In the asymmetric unit of the structure of the solvate of bis(benzimidazol-2-yl-methyl)amine (IDB), 2C
16H
15N
5·C
2H
6O·2H
2O, there are two molecules of IDB, two uncoordinated water molecules and one ethanol solvent molecule. In the crystal structure, IDB, water and ethanol molecules are connected into a three-dimensional network
via intermolecular N—H
O, O—H
N, O—H
O and C—H
π(arene) interactions.
Supporting information
CCDC reference: 621407
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.059
- wR factor = 0.167
- Data-to-parameter ratio = 14.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D H5A .. H2C .. 1.47 Ang.
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc.
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 17.00 Perc.
PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C33 - C34 ... 1.40 Ang.
PLAT416_ALERT_2_C Short Intra D-H..H-D H8 .. H6' .. 1.99 Ang.
PLAT416_ALERT_2_C Short Intra D-H..H-D H10 .. H6' .. 1.93 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor >N6 - >H6A ... ?
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
Bis(benzimidazol-2-yl-methyl)amine–ethanol–water (2/2/1)
top
Crystal data top
2C16H15N5·C2H6O·2H2O | Z = 2 |
Mr = 636.76 | F(000) = 676 |
Triclinic, P1 | Dx = 1.265 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.6345 (8) Å | Cell parameters from 3450 reflections |
b = 14.0418 (13) Å | θ = 2.4–21.2° |
c = 14.2810 (13) Å | µ = 0.09 mm−1 |
α = 92.724 (2)° | T = 292 K |
β = 104.845 (2)° | Block, colorless |
γ = 90.376 (2)° | 0.30 × 0.20 × 0.20 mm |
V = 1671.5 (3) Å3 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 4258 reflections with I > 2σ(I) |
Radiation source: fine focus sealed Siemens Mo tube | Rint = 0.026 |
Graphite monochromator | θmax = 27.0°, θmin = 2.0° |
ω scans | h = −10→11 |
14144 measured reflections | k = −17→17 |
7160 independent reflections | l = −18→18 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.167 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0783P)2] where P = (Fo2 + 2Fc2)/3 |
7160 reflections | (Δ/σ)max < 0.001 |
509 parameters | Δρmax = 0.25 e Å−3 |
43 restraints | Δρmin = −0.22 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.7417 (3) | 0.14850 (17) | 0.22238 (15) | 0.0724 (7) | |
H1A | 0.6310 | 0.1674 | 0.2125 | 0.087* | 0.72 |
H1B | 0.7619 | 0.0974 | 0.2670 | 0.087* | 0.72 |
H1C | 0.7898 | 0.0938 | 0.2570 | 0.087* | 0.28 |
H1D | 0.6455 | 0.1616 | 0.2436 | 0.087* | 0.28 |
C2 | 0.8515 (2) | 0.23024 (15) | 0.26044 (14) | 0.0539 (5) | |
C3 | 1.0006 (2) | 0.33418 (16) | 0.36639 (14) | 0.0543 (5) | |
C4 | 1.0809 (3) | 0.39114 (19) | 0.44596 (16) | 0.0711 (7) | |
H4 | 1.0609 | 0.3859 | 0.5065 | 0.085* | |
C5 | 1.1912 (3) | 0.4554 (2) | 0.43150 (18) | 0.0819 (8) | |
H5 | 1.2465 | 0.4954 | 0.4832 | 0.098* | |
C6 | 1.2225 (3) | 0.46250 (19) | 0.34129 (18) | 0.0789 (7) | |
H6 | 1.2997 | 0.5062 | 0.3344 | 0.095* | |
C7 | 1.1426 (3) | 0.40674 (17) | 0.26260 (17) | 0.0673 (6) | |
H7 | 1.1641 | 0.4121 | 0.2025 | 0.081* | |
C8 | 1.0286 (2) | 0.34183 (15) | 0.27497 (14) | 0.0539 (5) | |
C10 | 0.7484 (3) | 0.00437 (18) | −0.00260 (17) | 0.0627 (6) | |
C11 | 0.7633 (2) | −0.06785 (16) | −0.13562 (17) | 0.0588 (6) | |
C12 | 0.7568 (3) | −0.13255 (17) | −0.21366 (19) | 0.0707 (7) | |
H12 | 0.7181 | −0.1945 | −0.2140 | 0.085* | |
C13 | 0.8095 (3) | −0.1017 (2) | −0.28977 (19) | 0.0774 (7) | |
H13 | 0.8068 | −0.1438 | −0.3424 | 0.093* | |
C14 | 0.8661 (3) | −0.0101 (2) | −0.29050 (18) | 0.0805 (7) | |
H14 | 0.9005 | 0.0084 | −0.3437 | 0.097* | |
C15 | 0.8731 (3) | 0.05477 (18) | −0.21423 (17) | 0.0715 (7) | |
H15 | 0.9113 | 0.1168 | −0.2148 | 0.086* | |
C16 | 0.8213 (2) | 0.02433 (16) | −0.13708 (15) | 0.0564 (5) | |
C17 | 0.1471 (3) | 0.46105 (17) | 0.92162 (15) | 0.0677 (6) | |
H17A | 0.0459 | 0.4898 | 0.9231 | 0.081* | 0.74 |
H17B | 0.1839 | 0.4887 | 0.8700 | 0.081* | 0.74 |
H17C | 0.0398 | 0.4657 | 0.9307 | 0.081* | 0.26 |
H17D | 0.1583 | 0.5075 | 0.8756 | 0.081* | 0.26 |
C18 | 0.2665 (2) | 0.48370 (15) | 1.01603 (14) | 0.0527 (5) | |
C19 | 0.4034 (2) | 0.55541 (15) | 1.14720 (14) | 0.0493 (5) | |
C20 | 0.4680 (3) | 0.61874 (16) | 1.22505 (15) | 0.0596 (6) | |
H20 | 0.4264 | 0.6793 | 1.2287 | 0.072* | |
C21 | 0.5945 (3) | 0.58980 (18) | 1.29634 (16) | 0.0676 (6) | |
H21 | 0.6398 | 0.6314 | 1.3490 | 0.081* | |
C22 | 0.6563 (3) | 0.4993 (2) | 1.29136 (16) | 0.0738 (7) | |
H22 | 0.7422 | 0.4816 | 1.3410 | 0.089* | |
C23 | 0.5947 (3) | 0.43566 (17) | 1.21587 (16) | 0.0667 (6) | |
H23 | 0.6365 | 0.3750 | 1.2132 | 0.080* | |
C24 | 0.4677 (2) | 0.46493 (15) | 1.14340 (14) | 0.0506 (5) | |
C25 | 0.0368 (3) | 0.33708 (19) | 0.80046 (17) | 0.0846 (8) | |
H25A | 0.0286 | 0.3943 | 0.7641 | 0.102* | 0.74 |
H25B | −0.0712 | 0.3161 | 0.7987 | 0.102* | 0.74 |
H25C | 0.0033 | 0.3896 | 0.7586 | 0.102* | 0.26 |
H25D | −0.0551 | 0.3122 | 0.8196 | 0.102* | 0.26 |
C26 | 0.1127 (3) | 0.26168 (16) | 0.75121 (15) | 0.0603 (6) | |
C27 | 0.1663 (3) | 0.16088 (16) | 0.64759 (14) | 0.0577 (6) | |
C28 | 0.1658 (3) | 0.10062 (19) | 0.56704 (16) | 0.0763 (7) | |
H28 | 0.0804 | 0.0992 | 0.5119 | 0.092* | |
C29 | 0.2961 (3) | 0.0434 (2) | 0.57182 (19) | 0.0823 (8) | |
H29 | 0.2986 | 0.0025 | 0.5190 | 0.099* | |
C30 | 0.4235 (3) | 0.04543 (19) | 0.6538 (2) | 0.0786 (7) | |
H30 | 0.5103 | 0.0064 | 0.6543 | 0.094* | |
C31 | 0.4255 (3) | 0.10314 (17) | 0.73403 (17) | 0.0683 (6) | |
H31 | 0.5114 | 0.1039 | 0.7889 | 0.082* | |
C32 | 0.2941 (3) | 0.16034 (15) | 0.72993 (15) | 0.0555 (5) | |
C33 | 0.5105 (4) | 0.2601 (3) | 0.4599 (3) | 0.1641 (18) | |
H33A | 0.5366 | 0.3104 | 0.4230 | 0.246* | |
H33B | 0.4179 | 0.2770 | 0.4821 | 0.246* | |
H33C | 0.4883 | 0.2023 | 0.4198 | 0.246* | |
C34 | 0.6403 (4) | 0.2464 (3) | 0.5399 (2) | 0.1221 (12) | |
H34A | 0.6591 | 0.3044 | 0.5813 | 0.147* | |
H34B | 0.6123 | 0.1960 | 0.5771 | 0.147* | |
O3 | 0.7805 (2) | 0.22288 (18) | 0.51491 (11) | 0.1016 (7) | |
H3 | 0.856 (3) | 0.224 (3) | 0.5647 (16) | 0.152* | |
C9 | 0.7059 (4) | 0.0236 (3) | 0.0915 (3) | 0.0543 (11) | 0.72 |
H9A | 0.5905 | 0.0236 | 0.0815 | 0.065* | 0.72 |
H9B | 0.7501 | −0.0246 | 0.1367 | 0.065* | 0.72 |
N1 | 0.7752 (5) | 0.1175 (3) | 0.1285 (3) | 0.0685 (11) | 0.72 |
H1 | 0.8752 (16) | 0.122 (3) | 0.130 (2) | 0.082* | 0.72 |
N1' | 0.6810 (12) | 0.1156 (7) | 0.1233 (6) | 0.079 (3) | 0.28 |
H1' | 0.758 (11) | 0.150 (5) | 0.114 (7) | 0.094* | 0.28 |
N2 | 0.8873 (2) | 0.26188 (14) | 0.35446 (12) | 0.0572 (5) | |
H2 | 0.842 (2) | 0.2459 (15) | 0.3987 (12) | 0.069* | |
N3 | 0.9316 (2) | 0.27621 (13) | 0.20946 (11) | 0.0573 (5) | |
N4 | 0.7182 (2) | −0.07883 (14) | −0.04992 (15) | 0.0691 (5) | |
N5 | 0.8105 (2) | 0.06918 (13) | −0.05078 (13) | 0.0611 (5) | |
H5A | 0.834 (3) | 0.1274 (8) | −0.0344 (16) | 0.073* | |
N6 | 0.1224 (5) | 0.3611 (3) | 0.9010 (3) | 0.0658 (11) | 0.74 |
H6A | 0.066 (4) | 0.349 (2) | 0.941 (2) | 0.079* | 0.74 |
C9' | 0.7750 (13) | 0.0377 (10) | 0.1036 (6) | 0.071 (3) | 0.28 |
H9C | 0.7536 | −0.0159 | 0.1391 | 0.086* | 0.28 |
H9D | 0.8871 | 0.0555 | 0.1290 | 0.086* | 0.28 |
N6' | 0.1751 (17) | 0.3730 (10) | 0.8758 (9) | 0.084 (4) | 0.26 |
H6' | 0.201 (9) | 0.326 (6) | 0.926 (7) | 0.101* | 0.26 |
N7 | 0.2762 (2) | 0.56541 (12) | 1.06636 (12) | 0.0551 (4) | |
N8 | 0.3773 (2) | 0.42056 (13) | 1.05850 (12) | 0.0569 (5) | |
H8 | 0.389 (3) | 0.3632 (9) | 1.0350 (15) | 0.068* | |
N9 | 0.0531 (2) | 0.22579 (14) | 0.66325 (12) | 0.0626 (5) | |
N10 | 0.2550 (2) | 0.22472 (13) | 0.79521 (12) | 0.0596 (5) | |
H10 | 0.308 (2) | 0.2417 (15) | 0.8538 (9) | 0.072* | |
O1 | 0.4575 (2) | 0.23062 (11) | 0.99904 (13) | 0.0745 (5) | |
H1E | 0.400 (2) | 0.1872 (15) | 1.010 (2) | 0.112* | |
H1F | 0.5547 (12) | 0.2190 (18) | 1.0184 (19) | 0.112* | |
O2 | 0.1024 (4) | 0.7317 (2) | 0.99682 (19) | 0.0689 (7) | 0.79 |
H2A | 0.147 (5) | 0.6839 (17) | 1.0226 (19) | 0.103* | 0.79 |
H2B | 0.097 (4) | 0.731 (2) | 0.9374 (9) | 0.103* | 0.79 |
O2' | 0.2037 (14) | 0.7402 (8) | 0.9979 (8) | 0.071 (3) | 0.21 |
H2C | 0.137 (15) | 0.769 (8) | 1.020 (11) | 0.106* | 0.21 |
H2D | 0.224 (16) | 0.687 (4) | 1.018 (9) | 0.106* | 0.21 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0939 (18) | 0.0724 (16) | 0.0489 (13) | −0.0093 (14) | 0.0159 (12) | −0.0020 (11) |
C2 | 0.0577 (13) | 0.0615 (14) | 0.0432 (11) | 0.0091 (11) | 0.0140 (10) | 0.0020 (10) |
C3 | 0.0518 (12) | 0.0655 (14) | 0.0459 (12) | 0.0068 (11) | 0.0132 (9) | 0.0019 (10) |
C4 | 0.0729 (15) | 0.0894 (18) | 0.0503 (13) | −0.0021 (14) | 0.0159 (12) | −0.0018 (12) |
C5 | 0.0842 (18) | 0.091 (2) | 0.0627 (16) | −0.0149 (16) | 0.0066 (13) | −0.0033 (14) |
C6 | 0.0741 (17) | 0.0871 (19) | 0.0743 (17) | −0.0142 (14) | 0.0157 (14) | 0.0133 (14) |
C7 | 0.0698 (15) | 0.0779 (17) | 0.0577 (14) | 0.0045 (13) | 0.0206 (12) | 0.0150 (12) |
C8 | 0.0579 (13) | 0.0611 (14) | 0.0429 (11) | 0.0129 (11) | 0.0120 (10) | 0.0071 (10) |
C10 | 0.0641 (14) | 0.0620 (15) | 0.0648 (14) | 0.0108 (12) | 0.0211 (11) | 0.0066 (12) |
C11 | 0.0466 (12) | 0.0613 (15) | 0.0678 (14) | 0.0078 (10) | 0.0143 (10) | −0.0015 (12) |
C12 | 0.0559 (14) | 0.0607 (15) | 0.0893 (18) | 0.0049 (11) | 0.0104 (13) | −0.0141 (14) |
C13 | 0.0628 (15) | 0.092 (2) | 0.0726 (17) | 0.0099 (14) | 0.0127 (13) | −0.0212 (15) |
C14 | 0.0785 (17) | 0.100 (2) | 0.0637 (16) | 0.0028 (16) | 0.0209 (13) | −0.0094 (15) |
C15 | 0.0779 (16) | 0.0708 (16) | 0.0659 (15) | −0.0071 (13) | 0.0205 (13) | −0.0038 (13) |
C16 | 0.0529 (12) | 0.0583 (14) | 0.0553 (13) | 0.0042 (10) | 0.0103 (10) | −0.0050 (11) |
C17 | 0.0680 (15) | 0.0756 (17) | 0.0528 (13) | −0.0087 (12) | 0.0046 (11) | −0.0034 (12) |
C18 | 0.0498 (12) | 0.0585 (13) | 0.0497 (12) | −0.0004 (10) | 0.0129 (9) | 0.0013 (10) |
C19 | 0.0480 (11) | 0.0541 (13) | 0.0464 (11) | −0.0040 (10) | 0.0137 (9) | 0.0012 (9) |
C20 | 0.0624 (13) | 0.0565 (14) | 0.0587 (13) | −0.0078 (11) | 0.0152 (11) | −0.0074 (11) |
C21 | 0.0637 (14) | 0.0823 (18) | 0.0519 (13) | −0.0124 (13) | 0.0082 (11) | −0.0085 (12) |
C22 | 0.0633 (15) | 0.099 (2) | 0.0526 (14) | 0.0060 (14) | 0.0038 (11) | 0.0050 (13) |
C23 | 0.0642 (14) | 0.0709 (15) | 0.0619 (14) | 0.0142 (12) | 0.0105 (11) | 0.0040 (12) |
C24 | 0.0502 (12) | 0.0540 (13) | 0.0482 (11) | 0.0010 (10) | 0.0145 (9) | −0.0019 (9) |
C25 | 0.0798 (17) | 0.0837 (18) | 0.0733 (16) | 0.0126 (14) | −0.0055 (13) | −0.0299 (14) |
C26 | 0.0620 (14) | 0.0597 (14) | 0.0520 (13) | −0.0031 (11) | 0.0034 (11) | −0.0062 (10) |
C27 | 0.0581 (13) | 0.0634 (14) | 0.0495 (12) | −0.0062 (11) | 0.0111 (10) | −0.0020 (10) |
C28 | 0.0784 (17) | 0.0942 (19) | 0.0520 (14) | −0.0003 (15) | 0.0118 (12) | −0.0106 (13) |
C29 | 0.092 (2) | 0.0873 (19) | 0.0720 (17) | 0.0051 (16) | 0.0306 (15) | −0.0084 (14) |
C30 | 0.0759 (17) | 0.0788 (18) | 0.0883 (19) | 0.0106 (14) | 0.0336 (15) | 0.0053 (15) |
C31 | 0.0611 (14) | 0.0718 (16) | 0.0687 (15) | 0.0015 (12) | 0.0101 (12) | 0.0079 (13) |
C32 | 0.0576 (13) | 0.0548 (13) | 0.0523 (12) | −0.0079 (11) | 0.0112 (10) | 0.0015 (10) |
C33 | 0.074 (2) | 0.222 (5) | 0.186 (4) | 0.023 (3) | 0.015 (3) | 0.002 (4) |
C34 | 0.076 (2) | 0.193 (4) | 0.101 (2) | 0.001 (2) | 0.0325 (19) | 0.001 (2) |
O3 | 0.0570 (11) | 0.200 (2) | 0.0485 (10) | 0.0021 (12) | 0.0141 (8) | 0.0075 (12) |
C9 | 0.046 (2) | 0.058 (2) | 0.0602 (19) | −0.006 (2) | 0.0167 (18) | 0.0037 (15) |
N1 | 0.069 (2) | 0.085 (2) | 0.0529 (17) | −0.035 (3) | 0.025 (2) | −0.0180 (17) |
N1' | 0.087 (6) | 0.080 (5) | 0.064 (5) | 0.007 (6) | 0.011 (5) | −0.001 (4) |
N2 | 0.0596 (11) | 0.0748 (13) | 0.0414 (10) | 0.0014 (10) | 0.0206 (8) | 0.0033 (9) |
N3 | 0.0684 (12) | 0.0632 (12) | 0.0416 (9) | 0.0097 (9) | 0.0163 (9) | 0.0036 (8) |
N4 | 0.0693 (12) | 0.0603 (13) | 0.0808 (14) | 0.0053 (10) | 0.0250 (11) | 0.0026 (11) |
N5 | 0.0716 (12) | 0.0543 (11) | 0.0567 (11) | 0.0000 (10) | 0.0165 (9) | −0.0054 (10) |
N6 | 0.072 (3) | 0.071 (2) | 0.048 (2) | 0.0085 (17) | 0.0056 (16) | −0.0206 (18) |
C9' | 0.058 (7) | 0.072 (7) | 0.095 (7) | 0.001 (6) | 0.038 (6) | 0.014 (5) |
N6' | 0.094 (8) | 0.104 (7) | 0.042 (6) | 0.032 (6) | 0.001 (5) | −0.027 (5) |
N7 | 0.0567 (10) | 0.0528 (11) | 0.0524 (10) | 0.0019 (8) | 0.0084 (8) | −0.0010 (8) |
N8 | 0.0627 (11) | 0.0510 (11) | 0.0551 (11) | 0.0035 (9) | 0.0134 (9) | −0.0083 (9) |
N9 | 0.0606 (11) | 0.0733 (13) | 0.0480 (10) | −0.0008 (10) | 0.0052 (8) | −0.0087 (9) |
N10 | 0.0600 (11) | 0.0609 (12) | 0.0492 (10) | −0.0037 (9) | −0.0001 (9) | −0.0070 (9) |
O1 | 0.0732 (11) | 0.0650 (11) | 0.0787 (11) | 0.0020 (9) | 0.0088 (10) | −0.0030 (9) |
O2 | 0.108 (2) | 0.0499 (15) | 0.0483 (13) | 0.0081 (17) | 0.0188 (16) | 0.0026 (10) |
O2' | 0.084 (7) | 0.053 (6) | 0.067 (6) | −0.005 (6) | 0.003 (6) | 0.003 (4) |
Geometric parameters (Å, º) top
C1—N1' | 1.430 (8) | C24—N8 | 1.380 (2) |
C1—C2 | 1.475 (3) | C25—N6' | 1.456 (11) |
C1—N1 | 1.489 (4) | C25—N6 | 1.458 (4) |
C1—H1A | 0.9700 | C25—C26 | 1.490 (3) |
C1—H1B | 0.9700 | C25—H25A | 0.9700 |
C1—H1C | 0.9700 | C25—H25B | 0.9700 |
C1—H1D | 0.9700 | C25—H25C | 0.9695 |
C2—N3 | 1.312 (2) | C25—H25D | 0.9713 |
C2—N2 | 1.351 (2) | C26—N9 | 1.305 (2) |
C3—N2 | 1.379 (3) | C26—N10 | 1.348 (3) |
C3—C4 | 1.384 (3) | C27—C32 | 1.392 (3) |
C3—C8 | 1.396 (3) | C27—N9 | 1.393 (3) |
C4—C5 | 1.368 (3) | C27—C28 | 1.394 (3) |
C4—H4 | 0.9300 | C28—C29 | 1.376 (3) |
C5—C6 | 1.390 (3) | C28—H28 | 0.9300 |
C5—H5 | 0.9300 | C29—C30 | 1.385 (3) |
C6—C7 | 1.365 (3) | C29—H29 | 0.9300 |
C6—H6 | 0.9300 | C30—C31 | 1.368 (3) |
C7—C8 | 1.387 (3) | C30—H30 | 0.9300 |
C7—H7 | 0.9300 | C31—C32 | 1.386 (3) |
C8—N3 | 1.390 (3) | C31—H31 | 0.9300 |
C10—N4 | 1.312 (3) | C32—N10 | 1.373 (3) |
C10—N5 | 1.353 (3) | C33—C34 | 1.402 (4) |
C10—C9 | 1.494 (4) | C33—H33A | 0.9600 |
C10—C9' | 1.525 (8) | C33—H33B | 0.9600 |
C11—C16 | 1.388 (3) | C33—H33C | 0.9600 |
C11—N4 | 1.391 (3) | C34—O3 | 1.385 (3) |
C11—C12 | 1.393 (3) | C34—H34A | 0.9700 |
C12—C13 | 1.368 (3) | C34—H34B | 0.9700 |
C12—H12 | 0.9300 | O3—H3 | 0.831 (10) |
C13—C14 | 1.375 (4) | C9—N1 | 1.461 (5) |
C13—H13 | 0.9300 | C9—H9A | 0.9700 |
C14—C15 | 1.375 (3) | C9—H9B | 0.9700 |
C14—H14 | 0.9300 | N1—H1 | 0.862 (10) |
C15—C16 | 1.375 (3) | N1—H1' | 0.52 (12) |
C15—H15 | 0.9300 | N1'—C9' | 1.426 (10) |
C16—N5 | 1.382 (3) | N1'—H1' | 0.861 (10) |
C17—N6' | 1.422 (11) | N2—H2 | 0.860 (9) |
C17—N6 | 1.423 (4) | N5—H5A | 0.847 (10) |
C17—C18 | 1.492 (3) | N6—H6A | 0.86 (3) |
C17—H17A | 0.9700 | N6—H6' | 0.860 (10) |
C17—H17B | 0.9700 | C9'—H9C | 0.9700 |
C17—H17C | 0.9700 | C9'—H9D | 0.9700 |
C17—H17D | 0.9700 | N6'—H6' | 0.99 (8) |
C18—N7 | 1.315 (2) | N8—H8 | 0.874 (9) |
C18—N8 | 1.354 (3) | N10—H10 | 0.864 (9) |
C19—C20 | 1.386 (3) | O1—H1E | 0.833 (10) |
C19—N7 | 1.388 (2) | O1—H1F | 0.834 (10) |
C19—C24 | 1.394 (3) | O2—H2A | 0.830 (10) |
C20—C21 | 1.368 (3) | O2—H2B | 0.836 (10) |
C20—H20 | 0.9300 | O2—H2C | 0.64 (16) |
C21—C22 | 1.387 (3) | O2—H2D | 1.21 (10) |
C21—H21 | 0.9300 | O2'—H2A | 1.05 (3) |
C22—C23 | 1.361 (3) | O2'—H2B | 1.09 (3) |
C22—H22 | 0.9300 | O2'—H2C | 0.822 (10) |
C23—C24 | 1.381 (3) | O2'—H2D | 0.823 (10) |
C23—H23 | 0.9300 | | |
| | | |
N1'—C1—C2 | 127.5 (5) | N6—C25—H25B | 108.6 |
C2—C1—N1 | 105.4 (2) | C26—C25—H25B | 108.6 |
N1'—C1—H1A | 80.6 | H25A—C25—H25B | 107.6 |
C2—C1—H1A | 110.7 | N6'—C25—H25C | 105.7 |
N1—C1—H1A | 110.7 | N6—C25—H25C | 117.2 |
N1'—C1—H1B | 113.3 | C26—C25—H25C | 110.8 |
C2—C1—H1B | 110.7 | H25B—C25—H25C | 94.9 |
N1—C1—H1B | 110.7 | N6'—C25—H25D | 118.6 |
H1A—C1—H1B | 108.8 | N6—C25—H25D | 91.9 |
N1'—C1—H1C | 106.2 | C26—C25—H25D | 111.6 |
C2—C1—H1C | 106.3 | H25A—C25—H25D | 120.8 |
N1—C1—H1C | 95.5 | H25C—C25—H25D | 109.1 |
H1A—C1—H1C | 125.9 | N9—C26—N10 | 113.3 (2) |
N1'—C1—H1D | 103.4 | N9—C26—C25 | 125.1 (2) |
C2—C1—H1D | 105.6 | N10—C26—C25 | 121.63 (19) |
N1—C1—H1D | 134.9 | C32—C27—N9 | 109.55 (18) |
H1B—C1—H1D | 87.7 | C32—C27—C28 | 120.0 (2) |
H1C—C1—H1D | 106.2 | N9—C27—C28 | 130.4 (2) |
N3—C2—N2 | 112.79 (19) | C29—C28—C27 | 117.8 (2) |
N3—C2—C1 | 124.48 (19) | C29—C28—H28 | 121.1 |
N2—C2—C1 | 122.6 (2) | C27—C28—H28 | 121.1 |
N2—C3—C4 | 132.9 (2) | C28—C29—C30 | 121.2 (2) |
N2—C3—C8 | 105.03 (18) | C28—C29—H29 | 119.4 |
C4—C3—C8 | 122.1 (2) | C30—C29—H29 | 119.4 |
C5—C4—C3 | 116.9 (2) | C31—C30—C29 | 122.0 (2) |
C5—C4—H4 | 121.5 | C31—C30—H30 | 119.0 |
C3—C4—H4 | 121.5 | C29—C30—H30 | 119.0 |
C4—C5—C6 | 121.6 (2) | C30—C31—C32 | 117.1 (2) |
C4—C5—H5 | 119.2 | C30—C31—H31 | 121.5 |
C6—C5—H5 | 119.2 | C32—C31—H31 | 121.5 |
C7—C6—C5 | 121.6 (2) | N10—C32—C31 | 133.0 (2) |
C7—C6—H6 | 119.2 | N10—C32—C27 | 105.12 (19) |
C5—C6—H6 | 119.2 | C31—C32—C27 | 121.9 (2) |
C6—C7—C8 | 118.1 (2) | C34—C33—H33A | 109.5 |
C6—C7—H7 | 121.0 | C34—C33—H33B | 109.5 |
C8—C7—H7 | 121.0 | H33A—C33—H33B | 109.5 |
C7—C8—N3 | 130.69 (19) | C34—C33—H33C | 109.5 |
C7—C8—C3 | 119.8 (2) | H33A—C33—H33C | 109.5 |
N3—C8—C3 | 109.50 (19) | H33B—C33—H33C | 109.5 |
N4—C10—N5 | 113.0 (2) | O3—C34—C33 | 113.6 (3) |
N4—C10—C9 | 121.4 (3) | O3—C34—H34A | 108.8 |
N5—C10—C9 | 125.4 (3) | C33—C34—H34A | 108.8 |
N4—C10—C9' | 134.0 (6) | O3—C34—H34B | 108.8 |
N5—C10—C9' | 110.3 (6) | C33—C34—H34B | 108.8 |
C16—C11—N4 | 109.7 (2) | H34A—C34—H34B | 107.7 |
C16—C11—C12 | 120.0 (2) | C34—O3—H3 | 109 (3) |
N4—C11—C12 | 130.3 (2) | N1—C9—C10 | 106.0 (3) |
C13—C12—C11 | 117.7 (2) | N1—C9—H9A | 110.5 |
C13—C12—H12 | 121.2 | C10—C9—H9A | 110.5 |
C11—C12—H12 | 121.2 | N1—C9—H9B | 110.5 |
C12—C13—C14 | 121.8 (2) | C10—C9—H9B | 110.5 |
C12—C13—H13 | 119.1 | H9A—C9—H9B | 108.7 |
C14—C13—H13 | 119.1 | C9—N1—C1 | 113.0 (3) |
C15—C14—C13 | 121.3 (3) | C9—N1—H1 | 113 (2) |
C15—C14—H14 | 119.3 | C1—N1—H1 | 113 (2) |
C13—C14—H14 | 119.3 | C9—N1—H1' | 127 (9) |
C14—C15—C16 | 117.4 (2) | C1—N1—H1' | 92 (4) |
C14—C15—H15 | 121.3 | H1—N1—H1' | 97 (6) |
C16—C15—H15 | 121.3 | C9'—N1'—C1 | 108.7 (8) |
C15—C16—N5 | 132.8 (2) | C9'—N1'—H1' | 84 (6) |
C15—C16—C11 | 121.8 (2) | C1—N1'—H1' | 84 (6) |
N5—C16—C11 | 105.4 (2) | C2—N2—C3 | 107.46 (17) |
N6'—C17—C18 | 113.3 (7) | C2—N2—H2 | 128.0 (15) |
N6—C17—C18 | 112.4 (3) | C3—N2—H2 | 124.2 (15) |
N6'—C17—H17A | 128.9 | C2—N3—C8 | 105.21 (16) |
N6—C17—H17A | 109.1 | C10—N4—C11 | 105.0 (2) |
C18—C17—H17A | 109.1 | C10—N5—C16 | 106.94 (18) |
N6'—C17—H17B | 83.8 | C10—N5—H5A | 128.0 (16) |
N6—C17—H17B | 109.1 | C16—N5—H5A | 125.0 (16) |
C18—C17—H17B | 109.1 | C17—N6—C25 | 113.0 (4) |
H17A—C17—H17B | 107.9 | C17—N6—H6A | 100 (2) |
N6'—C17—H17C | 113.5 | C25—N6—H6A | 112 (2) |
N6—C17—H17C | 89.7 | C17—N6—H6' | 116 (7) |
C18—C17—H17C | 109.3 | C25—N6—H6' | 117 (7) |
H17B—C17—H17C | 125.7 | H6A—N6—H6' | 96 (8) |
N6'—C17—H17D | 103.2 | N1'—C9'—C10 | 116.4 (9) |
N6—C17—H17D | 125.6 | N1'—C9'—H1 | 70.6 (11) |
C18—C17—H17D | 109.2 | C10—C9'—H1 | 113.0 (15) |
H17A—C17—H17D | 88.0 | N1'—C9'—H9C | 108.2 |
H17C—C17—H17D | 108.0 | C10—C9'—H9C | 108.2 |
N7—C18—N8 | 113.15 (18) | H1—C9'—H9C | 134.0 |
N7—C18—C17 | 124.43 (19) | N1'—C9'—H9D | 108.2 |
N8—C18—C17 | 122.4 (2) | C10—C9'—H9D | 108.2 |
C20—C19—N7 | 130.38 (19) | H9C—C9'—H9D | 107.3 |
C20—C19—C24 | 119.82 (19) | C17—N6'—C25 | 113.2 (12) |
N7—C19—C24 | 109.80 (17) | C17—N6'—H6' | 108 (6) |
C21—C20—C19 | 118.2 (2) | C25—N6'—H6' | 108 (6) |
C21—C20—H20 | 120.9 | C18—N7—C19 | 104.81 (17) |
C19—C20—H20 | 120.9 | C18—N8—C24 | 106.94 (17) |
C20—C21—C22 | 121.0 (2) | C18—N8—H8 | 125.5 (15) |
C20—C21—H21 | 119.5 | C24—N8—H8 | 127.5 (15) |
C22—C21—H21 | 119.5 | C26—N9—C27 | 104.75 (18) |
C23—C22—C21 | 121.9 (2) | C26—N10—C32 | 107.28 (17) |
C23—C22—H22 | 119.1 | C26—N10—H10 | 123.1 (15) |
C21—C22—H22 | 119.1 | C32—N10—H10 | 129.6 (15) |
C22—C23—C24 | 117.2 (2) | H1E—O1—H1F | 112.2 (16) |
C22—C23—H23 | 121.4 | H2A—O2—H2B | 112.5 (18) |
C24—C23—H23 | 121.4 | H2A—O2—H2C | 110 (10) |
N8—C24—C23 | 132.9 (2) | H2B—O2—H2C | 113 (10) |
N8—C24—C19 | 105.29 (17) | H2B—O2—H2D | 95 (6) |
C23—C24—C19 | 121.81 (19) | H2C—O2—H2D | 92 (10) |
N6'—C25—C26 | 100.5 (6) | H2A—O2'—H2B | 81 (2) |
N6—C25—C26 | 114.6 (3) | H2A—O2'—H2C | 79 (9) |
N6'—C25—H25A | 93.8 | H2B—O2'—H2C | 79 (10) |
N6—C25—H25A | 108.6 | H2B—O2'—H2D | 105 (10) |
C26—C25—H25A | 108.6 | H2C—O2'—H2D | 115 (2) |
N6'—C25—H25B | 135.2 | | |
| | | |
N1'—C1—C2—N3 | −11.9 (6) | C10—C9—N1—C1 | 179.2 (3) |
N1—C1—C2—N3 | 13.8 (3) | N1'—C1—N1—C9 | −54.9 (9) |
N1'—C1—C2—N2 | 172.3 (5) | C2—C1—N1—C9 | 166.1 (3) |
N1—C1—C2—N2 | −162.1 (3) | C2—C1—N1'—C9' | 98.4 (9) |
N2—C3—C4—C5 | 178.2 (2) | N1—C1—N1'—C9' | 45.6 (8) |
C8—C3—C4—C5 | −0.6 (3) | N3—C2—N2—C3 | −0.3 (2) |
C3—C4—C5—C6 | −0.7 (4) | C1—C2—N2—C3 | 176.0 (2) |
C4—C5—C6—C7 | 1.2 (4) | C4—C3—N2—C2 | −179.3 (2) |
C5—C6—C7—C8 | −0.3 (4) | C8—C3—N2—C2 | −0.4 (2) |
C6—C7—C8—N3 | −179.2 (2) | N2—C2—N3—C8 | 0.9 (2) |
C6—C7—C8—C3 | −1.0 (3) | C1—C2—N3—C8 | −175.3 (2) |
N2—C3—C8—C7 | −177.62 (19) | C7—C8—N3—C2 | 177.2 (2) |
C4—C3—C8—C7 | 1.5 (3) | C3—C8—N3—C2 | −1.1 (2) |
N2—C3—C8—N3 | 0.9 (2) | N5—C10—N4—C11 | −0.2 (2) |
C4—C3—C8—N3 | −179.98 (19) | C9—C10—N4—C11 | 176.0 (3) |
C16—C11—C12—C13 | 0.2 (3) | C9'—C10—N4—C11 | −159.3 (6) |
N4—C11—C12—C13 | 179.7 (2) | C16—C11—N4—C10 | 0.1 (2) |
C11—C12—C13—C14 | −0.4 (3) | C12—C11—N4—C10 | −179.4 (2) |
C12—C13—C14—C15 | 0.3 (4) | N4—C10—N5—C16 | 0.2 (3) |
C13—C14—C15—C16 | 0.1 (4) | C9—C10—N5—C16 | −175.8 (3) |
C14—C15—C16—N5 | −179.5 (2) | C9'—C10—N5—C16 | 164.3 (5) |
C14—C15—C16—C11 | −0.3 (3) | C15—C16—N5—C10 | 179.2 (2) |
N4—C11—C16—C15 | −179.42 (19) | C11—C16—N5—C10 | −0.1 (2) |
C12—C11—C16—C15 | 0.2 (3) | N6'—C17—N6—C25 | −68.5 (17) |
N4—C11—C16—N5 | 0.0 (2) | C18—C17—N6—C25 | −166.3 (3) |
C12—C11—C16—N5 | 179.57 (19) | N6'—C25—N6—C17 | 68.4 (17) |
N6'—C17—C18—N7 | 172.2 (6) | C26—C25—N6—C17 | 130.9 (3) |
N6—C17—C18—N7 | −158.1 (3) | C2—C1—N1—C9 | 166.1 (7) |
N6'—C17—C18—N8 | −7.8 (7) | C10—C9—N1—C1 | 179.2 (7) |
N6—C17—C18—N8 | 22.0 (3) | C2—C1—N1'—C9' | 98.3 (7) |
N7—C19—C20—C21 | 179.5 (2) | C10—C9'—N1'—C1 | −169.3 (7) |
C24—C19—C20—C21 | 0.1 (3) | C18—C17—N6—C25 | −166.3 (7) |
C19—C20—C21—C22 | −0.4 (3) | C26—C25—N6—C17 | 130.9 (7) |
C20—C21—C22—C23 | 0.1 (4) | C18—C17—N6'—C25 | 162.9 (7) |
C21—C22—C23—C24 | 0.3 (4) | C26—C25—N6'—C17 | 166.4 (7) |
C22—C23—C24—N8 | −179.7 (2) | N4—C10—C9'—N1' | −128.8 (9) |
C22—C23—C24—C19 | −0.6 (3) | N5—C10—C9'—N1' | 71.7 (11) |
C20—C19—C24—N8 | 179.74 (18) | C9—C10—C9'—N1' | −63.3 (14) |
N7—C19—C24—N8 | 0.3 (2) | N6—C17—N6'—C25 | 69.0 (13) |
C20—C19—C24—C23 | 0.4 (3) | C18—C17—N6'—C25 | 163.0 (7) |
N7—C19—C24—C23 | −179.11 (19) | N6—C25—N6'—C17 | −68.7 (13) |
N6'—C25—C26—N9 | −159.6 (7) | C26—C25—N6'—C17 | 166.4 (8) |
N6—C25—C26—N9 | 176.5 (3) | N8—C18—N7—C19 | 0.6 (2) |
N6'—C25—C26—N10 | 19.3 (7) | C17—C18—N7—C19 | −179.37 (19) |
N6—C25—C26—N10 | −4.6 (4) | C20—C19—N7—C18 | −179.9 (2) |
C32—C27—C28—C29 | −1.3 (4) | C24—C19—N7—C18 | −0.5 (2) |
N9—C27—C28—C29 | 179.9 (2) | N7—C18—N8—C24 | −0.4 (2) |
C27—C28—C29—C30 | 0.0 (4) | C17—C18—N8—C24 | 179.52 (19) |
C28—C29—C30—C31 | 0.8 (4) | C23—C24—N8—C18 | 179.3 (2) |
C29—C30—C31—C32 | −0.3 (4) | C19—C24—N8—C18 | 0.1 (2) |
C30—C31—C32—N10 | 179.3 (2) | N10—C26—N9—C27 | −0.8 (3) |
C30—C31—C32—C27 | −1.1 (3) | C25—C26—N9—C27 | 178.2 (2) |
N9—C27—C32—N10 | 0.7 (2) | C32—C27—N9—C26 | 0.1 (2) |
C28—C27—C32—N10 | −178.4 (2) | C28—C27—N9—C26 | 179.0 (2) |
N9—C27—C32—C31 | −179.0 (2) | N9—C26—N10—C32 | 1.3 (3) |
C28—C27—C32—C31 | 1.9 (3) | C25—C26—N10—C32 | −177.8 (2) |
N4—C10—C9—N1 | 172.8 (3) | C31—C32—N10—C26 | 178.5 (2) |
N5—C10—C9—N1 | −11.5 (5) | C27—C32—N10—C26 | −1.2 (2) |
C9'—C10—C9—N1 | 42.9 (16) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1′—H1′···N3 | 0.86 (1) | 2.44 (4) | 3.097 (10) | 134 (4) |
N2—H2···O3 | 0.86 (1) | 1.91 (1) | 2.756 (2) | 168 (2) |
N6′—H6′···O1 | 0.99 (8) | 2.60 (2) | 3.352 (19) | 133 (8) |
N8—H8···O1 | 0.87 (1) | 2.04 (1) | 2.902 (2) | 169 (2) |
N10—H10···O1 | 0.86 (1) | 2.16 (1) | 2.984 (2) | 159 (2) |
O2—H2A···N7 | 0.83 (1) | 2.04 (1) | 2.862 (3) | 170 (3) |
O2′—H2D···N7 | 0.82 (1) | 1.88 (2) | 2.704 (11) | 178 (16) |
O3—H3···N9i | 0.83 (1) | 1.91 (1) | 2.732 (2) | 169 (4) |
N1′—H1′···O2′ii | 0.86 (1) | 2.35 (10) | 3.045 (15) | 138 (12) |
N5—H5A···O2′ii | 0.85 (1) | 1.96 (2) | 2.758 (12) | 157 (2) |
N5—H5A···O2ii | 0.85 (1) | 2.06 (1) | 2.907 (3) | 178 (2) |
O1—H1E···N4iii | 0.83 (1) | 2.01 (1) | 2.836 (3) | 173 (3) |
O1—H1F···N1′iv | 0.83 (1) | 2.22 (2) | 2.835 (10) | 131 (2) |
O1—H1F···O2′v | 0.83 (1) | 2.23 (2) | 2.941 (11) | 143 (2) |
O1—H1F···N1iv | 0.83 (1) | 2.62 (2) | 3.347 (5) | 147 (2) |
O2—H2B···N3ii | 0.84 (1) | 2.05 (1) | 2.881 (3) | 176 (4) |
O2′—H2C···N5ii | 0.82 (1) | 2.31 (13) | 2.758 (12) | 115 (12) |
N1—H1···Cg1vi | 0.86 (1) | 2.91 (2) | 3.632 (5) | 143 (3) |
C9′—H9D···Cg1vi | 0.97 | 2.56 | 3.485 (11) | 159 |
C30—H30···Cg1iv | 0.93 | 2.91 | 3.661 (3) | 138 |
C6—H6···Cg2vii | 0.93 | 2.91 | 3.661 (3) | 139 |
C7—H7···Cg3vii | 0.93 | 2.93 | 3.758 (3) | 149 |
C15—H15···Cg4vii | 0.93 | 3.00 | 3.713 (3) | 135 |
C23—H23···Cg5iv | 0.93 | 2.88 | 3.600 (3) | 136 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z+1; (iv) x, y, z+1; (v) −x+1, −y+1, −z+2; (vi) −x+2, −y, −z; (vii) x+1, y, z−1. |