1.324 (9) | C9'—H9'C | 0.970 |
C6—C7 | 1.517 (8) | C9'—H9'D | 0.970 |
C6—H6 | 0.980 | C10'—H10C | 0.970 |
C7—C8 | 1.515 (9) | C10'—H10D | 0.970 |
C8—C9 | 1.551 (10) | O2—C12 | 1.480 (4) |
C8—H8A | 0.970 | O2—H2O | 0.820 |
C8—H8B | 0.970 | C12—H12A | 0.960 |
C9—C10 | 1.491 (9) | C12—H12B | 0.960 |
C9—H9A | 0.970 | C12—H12C | 0.960 |
C9—H9B | 0.970 | O2'—C12' | 1.480 (4) |
C10—H10A | 0.970 | O2'—H2'O | 0.820 |
C10—H10B | 0.970 | C12'—H12D | 0.960 |
Br1'—C5' | 1.885 (7) | C12'—H12E | 0.960 |
Br2'—C4' | 1.840 (7) | C12'—H12F | 0.960 |
O1'—C1' | 1.220 (8) | O2"—C12" | 1.480 (4) |
N1'—C5' | 1.346 (8) | O2"—H2"O | 0.820 |
N1'—C2' | 1.402 (8) | C12"—H12G | 0.960 |
N1'—C6' | 1.459 (8) | C12"—H12H | 0.960 |
N2'—C1' | 1.335 (9) | C12"—H12I | 0.960 |
N2'—C7' | 1.441 (8) | ||
C2—N1—C5 | 106.5 (6) | C11'—N5'—H5'D | 120.0 |
C2—N1—C6 | 124.8 (6) | H5'C—N5'—H5'D | 120.0 |
C5—N1—C6 | 127.9 (5) | O1'—C1'—N2' | 121.5 (7) |
C1—N2—C7 | 122.2 (6) | O1'—C1'—C2' | 122.9 (8) |
C1—N2—C10 | 123.5 (6) | N2'—C1'—C2' | 115.4 (7) |
C7—N2—C10 | 112.7 (6) | C3'—C2'—N1' | 108.9 (7) |
C11—N3—C6 | 106.9 (5) | C3'—C2'—C1' | 129.2 (7) |
C11—N3—H3N | 120 (3) | N1'—C2'—C1' | 121.5 (7) |
C6—N3—H3N | 126 (3) | C2'—C3'—C4' | 107.9 (7) |
C11—N4—C7 | 105.5 (5) | C2'—C3'—H3' | 126.1 |
C11—N5—H5AN | 120.0 | C4'—C3'—H3' | 126.1 |
C11—N5—H5BN | 120.0 | C5'—C4'—C3' | 106.0 (6) |
H5AN—N5—H5BN | 120.0 | C5'—C4'—Br2' | 126.3 (5) |
O1—C1—N2 | 121.9 (7) | C3'—C4'—Br2' | 127.7 (6) |
O1—C1—C2 | 120.4 (7) | N1'—C5'—C4' | 111.0 (6) |
N2—C1—C2 | 117.5 (6) | N1'—C5'—Br1' | 121.0 (6) |
C3—C2—N1 | 108.8 (7) | C4'—C5'—Br1' | 128.0 (5) |
C3—C2—C1 | 131.8 (7) | N3'—C6'—N1' | 112.3 (5) |
N1—C2—C1 | 118.9 (7) | N3'—C6'—C7' | 99.6 (5) |
C2—C3—C4 | 107.6 (7) | N1'—C6'—C7' | 111.1 (5) |
C2—C3—H3 | 126.2 | N3'—C6'—H6' | 111.1 |
C4—C3—H3 | 126.2 | N1'—C6'—H6' | 111.1 |
C5—C4—C3 | 108.8 (7) | C7'—C6'—H6' | 111.1 |
C5—C4—Br1 | 123.1 (6) | N2'—C7'—N4' | 111.0 (5) |
C3—C4—Br1 | 128.0 (6) | N2'—C7'—C8' | 102.5 (6) |
C4—C5—N1 | 108.3 (6) | N4'—C7'—C8' | 110.1 (6) |
C4—C5—Br2 | 131.7 (6) | N2'—C7'—C6' | 114.5 (6) |
N1—C5—Br2 | 119.5 (6) | N4'—C7'—C6' | 104.7 (5) |
N3—C6—N1 | 112.9 (5) | C8'—C7'—C6' | 114.2 (6) |
N3—C6—C7 | 101.5 (5) | C9'—C8'—C7' | 103.2 (6) |
N1—C6—C7 | 110.4 (5) | C9'—C8'—H8'C | 111.1 |
N3—C6—H6 | 110.6 | C7'—C8'—H8'C | 111.1 |
N1—C6—H6 | 110.6 | C9'—C8'—H8'D | 111.1 |
C7—C6—H6 | 110.6 | C7'—C8'—H8'D | 111.1 |
N2—C7—N4 | 110.4 (5) | H8'C—C8'—H8'D | 109.1 |
N2—C7—C8 | 100.4 (6) | C10'—C9'—C8' | 106.4 (6) |
N4—C7—C8 | 110.4 (6) | C10'—C9'—H9'C | 110.5 |
N2—C7—C6 | 116.4 (6) | C8'—C9'—H9'C | 110.5 |
N4—C7—C6 | 104.4 (5) | C10'—C9'—H9'D | 110.5 |
C8—C7—C6 | 114.9 (6) | C8'—C9'—H9'D | 110.5 |
C7—C8—C9 | 103.9 (6) | H9'C—C9'—H9'D | 108.6 |
C7—C8—H8A | 111.0 | N2'—C10'—C9' | 104.4 (6) |
C9—C8—H8A | 111.0 | N2'—C10'—H10C | 110.9 |
C7—C8—H8B | 111.0 | C9'—C10'—H10C | 110.9 |
C9—C8—H8B | 111.0 | N2'—C10'—H10D | 110.9 |
H8A—C8—H8B | 109.0 | C9'—C10'—H10D | 110.9 |
C10—C9—C8 | 105.4 (6) | H10C—C10'—H10D | 108.9 |
C10—C9—H9A | 110.7 | N4'—C11'—N5' | 126.6 (7) |
C8—C9—H9A | 110.7 | N4'—C11'—N3' | 114.7 (6) |
C10—C9—H9B | 110.7 | N5'—C11'—N3' | 118.6 (6) |
C8—C9—H9B | 110.7 | C12—O2—H2O | 109.5 |
H9A—C9—H9B | 108.8 | O2—C12—H12A | 109.5 |
N2—C10—C9 | 103.6 (6) | O2—C12—H12B | 109.5 |
N2—C10—H10A | 111.0 | H12A—C12—H12B | 109.5 |
C9—C10—H10A | 111.0 | O2—C12—H12C | 109.5 |
N2—C10—H10B | 111.0 | H12A—C12—H12C | 109.5 |
C9—C10—H10B | 111.0 | H12B—C12—H12C | 109.5 |
H10A—C10—H10B | 109.0 | C12'—O2'—H2'O | 109.5 |
N4—C11—N5 | 124.5 (6) | O2'—C12'—H12D | 109.5 |
N4—C11—N3 | 115.2 (6) | O2'—C12'—H12E | 109.5 |
N5—C11—N3 | 120.3 (6) | H12D—C12'—H12E | 109.5 |
C5'—N1'—C2' | 106.3 (6) | O2'—C12'—H12F | 109.5 |
C5'—N1'—C6' | 130.2 (6) | H12D—C12'—H12F | 109.5 |
C2'—N1'—C6' | 123.5 (6) | H12E—C12'—H12F | 109.5 |
C1'—N2'—C7' | 124.6 (6) | C12"—O2"—H2"O | 109.5 |
C1'—N2'—C10' | 124.3 (6) | O2"—C12"—H12G | 109.5 |
C7'—N2'—C10' | 109.4 (6) | O2"—C12"—H12H | 109.5 |
C11'—N3'—C6' | 107.6 (5) | H12G—C12"—H12H | 109.5 |
C11'—N3'—H3N' | 131 (4) | O2"—C12"—H12I | 109.5 |
C6'—N3'—H3N' | 117 (4) | H12G—C12"—H12I | 109.5 |
C11'—N4'—C7' | 106.3 (6) | H12H—C12"—H12I | 109.5 |
C11'—N5'—H5'C | 120.0 | ||
C7—N2—C1—O1 | 166.6 (7) | C7'—N2'—C1'—O1' | 164.6 (7) |
C10—N2—C1—O1 | 1.9 (12) | C10'—N2'—C1'—O1' | 1.4 (12) |
C7—N2—C1—C2 | −19.0 (11) | C7'—N2'—C1'—C2' | −20.5 (10) |
C10—N2—C1—C2 | 176.3 (7) | C10'—N2'—C1'—C2' | 176.2 (7) |
C5—N1—C2—C3 | 0.1 (8) | C5'—N1'—C2'—C3' | 0.3 (7) |
C6—N1—C2—C3 | −170.8 (6) | C6'—N1'—C2'—C3' | −177.6 (6) |
C5—N1—C2—C1 | −173.0 (6) | C5'—N1'—C2'—C1' | −173.0 (6) |
C6—N1—C2—C1 | 16.1 (10) | C6'—N1'—C2'—C1' | 9.1 (9) |
O1—C1—C2—C3 | −4.5 (14) | O1'—C1'—C2'—C3' | −1.0 (13) |
N2—C1—C2—C3 | −179.0 (8) | N2'—C1'—C2'—C3' | −175.8 (7) |
O1—C1—C2—N1 | 166.7 (7) | O1'—C1'—C2'—N1' | 170.8 (7) |
N2—C1—C2—N1 | −7.7 (10) | N2'—C1'—C2'—N1' | −4.0 (10) |
N1—C2—C3—C4 | −0.7 (9) | N1'—C2'—C3'—C4' | 1.0 (8) |
C1—C2—C3—C4 | 171.2 (8) | C1'—C2'—C3'—C4' | 173.6 (7) |
C2—C3—C4—C5 | 1.0 (9) | C2'—C3'—C4'—C5' | −1.9 (8) |
C2—C3—C4—Br1 | −180.0 (6) | C2'—C3'—C4'—Br2' | 179.1 (5) |
C3—C4—C5—N1 | −1.0 (8) | C2'—N1'—C5'—C4' | −1.5 (7) |
Br1—C4—C5—N1 | 179.9 (4) | C6'—N1'—C5'—C4' | 176.2 (6) |
C3—C4—C5—Br2 | −172.8 (6) | C2'—N1'—C5'—Br1' | 177.5 (5) |
Br1—C4—C5—Br2 | 8.2 (10) | C6'—N1'—C5'—Br1' | −4.7 (9) |
C2—N1—C5—C4 | 0.6 (8) | C3'—C4'—C5'—N1' | 2.1 (8) |
C6—N1—C5—C4 | 171.0 (6) | Br2'—C4'—C5'—N1' | −178.8 (5) |
C2—N1—C5—Br2 | 173.5 (5) | C3'—C4'—C5'—Br1' | −176.8 (5) |
C6—N1—C5—Br2 | −16.0 (9) | Br2'—C4'—C5'—Br1' | 2.3 (10) |
C11—N3—C6—N1 | −94.3 (6) | C11'—N3'—C6'—N1' | −93.3 (7) |
C11—N3—C6—C7 | 23.9 (7) | C11'—N3'—C6'—C7' | 24.4 (7) |
C2—N1—C6—N3 | 114.2 (7) | C5'—N1'—C6'—N3' | −59.1 (9) |
C5—N1—C6—N3 | −54.7 (8) | C2'—N1'—C6'—N3' | 118.4 (6) |
C2—N1—C6—C7 | 1.3 (8) | C5'—N1'—C6'—C7' | −169.6 (6) |
C5—N1—C6—C7 | −167.5 (6) | C2'—N1'—C6'—C7' | 7.8 (8) |
C1—N2—C7—N4 | −81.8 (8) | C1'—N2'—C7'—N4' | −80.5 (8) |
C10—N2—C7—N4 | 84.4 (7) | C10'—N2'—C7'—N4' | 84.9 (6) |
C1—N2—C7—C8 | 161.7 (7) | C1'—N2'—C7'—C8' | 162.0 (7) |
C10—N2—C7—C8 | −32.1 (8) | C10'—N2'—C7'—C8' | −32.7 (8) |
C1—N2—C7—C6 | 37.0 (10) | C1'—N2'—C7'—C6' | 37.7 (10) |
C10—N2—C7—C6 | −156.8 (6) | C10'—N2'—C7'—C6' | −156.9 (6) |
C11—N4—C7—N2 | 141.5 (6) | C11'—N4'—C7'—N2' | 141.7 (6) |
C11—N4—C7—C8 | −108.4 (6) | C11'—N4'—C7'—C8' | −105.5 (7) |
C11—N4—C7—C6 | 15.6 (7) | C11'—N4'—C7'—C6' | 17.7 (7) |
N3—C6—C7—N2 | −146.0 (6) | N3'—C6'—C7'—N2' | −146.8 (6) |
N1—C6—C7—N2 | −26.0 (8) | N1'—C6'—C7'—N2' | −28.3 (8) |
N3—C6—C7—N4 | −24.0 (6) | N3'—C6'—C7'—N4' | −25.1 (6) |
N1—C6—C7—N4 | 96.0 (6) | N1'—C6'—C7'—N4' | 93.4 (6) |
N3—C6—C7—C8 | 97.0 (7) | N3'—C6'—C7'—C8' | 95.4 (7) |
N1—C6—C7—C8 | −143.0 (6) | N1'—C6'—C7'—C8' | −146.1 (6) |
N2—C7—C8—C9 | 36.8 (8) | N2'—C7'—C8'—C9' | 37.5 (8) |
N4—C7—C8—C9 | −79.8 (7) | N4'—C7'—C8'—C9' | −80.6 (7) |
C6—C7—C8—C9 | 162.6 (6) | C6'—C7'—C8'—C9' | 161.9 (6) |
C7—C8—C9—C10 | −30.3 (8) | C7'—C8'—C9'—C10' | −29.2 (8) |
C1—N2—C10—C9 | 179.5 (7) | C1'—N2'—C10'—C9' | −179.8 (7) |
C7—N2—C10—C9 | 13.5 (8) | C7'—N2'—C10'—C9' | 14.7 (8) |
C8—C9—C10—N2 | 11.0 (7) | C8'—C9'—C10'—N2' | 9.9 (8) |
C7—N4—C11—N5 | 178.4 (6) | C7'—N4'—C11'—N5' | 178.4 (7) |
C7—N4—C11—N3 | −0.5 (8) | C7'—N4'—C11'—N3' | −2.1 (8) |
C6—N3—C11—N4 | −16.2 (8) | C6'—N3'—C11'—N4' | −15.7 (8) |
C6—N3—C11—N5 | 164.9 (6) | C6'—N3'—C11'—N5' | 163.9 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O1i | 0.86 (1) | 2.14 (3) | 2.921 (7) | 151 (4) |
N5—H5BN···O1i | 0.86 | 2.36 | 3.096 (7) | 143 |
N5—H5AN···N4′ii | 0.86 | 2.13 | 2.981 (8) | 171 |
N3′—H3N′···O1′iii | 0.86 (1) | 2.13 (3) | 2.833 (7) | 139 (5) |
N5′—H5′D···O1′iii | 0.86 | 2.34 | 3.062 (7) | 142 |
N5′—H5′C···N4iv | 0.86 | 2.12 | 2.961 (7) | 167 |
Symmetry codes: (i) x, y, z+1; (ii) −x+1, y+1/2, −z+1; (iii) x−1, y, z; (iv) −x+1, y−1/2, −z+1. |
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