Literature DB >> 22259434

3,3'-(Ethane-1,2-di-yl)bis-(3,4-dihydro-2H-1,3-benzoxazine).

Augusto Rivera, Jairo Camacho, Jaime Ríos-Motta, Karla Fejfarová, Michal Dušek.

Abstract

The title compound, C(18)H(20)N(2)O(2), was prepared by Mannich-type reaction of phenol, ethane-1,2-diamine and formaldehyde. The heterocyclic rings adopt half-chair conformations. The acyclic methyl-ene groups attached to the N atoms are in an axial position. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules into dimers. These dimers are further connected via C-H⋯π contacts.

Entities: CellLine Chemical Disease Gene

Year: 2011 PMID： 22259434 PMCID： PMC3254492 DOI： 10.1107/S1600536811053530

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

Related literature

For related structures see: Rivera et al. (2011 ▶, 2010 ▶). For the preparation of the title compound, see: Rivera et al. (1989 ▶). For ring conformations, see Cremer & Pople (1975 ▶). For weak hydrogen bonds, see: Desiraju & Steiner (1999 ▶).

Experimental

Crystal data

C18H20N2O2 M = 296.4 Monoclinic, a = 10.868 (2) Å b = 5.1693 (13) Å c = 13.327 (3) Å β = 102.623 (18)° V = 730.6 (3) Å3 Z = 2 Cu Kα radiation μ = 0.71 mm−1 T = 120 K 0.97 × 0.10 × 0.04 mm

Data collection

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.77, T max = 1 2799 measured reflections 1341 independent reflections 785 reflections with I > 3σ(I) R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.067 wR(F 2) = 0.171 S = 1.38 1341 reflections 199 parameters H-atom parameters constrained Δρmax = 0.28 e Å−3 Δρmin = −0.25 e Å−3 Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811053530/bt5748sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053530/bt5748Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811053530/bt5748Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₈H₂₀N₂O₂	F(000) = 316
M_r = 296.4	D_x = 1.347 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2yb	Cell parameters from 1061 reflections
a = 10.868 (2) Å	θ = 3.4–65.5°
b = 5.1693 (13) Å	µ = 0.71 mm⁻¹
c = 13.327 (3) Å	T = 120 K
β = 102.623 (18)°	Needle, colourless
V = 730.6 (3) Å³	0.97 × 0.10 × 0.04 mm
Z = 2

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	1341 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	785 reflections with I > 3σ(I)
mirror	R_int = 0.079
Detector resolution: 10.3784 pixels mm^-1	θ_max = 65.7°, θ_min = 3.4°
Rotation method data acquisition using ω scans	h = −12→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −4→5
T_min = 0.77, T_max = 1	l = −15→15
2799 measured reflections

Refinement on F²	81 constraints
R[F² > 2σ(F²)] = 0.067	H-atom parameters constrained
wR(F²) = 0.171	Weighting scheme based on measured s.u.'s w = 1/[σ²(I) + 0.0016I²]
S = 1.38	(Δ/σ)_max = 0.004
1341 reflections	Δρ_max = 0.28 e Å⁻³
199 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints

Experimental. CrysAlisPro (Agilent, 2010) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F² for refinement carried out on F and F², respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

	x	y	z	U_iso*/U_eq
C1	0.9998 (6)	0.619 (2)	0.7044 (5)	0.038 (2)
N1	1.0853 (5)	0.4006 (19)	0.7006 (4)	0.040 (2)
C2	1.2051 (7)	0.420 (2)	0.7681 (6)	0.049 (3)
O1	1.2790 (5)	0.6444 (18)	0.7528 (4)	0.0482 (19)
C3	1.2853 (7)	0.677 (2)	0.6506 (5)	0.039 (3)
C4	1.3740 (7)	0.854 (2)	0.6314 (6)	0.050 (3)
C5	1.3841 (7)	0.898 (2)	0.5301 (6)	0.051 (3)
C6	1.3057 (7)	0.766 (2)	0.4522 (6)	0.049 (3)
C7	1.2171 (7)	0.595 (2)	0.4717 (6)	0.046 (3)
C8	1.2051 (7)	0.549 (2)	0.5724 (5)	0.036 (2)
C9	1.1083 (7)	0.361 (2)	0.5963 (5)	0.040 (3)
C10	0.9615 (6)	0.630 (2)	0.8071 (5)	0.039 (2)
N2	0.8679 (5)	0.8366 (19)	0.8073 (4)	0.036 (2)
C11	0.8763 (7)	0.948 (2)	0.9069 (5)	0.039 (3)
O2	0.8508 (4)	0.7615 (18)	0.9838 (3)	0.0389 (16)
C12	0.7491 (7)	0.605 (2)	0.9472 (5)	0.036 (2)
C13	0.7116 (6)	0.445 (2)	1.0211 (5)	0.037 (2)
C14	0.6127 (7)	0.273 (2)	0.9901 (6)	0.043 (3)
C15	0.5531 (7)	0.262 (2)	0.8873 (5)	0.039 (2)
C16	0.5905 (6)	0.416 (2)	0.8150 (5)	0.040 (3)
C17	0.6897 (6)	0.589 (2)	0.8434 (5)	0.033 (2)
C18	0.7386 (6)	0.756 (2)	0.7673 (5)	0.035 (2)
H1a	0.925907	0.601938	0.65019	0.0451*
H1b	1.040864	0.777887	0.693451	0.0451*
H2a	1.252659	0.265585	0.763506	0.0584*
H2b	1.195273	0.416764	0.837985	0.0584*
H4	1.427396	0.94568	0.687131	0.0595*
H5	1.444994	1.018264	0.5152	0.0611*
H6	1.313009	0.793375	0.382469	0.0593*
H7	1.163036	0.505915	0.415763	0.0546*
H9a	1.030594	0.380027	0.546277	0.0478*
H9b	1.136814	0.186835	0.590176	0.0478*
H10a	0.926386	0.466841	0.820454	0.0473*
H10b	1.034626	0.662279	0.860732	0.0473*
H11a	0.958427	1.021981	0.930714	0.0474*
H11b	0.818703	1.090401	0.901728	0.0474*
H13	0.754437	0.454456	1.092073	0.0449*
H14	0.585732	0.163708	1.039393	0.0519*
H15	0.484253	0.143471	0.865763	0.0472*
H16	0.547427	0.403116	0.744117	0.0481*
H18a	0.733488	0.661676	0.70447	0.0422*
H18b	0.685945	0.905848	0.750886	0.0422*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.041 (4)	0.046 (4)	0.027 (3)	0.005 (4)	0.010 (3)	0.005 (3)
N1	0.042 (3)	0.041 (3)	0.038 (4)	0.008 (3)	0.012 (3)	0.002 (3)
C2	0.058 (5)	0.053 (5)	0.037 (4)	0.011 (5)	0.013 (4)	0.010 (4)
O1	0.049 (3)	0.064 (3)	0.029 (3)	0.002 (3)	0.003 (2)	−0.004 (3)
C3	0.044 (5)	0.044 (4)	0.029 (4)	−0.002 (4)	0.008 (3)	−0.001 (3)
C4	0.039 (4)	0.050 (5)	0.059 (6)	−0.001 (4)	0.009 (4)	−0.017 (4)
C5	0.053 (5)	0.035 (4)	0.068 (6)	−0.005 (4)	0.022 (4)	−0.006 (4)
C6	0.060 (5)	0.040 (4)	0.053 (5)	0.003 (5)	0.023 (4)	0.004 (4)
C7	0.054 (5)	0.040 (4)	0.043 (4)	0.002 (4)	0.010 (4)	−0.001 (4)
C8	0.045 (4)	0.034 (4)	0.028 (4)	0.004 (4)	0.009 (3)	−0.002 (3)
C9	0.047 (5)	0.035 (4)	0.040 (4)	−0.002 (3)	0.014 (3)	−0.004 (3)
C10	0.048 (4)	0.044 (4)	0.025 (4)	0.006 (4)	0.006 (3)	0.003 (3)
N2	0.036 (3)	0.041 (3)	0.033 (4)	0.003 (3)	0.010 (3)	0.002 (3)
C11	0.042 (4)	0.034 (4)	0.042 (4)	−0.003 (4)	0.008 (3)	0.004 (3)
O2	0.046 (3)	0.036 (2)	0.032 (3)	−0.008 (3)	0.004 (2)	−0.001 (2)
C12	0.039 (4)	0.033 (4)	0.035 (4)	0.000 (4)	0.009 (3)	−0.001 (3)
C13	0.043 (4)	0.046 (4)	0.024 (4)	0.003 (4)	0.011 (3)	−0.003 (3)
C14	0.050 (5)	0.041 (4)	0.041 (4)	−0.001 (4)	0.016 (3)	−0.004 (4)
C15	0.044 (4)	0.035 (4)	0.039 (4)	−0.004 (4)	0.008 (3)	−0.001 (3)
C16	0.043 (4)	0.042 (4)	0.035 (4)	0.004 (4)	0.008 (3)	−0.004 (3)
C17	0.038 (4)	0.039 (4)	0.022 (3)	0.003 (4)	0.005 (3)	−0.007 (3)
C18	0.046 (4)	0.030 (3)	0.028 (4)	0.008 (4)	0.006 (3)	0.006 (3)

C1—N1	1.471 (13)	C10—N2	1.474 (12)
C1—C10	1.516 (10)	C10—H10a	0.96
C1—H1a	0.96	C10—H10b	0.96
C1—H1b	0.96	N2—C11	1.431 (10)
N1—C2	1.416 (9)	N2—C18	1.450 (9)
N1—C9	1.480 (10)	C11—O2	1.475 (11)
C2—O1	1.451 (13)	C11—H11a	0.96
C2—H2a	0.96	C11—H11b	0.96
C2—H2b	0.96	O2—C12	1.370 (10)
O1—C3	1.388 (9)	C12—C13	1.415 (12)
C3—C4	1.394 (13)	C12—C17	1.395 (9)
C3—C8	1.373 (11)	C13—C14	1.386 (12)
C4—C5	1.397 (12)	C13—H13	0.96
C4—H4	0.96	C14—C15	1.383 (9)
C5—C6	1.373 (12)	C14—H14	0.96
C5—H5	0.96	C15—C16	1.378 (12)
C6—C7	1.373 (13)	C15—H15	0.96
C6—H6	0.96	C16—C17	1.390 (12)
C7—C8	1.397 (11)	C16—H16	0.96
C7—H7	0.96	C17—C18	1.514 (12)
C8—C9	1.518 (13)	C18—H18a	0.96
C9—H9a	0.96	C18—H18b	0.96
C9—H9b	0.96

N1—C1—C10	111.1 (7)	C1—C10—N2	110.8 (7)
N1—C1—H1a	109.4711	C1—C10—H10a	109.4713
N1—C1—H1b	109.4709	C1—C10—H10b	109.4708
C10—C1—H1a	109.4717	N2—C10—H10a	109.4714
C10—C1—H1b	109.4713	N2—C10—H10b	109.4714
H1a—C1—H1b	107.7691	H10a—C10—H10b	108.1247
C1—N1—C2	115.1 (8)	C10—N2—C11	112.8 (6)
C1—N1—C9	112.2 (6)	C10—N2—C18	113.9 (8)
C2—N1—C9	106.6 (6)	C11—N2—C18	108.4 (6)
N1—C2—O1	115.3 (7)	N2—C11—O2	113.5 (8)
N1—C2—H2a	109.4712	N2—C11—H11a	109.4711
N1—C2—H2b	109.4708	N2—C11—H11b	109.4713
O1—C2—H2a	109.4715	O2—C11—H11a	109.4716
O1—C2—H2b	109.4712	O2—C11—H11b	109.4711
H2a—C2—H2b	102.9256	H11a—C11—H11b	105.115
C2—O1—C3	112.5 (7)	C11—O2—C12	113.3 (5)
O1—C3—C4	116.4 (7)	O2—C12—C13	115.5 (6)
O1—C3—C8	121.8 (8)	O2—C12—C17	123.5 (8)
C4—C3—C8	121.8 (7)	C13—C12—C17	120.9 (8)
C3—C4—C5	119.1 (8)	C12—C13—C14	119.4 (6)
C3—C4—H4	120.4314	C12—C13—H13	120.2967
C5—C4—H4	120.4309	C14—C13—H13	120.2963
C4—C5—C6	119.0 (9)	C13—C14—C15	119.2 (8)
C4—C5—H5	120.5111	C13—C14—H14	120.4096
C6—C5—H5	120.5112	C15—C14—H14	120.4094
C5—C6—C7	121.4 (8)	C14—C15—C16	121.5 (8)
C5—C6—H6	119.2825	C14—C15—H15	119.2499
C7—C6—H6	119.2824	C16—C15—H15	119.2504
C6—C7—C8	120.5 (7)	C15—C16—C17	120.8 (6)
C6—C7—H7	119.7553	C15—C16—H16	119.6195
C8—C7—H7	119.7559	C17—C16—H16	119.6206
C3—C8—C7	118.1 (8)	C12—C17—C16	118.3 (8)
C3—C8—C9	120.3 (7)	C12—C17—C18	118.4 (7)
C7—C8—C9	121.6 (7)	C16—C17—C18	123.4 (6)
N1—C9—C8	112.0 (7)	N2—C18—C17	111.8 (5)
N1—C9—H9a	109.4708	N2—C18—H18a	109.4715
N1—C9—H9b	109.4706	N2—C18—H18b	109.4717
C8—C9—H9a	109.4711	C17—C18—H18a	109.471
C8—C9—H9b	109.4722	C17—C18—H18b	109.4706
H9a—C9—H9b	106.8364	H18a—C18—H18b	107.0112

?—?—?—?	?

Cg4 is the centroid of the C12–C17 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11a···O2ⁱ	0.96	2.47	3.415 (10)	168.
C11—H11b···Cg4ⁱⁱ	0.96	2.58	3.523 (10)	169

Table 1

Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C12–C17 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11a⋯O2ⁱ	0.96	2.47	3.415 (10)	168
C11—H11b⋯Cg4ⁱⁱ	0.96	2.58	3.523 (10)	169

Symmetry codes: (i) ; (ii) .

2 in total

1. 3,3'-Ethyl-enebis(3,4-dihydro-6-chloro-2H-1,3-benzoxazine).

Authors: Augusto Rivera; Jicli José Rojas; Jaime Ríos-Motta; Michal Dušek; Karla Fejfarová
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-04-21

2. 3,3'-(Ethane-1,2-di-yl)bis-(6-methyl-3,4-dihydro-2H-1,3-benzoxazine).

Authors: Augusto Rivera; Jairo Camacho; Jaime Ríos-Motta; Michaela Pojarová; Michal Dušek
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2011-07-13

2 in total

5 in total

1. Crystal structure of 1,2-bis-(6-bromo-3,4-dihydro-2H-benz[e][1,3]oxazin-3-yl)ethane: a bromine-containing bis-benzoxazine.

Authors: Augusto Rivera; Jicli José' Rojas; Jaime Ríos-Motta; Michael Bolte
Journal: Acta Crystallogr E Crystallogr Commun Date: 2016-10-25

2. Crystal structure and C-H⋯F hydrogen bonding in the fluorinated bis-benzoxazine: 3,3'-(ethane-1,2-di-yl)bis-(6-fluoro-3,4-di-hydro-2H-1,3-benzoxazine).

Authors: Augusto Rivera; Jicli José Rojas; Jaime Ríos-Motta; Michael Bolte
Journal: Acta Crystallogr E Crystallogr Commun Date: 2016-09-30

3. C-I⋯N short contacts as tools for the construction of the crystal packing in the crystal structure of 3,3'-(ethane-1,2-di-yl)bis-(6-iodo-3,4-di-hydro-2H-1,3-benzoxazine).

Authors: Augusto Rivera; Jicli José Rojas; Jaime Ríos-Motta; Michael Bolte
Journal: Acta Crystallogr E Crystallogr Commun Date: 2017-04-07

4. Crystal structure of 2,2'-(ethane-1,2-di-yl)bis-(2,3-di-hydro-1H-naphtho-[1,2-e][1,3]oxazine): a prospective raw material for polybenzoxazines.

Authors: Augusto Rivera; Juan E Cepeda-Santamaría; Jaime Ríos-Motta; Michael Bolte
Journal: Acta Crystallogr E Crystallogr Commun Date: 2017-05-09

5. 3,3'-(Ethane-1,2-diyl)bis(6-meth-oxy-3,4-dihydro-2H-1,3-benzoxazine) mono-hydrate.

Authors: Augusto Rivera; Jairo Camacho; Jaime Ríos-Motta; Monika Kučeraková; Michal Dušek
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-08-23

5 in total