7-Phenyl-5H-dibenz­[c,e]­azepine N-oxide

Gould, R.O.; Krieger, M.; Sharp, J.T.

doi:10.1107/S1600536801008042

7-Phenyl-5H-dibenz[c,e]azepine N-oxide

The structure of the title compound, C₂₀H₁₅NO, has been determined as part of a study of the preparation of 5-substituted dibenz[c,e]azepines. The geometry of this important precursor shows a conformation favouring attack by incoming reagents.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801008042/na6075sup1.cif Contains datablock qwikie
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801008042/na6075Isup2.hkl Contains datablock I

CCDC reference: 170302

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Key indicators

Single-crystal X-ray study
T = 220 K
Mean (C-C) = 0.002 Å
R factor = 0.040
wR factor = 0.108
Data-to-parameter ratio = 10.9

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No syntax errors found



ADDSYM reports no extra symmetry


 Alert Level C:



ABSTY_02  Alert C An _exptl_absorpt_correction_type has been given without
          a literature citation. This should be contained in the
          _exptl_absorpt_process_details field.
          Absorption correction given as analytical


 0 Alert Level A = Potentially serious problem

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 1 Alert Level C = Please check

Computing details top

Data collection: DIF4 (Stoe & Cie, 1990); cell refinement: DIF4; data reduction: REDU4 (Stoe & Cie, 1990); 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.

7-phenyl-5H-dibenz[c,e]azepine N-oxide top

Crystal data top

C₂₀H₁₅NO	D_x = 1.282 Mg m⁻³
M_r = 285.33	Melting point: 176 K
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54180 Å
a = 11.2060 (17) Å	Cell parameters from 28 reflections
b = 9.3052 (10) Å	θ = 39–42°
c = 14.4925 (18) Å	µ = 0.62 mm⁻¹
β = 101.979 (8)°	T = 220 K
V = 1478.3 (3) Å³	Prism, colourless
Z = 4	0.70 × 0.42 × 0.23 mm
F(000) = 600

Data collection top

Stoe Stadi-4 diffractometer	2349 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.009
Graphite monochromator	θ_max = 69.9°, θ_min = 4.6°
θ–ω scans	h = −13→12
Absorption correction: analytical	k = −5→11
T_min = 0.659, T_max = 0.865	l = −16→17
3787 measured reflections	3 standard reflections every 120 min
2666 independent reflections	intensity decay: 0.0%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.108	w = 1/[σ²(F_o²) + (0.0578P)² + 0.4324P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.017
2666 reflections	Δρ_max = 0.21 e Å⁻³
245 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0040 (5)

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

	x	y	z	U_iso*/U_eq
O1	0.30052 (9)	0.04541 (10)	0.67275 (8)	0.0415 (3)
N1	0.30875 (10)	−0.09313 (12)	0.66734 (8)	0.0313 (3)
C2	0.40378 (12)	−0.16189 (14)	0.64955 (9)	0.0306 (3)
C3	0.40271 (12)	−0.32068 (15)	0.64083 (9)	0.0318 (3)
C4	0.30567 (12)	−0.40209 (15)	0.58800 (9)	0.0320 (3)
C5	0.18789 (12)	−0.33850 (14)	0.54084 (10)	0.0325 (3)
C6	0.13366 (12)	−0.23002 (14)	0.58494 (10)	0.0327 (3)
C7	0.19872 (13)	−0.17551 (16)	0.67904 (10)	0.0350 (3)
H7A	0.1499 (15)	−0.1042 (18)	0.7052 (11)	0.042*
H7B	0.2276 (15)	−0.2579 (18)	0.7248 (12)	0.042*
C31	0.50959 (14)	−0.39244 (17)	0.68383 (11)	0.0397 (4)
H31	0.5787 (16)	−0.3366 (19)	0.7187 (12)	0.048*
C32	0.52282 (16)	−0.53871 (17)	0.67601 (12)	0.0447 (4)
H32	0.6030 (17)	−0.585 (2)	0.7086 (13)	0.054*
C33	0.42796 (15)	−0.61890 (17)	0.62388 (11)	0.0426 (4)
H33	0.4342 (16)	−0.723 (2)	0.6199 (12)	0.051*
C34	0.32211 (15)	−0.55089 (15)	0.58056 (11)	0.0379 (3)
H34	0.2536 (16)	−0.6098 (19)	0.5455 (12)	0.046*
C51	0.12622 (14)	−0.38864 (16)	0.45249 (11)	0.0400 (4)
H51	0.1654 (16)	−0.4653 (19)	0.4215 (12)	0.048*
C52	0.01447 (15)	−0.33123 (18)	0.40979 (12)	0.0457 (4)
H52	−0.0290 (16)	−0.368 (2)	0.3493 (14)	0.055*
C53	−0.03815 (15)	−0.22316 (18)	0.45302 (13)	0.0462 (4)
H53	−0.1208 (17)	−0.181 (2)	0.4210 (13)	0.055*
C54	0.02103 (14)	−0.17327 (17)	0.54080 (12)	0.0408 (4)
H54	−0.0157 (15)	−0.098 (2)	0.5752 (12)	0.049*
C1P	0.51519 (12)	−0.08273 (15)	0.64027 (10)	0.0330 (3)
C2P	0.57889 (14)	−0.1287 (2)	0.57257 (12)	0.0456 (4)
H2P	0.5457 (17)	−0.211 (2)	0.5318 (13)	0.055*
C3P	0.68383 (16)	−0.0593 (2)	0.56069 (13)	0.0542 (5)
H3P	0.7269 (18)	−0.098 (2)	0.5100 (14)	0.065*
C4P	0.72907 (16)	0.0542 (2)	0.61841 (15)	0.0545 (5)
H4P	0.8075 (18)	0.103 (2)	0.6090 (14)	0.065*
C5P	0.66815 (15)	0.09973 (18)	0.68706 (15)	0.0507 (4)
H5P	0.6986 (18)	0.179 (2)	0.7287 (14)	0.061*
C6P	0.56116 (14)	0.03295 (15)	0.69785 (12)	0.0395 (4)
H6P	0.5150 (16)	0.0694 (19)	0.7445 (13)	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0423 (6)	0.0273 (5)	0.0558 (7)	0.0024 (4)	0.0123 (5)	−0.0081 (4)
N1	0.0332 (6)	0.0272 (6)	0.0336 (6)	0.0001 (5)	0.0072 (5)	−0.0036 (4)
C2	0.0301 (7)	0.0299 (7)	0.0311 (7)	−0.0001 (5)	0.0052 (5)	−0.0018 (5)
C3	0.0332 (8)	0.0294 (7)	0.0337 (7)	0.0012 (5)	0.0089 (6)	−0.0020 (5)
C4	0.0341 (8)	0.0302 (7)	0.0328 (7)	−0.0005 (5)	0.0095 (6)	−0.0006 (5)
C5	0.0313 (7)	0.0289 (7)	0.0369 (7)	−0.0040 (5)	0.0066 (6)	0.0022 (5)
C6	0.0284 (7)	0.0311 (7)	0.0391 (7)	−0.0028 (5)	0.0084 (6)	0.0029 (6)
C7	0.0324 (8)	0.0357 (7)	0.0395 (8)	−0.0002 (6)	0.0136 (6)	−0.0019 (6)
C31	0.0338 (8)	0.0370 (8)	0.0464 (8)	0.0040 (6)	0.0037 (7)	−0.0029 (6)
C32	0.0438 (9)	0.0385 (8)	0.0504 (9)	0.0120 (7)	0.0065 (7)	0.0000 (7)
C33	0.0540 (10)	0.0302 (8)	0.0446 (8)	0.0070 (7)	0.0125 (7)	−0.0022 (6)
C34	0.0440 (9)	0.0296 (7)	0.0403 (8)	−0.0016 (6)	0.0090 (7)	−0.0029 (6)
C51	0.0414 (8)	0.0364 (8)	0.0406 (8)	−0.0047 (6)	0.0051 (7)	−0.0027 (6)
C52	0.0419 (9)	0.0468 (9)	0.0432 (9)	−0.0073 (7)	−0.0028 (7)	0.0019 (7)
C53	0.0320 (8)	0.0437 (9)	0.0590 (10)	−0.0031 (7)	0.0003 (7)	0.0083 (7)
C54	0.0313 (8)	0.0368 (8)	0.0546 (9)	−0.0009 (6)	0.0097 (7)	0.0024 (7)
C1P	0.0301 (7)	0.0315 (7)	0.0359 (7)	0.0014 (5)	0.0035 (6)	0.0043 (5)
C2P	0.0360 (8)	0.0585 (10)	0.0432 (9)	−0.0034 (7)	0.0101 (7)	−0.0035 (8)
C3P	0.0400 (9)	0.0734 (12)	0.0518 (10)	−0.0031 (8)	0.0156 (8)	0.0088 (9)
C4P	0.0322 (9)	0.0557 (11)	0.0743 (12)	−0.0038 (7)	0.0079 (8)	0.0230 (9)
C5P	0.0358 (9)	0.0330 (8)	0.0775 (12)	−0.0022 (7)	−0.0014 (8)	0.0036 (8)
C6P	0.0331 (8)	0.0297 (7)	0.0527 (9)	0.0015 (6)	0.0024 (7)	0.0010 (6)

Geometric parameters (Å, º) top

N1—C2	1.3130 (17)	C33—H33	0.976 (19)
C2—C3	1.4828 (19)	C34—H34	0.993 (18)
C3—C4	1.4132 (19)	C51—C52	1.384 (2)
C4—C5	1.4781 (19)	C51—H51	0.992 (18)
C5—C6	1.3992 (19)	C52—C53	1.380 (2)
C6—C7	1.495 (2)	C52—H52	0.973 (19)
N1—C7	1.4911 (17)	C53—C54	1.387 (2)
O1—N1	1.2960 (14)	C53—H53	1.025 (19)
C2—C1P	1.4796 (19)	C54—H54	0.998 (18)
C3—C31	1.400 (2)	C1P—C6P	1.393 (2)
C4—C34	1.4038 (19)	C1P—C2P	1.395 (2)
C5—C51	1.403 (2)	C2P—C3P	1.383 (2)
C6—C54	1.395 (2)	C2P—H2P	0.99 (2)
C7—H7A	0.985 (17)	C3P—C4P	1.377 (3)
C7—H7B	1.021 (17)	C3P—H3P	1.02 (2)
C31—C32	1.376 (2)	C4P—C5P	1.385 (3)
C31—H31	0.981 (18)	C4P—H4P	1.02 (2)
C32—C33	1.387 (2)	C5P—C6P	1.388 (2)
C32—H32	1.018 (19)	C5P—H5P	0.97 (2)
C33—C34	1.376 (2)	C6P—H6P	0.993 (18)

C7—N1—C2	119.69 (11)	C33—C34—C4	122.22 (14)
N1—C2—C3	120.65 (12)	C33—C34—H34	118.8 (10)
C2—C3—C4	124.89 (12)	C4—C34—H34	119.0 (10)
C3—C4—C5	123.28 (12)	C52—C51—C5	120.56 (15)
C4—C5—C6	120.56 (13)	C52—C51—H51	121.3 (10)
C5—C6—C7	119.05 (13)	C5—C51—H51	118.1 (10)
C6—C7—N1	109.20 (11)	C53—C52—C51	120.70 (15)
O1—N1—C7	115.70 (11)	C53—C52—H52	119.0 (11)
O1—N1—C2	124.57 (11)	C51—C52—H52	120.3 (11)
C1P—C2—N1	120.62 (12)	C52—C53—C54	119.49 (15)
C1P—C2—C3	118.71 (11)	C52—C53—H53	120.4 (11)
C31—C3—C2	116.51 (13)	C54—C53—H53	120.1 (11)
C31—C3—C4	118.47 (13)	C53—C54—C6	120.58 (15)
C34—C4—C3	118.15 (13)	C53—C54—H54	121.7 (10)
C34—C4—C5	118.57 (13)	C6—C54—H54	117.7 (10)
C51—C5—C4	120.82 (13)	C6P—C1P—C2P	118.58 (14)
C51—C5—C6	118.59 (13)	C6P—C1P—C2	122.97 (13)
C54—C6—C5	120.07 (14)	C2P—C1P—C2	118.42 (13)
C54—C6—C7	120.88 (13)	C3P—C2P—C1P	121.13 (17)
N1—C7—H7A	103.7 (10)	C3P—C2P—H2P	120.7 (11)
C6—C7—H7A	112.0 (10)	C1P—C2P—H2P	118.2 (11)
N1—C7—H7B	107.6 (9)	C4P—C3P—C2P	119.85 (17)
C6—C7—H7B	111.5 (9)	C4P—C3P—H3P	122.4 (11)
H7A—C7—H7B	112.5 (13)	C2P—C3P—H3P	117.7 (12)
C32—C31—C3	122.14 (15)	C3P—C4P—C5P	119.79 (16)
C32—C31—H31	118.6 (10)	C3P—C4P—H4P	118.4 (11)
C3—C31—H31	119.2 (10)	C5P—C4P—H4P	121.8 (12)
C31—C32—C33	119.55 (15)	C4P—C5P—C6P	120.68 (17)
C31—C32—H32	118.5 (11)	C4P—C5P—H5P	121.2 (12)
C33—C32—H32	122.0 (11)	C6P—C5P—H5P	118.1 (12)
C34—C33—C32	119.46 (14)	C5P—C6P—C1P	119.93 (16)
C34—C33—H33	119.8 (11)	C5P—C6P—H6P	120.6 (10)
C32—C33—H33	120.7 (11)	C1P—C6P—H6P	119.5 (10)

C7—N1—C2—C3	0.08 (19)	C2—C3—C31—C32	−175.99 (14)
N1—C2—C3—C4	46.2 (2)	C3—C31—C32—C33	0.1 (2)
C2—C3—C4—C5	−5.3 (2)	C31—C32—C33—C34	0.2 (2)
C3—C4—C5—C6	−39.58 (19)	C32—C33—C34—C4	−0.7 (2)
C4—C5—C6—C7	2.18 (19)	C3—C4—C34—C33	1.0 (2)
C5—C6—C7—N1	69.55 (16)	C5—C4—C34—C33	−178.67 (14)
C6—C7—N1—C2	−72.58 (16)	C6—C5—C51—C52	0.4 (2)
O1—N1—C2—C1P	4.2 (2)	C4—C5—C51—C52	178.32 (13)
C7—N1—C2—C1P	−178.31 (12)	C5—C51—C52—C53	0.3 (2)
O1—N1—C2—C3	−177.45 (12)	C51—C52—C53—C54	−0.9 (2)
N1—C2—C3—C31	−137.92 (14)	C52—C53—C54—C6	0.9 (2)
C1P—C2—C3—C31	40.50 (18)	C5—C6—C54—C53	−0.2 (2)
C1P—C2—C3—C4	−135.36 (14)	C7—C6—C54—C53	179.24 (14)
C31—C3—C4—C34	−0.68 (19)	N1—C2—C1P—C6P	39.5 (2)
C2—C3—C4—C34	175.11 (13)	C3—C2—C1P—C6P	−138.93 (14)
C31—C3—C4—C5	178.96 (13)	N1—C2—C1P—C2P	−142.37 (14)
C34—C4—C5—C6	140.06 (14)	C3—C2—C1P—C2P	39.20 (19)
C34—C4—C5—C51	−37.85 (19)	C6P—C1P—C2P—C3P	−1.6 (2)
C3—C4—C5—C51	142.51 (14)	C2—C1P—C2P—C3P	−179.83 (15)
C51—C5—C6—C54	−0.5 (2)	C1P—C2P—C3P—C4P	2.1 (3)
C4—C5—C6—C54	−178.40 (12)	C2P—C3P—C4P—C5P	−1.0 (3)
C51—C5—C6—C7	−179.86 (12)	C3P—C4P—C5P—C6P	−0.6 (3)
O1—N1—C7—C6	105.17 (13)	C4P—C5P—C6P—C1P	1.1 (2)
C54—C6—C7—N1	−109.86 (14)	C2P—C1P—C6P—C5P	0.0 (2)
C4—C3—C31—C32	0.1 (2)	C2—C1P—C6P—C5P	178.14 (14)

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7-Phenyl-5H-dibenz­[c,e]­azepine N-oxide

Supporting information

Key indicators

checkCIF results

7-Phenyl-5H-dibenz[c,e]azepine N-oxide