2,2'-[1,3-Diazinane-1,3-diylbis(methyl-ene)]bis-(4-bromo-phenol).

The title compound, C(18)H(20)Br(2)N(2)O(2), the heterocyclic ring adopts a chair conformation. The benzene rings make dihedral angles of 86.84 (10) and 60.73 (10)° with the mean plane of the heterocyclic ring. The dihedral angle between the two benzene rings is 79.77 (10)°. The mol-ecular structure is stabilized by two intra-molecular hydrogen bonds between the phenolic hy-droxy groups and N atoms with graph-set motif S(6). The crystal structure is stabilized by weak C-H⋯π inter-actions.

Related literature

For related structures, see: Rivera et al. (2012 ▶, 2011 ▶). For the synthesis of the precursor, see: Rivera et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶). For Cremer–Pople puckering parameters, see: Cremer & Pople (1975 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H20Br2N2O2

M = 456.2

Orthorhombic,

a = 5.9602 (3) Å

b = 17.2164 (8) Å

c = 17.7222 (8) Å

V = 1818.53 (15) Å3

Z = 4

Cu Kα radiation

μ = 5.76 mm−1

T = 120 K

0.35 × 0.09 × 0.03 mm

Data collection

Agilent Xcalibur with an Atlas (Gemini ultra Cu) detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.63, T max = 1

14453 measured reflections

3221 independent reflections

3014 reflections with I > 3σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.056

S = 1.37

3221 reflections

225 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.34 e Å−3

Absolute structure: Flack (1983 ▶), 1894 Friedel pairs

Flack parameter: 0.148 (19)

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/S1600536812001985/bx2397sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001985/bx2397Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812001985/bx2397Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H20Br2N2O2	F(000) = 912
Mr = 456.2	Dx = 1.666 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8581 reflections
a = 5.9602 (3) Å	θ = 3.6–67.0°
b = 17.2164 (8) Å	µ = 5.76 mm−1
c = 17.7222 (8) Å	T = 120 K
V = 1818.53 (15) Å3	Plate, colourless
Z = 4	0.35 × 0.09 × 0.03 mm

Agilent Xcalibur with an Atlas (Gemini ultra Cu) detector diffractometer	3221 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	3014 reflections with I > 3σ(I)
mirror	Rint = 0.034
Detector resolution: 10.3784 pixels mm-1	θmax = 67.2°, θmin = 3.6°
Rotation method data acquisition using ω scans	h = −7→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −20→20
Tmin = 0.63, Tmax = 1	l = −21→20
14453 measured reflections

Refinement on F2	Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2)
R[F2 > 2σ(F2)] = 0.023	(Δ/σ)max = 0.009
wR(F2) = 0.056	Δρmax = 0.27 e Å−3
S = 1.37	Δρmin = −0.34 e Å−3
3221 reflections	Extinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
225 parameters	Extinction coefficient: 360 (70)
2 restraints	Absolute structure: Flack (1983), 1894 Friedel pairs
74 constraints	Flack parameter: 0.148 (19)
H atoms treated by a mixture of independent and constrained refinement

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	Uiso*/Ueq
Br1	0.51306 (8)	0.332316 (17)	1.176266 (16)	0.04042 (10)
Br2	0.49477 (6)	0.037552 (13)	0.485209 (15)	0.03305 (8)
O1	0.9595 (3)	0.38094 (11)	0.87498 (12)	0.0318 (6)
O2	0.9653 (3)	0.28722 (12)	0.66366 (12)	0.0326 (6)
N1	0.5696 (3)	0.35867 (12)	0.80850 (13)	0.0223 (6)
N2	0.5782 (4)	0.36259 (13)	0.67419 (14)	0.0260 (7)
C1	0.4884 (6)	0.32162 (12)	0.74006 (13)	0.0251 (7)
C2	0.4815 (6)	0.43895 (13)	0.81379 (15)	0.0275 (7)
C3	0.5591 (5)	0.48430 (15)	0.74549 (19)	0.0342 (10)
C4	0.4950 (7)	0.44293 (13)	0.67271 (15)	0.0339 (8)
C5	0.5110 (6)	0.31139 (12)	0.87501 (13)	0.0224 (6)
C6	0.6347 (4)	0.33698 (14)	0.94497 (16)	0.0214 (7)
C7	0.8526 (4)	0.36921 (14)	0.94151 (17)	0.0251 (8)
C8	0.9639 (4)	0.38989 (13)	1.00746 (17)	0.0275 (8)
C9	0.8650 (5)	0.37837 (14)	1.07713 (18)	0.0294 (9)
C10	0.6495 (5)	0.34704 (14)	1.08040 (17)	0.0264 (8)
C11	0.5363 (4)	0.32626 (13)	1.01568 (15)	0.0235 (7)
C12	0.5203 (6)	0.32261 (13)	0.60354 (14)	0.0269 (7)
C13	0.6347 (4)	0.24464 (16)	0.59565 (16)	0.0246 (8)
C14	0.8500 (4)	0.23092 (16)	0.62571 (16)	0.0260 (8)
C15	0.9503 (4)	0.15865 (16)	0.61723 (16)	0.0284 (8)
C16	0.8460 (5)	0.10008 (17)	0.57645 (17)	0.0286 (8)
C17	0.6373 (5)	0.11513 (16)	0.54497 (16)	0.0276 (8)
C18	0.5310 (5)	0.18583 (14)	0.55486 (14)	0.0243 (7)
H1a	0.327469	0.323535	0.73903	0.0301*
H1b	0.537131	0.268477	0.73904	0.0301*
H2a	0.537922	0.463141	0.858761	0.0329*
H2b	0.320544	0.437631	0.814856	0.0329*
H3a	0.492548	0.53507	0.746197	0.041*
H3b	0.719001	0.490658	0.747452	0.041*
H4a	0.334638	0.442663	0.667524	0.0406*
H4b	0.559441	0.469861	0.63053	0.0406*
H5a	0.544072	0.257805	0.864932	0.0269*
H5b	0.352306	0.314336	0.883768	0.0269*
H8	1.111007	0.412416	1.004589	0.033*
H9	0.943604	0.39175	1.122599	0.0352*
H11	0.388666	0.304252	1.01925	0.0282*
H12a	0.559537	0.354959	0.561435	0.0322*
H12b	0.360679	0.315774	0.60079	0.0322*
H15	1.093883	0.149064	0.639922	0.0341*
H16	0.916522	0.050365	0.570166	0.0343*
H18	0.385015	0.194273	0.533472	0.0292*
H1o	0.868 (5)	0.370 (2)	0.8398 (15)	0.0382*
H2o	0.884 (5)	0.3266 (14)	0.672 (2)	0.0391*

	U11	U22	U33	U12	U13	U23
Br1	0.0547 (2)	0.04237 (16)	0.02419 (15)	−0.0043 (2)	0.00098 (18)	0.00131 (11)
Br2	0.04040 (16)	0.02472 (13)	0.03402 (15)	−0.00507 (16)	−0.00497 (17)	−0.00090 (10)
O1	0.0236 (11)	0.0369 (9)	0.0350 (11)	−0.0063 (8)	0.0030 (8)	0.0000 (8)
O2	0.0303 (11)	0.0359 (9)	0.0316 (10)	−0.0076 (9)	−0.0048 (9)	−0.0044 (8)
N1	0.0264 (12)	0.0177 (9)	0.0227 (11)	−0.0022 (7)	0.0022 (8)	0.0027 (9)
N2	0.0349 (12)	0.0187 (10)	0.0243 (12)	−0.0034 (8)	0.0010 (9)	0.0019 (9)
C1	0.0291 (13)	0.0211 (10)	0.0250 (12)	−0.0045 (14)	0.0021 (14)	0.0024 (9)
C2	0.0328 (13)	0.0193 (10)	0.0303 (13)	0.0024 (12)	0.0017 (15)	0.0003 (9)
C3	0.049 (2)	0.0172 (11)	0.0367 (17)	−0.0016 (11)	0.0032 (13)	0.0024 (11)
C4	0.0483 (15)	0.0235 (11)	0.0298 (13)	0.0023 (16)	0.0057 (19)	0.0069 (9)
C5	0.0221 (12)	0.0196 (9)	0.0256 (11)	−0.0050 (13)	0.0029 (14)	0.0017 (8)
C6	0.0202 (12)	0.0159 (11)	0.0281 (14)	−0.0005 (10)	−0.0020 (10)	0.0021 (10)
C7	0.0229 (13)	0.0173 (11)	0.0351 (16)	0.0026 (10)	0.0018 (11)	0.0034 (11)
C8	0.0233 (14)	0.0170 (10)	0.0421 (15)	−0.0023 (10)	−0.0081 (12)	0.0035 (10)
C9	0.0354 (15)	0.0160 (12)	0.0366 (17)	0.0013 (11)	−0.0112 (12)	−0.0026 (11)
C10	0.0363 (15)	0.0165 (12)	0.0265 (15)	0.0026 (11)	0.0004 (11)	0.0027 (10)
C11	0.0248 (14)	0.0174 (10)	0.0281 (13)	0.0036 (10)	−0.0006 (11)	0.0024 (9)
C12	0.0306 (14)	0.0264 (11)	0.0236 (12)	0.0002 (13)	−0.0007 (14)	0.0033 (9)
C13	0.0252 (13)	0.0278 (13)	0.0208 (13)	−0.0026 (10)	0.0011 (11)	0.0017 (11)
C14	0.0221 (13)	0.0337 (14)	0.0222 (14)	−0.0064 (11)	−0.0005 (10)	0.0021 (12)
C15	0.0244 (15)	0.0355 (13)	0.0254 (13)	0.0016 (11)	−0.0006 (10)	0.0023 (11)
C16	0.0305 (15)	0.0295 (14)	0.0259 (15)	0.0045 (11)	0.0012 (11)	0.0030 (12)
C17	0.0284 (14)	0.0296 (14)	0.0248 (14)	−0.0042 (11)	0.0028 (11)	0.0041 (12)
C18	0.0221 (14)	0.0291 (11)	0.0217 (11)	−0.0043 (11)	−0.0009 (11)	0.0052 (9)

Br1—C10	1.901 (3)	C5—H5a	0.96
Br2—C17	1.905 (3)	C5—H5b	0.96
O1—C7	1.355 (4)	C6—C7	1.413 (4)
O1—H1o	0.85 (3)	C6—C11	1.396 (4)
O2—C14	1.365 (3)	C7—C8	1.390 (4)
O2—H2o	0.85 (3)	C8—C9	1.382 (4)
N1—C1	1.453 (3)	C8—H8	0.96
N1—C2	1.481 (3)	C9—C10	1.394 (4)
N1—C5	1.474 (3)	C9—H9	0.96
N2—C1	1.465 (3)	C10—C11	1.378 (4)
N2—C4	1.470 (3)	C11—H11	0.96
N2—C12	1.470 (3)	C12—C13	1.512 (4)
C1—H1a	0.96	C12—H12a	0.96
C1—H1b	0.96	C12—H12b	0.96
C2—C3	1.513 (4)	C13—C14	1.410 (4)
C2—H2a	0.96	C13—C18	1.389 (4)
C2—H2b	0.96	C14—C15	1.388 (4)
C3—C4	1.522 (4)	C15—C16	1.388 (4)
C3—H3a	0.96	C15—H15	0.96
C3—H3b	0.96	C16—C17	1.388 (4)
C4—H4a	0.96	C16—H16	0.96
C4—H4b	0.96	C17—C18	1.383 (4)
C5—C6	1.508 (4)	C18—H18	0.96
C7—O1—H1o	108 (2)	C7—C6—C11	118.5 (2)
C14—O2—H2o	111 (2)	O1—C7—C6	121.9 (3)
C1—N1—C2	110.1 (2)	O1—C7—C8	118.0 (2)
C1—N1—C5	110.24 (19)	C6—C7—C8	120.2 (3)
C2—N1—C5	112.4 (2)	C7—C8—C9	120.7 (3)
C1—N2—C4	110.1 (2)	C7—C8—H8	119.6439
C1—N2—C12	111.6 (2)	C9—C8—H8	119.6447
C4—N2—C12	110.3 (2)	C8—C9—C10	119.0 (3)
N1—C1—N2	109.4 (2)	C8—C9—H9	120.4851
N1—C1—H1a	109.4712	C10—C9—H9	120.4852
N1—C1—H1b	109.4714	Br1—C10—C9	118.9 (2)
N2—C1—H1a	109.4709	Br1—C10—C11	120.0 (2)
N2—C1—H1b	109.4715	C9—C10—C11	121.1 (3)
H1a—C1—H1b	109.5538	C6—C11—C10	120.5 (2)
N1—C2—C3	108.8 (2)	C6—C11—H11	119.773
N1—C2—H2a	109.4711	C10—C11—H11	119.7736
N1—C2—H2b	109.4713	N2—C12—C13	112.9 (2)
C3—C2—H2a	109.4717	N2—C12—H12a	109.4712
C3—C2—H2b	109.471	N2—C12—H12b	109.4714
H2a—C2—H2b	110.1093	C13—C12—H12a	109.471
C2—C3—C4	111.1 (2)	C13—C12—H12b	109.471
C2—C3—H3a	109.4713	H12a—C12—H12b	105.8417
C2—C3—H3b	109.4711	C12—C13—C14	121.6 (2)
C4—C3—H3a	109.4717	C12—C13—C18	119.6 (2)
C4—C3—H3b	109.4711	C14—C13—C18	118.7 (2)
H3a—C3—H3b	107.8053	O2—C14—C13	121.7 (2)
N2—C4—C3	109.9 (2)	O2—C14—C15	118.2 (2)
N2—C4—H4a	109.4721	C13—C14—C15	120.1 (2)
N2—C4—H4b	109.4708	C14—C15—C16	121.0 (2)
C3—C4—H4a	109.4712	C14—C15—H15	119.5034
C3—C4—H4b	109.4711	C16—C15—H15	119.5043
H4a—C4—H4b	109.0337	C15—C16—C17	118.4 (3)
N1—C5—C6	112.3 (2)	C15—C16—H16	120.817
N1—C5—H5a	109.4708	C17—C16—H16	120.8173
N1—C5—H5b	109.4703	Br2—C17—C16	119.5 (2)
C6—C5—H5a	109.4717	Br2—C17—C18	118.9 (2)
C6—C5—H5b	109.4716	C16—C17—C18	121.6 (3)
H5a—C5—H5b	106.4462	C13—C18—C17	120.2 (3)
C5—C6—C7	121.9 (3)	C13—C18—H18	119.8928
C5—C6—C11	119.6 (2)	C17—C18—H18	119.8919
?—?—?—?	?

Cg2 is the centroid of the C6–C11 aromatic ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.85 (3)	1.87 (3)	2.634 (3)	148 (3)
O2—H2o···N2	0.85 (3)	1.92 (3)	2.654 (3)	144 (3)
.—···..	.	.	.	.
C11—H11···Cg2i	0.96	2.96	3.632 (2)	128

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C6–C11 aromatic ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1	0.85 (3)	1.87 (3)	2.634 (3)	148 (3)
O2—H2o⋯N2	0.85 (3)	1.92 (3)	2.654 (3)	144 (3)
C11—H11⋯Cg2i	0.96	2.96	3.632 (2)	128

Symmetry code: (i) .