2-Amino-4-(4-bromo­phen­yl)-6-meth­oxy-4H-benzo[h]chromene-3-carbonitrile

Al-dies, A.M.; El-Agrody, A.M.; Al-Omar, M.A.; Amr, A.E.-G.E.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536813005461

organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Pages o480-o481

doi:10.1107/S1600536813005461

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2-Amino-4-(4-bromophenyl)-6-methoxy-4H-benzo[h]chromene-3-carbonitrile

Al-anood M. Al-dies,^a Ahmed M. El-Agrody,^a,^b Mohamed A. Al-Omar,^c,^d Abd El-Galil E. Amr,^d,^e ‡ Seik Weng Ng ^f,^g and Edward R. T. Tiekink ^f ^*

^aChemistry Department, Faculty of Science, King Khalid University, Abha 61413, PO Box 9004, Saudi Arabia, ^bChemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, 11884, Egypt, ^cPharmaceutical Chemistry Department, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^dDrug Exploration & Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^eApplied Organic Chemistry Department, National Research Center, Dokki 12622, Cairo, Egypt, ^fDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^gChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 25 February 2013; accepted 25 February 2013; online 2 March 2013)

In the title compound, C₂₁H₁₅BrN₂O₂, the 14 non-H atoms of the 4H-benzo[h]chromene fused-ring system are approximately coplanar (r.m.s. deviation = 0.129 Å). Within this system, the 4H-pyran ring adopts a flattened half-chair conformation with the methine C atom lying 0.281 (4) Å above the plane of the remaining atoms (r.m.s. deviation = 0.0446 Å). The bromobenzene ring is almost perpendicular to the fused-ring system [dihedral angle = 85.34 (13)°]. In the crystal, supramolecular layers parallel to (101) are sustained by amine–cyano N—H⋯N and amine–methoxy N—H⋯O hydrogen bonds. The layers stack with interactions of the type (bromobenzene)C—H⋯π(outer-C₆ ring of the fused-ring system) connecting them.

Related literature

For background to biologically active molecules having the 4H-chromene or 4H-benzochromene residue, see: Sabry et al. (2011 ); Amin et al. (2010 ); Kidwai et al. (2010 ); Singh et al. (2010 ), For the structure of the fluoro derivative, see: Al-Dies et al. (2012 ).

Experimental

Crystal data

C₂₁H₁₅BrN₂O₂
M_r = 407.26
Monoclinic, P 2₁ /c
a = 6.0823 (7) Å
b = 16.6918 (18) Å
c = 17.7700 (16) Å
β = 93.646 (9)°
V = 1800.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.30 mm⁻¹
T = 295 K
0.30 × 0.10 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.694, T_max = 1.000
8976 measured reflections
4144 independent reflections
2250 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.150
S = 1.03
4144 reflections
243 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.71 e Å⁻³
Δρ_min = −0.78 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2ⁱ	0.88 (1)	2.22 (2)	3.059 (5)	159 (4)
N1—H2⋯O2ⁱⁱ	0.87 (3)	2.56 (5)	3.324 (4)	147 (4)
C18—H18⋯Cg1ⁱⁱⁱ	0.93	2.87	3.528 (4)	129
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813005461/hb7048sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813005461/hb7048Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813005461/hb7048Isup3.cml

checkCIF report

Comment top

Nitrogen-containing heterocyclic compounds having a 4H-chromene or 4H-benzochromene residue are often found in biologically active molecules (Amin et al., 2010; Kidwai et al., 2010; Singh et al., 2010). As part of our on-going program investigating the chemistry of 4H-pyran derivatives (Sabry et al., 2011), we now report the synthesis of the title compound, (I), and its crystal structure.

In (I), Fig. 1, the 4H-pyran ring approximates a half-chair conformation with the methine-C11 atom lying 0.281 (4) Å out of the least-squares plane defined by the remaining atoms (O1,C1,C10,C12,C13) which has a r.m.s. deviation of 0.0446 Å. Nevertheless, the 14 non-hydrogen atoms comprising the sequence of three six-membered rings of the 4H-benzo[h]chromene residue approximate a plane with the r.m.s. deviation of the fitted atoms being 0.129 Å. The bromobenzene ring forms a dihedral angle of 85.34 (13)° with this plane, indicating an almost perpendicular relationship. The methoxy group is co-planar with the ring to which it is connected as seen in the value of the C14—O2—C8—C7 torsion angle of 177.4 (3)°. The overall structure resembles closely the recently reported fluoro derivative (Al-Dies et al., 2012).

In the crystal packing, amine-N—H···N(cyano) hydrogen bonds between centrosymmetrically related molecules lead to dimeric aggregates, stabilized by 12-membered {···HNC₃N}₂ synthons, which are connected into a supramolecular layer parallel to (1 0 1) by amine-N—H···O(methoxy) hydrogen bonds, Fig. 2 and Table 1. Layers stack with the main interactions between them being of the type (bromobenzene)C—H···π(outer-C₆ ring of the fused ring system), Fig. 3 and Table 1.

Related literature top

For background to biologically active molecules having the 4H-chromene or 4H-benzochromene residue, see: Sabry et al. (2011); Amin et al. (2010); Kidwai et al. (2010); Singh et al. (2010), For the structure of the fluoro derivative, see: Al-Dies et al. (2012).

Experimental top

A solution of 4-methoxy-1-naphthol (0.01 mol) in EtOH (30 ml) was treated with α-cyano-p-bromocinnamonitrile (0.01 mol) and piperidine (0.5 ml). The reaction mixture was heated until complete precipitation occurred (reaction time: 60 min). The solid product which formed was collected by filtration and recrystallized from ethanol to give the title compound as yellow prisms; M. pt: 503–504 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 35% probability level.
	Fig. 2. A view of the supramolecular layer parallel to (1 0 1) in (I). The N—H···N and N—H···O hydrogen bonds are shown as blue and orange dashed lines, respectively.
	Fig. 3. View in projection down the b axis of the crystal packing in (I). The N—H···N, N—H···O and C—H···π interactions are shown as blue, orange and purple dashed lines, respectively. One layer has been highlighted in space-filling mode.

2-Amino-4-(4-bromophenyl)-6-methoxy-4H-benzo[h]chromene-3-carbonitrile top

Crystal data top

C₂₁H₁₅BrN₂O₂	F(000) = 824
M_r = 407.26	D_x = 1.502 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1634 reflections
a = 6.0823 (7) Å	θ = 3.4–27.5°
b = 16.6918 (18) Å	µ = 2.30 mm⁻¹
c = 17.7700 (16) Å	T = 295 K
β = 93.646 (9)°	Prism, yellow
V = 1800.4 (3) Å³	0.30 × 0.10 × 0.10 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4144 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2250 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.041
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 3.4°
ω scan	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −15→21
T_min = 0.694, T_max = 1.000	l = −22→23
8976 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.057P)² + 0.4428P] where P = (F_o² + 2F_c²)/3
4144 reflections	(Δ/σ)_max < 0.001
243 parameters	Δρ_max = 0.71 e Å⁻³
2 restraints	Δρ_min = −0.78 e Å⁻³

Crystal data top

C₂₁H₁₅BrN₂O₂	V = 1800.4 (3) Å³
M_r = 407.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.0823 (7) Å	µ = 2.30 mm⁻¹
b = 16.6918 (18) Å	T = 295 K
c = 17.7700 (16) Å	0.30 × 0.10 × 0.10 mm
β = 93.646 (9)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4144 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2250 reflections with I > 2σ(I)
T_min = 0.694, T_max = 1.000	R_int = 0.041
8976 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	2 restraints
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.71 e Å⁻³
4144 reflections	Δρ_min = −0.78 e Å⁻³
243 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.16537 (9)	0.98612 (4)	0.33868 (3)	0.0969 (3)
O1	0.0181 (4)	0.64654 (15)	0.64437 (13)	0.0504 (6)
O2	0.1773 (4)	0.92192 (15)	0.81237 (13)	0.0573 (7)
N1	0.1307 (6)	0.5382 (2)	0.5848 (2)	0.0582 (8)
H1	0.207 (7)	0.513 (3)	0.552 (2)	0.093 (17)*
H2	0.008 (4)	0.517 (3)	0.598 (3)	0.089 (17)*
N2	0.6286 (6)	0.5888 (2)	0.50299 (19)	0.0676 (9)
C1	0.0644 (5)	0.7191 (2)	0.68158 (16)	0.0393 (8)
C2	−0.0802 (5)	0.73721 (19)	0.73914 (16)	0.0375 (7)
C3	−0.2638 (6)	0.6894 (2)	0.75334 (18)	0.0453 (8)
H3	−0.2931	0.6437	0.7246	0.054*
C4	−0.3989 (6)	0.7094 (2)	0.80851 (19)	0.0520 (9)
H4	−0.5225	0.6783	0.8160	0.062*
C5	−0.3531 (6)	0.7762 (2)	0.8539 (2)	0.0547 (10)
H5	−0.4446	0.7887	0.8922	0.066*
C6	−0.1753 (6)	0.8235 (2)	0.84260 (18)	0.0500 (9)
H6	−0.1447	0.8672	0.8741	0.060*
C7	−0.0360 (5)	0.8068 (2)	0.78307 (17)	0.0405 (8)
C8	0.1447 (6)	0.8565 (2)	0.76620 (17)	0.0430 (8)
C9	0.2710 (5)	0.8382 (2)	0.70790 (18)	0.0446 (8)
H9	0.3847	0.8725	0.6964	0.054*
C10	0.2321 (5)	0.7680 (2)	0.66466 (16)	0.0390 (7)
C11	0.3774 (5)	0.7476 (2)	0.60075 (17)	0.0411 (8)
H11	0.5311	0.7556	0.6192	0.049*
C12	0.3481 (5)	0.6601 (2)	0.58086 (17)	0.0419 (8)
C13	0.1747 (6)	0.6157 (2)	0.60137 (18)	0.0455 (8)
C14	0.3613 (7)	0.9720 (2)	0.8004 (2)	0.0635 (11)
H14A	0.3620	1.0166	0.8345	0.095*
H14B	0.3509	0.9913	0.7494	0.095*
H14C	0.4949	0.9419	0.8092	0.095*
C15	0.5037 (6)	0.6215 (2)	0.53744 (19)	0.0479 (9)
C16	0.3287 (5)	0.8045 (2)	0.53448 (17)	0.0409 (8)
C17	0.1278 (6)	0.8030 (3)	0.4940 (2)	0.0577 (10)
H17	0.0232	0.7651	0.5058	0.069*
C18	0.0789 (6)	0.8566 (3)	0.4364 (2)	0.0627 (11)
H18	−0.0580	0.8551	0.4100	0.075*
C19	0.2331 (7)	0.9121 (2)	0.41810 (19)	0.0549 (10)
C20	0.4365 (6)	0.9136 (2)	0.4556 (2)	0.0581 (10)
H20	0.5421	0.9504	0.4423	0.070*
C21	0.4832 (6)	0.8596 (2)	0.51378 (19)	0.0505 (9)
H21	0.6214	0.8606	0.5394	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1155 (5)	0.0841 (4)	0.0888 (4)	−0.0019 (3)	−0.0114 (3)	0.0431 (3)
O1	0.0523 (13)	0.0429 (15)	0.0572 (13)	−0.0032 (11)	0.0139 (11)	−0.0239 (12)
O2	0.0760 (17)	0.0383 (15)	0.0578 (14)	−0.0057 (13)	0.0074 (12)	−0.0170 (12)
N1	0.063 (2)	0.0407 (19)	0.073 (2)	−0.0020 (17)	0.0213 (18)	−0.0202 (17)
N2	0.079 (2)	0.054 (2)	0.073 (2)	0.0104 (19)	0.0324 (18)	0.0012 (18)
C1	0.0484 (19)	0.0320 (18)	0.0372 (16)	0.0036 (15)	0.0016 (15)	−0.0055 (14)
C2	0.0478 (18)	0.0313 (17)	0.0333 (15)	0.0080 (15)	0.0011 (14)	−0.0027 (14)
C3	0.056 (2)	0.0330 (19)	0.0466 (19)	0.0026 (16)	0.0040 (16)	0.0014 (16)
C4	0.056 (2)	0.049 (2)	0.053 (2)	0.0027 (18)	0.0115 (18)	0.0047 (18)
C5	0.066 (2)	0.050 (2)	0.050 (2)	0.008 (2)	0.0177 (18)	−0.0008 (18)
C6	0.070 (2)	0.039 (2)	0.0417 (18)	0.0098 (19)	0.0078 (17)	−0.0074 (16)
C7	0.0516 (19)	0.0335 (18)	0.0361 (16)	0.0076 (16)	−0.0003 (15)	0.0001 (14)
C8	0.057 (2)	0.0304 (18)	0.0404 (17)	0.0094 (16)	−0.0021 (16)	−0.0060 (15)
C9	0.0510 (19)	0.0344 (19)	0.0482 (19)	0.0006 (16)	0.0011 (16)	−0.0017 (15)
C10	0.0486 (18)	0.0333 (18)	0.0353 (16)	0.0043 (16)	0.0041 (14)	−0.0009 (14)
C11	0.0445 (18)	0.040 (2)	0.0390 (17)	0.0029 (16)	0.0023 (14)	−0.0008 (15)
C12	0.0511 (19)	0.0356 (19)	0.0397 (17)	0.0065 (16)	0.0087 (15)	0.0006 (15)
C13	0.056 (2)	0.041 (2)	0.0400 (17)	0.0097 (18)	0.0032 (16)	−0.0114 (16)
C14	0.066 (2)	0.041 (2)	0.083 (3)	−0.005 (2)	0.000 (2)	−0.016 (2)
C15	0.063 (2)	0.037 (2)	0.0444 (18)	0.0100 (18)	0.0124 (17)	0.0034 (16)
C16	0.0457 (18)	0.0371 (19)	0.0399 (17)	0.0018 (16)	0.0032 (15)	−0.0047 (15)
C17	0.052 (2)	0.062 (3)	0.059 (2)	−0.0083 (19)	−0.0018 (18)	0.013 (2)
C18	0.057 (2)	0.071 (3)	0.059 (2)	−0.005 (2)	−0.0058 (19)	0.015 (2)
C19	0.076 (3)	0.043 (2)	0.0458 (19)	0.004 (2)	−0.0022 (19)	0.0060 (17)
C20	0.066 (2)	0.047 (2)	0.062 (2)	−0.014 (2)	0.008 (2)	0.0042 (19)
C21	0.051 (2)	0.047 (2)	0.053 (2)	−0.0032 (18)	−0.0037 (17)	−0.0006 (18)

Geometric parameters (Å, º) top

Br1—C19	1.901 (3)	C8—C9	1.363 (5)
O1—C13	1.360 (4)	C9—C10	1.413 (4)
O1—C1	1.399 (4)	C9—H9	0.9300
O2—C8	1.372 (4)	C10—C11	1.521 (4)
O2—C14	1.423 (5)	C11—C12	1.510 (5)
N1—C13	1.349 (5)	C11—C16	1.528 (4)
N1—H1	0.877 (10)	C11—H11	0.9800
N1—H2	0.874 (10)	C12—C13	1.357 (5)
N2—C15	1.144 (4)	C12—C15	1.414 (5)
C1—C10	1.355 (5)	C14—H14A	0.9600
C1—C2	1.423 (4)	C14—H14B	0.9600
C2—C3	1.408 (5)	C14—H14C	0.9600
C2—C7	1.416 (4)	C16—C17	1.378 (5)
C3—C4	1.360 (5)	C16—C21	1.382 (5)
C3—H3	0.9300	C17—C18	1.378 (5)
C4—C5	1.395 (5)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.372 (5)
C5—C6	1.364 (5)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.368 (5)
C6—C7	1.424 (5)	C20—C21	1.387 (5)
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.424 (5)	C21—H21	0.9300

C13—O1—C1	117.8 (3)	C12—C11—C16	114.0 (3)
C8—O2—C14	117.6 (3)	C10—C11—C16	110.1 (3)
C13—N1—H1	120 (3)	C12—C11—H11	107.8
C13—N1—H2	120 (3)	C10—C11—H11	107.8
H1—N1—H2	118 (5)	C16—C11—H11	107.8
C10—C1—O1	123.2 (3)	C13—C12—C15	117.1 (3)
C10—C1—C2	122.6 (3)	C13—C12—C11	123.2 (3)
O1—C1—C2	114.1 (3)	C15—C12—C11	119.7 (3)
C3—C2—C7	119.4 (3)	N1—C13—C12	127.7 (3)
C3—C2—C1	122.8 (3)	N1—C13—O1	110.5 (3)
C7—C2—C1	117.8 (3)	C12—C13—O1	121.9 (3)
C4—C3—C2	120.9 (3)	O2—C14—H14A	109.5
C4—C3—H3	119.6	O2—C14—H14B	109.5
C2—C3—H3	119.6	H14A—C14—H14B	109.5
C3—C4—C5	120.3 (4)	O2—C14—H14C	109.5
C3—C4—H4	119.8	H14A—C14—H14C	109.5
C5—C4—H4	119.8	H14B—C14—H14C	109.5
C6—C5—C4	120.6 (3)	N2—C15—C12	178.6 (4)
C6—C5—H5	119.7	C17—C16—C21	117.9 (3)
C4—C5—H5	119.7	C17—C16—C11	120.8 (3)
C5—C6—C7	120.7 (3)	C21—C16—C11	121.2 (3)
C5—C6—H6	119.7	C18—C17—C16	121.2 (4)
C7—C6—H6	119.7	C18—C17—H17	119.4
C2—C7—C8	119.0 (3)	C16—C17—H17	119.4
C2—C7—C6	118.0 (3)	C19—C18—C17	119.8 (3)
C8—C7—C6	123.1 (3)	C19—C18—H18	120.1
C9—C8—O2	124.5 (3)	C17—C18—H18	120.1
C9—C8—C7	120.6 (3)	C20—C19—C18	120.5 (3)
O2—C8—C7	114.9 (3)	C20—C19—Br1	119.7 (3)
C8—C9—C10	121.1 (3)	C18—C19—Br1	119.7 (3)
C8—C9—H9	119.5	C19—C20—C21	119.1 (4)
C10—C9—H9	119.5	C19—C20—H20	120.4
C1—C10—C9	118.8 (3)	C21—C20—H20	120.4
C1—C10—C11	120.8 (3)	C16—C21—C20	121.4 (3)
C9—C10—C11	120.4 (3)	C16—C21—H21	119.3
C12—C11—C10	109.0 (3)	C20—C21—H21	119.3

C13—O1—C1—C10	14.6 (4)	C8—C9—C10—C11	−178.8 (3)
C13—O1—C1—C2	−165.3 (3)	C1—C10—C11—C12	−17.0 (4)
C10—C1—C2—C3	175.4 (3)	C9—C10—C11—C12	162.5 (3)
O1—C1—C2—C3	−4.7 (4)	C1—C10—C11—C16	108.7 (3)
C10—C1—C2—C7	−4.1 (4)	C9—C10—C11—C16	−71.8 (4)
O1—C1—C2—C7	175.8 (3)	C10—C11—C12—C13	17.6 (4)
C7—C2—C3—C4	0.1 (5)	C16—C11—C12—C13	−105.8 (3)
C1—C2—C3—C4	−179.4 (3)	C10—C11—C12—C15	−163.8 (3)
C2—C3—C4—C5	−2.3 (5)	C16—C11—C12—C15	72.8 (4)
C3—C4—C5—C6	1.5 (5)	C15—C12—C13—N1	−0.6 (5)
C4—C5—C6—C7	1.6 (5)	C11—C12—C13—N1	178.1 (3)
C3—C2—C7—C8	−177.4 (3)	C15—C12—C13—O1	178.7 (3)
C1—C2—C7—C8	2.1 (4)	C11—C12—C13—O1	−2.7 (5)
C3—C2—C7—C6	2.8 (4)	C1—O1—C13—N1	165.0 (3)
C1—C2—C7—C6	−177.7 (3)	C1—O1—C13—C12	−14.4 (4)
C5—C6—C7—C2	−3.7 (5)	C12—C11—C16—C17	56.2 (4)
C5—C6—C7—C8	176.6 (3)	C10—C11—C16—C17	−66.6 (4)
C14—O2—C8—C9	−2.8 (5)	C12—C11—C16—C21	−124.5 (3)
C14—O2—C8—C7	177.4 (3)	C10—C11—C16—C21	112.6 (4)
C2—C7—C8—C9	1.1 (5)	C21—C16—C17—C18	−2.2 (6)
C6—C7—C8—C9	−179.1 (3)	C11—C16—C17—C18	177.0 (3)
C2—C7—C8—O2	−179.0 (3)	C16—C17—C18—C19	0.7 (6)
C6—C7—C8—O2	0.7 (4)	C17—C18—C19—C20	1.3 (6)
O2—C8—C9—C10	177.5 (3)	C17—C18—C19—Br1	−179.9 (3)
C7—C8—C9—C10	−2.6 (5)	C18—C19—C20—C21	−1.7 (6)
O1—C1—C10—C9	−177.2 (3)	Br1—C19—C20—C21	179.6 (3)
C2—C1—C10—C9	2.7 (5)	C17—C16—C21—C20	1.9 (5)
O1—C1—C10—C11	2.3 (5)	C11—C16—C21—C20	−177.3 (3)
C2—C1—C10—C11	−177.8 (3)	C19—C20—C21—C16	0.0 (6)
C8—C9—C10—C1	0.7 (5)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2ⁱ	0.88 (1)	2.22 (2)	3.059 (5)	159 (4)
N1—H2···O2ⁱⁱ	0.87 (3)	2.56 (5)	3.324 (4)	147 (4)
C18—H18···Cg1ⁱⁱⁱ	0.93	2.87	3.528 (4)	129

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₅BrN₂O₂
M_r	407.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	6.0823 (7), 16.6918 (18), 17.7700 (16)
β (°)	93.646 (9)
V (Å³)	1800.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.30
Crystal size (mm)	0.30 × 0.10 × 0.10

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.694, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8976, 4144, 2250
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.150, 1.03
No. of reflections	4144
No. of parameters	243
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.71, −0.78

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2ⁱ	0.877 (10)	2.22 (2)	3.059 (5)	159 (4)
N1—H2···O2ⁱⁱ	0.87 (3)	2.56 (5)	3.324 (4)	147 (4)
C18—H18···Cg1ⁱⁱⁱ	0.93	2.87	3.528 (4)	129

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

Footnotes

‡Additional correspondence author, e-mail: aamr1963@yahoo.com.

Acknowledgements

The authors extend their appreciation to the Deanship of Scientific Research at King Saud University for funding this work through the research group project No. RGP-VPP-099. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).

References

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Volume 69| Part 4| April 2013| Pages o480-o481

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