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The title salt, C8H20NO5+·C7H4NO4·H2O, is composed of a 4-nitro­benzoate anion, a [2-hydr­oxy-1,1-bis­(hydroxy­meth­yl)eth­yl]bis­(2-hydroxy­ethyl)ammonium (NBHHP) cation and a water mol­ecule. The three units are linked by O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806007276/fl6216sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806007276/fl6216Isup2.hkl
Contains datablock I

CCDC reference: 605068

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.050
  • wR factor = 0.141
  • Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT417_ALERT_2_C Short Inter D-H..H-D H2 .. H3 .. 2.14 Ang. PLAT482_ALERT_4_C Small D-H..A Angle Rep for C11 .. O6 .. 98.00 Deg. PLAT482_ALERT_4_C Small D-H..A Angle Rep for C12 .. O8 .. 97.00 Deg. PLAT482_ALERT_4_C Small D-H..A Angle Rep for C14 .. O9 .. 97.00 Deg. PLAT482_ALERT_4_C Small D-H..A Angle Rep for C15 .. O7 .. 98.00 Deg. PLAT748_ALERT_1_C D-H..A Calc 113.2(18), Rep 113.00 ...... Missing su N1 -H1N -O3 1.555 1.555 1.555 PLAT748_ALERT_1_C D-H..A Calc 109.6(18), Rep 110.00 ...... Missing su N1 -H1N -O4 1.555 1.555 1.555 PLAT748_ALERT_1_C D-H..A Calc 111.5(19), Rep 112.00 ...... Missing su N1 -H1N -O5 1.555 1.555 1.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 H2 O
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 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 1 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 5 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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, 2000); software used to prepare material for publication: SHELXL97.

[2-Hydroxy-1,1-bis(hydroxymethyl)ethyl]bis(2-hydroxyethyl)ammonium 4-nitrobenzoate monohydrate top
Crystal data top
C8H20NO5+·C7H4NO4·H2OZ = 2
Mr = 394.38F(000) = 420
Triclinic, P1Dx = 1.427 Mg m3
Dm = 1.427 Mg m3
Dm measured by not measured
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.5419 (6) ÅCell parameters from 2504 reflections
b = 11.5935 (10) Åθ = 3.0–24.6°
c = 13.4632 (12) ŵ = 0.12 mm1
α = 67.290 (2)°T = 298 K
β = 77.302 (2)°Block, colorless
γ = 82.612 (2)°0.37 × 0.29 × 0.26 mm
V = 917.81 (14) Å3
Data collection top
Bruker APEX area-detector
diffractometer
3242 independent reflections
Radiation source: normal-focus sealed tube2739 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.011
φ and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS, Bruker, 2000)
h = 77
Tmin = 0.953, Tmax = 0.965k = 1213
4825 measured reflectionsl = 1516
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0803P)2 + 0.3186P]
where P = (Fo2 + 2Fc2)/3
3242 reflections(Δ/σ)max < 0.001
258 parametersΔρmax = 0.46 e Å3
4 restraintsΔρmin = 0.25 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*/Ueq
O10.3903 (2)0.24087 (13)0.21437 (13)0.0502 (4)
H10.35100.30510.22640.075*
O20.7053 (2)0.48794 (12)0.10816 (12)0.0450 (4)
H20.61620.51260.14980.067*
O31.0929 (2)0.29794 (13)0.00637 (12)0.0498 (4)
H31.15110.36460.03400.075*
O41.1358 (2)0.04374 (15)0.33119 (15)0.0585 (4)
H41.22740.09260.29290.088*
O51.1888 (3)0.00643 (15)0.08718 (14)0.0642 (5)
H51.28890.04010.10810.096*
O60.2025 (3)0.43071 (16)0.26168 (15)0.0629 (5)
O70.4216 (2)0.57659 (15)0.23160 (14)0.0575 (4)
O80.5679 (3)0.7061 (2)0.54362 (18)0.0816 (6)
O90.3545 (3)0.84234 (17)0.52647 (16)0.0724 (5)
O101.5201 (3)0.17079 (17)0.12201 (18)0.0728 (5)
N10.8513 (2)0.14766 (14)0.17532 (12)0.0331 (4)
N20.3965 (3)0.75195 (18)0.51016 (15)0.0519 (5)
C10.5229 (3)0.27107 (19)0.11093 (17)0.0411 (5)
H1A0.47530.35160.06220.049*
H1B0.51070.20920.08070.049*
C20.7846 (3)0.36638 (17)0.16754 (15)0.0366 (4)
H2A0.71090.33790.24300.044*
H2B0.93260.36840.16710.044*
C30.8751 (3)0.32105 (19)0.00461 (15)0.0410 (5)
H3A0.83020.27750.04420.049*
H3B0.84520.41000.04090.049*
C40.7533 (3)0.27667 (16)0.11354 (14)0.0324 (4)
C50.7854 (3)0.09815 (17)0.29953 (14)0.0358 (4)
H5A0.65680.14280.31900.043*
H5B0.75620.01040.32530.043*
C60.9494 (3)0.11183 (19)0.35648 (16)0.0415 (5)
H6A0.97740.19950.33270.050*
H6B0.89900.08040.43510.050*
C70.8240 (4)0.04910 (19)0.13217 (18)0.0483 (5)
H7A0.69100.01050.16890.058*
H7B0.82200.08800.05430.058*
C81.0004 (4)0.0496 (2)0.15127 (19)0.0569 (6)
H8A1.01060.08410.22820.068*
H8B0.97440.11710.13070.068*
C90.2478 (3)0.52647 (18)0.27033 (16)0.0413 (5)
C100.0783 (3)0.58862 (17)0.33189 (15)0.0381 (4)
C110.1278 (3)0.5587 (2)0.3511 (2)0.0509 (5)
H110.16170.50180.32460.061*
C120.2841 (3)0.6123 (2)0.4091 (2)0.0527 (6)
H120.42320.59270.42140.063*
C130.2306 (3)0.69510 (18)0.44811 (15)0.0408 (5)
C140.0276 (3)0.7274 (2)0.43053 (17)0.0460 (5)
H140.00540.78400.45760.055*
C150.1265 (3)0.6735 (2)0.37147 (17)0.0450 (5)
H150.26500.69460.35810.054*
H1N0.984 (3)0.159 (2)0.1612 (19)0.054*
H10A1.489 (3)0.2450 (17)0.1584 (17)0.054*
H10B1.628 (3)0.164 (2)0.0760 (16)0.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0381 (8)0.0442 (8)0.0587 (9)0.0028 (6)0.0084 (6)0.0177 (7)
O20.0436 (8)0.0306 (7)0.0506 (8)0.0014 (6)0.0023 (6)0.0109 (6)
O30.0384 (8)0.0396 (8)0.0532 (9)0.0007 (6)0.0086 (6)0.0071 (7)
O40.0432 (9)0.0549 (9)0.0784 (12)0.0011 (7)0.0114 (8)0.0271 (9)
O50.0750 (11)0.0514 (9)0.0558 (10)0.0166 (8)0.0051 (9)0.0183 (8)
O60.0567 (10)0.0555 (10)0.0835 (12)0.0051 (8)0.0075 (8)0.0437 (9)
O70.0412 (9)0.0536 (9)0.0767 (11)0.0003 (7)0.0050 (7)0.0324 (8)
O80.0544 (11)0.1000 (15)0.0917 (14)0.0081 (10)0.0196 (10)0.0532 (12)
O90.0824 (13)0.0628 (11)0.0714 (12)0.0012 (9)0.0134 (9)0.0399 (10)
O100.0590 (11)0.0555 (10)0.0868 (14)0.0005 (8)0.0097 (9)0.0214 (10)
N10.0348 (8)0.0324 (8)0.0290 (8)0.0015 (6)0.0023 (6)0.0111 (6)
N20.0539 (12)0.0520 (11)0.0417 (10)0.0035 (9)0.0041 (8)0.0174 (8)
C10.0333 (10)0.0432 (11)0.0468 (11)0.0017 (8)0.0063 (8)0.0182 (9)
C20.0361 (10)0.0327 (9)0.0380 (10)0.0007 (7)0.0036 (8)0.0122 (8)
C30.0425 (11)0.0405 (10)0.0317 (10)0.0000 (8)0.0016 (8)0.0081 (8)
C40.0331 (9)0.0300 (9)0.0304 (9)0.0018 (7)0.0042 (7)0.0089 (7)
C50.0396 (10)0.0339 (9)0.0278 (9)0.0026 (7)0.0004 (7)0.0085 (7)
C60.0467 (11)0.0416 (11)0.0335 (10)0.0010 (8)0.0063 (8)0.0118 (8)
C70.0679 (14)0.0401 (11)0.0431 (11)0.0048 (10)0.0122 (10)0.0236 (9)
C80.0813 (17)0.0383 (11)0.0473 (12)0.0108 (11)0.0056 (11)0.0193 (10)
C90.0422 (11)0.0382 (11)0.0412 (11)0.0052 (8)0.0086 (9)0.0139 (8)
C100.0392 (10)0.0350 (10)0.0367 (10)0.0041 (8)0.0073 (8)0.0114 (8)
C110.0456 (12)0.0519 (13)0.0639 (14)0.0041 (9)0.0050 (10)0.0332 (11)
C120.0350 (11)0.0591 (14)0.0664 (14)0.0043 (9)0.0002 (10)0.0300 (12)
C130.0442 (11)0.0391 (10)0.0320 (10)0.0047 (8)0.0021 (8)0.0105 (8)
C140.0498 (12)0.0477 (12)0.0457 (12)0.0009 (9)0.0100 (9)0.0235 (10)
C150.0363 (10)0.0509 (12)0.0505 (12)0.0005 (9)0.0076 (9)0.0229 (10)
Geometric parameters (Å, º) top
O1—C11.409 (2)C2—H2B0.9700
O1—H10.8200C3—C41.532 (2)
O2—C21.421 (2)C3—H3A0.9700
O2—H20.8200C3—H3B0.9700
O3—C31.412 (2)C5—C61.504 (3)
O3—H30.8200C5—H5A0.9700
O4—C61.416 (2)C5—H5B0.9700
O4—H40.8200C6—H6A0.9700
O5—C81.411 (3)C6—H6B0.9700
O5—H50.8200C7—C81.507 (3)
O6—C91.238 (3)C7—H7A0.9700
O7—C91.256 (3)C7—H7B0.9700
O8—N21.220 (3)C8—H8A0.9700
O9—N21.225 (3)C8—H8B0.9700
O10—H10A0.835 (15)C9—C101.512 (3)
O10—H10B0.820 (15)C10—C111.379 (3)
N1—C71.512 (2)C10—C151.382 (3)
N1—C51.522 (2)C11—C121.379 (3)
N1—C41.539 (2)C11—H110.9300
N1—H1N0.861 (16)C12—C131.370 (3)
N2—C131.467 (3)C12—H120.9300
C1—C41.526 (3)C13—C141.372 (3)
C1—H1A0.9700C14—C151.382 (3)
C1—H1B0.9700C14—H140.9300
C2—C41.535 (3)C15—H150.9300
C2—H2A0.9700
C1—O1—H1109.5C6—C5—H5B109.0
C2—O2—H2109.5N1—C5—H5B109.0
C3—O3—H3109.5H5A—C5—H5B107.8
C6—O4—H4109.5O4—C6—C5109.44 (16)
C8—O5—H5109.5O4—C6—H6A109.8
H10A—O10—H10B113.7 (18)C5—C6—H6A109.8
C7—N1—C5109.85 (14)O4—C6—H6B109.8
C7—N1—C4112.90 (14)C5—C6—H6B109.8
C5—N1—C4115.69 (13)H6A—C6—H6B108.2
C7—N1—H1N106.5 (16)C8—C7—N1110.38 (18)
C5—N1—H1N106.6 (16)C8—C7—H7A109.6
C4—N1—H1N104.5 (16)N1—C7—H7A109.6
O8—N2—O9123.56 (19)C8—C7—H7B109.6
O8—N2—C13118.41 (19)N1—C7—H7B109.6
O9—N2—C13118.03 (19)H7A—C7—H7B108.1
O1—C1—C4113.91 (16)O5—C8—C7108.33 (18)
O1—C1—H1A108.8O5—C8—H8A110.0
C4—C1—H1A108.8C7—C8—H8A110.0
O1—C1—H1B108.8O5—C8—H8B110.0
C4—C1—H1B108.8C7—C8—H8B110.0
H1A—C1—H1B107.7H8A—C8—H8B108.4
O2—C2—C4108.77 (15)O6—C9—O7125.51 (19)
O2—C2—H2A109.9O6—C9—C10117.01 (18)
C4—C2—H2A109.9O7—C9—C10117.48 (17)
O2—C2—H2B109.9C11—C10—C15119.07 (18)
C4—C2—H2B109.9C11—C10—C9119.80 (18)
H2A—C2—H2B108.3C15—C10—C9121.13 (18)
O3—C3—C4110.54 (15)C12—C11—C10120.7 (2)
O3—C3—H3A109.5C12—C11—H11119.6
C4—C3—H3A109.5C10—C11—H11119.6
O3—C3—H3B109.5C13—C12—C11118.7 (2)
C4—C3—H3B109.5C13—C12—H12120.7
H3A—C3—H3B108.1C11—C12—H12120.7
C1—C4—C3108.22 (15)C12—C13—C14122.34 (18)
C1—C4—C2112.06 (15)C12—C13—N2118.81 (19)
C3—C4—C2109.29 (15)C14—C13—N2118.85 (19)
C1—C4—N1112.42 (14)C13—C14—C15118.07 (19)
C3—C4—N1106.96 (13)C13—C14—H14121.0
C2—C4—N1107.73 (14)C15—C14—H14121.0
C6—C5—N1113.00 (15)C14—C15—C10121.11 (19)
C6—C5—H5A109.0C14—C15—H15119.4
N1—C5—H5A109.0C10—C15—H15119.4
O1—C1—C4—C3175.24 (15)N1—C7—C8—O565.8 (2)
O1—C1—C4—C254.7 (2)O6—C9—C10—C1116.3 (3)
O1—C1—C4—N166.8 (2)O7—C9—C10—C11163.1 (2)
O3—C3—C4—C1165.10 (16)O6—C9—C10—C15162.4 (2)
O3—C3—C4—C272.61 (19)O7—C9—C10—C1518.2 (3)
O3—C3—C4—N143.8 (2)C15—C10—C11—C120.1 (3)
O2—C2—C4—C158.93 (19)C9—C10—C11—C12178.6 (2)
O2—C2—C4—C361.03 (18)C10—C11—C12—C130.6 (4)
O2—C2—C4—N1176.91 (13)C11—C12—C13—C140.7 (3)
C7—N1—C4—C154.0 (2)C11—C12—C13—N2179.8 (2)
C5—N1—C4—C173.71 (19)O8—N2—C13—C1214.4 (3)
C7—N1—C4—C364.61 (19)O9—N2—C13—C12166.3 (2)
C5—N1—C4—C3167.63 (15)O8—N2—C13—C14166.1 (2)
C7—N1—C4—C2177.98 (15)O9—N2—C13—C1413.2 (3)
C5—N1—C4—C250.23 (19)C12—C13—C14—C150.2 (3)
C7—N1—C5—C6128.25 (17)N2—C13—C14—C15179.68 (18)
C4—N1—C5—C6102.50 (18)C13—C14—C15—C100.5 (3)
N1—C5—C6—O460.5 (2)C11—C10—C15—C140.7 (3)
C5—N1—C7—C877.4 (2)C9—C10—C15—C14178.05 (19)
C4—N1—C7—C8151.89 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O60.821.812.608 (3)166
O2—H2···O70.821.782.595 (3)176
O3—H3···O2i0.821.872.684 (2)175
O4—H4···O1ii0.821.942.742 (2)164
O5—H5···O100.821.982.774 (6)162
O10—H10A···O7iii0.84 (2)1.98 (2)2.811 (6)175
N1—H1N···O30.86 (2)2.23 (2)2.690 (2)113
N1—H1N···O40.86 (2)2.51 (2)2.917 (2)110
N1—H1N···O50.86 (2)2.47 (2)2.895 (4)112
C3—H3B···O20.972.462.873 (3)105
C5—H5A···O10.972.383.077 (3)129
C5—H5A···O9iv0.972.583.428 (6)146
C7—H7B···O5v0.972.553.276 (3)131
C11—H11···O60.932.492.781 (4)98
C12—H12···O80.932.452.726 (3)97
C14—H14···O90.932.452.720 (2)97
C15—H15···O70.932.552.831 (6)98
Symmetry codes: (i) x+2, y+1, z; (ii) x+1, y, z; (iii) x+1, y1, z; (iv) x, y+1, z+1; (v) x+2, y, z.
 

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