2′,7′-Di-1-naphthyl­spiro­[cyclo­propane-1,9′-fluorene]

In the title compound, C₃₅H₂₄, the fluorene ring system is essentially planar and makes a dihedral angle of 90.02 (2)° with the plane of the cyclo­propane ring. The dihedral angles between the fluorene ring system and the naphthalene ring systems are 52.26 (3) and 57.55 (3)°, and π–π stacking occurs between nearly parallel naphthalene ring systems.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.094
• Data-to-parameter ratio = 9.2

checkCIF/PLATON results

No syntax errors found



Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.50
           From the CIF: _reflns_number_total               2914
           Count of symmetry unique reflns         2927
           Completeness (_total/calc)             99.56%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   1 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

---

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2',7'-Di-1-naphthylspiro[cyclopropane-1,9'-fluorene]

Crystal data

C35H24	F(000) = 936
Mr = 444.54	Dx = 1.253 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 18017 reflections
a = 17.355 (4) Å	θ = 3.2–27.4°
b = 18.225 (4) Å	µ = 0.07 mm^−1
c = 7.4532 (18) Å	T = 296 K
V = 2357.4 (9) Å^3	Block, colorless
Z = 4	0.24 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	2338 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
Graphite monochromator	θmax = 27.5°, θmin = 3.2°
Detector resolution: 10.00 pixels mm^-1	h = −22→22
ω scans	k = −21→23
21945 measured reflections	l = −9→9
2914 independent 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)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.06P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.002
2914 reflections	Δρmax = 0.13 e Å^−3
317 parameters	Δρmin = −0.13 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0121 (14)

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
C1	0.62463 (9)	0.44907 (9)	0.1873 (2)	0.0412 (4)
C2	0.57995 (9)	0.41676 (9)	0.3229 (2)	0.0423 (4)
C3	0.57828 (9)	0.33737 (10)	0.2923 (3)	0.0447 (4)
C4	0.54340 (11)	0.28078 (11)	0.3880 (3)	0.0546 (5)
H4	0.5137	0.2909	0.4888	0.066*
C5	0.55367 (11)	0.20930 (11)	0.3305 (3)	0.0589 (5)
H5	0.5304	0.1714	0.3940	0.071*
C6	0.59793 (11)	0.19253 (11)	0.1798 (3)	0.0549 (5)
C7	0.63172 (10)	0.24975 (10)	0.0831 (3)	0.0510 (4)
H7	0.6608	0.2396	−0.0188	0.061*
C8	0.62198 (9)	0.32135 (9)	0.1387 (3)	0.0436 (4)
C9	0.65207 (10)	0.39126 (10)	0.0625 (3)	0.0434 (4)
C10	0.65780 (12)	0.40442 (12)	−0.1386 (3)	0.0579 (5)
H10A	0.6434	0.3645	−0.2179	0.069*
H10B	0.6454	0.4530	−0.1830	0.069*
C11	0.72901 (11)	0.39590 (11)	−0.0317 (3)	0.0567 (5)
H11A	0.7601	0.4393	−0.0113	0.068*
H11B	0.7581	0.3508	−0.0462	0.068*
C12	0.63802 (9)	0.52364 (10)	0.1871 (3)	0.0436 (4)
H12	0.6677	0.5446	0.0968	0.052*
C13	0.60721 (9)	0.56773 (10)	0.3218 (3)	0.0455 (4)
C14	0.56140 (11)	0.53515 (11)	0.4546 (3)	0.0519 (5)
H14	0.5397	0.5644	0.5435	0.062*
C15	0.54773 (10)	0.46032 (11)	0.4561 (3)	0.0493 (4)
H15	0.5173	0.4395	0.5452	0.059*
C16	0.61886 (10)	0.64866 (10)	0.3195 (3)	0.0481 (4)
C17	0.55634 (12)	0.69436 (12)	0.3325 (3)	0.0598 (5)
H17	0.5078	0.6742	0.3519	0.072*
C18	0.56364 (14)	0.77079 (12)	0.3172 (4)	0.0711 (7)
H18	0.5203	0.8006	0.3268	0.085*
C19	0.63368 (16)	0.80112 (12)	0.2884 (4)	0.0717 (6)
H19	0.6377	0.8517	0.2739	0.086*
C20	0.70099 (13)	0.75736 (11)	0.2799 (3)	0.0580 (5)
C21	0.77535 (15)	0.78816 (13)	0.2576 (4)	0.0733 (7)
H21	0.7801	0.8385	0.2399	0.088*
C22	0.83931 (15)	0.74619 (15)	0.2613 (4)	0.0745 (7)
H22	0.8875	0.7677	0.2465	0.089*
C23	0.83354 (12)	0.67059 (13)	0.2873 (3)	0.0643 (6)
H23	0.8778	0.6420	0.2934	0.077*
C24	0.76287 (11)	0.63879 (11)	0.3038 (3)	0.0530 (5)
H24	0.7598	0.5882	0.3186	0.064*
C25	0.69421 (10)	0.68021 (10)	0.2990 (3)	0.0477 (4)
C26	0.60699 (12)	0.11480 (11)	0.1219 (3)	0.0579 (5)
C27	0.54332 (13)	0.07342 (12)	0.0869 (4)	0.0751 (7)
H27	0.4949	0.0941	0.1036	0.090*
C28	0.54829 (16)	0.00096 (13)	0.0266 (5)	0.0898 (9)
H28	0.5037	−0.0255	0.0027	0.108*
C29	0.61787 (17)	−0.03046 (13)	0.0033 (4)	0.0802 (8)
H29	0.6208	−0.0787	−0.0371	0.096*
C30	0.68598 (15)	0.00850 (12)	0.0392 (3)	0.0654 (6)
C31	0.75929 (18)	−0.02313 (14)	0.0156 (4)	0.0812 (8)
H31	0.7629	−0.0709	−0.0277	0.097*
C32	0.82399 (18)	0.01381 (17)	0.0540 (5)	0.0876 (8)
H32	0.8716	−0.0084	0.0361	0.105*
C33	0.82049 (15)	0.08534 (16)	0.1206 (4)	0.0779 (7)
H33	0.8657	0.1101	0.1494	0.093*
C34	0.75088 (13)	0.11916 (11)	0.1436 (3)	0.0636 (5)
H34	0.7492	0.1670	0.1871	0.076*
C35	0.68129 (13)	0.08228 (11)	0.1020 (3)	0.0563 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0329 (7)	0.0542 (10)	0.0366 (8)	0.0011 (7)	−0.0017 (7)	0.0027 (8)
C2	0.0321 (7)	0.0558 (10)	0.0389 (9)	−0.0007 (7)	−0.0015 (7)	0.0032 (8)
C3	0.0339 (7)	0.0552 (10)	0.0450 (10)	−0.0006 (7)	0.0005 (8)	0.0039 (9)
C4	0.0478 (10)	0.0646 (12)	0.0514 (11)	−0.0012 (9)	0.0117 (9)	0.0060 (10)
C5	0.0534 (10)	0.0577 (12)	0.0657 (14)	−0.0057 (9)	0.0092 (11)	0.0114 (11)
C6	0.0476 (9)	0.0547 (11)	0.0625 (13)	−0.0016 (8)	0.0008 (10)	0.0079 (10)
C7	0.0480 (9)	0.0558 (10)	0.0493 (11)	0.0021 (9)	0.0070 (9)	0.0012 (9)
C8	0.0379 (8)	0.0520 (10)	0.0408 (10)	−0.0014 (7)	0.0005 (8)	0.0039 (8)
C9	0.0397 (8)	0.0529 (10)	0.0376 (9)	0.0006 (8)	0.0037 (7)	0.0022 (8)
C10	0.0692 (12)	0.0670 (12)	0.0375 (10)	−0.0076 (10)	0.0065 (10)	0.0004 (9)
C11	0.0486 (10)	0.0663 (12)	0.0550 (12)	−0.0038 (8)	0.0169 (9)	−0.0007 (10)
C12	0.0394 (8)	0.0550 (10)	0.0365 (8)	−0.0009 (7)	0.0009 (7)	0.0037 (8)
C13	0.0381 (8)	0.0560 (10)	0.0424 (10)	0.0014 (7)	−0.0036 (8)	−0.0010 (9)
C14	0.0456 (9)	0.0648 (11)	0.0453 (10)	0.0027 (8)	0.0052 (9)	−0.0078 (9)
C15	0.0399 (9)	0.0651 (12)	0.0429 (9)	−0.0020 (8)	0.0080 (8)	0.0037 (9)
C16	0.0488 (9)	0.0563 (10)	0.0392 (10)	0.0028 (8)	−0.0043 (8)	−0.0028 (9)
C17	0.0551 (10)	0.0675 (12)	0.0568 (12)	0.0072 (9)	−0.0064 (10)	−0.0089 (11)
C18	0.0752 (14)	0.0652 (13)	0.0731 (16)	0.0229 (11)	−0.0165 (14)	−0.0152 (12)
C19	0.0959 (17)	0.0533 (12)	0.0658 (15)	0.0034 (12)	−0.0146 (14)	−0.0043 (12)
C20	0.0731 (13)	0.0559 (11)	0.0450 (11)	−0.0040 (10)	−0.0050 (10)	−0.0044 (10)
C21	0.0945 (19)	0.0644 (13)	0.0611 (15)	−0.0258 (13)	−0.0017 (13)	0.0003 (11)
C22	0.0680 (15)	0.0923 (17)	0.0633 (15)	−0.0269 (13)	0.0058 (12)	−0.0037 (13)
C23	0.0515 (11)	0.0822 (15)	0.0592 (14)	−0.0066 (10)	0.0026 (10)	−0.0045 (12)
C24	0.0531 (11)	0.0624 (10)	0.0435 (10)	−0.0024 (9)	−0.0021 (9)	−0.0006 (10)
C25	0.0539 (10)	0.0552 (10)	0.0339 (9)	−0.0024 (8)	−0.0031 (8)	−0.0032 (8)
C26	0.0583 (11)	0.0540 (11)	0.0616 (13)	0.0000 (9)	0.0016 (10)	0.0088 (10)
C27	0.0614 (12)	0.0608 (13)	0.103 (2)	−0.0057 (10)	0.0059 (14)	0.0043 (14)
C28	0.0828 (17)	0.0629 (14)	0.124 (3)	−0.0161 (13)	0.0043 (18)	−0.0084 (16)
C29	0.1002 (19)	0.0558 (12)	0.085 (2)	−0.0047 (13)	0.0003 (16)	−0.0011 (13)
C30	0.0836 (15)	0.0586 (12)	0.0538 (12)	0.0123 (11)	0.0048 (12)	0.0070 (10)
C31	0.0940 (18)	0.0763 (15)	0.0731 (18)	0.0253 (15)	0.0089 (15)	0.0041 (13)
C32	0.0817 (17)	0.101 (2)	0.0801 (19)	0.0342 (16)	0.0119 (16)	0.0090 (16)
C33	0.0623 (13)	0.102 (2)	0.0697 (16)	0.0089 (13)	−0.0004 (13)	0.0144 (15)
C34	0.0623 (11)	0.0735 (12)	0.0548 (13)	0.0057 (11)	0.0001 (11)	0.0065 (11)
C35	0.0611 (11)	0.0580 (12)	0.0498 (12)	0.0055 (9)	0.0030 (10)	0.0079 (9)

Geometric parameters (Å, º)

C1—C12	1.379 (2)	C17—H17	0.9300
C1—C2	1.404 (2)	C18—C19	1.352 (4)
C1—C9	1.484 (3)	C18—H18	0.9300
C2—C15	1.388 (3)	C19—C20	1.416 (3)
C2—C3	1.465 (3)	C19—H19	0.9300
C3—C4	1.392 (3)	C20—C21	1.417 (3)
C3—C8	1.404 (3)	C20—C25	1.418 (3)
C4—C5	1.383 (3)	C21—C22	1.348 (3)
C4—H4	0.9300	C21—H21	0.9300
C5—C6	1.394 (3)	C22—C23	1.395 (3)
C5—H5	0.9300	C22—H22	0.9300
C6—C7	1.397 (3)	C23—C24	1.362 (3)
C6—C26	1.489 (3)	C23—H23	0.9300
C7—C8	1.380 (2)	C24—C25	1.411 (3)
C7—H7	0.9300	C24—H24	0.9300
C8—C9	1.489 (2)	C26—C27	1.363 (3)
C9—C10	1.521 (3)	C26—C35	1.427 (3)
C9—C11	1.511 (3)	C27—C28	1.397 (3)
C10—C11	1.479 (3)	C27—H27	0.9300
C10—H10A	0.9700	C28—C29	1.348 (4)
C10—H10B	0.9700	C28—H28	0.9300
C11—H11A	0.9700	C29—C30	1.405 (4)
C11—H11B	0.9700	C29—H29	0.9300
C12—C13	1.392 (3)	C30—C31	1.408 (4)
C12—H12	0.9300	C30—C35	1.426 (3)
C13—C14	1.401 (3)	C31—C32	1.340 (4)
C13—C16	1.489 (3)	C31—H31	0.9300
C14—C15	1.384 (3)	C32—C33	1.396 (4)
C14—H14	0.9300	C32—H32	0.9300
C15—H15	0.9300	C33—C34	1.367 (3)
C16—C17	1.371 (3)	C33—H33	0.9300
C16—C25	1.437 (3)	C34—C35	1.416 (3)
C17—C18	1.403 (3)	C34—H34	0.9300
C12—C1—C2	120.48 (16)	C16—C17—C18	121.7 (2)
C12—C1—C9	130.19 (16)	C16—C17—H17	119.1
C2—C1—C9	109.32 (15)	C18—C17—H17	119.1
C15—C2—C1	119.82 (16)	C19—C18—C17	120.0 (2)
C15—C2—C3	131.91 (16)	C19—C18—H18	120.0
C1—C2—C3	108.25 (15)	C17—C18—H18	120.0
C4—C3—C8	119.89 (17)	C18—C19—C20	121.2 (2)
C4—C3—C2	131.35 (17)	C18—C19—H19	119.4
C8—C3—C2	108.76 (15)	C20—C19—H19	119.4
C5—C4—C3	118.90 (19)	C19—C20—C21	122.2 (2)
C5—C4—H4	120.6	C19—C20—C25	119.0 (2)
C3—C4—H4	120.6	C21—C20—C25	118.7 (2)
C4—C5—C6	121.80 (18)	C22—C21—C20	121.5 (2)
C4—C5—H5	119.1	C22—C21—H21	119.3
C6—C5—H5	119.1	C20—C21—H21	119.3
C5—C6—C7	118.91 (19)	C21—C22—C23	120.3 (2)
C5—C6—C26	120.01 (18)	C21—C22—H22	119.9
C7—C6—C26	121.1 (2)	C23—C22—H22	119.9
C8—C7—C6	120.0 (2)	C24—C23—C22	119.8 (2)
C8—C7—H7	120.0	C24—C23—H23	120.1
C6—C7—H7	120.0	C22—C23—H23	120.1
C7—C8—C3	120.53 (16)	C23—C24—C25	122.04 (19)
C7—C8—C9	130.66 (17)	C23—C24—H24	119.0
C3—C8—C9	108.81 (15)	C25—C24—H24	119.0
C1—C9—C8	104.83 (15)	C24—C25—C20	117.56 (17)
C1—C9—C11	122.36 (16)	C24—C25—C16	123.50 (17)
C8—C9—C11	122.34 (15)	C20—C25—C16	118.89 (17)
C1—C9—C10	121.78 (17)	C27—C26—C35	118.88 (19)
C8—C9—C10	122.23 (17)	C27—C26—C6	119.75 (19)
C11—C9—C10	58.36 (15)	C35—C26—C6	121.37 (18)
C11—C10—C9	60.47 (14)	C26—C27—C28	122.3 (2)
C11—C10—H10A	117.7	C26—C27—H27	118.8
C9—C10—H10A	117.7	C28—C27—H27	118.8
C11—C10—H10B	117.7	C29—C28—C27	119.9 (2)
C9—C10—H10B	117.7	C29—C28—H28	120.1
H10A—C10—H10B	114.8	C27—C28—H28	120.1
C10—C11—C9	61.16 (13)	C28—C29—C30	121.0 (2)
C10—C11—H11A	117.7	C28—C29—H29	119.5
C9—C11—H11A	117.7	C30—C29—H29	119.5
C10—C11—H11B	117.7	C29—C30—C31	122.0 (2)
C9—C11—H11B	117.7	C29—C30—C35	119.4 (2)
H11A—C11—H11B	114.8	C31—C30—C35	118.6 (2)
C1—C12—C13	120.23 (17)	C32—C31—C30	121.7 (2)
C1—C12—H12	119.9	C32—C31—H31	119.2
C13—C12—H12	119.9	C30—C31—H31	119.2
C12—C13—C14	118.84 (17)	C31—C32—C33	120.6 (2)
C12—C13—C16	120.74 (17)	C31—C32—H32	119.7
C14—C13—C16	120.33 (17)	C33—C32—H32	119.7
C15—C14—C13	121.36 (18)	C34—C33—C32	120.3 (3)
C15—C14—H14	119.3	C34—C33—H33	119.9
C13—C14—H14	119.3	C32—C33—H33	119.9
C14—C15—C2	119.24 (17)	C33—C34—C35	120.8 (2)
C14—C15—H15	120.4	C33—C34—H34	119.6
C2—C15—H15	120.4	C35—C34—H34	119.6
C17—C16—C25	118.98 (18)	C34—C35—C30	118.1 (2)
C17—C16—C13	119.57 (17)	C34—C35—C26	123.4 (2)
C25—C16—C13	121.42 (15)	C30—C35—C26	118.5 (2)