5,5'-(Piperazine-1,4-di­yl)bis­(8-chloro­pyrido[2,3-b][1,5]benzoxazepine)

The centrosymmetric title compound, C₂₈H₂₀Cl₂N₆O₂, features a tricyclic framework with the characteristic V-shape of the pyridobenzoxazepine nucleus and with the central seven-membered heterocycle having a classical boat conformation. The piperazine ring displays an almost-perfect chair conformation, with the tricyclic nuclei assuming a pseudo-equatorial orientation.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.040
• wR factor = 0.104
• Data-to-parameter ratio = 16.6

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Author Response: The work described in this contribution is part of a multi-disciplinary research program. The synthesis and characteristaion of compound was performed by Amelia Vom under the combined supervision of Ben Capuano, Edward J. Lloyd, Ian Crosby and Elizabeth Yuriev. The crystallographic analysis was performed by Craig M. Forsyth.

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Computing details

Data collection: COLLECT (Bruker, 2004); cell refinement: HKL-2000 (Bruker, 2004); data reduction: HKL-2000; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001) and POV-RAY (Cason, 2003); software used to prepare material for publication: SHELXL97.

5,5'-(Piperazine-1,4-diyl)bis(8-chloropyrido[2,3-b][1,5]benzoxazepine)

Crystal data

C28H20Cl2N6O2	F(000) = 560
Mr = 543.40	Dx = 1.451 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 13486 reflections
a = 8.6940 (2) Å	θ = 2.4–27.5°
b = 8.9993 (2) Å	µ = 0.30 mm^−1
c = 16.2542 (4) Å	T = 123 K
β = 102.089 (1)°	Prismatic, pale yellow
V = 1243.52 (5) Å^3	0.20 × 0.10 × 0.10 mm
Z = 2

Data collection

Enraf–Nonius KappaCCD area-detector diffractometer	2860 independent reflections
Radiation source: fine-focus sealed tube	2080 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
1° frames in φ and ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SORTAV; Blessing 1997)	h = −11→11
Tmin = 0.932, Tmax = 0.971	k = −11→10
13846 measured reflections	l = −21→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0512P)^2 + 0.2669P] where P = (Fo^2 + 2Fc^2)/3
2860 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

Experimental. Spectroscopic analysis: IR (Medium?, ν_max, cm^-1): 1599, 1586, 1549; ¹H NMR (300 MHz, CDCl₃, δ, p.p.m.): 3.66 (8H, br s, H2', H3', H5', H6'), 6.99 (2H, δ, J = 8.5 Hz, H9, H9''), 7.17–7.28 (6H, m, H3, H7, H10, H3'', H7'', H10''), 7.77 (2H, d, J = 7.5 Hz, H4, H4''), 8.45 (2H, br s, H2, H2''); ¹³C NMR (75.5 MHz, CDCl₃, δ, p.p.m.): 47.4 (CH₂), 117.4 (C_q), 121.9 (CH), 122.4 (CH), 125.0 (CH), 126.7 (CH), 131.1 (C_q), 139.7 (CH), 140.1 (C_q), 148.5 (C_q), 151.9 (CH), 158.2 (C_q), 164.2 (C_q); ESI MS (70 V): m/z 545 (M[³⁷Cl]H⁺, 34%), 543 (M[³⁵Cl]H⁺, 100), 274 (26), 272 (80). ESI high-resolution MS, found: m/z 543.1088, calculated for C₂₈H₂₀Cl₂N₆O₂: m/z 543.1098.

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.49521 (6)	0.71604 (5)	0.02155 (3)	0.03145 (16)
O1	0.99081 (14)	1.13592 (13)	0.17585 (7)	0.0217 (3)
N1	1.25115 (18)	1.08117 (17)	0.18770 (9)	0.0248 (4)
N2	0.83072 (17)	0.95762 (15)	0.28097 (8)	0.0189 (3)
N3	0.99236 (17)	0.97728 (16)	0.41237 (8)	0.0187 (3)
C1	0.6392 (2)	0.8438 (2)	0.06698 (11)	0.0224 (4)
C2	0.7095 (2)	0.9313 (2)	0.01586 (11)	0.0252 (4)
H2	0.6777	0.9260	−0.0437	0.030*
C3	0.8281 (2)	1.0276 (2)	0.05378 (11)	0.0239 (4)
H3	0.8784	1.0894	0.0200	0.029*
C4	0.8735 (2)	1.03400 (19)	0.14064 (10)	0.0201 (4)
C5	0.8019 (2)	0.94623 (19)	0.19280 (10)	0.0185 (4)
C6	0.6819 (2)	0.84989 (19)	0.15396 (10)	0.0196 (4)
H6	0.6299	0.7888	0.1872	0.024*
C7	1.1243 (2)	1.06428 (18)	0.21942 (10)	0.0193 (4)
C8	1.1177 (2)	0.98549 (18)	0.29244 (10)	0.0177 (4)
C9	1.2552 (2)	0.91402 (19)	0.33230 (10)	0.0218 (4)
H9	1.2563	0.8553	0.3810	0.026*
C10	1.3907 (2)	0.9289 (2)	0.30051 (11)	0.0268 (4)
H10	1.4858	0.8812	0.3267	0.032*
C11	1.3827 (2)	1.0154 (2)	0.22958 (12)	0.0281 (4)
H11	1.4765	1.0292	0.2092	0.034*
C12	0.9706 (2)	0.97694 (18)	0.32529 (10)	0.0172 (4)
C13	0.8552 (2)	0.9442 (2)	0.44828 (10)	0.0213 (4)
H13A	0.7958	0.8599	0.4178	0.026*
H13B	0.7847	1.0317	0.4424	0.026*
C14	1.0901 (2)	1.09491 (19)	0.45951 (10)	0.0206 (4)
H14A	1.0290	1.1885	0.4546	0.025*
H14B	1.1831	1.1118	0.4344	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0278 (3)	0.0355 (3)	0.0253 (3)	0.0012 (2)	−0.00746 (18)	−0.0094 (2)
O1	0.0221 (7)	0.0207 (6)	0.0210 (6)	0.0020 (5)	0.0016 (5)	0.0038 (5)
N1	0.0267 (9)	0.0292 (9)	0.0204 (8)	0.0032 (7)	0.0095 (6)	0.0005 (6)
N2	0.0207 (8)	0.0216 (8)	0.0138 (7)	0.0003 (6)	0.0023 (6)	−0.0020 (6)
N3	0.0202 (8)	0.0238 (8)	0.0124 (7)	−0.0070 (6)	0.0041 (6)	−0.0030 (6)
C1	0.0202 (9)	0.0244 (9)	0.0197 (9)	0.0065 (7)	−0.0027 (7)	−0.0040 (7)
C2	0.0288 (10)	0.0303 (10)	0.0139 (8)	0.0108 (8)	−0.0012 (7)	−0.0010 (7)
C3	0.0262 (10)	0.0282 (10)	0.0175 (9)	0.0086 (8)	0.0051 (7)	0.0050 (7)
C4	0.0206 (9)	0.0195 (9)	0.0193 (9)	0.0061 (7)	0.0024 (7)	0.0003 (7)
C5	0.0193 (9)	0.0211 (9)	0.0151 (8)	0.0060 (7)	0.0032 (7)	−0.0005 (7)
C6	0.0188 (9)	0.0223 (9)	0.0172 (8)	0.0030 (7)	0.0023 (7)	−0.0016 (7)
C7	0.0214 (9)	0.0198 (9)	0.0162 (8)	0.0019 (7)	0.0030 (7)	−0.0034 (7)
C8	0.0207 (9)	0.0182 (8)	0.0138 (8)	−0.0007 (7)	0.0027 (7)	−0.0029 (7)
C9	0.0245 (10)	0.0246 (9)	0.0150 (8)	−0.0004 (7)	0.0012 (7)	0.0008 (7)
C10	0.0228 (10)	0.0332 (11)	0.0233 (9)	0.0058 (8)	0.0022 (8)	−0.0018 (8)
C11	0.0234 (10)	0.0352 (11)	0.0281 (10)	0.0037 (8)	0.0108 (8)	−0.0006 (8)
C12	0.0223 (9)	0.0157 (8)	0.0139 (8)	−0.0007 (7)	0.0045 (7)	−0.0006 (7)
C13	0.0201 (9)	0.0286 (10)	0.0150 (8)	−0.0075 (7)	0.0033 (7)	−0.0030 (7)
C14	0.0232 (9)	0.0242 (9)	0.0149 (8)	−0.0084 (7)	0.0055 (7)	−0.0042 (7)

Geometric parameters (Å, º)

Cl1—C1	1.745 (2)	C5—C6	1.401 (2)
O1—C7	1.386 (2)	C6—H6	0.9500
O1—C4	1.401 (2)	C7—C8	1.394 (2)
N1—C7	1.320 (2)	C8—C9	1.392 (2)
N1—C11	1.340 (2)	C8—C12	1.488 (2)
N2—C12	1.289 (2)	C9—C10	1.389 (3)
N2—C5	1.406 (2)	C9—H9	0.9500
N3—C12	1.388 (2)	C10—C11	1.381 (3)
N3—C13	1.464 (2)	C10—H10	0.9500
N3—C14	1.469 (2)	C11—H11	0.9500
C1—C2	1.378 (3)	C13—C14^i	1.516 (2)
C1—C6	1.386 (2)	C13—H13A	0.9900
C2—C3	1.388 (3)	C13—H13B	0.9900
C2—H2	0.9500	C14—C13^i	1.516 (2)
C3—C4	1.385 (2)	C14—H14A	0.9900
C3—H3	0.9500	C14—H14B	0.9900
C4—C5	1.397 (2)
C7—O1—C4	111.35 (12)	C9—C8—C7	116.56 (16)
C7—N1—C11	116.40 (15)	C9—C8—C12	121.88 (15)
C12—N2—C5	121.72 (14)	C7—C8—C12	121.56 (15)
C12—N3—C13	117.23 (13)	C10—C9—C8	119.66 (16)
C12—N3—C14	118.29 (13)	C10—C9—H9	120.2
C13—N3—C14	111.68 (13)	C8—C9—H9	120.2
C2—C1—C6	122.32 (17)	C11—C10—C9	117.85 (17)
C2—C1—Cl1	119.41 (13)	C11—C10—H10	121.1
C6—C1—Cl1	118.24 (14)	C9—C10—H10	121.1
C1—C2—C3	118.12 (16)	N1—C11—C10	124.14 (17)
C1—C2—H2	120.9	N1—C11—H11	117.9
C3—C2—H2	120.9	C10—C11—H11	117.9
C4—C3—C2	120.34 (17)	N2—C12—N3	118.79 (15)
C4—C3—H3	119.8	N2—C12—C8	126.01 (14)
C2—C3—H3	119.8	N3—C12—C8	114.94 (14)
C3—C4—C5	121.78 (17)	N3—C13—C14^i	109.18 (14)
C3—C4—O1	118.11 (16)	N3—C13—H13A	109.8
C5—C4—O1	120.07 (14)	C14^i—C13—H13A	109.8
C4—C5—C6	117.45 (15)	N3—C13—H13B	109.8
C4—C5—N2	124.77 (16)	C14^i—C13—H13B	109.8
C6—C5—N2	117.49 (15)	H13A—C13—H13B	108.3
C1—C6—C5	119.98 (16)	N3—C14—C13^i	112.08 (14)
C1—C6—H6	120.0	N3—C14—H14A	109.2
C5—C6—H6	120.0	C13^i—C14—H14A	109.2
N1—C7—O1	115.18 (15)	N3—C14—H14B	109.2
N1—C7—C8	125.28 (16)	C13^i—C14—H14B	109.2
O1—C7—C8	119.51 (15)	H14A—C14—H14B	107.9

Symmetry code: (i) −x+2, −y+2, −z+1.