Bis(benzimidazol-2-ylmeth­yl)amine–ethanol–water (2/1/2)

In the asymmetric unit of the structure of the solvate of bis­(benzimidazol-2-yl-meth­yl)amine (IDB), 2C₁₆H₁₅N₅·C₂H₆O·2H₂O, 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.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](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

---

Computing details

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)

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.167	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0783P)^2] where P = (Fo^2 + 2Fc^2)/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

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

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

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

	x	y	z	Uiso*/Ueq	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···N9^i	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···O2^ii	0.85 (1)	2.06 (1)	2.907 (3)	178 (2)
O1—H1E···N4^iii	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···N1^iv	0.83 (1)	2.62 (2)	3.347 (5)	147 (2)
O2—H2B···N3^ii	0.84 (1)	2.05 (1)	2.881 (3)	176 (4)
O2′—H2C···N5^ii	0.82 (1)	2.31 (13)	2.758 (12)	115 (12)
N1—H1···Cg1^vi	0.86 (1)	2.91 (2)	3.632 (5)	143 (3)
C9′—H9D···Cg1^vi	0.97	2.56	3.485 (11)	159
C30—H30···Cg1^iv	0.93	2.91	3.661 (3)	138
C6—H6···Cg2^vii	0.93	2.91	3.661 (3)	139
C7—H7···Cg3^vii	0.93	2.93	3.758 (3)	149
C15—H15···Cg4^vii	0.93	3.00	3.713 (3)	135
C23—H23···Cg5^iv	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.