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The title compound, C8H12FN·H2O, was crystallized from an aqueous solution. The crystal structure features N—H...F, N—H...O and O—H...F hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049117/lh2251sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049117/lh2251Isup2.hkl
Contains datablock I

CCDC reference: 630170

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.045
  • wR factor = 0.113
  • Data-to-parameter ratio = 10.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.00 From the CIF: _reflns_number_total 1085 Count of symmetry unique reflns 1103 Completeness (_total/calc) 98.37% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: maXus (Mackay et al., 1999).

(I) top
Crystal data top
C8H12N+·F·H2OF(000) = 344
Mr = 159.20Dx = 1.135 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 66 reflections
a = 6.1754 (2) Åθ = 4.6–17.0°
b = 6.6276 (5) ŵ = 0.09 mm1
c = 22.772 (2) ÅT = 299 K
V = 932.01 (11) Å3Fragment, colourless
Z = 40.60 × 0.23 × 0.15 mm
Data collection top
Bruker–Nonius KappaCCD
diffractometer
Rint = 0.081
Radiation source: fine-focus sealed tubeθmax = 26.0°, θmin = 4.5°
φ & ω scansh = 75
5560 measured reflectionsk = 86
1085 independent reflectionsl = 2728
866 reflections with I > 2σ(I)
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)] = 0.046H-atom parameters constrained
wR(F2) = 0.113 w = 1/[σ2(Fo2) + (0.0398P)2 + 0.166P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max < 0.001
1085 reflectionsΔρmax = 0.18 e Å3
100 parametersΔρmin = 0.13 e Å3
0 restraints
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 will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4373 (5)0.1132 (5)0.11994 (11)0.0536 (7)
C20.2795 (4)0.2676 (4)0.14327 (11)0.0485 (6)
C30.0887 (5)0.3134 (5)0.11434 (12)0.0589 (8)
C40.0614 (5)0.4450 (5)0.13815 (14)0.0694 (9)
C50.0226 (7)0.5308 (6)0.19190 (15)0.0768 (10)
C60.1657 (7)0.4889 (6)0.22120 (14)0.0831 (11)
C70.3180 (6)0.3578 (5)0.19700 (12)0.0677 (9)
C80.3602 (7)0.1024 (5)0.13225 (16)0.0805 (11)
F10.6469 (2)0.4791 (2)0.01353 (7)0.0537 (4)
N10.4754 (3)0.1335 (3)0.05554 (9)0.0474 (5)
O10.7959 (3)0.8598 (3)0.03563 (11)0.0802 (7)
H1A0.52010.25820.04760.071*
H1B0.35280.10890.03630.071*
H1C0.57620.04560.04430.071*
H1O0.76060.73700.02740.120*
H2O0.91540.89020.01810.120*
H10.57600.13280.14010.064*
H30.06070.25430.07810.071*
H70.44600.33100.21710.081*
H60.19220.54830.25750.100*
H50.12410.61750.20850.092*
H40.18790.47520.11780.083*
H8A0.46710.19660.11860.121*
H8B0.22600.12610.11210.121*
H8C0.33910.11970.17370.121*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0533 (16)0.0524 (17)0.0551 (15)0.0025 (14)0.0024 (13)0.0155 (13)
C20.0544 (15)0.0450 (15)0.0462 (13)0.0124 (13)0.0027 (12)0.0064 (12)
C30.0589 (16)0.0624 (19)0.0553 (14)0.0014 (15)0.0003 (13)0.0107 (14)
C40.0671 (19)0.0629 (19)0.0782 (19)0.0036 (18)0.0088 (17)0.0077 (17)
C50.096 (2)0.055 (2)0.080 (2)0.008 (2)0.030 (2)0.0100 (18)
C60.126 (3)0.070 (2)0.0536 (18)0.027 (3)0.012 (2)0.0137 (17)
C70.084 (2)0.068 (2)0.0512 (16)0.019 (2)0.0044 (16)0.0045 (16)
C80.096 (3)0.0528 (19)0.093 (2)0.0038 (19)0.018 (2)0.0297 (18)
F10.0487 (8)0.0376 (8)0.0747 (10)0.0012 (7)0.0011 (7)0.0024 (7)
N10.0442 (11)0.0340 (11)0.0640 (12)0.0017 (11)0.0033 (10)0.0043 (10)
O10.0557 (11)0.0407 (11)0.144 (2)0.0031 (11)0.0237 (13)0.0136 (12)
Geometric parameters (Å, º) top
N1—C11.491 (3)O1—H1O0.8632
C1—C21.510 (4)O1—H2O0.8627
C1—C81.532 (5)C1—H10.9800
C3—C21.383 (4)C3—H30.9300
C3—C41.384 (4)C7—H70.9300
C2—C71.383 (4)C6—H60.9300
C7—C61.394 (5)C5—H50.9300
C6—C51.369 (5)C4—H40.9300
C5—C41.371 (5)C8—H8A0.9600
N1—H1A0.8900C8—H8B0.9600
N1—H1B0.8900C8—H8C0.9600
N1—H1C0.8900
N1—C1—C2112.7 (2)C2—C1—H1108.1
N1—C1—C8108.3 (2)C8—C1—H1108.1
C2—C1—C8111.5 (2)C2—C3—H3119.3
C2—C3—C4121.5 (3)C4—C3—H3119.3
C7—C2—C3118.2 (3)C2—C7—H7119.9
C7—C2—C1119.6 (3)C6—C7—H7119.9
C3—C2—C1122.1 (2)C5—C6—H6119.8
C2—C7—C6120.2 (3)C7—C6—H6119.8
C5—C6—C7120.5 (3)C6—C5—H5120.0
C6—C5—C4120.0 (3)C4—C5—H5120.0
C5—C4—C3119.6 (3)C5—C4—H4120.2
C1—N1—H1A109.5C3—C4—H4120.2
C1—N1—H1B109.5C1—C8—H8A109.5
H1A—N1—H1B109.5C1—C8—H8B109.5
C1—N1—H1C109.5H8A—C8—H8B109.5
H1A—N1—H1C109.5C1—C8—H8C109.5
H1B—N1—H1C109.5H8A—C8—H8C109.5
H1O—O1—H2O109.6H8B—C8—H8C109.5
N1—C1—H1108.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···F10.891.832.699 (2)164
N1—H1B···F1i0.891.802.673 (3)166
N1—H1C···O1ii0.891.842.722 (3)169
O1—H1O···F10.861.872.732 (3)172
O1—H2O···F1iii0.861.822.663 (2)165
Symmetry codes: (i) x1/2, y+1/2, z; (ii) x, y1, z; (iii) x+1/2, y+3/2, z.
 

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