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Venlafaxine hydro­chloride, [(\pm)-N,N-di­methyl-2-(1-hydroxy­cyclo­hex-1-yl)-2-(4-methoxy­phenyl) ethyl­amine hydro­chloride, C17H28ClNO2] is found to crystallize in both orthorhombic and monoclinic crystal systems. The molecular structures in the two polymorphs differ in the conformations of the substituents at the ethyl­amine group. In the monoclinic crystal structure, the mol­ecules translated along the a axis are linked by Cl ions through O—H...Cl and N—H...Cl hydrogen bonds to form infinite one-dimensional chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680201588X/ci6152sup1.cif
Contains datablocks venlafaxineHCl, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680201588X/ci6152IIsup2.hkl
Contains datablock II

CCDC reference: 198947

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.068
  • wR factor = 0.068
  • Data-to-parameter ratio = 9.1

checkCIF results

No syntax errors found

Structure: II
-------------

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFNR_01 Alert C Ratio of reflections to parameters is < 10 for a centrosymmetric structure sine(theta)/lambda 0.6098 Proportion of unique data used 0.5496 Ratio reflections to parameters 9.1256 PLAT_031 Alert C Refined Extinction parameter within range .... 3.14 Sigma General Notes
ABSTM_02 When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.825 Tmax scaled 0.821 Tmin scaled 0.695
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Comment top

Venlafaxine hydrochloride, [(±)-N,N-dimethyl-2-(1-hydroxycyclohex-1-yl)-2-(4-methoxyphenyl) ethylamine hydrochloride, C17H28ClNO2] is used as an antidepressant and an anxiolytic. Recrystallization of the compound for purification yielded crystals of two different morphologies, viz. blocks (form I) and needles (form II), as observed under the microscope. They were separated manually and characterized by different solid-state techniques such as differential scanning calorimetry, infrared spectroscopy, powder X-ray diffraction and single-crystal X-ray diffraction. These polymorphic forms were patented along with their characteristic physicochemical data (Mahender Rao et al., 1999; Mahender Rao et al., 2002). Recently, the crystal structure of form I has been reported in the orthorhombic space group Pca21 by Vega et al. (2000). In this paper we report the structure of form II and compare it with that of form I.

Form II of venlafaxine hydrochloride is found to crystallize in the monoclinic space group P21/n. The structure of the molecule in the monoclinic form is shown in Fig. 1. A l l the bond lengths show normal values (Allen et al., 1987) and match well with the corresponding values observed for the orthorhombic polymorph (Vega et al., 2000). In both polymorphs, the cyclohexane ring adopts a chair conformation. An intermolecular hydrogen bond links the nitrogen atom of the dimethylammonium group of the venlafaxine cation to the chloride anion. The chloride ion is also involved in another hydrogen bond, with the oxygen atom of the hydroxyl group of the cation translated one unit along the a axis. These hydrogen bonds (Table 2), which stabilize the crystal lattice (Fig. 2), lead to chains of molecules along the short a (= 5.797 Å) axis. An identical hydrogen-bonding scheme constitutes the molecular chain in the orthorhombic polymorph, along the short b (=5.881 Å) axis (Vega et al., 2000). Hence the two polymorphic modifications have the same lattice stabilization mechanism. However, careful comparison of the torsion angles (Table 3) reveals that the molecules differ by 3 to 6° in the rotations about the bonds N1—C14, C1—C7 and C7—C14. Hence these two forms of venlafaxine hydrochloride are conformational polymorphs (Bilton et al., 1999).

Experimental top

Crystals of form II of venlafaxine hydrochloride suitable for X-ray diffraction were grown from a mixture of methanol and ethyl acetate (1:1).

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1995); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: TEXSAN; molecular graphics: TEXSAN; software used to prepare material for publication: TEXSAN.

Figures top
[Figure 1] Fig. 1. A perspective view of Venlafaxine hydrochloride. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Packing of the molecules viewed down the b axis.
(±)–N,N–dimethyl–2–(1–hydroxycyclohex–1–yl)–2–(4–methoxyphenyl) ethylamine hydrochloride(±)–1–[2–(Dimethylamino)–1–(4–methoxyphenyl)ethyl] cyclohexanol hydrochloride1-(2-(1-Hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl)dimethylammonium chloride top
Crystal data top
C17H28NO2+·ClF(000) = 680.00
Mr = 313.87Dx = 1.197 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ynCell parameters from 24 reflections
a = 5.797 (6) Åθ = 6.4–23.7°
b = 26.074 (7) ŵ = 1.97 mm1
c = 11.722 (3) ÅT = 298 K
β = 100.72 (5)°Needle, colourless
V = 1741 (2) Å30.40 × 0.10 × 0.10 mm
Z = 4
Data collection top
Rigaku AFC7S
diffractometer
3304 reflections with I > 1.30s(I)
Radiation source: X-ray tubeRint = 0.078
Graphite monochromatorθmax = 70.1°, θmin = 3.4°
ω–2θ scansh = 06
Absorption correction: ψ scan
(North, Phillips & Mathews, 1968)
k = 031
Tmin = 0.843, Tmax = 0.996l = 1414
3564 measured reflections4 standard reflections every 150 reflections
3304 independent reflections intensity decay: 0.3%
Refinement top
Refinement on F78 constraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.068Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo) + 0.00016|Fo|2]
wR(F2) = 0.068(Δ/σ)max = 0.001
S = 1.29Δρmax = 0.40 e Å3
1816 reflectionsΔρmin = 0.33 e Å3
199 parametersExtinction correction: Zachariasen (1967), equ(3) Acta Cryst.(1968) A24, p213.
0 restraintsExtinction coefficient: 0.0000022 (7)
Crystal data top
C17H28NO2+·ClV = 1741 (2) Å3
Mr = 313.87Z = 4
Monoclinic, P21/nCu Kα radiation
a = 5.797 (6) ŵ = 1.97 mm1
b = 26.074 (7) ÅT = 298 K
c = 11.722 (3) Å0.40 × 0.10 × 0.10 mm
β = 100.72 (5)°
Data collection top
Rigaku AFC7S
diffractometer
3304 reflections with I > 1.30s(I)
Absorption correction: ψ scan
(North, Phillips & Mathews, 1968)
Rint = 0.078
Tmin = 0.843, Tmax = 0.9964 standard reflections every 150 reflections
3564 measured reflections intensity decay: 0.3%
3304 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0680 restraints
wR(F2) = 0.068H atoms treated by a mixture of independent and constrained refinement
S = 1.29Δρmax = 0.40 e Å3
1816 reflectionsΔρmin = 0.33 e Å3
199 parameters
Special details top

Experimental. The scan width was (0.94 + 0.14tanθ)° with an ω scan speed of 16° per minute (up to 5 scans to achieve I/σ(I) > 15). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.3864 (2)0.77716 (5)0.75684 (10)0.0628 (4)
O10.4899 (6)0.93560 (14)0.0837 (3)0.0686 (11)
O21.1462 (5)0.86870 (12)0.5932 (3)0.0526 (11)
N10.6144 (7)0.75613 (14)0.5480 (3)0.0505 (12)
C10.6672 (7)0.87054 (16)0.4127 (3)0.0451 (12)
C20.4611 (8)0.89845 (18)0.3773 (4)0.0543 (17)
C30.4079 (8)0.91970 (18)0.2679 (4)0.0577 (17)
C40.5583 (8)0.91298 (18)0.1894 (4)0.0520 (16)
C50.7582 (8)0.88458 (17)0.2224 (4)0.0543 (17)
C60.8127 (8)0.86362 (17)0.3321 (4)0.0524 (17)
C70.7290 (7)0.84980 (16)0.5355 (3)0.0430 (12)
C80.9178 (7)0.88243 (15)0.6157 (3)0.0438 (12)
C90.8885 (9)0.93963 (17)0.5908 (4)0.0587 (17)
C101.0629 (10)0.97210 (19)0.6748 (5)0.0746 (19)
C111.0499 (12)0.96105 (19)0.7997 (5)0.078 (2)
C121.0831 (9)0.90406 (18)0.8256 (4)0.0625 (18)
C130.9062 (8)0.87267 (16)0.7432 (3)0.0509 (14)
C140.8064 (7)0.79359 (15)0.5410 (4)0.0458 (12)
C150.7138 (10)0.70360 (19)0.5658 (5)0.077 (2)
C160.4212 (9)0.7576 (2)0.4450 (5)0.077 (2)
C170.6411 (10)0.9296 (2)0.0016 (4)0.074 (2)
H10.355030.902790.429300.0650*
H20.268020.939140.246050.0704*
H30.860770.879220.169100.0651*
H40.952570.844120.353010.0632*
H50.590090.851380.567480.0525*
H60.911050.946070.513870.0707*
H70.733810.949370.597780.0707*
H81.217030.965000.662310.0895*
H91.027841.007300.659410.0895*
H101.171410.979450.848360.0939*
H110.901940.971740.814920.0939*
H121.236880.894200.817290.0744*
H131.063230.897710.902960.0744*
H140.753130.880970.755430.0608*
H150.936690.837390.759690.0608*
H160.925850.789200.607740.0547*
H170.868190.786190.473280.0547*
H180.594810.680500.579070.0933*
H190.771820.693180.498810.0933*
H200.838370.703540.631170.0933*
H210.353860.790940.438110.0913*
H220.482170.749880.377210.0913*
H230.304250.733150.453890.0913*
H240.656620.894130.014220.0890*
H250.575830.946970.068110.0890*
H260.791130.943520.032390.0890*
H271.226 (9)0.848 (2)0.649 (4)0.070 (13)*
H280.565 (10)0.763 (2)0.617 (5)0.101 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0613 (7)0.0738 (8)0.0592 (6)0.0130 (6)0.0269 (5)0.0163 (7)
O10.071 (2)0.082 (2)0.0544 (19)0.0120 (18)0.0158 (16)0.0130 (19)
O20.0431 (17)0.063 (2)0.0573 (19)0.0043 (16)0.0239 (15)0.0022 (15)
N10.057 (2)0.042 (2)0.058 (2)0.0084 (17)0.0253 (19)0.0041 (17)
C10.044 (2)0.045 (2)0.049 (2)0.004 (2)0.0157 (19)0.0002 (19)
C20.052 (3)0.054 (3)0.061 (3)0.012 (2)0.021 (2)0.010 (2)
C30.049 (3)0.062 (3)0.063 (3)0.017 (2)0.013 (2)0.011 (2)
C40.057 (3)0.053 (3)0.047 (2)0.002 (2)0.012 (2)0.004 (2)
C50.060 (3)0.058 (3)0.049 (3)0.003 (2)0.021 (2)0.005 (2)
C60.050 (3)0.055 (3)0.056 (3)0.015 (2)0.020 (2)0.002 (2)
C70.040 (2)0.044 (2)0.049 (2)0.0025 (18)0.0186 (18)0.0053 (18)
C80.050 (2)0.039 (2)0.046 (2)0.0025 (17)0.0181 (19)0.0027 (18)
C90.076 (3)0.048 (3)0.055 (3)0.003 (2)0.020 (2)0.006 (2)
C100.112 (4)0.044 (3)0.070 (3)0.014 (3)0.023 (3)0.001 (3)
C110.116 (5)0.052 (3)0.067 (3)0.007 (3)0.017 (3)0.009 (3)
C120.084 (4)0.058 (3)0.047 (2)0.005 (2)0.016 (2)0.001 (3)
C130.064 (3)0.047 (2)0.047 (2)0.007 (2)0.024 (2)0.008 (2)
C140.049 (2)0.038 (2)0.052 (2)0.0002 (19)0.0139 (19)0.0014 (18)
C150.087 (4)0.046 (3)0.109 (4)0.002 (3)0.043 (3)0.001 (3)
C160.056 (3)0.088 (4)0.086 (4)0.016 (3)0.014 (3)0.026 (3)
C170.092 (4)0.085 (4)0.047 (3)0.000 (3)0.016 (3)0.006 (3)
Geometric parameters (Å, º) top
O1—C41.363 (6)C5—H30.95
O1—C171.426 (7)C6—H40.95
O2—C81.442 (5)C7—H50.95
O2—H270.91 (5)C9—H60.95
N1—C151.486 (6)C9—H70.95
N1—C161.487 (7)C10—H80.95
N1—C141.495 (6)C10—H90.95
N1—H280.92 (6)C11—H100.95
C1—C71.517 (5)C11—H110.95
C1—C61.390 (6)C12—H120.95
C1—C21.395 (6)C12—H130.95
C2—C31.378 (7)C13—H140.95
C3—C41.391 (7)C13—H150.95
C4—C51.369 (7)C14—H160.95
C5—C61.379 (7)C14—H170.95
C7—C81.557 (6)C15—H180.95
C7—C141.531 (6)C15—H190.95
C8—C131.530 (5)C15—H200.95
C8—C91.523 (6)C16—H210.95
C9—C101.529 (7)C16—H220.95
C10—C111.508 (8)C16—H230.95
C11—C121.522 (7)C17—H240.95
C12—C131.512 (7)C17—H250.95
C2—H10.95C17—H260.95
C3—H20.95
Cl1···O2i3.213 (5)H6···C23.0585
Cl1···N13.040 (5)H6···C63.0058
Cl1···C16ii3.571 (7)H6···C10viii3.0969
Cl1···H15i3.0489H6···H9viii2.4489
Cl1···H27i2.33 (5)H7···C12.9612
Cl1···H282.13 (6)H7···C23.0694
Cl1···H16i2.9232H7···H142.5556
Cl1···H17iii3.0457H8···O22.6469
Cl1···H19iii3.1281H8···H122.5775
Cl1···H22iii3.0347H9···H6viii2.4489
Cl1···H23ii3.0321H10···H25v2.5136
O2···Cl1iv3.213 (5)H10···C17viii3.0310
O2···C63.305 (7)H10···H26viii2.4336
O2···H1iv2.6100H11···C17xii3.0843
O2···H42.9021H11···H142.5706
O2···H5iv2.6842H11···H2x2.5728
O2···H82.6469H12···O22.6655
O2···H122.6655H12···C17v3.0211
O2···H162.4573H12···H82.5775
O2···H172.8912H12···H25v2.5645
N1···Cl13.040 (5)H12···H272.3022
C1···C163.324 (7)H13···C17xii3.0115
C2···C93.354 (8)H14···H52.3596
C6···C93.581 (7)H14···H72.5556
C6···O23.305 (7)H14···H112.5706
C9···C63.581 (7)H15···Cl1iv3.0489
C9···C23.354 (8)H15···C142.7795
C12···C17v3.561 (8)H15···H162.1711
C16···C13.324 (7)H15···H272.3200
C16···Cl1vi3.571 (7)H16···Cl1iv2.9232
C17···C12vii3.561 (8)H16···O22.4573
C1···H72.9612H16···C132.7089
C1···H62.5806H16···H152.1711
C1···H212.8102H16···H202.3180
C2···H212.9862H16···H272.3019
C2···H73.0694H17···O22.8912
C2···H63.0585H17···C62.5923
C5···H262.7418H17···H42.1829
C5···H242.7376H17···H192.5190
C6···H63.0058H17···H222.4969
C6···H172.5923H17···Cl1xi3.0457
C7···H212.7321H18···H232.4404
C10···H6viii3.0969H18···H3iii2.4314
C12···H272.78 (5)H19···H172.5190
C13···H162.7089H19···H222.4792
C14···H152.7795H19···Cl1xi3.1281
C14···H272.90 (5)H20···H162.3180
C14···H42.8292H21···C12.8102
C16···H52.9114H21···C22.9862
C17···H32.5044H21···C72.7321
C17···H11ix3.0843H21···H52.4261
C17···H12vii3.0211H22···H172.4969
C17···H13ix3.0115H22···H192.4792
C17···H10viii3.0310H22···Cl1xi3.0347
H1···O2i2.6100H23···H182.4404
H1···H52.3358H23···Cl1vi3.0321
H2···H11x2.5728H24···C52.7376
H3···C172.5044H24···H32.2855
H3···H242.2855H25···H10vii2.5136
H3···H262.3024H25···H12vii2.5645
H3···H18xi2.4314H26···C52.7418
H4···O22.9021H26···H32.3024
H4···C142.8292H26···H10viii2.4336
H4···H172.1829H27···Cl1iv2.33 (5)
H5···O2i2.6842H27···C122.78 (5)
H5···C162.9114H27···C142.90 (5)
H5···H12.3358H27···H5iv2.4751
H5···H142.3596H27···H122.3022
H5···H212.4261H27···H152.3200
H5···H27i2.4751H27···H162.3019
H5···H282.3874H28···Cl12.13 (6)
H6···C12.5806H28···H52.3874
C4—O1—C17117.0 (4)C10—C9—H6108.79
C8—O2—H27112 (3)C10—C9—H7108.55
C14—N1—C16113.3 (4)H6—C9—H7109.47
C15—N1—C16110.6 (4)C9—C10—H8108.72
C14—N1—C15109.7 (4)C9—C10—H9108.67
C14—N1—H28106 (3)C11—C10—H8109.31
C15—N1—H28103 (3)C11—C10—H9108.75
C16—N1—H28113 (4)H8—C10—H9109.46
C2—C1—C7120.4 (4)C10—C11—H10108.73
C6—C1—C7122.2 (4)C10—C11—H11109.65
C2—C1—C6117.4 (4)C12—C11—H10108.74
C1—C2—C3121.2 (4)C12—C11—H11109.52
C2—C3—C4120.4 (4)H10—C11—H11109.49
O1—C4—C3115.8 (4)C11—C12—H12109.27
C3—C4—C5118.9 (4)C11—C12—H13109.11
O1—C4—C5125.4 (4)C13—C12—H12109.02
C4—C5—C6120.9 (4)C13—C12—H13109.11
C1—C6—C5121.3 (4)H12—C12—H13109.48
C8—C7—C14109.3 (3)C8—C13—H14108.76
C1—C7—C8113.2 (3)C8—C13—H15108.64
C1—C7—C14113.4 (3)C12—C13—H14108.78
O2—C8—C9106.3 (3)C12—C13—H15108.41
O2—C8—C13110.2 (3)H14—C13—H15109.49
C7—C8—C9112.3 (3)N1—C14—H16108.19
C7—C8—C13110.2 (3)N1—C14—H17108.28
O2—C8—C7108.7 (3)C7—C14—H16108.24
C9—C8—C13109.1 (3)C7—C14—H17108.22
C8—C9—C10112.5 (4)H16—C14—H17109.47
C9—C10—C11111.9 (5)N1—C15—H18109.45
C10—C11—C12110.7 (4)N1—C15—H19109.60
C11—C12—C13110.8 (4)N1—C15—H20109.36
C8—C13—C12112.7 (4)H18—C15—H19109.49
N1—C14—C7114.4 (3)H18—C15—H20109.45
C1—C2—H1119.50H19—C15—H20109.48
C3—C2—H1119.33N1—C16—H21109.15
C2—C3—H2119.82N1—C16—H22109.44
C4—C3—H2119.82N1—C16—H23109.79
C4—C5—H3119.63H21—C16—H22109.50
C6—C5—H3119.50H21—C16—H23109.44
C1—C6—H4119.39H22—C16—H23109.50
C5—C6—H4119.30O1—C17—H24109.31
C1—C7—H5106.92O1—C17—H25109.39
C8—C7—H5106.88O1—C17—H26109.64
C14—C7—H5106.75H24—C17—H25109.47
C8—C9—H6108.96H24—C17—H26109.43
C8—C9—H7108.58H25—C17—H26109.58
C17—O1—C4—C3179.7 (4)C1—C7—C8—O280.2 (4)
C17—O1—C4—C50.8 (7)C1—C7—C8—C937.1 (5)
C16—N1—C14—C762.0 (5)C1—C7—C8—C13158.9 (3)
C15—N1—C14—C7173.9 (4)C14—C7—C8—O247.2 (4)
C6—C1—C2—C32.0 (7)C14—C7—C8—C9164.5 (4)
C7—C1—C2—C3176.8 (4)C14—C7—C8—C1373.7 (4)
C2—C1—C6—C51.5 (6)C1—C7—C14—N195.1 (4)
C7—C1—C6—C5177.3 (4)C8—C7—C14—N1137.6 (4)
C2—C1—C7—C8101.8 (5)O2—C8—C9—C1065.2 (5)
C2—C1—C7—C14133.0 (4)C7—C8—C9—C10176.1 (4)
C6—C1—C7—C877.0 (5)C13—C8—C9—C1053.7 (5)
C6—C1—C7—C1448.3 (5)O2—C8—C13—C1261.0 (4)
C1—C2—C3—C41.0 (7)C7—C8—C13—C12179.0 (4)
C2—C3—C4—O1179.9 (4)C9—C8—C13—C1255.4 (5)
C2—C3—C4—C50.6 (7)C8—C9—C10—C1155.0 (6)
O1—C4—C5—C6179.4 (5)C9—C10—C11—C1254.8 (6)
C3—C4—C5—C61.1 (7)C10—C11—C12—C1355.8 (6)
C4—C5—C6—C10.0 (7)C11—C12—C13—C857.1 (5)
Symmetry codes: (i) x1, y, z; (ii) x+1/2, y+3/2, z+1/2; (iii) x1/2, y+3/2, z+1/2; (iv) x+1, y, z; (v) x+1, y, z+1; (vi) x1/2, y+3/2, z1/2; (vii) x1, y, z1; (viii) x+2, y+2, z+1; (ix) x, y, z1; (x) x+1, y+2, z+1; (xi) x+1/2, y+3/2, z1/2; (xii) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H27···Cl1iv0.91 (5)2.33 (5)3.213 (5)164 (4)
N1—H28···Cl10.92 (6)2.13 (6)3.040 (5)169 (5)
Symmetry code: (iv) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC17H28NO2+·Cl
Mr313.87
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)5.797 (6), 26.074 (7), 11.722 (3)
β (°) 100.72 (5)
V3)1741 (2)
Z4
Radiation typeCu Kα
µ (mm1)1.97
Crystal size (mm)0.40 × 0.10 × 0.10
Data collection
DiffractometerRigaku AFC7S
diffractometer
Absorption correctionψ scan
(North, Phillips & Mathews, 1968)
Tmin, Tmax0.843, 0.996
No. of measured, independent and
observed [I > 1.30s(I)] reflections
3564, 3304, 3304
Rint0.078
(sin θ/λ)max1)0.610
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.068, 1.29
No. of reflections1816
No. of parameters199
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.40, 0.33

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1995), SIR92 (Altomare et al., 1993), TEXSAN.

Selected geometric parameters (Å, º) top
O1—C41.363 (6)N1—C151.486 (6)
O1—C171.426 (7)N1—C161.487 (7)
O2—C81.442 (5)N1—C141.495 (6)
C4—O1—C17117.0 (4)O1—C4—C5125.4 (4)
C14—N1—C16113.3 (4)O2—C8—C9106.3 (3)
C15—N1—C16110.6 (4)O2—C8—C13110.2 (3)
C14—N1—C15109.7 (4)O2—C8—C7108.7 (3)
O1—C4—C3115.8 (4)N1—C14—C7114.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H27···Cl1i0.91 (5)2.33 (5)3.213 (5)164 (4)
N1—H28···Cl10.92 (6)2.13 (6)3.040 (5)169 (5)
Symmetry code: (i) x+1, y, z.
Comparision of some torsion angles (°) in Form-I and Form-II top
angleForm-IForm-II
C16-N1-C14-C758.8 (5)62.0 (5)
C15-N1-C14-C7-177.0 (4)-173.9 (4)
C2-C1-C7-C8-107.3 (4)-101.8 (5)
C2-C1-C7-C14129.1 (4)133.0 (4)
C6-C1-C7-C871.7 (5)77.0 (5)
C6-C1-C7-C14-51.9 (5)-48.3 (5)
C1-C7-C14-N1-88.9 (4)-95.1 (4)
C8-C7-C14-N1144.7 (3)137.6 (4)
 

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