[3-Benzoyl-2,4-bis­(3-bromo­phen­yl)cyclo­butyl](phen­yl)methanone

Mol­ecules of the title compound, C₃₀H₂₂Br₂O₂, lie across crystallographic inversion centres. The dihedral angle between the phenyl and bromo­benzene rings is 23.88 (8)°. Weak C—H...O inter­actions link the mol­ecules into ribbons along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.026
• wR factor = 0.062
• Data-to-parameter ratio = 20.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9     ..  O1      ..       2.61 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

[3-Benzoyl-2,4-bis(3-bromophenyl)cyclobutyl](phenyl)methanone

Crystal data

C30H22Br2O2	F(000) = 576
Mr = 574.28	Dx = 1.615 Mg m^−3
Monoclinic, P21/c	Melting point = 337–338 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.7813 (1) Å	Cell parameters from 3429 reflections
b = 14.6794 (2) Å	θ = 2.8–30.0°
c = 14.2828 (2) Å	µ = 3.46 mm^−1
β = 102.988 (1)°	T = 100 K
V = 1181.11 (3) Å^3	Block, colourless
Z = 2	0.46 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	3429 independent reflections
Radiation source: fine-focus sealed tube	2869 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 8.33 pixels mm^-1	θmax = 30.0°, θmin = 2.8°
ω scans	h = −8→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −20→20
Tmin = 0.300, Tmax = 0.737	l = −18→20
18746 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.062	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0261P)^2 + 0.7106P] where P = (Fo^2 + 2Fc^2)/3
3429 reflections	(Δ/σ)max = 0.003
165 parameters	Δρmax = 0.55 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1A	0.95743 (3)	0.677394 (12)	0.090265 (11)	0.02250 (6)
O1	1.46944 (19)	0.58511 (9)	0.58587 (8)	0.0194 (2)
C1	1.0989 (3)	0.61914 (11)	0.75297 (11)	0.0161 (3)
H1	0.9565	0.6359	0.7104	0.024 (5)*
C2	1.1158 (3)	0.62929 (12)	0.85149 (12)	0.0199 (3)
H2	0.9925	0.6547	0.8728	0.017 (5)*
C3	1.3218 (3)	0.60353 (13)	0.91637 (12)	0.0221 (4)
H3	1.3315	0.6099	0.9819	0.030 (6)*
C4	1.5126 (3)	0.56867 (12)	0.88346 (12)	0.0205 (3)
H4	1.6516	0.5506	0.9263	0.025 (5)*
C5	1.4993 (3)	0.56172 (11)	0.78581 (12)	0.0169 (3)
H5	1.6252	0.5400	0.7630	0.016 (5)*
C6	1.2925 (3)	0.58670 (10)	0.71972 (11)	0.0137 (3)
C7	1.2873 (3)	0.57827 (10)	0.61493 (11)	0.0139 (3)
C8	1.0498 (3)	0.55832 (10)	0.54807 (10)	0.0124 (3)
H8	0.9455	0.6015	0.5581	0.013 (4)*
C9	1.0544 (3)	0.54013 (11)	0.44219 (10)	0.0124 (3)
H9	1.2145	0.5363	0.4339	0.012 (4)*
C10	0.9128 (3)	0.60158 (10)	0.36589 (11)	0.0131 (3)
C11	0.9880 (3)	0.61289 (10)	0.28015 (11)	0.0137 (3)
H11	1.1279	0.5846	0.2724	0.012 (4)*
C12	0.8518 (3)	0.66377 (11)	0.20650 (11)	0.0155 (3)
C13	0.6432 (3)	0.70614 (11)	0.21493 (12)	0.0176 (3)
H13	0.5599	0.7401	0.1639	0.027 (6)*
C14	0.5706 (3)	0.69579 (11)	0.30056 (12)	0.0180 (3)
H14	0.4260	0.7247	0.3077	0.018 (5)*
C15	0.7020 (3)	0.64359 (11)	0.37522 (11)	0.0158 (3)
H15	0.6477	0.6377	0.4286	0.013 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1A	0.02993 (10)	0.02507 (10)	0.01326 (8)	−0.00070 (7)	0.00649 (6)	0.00173 (7)
O1	0.0152 (5)	0.0243 (6)	0.0195 (6)	−0.0024 (5)	0.0058 (4)	−0.0037 (5)
C1	0.0143 (7)	0.0175 (8)	0.0161 (7)	−0.0010 (6)	0.0025 (6)	−0.0008 (6)
C2	0.0190 (8)	0.0246 (9)	0.0179 (8)	−0.0009 (7)	0.0077 (6)	−0.0017 (7)
C3	0.0259 (8)	0.0268 (9)	0.0133 (7)	−0.0054 (7)	0.0035 (6)	0.0005 (7)
C4	0.0183 (8)	0.0228 (9)	0.0178 (8)	−0.0011 (7)	−0.0015 (6)	0.0025 (6)
C5	0.0141 (7)	0.0168 (8)	0.0194 (8)	−0.0004 (6)	0.0030 (6)	−0.0001 (6)
C6	0.0139 (7)	0.0115 (7)	0.0156 (7)	−0.0016 (6)	0.0029 (6)	−0.0017 (6)
C7	0.0155 (7)	0.0104 (7)	0.0154 (7)	0.0005 (6)	0.0028 (6)	−0.0009 (6)
C8	0.0130 (7)	0.0120 (7)	0.0122 (7)	0.0004 (5)	0.0030 (5)	−0.0004 (5)
C9	0.0123 (6)	0.0138 (7)	0.0114 (6)	−0.0001 (6)	0.0029 (5)	−0.0002 (5)
C10	0.0142 (7)	0.0111 (7)	0.0132 (7)	−0.0012 (6)	0.0014 (5)	−0.0007 (5)
C11	0.0143 (7)	0.0117 (7)	0.0152 (7)	−0.0003 (6)	0.0032 (6)	−0.0016 (6)
C12	0.0193 (7)	0.0155 (8)	0.0115 (7)	−0.0026 (6)	0.0030 (6)	−0.0002 (6)
C13	0.0178 (7)	0.0145 (7)	0.0184 (8)	0.0009 (6)	−0.0002 (6)	0.0028 (6)
C14	0.0144 (7)	0.0156 (8)	0.0235 (8)	0.0014 (6)	0.0035 (6)	0.0001 (6)
C15	0.0156 (7)	0.0166 (7)	0.0160 (7)	−0.0005 (6)	0.0052 (6)	0.0003 (6)

Geometric parameters (Å, º)

Br1A—C12	1.9039 (16)	C8—C9^i	1.584 (2)
O1—C7	1.2199 (19)	C8—H8	0.9083
C1—C6	1.394 (2)	C9—C10	1.507 (2)
C1—C2	1.396 (2)	C9—C8^i	1.584 (2)
C1—H1	0.9397	C9—H9	0.9607
C2—C3	1.387 (2)	C10—C11	1.398 (2)
C2—H2	0.9148	C10—C15	1.399 (2)
C3—C4	1.390 (3)	C11—C12	1.383 (2)
C3—H3	0.9295	C11—H11	0.9377
C4—C5	1.383 (2)	C12—C13	1.386 (2)
C4—H4	0.9324	C13—C14	1.388 (2)
C5—C6	1.396 (2)	C13—H13	0.9237
C5—H5	0.9188	C14—C15	1.392 (2)
C6—C7	1.495 (2)	C14—H14	0.9632
C7—C8	1.514 (2)	C15—H15	0.8912
C8—C9	1.542 (2)
C6—C1—C2	119.99 (15)	C9^i—C8—H8	110.1
C6—C1—H1	121.5	C10—C9—C8	118.63 (13)
C2—C1—H1	118.5	C10—C9—C8^i	117.01 (12)
C3—C2—C1	119.95 (16)	C8—C9—C8^i	88.91 (11)
C3—C2—H2	120.4	C10—C9—H9	109.1
C1—C2—H2	119.7	C8—C9—H9	111.2
C2—C3—C4	120.12 (15)	C8^i—C9—H9	110.7
C2—C3—H3	119.6	C11—C10—C15	118.69 (14)
C4—C3—H3	120.3	C11—C10—C9	118.63 (13)
C5—C4—C3	119.97 (15)	C15—C10—C9	122.58 (14)
C5—C4—H4	119.0	C12—C11—C10	119.62 (14)
C3—C4—H4	121.0	C12—C11—H11	120.6
C4—C5—C6	120.50 (15)	C10—C11—H11	119.8
C4—C5—H5	120.9	C11—C12—C13	122.29 (15)
C6—C5—H5	118.6	C11—C12—Br1A	118.72 (12)
C1—C6—C5	119.39 (14)	C13—C12—Br1A	118.98 (12)
C1—C6—C7	122.14 (14)	C12—C13—C14	117.95 (15)
C5—C6—C7	118.47 (14)	C12—C13—H13	118.9
O1—C7—C6	120.59 (14)	C14—C13—H13	123.1
O1—C7—C8	122.08 (14)	C13—C14—C15	120.97 (15)
C6—C7—C8	117.30 (13)	C13—C14—H14	119.1
C7—C8—C9	116.02 (12)	C15—C14—H14	119.9
C7—C8—C9^i	115.46 (12)	C14—C15—C10	120.46 (15)
C9—C8—C9^i	91.09 (11)	C14—C15—H15	118.2
C7—C8—H8	107.8	C10—C15—H15	121.4
C9—C8—H8	115.7
C6—C1—C2—C3	−2.7 (3)	C9^i—C8—C9—C10	120.48 (15)
C1—C2—C3—C4	0.8 (3)	C7—C8—C9—C8^i	119.19 (15)
C2—C3—C4—C5	1.6 (3)	C9^i—C8—C9—C8^i	0.0
C3—C4—C5—C6	−2.1 (3)	C8—C9—C10—C11	152.96 (14)
C2—C1—C6—C5	2.2 (2)	C8^i—C9—C10—C11	−102.33 (16)
C2—C1—C6—C7	−177.37 (15)	C8—C9—C10—C15	−30.8 (2)
C4—C5—C6—C1	0.2 (2)	C8^i—C9—C10—C15	73.96 (19)
C4—C5—C6—C7	179.77 (15)	C15—C10—C11—C12	−1.0 (2)
C1—C6—C7—O1	151.02 (16)	C9—C10—C11—C12	175.47 (14)
C5—C6—C7—O1	−28.5 (2)	C10—C11—C12—C13	1.3 (2)
C1—C6—C7—C8	−30.7 (2)	C10—C11—C12—Br1A	−179.60 (11)
C5—C6—C7—C8	149.72 (15)	C11—C12—C13—C14	−0.5 (2)
O1—C7—C8—C9	4.3 (2)	Br1A—C12—C13—C14	−179.55 (12)
C6—C7—C8—C9	−173.86 (13)	C12—C13—C14—C15	−0.7 (2)
O1—C7—C8—C9^i	109.17 (17)	C13—C14—C15—C10	1.0 (2)
C6—C7—C8—C9^i	−69.03 (17)	C11—C10—C15—C14	−0.2 (2)
C7—C8—C9—C10	−120.33 (15)	C9—C10—C15—C14	−176.48 (15)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1^ii	0.96	2.61	3.408 (2)	140
C2—H2···Cg3^iii	0.93	3.19	3.7323 (19)	120
C14—H14···Cg2^iv	0.96	2.75	3.4655 (18)	132

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