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The title binary complex, 2C6H6O2·C6H12N4, is constructed from hexa­methyl­ene­tetra­mine, positioned about a twofold symmetry operator, and 1,2-dihydroxy­benzene. Each of the four tertiary amine N atoms participates in O—H...N contacts that produce mol­ecular strands that propagate along the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046204/tk2096sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046204/tk2096Isup2.hkl
Contains datablock I

CCDC reference: 630490

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.051
  • wR factor = 0.119
  • Data-to-parameter ratio = 12.8

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.21 Ratio PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C6 H12 N4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: XSCANS (Bruker, 1999); cell refinement: XSCANS; data reduction: XPREP (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: X-SEED.

Bis(1,2-dihydroxybenzene) hexamethylenetetramine top
Crystal data top
2C6H6O2·C6H12N4F(000) = 768
Mr = 360.41Dx = 1.326 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 33 reflections
a = 23.794 (2) Åθ = 20.4–22.6°
b = 6.8422 (5) ŵ = 0.10 mm1
c = 13.244 (1) ÅT = 298 K
β = 123.135 (6)°Plate, transparent colorless
V = 1805.5 (3) Å30.41 × 0.41 × 0.20 mm
Z = 4
Data collection top
Siemens P4
diffractometer
Rint = 0.022
Radiation source: fine-focus sealed tubeθmax = 25.4°, θmin = 2.0°
Graphite monochromatorh = 128
ω/2θ\ scansk = 18
1921 measured reflectionsl = 1413
1626 independent reflections3 standard reflections every 97 reflections
1054 reflections with I > 2σ(I) intensity decay: none
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0478P)2 + 0.6351P]
where P = (Fo2 + 2Fc2)/3
1626 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.25 e Å3
Special details top

Experimental. 1H NMR (acetone-d6): δ 4.63 (s, 12H, HMTA-CH2), 6.62 (dd, J = 5.8 and 3.5?Hz, 4H, H-2, 5), 6.78 (dd, J = 5.8 and 3.5?Hz, 4H, H-3, 4). 13 C NMR (acetone-d6): δ 145.6 (C7—C10), 119.4 (C3, 4), 115.7 (C2, 5), 74.4 (C1, 6).

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)
O10.08901 (9)0.7382 (3)0.13606 (15)0.0616 (6)
O20.11329 (11)0.4389 (3)0.03014 (17)0.0643 (6)
N10.04573 (9)1.0108 (3)0.23315 (15)0.0393 (5)
N20.04092 (9)1.2620 (3)0.35904 (15)0.0386 (5)
C10.13760 (11)0.6071 (4)0.2089 (2)0.0410 (6)
C20.17460 (12)0.6174 (4)0.3328 (2)0.0470 (6)
H20.16620.71690.37070.056*
C30.22395 (12)0.4820 (4)0.4012 (2)0.0558 (8)
H30.24890.49030.48490.067*
C40.23609 (13)0.3361 (4)0.3459 (2)0.0613 (8)
H40.26960.24500.39190.074*
C50.19892 (13)0.3225 (4)0.2220 (2)0.0562 (7)
H50.20720.22150.18490.067*
C60.14958 (12)0.4572 (4)0.1527 (2)0.0433 (6)
C70.08446 (11)1.1372 (4)0.3404 (2)0.0438 (6)
H7A0.11151.05600.41110.053*
H7B0.11461.21880.33090.053*
C80.00001.3817 (5)0.25000.0412 (8)
H8A0.02931.46520.26060.049*0.50
H8B0.02931.46520.23940.049*0.50
C90.00435 (12)1.1370 (3)0.37265 (19)0.0419 (6)
H9A0.03351.21830.38490.050*
H9B0.02191.05580.44370.050*
C100.00000.8920 (5)0.25000.0450 (9)
H10A0.02630.80850.18020.054*0.50
H10B0.02630.80850.31980.054*0.50
H1O0.0839 (15)0.827 (4)0.182 (3)0.086 (10)*
H2O0.0902 (15)0.530 (5)0.003 (3)0.077 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0695 (13)0.0651 (13)0.0405 (10)0.0360 (11)0.0238 (9)0.0047 (9)
O20.0907 (16)0.0549 (13)0.0490 (11)0.0317 (12)0.0393 (11)0.0079 (10)
N10.0423 (11)0.0358 (10)0.0401 (11)0.0073 (9)0.0227 (9)0.0017 (9)
N20.0469 (11)0.0335 (11)0.0399 (10)0.0099 (10)0.0265 (9)0.0072 (9)
C10.0390 (13)0.0429 (14)0.0456 (13)0.0089 (12)0.0260 (12)0.0081 (12)
C20.0466 (15)0.0498 (16)0.0451 (14)0.0014 (13)0.0255 (12)0.0011 (12)
C30.0444 (15)0.070 (2)0.0461 (15)0.0018 (15)0.0205 (13)0.0145 (14)
C40.0513 (17)0.071 (2)0.0639 (18)0.0229 (15)0.0333 (15)0.0320 (16)
C50.0680 (17)0.0494 (16)0.0699 (18)0.0219 (14)0.0496 (16)0.0165 (14)
C60.0490 (14)0.0455 (15)0.0457 (14)0.0104 (13)0.0324 (12)0.0098 (12)
C70.0377 (13)0.0458 (15)0.0439 (13)0.0001 (12)0.0197 (11)0.0013 (12)
C80.055 (2)0.0278 (17)0.0518 (19)0.0000.0362 (18)0.000
C90.0535 (14)0.0384 (13)0.0392 (12)0.0080 (12)0.0288 (12)0.0025 (11)
C100.058 (2)0.0240 (17)0.0426 (18)0.0000.0211 (17)0.000
Geometric parameters (Å, º) top
O1—C11.361 (3)C4—C51.377 (4)
O1—H1O0.91 (3)C4—H40.9300
O2—C61.365 (3)C5—C61.375 (3)
O2—H2O0.79 (3)C5—H50.9300
N1—C101.470 (3)C7—H7A0.9700
N1—C9i1.473 (3)C7—H7B0.9700
N1—C71.478 (3)C8—N2i1.472 (2)
N2—C91.462 (3)C8—H8A0.9700
N2—C71.464 (3)C8—H8B0.9700
N2—C81.472 (2)C9—N1i1.473 (3)
C1—C21.376 (3)C9—H9A0.9700
C1—C61.386 (3)C9—H9B0.9700
C2—C31.376 (3)C10—N1i1.470 (3)
C2—H20.9300C10—H10A0.9700
C3—C41.360 (4)C10—H10B0.9700
C3—H30.9300
C1—O1—H1O109.7 (18)C5—C6—C1119.3 (2)
C6—O2—H2O112 (2)N2—C7—N1112.12 (17)
C10—N1—C9i107.64 (16)N2—C7—H7A109.2
C10—N1—C7107.58 (16)N1—C7—H7A109.2
C9i—N1—C7108.21 (17)N2—C7—H7B109.2
C9—N2—C7108.47 (18)N1—C7—H7B109.2
C9—N2—C8108.04 (16)H7A—C7—H7B107.9
C7—N2—C8107.97 (15)N2i—C8—N2112.4 (2)
O1—C1—C2123.6 (2)N2i—C8—H8A109.1
O1—C1—C6116.8 (2)N2—C8—H8A109.1
C2—C1—C6119.6 (2)N2i—C8—H8B109.1
C1—C2—C3120.6 (3)N2—C8—H8B109.1
C1—C2—H2119.7H8A—C8—H8B107.9
C3—C2—H2119.7N2—C9—N1i112.35 (17)
C4—C3—C2119.7 (2)N2—C9—H9A109.1
C4—C3—H3120.1N1i—C9—H9A109.1
C2—C3—H3120.1N2—C9—H9B109.1
C3—C4—C5120.3 (2)N1i—C9—H9B109.1
C3—C4—H4119.9H9A—C9—H9B107.9
C5—C4—H4119.9N1i—C10—N1112.8 (3)
C6—C5—C4120.5 (3)N1i—C10—H10A109.0
C6—C5—H5119.7N1—C10—H10A109.0
C4—C5—H5119.7N1i—C10—H10B109.0
O2—C6—C5119.1 (2)N1—C10—H10B109.0
O2—C6—C1121.6 (2)H10A—C10—H10B107.8
O1—C1—C2—C3178.7 (2)C9—N2—C7—N158.6 (2)
C6—C1—C2—C30.9 (4)C8—N2—C7—N158.2 (2)
C1—C2—C3—C40.3 (4)C10—N1—C7—N258.0 (2)
C2—C3—C4—C50.5 (4)C9i—N1—C7—N258.0 (2)
C3—C4—C5—C60.6 (4)C9—N2—C8—N2i58.50 (13)
C4—C5—C6—O2179.5 (2)C7—N2—C8—N2i58.63 (13)
C4—C5—C6—C10.0 (4)C7—N2—C9—N1i58.7 (2)
O1—C1—C6—O21.6 (4)C8—N2—C9—N1i58.1 (2)
C2—C1—C6—O2178.8 (2)C9i—N1—C10—N1i58.19 (13)
O1—C1—C6—C5178.9 (2)C7—N1—C10—N1i58.22 (13)
C2—C1—C6—C50.8 (4)
Symmetry code: (i) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···N10.91 (3)1.89 (3)2.764 (3)162 (3)
O2—H2O···O10.79 (3)2.34 (3)2.717 (3)111 (2)
O2—H2O···N2ii0.79 (3)2.10 (3)2.832 (3)155 (3)
Symmetry code: (ii) x, y+2, z1/2.
 

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