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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989017014943/sj5537sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989017014943/sj5537Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989017014943/sj5537Isup3.cml
Supplementary material

CCDC reference: 1580038

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](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

Computing details top

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[4.4.1.13,8]dodecane–4-iodophenol (1/2) top
Crystal data top
C8H16N4·2C6H5IODx = 1.791 Mg m3
Mr = 608.25Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Fdd2Cell parameters from 15571 reflections
a = 20.8869 (16) Åθ = 3.6–25.9°
b = 22.4197 (13) ŵ = 2.81 mm1
c = 9.6352 (6) ÅT = 173 K
V = 4512.0 (5) Å3Block, yellow
Z = 80.24 × 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 sourceRint = 0.029
ω scansθmax = 25.5°, θmin = 3.6°
Absorption correction: multi-scan
(X-AREA; Stoe & Cie, 2001)
h = 2425
Tmin = 0.548, Tmax = 1.000k = 2627
7213 measured reflectionsl = 1111
2102 independent reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH 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 = 1.06Δρmax = 0.25 e Å3
2102 reflectionsΔρmin = 0.67 e Å3
132 parametersAbsolute structure: Classical Flack (1983) method preferred over Parsons because s.u. lower
2 restraintsAbsolute 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
xyzUiso*/UeqOcc. (<1)
N10.5189 (2)0.55327 (17)0.2785 (4)0.0293 (9)
N20.4501 (2)0.5309 (2)0.0695 (5)0.0335 (9)
C10.5000000.5000000.3551 (8)0.0350 (16)
H1A0.4638250.5111420.4162300.042*0.5
H1B0.5361760.4888580.4162290.042*0.5
C20.4734 (3)0.5730 (3)0.1705 (6)0.0413 (13)
H2A0.4355850.5899270.2185430.050*
H2B0.4938470.6061190.1190810.050*
C30.5000000.5000000.0073 (9)0.0383 (16)
H3A0.5211090.5295650.0683310.046*0.5
H3B0.4788910.4704370.0683360.046*0.5
C40.3977 (3)0.4922 (3)0.1176 (7)0.0439 (13)
H4A0.3816910.4691700.0371090.053*
H4B0.3622140.5179730.1499240.053*
C50.4138 (3)0.4485 (3)0.2331 (7)0.0456 (14)
H5A0.3868530.4582520.3145390.055*
H5B0.4015460.4079710.2018220.055*
I10.63999 (2)0.68958 (2)1.00445 (6)0.03902 (14)
O10.5030 (2)0.65445 (17)0.4344 (4)0.0364 (8)
H10.518 (3)0.623 (2)0.402 (7)0.05 (2)*
C110.5320 (2)0.6593 (2)0.5604 (6)0.0293 (10)
C120.5220 (3)0.7116 (2)0.6361 (6)0.0352 (11)
H120.4942890.7414640.6003280.042*
C130.5518 (2)0.72031 (19)0.7624 (7)0.0330 (10)
H130.5449630.7561090.8130670.040*
C140.5920 (2)0.6759 (2)0.8149 (6)0.0293 (10)
C150.6015 (2)0.6234 (2)0.7428 (7)0.0312 (9)
H150.6283140.5931580.7803450.037*
C160.5715 (2)0.6147 (2)0.6143 (6)0.0309 (10)
H160.5780320.5787730.5641690.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.038 (2)0.028 (2)0.022 (2)0.0009 (16)0.0024 (17)0.0024 (16)
N20.031 (2)0.045 (2)0.025 (2)0.0090 (19)0.0002 (17)0.0008 (18)
C10.047 (4)0.035 (4)0.023 (3)0.008 (3)0.0000.000
C20.050 (3)0.038 (3)0.036 (3)0.015 (3)0.006 (2)0.004 (2)
C30.032 (3)0.061 (4)0.022 (3)0.011 (3)0.0000.000
C40.026 (2)0.067 (4)0.038 (3)0.007 (2)0.003 (2)0.002 (3)
C50.039 (3)0.050 (3)0.048 (4)0.007 (2)0.001 (3)0.002 (3)
I10.0425 (2)0.03403 (19)0.0405 (2)0.00169 (13)0.00853 (15)0.00435 (16)
O10.044 (2)0.0297 (18)0.0355 (19)0.0035 (16)0.0077 (17)0.0043 (16)
C110.024 (2)0.030 (2)0.034 (2)0.0028 (18)0.0035 (19)0.0018 (19)
C120.035 (3)0.029 (2)0.041 (3)0.005 (2)0.001 (2)0.000 (2)
C130.037 (2)0.0255 (19)0.036 (3)0.0028 (18)0.007 (2)0.005 (3)
C140.027 (2)0.032 (2)0.030 (2)0.0029 (19)0.003 (2)0.000 (2)
C150.030 (2)0.027 (2)0.036 (3)0.0023 (16)0.001 (2)0.001 (2)
C160.033 (2)0.024 (2)0.036 (2)0.0012 (18)0.002 (2)0.002 (2)
Geometric parameters (Å, º) top
N1—C11.458 (5)C5—H5A0.9900
N1—C5i1.474 (7)C5—H5B0.9900
N1—C21.478 (7)I1—C142.106 (5)
N2—C21.440 (8)O1—C111.361 (6)
N2—C31.453 (6)O1—H10.838 (14)
N2—C41.472 (8)C11—C161.395 (7)
C1—H1A0.9900C11—C121.397 (8)
C1—H1B0.9900C12—C131.381 (9)
C2—H2A0.9900C12—H120.9500
C2—H2B0.9900C13—C141.398 (8)
C3—H3A0.9900C13—H130.9500
C3—H3B0.9900C14—C151.382 (7)
C4—C51.520 (9)C15—C161.401 (8)
C4—H4A0.9900C15—H150.9500
C4—H4B0.9900C16—H160.9500
C1—N1—C5i112.8 (4)C5—C4—H4B108.2
C1—N1—C2115.3 (4)H4A—C4—H4B107.3
C5i—N1—C2114.4 (5)N1i—C5—C4116.4 (5)
C2—N2—C3114.5 (4)N1i—C5—H5A108.2
C2—N2—C4115.1 (5)C4—C5—H5A108.2
C3—N2—C4114.4 (4)N1i—C5—H5B108.2
N1—C1—N1i119.2 (6)C4—C5—H5B108.2
N1—C1—H1A107.5H5A—C5—H5B107.3
N1i—C1—H1A107.5C11—O1—H1103 (5)
N1—C1—H1B107.5O1—C11—C16122.6 (5)
N1i—C1—H1B107.5O1—C11—C12117.7 (5)
H1A—C1—H1B107.0C16—C11—C12119.6 (5)
N2—C2—N1119.8 (4)C13—C12—C11120.8 (5)
N2—C2—H2A107.4C13—C12—H12119.6
N1—C2—H2A107.4C11—C12—H12119.6
N2—C2—H2B107.4C12—C13—C14119.3 (5)
N1—C2—H2B107.4C12—C13—H13120.4
H2A—C2—H2B106.9C14—C13—H13120.4
N2—C3—N2i118.8 (7)C15—C14—C13120.8 (5)
N2—C3—H3A107.6C15—C14—I1119.5 (4)
N2i—C3—H3A107.6C13—C14—I1119.8 (4)
N2—C3—H3B107.6C14—C15—C16119.8 (5)
N2i—C3—H3B107.6C14—C15—H15120.1
H3A—C3—H3B107.0C16—C15—H15120.1
N2—C4—C5116.5 (5)C11—C16—C15119.7 (5)
N2—C4—H4A108.2C11—C16—H16120.2
C5—C4—H4A108.2C15—C16—H16120.2
N2—C4—H4B108.2
C5i—N1—C1—N1i82.7 (4)O1—C11—C12—C13177.7 (5)
C2—N1—C1—N1i51.3 (3)C16—C11—C12—C131.5 (8)
C3—N2—C2—N155.1 (7)C11—C12—C13—C140.5 (8)
C4—N2—C2—N180.5 (7)C12—C13—C14—C150.9 (8)
C1—N1—C2—N250.6 (7)C12—C13—C14—I1178.2 (4)
C5i—N1—C2—N282.6 (7)C13—C14—C15—C161.3 (8)
C2—N2—C3—N2i53.6 (4)I1—C14—C15—C16177.8 (4)
C4—N2—C3—N2i82.3 (4)O1—C11—C16—C15178.1 (5)
C2—N2—C4—C565.6 (7)C12—C11—C16—C151.1 (8)
C3—N2—C4—C570.1 (7)C14—C15—C16—C110.3 (8)
N2—C4—C5—N1i3.8 (8)
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.84 (1)1.96 (4)2.741 (6)154 (7)
C5—H5B···I1ii0.993.033.961 (7)158
C13—H13···O1iii0.952.533.455 (6)165
Symmetry codes: (ii) x+1, y+1, z1; (iii) x+1, y+3/2, z+1/2.
 

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