In the crystal of the ternary co-crystalline adduct, the components interact through two intermolecular O—H
N hydrogen bonds. The supramolecular adducts are interlinked through of halogen bonds and weak non-conventional hydrogen bonds.
Supporting information
CCDC reference: 1580038
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.008 Å
- R factor = 0.025
- wR factor = 0.065
- Data-to-parameter ratio = 15.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density. 0 Info
Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 2 Note
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large 5.13 Why ?
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 1 Report
PLAT300_ALERT_4_G Atom Site Occupancy of H1A is Constrained at 0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H1B is Constrained at 0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H3A is Constrained at 0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H3B is Constrained at 0.5 Check
PLAT431_ALERT_2_G Short Inter HL..A Contact I1 .. N2 .. 3.35 Ang.
PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 2 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 2 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities ....... Please Check
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
11 ALERT level G = General information/check it is not something unexpected
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
5 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS2016 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015).
1,3,6,8-Tetraazatricyclo[4.4.1.1
3,8]dodecane–4-iodophenol (1/2)
top
Crystal data top
C8H16N4·2C6H5IO | Dx = 1.791 Mg m−3 |
Mr = 608.25 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Fdd2 | Cell parameters from 15571 reflections |
a = 20.8869 (16) Å | θ = 3.6–25.9° |
b = 22.4197 (13) Å | µ = 2.81 mm−1 |
c = 9.6352 (6) Å | T = 173 K |
V = 4512.0 (5) Å3 | Block, yellow |
Z = 8 | 0.24 × 0.23 × 0.23 mm |
F(000) = 2368 | |
Data collection top
Stoe IPDS II two-circle diffractometer | 2079 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.029 |
ω scans | θmax = 25.5°, θmin = 3.6° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −24→25 |
Tmin = 0.548, Tmax = 1.000 | k = −26→27 |
7213 measured reflections | l = −11→11 |
2102 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.025 | w = 1/[σ2(Fo2) + (0.0495P)2 + 5.1297P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.065 | (Δ/σ)max = 0.002 |
S = 1.06 | Δρmax = 0.25 e Å−3 |
2102 reflections | Δρmin = −0.67 e Å−3 |
132 parameters | Absolute structure: Classical Flack (1983) method preferred over Parsons because s.u. lower |
2 restraints | Absolute structure parameter: −0.03 (4) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
N1 | 0.5189 (2) | 0.55327 (17) | 0.2785 (4) | 0.0293 (9) | |
N2 | 0.4501 (2) | 0.5309 (2) | 0.0695 (5) | 0.0335 (9) | |
C1 | 0.500000 | 0.500000 | 0.3551 (8) | 0.0350 (16) | |
H1A | 0.463825 | 0.511142 | 0.416230 | 0.042* | 0.5 |
H1B | 0.536176 | 0.488858 | 0.416229 | 0.042* | 0.5 |
C2 | 0.4734 (3) | 0.5730 (3) | 0.1705 (6) | 0.0413 (13) | |
H2A | 0.435585 | 0.589927 | 0.218543 | 0.050* | |
H2B | 0.493847 | 0.606119 | 0.119081 | 0.050* | |
C3 | 0.500000 | 0.500000 | −0.0073 (9) | 0.0383 (16) | |
H3A | 0.521109 | 0.529565 | −0.068331 | 0.046* | 0.5 |
H3B | 0.478891 | 0.470437 | −0.068336 | 0.046* | 0.5 |
C4 | 0.3977 (3) | 0.4922 (3) | 0.1176 (7) | 0.0439 (13) | |
H4A | 0.381691 | 0.469170 | 0.037109 | 0.053* | |
H4B | 0.362214 | 0.517973 | 0.149924 | 0.053* | |
C5 | 0.4138 (3) | 0.4485 (3) | 0.2331 (7) | 0.0456 (14) | |
H5A | 0.386853 | 0.458252 | 0.314539 | 0.055* | |
H5B | 0.401546 | 0.407971 | 0.201822 | 0.055* | |
I1 | 0.63999 (2) | 0.68958 (2) | 1.00445 (6) | 0.03902 (14) | |
O1 | 0.5030 (2) | 0.65445 (17) | 0.4344 (4) | 0.0364 (8) | |
H1 | 0.518 (3) | 0.623 (2) | 0.402 (7) | 0.05 (2)* | |
C11 | 0.5320 (2) | 0.6593 (2) | 0.5604 (6) | 0.0293 (10) | |
C12 | 0.5220 (3) | 0.7116 (2) | 0.6361 (6) | 0.0352 (11) | |
H12 | 0.494289 | 0.741464 | 0.600328 | 0.042* | |
C13 | 0.5518 (2) | 0.72031 (19) | 0.7624 (7) | 0.0330 (10) | |
H13 | 0.544963 | 0.756109 | 0.813067 | 0.040* | |
C14 | 0.5920 (2) | 0.6759 (2) | 0.8149 (6) | 0.0293 (10) | |
C15 | 0.6015 (2) | 0.6234 (2) | 0.7428 (7) | 0.0312 (9) | |
H15 | 0.628314 | 0.593158 | 0.780345 | 0.037* | |
C16 | 0.5715 (2) | 0.6147 (2) | 0.6143 (6) | 0.0309 (10) | |
H16 | 0.578032 | 0.578773 | 0.564169 | 0.037* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.038 (2) | 0.028 (2) | 0.022 (2) | −0.0009 (16) | −0.0024 (17) | 0.0024 (16) |
N2 | 0.031 (2) | 0.045 (2) | 0.025 (2) | 0.0090 (19) | 0.0002 (17) | 0.0008 (18) |
C1 | 0.047 (4) | 0.035 (4) | 0.023 (3) | −0.008 (3) | 0.000 | 0.000 |
C2 | 0.050 (3) | 0.038 (3) | 0.036 (3) | 0.015 (3) | −0.006 (2) | 0.004 (2) |
C3 | 0.032 (3) | 0.061 (4) | 0.022 (3) | 0.011 (3) | 0.000 | 0.000 |
C4 | 0.026 (2) | 0.067 (4) | 0.038 (3) | 0.007 (2) | −0.003 (2) | 0.002 (3) |
C5 | 0.039 (3) | 0.050 (3) | 0.048 (4) | −0.007 (2) | −0.001 (3) | 0.002 (3) |
I1 | 0.0425 (2) | 0.03403 (19) | 0.0405 (2) | −0.00169 (13) | −0.00853 (15) | −0.00435 (16) |
O1 | 0.044 (2) | 0.0297 (18) | 0.0355 (19) | 0.0035 (16) | −0.0077 (17) | −0.0043 (16) |
C11 | 0.024 (2) | 0.030 (2) | 0.034 (2) | −0.0028 (18) | 0.0035 (19) | 0.0018 (19) |
C12 | 0.035 (3) | 0.029 (2) | 0.041 (3) | 0.005 (2) | 0.001 (2) | 0.000 (2) |
C13 | 0.037 (2) | 0.0255 (19) | 0.036 (3) | 0.0028 (18) | 0.007 (2) | −0.005 (3) |
C14 | 0.027 (2) | 0.032 (2) | 0.030 (2) | −0.0029 (19) | 0.003 (2) | 0.000 (2) |
C15 | 0.030 (2) | 0.027 (2) | 0.036 (3) | 0.0023 (16) | 0.001 (2) | 0.001 (2) |
C16 | 0.033 (2) | 0.024 (2) | 0.036 (2) | −0.0012 (18) | 0.002 (2) | −0.002 (2) |
Geometric parameters (Å, º) top
N1—C1 | 1.458 (5) | C5—H5A | 0.9900 |
N1—C5i | 1.474 (7) | C5—H5B | 0.9900 |
N1—C2 | 1.478 (7) | I1—C14 | 2.106 (5) |
N2—C2 | 1.440 (8) | O1—C11 | 1.361 (6) |
N2—C3 | 1.453 (6) | O1—H1 | 0.838 (14) |
N2—C4 | 1.472 (8) | C11—C16 | 1.395 (7) |
C1—H1A | 0.9900 | C11—C12 | 1.397 (8) |
C1—H1B | 0.9900 | C12—C13 | 1.381 (9) |
C2—H2A | 0.9900 | C12—H12 | 0.9500 |
C2—H2B | 0.9900 | C13—C14 | 1.398 (8) |
C3—H3A | 0.9900 | C13—H13 | 0.9500 |
C3—H3B | 0.9900 | C14—C15 | 1.382 (7) |
C4—C5 | 1.520 (9) | C15—C16 | 1.401 (8) |
C4—H4A | 0.9900 | C15—H15 | 0.9500 |
C4—H4B | 0.9900 | C16—H16 | 0.9500 |
| | | |
C1—N1—C5i | 112.8 (4) | C5—C4—H4B | 108.2 |
C1—N1—C2 | 115.3 (4) | H4A—C4—H4B | 107.3 |
C5i—N1—C2 | 114.4 (5) | N1i—C5—C4 | 116.4 (5) |
C2—N2—C3 | 114.5 (4) | N1i—C5—H5A | 108.2 |
C2—N2—C4 | 115.1 (5) | C4—C5—H5A | 108.2 |
C3—N2—C4 | 114.4 (4) | N1i—C5—H5B | 108.2 |
N1—C1—N1i | 119.2 (6) | C4—C5—H5B | 108.2 |
N1—C1—H1A | 107.5 | H5A—C5—H5B | 107.3 |
N1i—C1—H1A | 107.5 | C11—O1—H1 | 103 (5) |
N1—C1—H1B | 107.5 | O1—C11—C16 | 122.6 (5) |
N1i—C1—H1B | 107.5 | O1—C11—C12 | 117.7 (5) |
H1A—C1—H1B | 107.0 | C16—C11—C12 | 119.6 (5) |
N2—C2—N1 | 119.8 (4) | C13—C12—C11 | 120.8 (5) |
N2—C2—H2A | 107.4 | C13—C12—H12 | 119.6 |
N1—C2—H2A | 107.4 | C11—C12—H12 | 119.6 |
N2—C2—H2B | 107.4 | C12—C13—C14 | 119.3 (5) |
N1—C2—H2B | 107.4 | C12—C13—H13 | 120.4 |
H2A—C2—H2B | 106.9 | C14—C13—H13 | 120.4 |
N2—C3—N2i | 118.8 (7) | C15—C14—C13 | 120.8 (5) |
N2—C3—H3A | 107.6 | C15—C14—I1 | 119.5 (4) |
N2i—C3—H3A | 107.6 | C13—C14—I1 | 119.8 (4) |
N2—C3—H3B | 107.6 | C14—C15—C16 | 119.8 (5) |
N2i—C3—H3B | 107.6 | C14—C15—H15 | 120.1 |
H3A—C3—H3B | 107.0 | C16—C15—H15 | 120.1 |
N2—C4—C5 | 116.5 (5) | C11—C16—C15 | 119.7 (5) |
N2—C4—H4A | 108.2 | C11—C16—H16 | 120.2 |
C5—C4—H4A | 108.2 | C15—C16—H16 | 120.2 |
N2—C4—H4B | 108.2 | | |
| | | |
C5i—N1—C1—N1i | −82.7 (4) | O1—C11—C12—C13 | −177.7 (5) |
C2—N1—C1—N1i | 51.3 (3) | C16—C11—C12—C13 | 1.5 (8) |
C3—N2—C2—N1 | −55.1 (7) | C11—C12—C13—C14 | −0.5 (8) |
C4—N2—C2—N1 | 80.5 (7) | C12—C13—C14—C15 | −0.9 (8) |
C1—N1—C2—N2 | −50.6 (7) | C12—C13—C14—I1 | 178.2 (4) |
C5i—N1—C2—N2 | 82.6 (7) | C13—C14—C15—C16 | 1.3 (8) |
C2—N2—C3—N2i | 53.6 (4) | I1—C14—C15—C16 | −177.8 (4) |
C4—N2—C3—N2i | −82.3 (4) | O1—C11—C16—C15 | 178.1 (5) |
C2—N2—C4—C5 | −65.6 (7) | C12—C11—C16—C15 | −1.1 (8) |
C3—N2—C4—C5 | 70.1 (7) | C14—C15—C16—C11 | −0.3 (8) |
N2—C4—C5—N1i | −3.8 (8) | | |
Symmetry code: (i) −x+1, −y+1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.84 (1) | 1.96 (4) | 2.741 (6) | 154 (7) |
C5—H5B···I1ii | 0.99 | 3.03 | 3.961 (7) | 158 |
C13—H13···O1iii | 0.95 | 2.53 | 3.455 (6) | 165 |
Symmetry codes: (ii) −x+1, −y+1, z−1; (iii) −x+1, −y+3/2, z+1/2. |