Cyclo­hexane-1,4-diammonium tetra­hydroxotetra­borate 2.5-hydrate

In the title compound, [C₆H₁₀(NH₃)₂]²⁺·[B₄O₅(OH)₄]²⁻·2.5H₂O, the asymmetric unit contains one anion, two half-cations and 2.5 water mol­ecules. Each cation is centrosymmetric. In the crystal structure, the anions are connected to each other via hydrogen bonding, forming a three-dimensional framework with recta­ngular channels, which are occupied by the templating organic amine cations and guest water mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
Some non-H atoms missing
• Disorder in main residue
• R factor = 0.049
• wR factor = 0.135
• Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSMU01_ALERT_1_B  The ratio of given/expected absorption coefficient lies
               outside the range 0.95 <> 1.05
            Calculated value of mu =     0.146
            Value of mu given      =     0.135
CHEMW01_ALERT_1_B  The ratio of given/expected molecular weight as calculated
            from the _chemical_formula_sum lies outside
            the range 0.95 <> 1.05
            Calculated formula weight =   380.5234
            Formula weight given      =   352.5200
PLAT417_ALERT_2_B Short Inter D-H..H-D       H4     ..  H6      ..       2.06 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H1H    ..  H2      ..       1.33 Ang.

Alert level C
CHEMW01_ALERT_1_C  The difference between the given and expected weight for
            compound is greater 1 mass unit. Check that all hydrogen
            atoms have been taken into account.
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
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT301_ALERT_3_C Main Residue  Disorder .........................       2.00 Perc.
PLAT353_ALERT_3_C Long    N-H Bond (0.87A)   N1     -   H6     ...       1.04 Ang.
PLAT353_ALERT_3_C Long    N-H Bond (0.87A)   N2     -   H9     ...       1.03 Ang.
PLAT417_ALERT_2_C Short Inter D-H..H-D       H2G    ..  H3D     ..       2.13 Ang.
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.14 Ratio
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C6 H16 N2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C6 H16 N2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              B4 H4 O9
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          4
              H2 O
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          5
              H2 O

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C6 H25 B4 N4 O11.5
            Atom count from _chemical_formula_moiety:C6 H25 B4 N2 O11.5
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C6 H25 B4 N4 O11.5
            Atom count from the _atom_site data:  C6 H25 B4 N2 O11.5
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: Large difference may be due to a
            symmetry error - see SYMMG tests
           From the CIF: _cell_formula_units_Z    2
           From the CIF: _chemical_formula_sum  C6 H25 B4 N4 O11.5
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         12.00     12.00    0.00
           H         50.00     50.00    0.00
           B          8.00      8.00    0.00
           N          8.00      4.00    4.00
           O         23.00     23.00    0.00

   0 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
  15 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

  10 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
   3 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Cyclohexane-1,4-diammonium tetrahydroxotetraborate 2.5-hydrate

Crystal data

C6H16N2^2+·B4H4O9^2^−·2.5H2O	Z = 2
Mr = 352.52	F(000) = 374
Triclinic, P1	Dx = 1.512 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3581 (4) Å	Cell parameters from 3179 reflections
b = 9.9625 (5) Å	θ = 2.4–26.5°
c = 10.8064 (2) Å	µ = 0.14 mm^−1
α = 110.517 (3)°	T = 294 K
β = 108.380 (2)°	Prism, colorless
γ = 96.470 (5)°	0.25 × 0.22 × 0.10 mm
V = 774.12 (6) Å^3

Data collection

Siemens SMART CCD area-dedector diffractometer	3179 independent reflections
Radiation source: fine-focus sealed tube	2526 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
φ and ω scans	θmax = 26.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.967, Tmax = 0.987	k = −12→8
5590 measured reflections	l = −11→13

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0652P)^2 + 0.4252P] where P = (Fo^2 + 2Fc^2)/3
3179 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.55 e Å^−3
15 restraints	Δρmin = −0.39 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)
B1	1.6013 (3)	1.7011 (3)	0.5106 (3)	0.0272 (5)
B2	1.3916 (3)	1.6556 (3)	0.2705 (3)	0.0260 (5)
B3	1.6260 (3)	1.6828 (3)	0.1821 (3)	0.0268 (5)
B4	1.6266 (3)	1.8777 (3)	0.4020 (3)	0.0248 (5)
O1	1.6584 (3)	1.6726 (2)	0.63005 (18)	0.0376 (4)
O2	1.2042 (2)	1.59781 (19)	0.20694 (18)	0.0366 (4)
H2	1.1795	1.5117	0.1491	0.055*
O3	1.7090 (2)	1.6376 (2)	0.08980 (19)	0.0364 (4)
O4	1.6766 (2)	2.03708 (17)	0.45242 (18)	0.0287 (4)
O5	1.4664 (2)	1.60562 (17)	0.38770 (17)	0.0308 (4)
O6	1.4708 (2)	1.59975 (17)	0.16121 (16)	0.0287 (4)
O7	1.71269 (19)	1.81393 (17)	0.29993 (17)	0.0290 (4)
O8	1.6889 (2)	1.83332 (17)	0.52380 (16)	0.0286 (4)
O9	1.43750 (19)	1.81723 (16)	0.32957 (16)	0.0256 (4)
N1	1.0406 (3)	0.7249 (2)	−0.6021 (2)	0.0336 (5)
N2	1.6859 (3)	1.0108 (3)	−0.1798 (3)	0.0451 (6)
C1	0.8796 (3)	0.4802 (3)	−0.6415 (3)	0.0396 (6)
H1A	0.9379	0.4328	−0.7032	0.048*
H1B	0.7725	0.4926	−0.7002	0.048*
C2	0.9960 (3)	0.6306 (3)	−0.5308 (3)	0.0313 (5)
H2A	0.9323	0.6793	−0.4733	0.038*
C3	1.1625 (3)	0.6175 (3)	−0.4318 (3)	0.0366 (6)
H3A	1.2312	0.7152	−0.3602	0.044*
H3B	1.2308	0.5749	−0.4861	0.044*
C4	1.5502 (4)	0.8674 (3)	−0.0751 (3)	0.0409 (6)
H4A	1.6635	0.8794	−0.0053	0.049*
H4B	1.5247	0.7766	−0.1587	0.049*
C5	1.5526 (3)	0.9979 (3)	−0.1163 (3)	0.0358 (6)
H5B	1.4378	0.9823	−0.1882	0.043*
C6	1.5882 (4)	1.1419 (3)	0.0124 (3)	0.0392 (6)
H6B	1.7023	1.1602	0.0844	0.047*
H6C	1.5880	1.2237	−0.0166	0.047*
O1W	1.0094 (3)	1.3048 (3)	−0.0041 (3)	0.0656 (6)
H1G	1.0883	1.2980	−0.0517	0.098*
H1H	1.0553	1.3851	0.0771	0.098*
O2W	1.0369 (4)	0.9823 (4)	−0.2793 (3)	0.1001 (11)
H2G	0.9178	0.9752	−0.3235	0.150*
H2F	1.1081	1.0444	−0.3015	0.150*
O3W	0.9944 (5)	1.0628 (5)	0.0626 (5)	0.0587 (11)	0.50
H3E	1.0340	1.1614	0.0671	0.088*	0.50
H3D	0.9902	1.0838	0.1475	0.088*	0.50
H7	1.086 (4)	0.673 (3)	−0.669 (3)	0.045 (8)*
H3	1.650 (4)	1.560 (4)	0.013 (4)	0.052 (9)*
H6	1.135 (4)	0.821 (4)	−0.527 (3)	0.053 (9)*
H4	1.630 (5)	2.075 (4)	0.516 (4)	0.063 (10)*
H5	0.944 (5)	0.753 (4)	−0.641 (4)	0.071 (11)*
H10	1.674 (5)	1.084 (4)	−0.218 (4)	0.073 (12)*
H1	1.606 (5)	1.595 (4)	0.625 (4)	0.068 (11)*
H9	1.676 (6)	0.909 (5)	−0.256 (5)	0.093 (14)*
H8	1.794 (6)	1.041 (5)	−0.116 (5)	0.084 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
B1	0.0298 (12)	0.0251 (12)	0.0288 (13)	0.0080 (10)	0.0158 (10)	0.0088 (10)
B2	0.0246 (12)	0.0243 (12)	0.0244 (12)	0.0014 (10)	0.0101 (10)	0.0054 (10)
B3	0.0246 (12)	0.0270 (12)	0.0253 (12)	0.0052 (10)	0.0080 (10)	0.0083 (10)
B4	0.0226 (11)	0.0230 (12)	0.0239 (12)	0.0016 (9)	0.0088 (10)	0.0056 (10)
O1	0.0467 (11)	0.0314 (10)	0.0301 (9)	0.0012 (8)	0.0125 (8)	0.0118 (8)
O2	0.0256 (8)	0.0336 (9)	0.0364 (9)	−0.0033 (7)	0.0105 (7)	0.0027 (8)
O3	0.0320 (9)	0.0348 (10)	0.0320 (9)	0.0000 (8)	0.0170 (8)	0.0003 (8)
O4	0.0304 (8)	0.0224 (8)	0.0308 (8)	0.0016 (7)	0.0150 (7)	0.0068 (7)
O5	0.0353 (9)	0.0246 (8)	0.0278 (8)	−0.0014 (7)	0.0121 (7)	0.0081 (7)
O6	0.0277 (8)	0.0275 (8)	0.0237 (8)	0.0002 (6)	0.0108 (6)	0.0038 (6)
O7	0.0226 (7)	0.0282 (8)	0.0290 (8)	0.0017 (6)	0.0111 (6)	0.0038 (7)
O8	0.0266 (8)	0.0251 (8)	0.0272 (8)	0.0004 (6)	0.0059 (6)	0.0086 (6)
O9	0.0221 (7)	0.0250 (8)	0.0261 (8)	0.0027 (6)	0.0102 (6)	0.0064 (6)
N1	0.0262 (10)	0.0306 (11)	0.0403 (12)	0.0009 (9)	0.0086 (9)	0.0160 (10)
N2	0.0425 (14)	0.0624 (17)	0.0319 (12)	0.0154 (12)	0.0180 (11)	0.0168 (12)
C1	0.0349 (13)	0.0359 (14)	0.0365 (13)	−0.0042 (11)	0.0026 (11)	0.0156 (11)
C2	0.0275 (11)	0.0288 (12)	0.0383 (13)	0.0040 (9)	0.0142 (10)	0.0140 (10)
C3	0.0284 (12)	0.0323 (13)	0.0398 (14)	−0.0027 (10)	0.0066 (10)	0.0132 (11)
C4	0.0487 (15)	0.0429 (15)	0.0338 (13)	0.0208 (13)	0.0178 (12)	0.0143 (12)
C5	0.0360 (13)	0.0484 (15)	0.0265 (12)	0.0153 (11)	0.0137 (10)	0.0161 (11)
C6	0.0462 (15)	0.0402 (14)	0.0331 (13)	0.0146 (12)	0.0144 (11)	0.0167 (11)
O1W	0.0632 (14)	0.0620 (14)	0.0742 (16)	0.0105 (12)	0.0355 (13)	0.0240 (13)
O2W	0.0638 (16)	0.133 (3)	0.0833 (19)	−0.0318 (16)	−0.0009 (14)	0.0649 (19)
O3W	0.046 (2)	0.073 (3)	0.062 (3)	0.013 (2)	0.015 (2)	0.038 (2)

Geometric parameters (Å, º)

B1—O5	1.367 (3)	C1—C2	1.518 (3)
B1—O1	1.368 (3)	C1—C3^i	1.529 (4)
B1—O8	1.370 (3)	C1—H1A	0.9700
B2—O2	1.449 (3)	C1—H1B	0.9700
B2—O9	1.460 (3)	C2—C3	1.516 (3)
B2—O5	1.502 (3)	C2—H2A	0.9800
B2—O6	1.503 (3)	C3—C1^i	1.529 (4)
B3—O6	1.364 (3)	C3—H3A	0.9700
B3—O3	1.368 (3)	C3—H3B	0.9700
B3—O7	1.375 (3)	C4—C5	1.515 (4)
B4—O4	1.447 (3)	C4—C6^ii	1.524 (4)
B4—O9	1.465 (3)	C4—H4A	0.9700
B4—O8	1.493 (3)	C4—H4B	0.9700
B4—O7	1.500 (3)	C5—C6	1.525 (4)
O1—H1	0.82 (4)	C5—H5B	0.9800
O2—H2	0.8200	C6—C4^ii	1.524 (4)
O3—H3	0.86 (4)	C6—H6B	0.9700
O4—H4	0.88 (4)	C6—H6C	0.9700
N1—C2	1.492 (3)	O1W—H1G	0.9506
N1—H7	0.95 (3)	O1W—H1H	0.8855
N1—H6	1.04 (3)	O2W—H2G	0.9408
N1—H5	0.92 (4)	O2W—H2F	0.9512
N2—C5	1.496 (3)	O3W—O3W^iii	1.525 (10)
N2—H10	0.96 (4)	O3W—H3E	0.9795
N2—H9	1.03 (5)	O3W—H3D	0.8790
N2—H8	0.90 (5)
O5—B1—O1	122.7 (2)	C2—C1—H1A	109.6
O5—B1—O8	122.4 (2)	C3^i—C1—H1A	109.6
O1—B1—O8	114.9 (2)	C2—C1—H1B	109.6
O2—B2—O9	110.55 (19)	C3^i—C1—H1B	109.6
O2—B2—O5	109.11 (19)	H1A—C1—H1B	108.1
O9—B2—O5	109.39 (18)	N1—C2—C3	109.23 (19)
O2—B2—O6	110.79 (18)	N1—C2—C1	110.4 (2)
O9—B2—O6	108.38 (18)	C3—C2—C1	111.9 (2)
O5—B2—O6	108.58 (18)	N1—C2—H2A	108.4
O6—B3—O3	121.9 (2)	C3—C2—H2A	108.4
O6—B3—O7	122.4 (2)	C1—C2—H2A	108.4
O3—B3—O7	115.6 (2)	C2—C3—C1^i	110.3 (2)
O4—B4—O9	112.39 (18)	C2—C3—H3A	109.6
O4—B4—O8	110.32 (18)	C1^i—C3—H3A	109.6
O9—B4—O8	108.36 (18)	C2—C3—H3B	109.6
O4—B4—O7	107.46 (18)	C1^i—C3—H3B	109.6
O9—B4—O7	109.54 (17)	H3A—C3—H3B	108.1
O8—B4—O7	108.70 (18)	C5—C4—C6^ii	109.4 (2)
B1—O1—H1	117 (3)	C5—C4—H4A	109.8
B2—O2—H2	109.5	C6^ii—C4—H4A	109.8
B3—O3—H3	115 (2)	C5—C4—H4B	109.8
B4—O4—H4	107 (2)	C6^ii—C4—H4B	109.8
B1—O5—B2	119.37 (18)	H4A—C4—H4B	108.2
B3—O6—B2	118.34 (17)	N2—C5—C4	111.3 (2)
B3—O7—B4	119.46 (18)	N2—C5—C6	109.6 (2)
B1—O8—B4	118.24 (18)	C4—C5—C6	111.0 (2)
B2—O9—B4	111.19 (17)	N2—C5—H5B	108.3
C2—N1—H7	109.4 (18)	C4—C5—H5B	108.3
C2—N1—H6	110.2 (17)	C6—C5—H5B	108.3
H7—N1—H6	108 (3)	C4^ii—C6—C5	110.3 (2)
C2—N1—H5	108 (2)	C4^ii—C6—H6B	109.6
H7—N1—H5	114 (3)	C5—C6—H6B	109.6
H6—N1—H5	107 (3)	C4^ii—C6—H6C	109.6
C5—N2—H10	110 (2)	C5—C6—H6C	109.6
C5—N2—H9	110 (2)	H6B—C6—H6C	108.1
H10—N2—H9	112 (3)	H1G—O1W—H1H	108.3
C5—N2—H8	113 (3)	H2G—O2W—H2F	112.0
H10—N2—H8	105 (3)	O3W^iii—O3W—H3E	113.7
H9—N2—H8	106 (4)	O3W^iii—O3W—H3D	141.8
C2—C1—C3^i	110.3 (2)	H3E—O3W—H3D	102.1

Symmetry codes: (i) −x+2, −y+1, −z−1; (ii) −x+3, −y+2, −z; (iii) −x+2, −y+2, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1G···O3^iv	0.95	1.96	2.858 (3)	157
O1W—H1H···O2	0.89	2.06	2.880 (3)	154
O2W—H2G···O8^v	0.94	2.04	2.846 (3)	143
O2W—H2F···O7^iv	0.95	1.93	2.864 (3)	167
O3W—H3E···O1W	0.98	1.85	2.749 (5)	152
O3W—H3D···O2W^iii	0.88	1.83	2.617 (5)	148
N1—H7···O2^vi	0.95 (3)	1.90 (3)	2.840 (3)	171 (3)
O3—H3···O6^iv	0.86 (4)	1.85 (4)	2.709 (2)	175 (3)
N1—H6···O4^iv	1.04 (3)	1.74 (3)	2.732 (3)	158 (3)
O4—H4···O9^vii	0.88 (4)	1.94 (4)	2.810 (2)	171 (3)
N1—H5···O7^v	0.91 (4)	2.06 (4)	2.965 (3)	170 (3)
N2—H10···O9^iv	0.96 (4)	1.90 (4)	2.813 (3)	158 (3)
O1—H1···O5^viii	0.82 (4)	1.97 (4)	2.767 (2)	166 (4)
N2—H9···O8^vi	1.03 (5)	2.27 (5)	3.079 (3)	134 (3)
N2—H8···O3W^ix	0.89 (5)	2.04 (5)	2.875 (5)	157 (4)

Symmetry codes: (iii) −x+2, −y+2, −z; (iv) −x+3, −y+3, −z; (v) x−1, y−1, z−1; (vi) x, y−1, z−1; (vii) −x+3, −y+4, −z+1; (viii) −x+3, −y+3, −z+1; (ix) x+1, y, z.