Literature DB >> 26279919

Crystal structure of 3-amino-1-(4-chloro-phen-yl)-1H-benzo[f]chromene-2-carbo-nitrile.

Mehmet Akkurt1, Peter N Horton2, Shaaban K Mohamed3, Sabry H H Younes4, Mustafa R Albayati5.   

Abstract

In the title compound, C20H13ClN2O, the chloro-benzene ring is almost perpendicular to the mean plane of the naphthalene ring system, making a dihedral angle of 81.26 (8)°. The 4H-pyran ring fused with the naphthalene ring system has a flattened boat conformation. In the crystal, N-H⋯N hydrogen bonds generate chains along the b-axis direction. Further N-H⋯N hydrogen bonds link these chains into sheets parallel to (010). The crystal packing also features C-H⋯π inter-actions. The crystal studied was an inversion twin with a 0.557 (16):0.443 (16) domain ratio.

Entities:  

Keywords:  C—H⋯π inter­actions; N—H⋯N hydrogen bonds; chromene compounds; crystal structure

Year:  2015        PMID： 26279919      PMCID： PMC4518915          DOI： 10.1107/S2056989015011159

Source DB:  PubMed          Journal:  Acta Crystallogr E Crystallogr Commun


Related literature

For the synthesis and biological importance of chromene compounds, see, for example: Ellis (1977 ▸); Singh et al. (2010 ▸); Kidwai et al. (2010 ▸); Lácová et al. (2005 ▸); Dell & Smith (1993a ▸,b ▸); Al-Soud et al. (2006 ▸); Eiden & Denk (1991 ▸); Bruhlmann et al. (200); (Kesten et al. (1999 ▸); Bruhlmann et al. (2001 ▸). For a similar structure, see: Akkurt et al. (2013 ▸).

Experimental

Crystal data

C20H13ClN2O M = 332.77 Monoclinic, a = 10.056 (7) Å b = 6.172 (3) Å c = 12.751 (6) Å β = 99.641 (17)° V = 780.2 (8) Å3 Z = 2 Cu Kα radiation μ = 2.23 mm−1 T = 100 K 0.32 × 0.12 × 0.10 mm

Data collection

Rigaku AFC11 diffractometer Absorption correction: multi-scan (CrystalClearSM Expert; Rigaku, 2012 ▸) T min = 0.948, T max = 1.000 11415 measured reflections 2558 independent reflections 2500 reflections with I > 2σ(I) R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.028 wR(F 2) = 0.075 S = 1.06 2558 reflections 219 parameters 1 restraint H-atom parameters constrained Δρmax = 0.17 e Å−3 Δρmin = −0.22 e Å−3 Absolute structure: Refined as an inversion twin. Absolute structure parameter: 0.443 (16)

Data collection: CrystalClearSM Expert (Rigaku, 2012 ▸); cell refinement: CrystalClearSM Expert; data reduction: CrystalClearSM Expert; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015011159/sj5465sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015011159/sj5465Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S2056989015011159/sj5465Isup3.cml Click here for additional data file. . DOI: 10.1107/S2056989015011159/sj5465fig1.tif View of the title compound with the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. Click here for additional data file. a . DOI: 10.1107/S2056989015011159/sj5465fig2.tif Crystal packing of the title compound viewed along the a axis, with hydrogen bonds drawn as dashed lines. Click here for additional data file. b . DOI: 10.1107/S2056989015011159/sj5465fig3.tif A view of the packing showing mol­ecules stacked along the b axis. CCDC reference: 1405640 Additional supporting information: crystallographic information; 3D view; checkCIF report
C20H13ClN2OF(000) = 344
Mr = 332.77Dx = 1.416 Mg m−3
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ybCell parameters from 1130 reflections
a = 10.056 (7) Åθ = 21.5–68.7°
b = 6.172 (3) ŵ = 2.23 mm−1
c = 12.751 (6) ÅT = 100 K
β = 99.641 (17)°Block, light brown
V = 780.2 (8) Å30.32 × 0.12 × 0.10 mm
Z = 2
Rigaku AFC11 diffractometer2558 independent reflections
Radiation source: Rotating Anode2500 reflections with I > 2σ(I)
Detector resolution: 22.2222 pixels mm-1Rint = 0.032
profile data from ω–scansθmax = 66.6°, θmin = 3.5°
Absorption correction: multi-scan (CrystalClearSM Expert; Rigaku, 2012)h = −11→11
Tmin = 0.948, Tmax = 1.000k = −7→7
11415 measured reflectionsl = −15→15
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.028w = 1/[σ2(Fo2) + (0.0548P)2 + 0.1146P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.075(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.17 e Å−3
2558 reflectionsΔρmin = −0.22 e Å−3
219 parametersAbsolute structure: Refined as an inversion twin.
1 restraintAbsolute structure parameter: 0.443 (16)
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.
xyzUiso*/Ueq
Cl1−0.24323 (5)0.55572 (12)0.52362 (5)0.0334 (2)
O10.45126 (15)1.1239 (3)0.79232 (11)0.0189 (5)
N10.55640 (19)1.0368 (4)0.65748 (14)0.0214 (6)
N20.4506 (2)0.4950 (3)0.57819 (16)0.0257 (6)
C10.4675 (2)0.9698 (4)0.71956 (16)0.0166 (6)
C20.4046 (2)0.7754 (4)0.71666 (16)0.0156 (6)
C30.3043 (2)0.7152 (4)0.78878 (16)0.0149 (6)
C40.3101 (2)0.8809 (4)0.87613 (16)0.0144 (6)
C50.38290 (19)1.0685 (4)0.87480 (15)0.0156 (6)
C60.3992 (2)1.2209 (4)0.95817 (16)0.0174 (6)
C70.3399 (2)1.1839 (4)1.04481 (17)0.0180 (6)
C80.2613 (2)0.9965 (4)1.05160 (17)0.0175 (6)
C90.1991 (2)0.9560 (4)1.14178 (17)0.0212 (7)
C100.1240 (2)0.7733 (5)1.14784 (18)0.0240 (7)
C110.1072 (2)0.6218 (4)1.06388 (17)0.0214 (7)
C120.1664 (2)0.6555 (4)0.97558 (17)0.0175 (6)
C130.24556 (19)0.8423 (4)0.96678 (16)0.0149 (6)
C140.4305 (2)0.6224 (4)0.63990 (16)0.0179 (6)
C150.1641 (2)0.6784 (4)0.72333 (16)0.0150 (6)
C160.1348 (2)0.4796 (4)0.67440 (16)0.0174 (6)
C170.0094 (2)0.4409 (4)0.61165 (17)0.0202 (7)
C18−0.0858 (2)0.6031 (4)0.60027 (16)0.0204 (7)
C19−0.0595 (2)0.8037 (4)0.64830 (17)0.0201 (7)
C200.0667 (2)0.8403 (4)0.70949 (16)0.0176 (6)
H1A0.536500.978500.593400.0260*
H1B0.552801.179500.651300.0260*
H30.334500.574000.823300.0180*
H60.451101.348200.953900.0210*
H70.351501.285501.101500.0220*
H90.209801.057401.198600.0250*
H100.083000.748301.208700.0290*
H110.054600.495401.068400.0260*
H120.154000.552000.919600.0210*
H160.200900.368200.683700.0210*
H17−0.009800.305100.577400.0240*
H19−0.126300.914100.639600.0240*
H200.086400.977500.742100.0210*
U11U22U33U12U13U23
Cl10.0198 (3)0.0457 (4)0.0312 (3)−0.0081 (3)−0.0061 (2)−0.0053 (3)
O10.0234 (8)0.0193 (9)0.0146 (7)−0.0026 (6)0.0054 (6)−0.0006 (6)
N10.0250 (9)0.0222 (11)0.0189 (9)−0.0033 (9)0.0088 (7)0.0002 (8)
N20.0313 (11)0.0258 (12)0.0233 (10)−0.0026 (9)0.0146 (8)−0.0028 (9)
C10.0160 (10)0.0226 (12)0.0110 (9)0.0030 (9)0.0016 (8)0.0005 (8)
C20.0135 (10)0.0219 (12)0.0113 (9)0.0010 (9)0.0019 (7)−0.0013 (8)
C30.0146 (11)0.0167 (12)0.0132 (9)0.0009 (8)0.0020 (8)0.0009 (8)
C40.0122 (9)0.0183 (11)0.0117 (10)0.0041 (9)−0.0009 (7)0.0001 (8)
C50.0139 (9)0.0206 (12)0.0118 (9)0.0024 (9)0.0010 (7)0.0023 (9)
C60.0152 (11)0.0182 (12)0.0172 (10)0.0019 (8)−0.0021 (8)−0.0006 (9)
C70.0190 (11)0.0195 (12)0.0137 (9)0.0032 (9)−0.0021 (8)−0.0044 (9)
C80.0158 (10)0.0228 (13)0.0131 (9)0.0045 (9)0.0000 (8)−0.0005 (8)
C90.0228 (12)0.0261 (13)0.0152 (10)0.0025 (10)0.0044 (9)−0.0047 (10)
C100.0257 (13)0.0302 (14)0.0181 (11)0.0012 (11)0.0091 (9)−0.0003 (10)
C110.0201 (11)0.0249 (13)0.0207 (11)−0.0013 (9)0.0078 (9)0.0004 (9)
C120.0169 (10)0.0192 (12)0.0163 (10)0.0012 (9)0.0021 (8)−0.0017 (9)
C130.0125 (10)0.0176 (12)0.0138 (10)0.0035 (8)0.0003 (8)0.0006 (8)
C140.0176 (10)0.0200 (13)0.0170 (10)−0.0005 (8)0.0058 (8)0.0019 (9)
C150.0151 (10)0.0213 (12)0.0089 (9)−0.0017 (9)0.0032 (7)0.0011 (8)
C160.0180 (11)0.0197 (12)0.0155 (10)−0.0005 (9)0.0056 (8)−0.0008 (9)
C170.0242 (12)0.0228 (13)0.0145 (10)−0.0083 (10)0.0060 (8)−0.0034 (9)
C180.0165 (10)0.0325 (15)0.0119 (9)−0.0063 (9)0.0018 (8)−0.0008 (9)
C190.0179 (11)0.0248 (13)0.0175 (11)0.0003 (10)0.0023 (8)0.0016 (9)
C200.0189 (11)0.0187 (12)0.0149 (10)−0.0007 (9)0.0022 (8)−0.0011 (9)
Cl1—C181.740 (2)C10—C111.410 (4)
O1—C11.358 (3)C11—C121.375 (3)
O1—C51.392 (3)C12—C131.416 (3)
N1—C11.354 (3)C15—C201.390 (3)
N2—C141.154 (3)C15—C161.386 (3)
C1—C21.354 (3)C16—C171.396 (3)
N1—H1B0.8800C17—C181.376 (3)
N1—H1A0.8800C18—C191.387 (4)
C2—C141.415 (3)C19—C201.392 (3)
C2—C31.520 (3)C3—H31.0000
C3—C41.506 (3)C6—H60.9500
C3—C151.530 (3)C7—H70.9500
C4—C131.437 (3)C9—H90.9500
C4—C51.372 (3)C10—H100.9500
C5—C61.408 (3)C11—H110.9500
C6—C71.360 (3)C12—H120.9500
C7—C81.412 (3)C16—H160.9500
C8—C131.429 (3)C17—H170.9500
C8—C91.420 (3)C19—H190.9500
C9—C101.367 (4)C20—H200.9500
C1—O1—C5118.39 (19)C3—C15—C20121.9 (2)
O1—C1—N1110.6 (2)C16—C15—C20119.17 (19)
O1—C1—C2122.03 (19)C15—C16—C17120.9 (2)
N1—C1—C2127.3 (2)C16—C17—C18118.8 (2)
H1A—N1—H1B109.00Cl1—C18—C19119.09 (17)
C1—N1—H1A110.00Cl1—C18—C17119.23 (18)
C1—N1—H1B110.00C17—C18—C19121.7 (2)
C1—C2—C3123.7 (2)C18—C19—C20118.7 (2)
C1—C2—C14118.10 (19)C15—C20—C19120.8 (2)
C3—C2—C14118.2 (2)C2—C3—H3107.00
C2—C3—C4109.51 (19)C4—C3—H3107.00
C4—C3—C15114.97 (18)C15—C3—H3107.00
C2—C3—C15110.51 (17)C5—C6—H6120.00
C5—C4—C13117.6 (2)C7—C6—H6120.00
C3—C4—C5121.25 (18)C6—C7—H7120.00
C3—C4—C13121.0 (2)C8—C7—H7120.00
O1—C5—C4123.29 (19)C8—C9—H9120.00
O1—C5—C6113.4 (2)C10—C9—H9120.00
C4—C5—C6123.33 (19)C9—C10—H10120.00
C5—C6—C7119.3 (2)C11—C10—H10120.00
C6—C7—C8120.9 (2)C10—C11—H11120.00
C9—C8—C13119.2 (2)C12—C11—H11120.00
C7—C8—C9121.4 (2)C11—C12—H12120.00
C7—C8—C13119.43 (19)C13—C12—H12120.00
C8—C9—C10120.9 (2)C15—C16—H16120.00
C9—C10—C11120.1 (2)C17—C16—H16120.00
C10—C11—C12120.6 (2)C16—C17—H17121.00
C11—C12—C13121.0 (2)C18—C17—H17121.00
C8—C13—C12118.33 (19)C18—C19—H19121.00
C4—C13—C12122.3 (2)C20—C19—H19121.00
C4—C13—C8119.4 (2)C15—C20—H20120.00
N2—C14—C2178.9 (2)C19—C20—H20120.00
C3—C15—C16119.0 (2)
C5—O1—C1—N1−168.57 (17)C13—C4—C5—O1179.31 (19)
C5—O1—C1—C28.9 (3)O1—C5—C6—C7−178.62 (19)
C1—O1—C5—C6165.88 (18)C4—C5—C6—C7−0.4 (3)
C1—O1—C5—C4−12.3 (3)C5—C6—C7—C8−0.7 (3)
O1—C1—C2—C14−178.26 (19)C6—C7—C8—C9179.9 (2)
O1—C1—C2—C33.8 (3)C6—C7—C8—C130.9 (3)
N1—C1—C2—C14−1.2 (3)C7—C8—C9—C10−179.5 (2)
N1—C1—C2—C3−179.1 (2)C13—C8—C9—C10−0.5 (3)
C1—C2—C3—C15115.5 (2)C7—C8—C13—C40.0 (3)
C1—C2—C3—C4−12.1 (3)C7—C8—C13—C12179.9 (2)
C14—C2—C3—C4169.96 (19)C9—C8—C13—C4−179.0 (2)
C14—C2—C3—C15−62.4 (3)C9—C8—C13—C120.9 (3)
C2—C3—C4—C58.7 (3)C8—C9—C10—C11−0.1 (3)
C15—C3—C4—C1367.1 (3)C9—C10—C11—C120.3 (3)
C2—C3—C15—C1682.1 (3)C10—C11—C12—C130.1 (3)
C2—C3—C15—C20−96.3 (2)C11—C12—C13—C4179.2 (2)
C4—C3—C15—C16−153.4 (2)C11—C12—C13—C8−0.7 (3)
C4—C3—C15—C2028.3 (3)C3—C15—C16—C17−178.31 (19)
C2—C3—C4—C13−167.82 (19)C20—C15—C16—C170.1 (3)
C15—C3—C4—C5−116.4 (2)C3—C15—C20—C19179.08 (19)
C3—C4—C5—O12.7 (3)C16—C15—C20—C190.7 (3)
C13—C4—C5—C61.3 (3)C15—C16—C17—C18−0.9 (3)
C3—C4—C13—C8175.60 (19)C16—C17—C18—Cl1−179.20 (16)
C3—C4—C13—C12−4.3 (3)C16—C17—C18—C190.8 (3)
C5—C4—C13—C8−1.1 (3)Cl1—C18—C19—C20−180.00 (17)
C5—C4—C13—C12179.1 (2)C17—C18—C19—C20−0.1 (3)
C3—C4—C5—C6−175.4 (2)C18—C19—C20—C15−0.7 (3)
D—H···AD—HH···AD···AD—H···A
N1—H1A···N2i0.882.223.005 (3)148
N1—H1B···N2ii0.882.323.129 (4)152
C6—H6···Cg2iii0.952.603.401 (3)142
C11—H11···Cg3iv0.952.903.636 (3)135
Table 1

Hydrogen-bond geometry (, )

Cg2 and Cg3 are the centroids of the C4C8/C13 and C8C13 rings, respectively.

DHA DHHA D A DHA
N1H1AN2i 0.882.223.005(3)148
N1H1BN2ii 0.882.323.129(4)152
C6H6Cg2iii 0.952.603.401(3)142
C11H11Cg3iv 0.952.903.636(3)135

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

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5.  [Synthesis of CNS-activity of pyran derivatives: 6,8-dioxabicyclo(3,2,1)octane].

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6.  Crystal structure refinement with SHELXL.

Authors:  George M Sheldrick
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7.  3-Amino-1-phenyl-1H-benzo[f]chromene-2-carbonitrile.

Authors:  Mehmet Akkurt; Alan R Kennedy; Shaaban Kamel Mohamed; Sabry H H Younes; Gary J Miller
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