2,7-Dibromo-9,9-bis­(4-hydroxy­phen­yl)-9H-fluorene

In the solid state, the title compound, C₂₅H₁₆Br₂O₂, shows significant deviations of the fluorene ring system from planarity. A layered hydrogen-bonded structure is formed that may serve as a model for the solid-state structure of phenol-function­alized polyfluorene.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.037
• wR factor = 0.091
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.77 mm

   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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: DIRDIF96 (Beurskens et al., 1996); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2003); software used to prepare material for publication: SHELXTL.

2,7-dibromo-9,9-bis(4-hydroxyphenyl)-9H-fluorene

Crystal data

C25H16Br2O2	F(000) = 1008
Mr = 508.20	Dx = 1.645 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4032 reflections
a = 9.1346 (14) Å	θ = 2.3–25.7°
b = 12.926 (2) Å	µ = 3.97 mm^−1
c = 17.772 (3) Å	T = 193 K
β = 102.004 (2)°	Prism, colourless
V = 2052.5 (6) Å^3	0.77 × 0.28 × 0.25 mm
Z = 4

Data collection

SMART 1000 CCD area detector/Bruker PLATFORM diffractometer	4227 independent reflections
Radiation source: fine-focus sealed tube	3244 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: 8.192 pixels mm^-1	θmax = 26.4°, θmin = 2.0°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2003)	k = −16→16
Tmin = 0.168, Tmax = 0.371	l = −15→22
11022 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.091	w = 1/[σ^2(Fo^2) + (0.0282P)^2 + 1.7675P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
4227 reflections	Δρmax = 0.54 e Å^−3
265 parameters	Δρmin = −0.63 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0037 (4)

Special details

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
Br1	−0.45802 (3)	0.24494 (3)	0.11548 (2)	0.05388 (14)
Br2	0.32211 (5)	−0.13024 (3)	0.54553 (2)	0.06633 (16)
O1	0.3537 (2)	0.43915 (14)	0.42926 (11)	0.0324 (4)
H1O	0.4467	0.4322	0.4345	0.049*
O2	0.3315 (2)	−0.06896 (15)	0.04587 (11)	0.0328 (4)
H2O	0.3174	−0.0275	0.0087	0.049*
C1	−0.1120 (3)	0.08860 (19)	0.25669 (15)	0.0246 (5)
C2	−0.1912 (3)	0.1572 (2)	0.20369 (16)	0.0284 (6)
H2	−0.1410	0.2076	0.1794	0.034*
C3	−0.3466 (3)	0.1503 (2)	0.18694 (17)	0.0327 (6)
C4	−0.4224 (3)	0.0763 (2)	0.22000 (17)	0.0367 (7)
H4	−0.5286	0.0729	0.2067	0.044*
C5	−0.3435 (3)	0.0074 (2)	0.27232 (18)	0.0378 (7)
H5	−0.3944	−0.0446	0.2947	0.045*
C6	−0.1881 (3)	0.0150 (2)	0.29186 (16)	0.0309 (6)
C7	−0.0795 (3)	−0.0387 (2)	0.35115 (17)	0.0327 (6)
C8	−0.1007 (4)	−0.1105 (2)	0.4063 (2)	0.0460 (8)
H8	−0.1969	−0.1391	0.4051	0.055*
C9	0.0199 (4)	−0.1395 (2)	0.4627 (2)	0.0498 (9)
H9	0.0072	−0.1883	0.5008	0.060*
C10	0.1595 (4)	−0.0972 (2)	0.46379 (17)	0.0438 (8)
C11	0.1844 (4)	−0.0271 (2)	0.40815 (16)	0.0351 (7)
H11	0.2812	0.0006	0.4093	0.042*
C12	0.0633 (3)	0.0006 (2)	0.35138 (16)	0.0291 (6)
C13	0.0579 (3)	0.07945 (19)	0.28660 (15)	0.0245 (5)
C14	0.1345 (3)	0.17994 (19)	0.31982 (15)	0.0234 (5)
C15	0.0579 (3)	0.25564 (19)	0.35081 (15)	0.0241 (5)
H15	−0.0466	0.2479	0.3478	0.029*
C16	0.1304 (3)	0.3430 (2)	0.38641 (15)	0.0270 (6)
H16	0.0755	0.3950	0.4062	0.032*
C17	0.2824 (3)	0.35316 (19)	0.39257 (15)	0.0253 (6)
C18	0.3613 (3)	0.2791 (2)	0.36201 (18)	0.0338 (7)
H18	0.4660	0.2866	0.3659	0.041*
C19	0.2875 (3)	0.1936 (2)	0.32568 (18)	0.0357 (7)
H19	0.3425	0.1432	0.3042	0.043*
C20	0.1306 (3)	0.03776 (18)	0.22182 (15)	0.0228 (5)
C21	0.1987 (3)	−0.05904 (19)	0.22490 (15)	0.0245 (5)
H21	0.2015	−0.1019	0.2686	0.029*
C22	0.2624 (3)	−0.0937 (2)	0.16529 (16)	0.0260 (6)
H22	0.3076	−0.1602	0.1683	0.031*
C23	0.2606 (3)	−0.03279 (19)	0.10191 (15)	0.0248 (6)
C24	0.1924 (3)	0.0639 (2)	0.09741 (15)	0.0274 (6)
H24	0.1892	0.1062	0.0534	0.033*
C25	0.1297 (3)	0.0982 (2)	0.15686 (16)	0.0275 (6)
H25	0.0847	0.1648	0.1535	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02635 (17)	0.0690 (3)	0.0616 (3)	0.00104 (15)	−0.00148 (14)	0.01149 (18)
Br2	0.0976 (3)	0.0663 (3)	0.0322 (2)	0.0316 (2)	0.00676 (19)	0.01027 (17)
O1	0.0283 (10)	0.0335 (10)	0.0368 (11)	−0.0084 (8)	0.0097 (9)	−0.0099 (9)
O2	0.0322 (11)	0.0384 (11)	0.0325 (11)	0.0097 (8)	0.0178 (9)	0.0058 (9)
C1	0.0213 (13)	0.0247 (12)	0.0301 (14)	−0.0042 (10)	0.0107 (11)	−0.0079 (11)
C2	0.0226 (13)	0.0331 (14)	0.0308 (15)	−0.0040 (11)	0.0086 (11)	−0.0040 (12)
C3	0.0247 (14)	0.0401 (16)	0.0332 (15)	−0.0018 (12)	0.0060 (11)	−0.0088 (13)
C4	0.0233 (14)	0.0515 (18)	0.0372 (17)	−0.0111 (13)	0.0103 (12)	−0.0143 (14)
C5	0.0353 (16)	0.0436 (17)	0.0399 (17)	−0.0159 (13)	0.0205 (13)	−0.0125 (14)
C6	0.0371 (16)	0.0287 (14)	0.0309 (15)	−0.0077 (11)	0.0166 (12)	−0.0062 (12)
C7	0.0427 (17)	0.0260 (14)	0.0350 (16)	−0.0038 (12)	0.0211 (13)	−0.0032 (12)
C8	0.062 (2)	0.0356 (17)	0.048 (2)	−0.0038 (15)	0.0302 (17)	0.0046 (15)
C9	0.081 (3)	0.0367 (18)	0.0398 (19)	0.0044 (17)	0.0320 (18)	0.0097 (14)
C10	0.068 (2)	0.0385 (17)	0.0266 (16)	0.0185 (16)	0.0145 (15)	0.0016 (13)
C11	0.0440 (17)	0.0330 (15)	0.0299 (16)	0.0069 (12)	0.0112 (13)	−0.0012 (12)
C12	0.0410 (16)	0.0228 (13)	0.0271 (14)	0.0020 (11)	0.0152 (12)	−0.0034 (11)
C13	0.0243 (13)	0.0232 (13)	0.0282 (14)	0.0006 (10)	0.0105 (11)	−0.0010 (11)
C14	0.0222 (12)	0.0239 (13)	0.0251 (13)	−0.0005 (10)	0.0070 (10)	−0.0011 (11)
C15	0.0180 (12)	0.0272 (13)	0.0271 (14)	0.0000 (10)	0.0049 (10)	−0.0006 (11)
C16	0.0241 (13)	0.0282 (13)	0.0286 (14)	0.0048 (10)	0.0056 (11)	−0.0019 (11)
C17	0.0294 (14)	0.0251 (13)	0.0216 (13)	−0.0038 (10)	0.0059 (11)	−0.0005 (10)
C18	0.0194 (13)	0.0388 (15)	0.0450 (18)	−0.0025 (11)	0.0110 (12)	−0.0104 (13)
C19	0.0254 (15)	0.0335 (15)	0.0501 (19)	0.0011 (12)	0.0125 (13)	−0.0101 (14)
C20	0.0198 (12)	0.0223 (12)	0.0274 (14)	−0.0023 (9)	0.0072 (10)	−0.0020 (10)
C21	0.0216 (13)	0.0249 (13)	0.0284 (14)	−0.0017 (10)	0.0081 (10)	0.0032 (11)
C22	0.0229 (13)	0.0215 (12)	0.0349 (15)	0.0010 (10)	0.0089 (11)	0.0015 (11)
C23	0.0167 (12)	0.0298 (14)	0.0293 (14)	−0.0011 (10)	0.0084 (10)	−0.0023 (11)
C24	0.0271 (14)	0.0289 (14)	0.0268 (14)	0.0017 (11)	0.0069 (11)	0.0066 (11)
C25	0.0287 (14)	0.0239 (13)	0.0320 (15)	0.0042 (10)	0.0111 (11)	0.0017 (11)

Geometric parameters (Å, º)

Br1—C3	1.899 (3)	C11—H11	0.9500
Br2—C10	1.898 (3)	C12—C13	1.530 (4)
O1—C17	1.382 (3)	C13—C14	1.534 (3)
O1—H1O	0.8400	C13—C20	1.541 (4)
O2—C23	1.378 (3)	C14—C15	1.382 (4)
O2—H2O	0.8400	C14—C19	1.391 (4)
C1—C2	1.384 (4)	C15—C16	1.393 (4)
C1—C6	1.400 (4)	C15—H15	0.9500
C1—C13	1.537 (3)	C16—C17	1.376 (4)
C2—C3	1.391 (4)	C16—H16	0.9500
C2—H2	0.9500	C17—C18	1.376 (4)
C3—C4	1.382 (4)	C18—C19	1.382 (4)
C4—C5	1.378 (4)	C18—H18	0.9500
C4—H4	0.9500	C19—H19	0.9500
C5—C6	1.393 (4)	C20—C21	1.393 (3)
C5—H5	0.9500	C20—C25	1.393 (4)
C6—C7	1.464 (4)	C21—C22	1.385 (4)
C7—C8	1.392 (4)	C21—H21	0.9500
C7—C12	1.400 (4)	C22—C23	1.372 (4)
C8—C9	1.378 (5)	C22—H22	0.9500
C8—H8	0.9500	C23—C24	1.391 (4)
C9—C10	1.383 (5)	C24—C25	1.376 (4)
C9—H9	0.9500	C24—H24	0.9500
C10—C11	1.395 (4)	C25—H25	0.9500
C11—C12	1.380 (4)
C17—O1—H1O	109.5	C1—C13—C20	109.3 (2)
C23—O2—H2O	109.5	C12—C13—C14	109.5 (2)
C2—C1—C6	120.1 (2)	C12—C13—C20	112.2 (2)
C2—C1—C13	129.2 (2)	C14—C13—C20	110.5 (2)
C6—C1—C13	110.7 (2)	C13—C14—C15	121.6 (2)
C1—C2—C3	118.0 (3)	C13—C14—C19	120.5 (2)
C1—C2—H2	121.0	C15—C14—C19	117.6 (2)
C3—C2—H2	121.0	C14—C15—C16	121.5 (2)
Br1—C3—C2	118.8 (2)	C14—C15—H15	119.2
Br1—C3—C4	118.9 (2)	C16—C15—H15	119.2
C2—C3—C4	122.2 (3)	C15—C16—C17	119.4 (2)
C3—C4—C5	119.7 (3)	C15—C16—H16	120.3
C3—C4—H4	120.1	C17—C16—H16	120.3
C5—C4—H4	120.1	C16—C17—C18	120.3 (2)
C4—C5—C6	119.1 (3)	C16—C17—O1	118.9 (2)
C4—C5—H5	120.5	C18—C17—O1	120.8 (2)
C6—C5—H5	120.5	C17—C18—C19	119.7 (3)
C1—C6—C5	120.8 (3)	C17—C18—H18	120.1
C1—C6—C7	108.6 (2)	C19—C18—H18	120.1
C5—C6—C7	130.5 (3)	C14—C19—C18	121.4 (3)
C6—C7—C8	130.6 (3)	C14—C19—H19	119.3
C6—C7—C12	108.7 (2)	C18—C19—H19	119.3
C8—C7—C12	120.4 (3)	C13—C20—C21	122.9 (2)
C7—C8—C9	119.1 (3)	C13—C20—C25	119.6 (2)
C7—C8—H8	120.5	C21—C20—C25	117.5 (2)
C9—C8—H8	120.5	C20—C21—C22	121.1 (2)
C8—C9—C10	119.9 (3)	C20—C21—H21	119.5
C8—C9—H9	120.1	C22—C21—H21	119.5
C10—C9—H9	120.1	C21—C22—C23	120.4 (2)
Br2—C10—C9	119.6 (2)	C21—C22—H22	119.8
Br2—C10—C11	118.1 (3)	C23—C22—H22	119.8
C9—C10—C11	122.2 (3)	O2—C23—C22	118.1 (2)
C10—C11—C12	117.6 (3)	O2—C23—C24	122.4 (2)
C10—C11—H11	121.2	C22—C23—C24	119.5 (2)
C12—C11—H11	121.2	C23—C24—C25	119.9 (2)
C7—C12—C11	120.8 (3)	C23—C24—H24	120.1
C7—C12—C13	110.8 (2)	C25—C24—H24	120.1
C11—C12—C13	128.2 (3)	C20—C25—C24	121.6 (2)
C1—C13—C12	100.6 (2)	C20—C25—H25	119.2
C1—C13—C14	114.5 (2)	C24—C25—H25	119.2
C6—C1—C2—C3	−0.1 (4)	C7—C12—C13—C14	127.9 (2)
C13—C1—C2—C3	−179.2 (3)	C7—C12—C13—C20	−109.1 (3)
C2—C1—C6—C5	2.1 (4)	C11—C12—C13—C1	−168.5 (3)
C2—C1—C6—C7	−173.6 (2)	C11—C12—C13—C14	−47.6 (3)
C13—C1—C6—C5	−178.6 (2)	C11—C12—C13—C20	75.5 (3)
C13—C1—C6—C7	5.7 (3)	C1—C13—C14—C15	26.6 (3)
C2—C1—C13—C12	171.6 (3)	C1—C13—C14—C19	−159.0 (3)
C2—C1—C13—C14	54.3 (4)	C12—C13—C14—C15	−85.5 (3)
C2—C1—C13—C20	−70.2 (3)	C12—C13—C14—C19	88.9 (3)
C6—C1—C13—C12	−7.6 (3)	C20—C13—C14—C15	150.5 (2)
C6—C1—C13—C14	−124.8 (2)	C20—C13—C14—C19	−35.1 (3)
C6—C1—C13—C20	110.6 (2)	C1—C13—C20—C21	−113.3 (3)
C1—C2—C3—Br1	179.1 (2)	C1—C13—C20—C25	66.7 (3)
C1—C2—C3—C4	−1.5 (4)	C12—C13—C20—C21	−2.7 (3)
Br1—C3—C4—C5	−179.6 (2)	C12—C13—C20—C25	177.4 (2)
C2—C3—C4—C5	1.0 (4)	C14—C13—C20—C21	119.8 (3)
C3—C4—C5—C6	1.1 (4)	C14—C13—C20—C25	−60.1 (3)
C4—C5—C6—C1	−2.6 (4)	C13—C14—C15—C16	174.8 (2)
C4—C5—C6—C7	172.0 (3)	C19—C14—C15—C16	0.3 (4)
C1—C6—C7—C8	173.0 (3)	C15—C14—C19—C18	0.8 (4)
C1—C6—C7—C12	−1.0 (3)	C13—C14—C19—C18	−173.8 (3)
C5—C6—C7—C8	−2.1 (5)	C14—C15—C16—C17	−1.6 (4)
C5—C6—C7—C12	−176.2 (3)	C15—C16—C17—O1	−178.8 (2)
C6—C7—C8—C9	−171.2 (3)	C15—C16—C17—C18	1.7 (4)
C12—C7—C8—C9	2.2 (4)	O1—C17—C18—C19	179.9 (3)
C6—C7—C12—C11	171.8 (2)	C16—C17—C18—C19	−0.6 (4)
C6—C7—C12—C13	−4.1 (3)	C17—C18—C19—C14	−0.7 (5)
C8—C7—C12—C11	−3.0 (4)	C13—C20—C21—C22	179.8 (2)
C8—C7—C12—C13	−178.8 (3)	C25—C20—C21—C22	−0.3 (4)
C7—C8—C9—C10	0.0 (5)	C20—C21—C22—C23	0.5 (4)
C8—C9—C10—Br2	175.7 (2)	C21—C22—C23—O2	177.1 (2)
C8—C9—C10—C11	−1.5 (5)	C21—C22—C23—C24	−0.8 (4)
Br2—C10—C11—C12	−176.5 (2)	O2—C23—C24—C25	−176.8 (2)
C9—C10—C11—C12	0.8 (4)	C22—C23—C24—C25	1.0 (4)
C10—C11—C12—C7	1.5 (4)	C23—C24—C25—C20	−0.9 (4)
C10—C11—C12—C13	176.5 (3)	C13—C20—C25—C24	−179.6 (2)
C7—C12—C13—C1	6.9 (3)	C21—C20—C25—C24	0.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2^i	0.84	1.98	2.819 (3)	173
O2—H2O···O1^ii	0.84	1.90	2.707 (3)	161

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