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In the title compound, C33H25NO2, the azepine ring adopts a half-chair conformation. The mol­ecules are packed into a three-dimensional network by three intermolecular C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802000740/na6128sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802000740/na6128Isup2.hkl
Contains datablock I

CCDC reference: 180794

Key indicators

  • Single-crystal X-ray study
  • T = 183 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.060
  • wR factor = 0.151
  • Data-to-parameter ratio = 17.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

2,2,7-Triphenyl-1H-naphth[2,1-c]azepine-1,5-dione top
Crystal data top
C33H25NO2Dx = 1.283 Mg m3
Mr = 467.54Melting point: 538K K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.2788 (1) ÅCell parameters from 8192 reflections
b = 12.2856 (1) Åθ = 2.8–28.3°
c = 27.1499 (3) ŵ = 0.08 mm1
β = 94.313 (1)°T = 183 K
V = 2421.0 (1) Å3Block, colorless
Z = 40.50 × 0.30 × 0.30 mm
F(000) = 984
Data collection top
Siemens SMART CCD area-detector
diffractometer
5767 independent reflections
Radiation source: fine-focus sealed tube4083 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.075
Detector resolution: 8.33 pixels mm-1θmax = 28.3°, θmin = 2.8°
ω scansh = 99
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 1615
Tmin = 0.961, Tmax = 0.977l = 2936
14058 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.151 w = 1/[σ2(Fo2) + (0.0574P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max < 0.001
5767 reflectionsΔρmax = 0.47 e Å3
327 parametersΔρmin = 0.44 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.044 (3)
Special details top

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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
O10.77728 (17)0.56333 (9)0.24768 (4)0.0262 (3)
O20.44129 (16)0.45085 (9)0.38252 (4)0.0225 (3)
N10.74991 (18)0.38886 (10)0.27316 (5)0.0164 (3)
C10.7870 (2)0.49561 (12)0.28146 (6)0.0165 (3)
C20.8425 (2)0.53130 (12)0.33351 (5)0.0156 (3)
C30.7518 (2)0.49894 (12)0.37420 (6)0.0150 (3)
C40.5889 (2)0.42262 (12)0.36832 (5)0.0156 (3)
C50.6115 (2)0.30785 (12)0.34594 (6)0.0145 (3)
C60.7745 (2)0.30771 (12)0.31269 (6)0.0162 (3)
H6A0.88760.32300.33270.019*
H6B0.78580.23610.29820.019*
C70.6962 (2)0.35425 (14)0.22257 (6)0.0234 (4)
H7A0.68000.27670.22180.035*
H7B0.79080.37430.20150.035*
H7C0.58270.38910.21130.035*
C80.9813 (2)0.61269 (12)0.33858 (6)0.0177 (3)
H81.04210.63290.31110.021*
C91.0279 (2)0.66231 (12)0.38311 (6)0.0174 (3)
C100.9356 (2)0.63148 (12)0.42580 (6)0.0176 (3)
C110.9797 (2)0.68064 (14)0.47262 (6)0.0241 (4)
H111.06700.73600.47550.029*
C120.8953 (3)0.64749 (15)0.51344 (6)0.0282 (4)
H120.92410.68130.54370.034*
C130.7651 (2)0.56261 (15)0.50992 (6)0.0268 (4)
H130.71170.53880.53810.032*
C140.7168 (2)0.51489 (14)0.46526 (6)0.0214 (4)
H140.62890.45980.46340.026*
C150.7986 (2)0.54790 (12)0.42164 (6)0.0164 (3)
C161.1740 (2)0.74864 (12)0.38631 (6)0.0183 (3)
C171.1274 (2)0.85871 (13)0.38633 (6)0.0227 (4)
H171.00420.87920.38540.027*
C181.2639 (3)0.93825 (14)0.38766 (7)0.0281 (4)
H181.23121.01140.38720.034*
C191.4469 (3)0.90924 (15)0.38963 (6)0.0285 (4)
H191.53770.96260.39060.034*
C201.4951 (3)0.80008 (16)0.39017 (7)0.0319 (4)
H201.61880.78030.39170.038*
C211.3595 (2)0.71988 (14)0.38837 (7)0.0277 (4)
H211.39300.64680.38850.033*
C220.6510 (2)0.23185 (12)0.39111 (6)0.0179 (3)
C230.8084 (3)0.16773 (13)0.39762 (7)0.0253 (4)
H230.89500.16940.37410.030*
C240.8378 (3)0.10055 (15)0.43931 (7)0.0341 (5)
H240.94350.05800.44330.041*
C250.7095 (3)0.09754 (15)0.47449 (7)0.0370 (5)
H250.72920.05330.50220.044*
C260.5533 (3)0.16014 (15)0.46833 (7)0.0359 (5)
H260.46730.15820.49200.043*
C270.5227 (3)0.22652 (14)0.42700 (6)0.0267 (4)
H270.41560.26790.42310.032*
C280.4359 (2)0.27415 (12)0.31476 (6)0.0164 (3)
C290.3854 (2)0.16501 (13)0.31051 (6)0.0224 (4)
H290.45340.11300.32890.027*
C300.2353 (3)0.13236 (15)0.27935 (7)0.0293 (4)
H300.20140.05940.27800.035*
C310.1358 (2)0.20791 (16)0.25030 (7)0.0288 (4)
H310.03700.18580.22890.035*
C320.1853 (2)0.31693 (15)0.25354 (7)0.0280 (4)
H320.12090.36810.23380.034*
C330.3306 (2)0.34995 (14)0.28617 (6)0.0230 (4)
H330.35860.42360.28910.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0393 (8)0.0209 (6)0.0184 (6)0.0045 (5)0.0021 (5)0.0061 (5)
O20.0218 (6)0.0177 (6)0.0292 (7)0.0015 (5)0.0102 (5)0.0054 (5)
N10.0227 (7)0.0145 (6)0.0124 (6)0.0029 (5)0.0036 (5)0.0001 (5)
C10.0178 (8)0.0159 (7)0.0162 (8)0.0017 (6)0.0050 (6)0.0012 (6)
C20.0188 (8)0.0117 (7)0.0167 (8)0.0011 (6)0.0033 (6)0.0008 (6)
C30.0178 (8)0.0108 (7)0.0167 (8)0.0008 (6)0.0037 (6)0.0008 (5)
C40.0203 (8)0.0126 (7)0.0144 (8)0.0007 (6)0.0049 (6)0.0004 (6)
C50.0182 (8)0.0106 (7)0.0151 (7)0.0016 (6)0.0039 (6)0.0001 (5)
C60.0208 (8)0.0119 (7)0.0164 (8)0.0004 (6)0.0048 (6)0.0009 (6)
C70.0304 (10)0.0248 (9)0.0153 (8)0.0052 (7)0.0033 (7)0.0047 (6)
C80.0211 (8)0.0145 (7)0.0182 (8)0.0024 (6)0.0053 (6)0.0017 (6)
C90.0181 (8)0.0132 (7)0.0209 (8)0.0013 (6)0.0015 (6)0.0005 (6)
C100.0182 (8)0.0158 (8)0.0188 (8)0.0008 (6)0.0017 (6)0.0030 (6)
C110.0251 (9)0.0253 (9)0.0219 (9)0.0049 (7)0.0016 (7)0.0071 (7)
C120.0314 (10)0.0348 (10)0.0187 (9)0.0037 (8)0.0029 (7)0.0100 (7)
C130.0275 (10)0.0361 (10)0.0177 (9)0.0015 (8)0.0084 (7)0.0032 (7)
C140.0223 (9)0.0231 (8)0.0197 (8)0.0035 (7)0.0074 (7)0.0014 (6)
C150.0177 (8)0.0149 (7)0.0169 (8)0.0008 (6)0.0034 (6)0.0017 (6)
C160.0231 (8)0.0152 (8)0.0166 (8)0.0049 (6)0.0017 (6)0.0009 (6)
C170.0251 (9)0.0178 (8)0.0255 (9)0.0020 (7)0.0042 (7)0.0010 (6)
C180.0384 (11)0.0165 (8)0.0297 (10)0.0067 (7)0.0056 (8)0.0009 (7)
C190.0353 (10)0.0246 (9)0.0257 (10)0.0161 (8)0.0022 (8)0.0012 (7)
C200.0227 (9)0.0316 (10)0.0410 (12)0.0058 (8)0.0004 (8)0.0030 (8)
C210.0252 (10)0.0185 (8)0.0396 (11)0.0012 (7)0.0030 (8)0.0014 (7)
C220.0252 (9)0.0128 (7)0.0157 (8)0.0059 (6)0.0010 (6)0.0007 (6)
C230.0299 (10)0.0203 (8)0.0250 (9)0.0031 (7)0.0026 (7)0.0031 (7)
C240.0412 (12)0.0262 (10)0.0326 (11)0.0016 (8)0.0115 (9)0.0068 (8)
C250.0632 (14)0.0261 (10)0.0199 (10)0.0131 (10)0.0087 (9)0.0073 (7)
C260.0617 (14)0.0281 (10)0.0193 (10)0.0115 (10)0.0115 (9)0.0020 (7)
C270.0390 (11)0.0212 (9)0.0209 (9)0.0045 (7)0.0105 (8)0.0004 (7)
C280.0191 (8)0.0163 (8)0.0146 (8)0.0030 (6)0.0064 (6)0.0006 (6)
C290.0292 (10)0.0158 (8)0.0225 (9)0.0015 (7)0.0040 (7)0.0024 (6)
C300.0311 (10)0.0237 (9)0.0331 (10)0.0100 (7)0.0038 (8)0.0104 (7)
C310.0207 (9)0.0414 (11)0.0243 (10)0.0065 (8)0.0019 (7)0.0092 (8)
C320.0206 (9)0.0363 (10)0.0269 (10)0.0004 (8)0.0008 (7)0.0052 (8)
C330.0205 (9)0.0208 (8)0.0277 (9)0.0027 (7)0.0023 (7)0.0027 (7)
Geometric parameters (Å, º) top
O1—C11.236 (2)C16—C211.392 (2)
O2—C41.219 (2)C16—C171.394 (2)
N1—C11.354 (2)C17—C181.392 (2)
N1—C71.463 (2)C17—H170.9300
N1—C61.466 (2)C18—C191.376 (3)
C1—C21.505 (2)C18—H180.9300
C2—C31.387 (2)C19—C201.386 (3)
C2—C81.421 (2)C19—H190.9300
C3—C151.439 (2)C20—C211.393 (2)
C3—C41.510 (2)C20—H200.9300
C4—C51.549 (2)C21—H210.9300
C5—C281.535 (2)C22—C231.391 (2)
C5—C61.544 (2)C22—C271.401 (2)
C5—C221.551 (2)C23—C241.404 (2)
C6—H6A0.9700C23—H230.9300
C6—H6B0.9700C24—C251.385 (3)
C7—H7A0.9600C24—H240.9300
C7—H7B0.9600C25—C261.372 (3)
C7—H7C0.9600C25—H250.9300
C8—C91.374 (2)C26—C271.391 (3)
C8—H80.9300C26—H260.9300
C9—C101.434 (2)C27—H270.9300
C9—C161.500 (2)C28—C291.393 (2)
C10—C111.422 (2)C28—C331.403 (2)
C10—C151.430 (2)C29—C301.390 (2)
C11—C121.369 (2)C29—H290.9300
C11—H110.9300C30—C311.386 (3)
C12—C131.407 (2)C30—H300.9300
C12—H120.9300C31—C321.388 (3)
C13—C141.369 (2)C31—H310.9300
C13—H130.9300C32—C331.388 (2)
C14—C151.424 (2)C32—H320.9300
C14—H140.9300C33—H330.9300
C1—N1—C7118.26 (13)C10—C15—C3119.19 (13)
C1—N1—C6121.66 (13)C21—C16—C17118.78 (15)
C7—N1—C6119.94 (13)C21—C16—C9120.25 (14)
O1—C1—N1121.91 (14)C17—C16—C9120.96 (15)
O1—C1—C2119.78 (14)C18—C17—C16120.51 (16)
N1—C1—C2118.31 (13)C18—C17—H17119.7
C3—C2—C8120.14 (14)C16—C17—H17119.7
C3—C2—C1123.64 (14)C19—C18—C17120.40 (17)
C8—C2—C1115.76 (13)C19—C18—H18119.8
C2—C3—C15119.88 (14)C17—C18—H18119.8
C2—C3—C4120.69 (14)C18—C19—C20119.66 (16)
C15—C3—C4119.03 (13)C18—C19—H19120.2
O2—C4—C3119.57 (13)C20—C19—H19120.2
O2—C4—C5120.33 (14)C19—C20—C21120.37 (17)
C3—C4—C5120.07 (12)C19—C20—H20119.8
C28—C5—C6108.76 (12)C21—C20—H20119.8
C28—C5—C4110.70 (12)C16—C21—C20120.28 (16)
C6—C5—C4109.82 (12)C16—C21—H21119.9
C28—C5—C22111.76 (12)C20—C21—H21119.9
C6—C5—C22110.89 (13)C23—C22—C27118.11 (15)
C4—C5—C22104.87 (12)C23—C22—C5122.93 (14)
N1—C6—C5111.74 (12)C27—C22—C5118.97 (15)
N1—C6—H6A109.3C22—C23—C24120.62 (18)
C5—C6—H6A109.3C22—C23—H23119.7
N1—C6—H6B109.3C24—C23—H23119.7
C5—C6—H6B109.3C25—C24—C23120.12 (19)
H6A—C6—H6B107.9C25—C24—H24119.9
N1—C7—H7A109.5C23—C24—H24119.9
N1—C7—H7B109.5C26—C25—C24119.73 (17)
H7A—C7—H7B109.5C26—C25—H25120.1
N1—C7—H7C109.5C24—C25—H25120.1
H7A—C7—H7C109.5C25—C26—C27120.52 (18)
H7B—C7—H7C109.5C25—C26—H26119.7
C9—C8—C2121.63 (14)C27—C26—H26119.7
C9—C8—H8119.2C26—C27—C22120.89 (18)
C2—C8—H8119.2C26—C27—H27119.6
C8—C9—C10119.63 (14)C22—C27—H27119.6
C8—C9—C16119.47 (14)C29—C28—C33117.59 (15)
C10—C9—C16120.90 (14)C29—C28—C5120.59 (14)
C11—C10—C15119.00 (14)C33—C28—C5121.57 (14)
C11—C10—C9121.48 (15)C30—C29—C28121.27 (16)
C15—C10—C9119.51 (14)C30—C29—H29119.4
C12—C11—C10120.82 (16)C28—C29—H29119.4
C12—C11—H11119.6C31—C30—C29120.41 (17)
C10—C11—H11119.6C31—C30—H30119.8
C11—C12—C13120.42 (16)C29—C30—H30119.8
C11—C12—H12119.8C30—C31—C32119.19 (17)
C13—C12—H12119.8C30—C31—H31120.4
C14—C13—C12120.28 (16)C32—C31—H31120.4
C14—C13—H13119.9C33—C32—C31120.29 (17)
C12—C13—H13119.9C33—C32—H32119.9
C13—C14—C15121.29 (16)C31—C32—H32119.9
C13—C14—H14119.4C32—C33—C28121.17 (16)
C15—C14—H14119.4C32—C33—H33119.4
C14—C15—C10118.13 (14)C28—C33—H33119.4
C14—C15—C3122.67 (14)
C7—N1—C1—O10.3 (2)C9—C10—C15—C32.1 (2)
C6—N1—C1—O1175.51 (14)C2—C3—C15—C14177.05 (15)
C7—N1—C1—C2179.92 (14)C4—C3—C15—C1410.1 (2)
C6—N1—C1—C24.1 (2)C2—C3—C15—C101.5 (2)
O1—C1—C2—C3134.29 (17)C4—C3—C15—C10171.33 (14)
N1—C1—C2—C346.1 (2)C8—C9—C16—C2178.5 (2)
O1—C1—C2—C837.9 (2)C10—C9—C16—C21101.97 (19)
N1—C1—C2—C8141.75 (15)C8—C9—C16—C17100.32 (18)
C8—C2—C3—C150.0 (2)C10—C9—C16—C1779.3 (2)
C1—C2—C3—C15171.89 (14)C21—C16—C17—C180.9 (2)
C8—C2—C3—C4172.66 (14)C9—C16—C17—C18177.87 (15)
C1—C2—C3—C40.8 (2)C16—C17—C18—C190.8 (3)
C2—C3—C4—O2122.52 (17)C17—C18—C19—C200.1 (3)
C15—C3—C4—O250.2 (2)C18—C19—C20—C210.5 (3)
C2—C3—C4—C559.5 (2)C17—C16—C21—C200.3 (3)
C15—C3—C4—C5127.78 (15)C9—C16—C21—C20178.49 (16)
O2—C4—C5—C2837.08 (19)C19—C20—C21—C160.4 (3)
C3—C4—C5—C28144.92 (14)C28—C5—C22—C23117.43 (16)
O2—C4—C5—C6157.19 (14)C6—C5—C22—C234.1 (2)
C3—C4—C5—C624.80 (19)C4—C5—C22—C23122.58 (16)
O2—C4—C5—C2283.62 (17)C28—C5—C22—C2762.17 (18)
C3—C4—C5—C2294.39 (16)C6—C5—C22—C27176.29 (14)
C1—N1—C6—C579.76 (18)C4—C5—C22—C2757.82 (18)
C7—N1—C6—C5104.51 (16)C27—C22—C23—C240.6 (2)
C28—C5—C6—N163.67 (16)C5—C22—C23—C24179.79 (15)
C4—C5—C6—N157.61 (16)C22—C23—C24—C250.0 (3)
C22—C5—C6—N1173.04 (12)C23—C24—C25—C260.3 (3)
C3—C2—C8—C90.9 (2)C24—C25—C26—C270.1 (3)
C1—C2—C8—C9171.60 (14)C25—C26—C27—C220.7 (3)
C2—C8—C9—C100.3 (2)C23—C22—C27—C260.9 (3)
C2—C8—C9—C16179.31 (14)C5—C22—C27—C26179.45 (16)
C8—C9—C10—C11179.93 (15)C6—C5—C28—C2989.77 (16)
C16—C9—C10—C110.5 (2)C4—C5—C28—C29149.49 (14)
C8—C9—C10—C151.2 (2)C22—C5—C28—C2932.99 (19)
C16—C9—C10—C15179.21 (14)C6—C5—C28—C3384.37 (17)
C15—C10—C11—C121.2 (3)C4—C5—C28—C3336.37 (19)
C9—C10—C11—C12177.52 (16)C22—C5—C28—C33152.87 (14)
C10—C11—C12—C131.1 (3)C33—C28—C29—C300.4 (2)
C11—C12—C13—C142.3 (3)C5—C28—C29—C30174.81 (15)
C12—C13—C14—C151.2 (3)C28—C29—C30—C312.3 (3)
C13—C14—C15—C101.0 (2)C29—C30—C31—C321.4 (3)
C13—C14—C15—C3179.59 (16)C30—C31—C32—C331.2 (3)
C11—C10—C15—C142.2 (2)C31—C32—C33—C283.1 (3)
C9—C10—C15—C14176.53 (14)C29—C28—C33—C322.2 (2)
C11—C10—C15—C3179.17 (14)C5—C28—C33—C32172.10 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6B···O1i0.972.493.428 (2)164
C13—H13···O2ii0.932.503.387 (2)159
C21—H21···O2iii0.932.443.364 (2)172
Symmetry codes: (i) x+3/2, y1/2, z+1/2; (ii) x+1, y+1, z+1; (iii) x+1, y, z.
 

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