(9R,10R,10aR)-9-(2-Bromo­phen­yl)-10-nitro-6-phenyl-10,10a-dihydro-9H-benzo[c]chromene-8-carbaldehyde

Dufour, J.; Maji, M.S.; Bolte, M.

doi:10.1107/S160053681103995X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2844

doi:10.1107/S160053681103995X

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(9R,10R,10aR)-9-(2-Bromophenyl)-10-nitro-6-phenyl-10,10a-dihydro-9H-benzo[c]chromene-8-carbaldehyde

Jeremy Dufour,^a Modhu Sudan Maji ^a and Michael Bolte ^b ^*

^aInstitute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany, and ^bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: bolte@chemie.uni-frankfurt.de

(Received 21 September 2011; accepted 28 September 2011; online 5 October 2011)

The title compound, C₂₆H₁₈BrNO₄, features a functionalized chromene. The cyclohexene ring adopts a sofa conformation and has the nitro group and the bromophenyl ring in an axial position. The ten atoms of the chromene moiety lie close to a common plane (r.m.s. deviation = 0.066 Å). The attached phenyl ring is twisted by 32.89 (10)° from the chromene plane. The crystal packing is stabilized by C—H⋯O interactions.

Related literature

For functionalized chromenes, see: Ellis & Lockhart (2007 ). For the synthesis of the title compound, see: Rueping et al. (2011 ).

Experimental

Crystal data

C₂₆H₁₈BrNO₄
M_r = 488.32
Monoclinic, P 2₁
a = 7.1583 (8) Å
b = 13.2036 (12) Å
c = 11.2510 (14) Å
β = 90.642 (9)°
V = 1063.3 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.97 mm⁻¹
T = 173 K
0.36 × 0.35 × 0.19 mm

Data collection

Stoe IPDS II two-circle diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2009 ; Blessing, 1995 ) T_min = 0.538, T_max = 0.706
6069 measured reflections
3778 independent reflections
3443 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.087
S = 1.00
3778 reflections
290 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.60 e Å⁻³
Absolute structure: Flack (1983 ), 1700 Friedel pairs
Flack parameter: −0.003 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O15ⁱ	1.00	2.34	3.266 (4)	154
C7—H7⋯O15ⁱⁱ	0.95	2.55	3.487 (5)	168
C25—H25⋯O15ⁱⁱⁱ	0.95	2.45	3.314 (4)	151
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+1]$ ; (iii) x, y, z-1.

Data collection: X-AREA (Stoe & Cie, 2001 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681103995X/qm2032sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681103995X/qm2032Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681103995X/qm2032Isup3.cml

checkCIF report

Comment top

Functionalized chromenes are important compounds due to their biological activity. They find wide application in medicinal chemistry and have shown to display spasmolytic, diuretic, clotting, antiviral, anti-tumoral and anti-anaphylactic activity. Additionally, they can be used as pigments, photo-active materials and biodegradable agrochemicals. Furthermore, chromenes are components of numerous natural products (Ellis & Lockhart, 2007). The title compound was prepared following two new consecutive domino reactions starting from readily available propargylic alcohols, nitro-styrenes and α,β-unsaturated aldehydes.

The title compound features a functionalized chromene. The cyclohexene ring adopts a sofa conformation and has the nitro group and the bromophenyl ring in an axial position. The ten atoms of the chromene moiety lie in a common plane (r.m.s. deviation 0.066 Å). The attached phenyl ring is twisted by 32.89 (10)° from the chromene plane. The crystal packing is stabilized by C—H···O interactions.

Related literature top

For functionalized chromenes, see: Ellis & Lockhart (2007). For the synthesis of the title compound, see: Rueping et al. (2011).

Experimental top

The title compound has been synthesized as described by Rueping et al. (2011).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level.

(9R,10R,10aR)-9-(2-Bromophenyl)-10-nitro-6-phenyl- 10,10a-dihydro-9H-benzo[c]chromene-8-carbaldehyde top

Crystal data top

C₂₆H₁₈BrNO₄	F(000) = 496
M_r = 488.32	D_x = 1.525 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5380 reflections
a = 7.1583 (8) Å	θ = 3.6–25.9°
b = 13.2036 (12) Å	µ = 1.97 mm⁻¹
c = 11.2510 (14) Å	T = 173 K
β = 90.642 (9)°	Plate, yellow
V = 1063.3 (2) Å³	0.36 × 0.35 × 0.19 mm
Z = 2

Data collection top

Stoe IPDS II two-circle diffractometer	3778 independent reflections
Radiation source: fine-focus sealed tube	3443 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 25.6°, θ_min = 3.6°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −8→8
T_min = 0.538, T_max = 0.706	k = −16→16
6069 measured reflections	l = −11→13

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.036	w = 1/[σ²(F_o²) + (0.0608P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.087	(Δ/σ)_max = 0.001
S = 1.00	Δρ_max = 0.59 e Å⁻³
3778 reflections	Δρ_min = −0.60 e Å⁻³
290 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.021 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1700 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.003 (8)

Crystal data top

C₂₆H₁₈BrNO₄	V = 1063.3 (2) Å³
M_r = 488.32	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.1583 (8) Å	µ = 1.97 mm⁻¹
b = 13.2036 (12) Å	T = 173 K
c = 11.2510 (14) Å	0.36 × 0.35 × 0.19 mm
β = 90.642 (9)°

Data collection top

Stoe IPDS II two-circle diffractometer	3778 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	3443 reflections with I > 2σ(I)
T_min = 0.538, T_max = 0.706	R_int = 0.034
6069 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.087	Δρ_max = 0.59 e Å⁻³
S = 1.00	Δρ_min = −0.60 e Å⁻³
3778 reflections	Absolute structure: Flack (1983), 1700 Friedel pairs
290 parameters	Absolute structure parameter: −0.003 (8)
1 restraint

Special details top

Experimental. ;

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	0.10708 (4)	0.57378 (3)	0.75261 (3)	0.04064 (14)
O1	0.2792 (3)	0.61771 (19)	0.0890 (2)	0.0276 (5)
C2	0.4038 (4)	0.5584 (2)	0.1524 (3)	0.0227 (6)
C3	0.3955 (4)	0.5501 (2)	0.2723 (3)	0.0231 (7)
C4	0.2625 (4)	0.6123 (2)	0.3462 (3)	0.0222 (6)
H4	0.3374	0.6693	0.3808	0.027*
C5	0.1122 (4)	0.6604 (2)	0.2682 (3)	0.0240 (7)
C6	−0.0442 (5)	0.7082 (3)	0.3160 (4)	0.0295 (8)
H6	−0.0573	0.7119	0.3998	0.035*
C7	−0.1813 (5)	0.7506 (3)	0.2423 (4)	0.0360 (8)
H7	−0.2868	0.7830	0.2760	0.043*
C8	−0.1636 (5)	0.7455 (3)	0.1208 (4)	0.0348 (8)
H8	−0.2588	0.7729	0.0709	0.042*
C9	−0.0093 (5)	0.7010 (3)	0.0707 (3)	0.0299 (7)
H9	0.0040	0.6986	−0.0131	0.036*
C10	0.1272 (5)	0.6595 (2)	0.1459 (3)	0.0246 (7)
C11	0.5043 (4)	0.4747 (2)	0.3365 (3)	0.0227 (6)
H11	0.5940	0.4370	0.2934	0.027*
C12	0.4863 (4)	0.4550 (2)	0.4530 (3)	0.0237 (7)
C13	0.3483 (4)	0.5097 (3)	0.5309 (3)	0.0234 (7)
H13	0.2916	0.4581	0.5847	0.028*
C14	0.1891 (4)	0.5519 (2)	0.4502 (3)	0.0251 (7)
H14	0.1088	0.5973	0.4991	0.030*
N14	0.0711 (4)	0.4609 (3)	0.4096 (3)	0.0340 (7)
O141	0.0475 (4)	0.4442 (2)	0.3057 (3)	0.0426 (7)
O142	0.0106 (6)	0.4048 (4)	0.4866 (4)	0.0808 (14)
C15	0.5881 (5)	0.3690 (2)	0.5044 (3)	0.0261 (7)
H15	0.6739	0.3343	0.4551	0.031*
O15	0.5706 (4)	0.33907 (19)	0.6056 (2)	0.0329 (6)
C21	0.5311 (4)	0.5078 (2)	0.0706 (3)	0.0233 (7)
C22	0.7220 (5)	0.4978 (3)	0.0954 (3)	0.0286 (7)
H22	0.7722	0.5223	0.1684	0.034*
C23	0.8374 (5)	0.4526 (3)	0.0140 (4)	0.0368 (8)
H23	0.9667	0.4448	0.0318	0.044*
C24	0.7662 (5)	0.4180 (3)	−0.0946 (3)	0.0341 (8)
H24	0.8465	0.3878	−0.1511	0.041*
C25	0.5773 (5)	0.4282 (3)	−0.1190 (3)	0.0333 (8)
H25	0.5278	0.4044	−0.1926	0.040*
C26	0.4612 (5)	0.4722 (3)	−0.0384 (3)	0.0283 (7)
H26	0.3319	0.4788	−0.0565	0.034*
C31	0.4333 (4)	0.5917 (2)	0.6090 (3)	0.0235 (7)
C32	0.3449 (5)	0.6269 (3)	0.7118 (3)	0.0311 (7)
C33	0.4251 (6)	0.6979 (3)	0.7875 (3)	0.0379 (9)
H33	0.3617	0.7194	0.8569	0.046*
C34	0.5987 (6)	0.7368 (3)	0.7604 (4)	0.0415 (10)
H34	0.6563	0.7848	0.8120	0.050*
C35	0.6882 (6)	0.7064 (3)	0.6592 (4)	0.0362 (8)
H35	0.8062	0.7345	0.6399	0.043*
C36	0.6062 (5)	0.6344 (3)	0.5846 (3)	0.0295 (7)
H36	0.6703	0.6138	0.5152	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03347 (18)	0.0590 (2)	0.02960 (18)	0.0109 (2)	0.00755 (12)	0.0032 (2)
O1	0.0266 (11)	0.0314 (11)	0.0249 (12)	0.0089 (9)	0.0029 (9)	0.0033 (10)
C2	0.0192 (13)	0.0208 (17)	0.0281 (15)	0.0000 (12)	−0.0017 (11)	0.0022 (14)
C3	0.0187 (13)	0.0227 (19)	0.0279 (16)	0.0003 (11)	−0.0009 (12)	−0.0020 (12)
C4	0.0207 (14)	0.0209 (14)	0.0248 (16)	0.0016 (11)	−0.0025 (12)	−0.0020 (12)
C5	0.0245 (16)	0.0178 (14)	0.0296 (18)	0.0003 (12)	0.0014 (14)	−0.0013 (13)
C6	0.0309 (18)	0.0262 (17)	0.0315 (19)	0.0088 (14)	0.0010 (16)	−0.0020 (14)
C7	0.0290 (17)	0.0307 (18)	0.048 (2)	0.0116 (15)	0.0011 (16)	0.0000 (16)
C8	0.0317 (18)	0.0312 (18)	0.041 (2)	0.0104 (16)	−0.0047 (16)	0.0036 (16)
C9	0.0307 (17)	0.0264 (17)	0.0324 (19)	0.0023 (14)	−0.0041 (14)	0.0029 (14)
C10	0.0232 (15)	0.0189 (15)	0.0317 (18)	0.0020 (12)	−0.0009 (13)	0.0000 (13)
C11	0.0157 (13)	0.0228 (15)	0.0297 (18)	−0.0001 (12)	−0.0018 (12)	−0.0021 (13)
C12	0.0187 (14)	0.0226 (15)	0.0296 (17)	0.0011 (12)	−0.0008 (13)	−0.0019 (13)
C13	0.0204 (15)	0.0282 (16)	0.0218 (16)	0.0021 (12)	−0.0004 (12)	0.0000 (13)
C14	0.0187 (13)	0.030 (2)	0.0268 (15)	0.0019 (12)	−0.0004 (11)	−0.0008 (13)
N14	0.0192 (13)	0.0451 (18)	0.0375 (18)	−0.0102 (13)	−0.0045 (13)	0.0108 (15)
O141	0.0450 (16)	0.0380 (15)	0.0445 (18)	−0.0127 (13)	−0.0067 (15)	−0.0049 (13)
O142	0.077 (3)	0.105 (3)	0.060 (2)	−0.062 (2)	−0.013 (2)	0.030 (2)
C15	0.0223 (15)	0.0235 (16)	0.0324 (19)	0.0020 (12)	−0.0031 (13)	−0.0030 (14)
O15	0.0415 (14)	0.0308 (12)	0.0264 (14)	0.0070 (11)	0.0000 (11)	0.0040 (10)
C21	0.0254 (16)	0.0184 (15)	0.0260 (16)	0.0008 (12)	0.0010 (13)	0.0007 (13)
C22	0.0247 (16)	0.0304 (17)	0.0306 (18)	−0.0027 (13)	0.0010 (13)	−0.0031 (14)
C23	0.0259 (17)	0.0379 (19)	0.047 (2)	0.0003 (15)	0.0061 (16)	−0.0034 (17)
C24	0.0381 (19)	0.0295 (17)	0.035 (2)	0.0041 (15)	0.0103 (16)	−0.0060 (16)
C25	0.043 (2)	0.0305 (19)	0.0262 (18)	0.0017 (16)	−0.0006 (16)	−0.0034 (14)
C26	0.0260 (16)	0.0315 (18)	0.0273 (17)	0.0003 (14)	−0.0022 (13)	0.0011 (14)
C31	0.0249 (13)	0.0236 (19)	0.0219 (14)	0.0060 (12)	−0.0040 (11)	0.0024 (13)
C32	0.0339 (17)	0.0328 (18)	0.0266 (17)	0.0082 (15)	−0.0032 (14)	0.0022 (15)
C33	0.055 (2)	0.034 (2)	0.0239 (18)	0.0143 (18)	−0.0043 (16)	−0.0057 (15)
C34	0.055 (2)	0.0288 (18)	0.040 (2)	0.0041 (18)	−0.0176 (19)	−0.0057 (17)
C35	0.0363 (19)	0.0274 (17)	0.044 (2)	−0.0001 (15)	−0.0141 (17)	−0.0030 (16)
C36	0.0270 (16)	0.0294 (18)	0.0321 (19)	0.0024 (14)	−0.0041 (14)	−0.0004 (15)

Geometric parameters (Å, º) top

Br1—C32	1.902 (4)	C14—N14	1.534 (4)
O1—C2	1.379 (4)	C14—H14	1.0000
O1—C10	1.383 (4)	N14—O141	1.201 (4)
C2—C3	1.356 (4)	N14—O142	1.223 (5)
C2—C21	1.464 (4)	C15—O15	1.213 (4)
C3—C11	1.451 (4)	C15—H15	0.9500
C3—C4	1.514 (4)	C21—C22	1.398 (5)
C4—C14	1.515 (5)	C21—C26	1.401 (5)
C4—C5	1.520 (4)	C22—C23	1.377 (5)
C4—H4	1.0000	C22—H22	0.9500
C5—C10	1.382 (5)	C23—C24	1.395 (6)
C5—C6	1.398 (5)	C23—H23	0.9500
C6—C7	1.394 (5)	C24—C25	1.383 (5)
C6—H6	0.9500	C24—H24	0.9500
C7—C8	1.377 (6)	C25—C26	1.367 (5)
C7—H7	0.9500	C25—H25	0.9500
C8—C9	1.377 (5)	C26—H26	0.9500
C8—H8	0.9500	C31—C36	1.390 (5)
C9—C10	1.397 (5)	C31—C32	1.404 (5)
C9—H9	0.9500	C32—C33	1.387 (6)
C11—C12	1.345 (5)	C33—C34	1.383 (6)
C11—H11	0.9500	C33—H33	0.9500
C12—C15	1.465 (5)	C34—C35	1.373 (6)
C12—C13	1.511 (4)	C34—H34	0.9500
C13—C31	1.517 (4)	C35—C36	1.393 (5)
C13—C14	1.553 (4)	C35—H35	0.9500
C13—H13	1.0000	C36—H36	0.9500

C2—O1—C10	119.6 (3)	C4—C14—H14	108.4
C3—C2—O1	121.7 (3)	N14—C14—H14	108.4
C3—C2—C21	128.5 (3)	C13—C14—H14	108.4
O1—C2—C21	109.7 (3)	O141—N14—O142	122.1 (3)
C2—C3—C11	121.5 (3)	O141—N14—C14	120.3 (3)
C2—C3—C4	122.5 (3)	O142—N14—C14	117.5 (3)
C11—C3—C4	115.9 (3)	O15—C15—C12	124.6 (3)
C3—C4—C14	111.3 (3)	O15—C15—H15	117.7
C3—C4—C5	110.8 (3)	C12—C15—H15	117.7
C14—C4—C5	114.6 (3)	C22—C21—C26	118.8 (3)
C3—C4—H4	106.5	C22—C21—C2	122.2 (3)
C14—C4—H4	106.5	C26—C21—C2	119.0 (3)
C5—C4—H4	106.5	C23—C22—C21	120.1 (3)
C10—C5—C6	117.3 (3)	C23—C22—H22	120.0
C10—C5—C4	120.6 (3)	C21—C22—H22	120.0
C6—C5—C4	122.1 (3)	C22—C23—C24	120.5 (3)
C7—C6—C5	121.0 (4)	C22—C23—H23	119.7
C7—C6—H6	119.5	C24—C23—H23	119.7
C5—C6—H6	119.5	C25—C24—C23	119.3 (3)
C8—C7—C6	119.9 (3)	C25—C24—H24	120.3
C8—C7—H7	120.1	C23—C24—H24	120.3
C6—C7—H7	120.1	C26—C25—C24	120.6 (3)
C9—C8—C7	120.7 (3)	C26—C25—H25	119.7
C9—C8—H8	119.7	C24—C25—H25	119.7
C7—C8—H8	119.7	C25—C26—C21	120.7 (3)
C8—C9—C10	118.6 (3)	C25—C26—H26	119.7
C8—C9—H9	120.7	C21—C26—H26	119.7
C10—C9—H9	120.7	C36—C31—C32	116.0 (3)
C5—C10—O1	122.3 (3)	C36—C31—C13	121.8 (3)
C5—C10—C9	122.5 (3)	C32—C31—C13	122.1 (3)
O1—C10—C9	115.1 (3)	C33—C32—C31	122.9 (4)
C12—C11—C3	124.1 (3)	C33—C32—Br1	117.8 (3)
C12—C11—H11	117.9	C31—C32—Br1	119.3 (3)
C3—C11—H11	117.9	C34—C33—C32	118.9 (4)
C11—C12—C15	118.9 (3)	C34—C33—H33	120.6
C11—C12—C13	122.9 (3)	C32—C33—H33	120.6
C15—C12—C13	117.8 (3)	C35—C34—C33	120.2 (4)
C12—C13—C31	114.6 (3)	C35—C34—H34	119.9
C12—C13—C14	108.2 (3)	C33—C34—H34	119.9
C31—C13—C14	111.7 (3)	C34—C35—C36	120.1 (4)
C12—C13—H13	107.4	C34—C35—H35	119.9
C31—C13—H13	107.4	C36—C35—H35	119.9
C14—C13—H13	107.4	C31—C36—C35	121.9 (3)
C4—C14—N14	112.2 (3)	C31—C36—H36	119.1
C4—C14—C13	112.5 (3)	C35—C36—H36	119.1
N14—C14—C13	106.9 (3)

C10—O1—C2—C3	−8.5 (4)	C5—C4—C14—C13	−176.7 (3)
C10—O1—C2—C21	169.5 (3)	C12—C13—C14—C4	−51.2 (3)
O1—C2—C3—C11	169.1 (3)	C31—C13—C14—C4	75.8 (3)
C21—C2—C3—C11	−8.6 (5)	C12—C13—C14—N14	72.3 (3)
O1—C2—C3—C4	−6.0 (5)	C31—C13—C14—N14	−160.7 (3)
C21—C2—C3—C4	176.3 (3)	C4—C14—N14—O141	0.6 (4)
C2—C3—C4—C14	143.9 (3)	C13—C14—N14—O141	−123.1 (3)
C11—C3—C4—C14	−31.4 (4)	C4—C14—N14—O142	177.4 (4)
C2—C3—C4—C5	15.1 (4)	C13—C14—N14—O142	53.7 (5)
C11—C3—C4—C5	−160.2 (3)	C11—C12—C15—O15	−173.6 (3)
C3—C4—C5—C10	−11.3 (4)	C13—C12—C15—O15	−0.6 (5)
C14—C4—C5—C10	−138.3 (3)	C3—C2—C21—C22	−43.0 (5)
C3—C4—C5—C6	169.7 (3)	O1—C2—C21—C22	139.1 (3)
C14—C4—C5—C6	42.7 (4)	C3—C2—C21—C26	139.9 (3)
C10—C5—C6—C7	1.7 (5)	O1—C2—C21—C26	−38.0 (4)
C4—C5—C6—C7	−179.2 (3)	C26—C21—C22—C23	−0.8 (5)
C5—C6—C7—C8	0.1 (6)	C2—C21—C22—C23	−177.9 (3)
C6—C7—C8—C9	−1.6 (6)	C21—C22—C23—C24	1.2 (6)
C7—C8—C9—C10	1.2 (6)	C22—C23—C24—C25	−1.0 (6)
C6—C5—C10—O1	177.6 (3)	C23—C24—C25—C26	0.4 (6)
C4—C5—C10—O1	−1.5 (5)	C24—C25—C26—C21	0.0 (5)
C6—C5—C10—C9	−2.2 (5)	C22—C21—C26—C25	0.2 (5)
C4—C5—C10—C9	178.7 (3)	C2—C21—C26—C25	177.4 (3)
C2—O1—C10—C5	12.3 (5)	C12—C13—C31—C36	19.3 (4)
C2—O1—C10—C9	−167.9 (3)	C14—C13—C31—C36	−104.2 (3)
C8—C9—C10—C5	0.8 (5)	C12—C13—C31—C32	−158.9 (3)
C8—C9—C10—O1	−179.0 (3)	C14—C13—C31—C32	77.7 (4)
C2—C3—C11—C12	−172.0 (3)	C36—C31—C32—C33	−1.8 (5)
C4—C3—C11—C12	3.3 (4)	C13—C31—C32—C33	176.5 (3)
C3—C11—C12—C15	172.8 (3)	C36—C31—C32—Br1	179.7 (2)
C3—C11—C12—C13	0.2 (5)	C13—C31—C32—Br1	−2.1 (4)
C11—C12—C13—C31	−101.9 (4)	C31—C32—C33—C34	0.8 (6)
C15—C12—C13—C31	85.4 (4)	Br1—C32—C33—C34	179.3 (3)
C11—C12—C13—C14	23.4 (4)	C32—C33—C34—C35	0.9 (6)
C15—C12—C13—C14	−149.3 (3)	C33—C34—C35—C36	−1.4 (6)
C3—C4—C14—N14	−64.0 (3)	C32—C31—C36—C35	1.2 (5)
C5—C4—C14—N14	62.7 (3)	C13—C31—C36—C35	−177.1 (3)
C3—C4—C14—C13	56.5 (3)	C34—C35—C36—C31	0.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O15ⁱ	1.00	2.34	3.266 (4)	154
C7—H7···O15ⁱⁱ	0.95	2.55	3.487 (5)	168
C25—H25···O15ⁱⁱⁱ	0.95	2.45	3.314 (4)	151

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

Experimental details

Crystal data
Chemical formula	C₂₆H₁₈BrNO₄
M_r	488.32
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	173
a, b, c (Å)	7.1583 (8), 13.2036 (12), 11.2510 (14)
β (°)	90.642 (9)
V (Å³)	1063.3 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.97
Crystal size (mm)	0.36 × 0.35 × 0.19

Data collection
Diffractometer	Stoe IPDS II two-circle diffractometer
Absorption correction	Multi-scan (MULABS; Spek, 2009; Blessing, 1995)
T_min, T_max	0.538, 0.706
No. of measured, independent and observed [I > 2σ(I)] reflections	6069, 3778, 3443
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.608

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.087, 1.00
No. of reflections	3778
No. of parameters	290
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.60
Absolute structure	Flack (1983), 1700 Friedel pairs
Absolute structure parameter	−0.003 (8)

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O15ⁱ	1.00	2.34	3.266 (4)	153.5
C7—H7···O15ⁱⁱ	0.95	2.55	3.487 (5)	168.4
C25—H25···O15ⁱⁱⁱ	0.95	2.45	3.314 (4)	150.9

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

References

Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Ellis, G. P. & Lockhart, I. M. (2007). The Chemistry of Heterocyclic Compounds, Chromenes, Chromanones, and Chromones, Vol. 31, edited by G. P. Ellis, pp. 1–1196. London: Wiley-VCH. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Rueping, M., Dufour, J. & Maji, M. S. (2011). In preparation. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar

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Volume 67| Part 11| November 2011| Page o2844

doi:10.1107/S160053681103995X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(9R,10R,10aR)-9-(2-Bromo­phen­yl)-10-nitro-6-phenyl-10,10a-di­hydro-9H-benzo[c]chromene-8-carbaldehyde

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

(9R,10R,10aR)-9-(2-Bromophenyl)-10-nitro-6-phenyl-10,10a-dihydro-9H-benzo[c]chromene-8-carbaldehyde