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The title compound, C22H27N7·4.5H2O, crystallizes with two mol­ecules of 1,4-bis­(benzimidazol-2-ylmeth­yl)-1,4,7-triaza­cyclo­nonane and nine disordered water mol­ecules in the asymmetric unit. Each triazacyclononane group exhibits an intra­molecular N—H...N hydrogen bond. The crystal packing is dominated by N—H...O and O—H...N hydrogen bonds between organic mol­ecules and water mol­ecules, and also between water mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806011305/kp2007sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806011305/kp2007Isup2.hkl
Contains datablock I

CCDC reference: 608433

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in solvent or counterion
  • R factor = 0.066
  • wR factor = 0.142
  • Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



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 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 27.00 Perc. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 17 H2 O
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1,4-Bis(1H-benzimidazol-2-ylmethyl)-1,4,7-triazacyclonone 4.5-hydrate top
Crystal data top
C22H27N7·4.5H2OF(000) = 2024
Mr = 470.58Dx = 1.022 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6376 reflections
a = 7.4815 (5) Åθ = 2.2–25.2°
b = 21.5452 (14) ŵ = 0.07 mm1
c = 37.968 (3) ÅT = 294 K
β = 91.261 (1)°Block, yellow
V = 6118.5 (7) Å30.30 × 0.26 × 0.24 mm
Z = 8
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
12024 independent reflections
Radiation source: sealed tube7076 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
φ annd ω scansθmax = 26.0°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 99
Tmin = 0.97, Tmax = 0.98k = 2626
63905 measured reflectionsl = 4646
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.05P)2 + 1.22P]
where P = (Fo2 + 2Fc2)/3
12024 reflections(Δ/σ)max < 0.001
658 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.28 e Å3
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
xyzUiso*/UeqOcc. (<1)
C10.1859 (3)0.33911 (11)0.65638 (6)0.0523 (6)
H1A0.15720.38240.66060.063*
H1B0.07690.31510.65840.063*
C20.2568 (3)0.33196 (10)0.61995 (6)0.0487 (5)
H2A0.34900.36270.61590.058*
H2B0.16130.33820.60260.058*
C30.1928 (3)0.21736 (10)0.61558 (6)0.0520 (6)
H3A0.17240.20300.59160.062*
H3B0.08100.23310.62440.062*
C40.2606 (3)0.16459 (11)0.63855 (6)0.0550 (6)
H4A0.16450.13510.64190.066*
H4B0.35620.14330.62660.066*
C50.1938 (3)0.21461 (10)0.69520 (6)0.0504 (5)
H5A0.17020.18710.71480.060*
H5B0.08280.22010.68190.060*
C60.2559 (3)0.27699 (10)0.70935 (6)0.0495 (5)
H6A0.15800.29650.72150.059*
H6B0.35230.27030.72640.059*
C70.4474 (3)0.36577 (11)0.69455 (6)0.0569 (6)
H7A0.50610.38230.67410.068*
H7B0.53810.34590.70930.068*
C80.3685 (3)0.41820 (10)0.71449 (6)0.0515 (5)
C90.2640 (3)0.51055 (10)0.72740 (6)0.0466 (5)
C100.1989 (3)0.57269 (12)0.72770 (7)0.0630 (6)
H100.18910.59630.70720.076*
C110.1520 (3)0.59554 (11)0.75964 (6)0.0577 (6)
H110.11620.63680.76100.069*
C120.1551 (3)0.56078 (11)0.78961 (7)0.0581 (6)
H120.11470.57840.81030.070*
C130.2163 (3)0.50021 (11)0.79030 (6)0.0556 (6)
H130.21950.47720.81100.067*
C140.2723 (3)0.47548 (10)0.75896 (6)0.0472 (5)
C150.4561 (3)0.14630 (10)0.69067 (6)0.0480 (5)
H15A0.50910.16920.71030.058*
H15B0.55070.13620.67460.058*
C160.3782 (3)0.08796 (10)0.70411 (6)0.0480 (5)
C170.2759 (3)0.00859 (11)0.70774 (6)0.0531 (6)
C180.2172 (3)0.06970 (10)0.70183 (6)0.0510 (5)
H180.21590.08730.67950.061*
C190.1633 (3)0.10144 (11)0.72998 (6)0.0503 (5)
H190.12530.14230.72730.060*
C200.1631 (3)0.07392 (11)0.76367 (6)0.0532 (6)
H200.12510.09820.78230.064*
C210.2130 (3)0.01611 (12)0.77083 (6)0.0580 (6)
H210.21010.00090.79330.070*
C220.2716 (3)0.01772 (11)0.74090 (6)0.0513 (5)
C230.6629 (3)0.33514 (10)0.40561 (5)0.0486 (5)
H23A0.63290.37860.40850.058*
H23B0.55560.31080.40910.058*
C240.7323 (3)0.32400 (11)0.36815 (6)0.0580 (6)
H24A0.63390.32670.35120.070*
H24B0.81930.35560.36250.070*
C250.6911 (3)0.21078 (11)0.36742 (6)0.0560 (6)
H25A0.67200.19480.34380.067*
H25B0.57690.22520.37580.067*
C260.7600 (3)0.15799 (11)0.39145 (6)0.0521 (6)
H26A0.66510.12810.39500.063*
H26B0.85810.13680.38030.063*
C270.6860 (3)0.21283 (10)0.44638 (6)0.0511 (5)
H27A0.65880.18640.46620.061*
H27B0.57750.21760.43220.061*
C280.7457 (3)0.27650 (10)0.46004 (5)0.0465 (5)
H28A0.64810.29570.47240.056*
H28B0.84480.27120.47670.056*
C290.9279 (3)0.36555 (11)0.44192 (6)0.0562 (6)
H29A0.97380.38430.42070.067*
H29B1.02790.34610.45430.067*
C300.8569 (3)0.41579 (10)0.46459 (6)0.0487 (5)
C310.7454 (3)0.50426 (11)0.48498 (6)0.0527 (6)
C320.6766 (3)0.56253 (11)0.48858 (6)0.0558 (6)
H320.65180.58750.46910.067*
C330.6457 (3)0.58242 (12)0.52186 (6)0.0545 (6)
H330.59520.62130.52530.065*
C340.6869 (3)0.54686 (11)0.54981 (6)0.0527 (6)
H340.67050.56290.57230.063*
C350.7528 (3)0.48724 (11)0.54654 (7)0.0563 (6)
H350.77310.46240.56630.068*
C360.7866 (3)0.46624 (11)0.51415 (6)0.0555 (6)
C370.9505 (3)0.14493 (10)0.44515 (6)0.0500 (5)
H37A1.00060.16920.46450.060*
H37B1.04740.13430.42970.060*
C380.8759 (3)0.08725 (10)0.45949 (6)0.0471 (5)
C390.7794 (3)0.00917 (10)0.46648 (6)0.0496 (5)
C400.7258 (3)0.06996 (11)0.46196 (7)0.0583 (6)
H400.72900.08980.44020.070*
C410.6677 (3)0.09922 (11)0.49167 (7)0.0582 (6)
H410.63120.14040.48970.070*
C420.6599 (3)0.07084 (12)0.52472 (7)0.0613 (7)
H420.62200.09330.54410.074*
C430.7076 (3)0.01069 (11)0.52834 (6)0.0546 (6)
H430.69890.00960.54990.066*
C440.7710 (3)0.02040 (11)0.49839 (6)0.0503 (5)
N10.3164 (2)0.31819 (8)0.68274 (5)0.0514 (5)
N20.3328 (3)0.26782 (8)0.61641 (5)0.0524 (5)
H2C0.40880.26080.63470.063*
N30.3259 (2)0.18573 (8)0.67257 (5)0.0484 (4)
N40.3261 (2)0.47259 (8)0.70186 (5)0.0492 (4)
H40.33620.48310.68010.059*
N50.3365 (2)0.41830 (8)0.74922 (5)0.0479 (4)
N60.3445 (2)0.03607 (9)0.68581 (5)0.0512 (5)
N70.3354 (3)0.07741 (9)0.73753 (5)0.0553 (5)
H70.34600.10390.75440.066*
N80.8005 (2)0.31734 (8)0.43163 (5)0.0480 (4)
N90.8145 (2)0.26305 (8)0.36621 (5)0.0491 (5)
H9A0.89430.25930.38420.059*
N100.8209 (2)0.18328 (8)0.42554 (4)0.0428 (4)
N110.7912 (2)0.46896 (9)0.45497 (5)0.0506 (5)
H11A0.77730.48110.43350.061*
N120.8542 (3)0.41055 (9)0.50063 (5)0.0600 (5)
N130.8444 (2)0.03517 (8)0.44374 (5)0.0481 (4)
H13A0.86180.02880.42170.058*
N140.8266 (2)0.08042 (8)0.49383 (4)0.0429 (4)
O10.2163 (4)0.61291 (15)0.88526 (8)0.0386 (8)0.40
H1D0.32120.61710.89400.046*0.40
H1E0.18610.64600.87450.046*0.40
O20.4792 (5)0.72461 (16)0.45344 (9)0.0464 (9)0.40
H2E0.49840.75250.43820.056*0.40
H2F0.49390.68900.44430.056*0.40
O30.7144 (5)0.49975 (17)0.37789 (10)0.0562 (10)0.40
H3D0.60220.50280.37440.067*0.40
H3E0.76410.53400.37280.067*0.40
O40.7684 (5)0.24306 (14)0.23019 (9)0.0408 (8)0.40
H4E0.79680.22770.21050.049*0.40
H4F0.65710.25090.23000.049*0.40
O50.8409 (5)0.47745 (16)0.64193 (9)0.0482 (9)0.40
H5E0.88850.44170.64050.058*0.40
H5F0.74480.47830.62960.058*0.40
O60.8329 (2)0.17663 (7)0.54300 (4)0.0540 (4)
H6C0.89850.14490.54000.065*
H6E0.76400.17020.56010.065*
O70.7212 (5)0.34956 (17)0.61338 (10)0.0518 (9)0.40
H7F0.74070.31810.60050.062*0.40
H7C0.77980.34600.63270.062*0.40
O80.3772 (4)0.18115 (15)0.79300 (9)0.0440 (8)0.40
H8D0.41380.19880.77450.053*0.40
H8C0.45840.15720.80120.053*0.40
O90.47605 (19)0.01240 (7)0.61949 (4)0.0495 (4)
H9F0.46400.03130.63900.059*
H9E0.58450.01450.61340.059*
O100.2051 (5)0.14010 (17)0.86493 (10)0.0526 (10)0.40
H10B0.15560.11030.87560.063*0.40
H10D0.22840.12920.84400.063*0.40
O110.3473 (2)0.33101 (7)0.80130 (4)0.0558 (4)
H11B0.33970.36250.81470.067*
H11D0.27370.33480.78410.067*
O120.9835 (4)0.00977 (16)0.37816 (9)0.0446 (8)0.40
H12A0.94160.02680.37620.053*0.40
H12B0.94030.03240.36170.053*0.40
O130.28393 (19)0.11084 (6)0.37363 (4)0.0459 (4)
H13B0.38350.09670.38130.055*
H13C0.19980.08750.38040.055*
O141.2258 (5)0.24921 (17)0.40344 (9)0.0489 (9)0.40
H14A1.18190.28640.41170.059*0.40
H14B1.17710.23960.38780.059*0.40
O150.9775 (2)0.30901 (7)0.54434 (4)0.0585 (4)
H15E0.94640.27130.54170.070*
H15C0.95240.32920.52570.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0568 (14)0.0444 (12)0.0551 (14)0.0047 (10)0.0095 (11)0.0065 (10)
C20.0519 (13)0.0511 (13)0.0427 (12)0.0008 (10)0.0057 (10)0.0005 (10)
C30.0574 (14)0.0453 (13)0.0528 (13)0.0014 (10)0.0113 (11)0.0119 (10)
C40.0529 (14)0.0527 (14)0.0585 (15)0.0007 (11)0.0186 (11)0.0124 (11)
C50.0531 (13)0.0409 (12)0.0575 (14)0.0018 (10)0.0081 (10)0.0058 (10)
C60.0573 (13)0.0401 (12)0.0510 (13)0.0008 (10)0.0007 (10)0.0007 (10)
C70.0672 (15)0.0509 (14)0.0526 (14)0.0005 (12)0.0002 (12)0.0009 (11)
C80.0640 (15)0.0391 (12)0.0514 (13)0.0046 (10)0.0012 (11)0.0059 (10)
C90.0516 (13)0.0447 (12)0.0434 (12)0.0060 (10)0.0025 (10)0.0051 (10)
C100.0630 (16)0.0567 (15)0.0690 (17)0.0012 (12)0.0068 (12)0.0004 (13)
C110.0616 (15)0.0521 (14)0.0598 (15)0.0025 (11)0.0146 (12)0.0145 (12)
C120.0558 (14)0.0592 (15)0.0596 (15)0.0049 (11)0.0090 (11)0.0283 (12)
C130.0572 (14)0.0586 (15)0.0510 (14)0.0128 (11)0.0015 (11)0.0067 (11)
C140.0457 (12)0.0440 (12)0.0517 (13)0.0100 (9)0.0043 (10)0.0033 (10)
C150.0470 (12)0.0470 (13)0.0504 (13)0.0118 (10)0.0087 (10)0.0018 (10)
C160.0477 (12)0.0482 (13)0.0479 (13)0.0131 (10)0.0034 (10)0.0003 (10)
C170.0549 (13)0.0482 (13)0.0559 (14)0.0132 (11)0.0065 (11)0.0006 (11)
C180.0508 (13)0.0438 (12)0.0579 (14)0.0049 (10)0.0083 (10)0.0111 (10)
C190.0514 (13)0.0474 (13)0.0516 (13)0.0026 (10)0.0112 (10)0.0139 (11)
C200.0573 (14)0.0515 (14)0.0509 (14)0.0093 (11)0.0061 (11)0.0139 (11)
C210.0601 (14)0.0646 (16)0.0501 (14)0.0113 (12)0.0172 (11)0.0158 (12)
C220.0460 (12)0.0515 (13)0.0562 (14)0.0090 (10)0.0021 (10)0.0044 (11)
C230.0582 (14)0.0438 (12)0.0435 (12)0.0056 (10)0.0022 (10)0.0084 (9)
C240.0563 (14)0.0600 (15)0.0576 (15)0.0042 (12)0.0001 (11)0.0138 (12)
C250.0686 (15)0.0499 (13)0.0489 (13)0.0028 (11)0.0133 (11)0.0064 (11)
C260.0521 (13)0.0538 (13)0.0498 (13)0.0014 (11)0.0137 (10)0.0050 (10)
C270.0554 (13)0.0388 (12)0.0599 (14)0.0080 (10)0.0179 (11)0.0053 (10)
C280.0563 (13)0.0442 (12)0.0393 (11)0.0038 (10)0.0069 (10)0.0003 (9)
C290.0564 (14)0.0560 (14)0.0567 (14)0.0048 (11)0.0119 (11)0.0069 (11)
C300.0507 (13)0.0425 (13)0.0527 (13)0.0131 (10)0.0003 (10)0.0072 (10)
C310.0489 (13)0.0498 (14)0.0590 (14)0.0023 (10)0.0040 (10)0.0133 (11)
C320.0616 (14)0.0551 (14)0.0508 (14)0.0013 (11)0.0020 (11)0.0270 (11)
C330.0510 (13)0.0610 (15)0.0520 (13)0.0115 (11)0.0071 (11)0.0156 (12)
C340.0550 (13)0.0539 (14)0.0491 (14)0.0010 (11)0.0009 (11)0.0159 (11)
C350.0521 (13)0.0521 (13)0.0642 (15)0.0137 (11)0.0057 (11)0.0303 (12)
C360.0566 (14)0.0496 (14)0.0602 (15)0.0095 (11)0.0002 (11)0.0218 (12)
C370.0469 (12)0.0521 (13)0.0508 (13)0.0006 (10)0.0015 (10)0.0028 (10)
C380.0533 (13)0.0449 (13)0.0430 (12)0.0035 (10)0.0022 (10)0.0040 (10)
C390.0415 (12)0.0490 (13)0.0582 (14)0.0026 (10)0.0024 (10)0.0020 (11)
C400.0569 (14)0.0569 (15)0.0606 (15)0.0080 (11)0.0112 (11)0.0131 (12)
C410.0692 (16)0.0453 (13)0.0601 (16)0.0055 (11)0.0015 (12)0.0160 (12)
C420.0530 (14)0.0606 (16)0.0701 (17)0.0119 (12)0.0035 (12)0.0441 (13)
C430.0561 (14)0.0576 (15)0.0503 (13)0.0106 (11)0.0073 (11)0.0165 (11)
C440.0461 (12)0.0536 (13)0.0509 (13)0.0026 (10)0.0052 (10)0.0084 (11)
N10.0524 (11)0.0476 (11)0.0540 (12)0.0004 (9)0.0054 (9)0.0032 (9)
N20.0642 (12)0.0514 (11)0.0415 (10)0.0086 (9)0.0010 (9)0.0068 (8)
N30.0516 (10)0.0402 (10)0.0531 (11)0.0039 (8)0.0020 (8)0.0028 (8)
N40.0505 (10)0.0452 (11)0.0516 (11)0.0013 (8)0.0046 (8)0.0011 (9)
N50.0562 (11)0.0428 (10)0.0445 (10)0.0067 (8)0.0063 (8)0.0010 (8)
N60.0567 (12)0.0458 (11)0.0508 (11)0.0052 (9)0.0028 (9)0.0056 (9)
N70.0664 (13)0.0448 (11)0.0543 (12)0.0185 (9)0.0071 (9)0.0052 (9)
N80.0503 (10)0.0405 (10)0.0530 (11)0.0019 (8)0.0021 (8)0.0052 (8)
N90.0561 (11)0.0515 (11)0.0396 (10)0.0050 (9)0.0005 (8)0.0108 (8)
N100.0458 (10)0.0404 (9)0.0419 (10)0.0011 (8)0.0049 (8)0.0041 (7)
N110.0499 (11)0.0509 (11)0.0512 (11)0.0020 (9)0.0059 (9)0.0031 (9)
N120.0667 (13)0.0566 (12)0.0566 (12)0.0039 (10)0.0014 (10)0.0115 (10)
N130.0651 (12)0.0396 (10)0.0396 (10)0.0050 (8)0.0035 (8)0.0012 (8)
N140.0481 (10)0.0417 (10)0.0387 (9)0.0025 (8)0.0013 (7)0.0104 (7)
O10.0402 (18)0.0410 (19)0.0350 (18)0.0122 (14)0.0096 (14)0.0107 (14)
O20.054 (2)0.047 (2)0.0386 (19)0.0318 (17)0.0131 (16)0.0083 (16)
O30.053 (2)0.060 (3)0.055 (2)0.0087 (19)0.0143 (18)0.0213 (19)
O40.0465 (19)0.0344 (18)0.0420 (19)0.0018 (15)0.0077 (15)0.0123 (15)
O50.055 (2)0.043 (2)0.047 (2)0.0108 (17)0.0131 (17)0.0051 (16)
O60.0515 (9)0.0530 (9)0.0583 (10)0.0001 (7)0.0205 (7)0.0068 (7)
O70.050 (2)0.050 (2)0.054 (2)0.0141 (18)0.0149 (17)0.0100 (18)
O80.050 (2)0.0407 (19)0.0407 (19)0.0180 (16)0.0131 (16)0.0071 (15)
O90.0497 (8)0.0495 (8)0.0498 (9)0.0043 (7)0.0140 (7)0.0202 (7)
O100.051 (2)0.056 (2)0.050 (2)0.0155 (18)0.0102 (17)0.0134 (18)
O110.0553 (9)0.0578 (10)0.0549 (9)0.0011 (7)0.0192 (8)0.0029 (7)
O120.044 (2)0.0422 (19)0.048 (2)0.0029 (15)0.0080 (16)0.0020 (16)
O130.0468 (8)0.0456 (8)0.0460 (8)0.0044 (6)0.0141 (6)0.0014 (6)
O140.047 (2)0.053 (2)0.046 (2)0.0121 (17)0.0068 (16)0.0098 (17)
O150.0539 (9)0.0600 (10)0.0609 (10)0.0109 (8)0.0163 (8)0.0100 (8)
Geometric parameters (Å, º) top
C1—N11.454 (3)C28—N81.458 (3)
C1—C21.500 (3)C28—H28A0.9700
C1—H1A0.9700C28—H28B0.9700
C1—H1B0.9700C29—N81.458 (3)
C2—N21.502 (3)C29—C301.488 (3)
C2—H2A0.9700C29—H29A0.9700
C2—H2B0.9700C29—H29B0.9700
C3—N21.509 (3)C30—N111.296 (3)
C3—C41.514 (3)C30—N121.373 (3)
C3—H3A0.9700C31—C321.365 (3)
C3—H3B0.9700C31—C361.406 (3)
C4—N31.445 (3)C31—N111.418 (3)
C4—H4A0.9700C32—C331.359 (3)
C4—H4B0.9700C32—H320.9300
C5—N31.463 (3)C33—C341.339 (3)
C5—C61.517 (3)C33—H330.9300
C5—H5A0.9700C34—C351.382 (3)
C5—H5B0.9700C34—H340.9300
C6—N11.426 (3)C35—C361.340 (3)
C6—H6A0.9700C35—H350.9300
C6—H6B0.9700C36—N121.404 (3)
C7—N11.481 (3)C37—N101.464 (3)
C7—C81.489 (3)C37—C381.472 (3)
C7—H7A0.9700C37—H37A0.9700
C7—H7B0.9700C37—H37B0.9700
C8—N41.303 (3)C38—N131.290 (3)
C8—N51.345 (3)C38—N141.371 (3)
C9—N41.358 (3)C39—C441.372 (3)
C9—C141.417 (3)C39—C401.379 (3)
C9—C101.425 (3)C39—N131.383 (3)
C10—C111.362 (3)C40—C411.371 (3)
C10—H100.9300C40—H400.9300
C11—C121.362 (3)C41—C421.398 (4)
C11—H110.9300C41—H410.9300
C12—C131.383 (3)C42—C431.351 (3)
C12—H120.9300C42—H420.9300
C13—C141.377 (3)C43—C441.411 (3)
C13—H130.9300C43—H430.9300
C14—N51.376 (3)C44—N141.371 (3)
C15—N31.454 (3)N2—H2C0.8999
C15—C161.481 (3)N4—H40.8600
C15—H15A0.9700N7—H70.8600
C15—H15B0.9700N9—H9A0.9000
C16—N71.335 (3)N11—H11A0.8600
C16—N61.337 (3)N13—H13A0.8600
C17—N61.379 (3)O1—H1D0.8499
C17—C221.382 (3)O1—H1E0.8499
C17—C181.404 (3)O2—H2E0.8501
C18—C191.338 (3)O2—H2F0.8500
C18—H180.9300O3—H3D0.8500
C19—C201.410 (3)O3—H3E0.8499
C19—H190.9300O4—H4E0.8499
C20—C211.327 (3)O4—H4F0.8500
C20—H200.9300O5—H5E0.8501
C21—C221.427 (3)O5—H5F0.8500
C21—H210.9300O6—H6C0.8500
C22—N71.379 (3)O6—H6E0.8502
C23—N81.462 (3)O7—H7F0.8499
C23—C241.544 (3)O7—H7C0.8501
C23—H23A0.9700O8—H8D0.8500
C23—H23B0.9700O8—H8C0.8500
C24—N91.453 (3)O9—H9F0.8501
C24—H24A0.9700O9—H9E0.8500
C24—H24B0.9700O10—H10B0.8501
C25—N91.457 (3)O10—H10D0.8499
C25—C261.540 (3)O11—H11B0.8501
C25—H25A0.9700O11—H11D0.8498
C25—H25B0.9700O12—H12A0.8500
C26—N101.468 (3)O12—H12B0.8499
C26—H26A0.9700O13—H13B0.8501
C26—H26B0.9700O13—H13C0.8500
C27—N101.444 (3)O14—H14A0.9235
C27—C281.530 (3)O14—H14B0.7205
C27—H27A0.9700O15—H15E0.8500
C27—H27B0.9700O15—H15C0.8499
N1—C1—C2110.91 (19)N10—C27—H27A109.2
N1—C1—H1A109.5C28—C27—H27A109.2
C2—C1—H1A109.5N10—C27—H27B109.2
N1—C1—H1B109.5C28—C27—H27B109.2
C2—C1—H1B109.5H27A—C27—H27B107.9
H1A—C1—H1B108.0N8—C28—C27112.04 (17)
C1—C2—N2108.62 (18)N8—C28—H28A109.2
C1—C2—H2A110.0C27—C28—H28A109.2
N2—C2—H2A110.0N8—C28—H28B109.2
C1—C2—H2B110.0C27—C28—H28B109.2
N2—C2—H2B110.0H28A—C28—H28B107.9
H2A—C2—H2B108.3N8—C29—C30115.68 (19)
N2—C3—C4107.80 (18)N8—C29—H29A108.4
N2—C3—H3A110.1C30—C29—H29A108.4
C4—C3—H3A110.1N8—C29—H29B108.4
N2—C3—H3B110.1C30—C29—H29B108.4
C4—C3—H3B110.1H29A—C29—H29B107.4
H3A—C3—H3B108.5N11—C30—N12109.9 (2)
N3—C4—C3112.38 (18)N11—C30—C29128.2 (2)
N3—C4—H4A109.1N12—C30—C29122.0 (2)
C3—C4—H4A109.1C32—C31—C36122.2 (2)
N3—C4—H4B109.1C32—C31—N11132.2 (2)
C3—C4—H4B109.1C36—C31—N11105.54 (19)
H4A—C4—H4B107.9C33—C32—C31117.1 (3)
N3—C5—C6112.28 (19)C33—C32—H32121.5
N3—C5—H5A109.1C31—C32—H32121.5
C6—C5—H5A109.1C34—C33—C32121.0 (2)
N3—C5—H5B109.1C34—C33—H33119.5
C6—C5—H5B109.1C32—C33—H33119.5
H5A—C5—H5B107.9C33—C34—C35122.5 (2)
N1—C6—C5113.58 (19)C33—C34—H34118.8
N1—C6—H6A108.8C35—C34—H34118.8
C5—C6—H6A108.8C36—C35—C34118.1 (3)
N1—C6—H6B108.8C36—C35—H35121.0
C5—C6—H6B108.8C34—C35—H35121.0
H6A—C6—H6B107.7C35—C36—N12134.5 (3)
N1—C7—C8114.3 (2)C35—C36—C31118.9 (2)
N1—C7—H7A108.7N12—C36—C31106.5 (2)
C8—C7—H7A108.7N10—C37—C38114.36 (18)
N1—C7—H7B108.7N10—C37—H37A108.7
C8—C7—H7B108.7C38—C37—H37A108.7
H7A—C7—H7B107.6N10—C37—H37B108.7
N4—C8—N5108.21 (19)C38—C37—H37B108.7
N4—C8—C7126.2 (2)H37A—C37—H37B107.6
N5—C8—C7125.5 (2)N13—C38—N14107.29 (19)
N4—C9—C14105.87 (19)N13—C38—C37129.0 (2)
N4—C9—C10133.9 (2)N14—C38—C37123.69 (19)
C14—C9—C10120.2 (2)C44—C39—C40122.2 (2)
C11—C10—C9116.2 (2)C44—C39—N13104.7 (2)
C11—C10—H10121.9C40—C39—N13133.1 (2)
C9—C10—H10121.9C41—C40—C39115.5 (2)
C10—C11—C12123.0 (2)C41—C40—H40122.2
C10—C11—H11118.5C39—C40—H40122.2
C12—C11—H11118.5C40—C41—C42123.9 (2)
C11—C12—C13122.3 (2)C40—C41—H41118.1
C11—C12—H12118.9C42—C41—H41118.1
C13—C12—H12118.9C43—C42—C41119.7 (2)
C14—C13—C12117.1 (2)C43—C42—H42120.2
C14—C13—H13121.4C41—C42—H42120.2
C12—C13—H13121.4C42—C43—C44117.8 (2)
N5—C14—C13133.9 (2)C42—C43—H43121.1
N5—C14—C9105.02 (19)C44—C43—H43121.1
C13—C14—C9121.1 (2)N14—C44—C39107.9 (2)
N3—C15—C16113.23 (18)N14—C44—C43131.2 (2)
N3—C15—H15A108.9C39—C44—C43120.9 (2)
C16—C15—H15A108.9C6—N1—C1117.51 (19)
N3—C15—H15B108.9C6—N1—C7115.74 (18)
C16—C15—H15B108.9C1—N1—C7115.06 (18)
H15A—C15—H15B107.7C2—N2—C3113.62 (18)
N7—C16—N6107.8 (2)C2—N2—H2C108.7
N7—C16—C15125.2 (2)C3—N2—H2C108.7
N6—C16—C15127.0 (2)C4—N3—C15116.64 (17)
N6—C17—C22106.3 (2)C4—N3—C5116.09 (18)
N6—C17—C18132.6 (2)C15—N3—C5115.17 (18)
C22—C17—C18121.1 (2)C8—N4—C9111.28 (19)
C19—C18—C17116.8 (2)C8—N4—H4124.4
C19—C18—H18121.6C9—N4—H4124.4
C17—C18—H18121.6C8—N5—C14109.61 (18)
C18—C19—C20121.0 (2)C16—N6—C17109.76 (19)
C18—C19—H19119.5C16—N7—C22109.74 (19)
C20—C19—H19119.5C16—N7—H7125.1
C21—C20—C19125.1 (2)C22—N7—H7125.1
C21—C20—H20117.5C28—N8—C29115.13 (18)
C19—C20—H20117.5C28—N8—C23116.95 (18)
C20—C21—C22114.0 (2)C29—N8—C23116.17 (18)
C20—C21—H21123.0C24—N9—C25115.33 (19)
C22—C21—H21123.0C24—N9—H9A108.4
N7—C22—C17106.4 (2)C25—N9—H9A108.5
N7—C22—C21131.5 (2)C27—N10—C37115.65 (17)
C17—C22—C21122.0 (2)C27—N10—C26116.09 (18)
N8—C23—C24109.60 (18)C37—N10—C26115.34 (17)
N8—C23—H23A109.8C30—N11—C31110.1 (2)
C24—C23—H23A109.8C30—N11—H11A124.9
N8—C23—H23B109.8C31—N11—H11A124.9
C24—C23—H23B109.8C30—N12—C36107.9 (2)
H23A—C23—H23B108.2C38—N13—C39112.00 (19)
N9—C24—C23109.80 (18)C38—N13—H13A124.0
N9—C24—H24A109.7C39—N13—H13A124.0
C23—C24—H24A109.7C44—N14—C38108.07 (18)
N9—C24—H24B109.7H1D—O1—H1E109.5
C23—C24—H24B109.7H2E—O2—H2F109.5
H24A—C24—H24B108.2H3D—O3—H3E109.5
N9—C25—C26112.68 (19)H4E—O4—H4F109.5
N9—C25—H25A109.1H5E—O5—H5F109.5
C26—C25—H25A109.1H6C—O6—H6E109.5
N9—C25—H25B109.1H7F—O7—H7C109.5
C26—C25—H25B109.1H8D—O8—H8C109.5
H25A—C25—H25B107.8H9F—O9—H9E109.5
N10—C26—C25109.97 (18)H10B—O10—H10D109.8
N10—C26—H26A109.7H11B—O11—H11D109.5
C25—C26—H26A109.7H12A—O12—H12B109.5
N10—C26—H26B109.7H13B—O13—H13C109.5
C25—C26—H26B109.7H14A—O14—H14B110.7
H26A—C26—H26B108.2H15E—O15—H15C109.6
N10—C27—C28112.25 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2C···N30.902.262.772 (3)116
N7—H7···O80.862.233.082 (4)173
N9—H9A···N100.902.342.833 (2)114
N9—H9A···O140.902.583.371 (4)147
N11—H11A···O30.862.193.043 (4)171
N13—H13A···O120.861.952.774 (4)160
O5—H5E···O70.852.553.087 (5)122
O6—H6C···N140.852.292.789 (2)118
O9—H9F···N60.852.012.771 (2)148
O10—H10D···O80.852.523.171 (5)134
O11—H11D···N50.852.292.729 (2)113
O15—H15E···O60.852.213.051 (2)169
O15—H15C···N120.852.122.885 (3)150
N4—H4···O3i0.862.263.094 (4)164
O2—H2E···N2i0.852.493.033 (4)123
O6—H6E···O1ii0.852.413.079 (3)136
O9—H9E···O1ii0.852.593.168 (3)126
O11—H11B···O13iii0.852.363.065 (2)141
O13—H13B···O9iv0.852.583.2128 (19)133
O13—H13C···O12v0.852.333.137 (4)159
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y1/2, z+3/2; (iii) x, y+1/2, z+1/2; (iv) x+1, y, z+1; (v) x1, y, z.
 

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