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The title compound, C23H27BrN2O2, has been synthesized by the reaction of 3,3,6,6-tetra­meth­yl-9-(4-bromo­phen­yl)-1,8-dioxo-2,3,4,5,6,7-hexa­hydro­anthene with hydrazine in alcohol under microwave irradiation. X-ray analysis reveals that the dihydro­pyridine ring adopts a boat conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680501202X/ob6497sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680501202X/ob6497Isup2.hkl
Contains datablock I

CCDC reference: 272053

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.042
  • wR factor = 0.102
  • Data-to-parameter ratio = 17.8

checkCIF/PLATON results

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Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.80 mm PLAT480_ALERT_4_C Long H...A H-Bond Reported H20B .. BR1 .. 2.98 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2000-2003); 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.

10-Amino-3,3,6,6-tetramethyl-9-(4-bromophenyl)-3,4,5,6,9,10-hexahydroacridine- 1,8(2H,7H)-dione top
Crystal data top
C23H27BrN2O2Dx = 1.422 Mg m3
Mr = 443.38Melting point = 553–554 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71070 Å
Hall symbol: -p 2ac 2abCell parameters from 17928 reflections
a = 11.8053 (10) Åθ = 3.0–27.5°
b = 15.6404 (15) ŵ = 2.01 mm1
c = 22.432 (2) ÅT = 193 K
V = 4141.8 (6) Å3Chunk, yellow
Z = 80.80 × 0.60 × 0.50 mm
F(000) = 1840
Data collection top
Rigaku Mercury
diffractometer
4743 independent reflections
Radiation source: fine-focus sealed tube4372 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 7.31 pixels mm-1θmax = 27.5°, θmin = 3.2°
ω scansh = 1515
Absorption correction: multi-scan
(Jacobson, 1998)
k = 1820
Tmin = 0.251, Tmax = 0.367l = 2329
43797 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H atoms treated by a mixture of independent and constrained refinement
S = 1.16 w = 1/[σ2(Fo2) + (0.0421P)2 + 3.1966P]
where P = (Fo2 + 2Fc2)/3
4743 reflections(Δ/σ)max = 0.002
266 parametersΔρmax = 0.77 e Å3
0 restraintsΔρmin = 0.84 e Å3
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*/Ueq
Br10.73075 (2)0.394197 (17)0.717748 (12)0.04261 (11)
O10.40897 (15)0.24985 (12)0.45248 (7)0.0384 (4)
O20.35654 (14)0.05231 (10)0.62079 (7)0.0334 (4)
N10.14650 (14)0.30821 (10)0.60544 (7)0.0213 (3)
N20.05666 (16)0.35757 (12)0.62989 (8)0.0252 (4)
C10.19740 (17)0.32965 (13)0.55150 (9)0.0214 (4)
C20.28796 (17)0.28403 (13)0.53208 (9)0.0227 (4)
C30.34559 (17)0.22150 (13)0.57390 (9)0.0231 (4)
H30.38210.17570.54940.028*
C40.25607 (17)0.18115 (13)0.61207 (9)0.0217 (4)
C50.16373 (17)0.22707 (12)0.62948 (9)0.0215 (4)
C60.33166 (19)0.29506 (14)0.47198 (9)0.0282 (4)
C70.27664 (19)0.36195 (15)0.43280 (10)0.0301 (5)
H7A0.21600.33450.40910.036*
H7B0.33390.38440.40460.036*
C80.22555 (18)0.43706 (14)0.46778 (9)0.0273 (4)
C90.14619 (18)0.40181 (13)0.51624 (9)0.0249 (4)
H9A0.12590.44870.54390.030*
H9B0.07550.38150.49720.030*
C100.27002 (18)0.09297 (13)0.63196 (9)0.0249 (4)
C110.1718 (2)0.05280 (14)0.66483 (10)0.0305 (5)
H11A0.19970.00300.68770.037*
H11B0.11580.03170.63540.037*
C120.11326 (19)0.11478 (14)0.70745 (10)0.0275 (4)
C130.07576 (18)0.19428 (14)0.67204 (9)0.0260 (4)
H13A0.00640.18010.64930.031*
H13B0.05630.24040.70050.031*
C140.43785 (17)0.26775 (12)0.60913 (9)0.0224 (4)
C150.54134 (19)0.28625 (14)0.58218 (10)0.0292 (5)
H150.55280.27140.54160.035*
C160.62767 (19)0.32579 (14)0.61342 (11)0.0312 (5)
H160.69830.33720.59480.037*
C170.60967 (19)0.34837 (13)0.67203 (10)0.0286 (5)
C180.50635 (19)0.33552 (14)0.69931 (10)0.0295 (5)
H180.49380.35420.73910.035*
C190.42111 (18)0.29471 (14)0.66760 (9)0.0274 (4)
H190.34990.28500.68620.033*
C200.1557 (2)0.49348 (17)0.42604 (11)0.0398 (6)
H20A0.09270.46020.40960.060*
H20B0.20380.51390.39340.060*
H20C0.12590.54250.44830.060*
C210.3212 (2)0.49031 (16)0.49552 (11)0.0362 (5)
H21A0.37320.50920.46410.054*
H21B0.36250.45540.52450.054*
H21C0.28890.54030.51560.054*
C220.0090 (2)0.07263 (17)0.73503 (13)0.0422 (6)
H22A0.03230.02250.75820.063*
H22B0.04300.05480.70330.063*
H22C0.02930.11350.76130.063*
C230.1941 (2)0.14062 (15)0.75762 (11)0.0339 (5)
H23A0.21890.08940.77910.051*
H23B0.15500.17920.78520.051*
H23C0.26010.16980.74070.051*
H2A0.081 (2)0.4117 (18)0.6308 (11)0.030 (7)*
H2B0.003 (2)0.3483 (17)0.6061 (12)0.036 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.04422 (17)0.04021 (16)0.04341 (16)0.01503 (11)0.01730 (11)0.00430 (11)
O10.0385 (9)0.0483 (10)0.0283 (8)0.0104 (8)0.0087 (7)0.0034 (7)
O20.0363 (9)0.0266 (8)0.0372 (9)0.0095 (7)0.0000 (7)0.0029 (7)
N10.0201 (8)0.0215 (8)0.0222 (8)0.0033 (6)0.0018 (6)0.0008 (6)
N20.0248 (9)0.0233 (9)0.0276 (9)0.0057 (7)0.0025 (7)0.0016 (7)
C10.0223 (9)0.0223 (9)0.0197 (9)0.0030 (8)0.0014 (7)0.0005 (8)
C20.0235 (10)0.0239 (10)0.0207 (9)0.0010 (8)0.0000 (7)0.0016 (8)
C30.0220 (9)0.0249 (10)0.0222 (9)0.0031 (8)0.0013 (7)0.0035 (8)
C40.0222 (9)0.0216 (9)0.0212 (9)0.0010 (8)0.0014 (7)0.0008 (8)
C50.0226 (9)0.0210 (9)0.0209 (9)0.0007 (7)0.0013 (7)0.0011 (7)
C60.0289 (11)0.0318 (11)0.0239 (10)0.0024 (9)0.0014 (8)0.0042 (9)
C70.0335 (12)0.0353 (12)0.0213 (10)0.0028 (9)0.0021 (8)0.0011 (9)
C80.0309 (11)0.0284 (11)0.0226 (10)0.0018 (9)0.0011 (8)0.0044 (8)
C90.0259 (10)0.0251 (10)0.0237 (10)0.0007 (8)0.0009 (8)0.0022 (8)
C100.0298 (11)0.0230 (10)0.0220 (10)0.0020 (8)0.0040 (8)0.0034 (8)
C110.0389 (12)0.0221 (10)0.0306 (11)0.0009 (9)0.0018 (9)0.0016 (9)
C120.0293 (11)0.0251 (10)0.0279 (11)0.0012 (8)0.0043 (8)0.0052 (8)
C130.0229 (10)0.0284 (10)0.0265 (10)0.0004 (8)0.0017 (8)0.0029 (8)
C140.0221 (9)0.0205 (9)0.0245 (10)0.0026 (7)0.0007 (7)0.0003 (8)
C150.0279 (11)0.0311 (11)0.0287 (11)0.0009 (9)0.0023 (9)0.0038 (9)
C160.0248 (10)0.0305 (11)0.0383 (12)0.0034 (9)0.0015 (9)0.0004 (9)
C170.0315 (11)0.0216 (10)0.0328 (11)0.0037 (8)0.0096 (9)0.0019 (8)
C180.0371 (12)0.0268 (10)0.0247 (10)0.0004 (9)0.0042 (9)0.0015 (9)
C190.0262 (10)0.0285 (10)0.0275 (10)0.0014 (8)0.0007 (8)0.0010 (9)
C200.0454 (14)0.0428 (14)0.0311 (12)0.0024 (11)0.0022 (10)0.0140 (11)
C210.0384 (13)0.0339 (12)0.0362 (13)0.0083 (10)0.0027 (10)0.0013 (10)
C220.0435 (14)0.0358 (13)0.0472 (15)0.0032 (11)0.0105 (12)0.0112 (11)
C230.0429 (13)0.0310 (11)0.0279 (11)0.0053 (10)0.0023 (10)0.0034 (9)
Geometric parameters (Å, º) top
Br1—C171.900 (2)C11—H11A0.9900
O1—C61.235 (3)C11—H11B0.9900
O2—C101.229 (3)C12—C221.527 (3)
N1—C11.392 (3)C12—C231.530 (3)
N1—C51.394 (3)C12—C131.540 (3)
N1—N21.422 (2)C13—H13A0.9900
N2—H2A0.90 (3)C13—H13B0.9900
N2—H2B0.89 (3)C14—C191.392 (3)
C1—C21.357 (3)C14—C151.394 (3)
C1—C91.505 (3)C15—C161.383 (3)
C2—C61.454 (3)C15—H150.9500
C2—C31.516 (3)C16—C171.378 (3)
C3—C41.499 (3)C16—H160.9500
C3—C141.528 (3)C17—C181.379 (3)
C3—H31.0000C18—C191.388 (3)
C4—C51.363 (3)C18—H180.9500
C4—C101.459 (3)C19—H190.9500
C5—C131.501 (3)C20—H20A0.9800
C6—C71.513 (3)C20—H20B0.9800
C7—C81.536 (3)C20—H20C0.9800
C7—H7A0.9900C21—H21A0.9800
C7—H7B0.9900C21—H21B0.9800
C8—C201.528 (3)C21—H21C0.9800
C8—C211.535 (3)C22—H22A0.9800
C8—C91.537 (3)C22—H22B0.9800
C9—H9A0.9900C22—H22C0.9800
C9—H9B0.9900C23—H23A0.9800
C10—C111.511 (3)C23—H23B0.9800
C11—C121.527 (3)C23—H23C0.9800
C1—N1—C5119.52 (16)C11—C12—C22110.16 (19)
C1—N1—N2121.76 (16)C11—C12—C23110.24 (19)
C5—N1—N2117.00 (16)C22—C12—C23108.6 (2)
N1—N2—H2A106.4 (17)C11—C12—C13108.65 (17)
N1—N2—H2B105.5 (17)C22—C12—C13109.01 (19)
H2A—N2—H2B115 (2)C23—C12—C13110.20 (18)
C2—C1—N1119.49 (18)C5—C13—C12113.89 (17)
C2—C1—C9122.82 (18)C5—C13—H13A108.8
N1—C1—C9117.66 (17)C12—C13—H13A108.8
C1—C2—C6120.98 (19)C5—C13—H13B108.8
C1—C2—C3119.60 (18)C12—C13—H13B108.8
C6—C2—C3119.41 (18)H13A—C13—H13B107.7
C4—C3—C2107.96 (16)C19—C14—C15118.06 (19)
C4—C3—C14113.98 (17)C19—C14—C3121.98 (18)
C2—C3—C14109.54 (16)C15—C14—C3119.93 (18)
C4—C3—H3108.4C16—C15—C14121.3 (2)
C2—C3—H3108.4C16—C15—H15119.4
C14—C3—H3108.4C14—C15—H15119.4
C5—C4—C10120.06 (19)C17—C16—C15119.0 (2)
C5—C4—C3120.38 (18)C17—C16—H16120.5
C10—C4—C3119.54 (18)C15—C16—H16120.5
C4—C5—N1119.06 (18)C16—C17—C18121.5 (2)
C4—C5—C13123.76 (18)C16—C17—Br1119.72 (17)
N1—C5—C13117.14 (17)C18—C17—Br1118.75 (17)
O1—C6—C2121.5 (2)C17—C18—C19118.7 (2)
O1—C6—C7120.5 (2)C17—C18—H18120.6
C2—C6—C7117.94 (19)C19—C18—H18120.6
C6—C7—C8113.62 (18)C18—C19—C14121.3 (2)
C6—C7—H7A108.8C18—C19—H19119.4
C8—C7—H7A108.8C14—C19—H19119.4
C6—C7—H7B108.8C8—C20—H20A109.5
C8—C7—H7B108.8C8—C20—H20B109.5
H7A—C7—H7B107.7H20A—C20—H20B109.5
C20—C8—C21109.38 (19)C8—C20—H20C109.5
C20—C8—C7109.91 (19)H20A—C20—H20C109.5
C21—C8—C7109.47 (19)H20B—C20—H20C109.5
C20—C8—C9108.16 (18)C8—C21—H21A109.5
C21—C8—C9110.86 (18)C8—C21—H21B109.5
C7—C8—C9109.04 (18)H21A—C21—H21B109.5
C1—C9—C8113.32 (17)C8—C21—H21C109.5
C1—C9—H9A108.9H21A—C21—H21C109.5
C8—C9—H9A108.9H21B—C21—H21C109.5
C1—C9—H9B108.9C12—C22—H22A109.5
C8—C9—H9B108.9C12—C22—H22B109.5
H9A—C9—H9B107.7H22A—C22—H22B109.5
O2—C10—C4121.4 (2)C12—C22—H22C109.5
O2—C10—C11121.47 (19)H22A—C22—H22C109.5
C4—C10—C11117.12 (18)H22B—C22—H22C109.5
C10—C11—C12112.89 (18)C12—C23—H23A109.5
C10—C11—H11A109.0C12—C23—H23B109.5
C12—C11—H11A109.0H23A—C23—H23B109.5
C10—C11—H11B109.0C12—C23—H23C109.5
C12—C11—H11B109.0H23A—C23—H23C109.5
H11A—C11—H11B107.8H23B—C23—H23C109.5
C5—N1—C1—C219.9 (3)C2—C1—C9—C818.2 (3)
N2—N1—C1—C2175.45 (18)N1—C1—C9—C8163.63 (17)
C5—N1—C1—C9158.28 (18)C20—C8—C9—C1166.50 (19)
N2—N1—C1—C96.3 (3)C21—C8—C9—C173.6 (2)
N1—C1—C2—C6169.81 (18)C7—C8—C9—C147.0 (2)
C9—C1—C2—C68.3 (3)C5—C4—C10—O2174.3 (2)
N1—C1—C2—C311.1 (3)C3—C4—C10—O23.9 (3)
C9—C1—C2—C3170.82 (18)C5—C4—C10—C118.0 (3)
C1—C2—C3—C435.9 (2)C3—C4—C10—C11173.81 (18)
C6—C2—C3—C4144.92 (19)O2—C10—C11—C12143.2 (2)
C1—C2—C3—C1488.7 (2)C4—C10—C11—C1239.0 (3)
C6—C2—C3—C1490.4 (2)C10—C11—C12—C22175.09 (19)
C2—C3—C4—C534.3 (2)C10—C11—C12—C2365.1 (2)
C14—C3—C4—C587.6 (2)C10—C11—C12—C1355.7 (2)
C2—C3—C4—C10147.44 (18)C4—C5—C13—C1215.5 (3)
C14—C3—C4—C1090.6 (2)N1—C5—C13—C12166.64 (18)
C10—C4—C5—N1173.91 (17)C11—C12—C13—C543.9 (2)
C3—C4—C5—N17.9 (3)C22—C12—C13—C5163.97 (19)
C10—C4—C5—C133.9 (3)C23—C12—C13—C577.0 (2)
C3—C4—C5—C13174.26 (18)C4—C3—C14—C1920.5 (3)
C1—N1—C5—C421.7 (3)C2—C3—C14—C19100.6 (2)
N2—N1—C5—C4172.97 (18)C4—C3—C14—C15161.37 (19)
C1—N1—C5—C13156.31 (18)C2—C3—C14—C1577.6 (2)
N2—N1—C5—C139.0 (3)C19—C14—C15—C163.7 (3)
C1—C2—C6—O1175.0 (2)C3—C14—C15—C16178.1 (2)
C3—C2—C6—O15.9 (3)C14—C15—C16—C171.1 (3)
C1—C2—C6—C72.9 (3)C15—C16—C17—C182.6 (3)
C3—C2—C6—C7176.25 (19)C15—C16—C17—Br1174.88 (17)
O1—C6—C7—C8153.4 (2)C16—C17—C18—C193.5 (3)
C2—C6—C7—C828.7 (3)Br1—C17—C18—C19174.04 (16)
C6—C7—C8—C20170.85 (19)C17—C18—C19—C140.7 (3)
C6—C7—C8—C2169.0 (2)C15—C14—C19—C182.8 (3)
C6—C7—C8—C952.4 (2)C3—C14—C19—C18179.03 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O2i0.90 (3)2.33 (3)3.220 (2)173 (2)
N2—H2B···O1ii0.89 (3)2.27 (3)3.046 (3)145 (2)
C20—H20B···Br1iii0.982.983.910 (2)159
C11—H11A···Br1iv0.992.843.797 (2)163
C9—H9A···O2i0.992.383.323 (3)160
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x1/2, y+1/2, z+1; (iii) x+1, y+1, z+1; (iv) x+1, y1/2, z+3/2.
 

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