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In the title compound, 1-{[2-(2-hydroxyethylamino)ethylimino]methyl}naphthalen-2-ol perchlorate, C15H19N2O2·ClO4, the ions are linked through weak inter­molecular N—H...O, O—H...O and C—H...O hydrogen bonds, forming columns along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805010585/ci6560sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805010585/ci6560Isup2.hkl
Contains datablock I

CCDC reference: 271839

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in solvent or counterion
  • R factor = 0.053
  • wR factor = 0.145
  • Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.80 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 44.00 Perc. 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 27.50 From the CIF: _reflns_number_total 3692 Count of symmetry unique reflns 2027 Completeness (_total/calc) 182.14% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1665 Fraction of Friedel pairs measured 0.821 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

1-{[2-(2-Hydroxyethylamino)ethylimino]methyl}naphthalen-2-ol perchlorate top
Crystal data top
C15H19N2O2·ClO4F(000) = 376
Mr = 358.77Dx = 1.460 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2667 reflections
a = 9.254 (2) Åθ = 2.3–23.7°
b = 6.864 (2) ŵ = 0.27 mm1
c = 13.174 (3) ÅT = 298 K
β = 102.78 (3)°Block, yellow
V = 816.1 (4) Å30.33 × 0.28 × 0.23 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
3692 independent reflections
Radiation source: fine-focus sealed tube2842 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.917, Tmax = 0.941k = 88
8798 measured reflectionsl = 1716
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.145 w = 1/[σ2(Fo2) + (0.0864P)2 + 0.0182P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
3692 reflectionsΔρmax = 0.50 e Å3
259 parametersΔρmin = 0.18 e Å3
108 restraintsAbsolute structure: Flack (1983), with 1677 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (9)
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*/UeqOcc. (<1)
Cl10.21505 (9)0.26779 (12)0.59387 (6)0.0601 (2)
O10.0125 (3)1.3228 (3)0.83807 (18)0.0599 (6)
O20.2002 (4)0.1483 (4)0.6250 (2)0.0898 (10)
H20.13860.13590.58940.135*
O30.2978 (5)0.3183 (9)0.5206 (4)0.1040 (18)0.805 (11)
O40.0978 (5)0.1427 (9)0.5408 (4)0.0962 (18)0.805 (11)
O50.1569 (7)0.4269 (10)0.6343 (7)0.132 (3)0.805 (11)
O60.3072 (7)0.1541 (11)0.6707 (5)0.138 (2)0.805 (11)
O3'0.3350 (16)0.375 (2)0.5737 (18)0.106 (8)0.195 (11)
O4'0.0971 (16)0.273 (4)0.5079 (10)0.113 (7)0.195 (11)
O5'0.1700 (19)0.356 (3)0.6777 (10)0.076 (6)0.195 (11)
O6'0.258 (2)0.0774 (16)0.619 (2)0.121 (9)0.195 (11)
N10.0614 (3)0.9738 (4)0.7998 (2)0.0525 (6)
N20.1399 (3)0.5379 (3)0.6673 (2)0.0478 (6)
H2A0.11800.56090.60510.057*
H2B0.07620.44710.70000.057*
C10.1968 (4)1.1654 (4)0.9410 (2)0.0469 (7)
C20.0991 (4)1.3255 (4)0.9145 (2)0.0478 (7)
C30.1281 (4)1.4965 (4)0.9805 (3)0.0549 (8)
H30.06701.60490.96420.066*
C40.2402 (4)1.5022 (5)1.0640 (3)0.0599 (9)
H40.25351.61371.10520.072*
C50.3393 (4)1.3443 (5)1.0919 (3)0.0541 (8)
C60.4575 (4)1.3528 (6)1.1822 (3)0.0673 (10)
H60.47081.46571.22230.081*
C70.5500 (4)1.2020 (7)1.2107 (3)0.0761 (12)
H70.62511.20961.27060.091*
C80.5324 (4)1.0340 (7)1.1499 (3)0.0683 (10)
H80.59740.93031.16900.082*
C90.4216 (4)1.0193 (6)1.0631 (3)0.0607 (9)
H90.41250.90571.02370.073*
C100.3196 (4)1.1737 (5)1.0313 (2)0.0494 (7)
C110.1707 (3)0.9951 (4)0.8801 (2)0.0480 (7)
H110.23580.89120.89840.058*
C120.0371 (4)0.7970 (4)0.7358 (3)0.0540 (7)
H12A0.10910.69870.76600.065*
H12B0.05040.82620.66640.065*
C130.1172 (4)0.7201 (4)0.7294 (3)0.0527 (7)
H13A0.13150.69460.79890.063*
H13B0.18930.81690.69720.063*
C140.2918 (4)0.4595 (6)0.6499 (3)0.0666 (9)
H14A0.36230.55910.61890.080*
H14B0.31350.42200.71600.080*
C150.3067 (4)0.2850 (6)0.5789 (3)0.0750 (11)
H15A0.40530.22970.56950.090*
H15B0.29090.32300.51130.090*
H10.006 (3)1.081 (3)0.784 (3)0.059 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0660 (5)0.0569 (5)0.0575 (4)0.0062 (4)0.0139 (3)0.0013 (4)
O10.0740 (14)0.0371 (11)0.0649 (13)0.0050 (10)0.0076 (11)0.0011 (10)
O20.133 (3)0.0443 (14)0.0858 (19)0.0070 (17)0.0112 (18)0.0085 (15)
O30.114 (3)0.108 (4)0.094 (3)0.024 (3)0.033 (3)0.005 (3)
O40.099 (3)0.111 (4)0.084 (3)0.035 (3)0.032 (2)0.028 (3)
O50.103 (3)0.108 (4)0.186 (6)0.019 (3)0.035 (4)0.061 (4)
O60.160 (5)0.115 (4)0.114 (4)0.013 (4)0.021 (3)0.040 (4)
O3'0.096 (10)0.136 (12)0.100 (11)0.018 (8)0.052 (8)0.001 (8)
O4'0.112 (10)0.125 (12)0.093 (9)0.005 (9)0.005 (7)0.003 (9)
O5'0.076 (8)0.091 (10)0.067 (7)0.017 (7)0.025 (6)0.020 (7)
O6'0.147 (12)0.083 (10)0.136 (12)0.027 (9)0.039 (9)0.011 (9)
N10.0672 (17)0.0311 (12)0.0601 (15)0.0003 (13)0.0159 (14)0.0040 (12)
N20.0544 (14)0.0304 (12)0.0598 (14)0.0057 (10)0.0155 (12)0.0016 (11)
C10.0555 (17)0.0332 (14)0.0559 (17)0.0043 (12)0.0209 (14)0.0009 (13)
C20.0621 (18)0.0331 (15)0.0517 (16)0.0043 (13)0.0200 (14)0.0001 (12)
C30.071 (2)0.0332 (16)0.0667 (19)0.0032 (14)0.0285 (17)0.0001 (15)
C40.083 (2)0.0402 (18)0.0638 (19)0.0105 (16)0.0328 (18)0.0121 (15)
C50.0588 (18)0.0523 (18)0.0574 (17)0.0130 (15)0.0260 (15)0.0049 (16)
C60.072 (2)0.075 (2)0.0583 (19)0.015 (2)0.0226 (18)0.0105 (19)
C70.062 (2)0.103 (3)0.064 (2)0.009 (2)0.0126 (17)0.001 (2)
C80.0549 (19)0.082 (3)0.069 (2)0.0027 (19)0.0170 (17)0.010 (2)
C90.0618 (19)0.059 (2)0.064 (2)0.0025 (16)0.0215 (17)0.0056 (17)
C100.0589 (18)0.0453 (16)0.0510 (16)0.0023 (13)0.0271 (14)0.0023 (14)
C110.0565 (16)0.0331 (14)0.0581 (17)0.0014 (13)0.0206 (14)0.0018 (13)
C120.0689 (18)0.0353 (17)0.0606 (17)0.0033 (14)0.0203 (14)0.0074 (14)
C130.0677 (18)0.0320 (15)0.0608 (17)0.0029 (13)0.0195 (14)0.0032 (12)
C140.0563 (18)0.0511 (19)0.094 (3)0.0004 (16)0.0203 (18)0.003 (2)
C150.070 (2)0.052 (2)0.094 (3)0.013 (2)0.0005 (19)0.004 (2)
Geometric parameters (Å, º) top
Cl1—O51.376 (4)C4—C51.415 (5)
Cl1—O6'1.385 (8)C4—H40.93
Cl1—O4'1.389 (8)C5—C101.407 (4)
Cl1—O5'1.400 (8)C5—C61.428 (5)
Cl1—O31.402 (4)C6—C71.343 (6)
Cl1—O3'1.406 (8)C6—H60.93
Cl1—O61.407 (4)C7—C81.393 (6)
Cl1—O41.438 (4)C7—H70.93
O1—C21.274 (4)C8—C91.361 (5)
O2—C151.399 (5)C8—H80.93
O2—H20.82C9—C101.419 (5)
N1—C111.300 (4)C9—H90.93
N1—C121.466 (4)C11—H110.93
N1—H10.897 (11)C12—C131.506 (5)
N2—C141.476 (4)C12—H12A0.97
N2—C131.484 (4)C12—H12B0.97
N2—H2A0.90C13—H13A0.97
N2—H2B0.90C13—H13B0.97
C1—C111.409 (4)C14—C151.507 (6)
C1—C21.416 (4)C14—H14A0.97
C1—C101.453 (5)C14—H14B0.97
C2—C31.449 (4)C15—H15A0.97
C3—C41.336 (5)C15—H15B0.97
C3—H30.93
O6'—Cl1—O4'110.7 (9)C6—C7—C8119.4 (4)
O6'—Cl1—O5'109.7 (9)C6—C7—H7120.3
O4'—Cl1—O5'108.3 (8)C8—C7—H7120.3
O6'—Cl1—O3'110.1 (9)C9—C8—C7121.0 (4)
O4'—Cl1—O3'110.0 (9)C9—C8—H8119.5
O5'—Cl1—O3'108.0 (8)C7—C8—H8119.5
O5—Cl1—O3113.0 (4)C8—C9—C10121.4 (4)
O5—Cl1—O6112.9 (4)C8—C9—H9119.3
O3—Cl1—O6107.2 (4)C10—C9—H9119.3
O5—Cl1—O4110.1 (3)C5—C10—C9117.4 (3)
O3—Cl1—O4106.3 (3)C5—C10—C1118.5 (3)
O6—Cl1—O4106.9 (4)C9—C10—C1124.1 (3)
C15—O2—H2109.5N1—C11—C1124.1 (3)
C11—N1—C12123.6 (3)N1—C11—H11117.9
C11—N1—H1114 (2)C1—C11—H11117.9
C12—N1—H1122 (2)N1—C12—C13110.2 (3)
C14—N2—C13114.0 (3)N1—C12—H12A109.6
C14—N2—H2A108.8C13—C12—H12A109.6
C13—N2—H2A108.8N1—C12—H12B109.6
C14—N2—H2B108.8C13—C12—H12B109.6
C13—N2—H2B108.8H12A—C12—H12B108.1
H2A—N2—H2B107.7N2—C13—C12110.1 (2)
C11—C1—C2119.0 (3)N2—C13—H13A109.6
C11—C1—C10120.2 (3)C12—C13—H13A109.6
C2—C1—C10120.8 (3)N2—C13—H13B109.6
O1—C2—C1123.0 (3)C12—C13—H13B109.6
O1—C2—C3119.7 (3)H13A—C13—H13B108.2
C1—C2—C3117.2 (3)N2—C14—C15109.8 (3)
C4—C3—C2121.6 (3)N2—C14—H14A109.7
C4—C3—H3119.2C15—C14—H14A109.7
C2—C3—H3119.2N2—C14—H14B109.7
C3—C4—C5122.1 (3)C15—C14—H14B109.7
C3—C4—H4118.9H14A—C14—H14B108.2
C5—C4—H4118.9O2—C15—C14107.7 (3)
C10—C5—C4119.7 (3)O2—C15—H15A110.2
C10—C5—C6119.1 (3)C14—C15—H15A110.2
C4—C5—C6121.2 (3)O2—C15—H15B110.2
C7—C6—C5121.7 (4)C14—C15—H15B110.2
C7—C6—H6119.2H15A—C15—H15B108.5
C5—C6—H6119.2
C11—C1—C2—O10.4 (4)C4—C5—C10—C10.0 (4)
C10—C1—C2—O1177.8 (3)C6—C5—C10—C1178.6 (3)
C11—C1—C2—C3178.8 (3)C8—C9—C10—C51.3 (5)
C10—C1—C2—C30.5 (4)C8—C9—C10—C1178.4 (3)
O1—C2—C3—C4177.1 (3)C11—C1—C10—C5178.1 (3)
C1—C2—C3—C41.3 (4)C2—C1—C10—C50.1 (4)
C2—C3—C4—C51.5 (5)C11—C1—C10—C91.5 (4)
C3—C4—C5—C100.8 (5)C2—C1—C10—C9179.7 (3)
C3—C4—C5—C6179.4 (3)C12—N1—C11—C1178.8 (3)
C10—C5—C6—C70.2 (5)C2—C1—C11—N10.0 (5)
C4—C5—C6—C7178.4 (3)C10—C1—C11—N1178.2 (3)
C5—C6—C7—C81.3 (6)C11—N1—C12—C13125.2 (3)
C6—C7—C8—C91.1 (6)C14—N2—C13—C12175.6 (3)
C7—C8—C9—C100.2 (5)N1—C12—C13—N2178.3 (2)
C4—C5—C10—C9179.7 (3)C13—N2—C14—C15175.3 (3)
C6—C5—C10—C91.1 (4)N2—C14—C15—O257.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.89 (1)2.54 (3)3.183 (4)129 (3)
N1—H1···O10.89 (1)1.83 (3)2.572 (3)139 (3)
O2—H2···O40.822.413.193 (6)160
N2—H2B···O50.902.502.973 (6)113
N2—H2B···O50.902.443.104 (16)131
N2—H2B···O1ii0.901.982.731 (3)140
N2—H2A···O4iii0.902.122.914 (18)146
N2—H2A···O4iii0.902.052.941 (5)171
C6—H6···O6iv0.932.573.302 (4)136
C13—H13B···O2i0.972.463.263 (4)140
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z; (iii) x, y+1/2, z+1; (iv) x+1, y+3/2, z+2.
 

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