Literature DB >> 22058805

3-Amino-1-(4-bromo-phen-yl)-9,10-dihydro-phenanthrene-2,4-dicarbonitrile.

Abdullah M Asiri, Hassan M Faidallah, Abdulrahman O Al-Youbi, Seik Weng Ng.   

Abstract

In the title compound, C(22)H(14)BrN(3), the fused-ring system is buckled owing to the ethyl-ene linkage in the central ring; the two flanking aromatic rings are twisted by 25.9 (1) ° with respect to each other. The phenyl ring is twisted by 77.0 (1)° relative to the amino- and cyano-bearing aromatic ring. In the crystal, adjacent mol-ecules are linked by two N-H⋯N hydrogen bonds, generating a zigzag chain along [101].

Entities:  

Year:  2011        PMID： 22058805      PMCID： PMC3201339          DOI： 10.1107/S1600536811038517

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For two related compounds, see: Asiri et al. (2011a ▶,b ▶).

Experimental

Crystal data

C22H14BrN3 M = 400.27 Monoclinic, a = 13.7683 (5) Å b = 16.2557 (3) Å c = 9.7945 (4) Å β = 127.546 (6)° V = 1738.07 (17) Å3 Z = 4 Cu Kα radiation μ = 3.29 mm−1 T = 100 K 0.20 × 0.20 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.559, T max = 0.559 2976 measured reflections 2195 independent reflections 2187 reflections with I > 2σ(I) R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.021 wR(F 2) = 0.056 S = 1.08 2195 reflections 243 parameters 2 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.22 e Å−3 Δρmin = −0.61 e Å−3 Absolute structure: Flack (Flack, 1983 ▶), 482 Friedel pairs Flack parameter: −0.024 (14) Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811038517/bt5646sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811038517/bt5646Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811038517/bt5646Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C22H14BrN3F(000) = 808
Mr = 400.27Dx = 1.530 Mg m−3
Monoclinic, CcCu Kα radiation, λ = 1.54184 Å
Hall symbol: C -2ycCell parameters from 2539 reflections
a = 13.7683 (5) Åθ = 4.9–74.2°
b = 16.2557 (3) ŵ = 3.29 mm−1
c = 9.7945 (4) ÅT = 100 K
β = 127.546 (6)°Prism, orange
V = 1738.07 (17) Å30.20 × 0.20 × 0.20 mm
Z = 4
Agilent SuperNova Dual diffractometer with Atlas detector2195 independent reflections
Radiation source: SuperNova (Cu) X-ray Source2187 reflections with I > 2σ(I)
MirrorRint = 0.012
Detector resolution: 10.4041 pixels mm-1θmax = 74.4°, θmin = 4.9°
ω scanh = −17→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)k = −11→20
Tmin = 0.559, Tmax = 0.559l = −11→12
2976 measured reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.021H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.056w = 1/[σ2(Fo2) + (0.0393P)2 + 0.2403P] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
2195 reflectionsΔρmax = 0.22 e Å−3
243 parametersΔρmin = −0.61 e Å−3
2 restraintsAbsolute structure: Flack (Flack, 1983), 482 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.024 (14)
xyzUiso*/Ueq
Br10.00008 (3)0.303704 (13)0.00088 (3)0.02570 (9)
N10.8004 (2)0.69430 (12)1.0721 (3)0.0189 (4)
N20.5320 (2)0.70911 (13)0.6833 (3)0.0173 (4)
H10.460 (3)0.739 (2)0.618 (4)0.018 (7)*
H20.597 (3)0.738 (2)0.761 (5)0.024 (8)*
N30.2436 (2)0.64780 (13)0.3201 (3)0.0245 (5)
C10.5286 (2)0.36690 (15)0.8140 (3)0.0172 (5)
H1A0.47530.33680.70360.021*
H1B0.49640.35810.87970.021*
C20.6591 (2)0.33350 (15)0.9166 (3)0.0202 (5)
H2A0.66040.27480.94470.024*
H2B0.68910.33770.84720.024*
C30.7407 (2)0.38245 (14)1.0797 (3)0.0168 (5)
C40.8329 (2)0.34500 (16)1.2344 (4)0.0217 (5)
H40.84620.28751.23640.026*
C50.9058 (2)0.38981 (17)1.3858 (3)0.0221 (5)
H50.97000.36351.48970.026*
C60.8845 (2)0.47317 (16)1.3845 (3)0.0209 (5)
H60.93240.50401.48830.025*
C70.7926 (2)0.51166 (15)1.2307 (3)0.0167 (5)
H70.77800.56871.23090.020*
C80.7217 (2)0.46789 (13)1.0763 (3)0.0144 (4)
C90.6244 (2)0.50717 (14)0.9095 (3)0.0130 (4)
C100.6259 (2)0.59116 (14)0.8755 (3)0.0131 (4)
C110.5282 (2)0.62902 (15)0.7197 (3)0.0133 (4)
C120.4277 (2)0.57892 (14)0.5984 (3)0.0142 (4)
C130.4282 (2)0.49398 (15)0.6262 (3)0.0162 (5)
C140.5264 (2)0.45766 (14)0.7787 (3)0.0166 (4)
C150.7262 (2)0.64517 (14)0.9918 (3)0.0137 (4)
C160.3254 (2)0.61565 (15)0.4420 (3)0.0174 (5)
C170.3244 (2)0.44469 (14)0.4820 (3)0.0143 (4)
C180.3423 (2)0.39889 (15)0.3792 (3)0.0183 (5)
H180.42160.39670.40750.022*
C190.2471 (2)0.35638 (14)0.2367 (3)0.0185 (5)
H190.26010.32530.16700.022*
C200.1321 (2)0.36031 (14)0.1981 (3)0.0166 (5)
C210.1114 (2)0.40498 (17)0.2974 (3)0.0238 (5)
H210.03180.40710.26820.029*
C220.2085 (2)0.44712 (17)0.4412 (3)0.0212 (5)
H220.19530.47760.51140.025*
U11U22U33U12U13U23
Br10.02085 (13)0.02220 (13)0.01646 (13)−0.00648 (12)0.00229 (10)−0.00716 (12)
N10.0175 (11)0.0161 (11)0.0163 (11)0.0000 (8)0.0068 (10)0.0001 (8)
N20.0141 (10)0.0118 (9)0.0155 (11)0.0002 (8)0.0036 (9)0.0002 (8)
N30.0210 (11)0.0174 (10)0.0201 (11)0.0007 (9)0.0048 (10)0.0001 (9)
C10.0180 (12)0.0132 (11)0.0159 (11)−0.0025 (9)0.0079 (10)−0.0014 (9)
C20.0217 (12)0.0143 (11)0.0213 (13)−0.0016 (10)0.0114 (11)−0.0011 (10)
C30.0180 (12)0.0132 (11)0.0187 (12)−0.0004 (9)0.0110 (11)0.0018 (9)
C40.0171 (11)0.0202 (12)0.0250 (13)0.0042 (10)0.0115 (11)0.0090 (11)
C50.0191 (12)0.0238 (13)0.0197 (12)0.0009 (10)0.0100 (11)0.0105 (10)
C60.0184 (11)0.0261 (13)0.0142 (11)−0.0025 (10)0.0079 (10)0.0019 (10)
C70.0159 (10)0.0162 (11)0.0165 (11)−0.0016 (9)0.0091 (10)0.0009 (9)
C80.0127 (10)0.0134 (11)0.0160 (11)−0.0005 (9)0.0081 (9)0.0024 (9)
C90.0121 (11)0.0131 (10)0.0138 (11)0.0014 (9)0.0079 (10)−0.0001 (9)
C100.0126 (10)0.0133 (10)0.0129 (10)−0.0014 (9)0.0075 (9)−0.0030 (9)
C110.0130 (11)0.0132 (10)0.0140 (11)−0.0003 (9)0.0084 (10)−0.0019 (9)
C120.0136 (10)0.0140 (11)0.0114 (11)0.0009 (8)0.0057 (9)0.0006 (8)
C130.0146 (11)0.0131 (11)0.0157 (11)−0.0013 (9)0.0066 (10)−0.0029 (10)
C140.0173 (10)0.0139 (11)0.0165 (11)−0.0023 (9)0.0093 (10)−0.0007 (9)
C150.0140 (11)0.0116 (10)0.0123 (11)0.0025 (9)0.0063 (10)0.0007 (9)
C160.0173 (11)0.0133 (10)0.0176 (11)−0.0026 (9)0.0085 (10)−0.0045 (10)
C170.0149 (10)0.0104 (10)0.0121 (10)−0.0007 (9)0.0055 (9)0.0000 (9)
C180.0143 (11)0.0174 (11)0.0193 (12)−0.0003 (9)0.0082 (10)−0.0023 (10)
C190.0208 (11)0.0168 (12)0.0167 (11)−0.0005 (10)0.0108 (10)−0.0031 (10)
C200.0165 (11)0.0115 (10)0.0115 (11)−0.0049 (9)0.0032 (9)−0.0006 (9)
C210.0161 (11)0.0328 (14)0.0193 (12)−0.0061 (11)0.0091 (10)−0.0056 (11)
C220.0187 (12)0.0270 (13)0.0180 (12)−0.0043 (10)0.0111 (10)−0.0071 (10)
Br1—C201.898 (2)C7—H70.9500
N1—C151.149 (3)C8—C91.485 (3)
N2—C111.359 (3)C9—C101.408 (3)
N2—H10.93 (3)C9—C141.415 (3)
N2—H20.88 (4)C10—C111.420 (3)
N3—C161.152 (4)C10—C151.435 (3)
C1—C141.511 (3)C11—C121.410 (3)
C1—C21.528 (4)C12—C131.407 (3)
C1—H1A0.9900C12—C161.434 (3)
C1—H1B0.9900C13—C141.395 (3)
C2—C31.503 (3)C13—C171.489 (3)
C2—H2A0.9900C17—C221.389 (3)
C2—H2B0.9900C17—C181.390 (3)
C3—C41.390 (4)C18—C191.384 (3)
C3—C81.410 (3)C18—H180.9500
C4—C51.387 (4)C19—C201.387 (3)
C4—H40.9500C19—H190.9500
C5—C61.385 (4)C20—C211.376 (4)
C5—H50.9500C21—C221.395 (4)
C6—C71.392 (4)C21—H210.9500
C6—H60.9500C22—H220.9500
C7—C81.395 (3)
C11—N2—H1119 (2)C9—C10—C11122.2 (2)
C11—N2—H2117 (2)C9—C10—C15123.5 (2)
H1—N2—H2115 (3)C11—C10—C15114.3 (2)
C14—C1—C2110.4 (2)N2—C11—C12120.5 (2)
C14—C1—H1A109.6N2—C11—C10122.3 (2)
C2—C1—H1A109.6C12—C11—C10117.1 (2)
C14—C1—H1B109.6C11—C12—C13121.2 (2)
C2—C1—H1B109.6C11—C12—C16118.7 (2)
H1A—C1—H1B108.1C13—C12—C16120.1 (2)
C3—C2—C1109.2 (2)C14—C13—C12120.6 (2)
C3—C2—H2A109.8C14—C13—C17122.1 (2)
C1—C2—H2A109.8C12—C13—C17117.1 (2)
C3—C2—H2B109.8C13—C14—C9119.7 (2)
C1—C2—H2B109.8C13—C14—C1121.9 (2)
H2A—C2—H2B108.3C9—C14—C1118.2 (2)
C4—C3—C8119.3 (2)N1—C15—C10173.1 (2)
C4—C3—C2121.4 (2)N3—C16—C12177.3 (3)
C8—C3—C2119.3 (2)C22—C17—C18119.1 (2)
C3—C4—C5121.4 (2)C22—C17—C13121.9 (2)
C3—C4—H4119.3C18—C17—C13118.9 (2)
C5—C4—H4119.3C19—C18—C17121.4 (2)
C6—C5—C4119.5 (2)C19—C18—H18119.3
C6—C5—H5120.2C17—C18—H18119.3
C4—C5—H5120.2C18—C19—C20118.3 (2)
C5—C6—C7119.8 (2)C18—C19—H19120.9
C5—C6—H6120.1C20—C19—H19120.9
C7—C6—H6120.1C21—C20—C19121.7 (2)
C6—C7—C8121.2 (2)C21—C20—Br1119.50 (19)
C6—C7—H7119.4C19—C20—Br1118.77 (18)
C8—C7—H7119.4C20—C21—C22119.3 (2)
C7—C8—C3118.6 (2)C20—C21—H21120.4
C7—C8—C9122.7 (2)C22—C21—H21120.4
C3—C8—C9118.7 (2)C17—C22—C21120.2 (2)
C10—C9—C14118.7 (2)C17—C22—H22119.9
C10—C9—C8122.9 (2)C21—C22—H22119.9
C14—C9—C8118.3 (2)
C14—C1—C2—C356.3 (3)C10—C11—C12—C16177.9 (2)
C1—C2—C3—C4141.2 (2)C11—C12—C13—C142.9 (3)
C1—C2—C3—C8−37.6 (3)C16—C12—C13—C14−179.2 (2)
C8—C3—C4—C50.6 (4)C11—C12—C13—C17−173.1 (2)
C2—C3—C4—C5−178.1 (2)C16—C12—C13—C174.9 (3)
C3—C4—C5—C61.8 (4)C12—C13—C14—C92.4 (3)
C4—C5—C6—C7−1.9 (4)C17—C13—C14—C9178.1 (2)
C5—C6—C7—C8−0.6 (4)C12—C13—C14—C1178.8 (2)
C6—C7—C8—C33.0 (3)C17—C13—C14—C1−5.5 (4)
C6—C7—C8—C9−178.9 (2)C10—C9—C14—C13−6.0 (3)
C4—C3—C8—C7−3.0 (3)C8—C9—C14—C13174.4 (2)
C2—C3—C8—C7175.8 (2)C10—C9—C14—C1177.4 (2)
C4—C3—C8—C9178.9 (2)C8—C9—C14—C1−2.2 (3)
C2—C3—C8—C9−2.3 (3)C2—C1—C14—C13145.4 (2)
C7—C8—C9—C1026.4 (3)C2—C1—C14—C9−38.2 (3)
C3—C8—C9—C10−155.6 (2)C14—C13—C17—C22108.9 (3)
C7—C8—C9—C14−154.1 (2)C12—C13—C17—C22−75.2 (3)
C3—C8—C9—C1424.0 (3)C14—C13—C17—C18−75.0 (3)
C14—C9—C10—C114.7 (3)C12—C13—C17—C18100.9 (3)
C8—C9—C10—C11−175.7 (2)C22—C17—C18—C190.6 (4)
C14—C9—C10—C15−173.7 (2)C13—C17—C18—C19−175.6 (2)
C8—C9—C10—C155.8 (3)C17—C18—C19—C20−0.1 (4)
C9—C10—C11—N2−176.9 (2)C18—C19—C20—C210.0 (4)
C15—C10—C11—N21.7 (3)C18—C19—C20—Br1179.03 (17)
C9—C10—C11—C120.3 (3)C19—C20—C21—C22−0.4 (4)
C15—C10—C11—C12178.9 (2)Br1—C20—C21—C22−179.4 (2)
N2—C11—C12—C13173.1 (2)C18—C17—C22—C21−0.9 (4)
C10—C11—C12—C13−4.2 (3)C13—C17—C22—C21175.1 (2)
N2—C11—C12—C16−4.8 (3)C20—C21—C22—C170.8 (4)
D—H···AD—HH···AD···AD—H···A
N2—H1···N1i0.93 (3)2.23 (3)3.097 (3)155 (3)
N2—H2···N3ii0.88 (4)2.54 (4)3.307 (3)147 (3)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N2—H1⋯N1i0.93 (3)2.23 (3)3.097 (3)155 (3)
N2—H2⋯N3ii0.88 (4)2.54 (4)3.307 (3)147 (3)

Symmetry codes: (i) ; (ii) .

  3 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  3-Amino-1-(2H-1,3-benzodioxol-5-yl)-9,10-dihydro-phenanthrene-2,4-dicarbonitrile.

Authors:  Abdullah M Asiri; Abdulrahman O Al-Youbi; Hassan M Faidallah; Seik Weng Ng; Edward R T Tiekink
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-08-27

3.  3-Amino-1-(4-meth-oxy-phen-yl)-9,10-dihydro-phenanthrene-2,4-dicarbonitrile.

Authors:  Abdullah M Asiri; Abdulrahman O Al-Youbi; Hassan M Faidallah; Seik Weng Ng; Edward R T Tiekink
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-08-27
  3 in total
  1 in total

1.  An efficient approach to the synthesis of highly congested 9,10-dihydrophenanthrene-2,4-dicarbonitriles and their biological evaluation as antimicrobial agents.

Authors:  Hassan M Faidallah; Khalid M A Al-Shaikh; Tariq R Sobahi; Khalid A Khan; Abdullah M Asiri
Journal:  Molecules       Date:  2013-12-16       Impact factor: 4.411
  1 in total

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