6-Bromo-2-naphthol–piperazine (2/1)

Tian, Y.; Cui, D.

doi:10.1107/S1600536808036878

organic compounds

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Volume 64| Part 12| December 2008| Page o2334

doi:10.1107/S1600536808036878

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6-Bromo-2-naphthol–piperazine (2/1)

Yan Tian ^a and Deliang Cui ^a ^*

^aState Key Laboratory of Crystalline Materials, Shandong University, Jinan 250100, People's Republic of China and School of Chemistry & Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China
^*Correspondence e-mail: cuidl@sdu.edu.cn

(Received 3 November 2008; accepted 9 November 2008; online 13 November 2008)

In the title compound, 2C₁₀H₇BrO·C₄H₁₀N₂, the piperazine (pip) molecule displays a chair conformation and is linked to two molecules of 6-bromo-2-naphthol (bno) via O—H⋯N hydrogen bonds. Weak N—H⋯O hydrogen bonds from pip to bno molecules result in chains propagating in [100]. The chains interact via C—H⋯π interactions.

Related literature

For related structures, see: Wang & Tang (2006a ,b ,c ); Wang et al. (2008 ).

Experimental

Crystal data

2C₁₀H₇BrO·C₄H₁₀N₂
M_r = 532.27
Monoclinic, P 2₁ /n
a = 10.1327 (4) Å
b = 16.2494 (7) Å
c = 14.3499 (5) Å
β = 108.238 (2)°
V = 2244.02 (15) Å³
Z = 4
Mo Kα radiation
μ = 3.63 mm⁻¹
T = 296 (2) K
0.30 × 0.30 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.409, T_max = 0.713
16751 measured reflections
5164 independent reflections
2857 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.107
S = 1.00
5164 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯N1	0.82	1.94	2.743 (4)	168
O2—H2B⋯N2ⁱ	0.83	1.88	2.694 (4)	163
N1—H1C⋯O2	0.83	2.47	3.235 (4)	152
N2—H2A⋯O1ⁱⁱ	0.77	2.50	3.184 (4)	149
C4—H4A⋯Cg5	0.93	2.77	3.471 (3)	133
C14—H14A⋯Cg2ⁱⁱⁱ	0.93	2.68	3.371 (3)	132
C16—H16A⋯Cg1ⁱⁱⁱ	0.93	2.90	3.570 (3)	130
C21—H21A⋯Cg2^iv	0.97	2.93	3.831 (3)	156
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y+1, -z+2; (iv) $[x-{\script{3\over 2}}, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]$ . Cg1, Cg2 and Cg5 are the centroids of atoms C1–C5,C10, C5–C10 and C15–C20, respectively.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036878/hb2836sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808036878/hb2836Isup2.hkl

checkCIF report

Comment top

During the past decade, the field of molecular co-crystals have received considerable attention, for example, the design, construction and properties of molecular co-crystals. Recently, many co-crystals containing some organic acids and bases, have been successfully prepared and characterized by some research groups (Wang et al., 2006a,b,c). Especially, co-crystals containing hydroxyl-naphthalene with some organic bases have been synthesized and characterized (Wang et al., 2008). As part of our investigations of co-crystals containing 6-bromo-2-naphthol (bno), we now report the structure of the co-crystal, (I), of bno and piperazine.

A view of the title structure is shown in Fig. 1. The asymmetric unit consists of two independent bno molecules and one independent molecule of piperazine. In the crystal structure of (I), the piperazine molecule display a chair conformation and links with two molecules of 6-bromo-2-naphthol via O—H···N hydrogen bonds. These motifs are extended to one-dimensional chains via intermolecular edge-to-face C—H···π packing interactions (Fig. 2 and Table 1).

Related literature top

For related structures, see: Wang & Tang (2006a,b,c); Wang et al. (2008). Cg1, Cg2 and Cg5 are the centroids of atoms C1–C5,C10, C5–C10 and C15–C20, respectively.

Experimental top

A mixture of bno (446 mg, 1 mmol) and piperazine (86 mg, 1 mmol) was dissolved in methanol (10 ml), which was left at room temperature. Some colourless plates of (I0 were obtained after ten days. Analysis found (%): C, 54.28; H, 4.53; N, 5.28; requires (%): C, 54.16; H, 4.54; N, 5.26.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A drawing of (I), with displacement ellipsoids for the non-hydrogen atoms drawn at the 30% probability level.
	Fig. 2. Packing diagram of (I); hydrogen bonds are shown by dashed lines.

6-Bromo-2-naphthol–piperazine (2/1) top

Crystal data top

2C₁₀H₇BrO·C₄H₁₀N₂	F(000) = 1072
M_r = 532.27	D_x = 1.575 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3655 reflections
a = 10.1327 (4) Å	θ = 2.5–27.5°
b = 16.2494 (7) Å	µ = 3.64 mm⁻¹
c = 14.3499 (5) Å	T = 296 K
β = 108.238 (2)°	Plate, colourless
V = 2244.02 (15) Å³	0.30 × 0.30 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	5164 independent reflections
Radiation source: fine-focus sealed tube	2857 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 9.00 pixels mm^-1	θ_max = 27.6°, θ_min = 2.0°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −20→21
T_min = 0.409, T_max = 0.713	l = −18→18
16751 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.046P)² + 0.5753P] where P = (F_o² + 2F_c²)/3
5164 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

2C₁₀H₇BrO·C₄H₁₀N₂	V = 2244.02 (15) Å³
M_r = 532.27	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.1327 (4) Å	µ = 3.64 mm⁻¹
b = 16.2494 (7) Å	T = 296 K
c = 14.3499 (5) Å	0.30 × 0.30 × 0.10 mm
β = 108.238 (2)°

Data collection top

Bruker SMART CCD diffractometer	5164 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2857 reflections with I > 2σ(I)
T_min = 0.409, T_max = 0.713	R_int = 0.035
16751 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.00	Δρ_max = 0.52 e Å⁻³
5164 reflections	Δρ_min = −0.39 e Å⁻³
271 parameters

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
Br1	0.90393 (4)	0.69713 (3)	1.25794 (3)	0.07368 (16)
O1	0.5253 (2)	0.59439 (15)	0.67377 (16)	0.0644 (7)
H1B	0.4423	0.5842	0.6586	0.097*
C1	0.6945 (3)	0.6429 (2)	0.8149 (2)	0.0513 (8)
H1A	0.7491	0.6579	0.7762	0.062*
C2	0.5696 (3)	0.6067 (2)	0.7733 (2)	0.0500 (8)
C3	0.4883 (3)	0.5817 (2)	0.8315 (2)	0.0528 (8)
H3A	0.4037	0.5556	0.8023	0.063*
C4	0.5317 (3)	0.59511 (19)	0.9301 (2)	0.0521 (8)
H4A	0.4763	0.5783	0.9674	0.062*
C5	0.6582 (3)	0.63370 (18)	0.9756 (2)	0.0452 (8)
C6	0.7088 (3)	0.64743 (19)	1.0793 (2)	0.0520 (8)
H6A	0.6553	0.6318	1.1184	0.062*
C7	0.8328 (3)	0.6827 (2)	1.1201 (2)	0.0518 (8)
C8	0.9161 (3)	0.70853 (19)	1.0628 (3)	0.0567 (9)
H8A	1.0010	0.7341	1.0924	0.068*
C9	0.8716 (3)	0.6958 (2)	0.9645 (3)	0.0558 (9)
H9A	0.9273	0.7122	0.9272	0.067*
C10	0.7427 (3)	0.65831 (18)	0.9179 (2)	0.0445 (7)
C21	0.1839 (3)	0.6015 (2)	0.5035 (3)	0.0640 (10)
H21A	0.1860	0.6602	0.5158	0.077*
H21B	0.0877	0.5847	0.4757	0.077*
C22	0.2618 (3)	0.5824 (2)	0.4333 (2)	0.0560 (9)
H22A	0.2186	0.6104	0.3715	0.067*
H22B	0.3567	0.6020	0.4597	0.067*
C23	0.3232 (3)	0.4493 (2)	0.5094 (2)	0.0601 (9)
H23A	0.4194	0.4658	0.5383	0.072*
H23B	0.3209	0.3905	0.4974	0.072*
C24	0.2437 (4)	0.4687 (3)	0.5782 (3)	0.0710 (11)
H24A	0.1480	0.4510	0.5501	0.085*
H24B	0.2838	0.4396	0.6396	0.085*
N1	0.2484 (3)	0.5572 (2)	0.5960 (2)	0.0669 (8)
H1C	0.1994	0.5750	0.6287	0.100*
N2	0.2616 (3)	0.49323 (18)	0.41684 (19)	0.0567 (7)
H2A	0.3047	0.4879	0.3813	0.085*
Br2	0.41434 (4)	0.63994 (3)	1.24310 (3)	0.07881 (17)
O2	−0.0266 (2)	0.59459 (14)	0.65772 (15)	0.0587 (6)
H2B	−0.0912	0.5604	0.6430	0.088*
C11	0.1170 (3)	0.65519 (19)	0.8032 (2)	0.0436 (7)
H11A	0.1287	0.7005	0.7670	0.052*
C12	0.0343 (3)	0.59134 (18)	0.7567 (2)	0.0429 (7)
C13	0.0169 (3)	0.52264 (18)	0.8108 (2)	0.0470 (8)
H13A	−0.0407	0.4797	0.7795	0.056*
C14	0.0843 (3)	0.51849 (18)	0.9094 (2)	0.0450 (7)
H14A	0.0734	0.4720	0.9441	0.054*
C15	0.1700 (3)	0.58307 (17)	0.9598 (2)	0.0388 (7)
C16	0.2394 (3)	0.58006 (19)	1.0613 (2)	0.0458 (8)
H16A	0.2318	0.5338	1.0973	0.055*
C17	0.3176 (3)	0.6450 (2)	1.1062 (2)	0.0489 (8)
C18	0.3303 (3)	0.7159 (2)	1.0545 (2)	0.0533 (8)
H18A	0.3826	0.7603	1.0873	0.064*
C19	0.2665 (3)	0.71977 (19)	0.9567 (2)	0.0499 (8)
H19A	0.2765	0.7668	0.9225	0.060*
C20	0.1845 (3)	0.65347 (18)	0.9052 (2)	0.0395 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0786 (3)	0.0808 (3)	0.0568 (3)	−0.0023 (2)	0.0141 (2)	−0.0183 (2)
O1	0.0537 (13)	0.0915 (19)	0.0459 (14)	0.0005 (13)	0.0124 (11)	−0.0070 (13)
C1	0.049 (2)	0.055 (2)	0.054 (2)	0.0111 (16)	0.0221 (17)	0.0048 (16)
C2	0.0456 (19)	0.054 (2)	0.049 (2)	0.0120 (16)	0.0124 (16)	0.0006 (16)
C3	0.0442 (18)	0.060 (2)	0.053 (2)	0.0006 (16)	0.0131 (16)	−0.0032 (17)
C4	0.0430 (18)	0.058 (2)	0.060 (2)	0.0009 (16)	0.0223 (16)	0.0040 (17)
C5	0.0406 (17)	0.0422 (18)	0.055 (2)	0.0082 (15)	0.0182 (15)	0.0014 (15)
C6	0.051 (2)	0.053 (2)	0.055 (2)	0.0066 (17)	0.0208 (17)	−0.0032 (17)
C7	0.052 (2)	0.047 (2)	0.053 (2)	0.0073 (16)	0.0131 (17)	−0.0075 (16)
C8	0.051 (2)	0.048 (2)	0.069 (2)	0.0036 (16)	0.0162 (18)	−0.0050 (17)
C9	0.050 (2)	0.054 (2)	0.069 (2)	0.0040 (17)	0.0269 (18)	0.0024 (18)
C10	0.0386 (17)	0.0399 (18)	0.057 (2)	0.0070 (14)	0.0179 (15)	0.0027 (15)
C21	0.0451 (19)	0.072 (3)	0.073 (3)	0.0027 (18)	0.0160 (18)	−0.006 (2)
C22	0.0477 (19)	0.067 (2)	0.051 (2)	−0.0040 (18)	0.0116 (16)	0.0067 (17)
C23	0.0415 (18)	0.061 (2)	0.072 (2)	−0.0067 (17)	0.0090 (17)	−0.0002 (19)
C24	0.045 (2)	0.107 (3)	0.056 (2)	−0.016 (2)	0.0079 (17)	0.021 (2)
N1	0.0517 (17)	0.103 (3)	0.0512 (18)	−0.0028 (17)	0.0240 (14)	−0.0125 (18)
N2	0.0468 (15)	0.073 (2)	0.0480 (16)	−0.0084 (15)	0.0109 (13)	−0.0097 (15)
Br2	0.0957 (3)	0.0887 (3)	0.0446 (2)	−0.0178 (2)	0.0114 (2)	−0.00418 (19)
O2	0.0544 (13)	0.0687 (16)	0.0464 (14)	−0.0138 (12)	0.0064 (11)	0.0010 (11)
C11	0.0386 (17)	0.0419 (18)	0.0513 (19)	0.0011 (14)	0.0153 (15)	0.0094 (15)
C12	0.0347 (16)	0.047 (2)	0.0464 (19)	0.0035 (15)	0.0110 (14)	0.0000 (15)
C13	0.0427 (17)	0.0382 (18)	0.056 (2)	−0.0048 (14)	0.0095 (15)	−0.0056 (15)
C14	0.0477 (17)	0.0337 (17)	0.054 (2)	0.0003 (15)	0.0163 (15)	0.0046 (15)
C15	0.0359 (16)	0.0357 (17)	0.0458 (18)	0.0038 (13)	0.0141 (14)	0.0001 (14)
C16	0.0447 (18)	0.0460 (19)	0.049 (2)	0.0014 (15)	0.0182 (15)	0.0042 (15)
C17	0.0495 (18)	0.056 (2)	0.0416 (18)	0.0002 (16)	0.0151 (15)	−0.0034 (16)
C18	0.057 (2)	0.049 (2)	0.055 (2)	−0.0079 (16)	0.0181 (17)	−0.0094 (16)
C19	0.057 (2)	0.0390 (19)	0.054 (2)	−0.0082 (15)	0.0184 (17)	−0.0020 (15)
C20	0.0337 (15)	0.0402 (18)	0.0458 (18)	0.0044 (13)	0.0144 (14)	0.0004 (14)

Geometric parameters (Å, º) top

Br1—C7	1.896 (3)	C23—C24	1.490 (5)
O1—C2	1.371 (4)	C23—H23A	0.9700
O1—H1B	0.8168	C23—H23B	0.9700
C1—C2	1.353 (4)	C24—N1	1.460 (5)
C1—C10	1.427 (4)	C24—H24A	0.9700
C1—H1A	0.9300	C24—H24B	0.9700
C2—C3	1.405 (4)	N1—H1C	0.8336
C3—C4	1.361 (4)	N2—H2A	0.7730
C3—H3A	0.9300	Br2—C17	1.903 (3)
C4—C5	1.392 (4)	O2—C12	1.360 (3)
C4—H4A	0.9300	O2—H2B	0.8329
C5—C10	1.423 (4)	C11—C12	1.369 (4)
C5—C6	1.431 (4)	C11—C20	1.408 (4)
C6—C7	1.338 (4)	C11—H11A	0.9300
C6—H6A	0.9300	C12—C13	1.403 (4)
C7—C8	1.414 (5)	C13—C14	1.367 (4)
C8—C9	1.355 (4)	C13—H13A	0.9300
C8—H8A	0.9300	C14—C15	1.409 (4)
C9—C10	1.406 (4)	C14—H14A	0.9300
C9—H9A	0.9300	C15—C16	1.406 (4)
C21—N1	1.470 (4)	C15—C20	1.420 (4)
C21—C22	1.495 (4)	C16—C17	1.356 (4)
C21—H21A	0.9700	C16—H16A	0.9300
C21—H21B	0.9700	C17—C18	1.398 (4)
C22—N2	1.468 (4)	C18—C19	1.350 (4)
C22—H22A	0.9700	C18—H18A	0.9300
C22—H22B	0.9700	C19—C20	1.419 (4)
C23—N2	1.464 (4)	C19—H19A	0.9300

C2—O1—H1B	106.3	N2—C23—H23B	109.8
C2—C1—C10	120.2 (3)	C24—C23—H23B	109.8
C2—C1—H1A	119.9	H23A—C23—H23B	108.2
C10—C1—H1A	119.9	N1—C24—C23	109.2 (3)
C1—C2—O1	118.7 (3)	N1—C24—H24A	109.8
C1—C2—C3	120.3 (3)	C23—C24—H24A	109.8
O1—C2—C3	121.0 (3)	N1—C24—H24B	109.8
C4—C3—C2	120.8 (3)	C23—C24—H24B	109.8
C4—C3—H3A	119.6	H24A—C24—H24B	108.3
C2—C3—H3A	119.6	C24—N1—C21	110.0 (3)
C3—C4—C5	120.7 (3)	C24—N1—H1C	116.5
C3—C4—H4A	119.6	C21—N1—H1C	99.4
C5—C4—H4A	119.6	C23—N2—C22	110.9 (3)
C4—C5—C10	119.1 (3)	C23—N2—H2A	112.0
C4—C5—C6	122.4 (3)	C22—N2—H2A	104.1
C10—C5—C6	118.4 (3)	C12—O2—H2B	107.6
C7—C6—C5	120.3 (3)	C12—C11—C20	121.1 (3)
C7—C6—H6A	119.9	C12—C11—H11A	119.5
C5—C6—H6A	119.9	C20—C11—H11A	119.5
C6—C7—C8	121.4 (3)	O2—C12—C11	119.3 (3)
C6—C7—Br1	120.6 (3)	O2—C12—C13	121.0 (3)
C8—C7—Br1	118.0 (3)	C11—C12—C13	119.8 (3)
C9—C8—C7	119.7 (3)	C14—C13—C12	120.3 (3)
C9—C8—H8A	120.1	C14—C13—H13A	119.9
C7—C8—H8A	120.1	C12—C13—H13A	119.9
C8—C9—C10	121.2 (3)	C13—C14—C15	121.5 (3)
C8—C9—H9A	119.4	C13—C14—H14A	119.3
C10—C9—H9A	119.4	C15—C14—H14A	119.3
C9—C10—C5	118.9 (3)	C16—C15—C14	122.3 (3)
C9—C10—C1	122.3 (3)	C16—C15—C20	119.7 (3)
C5—C10—C1	118.8 (3)	C14—C15—C20	118.1 (3)
N1—C21—C22	109.2 (3)	C17—C16—C15	119.6 (3)
N1—C21—H21A	109.9	C17—C16—H16A	120.2
C22—C21—H21A	109.9	C15—C16—H16A	120.2
N1—C21—H21B	109.9	C16—C17—C18	121.7 (3)
C22—C21—H21B	109.9	C16—C17—Br2	119.5 (2)
H21A—C21—H21B	108.3	C18—C17—Br2	118.7 (2)
N2—C22—C21	109.8 (3)	C19—C18—C17	119.7 (3)
N2—C22—H22A	109.7	C19—C18—H18A	120.1
C21—C22—H22A	109.7	C17—C18—H18A	120.1
N2—C22—H22B	109.7	C18—C19—C20	121.2 (3)
C21—C22—H22B	109.7	C18—C19—H19A	119.4
H22A—C22—H22B	108.2	C20—C19—H19A	119.4
N2—C23—C24	109.4 (3)	C11—C20—C19	122.8 (3)
N2—C23—H23A	109.8	C11—C20—C15	119.3 (3)
C24—C23—H23A	109.8	C19—C20—C15	117.9 (3)

C10—C1—C2—O1	178.7 (3)	C22—C21—N1—C24	−60.3 (4)
C10—C1—C2—C3	−1.9 (5)	C24—C23—N2—C22	58.6 (3)
C1—C2—C3—C4	1.6 (5)	C21—C22—N2—C23	−58.0 (3)
O1—C2—C3—C4	−179.0 (3)	C20—C11—C12—O2	−178.6 (2)
C2—C3—C4—C5	−0.3 (5)	C20—C11—C12—C13	−0.4 (4)
C3—C4—C5—C10	−0.7 (5)	O2—C12—C13—C14	176.8 (3)
C3—C4—C5—C6	−178.7 (3)	C11—C12—C13—C14	−1.3 (4)
C4—C5—C6—C7	178.1 (3)	C12—C13—C14—C15	1.4 (4)
C10—C5—C6—C7	0.1 (4)	C13—C14—C15—C16	179.6 (3)
C5—C6—C7—C8	1.0 (5)	C13—C14—C15—C20	0.2 (4)
C5—C6—C7—Br1	−177.5 (2)	C14—C15—C16—C17	−178.3 (3)
C6—C7—C8—C9	−1.5 (5)	C20—C15—C16—C17	1.2 (4)
Br1—C7—C8—C9	177.0 (2)	C15—C16—C17—C18	0.6 (5)
C7—C8—C9—C10	0.9 (5)	C15—C16—C17—Br2	−178.8 (2)
C8—C9—C10—C5	0.2 (5)	C16—C17—C18—C19	−1.7 (5)
C8—C9—C10—C1	−178.9 (3)	Br2—C17—C18—C19	177.7 (2)
C4—C5—C10—C9	−178.8 (3)	C17—C18—C19—C20	1.0 (5)
C6—C5—C10—C9	−0.7 (4)	C12—C11—C20—C19	−177.4 (3)
C4—C5—C10—C1	0.3 (4)	C12—C11—C20—C15	2.0 (4)
C6—C5—C10—C1	178.4 (3)	C18—C19—C20—C11	−179.7 (3)
C2—C1—C10—C9	−179.9 (3)	C18—C19—C20—C15	0.8 (4)
C2—C1—C10—C5	1.0 (4)	C16—C15—C20—C11	178.7 (3)
N1—C21—C22—N2	58.1 (4)	C14—C15—C20—C11	−1.9 (4)
N2—C23—C24—N1	−59.7 (4)	C16—C15—C20—C19	−1.8 (4)
C23—C24—N1—C21	61.2 (3)	C14—C15—C20—C19	177.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···N1	0.82	1.94	2.743 (4)	168
O2—H2B···N2ⁱ	0.83	1.88	2.694 (4)	163
N1—H1C···O2	0.83	2.47	3.235 (4)	152
N2—H2A···O1ⁱⁱ	0.77	2.50	3.184 (4)	149
C4—H4A···Cg5	0.93	2.77	3.471 (3)	133
C14—H14A···Cg2ⁱⁱⁱ	0.93	2.68	3.371 (3)	132
C16—H16A···Cg1ⁱⁱⁱ	0.93	2.90	3.570 (3)	130
C21—H21A···Cg2^iv	0.97	2.93	3.831 (3)	156

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+1, −z+2; (iv) x−3/2, −y+1/2, z−3/2.

Experimental details

Crystal data
Chemical formula	2C₁₀H₇BrO·C₄H₁₀N₂
M_r	532.27
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	10.1327 (4), 16.2494 (7), 14.3499 (5)
β (°)	108.238 (2)
V (Å³)	2244.02 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.64
Crystal size (mm)	0.30 × 0.30 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.409, 0.713
No. of measured, independent and observed [I > 2σ(I)] reflections	16751, 5164, 2857
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.653

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.107, 1.00
No. of reflections	5164
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.39

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···N1	0.82	1.94	2.743 (4)	168
O2—H2B···N2ⁱ	0.83	1.88	2.694 (4)	163
N1—H1C···O2	0.83	2.47	3.235 (4)	152
N2—H2A···O1ⁱⁱ	0.77	2.50	3.184 (4)	149
C4—H4A···Cg5	0.93	2.77	3.471 (3)	133
C14—H14A···Cg2ⁱⁱⁱ	0.93	2.68	3.371 (3)	132
C16—H16A···Cg1ⁱⁱⁱ	0.93	2.90	3.570 (3)	130
C21—H21A···Cg2^iv	0.97	2.93	3.831 (3)	156

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+1, −z+2; (iv) x−3/2, −y+1/2, z−3/2.

Acknowledgements

This work was supported by the Starting Fund of Shandong University.

References

Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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