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Crystallization of tacrine hydrochloride, an acetylcholinesterase inhibitor used during treatment of mild to moderate Alzheimer's disease, from a water:ethanol solution has resulted in an orthorhombic pseudopolymorph. This orthorhombic form which occurs as a dihydrate shows columns of stacking acridines together with continuous Cl—Owater—Owater—Cl chains and ladder-like ribbons composed of squares and hexagons.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520616011094/um5004sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520616011094/um5004Isup2.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520616011094/um5004sup3.pdf
Experimental part, additional tables and figures

CCDC reference: 1459028

Computing details top

Data collection: CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44); cell refinement: CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44); data reduction: CrysAlis PRO, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44); program(s) used to refine structure: SHELXL (Sheldrick, 2008); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

(I) top
Crystal data top
C13H15N2·Cl·2(H2O)Dx = 1.345 Mg m3
Mr = 270.75Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcnCell parameters from 1701 reflections
a = 17.8252 (7) Åθ = 3.2–29.0°
b = 7.2708 (2) ŵ = 0.28 mm1
c = 20.6396 (7) ÅT = 100 K
V = 2674.98 (16) Å3Needle, colourless
Z = 80.61 × 0.14 × 0.1 mm
F(000) = 1152
Data collection top
SuperNova, Single source at offset, Eos
diffractometer
2367 independent reflections
Mirror monochromator2026 reflections with I > 2σ(I)
Detector resolution: 15.9631 pixels mm-1Rint = 0.017
ω scansθmax = 25.4°, θmin = 3.0°
Absorption correction: multi-scan
CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
h = 1120
Tmin = 0.841, Tmax = 1.000k = 84
4930 measured reflectionsl = 2419
Refinement top
Refinement on F2234 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.107 w = 1/[σ2(Fo2) + (0.0473P)2 + 2.1477P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
2367 reflectionsΔρmax = 0.29 e Å3
221 parametersΔρmin = 0.29 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.32651 (11)0.5998 (2)0.36954 (8)0.0192 (4)
H10.3731 (15)0.618 (3)0.3849 (11)0.023*
C20.32197 (12)0.5601 (2)0.30558 (9)0.0182 (5)
C30.25260 (13)0.5385 (3)0.27591 (9)0.0194 (4)
C40.18668 (12)0.5524 (3)0.31418 (10)0.0192 (5)
C50.19371 (12)0.5975 (3)0.38174 (10)0.0175 (5)
C60.26480 (12)0.6202 (3)0.40778 (9)0.0176 (4)
C70.39321 (14)0.5412 (3)0.27018 (10)0.0266 (5)
H7A0.44120.55050.28990.032*0.413 (9)
H7BA0.42840.47000.29750.032*0.587 (9)
H7BB0.41490.66540.26440.032*0.587 (9)
C8A0.3822 (6)0.5087 (12)0.2058 (3)0.034 (2)0.413 (9)
H8A0.42580.51130.17940.041*0.413 (9)
C9A0.3139 (4)0.4718 (13)0.1735 (5)0.042 (2)0.413 (9)
H9A0.31380.42920.13000.050*0.413 (9)
C8B0.3889 (4)0.4483 (9)0.2035 (2)0.0269 (14)0.587 (9)
H8BA0.43550.47100.17880.032*0.587 (9)
H8BB0.38230.31390.20850.032*0.587 (9)
C9B0.3233 (3)0.5294 (9)0.1692 (3)0.0285 (14)0.587 (9)
H9BA0.31960.47440.12540.034*0.587 (9)
H9BB0.33150.66330.16390.034*0.587 (9)
C100.24876 (13)0.4981 (3)0.20558 (10)0.0260 (5)
H100.20190.49090.18380.031*0.413 (9)
H10A0.20960.57670.18580.031*0.587 (9)
H10B0.23330.36840.19970.031*0.587 (9)
N110.11904 (12)0.5245 (3)0.28843 (10)0.0265 (5)
H11A0.1116 (15)0.504 (3)0.2476 (13)0.032*
H11B0.0764 (15)0.527 (4)0.3115 (13)0.032*
C120.12871 (13)0.6192 (3)0.42298 (10)0.0246 (5)
H12A0.10770.49550.43160.029*0.413 (9)
H12B0.09030.68900.39850.029*0.413 (9)
H120.07940.60830.40600.029*0.587 (9)
C13A0.1405 (7)0.7152 (13)0.4881 (4)0.023 (2)0.413 (9)
H13A0.14610.84920.48110.028*0.413 (9)
H13B0.09620.69500.51610.028*0.413 (9)
C14A0.2087 (5)0.642 (2)0.5206 (6)0.025 (3)0.413 (9)
H14A0.20150.51010.53120.030*0.413 (9)
H14B0.21800.70940.56140.030*0.413 (9)
C13B0.1403 (5)0.6553 (10)0.4863 (3)0.0226 (16)0.587 (9)
H13C0.09840.66050.51470.027*0.587 (9)
C14B0.2133 (3)0.6857 (15)0.5115 (4)0.0240 (18)0.587 (9)
H14C0.21850.72270.55540.029*0.587 (9)
C150.27584 (13)0.6638 (3)0.47513 (10)0.0246 (5)
H15A0.29310.79300.47790.030*0.413 (9)
H15B0.31700.58550.49170.030*0.413 (9)
H150.32460.67660.49320.030*0.587 (9)
Cl160.04925 (3)0.47210 (8)0.14505 (2)0.02686 (18)
O170.05413 (11)0.8247 (3)0.05294 (9)0.0360 (4)
H17A0.0540 (16)0.727 (3)0.0736 (12)0.043*
H17B0.0261 (15)0.903 (3)0.0667 (13)0.043*
O180.47049 (9)0.6413 (2)0.42146 (7)0.0250 (4)
H18A0.4955 (14)0.723 (3)0.4030 (11)0.030*
H18B0.4611 (14)0.672 (3)0.4588 (9)0.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0165 (10)0.0224 (9)0.0186 (9)0.0014 (8)0.0010 (7)0.0019 (7)
C20.0235 (12)0.0149 (10)0.0163 (9)0.0012 (9)0.0015 (8)0.0007 (8)
C30.0226 (11)0.0175 (10)0.0179 (9)0.0027 (9)0.0014 (8)0.0006 (8)
C40.0226 (12)0.0141 (10)0.0210 (10)0.0028 (9)0.0044 (8)0.0015 (8)
C50.0187 (11)0.0161 (10)0.0176 (9)0.0004 (9)0.0009 (8)0.0002 (8)
C60.0193 (11)0.0147 (10)0.0189 (9)0.0004 (9)0.0017 (8)0.0001 (8)
C70.0306 (13)0.0290 (12)0.0203 (10)0.0010 (10)0.0019 (9)0.0020 (9)
C8A0.024 (4)0.049 (5)0.028 (3)0.006 (3)0.010 (3)0.016 (3)
C9A0.034 (3)0.061 (6)0.031 (4)0.003 (3)0.006 (3)0.019 (4)
C8B0.029 (3)0.034 (3)0.018 (2)0.001 (2)0.0036 (18)0.0063 (18)
C9B0.035 (3)0.028 (3)0.023 (2)0.011 (2)0.004 (2)0.010 (2)
C100.0240 (12)0.0307 (12)0.0234 (10)0.0032 (10)0.0037 (9)0.0032 (9)
N110.0213 (11)0.0353 (11)0.0228 (10)0.0010 (9)0.0065 (8)0.0036 (9)
C120.0225 (12)0.0282 (12)0.0229 (10)0.0011 (10)0.0035 (9)0.0001 (9)
C13A0.024 (4)0.023 (5)0.023 (3)0.005 (3)0.005 (2)0.009 (3)
C14A0.026 (4)0.023 (6)0.027 (4)0.000 (3)0.003 (3)0.001 (3)
C13B0.021 (2)0.025 (4)0.022 (2)0.001 (3)0.0032 (17)0.004 (2)
C14B0.027 (3)0.026 (5)0.019 (3)0.001 (2)0.0002 (18)0.009 (2)
C150.0224 (13)0.0289 (12)0.0227 (10)0.0008 (10)0.0010 (9)0.0034 (9)
Cl160.0224 (3)0.0364 (3)0.0218 (3)0.0012 (2)0.0052 (2)0.0039 (2)
O170.0288 (11)0.0426 (11)0.0367 (10)0.0010 (9)0.0008 (8)0.0119 (8)
O180.0231 (9)0.0353 (9)0.0167 (7)0.0065 (7)0.0001 (6)0.0001 (7)
Geometric parameters (Å, º) top
N1—H10.90 (3)C10—H100.9500
N1—C21.354 (3)C10—H10A0.9900
N1—C61.362 (3)C10—H10B0.9900
C2—C31.389 (3)N11—H11A0.87 (3)
C2—C71.471 (3)N11—H11B0.90 (3)
C3—C41.419 (3)C12—H12A0.9900
C3—C101.483 (3)C12—H12B0.9900
C4—C51.438 (3)C12—H120.9500
C4—N111.333 (3)C12—C13A1.529 (6)
C5—C61.386 (3)C12—C13B1.349 (5)
C5—C121.446 (3)C13A—H13A0.9900
C6—C151.439 (3)C13A—H13B0.9900
C7—H7A0.9500C13A—C14A1.488 (7)
C7—H7BA0.9900C14A—H14A0.9900
C7—H7BB0.9900C14A—H14B0.9900
C7—C8A1.363 (6)C14A—C151.528 (6)
C7—C8B1.534 (5)C13B—H13C0.9500
C8A—H8A0.9500C13B—C14B1.420 (7)
C8A—C9A1.415 (7)C14B—H14C0.9500
C9A—H9A0.9500C14B—C151.353 (5)
C9A—C101.350 (6)C15—H15A0.9900
C8B—H8BA0.9900C15—H15B0.9900
C8B—H8BB0.9900C15—H150.9500
C8B—C9B1.488 (6)O17—H17A0.830 (17)
C9B—H9BA0.9900O17—H17B0.810 (17)
C9B—H9BB0.9900O18—H18A0.834 (17)
C9B—C101.544 (5)O18—H18B0.818 (16)
C2—N1—H1115.4 (15)C3—C10—H10B108.7
C2—N1—C6122.70 (19)C9A—C10—C3118.0 (5)
C6—N1—H1121.8 (15)C9A—C10—H10121.0
N1—C2—C3120.48 (19)C9B—C10—H10A108.7
N1—C2—C7116.91 (19)C9B—C10—H10B108.7
C3—C2—C7122.61 (18)H10A—C10—H10B107.6
C2—C3—C4118.93 (18)C4—N11—H11A123.5 (18)
C2—C3—C10119.68 (19)C4—N11—H11B123.5 (17)
C4—C3—C10121.4 (2)H11A—N11—H11B113 (2)
C3—C4—C5118.93 (19)C5—C12—H12A108.0
N11—C4—C3121.07 (19)C5—C12—H12B108.0
N11—C4—C5120.0 (2)C5—C12—H12121.0
C4—C5—C12121.72 (19)C5—C12—C13A117.2 (5)
C6—C5—C4118.86 (19)H12A—C12—H12B107.2
C6—C5—C12119.41 (18)C13A—C12—H12A108.0
N1—C6—C5120.04 (18)C13A—C12—H12B108.0
N1—C6—C15118.25 (19)C13B—C12—C5118.0 (4)
C5—C6—C15121.71 (19)C13B—C12—H12121.0
C2—C7—H7A124.0C12—C13A—H13A109.6
C2—C7—H7BA108.2C12—C13A—H13B109.6
C2—C7—H7BB108.2H13A—C13A—H13B108.1
C2—C7—C8B116.3 (3)C14A—C13A—C12110.1 (9)
H7BA—C7—H7BB107.4C14A—C13A—H13A109.6
C8A—C7—C2112.1 (5)C14A—C13A—H13B109.6
C8A—C7—H7A124.0C13A—C14A—H14A109.9
C8B—C7—H7BA108.2C13A—C14A—H14B109.9
C8B—C7—H7BB108.2C13A—C14A—C15109.0 (8)
C7—C8A—H8A116.0H14A—C14A—H14B108.3
C7—C8A—C9A128.1 (9)C15—C14A—H14A109.9
C9A—C8A—H8A116.0C15—C14A—H14B109.9
C8A—C9A—H9A120.6C12—C13B—H13C119.1
C10—C9A—C8A118.8 (9)C12—C13B—C14B121.7 (7)
C10—C9A—H9A120.6C14B—C13B—H13C119.1
C7—C8B—H8BA110.3C13B—C14B—H14C118.9
C7—C8B—H8BB110.3C15—C14B—C13B122.2 (7)
H8BA—C8B—H8BB108.6C15—C14B—H14C118.9
C9B—C8B—C7107.0 (5)C6—C15—C14A117.5 (6)
C9B—C8B—H8BA110.3C6—C15—H15A107.9
C9B—C8B—H8BB110.3C6—C15—H15B107.9
C8B—C9B—H9BA109.1C6—C15—H15121.7
C8B—C9B—H9BB109.1C14A—C15—H15A107.9
C8B—C9B—C10112.7 (5)C14A—C15—H15B107.9
H9BA—C9B—H9BB107.8C14B—C15—C6116.7 (4)
C10—C9B—H9BA109.1C14B—C15—H15121.7
C10—C9B—H9BB109.1H15A—C15—H15B107.2
C3—C10—C9B114.0 (3)H17A—O17—H17B115 (3)
C3—C10—H10121.0H18A—O18—H18B110 (2)
C3—C10—H10A108.7
N1—C2—C3—C42.1 (3)C5—C6—C15—C14A13.7 (7)
N1—C2—C3—C10179.00 (19)C5—C6—C15—C14B1.4 (6)
N1—C2—C7—C8A177.5 (4)C5—C12—C13A—C14A45.4 (9)
N1—C2—C7—C8B164.6 (3)C5—C12—C13B—C14B4.8 (10)
N1—C6—C15—C14A165.8 (6)C6—N1—C2—C30.1 (3)
N1—C6—C15—C14B179.1 (5)C6—N1—C2—C7179.78 (18)
C2—N1—C6—C51.0 (3)C6—C5—C12—C13A15.9 (5)
C2—N1—C6—C15179.49 (19)C6—C5—C12—C13B2.1 (5)
C2—C3—C4—C53.0 (3)C7—C2—C3—C4177.72 (19)
C2—C3—C4—N11176.97 (18)C7—C2—C3—C101.2 (2)
C2—C3—C10—C9A4.3 (6)C7—C8A—C9A—C1011.6 (14)
C2—C3—C10—C9B13.8 (3)C7—C8B—C9B—C1060.1 (7)
C2—C7—C8A—C9A8.0 (11)C8A—C9A—C10—C38.7 (10)
C2—C7—C8B—C9B44.9 (6)C8B—C9B—C10—C346.4 (6)
C3—C2—C7—C8A2.7 (4)C10—C3—C4—C5178.08 (19)
C3—C2—C7—C8B15.3 (4)C10—C3—C4—N111.9 (3)
C3—C4—C5—C62.0 (3)N11—C4—C5—C6178.0 (2)
C3—C4—C5—C12178.16 (19)N11—C4—C5—C121.8 (3)
C4—C3—C10—C9A174.6 (5)C12—C5—C6—N1179.84 (19)
C4—C3—C10—C9B167.4 (3)C12—C5—C6—C150.4 (3)
C4—C5—C6—N10.0 (3)C12—C13A—C14A—C1556.1 (12)
C4—C5—C6—C15179.5 (2)C12—C13B—C14B—C156.2 (14)
C4—C5—C12—C13A164.3 (4)C13A—C14A—C15—C642.5 (12)
C4—C5—C12—C13B177.8 (4)C13B—C14B—C15—C64.2 (12)
 

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