Crystal structures of a series of 6-aryl-1,3-diphenyl­fulvenes

The synthesis and structures of a series of 6-aryl-1,3-diphenyl­fuvlenes with (fulvene is 5-methyl­idene­cyclo­penta-1,3-diene) varying methyl­ation patterns on the 6-phenyl substituent are reported. A network of C—H...π ring inter­actions consolidates the packing in each structure.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.048
• wR factor = 0.122
• Data-to-parameter ratio = 16.8

Structure: II

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.100
• Data-to-parameter ratio = 15.3

Structure: III

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.043
• wR factor = 0.108
• Data-to-parameter ratio = 13.7

Structure: IV

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.050
• wR factor = 0.137
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........       7.06 Note
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............      0.005 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.590         12 Report

Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         21 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         17 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 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




Datablock: II


Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........       7.06 Note
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............      0.005 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.590         12 Report

Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         17 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 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




Datablock: III



Alert level C
STRVA01_ALERT_4_C           Flack parameter is too small
           From the CIF: _refine_ls_abs_structure_Flack   -6.000
           From the CIF: _refine_ls_abs_structure_Flack_su   10.000
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........       7.06 Note
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............      0.005 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.590         12 Report

Alert level G
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .     10.000 Report
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        56% Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT916_ALERT_2_G Hooft y and Flack x Parameter Values Differ by .       5.72 Check
PLAT953_ALERT_1_G Reported (CIF) and Actual (FCF) Hmax Differ by .          1 Units
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

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




Datablock: IV


Alert level G
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C27 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         20 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          5 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

For all structures, data collection: APEX3 (Bruker, 2017); cell refinement: SAINT (Bruker, 2017); data reduction: SAINT (Bruker, 2017); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae, et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

{3-[(3-Methylphenyl)methylidene]-4-phenylcyclopenta-1,4-dien-1-yl}benzene (I)

Crystal data

C25H20	F(000) = 1360
Mr = 320.41	Dx = 1.191 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 29.230 (17) Å	Cell parameters from 4339 reflections
b = 5.800 (3) Å	θ = 2.9–24.4°
c = 22.071 (12) Å	µ = 0.07 mm^−1
β = 107.248 (17)°	T = 100 K
V = 3573 (3) Å^3	Prism, red
Z = 8	0.25 × 0.21 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer	3013 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.052
Absorption correction: multi-scan SADABS	θmax = 26.8°, θmin = 1.9°
Tmin = 0.832, Tmax = 0.901	h = −36→36
31841 measured reflections	k = −7→7
3817 independent reflections	l = −28→27

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.122	w = 1/[σ^2(Fo^2) + (0.0482P)^2 + 3.8961P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3817 reflections	Δρmax = 0.33 e Å^−3
227 parameters	Δρmin = −0.19 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.57871 (5)	0.4490 (3)	0.23560 (7)	0.0219 (3)
C2	0.57462 (5)	0.4576 (3)	0.29513 (7)	0.0229 (3)
H2	0.554463	0.364773	0.310252	0.027*
C3	0.60677 (5)	0.6356 (3)	0.33229 (7)	0.0222 (3)
C4	0.62991 (5)	0.7360 (3)	0.29436 (7)	0.0235 (3)
H4	0.651702	0.856706	0.305993	0.028*
C5	0.61519 (5)	0.6246 (3)	0.23236 (7)	0.0221 (3)
C6	0.63418 (5)	0.6503 (3)	0.18410 (7)	0.0238 (3)
H6	0.623184	0.548206	0.150415	0.029*
C7	0.55041 (5)	0.2988 (3)	0.18388 (7)	0.0218 (3)
C8	0.53551 (5)	0.3688 (3)	0.12045 (7)	0.0255 (3)
H8	0.544591	0.512625	0.109349	0.031*
C9	0.50730 (6)	0.2255 (3)	0.07390 (8)	0.0303 (4)
H9	0.498411	0.272695	0.031741	0.036*
C10	0.49212 (6)	0.0122 (3)	0.08943 (8)	0.0306 (4)
H10	0.472725	−0.081758	0.058066	0.037*
C11	0.50628 (6)	−0.0585 (3)	0.15223 (8)	0.0275 (4)
H11	0.496034	−0.199944	0.163231	0.033*
C12	0.53569 (5)	0.0812 (3)	0.19877 (7)	0.0235 (3)
H12	0.545815	0.029678	0.240537	0.028*
C13	0.61345 (5)	0.6870 (3)	0.39949 (7)	0.0235 (3)
C14	0.59996 (6)	0.5279 (3)	0.43855 (7)	0.0269 (4)
H14	0.586124	0.388692	0.421668	0.032*
C15	0.60698 (6)	0.5755 (3)	0.50228 (8)	0.0320 (4)
H15	0.597703	0.468403	0.527717	0.038*
C16	0.62776 (6)	0.7819 (3)	0.52829 (8)	0.0331 (4)
H16	0.632614	0.813134	0.571065	0.040*
C17	0.64122 (6)	0.9410 (3)	0.49002 (8)	0.0334 (4)
H17	0.655280	1.079353	0.507240	0.040*
C18	0.63390 (6)	0.8956 (3)	0.42650 (8)	0.0293 (4)
H18	0.642674	1.004989	0.401210	0.035*
C19	0.67002 (5)	0.8189 (3)	0.17789 (7)	0.0233 (3)
C20	0.69945 (5)	0.7614 (3)	0.14047 (7)	0.0255 (3)
H20	0.694917	0.620567	0.119385	0.031*
C21	0.73507 (6)	0.9072 (3)	0.13377 (7)	0.0279 (4)
C22	0.74101 (6)	1.1205 (3)	0.16461 (8)	0.0302 (4)
H22	0.764784	1.220841	0.160703	0.036*
C23	0.71154 (6)	1.1835 (3)	0.20115 (7)	0.0272 (4)
H23	0.715732	1.325711	0.221509	0.033*
C24	0.67616 (6)	1.0360 (3)	0.20731 (7)	0.0248 (3)
H24	0.656224	1.080714	0.231134	0.030*
C25	0.76705 (7)	0.8402 (4)	0.09398 (10)	0.0443 (5)
H25A	0.759165	0.687097	0.077736	0.066*
H25B	0.799917	0.844814	0.119636	0.066*
H25C	0.762396	0.946296	0.059275	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0181 (7)	0.0214 (8)	0.0268 (8)	0.0013 (6)	0.0074 (6)	0.0003 (6)
C2	0.0207 (7)	0.0242 (8)	0.0245 (8)	−0.0022 (6)	0.0080 (6)	−0.0003 (6)
C3	0.0182 (7)	0.0229 (8)	0.0250 (8)	0.0014 (6)	0.0055 (6)	0.0006 (6)
C4	0.0201 (7)	0.0236 (8)	0.0252 (8)	0.0000 (6)	0.0045 (6)	0.0001 (6)
C5	0.0197 (7)	0.0213 (8)	0.0255 (8)	0.0025 (6)	0.0072 (6)	0.0026 (6)
C6	0.0235 (8)	0.0237 (8)	0.0233 (7)	0.0017 (6)	0.0055 (6)	−0.0023 (6)
C7	0.0185 (7)	0.0231 (8)	0.0255 (8)	0.0025 (6)	0.0092 (6)	−0.0032 (6)
C8	0.0252 (8)	0.0258 (8)	0.0275 (8)	−0.0001 (7)	0.0108 (7)	−0.0005 (6)
C9	0.0294 (9)	0.0375 (10)	0.0241 (8)	0.0027 (7)	0.0083 (7)	−0.0033 (7)
C10	0.0263 (8)	0.0326 (9)	0.0322 (9)	−0.0029 (7)	0.0074 (7)	−0.0127 (7)
C11	0.0256 (8)	0.0225 (8)	0.0362 (9)	−0.0012 (7)	0.0120 (7)	−0.0056 (7)
C12	0.0215 (7)	0.0244 (8)	0.0261 (8)	0.0025 (6)	0.0093 (6)	−0.0013 (6)
C13	0.0199 (7)	0.0267 (8)	0.0227 (7)	0.0013 (6)	0.0046 (6)	−0.0009 (6)
C14	0.0304 (8)	0.0246 (8)	0.0251 (8)	−0.0017 (7)	0.0074 (7)	−0.0015 (6)
C15	0.0404 (10)	0.0328 (9)	0.0231 (8)	0.0005 (8)	0.0102 (7)	0.0035 (7)
C16	0.0404 (10)	0.0361 (10)	0.0200 (8)	0.0021 (8)	0.0045 (7)	−0.0016 (7)
C17	0.0369 (9)	0.0322 (9)	0.0271 (8)	−0.0048 (8)	0.0035 (7)	−0.0067 (7)
C18	0.0315 (9)	0.0278 (9)	0.0278 (8)	−0.0035 (7)	0.0076 (7)	0.0012 (7)
C19	0.0246 (8)	0.0245 (8)	0.0194 (7)	0.0008 (6)	0.0045 (6)	0.0022 (6)
C20	0.0264 (8)	0.0255 (8)	0.0242 (8)	0.0020 (7)	0.0068 (6)	0.0004 (6)
C21	0.0254 (8)	0.0344 (9)	0.0246 (8)	0.0021 (7)	0.0087 (6)	0.0037 (7)
C22	0.0242 (8)	0.0316 (9)	0.0324 (9)	−0.0064 (7)	0.0047 (7)	0.0068 (7)
C23	0.0274 (8)	0.0239 (8)	0.0271 (8)	0.0006 (7)	0.0029 (6)	0.0000 (6)
C24	0.0279 (8)	0.0267 (8)	0.0210 (7)	0.0012 (7)	0.0090 (6)	0.0016 (6)
C25	0.0418 (11)	0.0486 (12)	0.0519 (12)	−0.0053 (9)	0.0283 (9)	−0.0048 (10)

Geometric parameters (Å, º)

C1—C2	1.355 (2)	C13—C18	1.402 (2)
C1—C5	1.492 (2)	C14—H14	0.9300
C1—C7	1.478 (2)	C14—C15	1.388 (2)
C2—H2	0.9300	C15—H15	0.9300
C2—C3	1.471 (2)	C15—C16	1.387 (3)
C3—C4	1.354 (2)	C16—H16	0.9300
C3—C13	1.468 (2)	C16—C17	1.384 (3)
C4—H4	0.9300	C17—H17	0.9300
C4—C5	1.458 (2)	C17—C18	1.379 (2)
C5—C6	1.347 (2)	C18—H18	0.9300
C6—H6	0.9300	C19—C20	1.398 (2)
C6—C19	1.469 (2)	C19—C24	1.403 (2)
C7—C8	1.397 (2)	C20—H20	0.9300
C7—C12	1.404 (2)	C20—C21	1.383 (2)
C8—H8	0.9300	C21—C22	1.398 (2)
C8—C9	1.387 (2)	C21—C25	1.511 (2)
C9—H9	0.9300	C22—H22	0.9300
C9—C10	1.391 (3)	C22—C23	1.392 (2)
C10—H10	0.9300	C23—H23	0.9300
C10—C11	1.386 (2)	C23—C24	1.380 (2)
C11—H11	0.9300	C24—H24	0.9300
C11—C12	1.388 (2)	C25—H25A	0.9600
C12—H12	0.9300	C25—H25B	0.9600
C13—C14	1.397 (2)	C25—H25C	0.9600
C2—C1—C5	106.92 (13)	C13—C14—H14	119.7
C2—C1—C7	125.48 (14)	C15—C14—C13	120.67 (16)
C7—C1—C5	127.55 (13)	C15—C14—H14	119.7
C1—C2—H2	125.0	C14—C15—H15	119.8
C1—C2—C3	109.94 (14)	C16—C15—C14	120.40 (16)
C3—C2—H2	125.0	C16—C15—H15	119.8
C4—C3—C2	108.10 (14)	C15—C16—H16	120.3
C4—C3—C13	126.58 (14)	C17—C16—C15	119.43 (16)
C13—C3—C2	125.28 (14)	C17—C16—H16	120.3
C3—C4—H4	125.4	C16—C17—H17	119.8
C3—C4—C5	109.10 (14)	C18—C17—C16	120.43 (16)
C5—C4—H4	125.4	C18—C17—H17	119.8
C4—C5—C1	105.89 (13)	C13—C18—H18	119.5
C6—C5—C1	125.53 (14)	C17—C18—C13	121.01 (16)
C6—C5—C4	128.10 (15)	C17—C18—H18	119.5
C5—C6—H6	115.9	C20—C19—C6	118.51 (14)
C5—C6—C19	128.29 (15)	C20—C19—C24	118.07 (14)
C19—C6—H6	115.9	C24—C19—C6	123.42 (14)
C8—C7—C1	122.65 (14)	C19—C20—H20	118.9
C8—C7—C12	118.00 (14)	C21—C20—C19	122.15 (15)
C12—C7—C1	119.28 (14)	C21—C20—H20	118.9
C7—C8—H8	119.7	C20—C21—C22	118.53 (15)
C9—C8—C7	120.56 (15)	C20—C21—C25	121.35 (16)
C9—C8—H8	119.7	C22—C21—C25	120.11 (16)
C8—C9—H9	119.6	C21—C22—H22	119.8
C8—C9—C10	120.89 (16)	C23—C22—C21	120.38 (15)
C10—C9—H9	119.6	C23—C22—H22	119.8
C9—C10—H10	120.4	C22—C23—H23	119.8
C11—C10—C9	119.15 (15)	C24—C23—C22	120.34 (16)
C11—C10—H10	120.4	C24—C23—H23	119.8
C10—C11—H11	119.9	C19—C24—H24	119.8
C10—C11—C12	120.22 (16)	C23—C24—C19	120.48 (15)
C12—C11—H11	119.9	C23—C24—H24	119.8
C7—C12—H12	119.4	C21—C25—H25A	109.5
C11—C12—C7	121.14 (15)	C21—C25—H25B	109.5
C11—C12—H12	119.4	C21—C25—H25C	109.5
C14—C13—C3	120.79 (14)	H25A—C25—H25B	109.5
C14—C13—C18	118.05 (15)	H25A—C25—H25C	109.5
C18—C13—C3	121.16 (14)	H25B—C25—H25C	109.5

Hydrogen-bond geometry (Å, º)

Cg1 and Cg2 are the centroids of the C13–C18 and C19–C24 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cg1^i	0.93	2.83	3.539 (2)	134
C16—H16···Cg2^ii	0.93	2.86	3.589 (2)	136
C23—H23···Cg2^iii	0.93	2.90	3.547 (2)	128

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

{3-[(4-Methylphenyl)methylidene]-4-phenylcyclopenta-1,4-dien-1-yl}benzene (II)

Crystal data

C25H20	F(000) = 680
Mr = 320.41	Dx = 1.222 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.208 (2) Å	Cell parameters from 6861 reflections
b = 5.8774 (7) Å	θ = 2.2–26.1°
c = 16.1884 (18) Å	µ = 0.07 mm^−1
β = 107.710 (1)°	T = 100 K
V = 1740.9 (3) Å^3	Rect. Prism, red
Z = 4	0.43 × 0.27 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer	2972 reflections with I > 2σ(I)
Radiation source: fine focus sealed tube	Rint = 0.038
φ and ω scans	θmax = 26.2°, θmin = 2.2°
Absorption correction: multi-scan SADABS	h = −23→23
Tmin = 0.691, Tmax = 0.745	k = −7→7
30237 measured reflections	l = −20→20
3473 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.100	w = 1/[σ^2(Fo^2) + (0.0394P)^2 + 0.8955P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3473 reflections	Δρmax = 0.22 e Å^−3
227 parameters	Δρmin = −0.19 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.21805 (7)	0.4854 (2)	0.67244 (8)	0.0199 (3)
C19	0.39564 (7)	0.1392 (2)	0.78528 (8)	0.0196 (3)
C3	0.16408 (7)	0.3062 (2)	0.76451 (8)	0.0199 (3)
C13	0.23043 (6)	0.6328 (2)	0.60483 (8)	0.0199 (3)
C24	0.46911 (7)	0.2083 (2)	0.81558 (8)	0.0205 (3)
H24	0.482874	0.351246	0.797988	0.025*
C6	0.34162 (7)	0.2980 (2)	0.73220 (8)	0.0199 (3)
H6	0.358882	0.400502	0.697460	0.024*
C21	0.43165 (7)	−0.2155 (2)	0.86275 (8)	0.0217 (3)
H21	0.418584	−0.361899	0.878004	0.026*
C22	0.50403 (7)	−0.1435 (2)	0.89566 (8)	0.0209 (3)
C23	0.52175 (7)	0.0712 (2)	0.87068 (8)	0.0212 (3)
H23	0.570728	0.123926	0.891873	0.025*
C4	0.23106 (7)	0.2078 (2)	0.78063 (8)	0.0205 (3)
H4	0.249483	0.087659	0.820575	0.025*
C14	0.27283 (7)	0.5647 (2)	0.55254 (8)	0.0218 (3)
H14	0.294824	0.418298	0.560510	0.026*
C7	0.11136 (7)	0.2699 (2)	0.81300 (8)	0.0205 (3)
C5	0.26996 (7)	0.3166 (2)	0.72660 (8)	0.0195 (3)
C20	0.37819 (7)	−0.0787 (2)	0.80827 (8)	0.0206 (3)
H20	0.329440	−0.133081	0.786414	0.025*
C2	0.15635 (7)	0.4766 (2)	0.69629 (8)	0.0217 (3)
H2	0.114171	0.567633	0.672247	0.026*
C18	0.19736 (7)	0.8485 (2)	0.58962 (8)	0.0229 (3)
H18	0.168610	0.899257	0.624501	0.027*
C8	0.11440 (7)	0.0724 (2)	0.86246 (8)	0.0240 (3)
H8	0.146980	−0.046782	0.859555	0.029*
C12	0.06039 (7)	0.4379 (2)	0.81513 (8)	0.0235 (3)
H12	0.055986	0.569546	0.779883	0.028*
C17	0.20606 (7)	0.9880 (2)	0.52453 (9)	0.0277 (3)
H17	0.181975	1.131132	0.513845	0.033*
C15	0.28318 (7)	0.7086 (2)	0.48909 (8)	0.0256 (3)
H15	0.313325	0.661580	0.455334	0.031*
C9	0.07027 (7)	0.0496 (3)	0.91556 (9)	0.0284 (3)
H9	0.073164	−0.084411	0.949270	0.034*
C11	0.01606 (7)	0.4138 (3)	0.86843 (9)	0.0272 (3)
H11	−0.018208	0.529317	0.869678	0.033*
C16	0.24982 (7)	0.9197 (2)	0.47484 (9)	0.0285 (3)
H16	0.256832	1.017343	0.431291	0.034*
C10	0.02185 (7)	0.2213 (3)	0.91982 (9)	0.0289 (3)
H10	−0.007197	0.207094	0.957700	0.035*
C25	0.56192 (7)	−0.2930 (2)	0.95447 (9)	0.0277 (3)
H25A	0.582960	−0.216495	1.010312	0.042*
H25B	0.600443	−0.322080	0.927669	0.042*
H25C	0.539995	−0.437632	0.963685	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0197 (6)	0.0202 (6)	0.0184 (6)	0.0004 (5)	0.0035 (5)	−0.0010 (5)
C19	0.0201 (6)	0.0221 (6)	0.0176 (6)	0.0027 (5)	0.0074 (5)	−0.0014 (5)
C3	0.0196 (6)	0.0205 (6)	0.0185 (6)	−0.0006 (5)	0.0043 (5)	−0.0015 (5)
C13	0.0158 (6)	0.0224 (6)	0.0188 (6)	−0.0023 (5)	0.0013 (5)	0.0012 (5)
C24	0.0224 (6)	0.0192 (6)	0.0219 (6)	0.0011 (5)	0.0096 (5)	0.0003 (5)
C6	0.0219 (6)	0.0201 (6)	0.0182 (6)	0.0004 (5)	0.0067 (5)	−0.0004 (5)
C21	0.0240 (6)	0.0196 (6)	0.0241 (6)	0.0017 (5)	0.0113 (5)	0.0014 (5)
C22	0.0220 (6)	0.0231 (6)	0.0190 (6)	0.0053 (5)	0.0084 (5)	0.0009 (5)
C23	0.0177 (6)	0.0242 (7)	0.0221 (6)	0.0007 (5)	0.0065 (5)	−0.0024 (5)
C4	0.0223 (6)	0.0200 (6)	0.0191 (6)	0.0009 (5)	0.0060 (5)	0.0006 (5)
C14	0.0190 (6)	0.0238 (7)	0.0207 (6)	−0.0010 (5)	0.0033 (5)	0.0011 (5)
C7	0.0174 (6)	0.0245 (7)	0.0180 (6)	−0.0034 (5)	0.0030 (5)	−0.0011 (5)
C5	0.0211 (6)	0.0193 (6)	0.0176 (6)	0.0006 (5)	0.0051 (5)	−0.0011 (5)
C20	0.0185 (6)	0.0215 (6)	0.0225 (6)	0.0005 (5)	0.0073 (5)	−0.0015 (5)
C2	0.0191 (6)	0.0228 (7)	0.0220 (6)	0.0023 (5)	0.0046 (5)	0.0022 (5)
C18	0.0195 (6)	0.0230 (7)	0.0242 (6)	−0.0005 (5)	0.0038 (5)	−0.0008 (5)
C8	0.0194 (6)	0.0262 (7)	0.0240 (6)	−0.0027 (5)	0.0028 (5)	0.0017 (5)
C12	0.0210 (6)	0.0252 (7)	0.0238 (6)	−0.0014 (5)	0.0058 (5)	0.0008 (5)
C17	0.0253 (7)	0.0224 (7)	0.0294 (7)	−0.0016 (6)	−0.0007 (6)	0.0049 (6)
C15	0.0214 (6)	0.0348 (8)	0.0196 (6)	−0.0048 (6)	0.0046 (5)	0.0012 (6)
C9	0.0243 (7)	0.0337 (8)	0.0253 (7)	−0.0066 (6)	0.0049 (5)	0.0066 (6)
C11	0.0201 (6)	0.0338 (8)	0.0281 (7)	−0.0009 (6)	0.0080 (5)	−0.0042 (6)
C16	0.0278 (7)	0.0305 (8)	0.0232 (7)	−0.0074 (6)	0.0021 (5)	0.0088 (6)
C10	0.0211 (7)	0.0419 (8)	0.0249 (7)	−0.0083 (6)	0.0091 (5)	0.0000 (6)
C25	0.0228 (7)	0.0290 (7)	0.0305 (7)	0.0040 (6)	0.0067 (6)	0.0063 (6)

Geometric parameters (Å, º)

C1—C13	1.4707 (17)	C14—C15	1.3906 (18)
C1—C5	1.4883 (17)	C7—C8	1.4012 (18)
C1—C2	1.3547 (18)	C7—C12	1.3981 (19)
C19—C24	1.4057 (17)	C20—H20	0.9500
C19—C6	1.4642 (17)	C2—H2	0.9500
C19—C20	1.4023 (18)	C18—H18	0.9500
C3—C4	1.3616 (17)	C18—C17	1.3850 (19)
C3—C7	1.4733 (17)	C8—H8	0.9500
C3—C2	1.4641 (17)	C8—C9	1.3850 (19)
C13—C14	1.3997 (18)	C12—H12	0.9500
C13—C18	1.4056 (18)	C12—C11	1.3916 (18)
C24—H24	0.9500	C17—H17	0.9500
C24—C23	1.3852 (18)	C17—C16	1.388 (2)
C6—H6	0.9500	C15—H15	0.9500
C6—C5	1.3561 (17)	C15—C16	1.383 (2)
C21—H21	0.9500	C9—H9	0.9500
C21—C22	1.3946 (18)	C9—C10	1.388 (2)
C21—C20	1.3883 (18)	C11—H11	0.9500
C22—C23	1.3983 (19)	C11—C10	1.389 (2)
C22—C25	1.5068 (17)	C16—H16	0.9500
C23—H23	0.9500	C10—H10	0.9500
C4—H4	0.9500	C25—H25A	0.9800
C4—C5	1.4596 (17)	C25—H25B	0.9800
C14—H14	0.9500	C25—H25C	0.9800
C13—C1—C5	126.87 (11)	C19—C20—H20	119.8
C2—C1—C13	126.04 (12)	C21—C20—C19	120.46 (12)
C2—C1—C5	107.08 (11)	C21—C20—H20	119.8
C24—C19—C6	118.52 (12)	C1—C2—C3	110.16 (11)
C20—C19—C24	117.84 (11)	C1—C2—H2	124.9
C20—C19—C6	123.64 (11)	C3—C2—H2	124.9
C4—C3—C7	126.77 (12)	C13—C18—H18	119.5
C4—C3—C2	107.96 (11)	C17—C18—C13	120.97 (13)
C2—C3—C7	124.93 (11)	C17—C18—H18	119.5
C14—C13—C1	122.49 (12)	C7—C8—H8	119.7
C14—C13—C18	117.84 (12)	C9—C8—C7	120.53 (13)
C18—C13—C1	119.65 (12)	C9—C8—H8	119.7
C19—C24—H24	119.5	C7—C12—H12	119.7
C23—C24—C19	121.01 (12)	C11—C12—C7	120.58 (13)
C23—C24—H24	119.5	C11—C12—H12	119.7
C19—C6—H6	116.0	C18—C17—H17	119.9
C5—C6—C19	127.90 (12)	C18—C17—C16	120.26 (13)
C5—C6—H6	116.0	C16—C17—H17	119.9
C22—C21—H21	119.1	C14—C15—H15	119.8
C20—C21—H21	119.1	C16—C15—C14	120.36 (13)
C20—C21—C22	121.73 (12)	C16—C15—H15	119.8
C21—C22—C23	117.72 (12)	C8—C9—H9	119.8
C21—C22—C25	121.52 (12)	C8—C9—C10	120.40 (13)
C23—C22—C25	120.74 (12)	C10—C9—H9	119.8
C24—C23—C22	121.14 (12)	C12—C11—H11	120.0
C24—C23—H23	119.4	C10—C11—C12	120.09 (13)
C22—C23—H23	119.4	C10—C11—H11	120.0
C3—C4—H4	125.5	C17—C16—H16	120.2
C3—C4—C5	108.96 (11)	C15—C16—C17	119.64 (13)
C5—C4—H4	125.5	C15—C16—H16	120.2
C13—C14—H14	119.6	C9—C10—C11	119.70 (13)
C15—C14—C13	120.87 (13)	C9—C10—H10	120.2
C15—C14—H14	119.6	C11—C10—H10	120.2
C8—C7—C3	120.58 (12)	C22—C25—H25A	109.5
C12—C7—C3	120.70 (12)	C22—C25—H25B	109.5
C12—C7—C8	118.59 (12)	C22—C25—H25C	109.5
C6—C5—C1	125.28 (12)	H25A—C25—H25B	109.5
C6—C5—C4	128.23 (12)	H25A—C25—H25C	109.5
C4—C5—C1	105.78 (10)	H25B—C25—H25C	109.5

Hydrogen-bond geometry (Å, º)

Cg3 and Cg4 are the centroids of the C7–C12 and C19–C24 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cg3^i	0.95	2.95	3.6560 (4)	132
C17—H17···Cg3^ii	0.95	2.83	3.4837 (4)	127
C25—H25A···Cg4^iii	0.98	2.98	3.8277 (4)	145

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

{3-[(2,4,6-Trimethylphenyl)methylidene]-4-phenylcyclopenta-1,4-dien-1-yl}benzene (III)

Crystal data

C27H24	Dx = 1.169 Mg m^−3
Mr = 348.46	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 3728 reflections
a = 30.031 (6) Å	θ = 2.2–22.3°
b = 5.6147 (12) Å	µ = 0.07 mm^−1
c = 23.494 (5) Å	T = 100 K
V = 3961.4 (14) Å^3	Irregular, red
Z = 8	0.26 × 0.11 × 0.10 mm
F(000) = 1488

Data collection

Bruker APEXII CCD diffractometer	5709 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.070
Absorption correction: multi-scan SADABS	θmax = 24.8°, θmin = 2.2°
Tmin = 0.678, Tmax = 0.745	h = −35→35
38475 measured reflections	k = −6→6
6776 independent reflections	l = −27→27

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.043	w = 1/[σ^2(Fo^2) + (0.054P)^2 + 0.3457P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.108	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.17 e Å^−3
6776 reflections	Δρmin = −0.17 e Å^−3
494 parameters	Absolute structure: Refined as an inversion twin.
1 restraint	Absolute structure parameter: −6 (10)
Primary atom site location: dual

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a two-component inversion twin

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.35712 (11)	0.1134 (6)	0.54077 (15)	0.0224 (8)
C2	0.36382 (11)	0.1309 (6)	0.48394 (15)	0.0238 (8)
H2	0.384904	0.045102	0.463428	0.029*
C3	0.33274 (11)	0.3060 (6)	0.45947 (15)	0.0219 (8)
C4	0.30771 (12)	0.3951 (6)	0.50228 (15)	0.0230 (8)
H4	0.286286	0.513761	0.498702	0.028*
C5	0.31988 (11)	0.2742 (6)	0.55511 (15)	0.0227 (8)
C6	0.29829 (11)	0.2883 (6)	0.60543 (15)	0.0239 (8)
H6	0.308796	0.193941	0.635065	0.029*
C7	0.38365 (11)	−0.0333 (6)	0.58024 (14)	0.0225 (8)
C8	0.39541 (11)	0.0453 (6)	0.63499 (15)	0.0245 (8)
H8	0.385132	0.191708	0.648020	0.029*
C9	0.42211 (12)	−0.0930 (6)	0.66963 (16)	0.0274 (8)
H9	0.429090	−0.040616	0.706110	0.033*
C10	0.43847 (12)	−0.3077 (7)	0.65055 (17)	0.0283 (9)
H10	0.456900	−0.398471	0.673806	0.034*
C11	0.42743 (12)	−0.3879 (6)	0.59677 (16)	0.0265 (9)
H11	0.438662	−0.532334	0.583768	0.032*
C12	0.39980 (11)	−0.2547 (6)	0.56223 (15)	0.0227 (8)
H12	0.391827	−0.312675	0.526587	0.027*
C13	0.33002 (11)	0.3610 (6)	0.39856 (15)	0.0216 (8)
C14	0.34639 (11)	0.1972 (6)	0.35861 (14)	0.0243 (8)
H14	0.359649	0.057076	0.371174	0.029*
C15	0.34310 (12)	0.2409 (6)	0.30085 (16)	0.0284 (8)
H15	0.354276	0.130280	0.275078	0.034*
C16	0.32342 (12)	0.4469 (7)	0.28105 (16)	0.0282 (8)
H16	0.321116	0.475127	0.242154	0.034*
C17	0.30710 (12)	0.6115 (7)	0.31990 (16)	0.0291 (9)
H17	0.293684	0.750470	0.306878	0.035*
C18	0.31060 (11)	0.5705 (6)	0.37800 (15)	0.0249 (8)
H18	0.299935	0.683511	0.403522	0.030*
C19	0.25933 (11)	0.4412 (6)	0.61723 (14)	0.0226 (8)
C20	0.26414 (11)	0.6213 (6)	0.65876 (14)	0.0240 (8)
C21	0.22874 (12)	0.7743 (6)	0.66946 (15)	0.0252 (8)
H21	0.232343	0.897102	0.695611	0.030*
C22	0.18814 (12)	0.7477 (6)	0.64199 (15)	0.0249 (8)
C23	0.18351 (11)	0.5641 (6)	0.60303 (15)	0.0248 (8)
H23	0.156118	0.542375	0.585313	0.030*
C24	0.21846 (12)	0.4107 (6)	0.58945 (14)	0.0232 (8)
C25	0.30762 (12)	0.6478 (7)	0.69049 (16)	0.0324 (9)
H25A	0.312022	0.512148	0.714713	0.049*
H25B	0.306771	0.789870	0.713210	0.049*
H25C	0.331689	0.658303	0.663719	0.049*
C26	0.14909 (12)	0.9077 (7)	0.65542 (17)	0.0334 (9)
H26A	0.132792	0.843321	0.687025	0.050*
H26B	0.129912	0.917565	0.622806	0.050*
H26C	0.159736	1.063905	0.664950	0.050*
C27	0.21031 (12)	0.2158 (7)	0.54676 (16)	0.0297 (9)
H27A	0.217207	0.272939	0.509273	0.044*
H27B	0.179610	0.168474	0.548256	0.044*
H27C	0.228897	0.081633	0.555521	0.044*
C28	0.51786 (11)	0.0968 (6)	0.46548 (15)	0.0224 (8)
C29	0.51122 (12)	0.1276 (6)	0.52183 (15)	0.0239 (8)
H29	0.490034	0.047263	0.543401	0.029*
C30	0.54251 (11)	0.3073 (6)	0.54415 (15)	0.0218 (8)
C31	0.56796 (12)	0.3832 (6)	0.50028 (16)	0.0225 (7)
H31	0.589866	0.499884	0.502582	0.027*
C32	0.55572 (11)	0.2536 (6)	0.44875 (15)	0.0229 (8)
C33	0.57550 (11)	0.2587 (6)	0.39746 (15)	0.0243 (8)
H33	0.564527	0.155088	0.369957	0.029*
C34	0.49026 (11)	−0.0516 (6)	0.42789 (15)	0.0223 (8)
C35	0.47587 (11)	0.0308 (6)	0.37476 (15)	0.0246 (8)
H35	0.486290	0.175537	0.360834	0.030*
C36	0.44609 (12)	−0.1027 (6)	0.34279 (16)	0.0278 (9)
H36	0.436917	−0.047288	0.307383	0.033*
C37	0.42992 (12)	−0.3171 (7)	0.36296 (16)	0.0297 (9)
H37	0.409495	−0.403887	0.341633	0.036*
C38	0.44434 (12)	−0.4018 (7)	0.41514 (17)	0.0286 (9)
H38	0.433815	−0.546723	0.428766	0.034*
C39	0.47439 (11)	−0.2711 (6)	0.44707 (16)	0.0245 (8)
H39	0.484165	−0.330463	0.481852	0.029*
C40	0.54362 (11)	0.3803 (6)	0.60410 (15)	0.0217 (8)
C41	0.56288 (11)	0.5974 (7)	0.62138 (15)	0.0248 (8)
H41	0.574388	0.700735	0.594173	0.030*
C42	0.56484 (12)	0.6580 (7)	0.67802 (16)	0.0267 (9)
H42	0.578045	0.800994	0.688734	0.032*
C43	0.54749 (12)	0.5096 (6)	0.71904 (16)	0.0278 (9)
H43	0.548967	0.551985	0.757264	0.033*
C44	0.52781 (11)	0.2968 (6)	0.70301 (15)	0.0253 (8)
H44	0.516058	0.195981	0.730586	0.030*
C45	0.52556 (11)	0.2335 (6)	0.64608 (15)	0.0234 (8)
H45	0.511850	0.091446	0.635730	0.028*
C46	0.61314 (11)	0.4139 (6)	0.38060 (14)	0.0223 (8)
C47	0.65574 (11)	0.3931 (6)	0.40497 (14)	0.0241 (8)
C48	0.68915 (12)	0.5477 (6)	0.38677 (16)	0.0278 (9)
H48	0.717337	0.534982	0.402891	0.033*
C49	0.68188 (12)	0.7189 (7)	0.34564 (16)	0.0280 (9)
C50	0.63963 (12)	0.7337 (7)	0.32137 (16)	0.0293 (9)
H50	0.634253	0.847371	0.293421	0.035*
C51	0.60570 (12)	0.5842 (7)	0.33773 (15)	0.0269 (8)
C52	0.66681 (12)	0.2043 (7)	0.44841 (16)	0.0309 (9)
H52A	0.657021	0.255505	0.485335	0.046*
H52B	0.698413	0.178763	0.449049	0.046*
H52C	0.652035	0.058469	0.438490	0.046*
C53	0.71847 (13)	0.8856 (7)	0.32675 (19)	0.0387 (10)
H53A	0.743758	0.867604	0.351372	0.058*
H53B	0.707971	1.046960	0.328511	0.058*
H53C	0.726934	0.848305	0.288375	0.058*
C54	0.56037 (13)	0.6030 (8)	0.31041 (18)	0.0379 (11)
H54A	0.553643	0.457151	0.290898	0.057*
H54B	0.560283	0.732458	0.283720	0.057*
H54C	0.538341	0.631357	0.339236	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0209 (18)	0.0218 (18)	0.024 (2)	0.0005 (15)	0.0000 (15)	0.0015 (15)
C2	0.0235 (19)	0.0217 (19)	0.026 (2)	0.0025 (15)	0.0021 (16)	−0.0005 (15)
C3	0.0194 (18)	0.0227 (18)	0.024 (2)	0.0005 (15)	0.0014 (15)	0.0014 (15)
C4	0.0218 (18)	0.0215 (17)	0.026 (2)	0.0006 (15)	0.0007 (15)	0.0027 (15)
C5	0.0232 (18)	0.0238 (18)	0.021 (2)	−0.0012 (15)	0.0015 (15)	−0.0014 (15)
C6	0.025 (2)	0.0218 (18)	0.024 (2)	0.0012 (15)	0.0000 (15)	0.0042 (15)
C7	0.0178 (18)	0.0255 (18)	0.024 (2)	−0.0006 (14)	0.0032 (15)	0.0024 (16)
C8	0.0217 (19)	0.0255 (19)	0.026 (2)	−0.0013 (16)	0.0035 (15)	−0.0010 (15)
C9	0.0249 (19)	0.033 (2)	0.024 (2)	−0.0015 (17)	−0.0045 (16)	0.0000 (16)
C10	0.023 (2)	0.028 (2)	0.034 (2)	−0.0005 (16)	−0.0048 (16)	0.0067 (18)
C11	0.0246 (19)	0.0224 (19)	0.033 (2)	0.0018 (15)	0.0059 (17)	0.0008 (16)
C12	0.0218 (18)	0.0229 (18)	0.0233 (19)	−0.0002 (15)	0.0012 (15)	0.0013 (14)
C13	0.0159 (18)	0.0250 (18)	0.024 (2)	−0.0023 (14)	0.0020 (14)	0.0008 (14)
C14	0.022 (2)	0.0250 (18)	0.026 (2)	0.0012 (16)	0.0016 (15)	0.0008 (15)
C15	0.0273 (19)	0.030 (2)	0.028 (2)	0.0013 (16)	0.0027 (16)	−0.0023 (16)
C16	0.030 (2)	0.033 (2)	0.022 (2)	−0.0028 (17)	0.0019 (16)	0.0058 (16)
C17	0.027 (2)	0.031 (2)	0.029 (2)	0.0029 (17)	−0.0010 (16)	0.0074 (17)
C18	0.0204 (18)	0.0273 (19)	0.027 (2)	0.0004 (16)	0.0011 (15)	0.0026 (16)
C19	0.0205 (18)	0.0255 (19)	0.0218 (19)	0.0006 (15)	0.0038 (14)	0.0049 (15)
C20	0.0234 (19)	0.0287 (19)	0.020 (2)	−0.0038 (15)	0.0025 (15)	0.0024 (15)
C21	0.029 (2)	0.0262 (19)	0.0208 (19)	−0.0031 (16)	0.0045 (16)	−0.0011 (15)
C22	0.0245 (19)	0.0249 (19)	0.025 (2)	0.0004 (16)	0.0049 (16)	0.0018 (15)
C23	0.0200 (18)	0.0301 (19)	0.024 (2)	−0.0034 (15)	−0.0018 (15)	0.0033 (16)
C24	0.0276 (19)	0.0245 (18)	0.0176 (19)	−0.0023 (15)	0.0012 (15)	0.0029 (15)
C25	0.028 (2)	0.038 (2)	0.031 (2)	−0.0038 (18)	0.0002 (17)	−0.0023 (18)
C26	0.028 (2)	0.034 (2)	0.038 (2)	0.0049 (18)	0.0055 (18)	−0.0015 (18)
C27	0.027 (2)	0.035 (2)	0.027 (2)	−0.0030 (17)	−0.0005 (17)	−0.0029 (17)
C28	0.0218 (18)	0.0222 (18)	0.023 (2)	−0.0003 (15)	−0.0001 (15)	−0.0016 (15)
C29	0.0216 (19)	0.0259 (19)	0.024 (2)	−0.0019 (15)	0.0032 (15)	0.0028 (15)
C30	0.0209 (19)	0.0213 (18)	0.023 (2)	−0.0001 (15)	−0.0021 (15)	−0.0006 (15)
C31	0.0212 (18)	0.0220 (16)	0.0242 (19)	−0.0022 (16)	−0.0033 (14)	−0.0014 (17)
C32	0.0203 (18)	0.0241 (19)	0.024 (2)	0.0014 (15)	−0.0003 (15)	0.0011 (14)
C33	0.0201 (19)	0.031 (2)	0.022 (2)	0.0037 (16)	−0.0020 (15)	−0.0030 (16)
C34	0.0201 (18)	0.0234 (18)	0.0235 (19)	0.0018 (15)	0.0029 (15)	−0.0035 (15)
C35	0.0213 (19)	0.0252 (18)	0.027 (2)	0.0003 (15)	0.0023 (15)	−0.0038 (16)
C36	0.0229 (19)	0.035 (2)	0.025 (2)	0.0047 (17)	0.0005 (16)	−0.0074 (16)
C37	0.0205 (19)	0.035 (2)	0.034 (2)	−0.0042 (17)	0.0019 (16)	−0.0136 (18)
C38	0.0235 (19)	0.025 (2)	0.038 (2)	−0.0033 (16)	0.0050 (17)	−0.0067 (17)
C39	0.0211 (18)	0.028 (2)	0.024 (2)	−0.0001 (15)	0.0024 (15)	−0.0016 (15)
C40	0.0195 (18)	0.0255 (19)	0.0200 (19)	0.0028 (15)	−0.0020 (15)	−0.0003 (15)
C41	0.0234 (19)	0.0266 (19)	0.024 (2)	−0.0042 (15)	0.0003 (15)	0.0033 (15)
C42	0.025 (2)	0.027 (2)	0.028 (2)	−0.0017 (16)	−0.0009 (16)	−0.0023 (16)
C43	0.025 (2)	0.037 (2)	0.022 (2)	0.0038 (17)	−0.0031 (15)	−0.0020 (17)
C44	0.0213 (18)	0.034 (2)	0.020 (2)	0.0024 (16)	0.0010 (15)	0.0040 (16)
C45	0.0186 (19)	0.0277 (19)	0.024 (2)	−0.0007 (15)	−0.0008 (15)	0.0010 (16)
C46	0.0243 (19)	0.0253 (19)	0.0172 (19)	−0.0003 (15)	0.0020 (15)	−0.0018 (15)
C47	0.0215 (19)	0.028 (2)	0.023 (2)	0.0029 (16)	0.0035 (15)	0.0007 (15)
C48	0.0195 (19)	0.031 (2)	0.033 (2)	0.0033 (16)	0.0000 (16)	−0.0014 (17)
C49	0.023 (2)	0.028 (2)	0.032 (2)	0.0012 (16)	0.0062 (16)	0.0000 (17)
C50	0.028 (2)	0.031 (2)	0.028 (2)	0.0054 (17)	0.0064 (16)	0.0085 (16)
C51	0.0230 (19)	0.034 (2)	0.024 (2)	0.0043 (16)	0.0009 (15)	0.0014 (16)
C52	0.025 (2)	0.035 (2)	0.032 (2)	0.0035 (17)	−0.0031 (17)	0.0060 (17)
C53	0.033 (2)	0.035 (2)	0.047 (3)	−0.0041 (18)	0.0066 (19)	0.009 (2)
C54	0.028 (2)	0.049 (3)	0.037 (3)	−0.0001 (19)	−0.0065 (18)	0.014 (2)

Geometric parameters (Å, º)

C1—C2	1.354 (5)	C28—C29	1.350 (5)
C1—C5	1.476 (5)	C28—C32	1.491 (5)
C1—C7	1.474 (5)	C28—C34	1.470 (5)
C2—H2	0.9300	C29—H29	0.9300
C2—C3	1.473 (5)	C29—C30	1.475 (5)
C3—C4	1.352 (5)	C30—C31	1.352 (5)
C3—C13	1.466 (5)	C30—C40	1.467 (5)
C4—H4	0.9300	C31—H31	0.9300
C4—C5	1.461 (5)	C31—C32	1.460 (5)
C5—C6	1.351 (5)	C32—C33	1.344 (5)
C6—H6	0.9300	C33—H33	0.9300
C6—C19	1.478 (5)	C33—C46	1.481 (5)
C7—C8	1.405 (5)	C34—C35	1.400 (5)
C7—C12	1.400 (5)	C34—C39	1.396 (5)
C8—H8	0.9300	C35—H35	0.9300
C8—C9	1.381 (5)	C35—C36	1.388 (5)
C9—H9	0.9300	C36—H36	0.9300
C9—C10	1.377 (5)	C36—C37	1.382 (5)
C10—H10	0.9300	C37—H37	0.9300
C10—C11	1.382 (6)	C37—C38	1.384 (5)
C11—H11	0.9300	C38—H38	0.9300
C11—C12	1.381 (5)	C38—C39	1.384 (5)
C12—H12	0.9300	C39—H39	0.9300
C13—C14	1.403 (5)	C40—C41	1.409 (5)
C13—C18	1.399 (5)	C40—C45	1.395 (5)
C14—H14	0.9300	C41—H41	0.9300
C14—C15	1.382 (5)	C41—C42	1.375 (5)
C15—H15	0.9300	C42—H42	0.9300
C15—C16	1.380 (5)	C42—C43	1.376 (5)
C16—H16	0.9300	C43—H43	0.9300
C16—C17	1.388 (5)	C43—C44	1.385 (5)
C17—H17	0.9300	C44—H44	0.9300
C17—C18	1.388 (5)	C44—C45	1.386 (5)
C18—H18	0.9300	C45—H45	0.9300
C19—C20	1.412 (5)	C46—C47	1.407 (5)
C19—C24	1.401 (5)	C46—C51	1.407 (5)
C20—C21	1.390 (5)	C47—C48	1.394 (5)
C20—C25	1.511 (5)	C47—C52	1.509 (5)
C21—H21	0.9300	C48—H48	0.9300
C21—C22	1.388 (5)	C48—C49	1.381 (5)
C22—C23	1.386 (5)	C49—C50	1.393 (5)
C22—C26	1.510 (5)	C49—C53	1.510 (5)
C23—H23	0.9300	C50—H50	0.9300
C23—C24	1.395 (5)	C50—C51	1.375 (5)
C24—C27	1.505 (5)	C51—C54	1.509 (5)
C25—H25A	0.9600	C52—H52A	0.9600
C25—H25B	0.9600	C52—H52B	0.9600
C25—H25C	0.9600	C52—H52C	0.9600
C26—H26A	0.9600	C53—H53A	0.9600
C26—H26B	0.9600	C53—H53B	0.9600
C26—H26C	0.9600	C53—H53C	0.9600
C27—H27A	0.9600	C54—H54A	0.9600
C27—H27B	0.9600	C54—H54B	0.9600
C27—H27C	0.9600	C54—H54C	0.9600
C2—C1—C5	107.1 (3)	C29—C28—C32	107.2 (3)
C2—C1—C7	125.5 (3)	C29—C28—C34	125.3 (3)
C7—C1—C5	127.4 (3)	C34—C28—C32	127.3 (3)
C1—C2—H2	125.1	C28—C29—H29	125.0
C1—C2—C3	109.8 (3)	C28—C29—C30	110.0 (3)
C3—C2—H2	125.1	C30—C29—H29	125.0
C4—C3—C2	108.0 (3)	C31—C30—C29	107.7 (3)
C4—C3—C13	128.1 (3)	C31—C30—C40	129.1 (3)
C13—C3—C2	123.9 (3)	C40—C30—C29	123.1 (3)
C3—C4—H4	125.6	C30—C31—H31	125.3
C3—C4—C5	108.7 (3)	C30—C31—C32	109.4 (3)
C5—C4—H4	125.6	C32—C31—H31	125.3
C4—C5—C1	106.2 (3)	C31—C32—C28	105.5 (3)
C6—C5—C1	126.8 (3)	C33—C32—C28	125.9 (3)
C6—C5—C4	126.6 (3)	C33—C32—C31	128.4 (3)
C5—C6—H6	117.3	C32—C33—H33	116.9
C5—C6—C19	125.3 (3)	C32—C33—C46	126.2 (3)
C19—C6—H6	117.3	C46—C33—H33	116.9
C8—C7—C1	122.4 (3)	C35—C34—C28	121.5 (3)
C12—C7—C1	119.6 (3)	C39—C34—C28	119.9 (3)
C12—C7—C8	117.9 (3)	C39—C34—C35	118.3 (3)
C7—C8—H8	119.7	C34—C35—H35	119.9
C9—C8—C7	120.6 (3)	C36—C35—C34	120.2 (3)
C9—C8—H8	119.7	C36—C35—H35	119.9
C8—C9—H9	119.8	C35—C36—H36	119.6
C10—C9—C8	120.5 (4)	C37—C36—C35	120.8 (4)
C10—C9—H9	119.8	C37—C36—H36	119.6
C9—C10—H10	120.1	C36—C37—H37	120.2
C9—C10—C11	119.8 (4)	C36—C37—C38	119.5 (3)
C11—C10—H10	120.1	C38—C37—H37	120.2
C10—C11—H11	119.8	C37—C38—H38	119.9
C12—C11—C10	120.3 (3)	C39—C38—C37	120.1 (4)
C12—C11—H11	119.8	C39—C38—H38	119.9
C7—C12—H12	119.6	C34—C39—H39	119.5
C11—C12—C7	120.8 (3)	C38—C39—C34	121.0 (3)
C11—C12—H12	119.6	C38—C39—H39	119.5
C14—C13—C3	119.7 (3)	C41—C40—C30	121.8 (3)
C18—C13—C3	122.5 (3)	C45—C40—C30	120.3 (3)
C18—C13—C14	117.8 (3)	C45—C40—C41	117.8 (3)
C13—C14—H14	119.5	C40—C41—H41	119.6
C15—C14—C13	121.0 (3)	C42—C41—C40	120.7 (3)
C15—C14—H14	119.5	C42—C41—H41	119.6
C14—C15—H15	119.7	C41—C42—H42	119.6
C16—C15—C14	120.7 (4)	C41—C42—C43	120.8 (3)
C16—C15—H15	119.7	C43—C42—H42	119.6
C15—C16—H16	120.4	C42—C43—H43	120.2
C15—C16—C17	119.2 (4)	C42—C43—C44	119.6 (3)
C17—C16—H16	120.4	C44—C43—H43	120.2
C16—C17—H17	119.7	C43—C44—H44	119.8
C16—C17—C18	120.6 (3)	C43—C44—C45	120.3 (3)
C18—C17—H17	119.7	C45—C44—H44	119.8
C13—C18—H18	119.6	C40—C45—H45	119.6
C17—C18—C13	120.7 (3)	C44—C45—C40	120.8 (3)
C17—C18—H18	119.6	C44—C45—H45	119.6
C20—C19—C6	117.7 (3)	C47—C46—C33	122.4 (3)
C24—C19—C6	122.4 (3)	C47—C46—C51	119.5 (3)
C24—C19—C20	119.9 (3)	C51—C46—C33	118.1 (3)
C19—C20—C25	120.0 (3)	C46—C47—C52	122.3 (3)
C21—C20—C19	119.3 (3)	C48—C47—C46	118.6 (3)
C21—C20—C25	120.7 (3)	C48—C47—C52	119.1 (3)
C20—C21—H21	119.3	C47—C48—H48	118.8
C22—C21—C20	121.5 (3)	C49—C48—C47	122.3 (3)
C22—C21—H21	119.3	C49—C48—H48	118.8
C21—C22—C26	121.4 (3)	C48—C49—C50	118.2 (3)
C23—C22—C21	118.4 (3)	C48—C49—C53	121.5 (3)
C23—C22—C26	120.2 (3)	C50—C49—C53	120.4 (3)
C22—C23—H23	118.8	C49—C50—H50	119.2
C22—C23—C24	122.4 (3)	C51—C50—C49	121.6 (3)
C24—C23—H23	118.8	C51—C50—H50	119.2
C19—C24—C27	122.8 (3)	C46—C51—C54	119.7 (3)
C23—C24—C19	118.5 (3)	C50—C51—C46	119.8 (3)
C23—C24—C27	118.6 (3)	C50—C51—C54	120.5 (3)
C20—C25—H25A	109.5	C47—C52—H52A	109.5
C20—C25—H25B	109.5	C47—C52—H52B	109.5
C20—C25—H25C	109.5	C47—C52—H52C	109.5
H25A—C25—H25B	109.5	H52A—C52—H52B	109.5
H25A—C25—H25C	109.5	H52A—C52—H52C	109.5
H25B—C25—H25C	109.5	H52B—C52—H52C	109.5
C22—C26—H26A	109.5	C49—C53—H53A	109.5
C22—C26—H26B	109.5	C49—C53—H53B	109.5
C22—C26—H26C	109.5	C49—C53—H53C	109.5
H26A—C26—H26B	109.5	H53A—C53—H53B	109.5
H26A—C26—H26C	109.5	H53A—C53—H53C	109.5
H26B—C26—H26C	109.5	H53B—C53—H53C	109.5
C24—C27—H27A	109.5	C51—C54—H54A	109.5
C24—C27—H27B	109.5	C51—C54—H54B	109.5
C24—C27—H27C	109.5	C51—C54—H54C	109.5
H27A—C27—H27B	109.5	H54A—C54—H54B	109.5
H27A—C27—H27C	109.5	H54A—C54—H54C	109.5
H27B—C27—H27C	109.5	H54B—C54—H54C	109.5

Hydrogen-bond geometry (Å, º)

Cg5, Cg6, Cg7, Cg8, and Cg9 are the centroids of the C40–C45, C7–C12, C13–C18, C28–C32, and C34–C39 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cg5^i	0.93	2.81	3.5059 (7)	132
C25—H25C···Cg6^ii	0.96	2.81	3.7115 (8)	158
C37—H37···Cg7^iii	0.93	2.71	3.5129 (8)	145
C39—H39···Cg8^ii	0.93	2.97	3.5817 (8)	125
C53—H53A···Cg7^iv	0.96	2.94	3.6503 (8)	132
C54—H54C···Cg9^v	0.96	2.88	3.7983 (8)	160

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

{3-[(2,3,4,5,6-Pentamethylphenyl)methylidene]-4-phenylcyclopenta-1,4-dien-1-yl}benzene (IV)

Crystal data

C29H28	F(000) = 1616
Mr = 376.51	Dx = 1.183 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 30.987 (7) Å	Cell parameters from 3475 reflections
b = 5.8273 (14) Å	θ = 2.3–26.2°
c = 23.557 (6) Å	µ = 0.07 mm^−1
β = 96.192 (3)°	T = 100 K
V = 4228.9 (17) Å^3	Needle, orange
Z = 8	0.44 × 0.11 × 0.1 mm

Data collection

Bruker APEXII CCD diffractometer	3213 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.082
Absorption correction: multi-scan SADABS	θmax = 26.5°, θmin = 2.1°
Tmin = 0.587, Tmax = 0.745	h = −38→38
37965 measured reflections	k = −7→7
4394 independent reflections	l = −29→29

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.137	w = 1/[σ^2(Fo^2) + (0.0562P)^2 + 4.4117P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
4394 reflections	Δρmax = 0.24 e Å^−3
267 parameters	Δρmin = −0.22 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C13	0.59242 (5)	0.5116 (3)	0.64414 (7)	0.0214 (4)
C7	0.55646 (5)	0.0887 (3)	0.82183 (7)	0.0213 (4)
C19	0.67937 (5)	0.5436 (3)	0.86724 (7)	0.0214 (4)
C5	0.61684 (5)	0.3893 (3)	0.79995 (7)	0.0221 (4)
C20	0.67537 (6)	0.7194 (3)	0.90741 (7)	0.0221 (4)
C4	0.62469 (6)	0.5125 (3)	0.74821 (7)	0.0228 (4)
H4	0.646359	0.626148	0.745542	0.027*
C14	0.57411 (6)	0.3657 (3)	0.60104 (7)	0.0242 (4)
H14	0.563145	0.220269	0.610728	0.029*
C12	0.54703 (5)	0.1649 (3)	0.87570 (7)	0.0229 (4)
H12	0.556500	0.312444	0.888929	0.027*
C8	0.54204 (5)	−0.1290 (3)	0.80385 (7)	0.0233 (4)
H8	0.548662	−0.185405	0.767949	0.028*
C3	0.59587 (5)	0.4381 (3)	0.70428 (7)	0.0216 (4)
C1	0.57895 (5)	0.2366 (3)	0.78360 (7)	0.0222 (4)
C2	0.56767 (5)	0.2650 (3)	0.72698 (7)	0.0221 (4)
H2	0.544904	0.185041	0.705081	0.026*
C18	0.60730 (6)	0.7271 (3)	0.62895 (7)	0.0241 (4)
H18	0.618881	0.830511	0.657840	0.029*
C6	0.64079 (6)	0.3964 (3)	0.85109 (7)	0.0230 (4)
H6	0.632173	0.297150	0.879814	0.028*
C24	0.71917 (6)	0.5018 (3)	0.84579 (7)	0.0247 (4)
C23	0.75536 (6)	0.6403 (3)	0.86477 (7)	0.0259 (4)
C10	0.50940 (6)	−0.1886 (3)	0.89086 (8)	0.0273 (4)
H10	0.493552	−0.282816	0.914192	0.033*
C11	0.52397 (6)	0.0264 (3)	0.90983 (7)	0.0257 (4)
H11	0.518138	0.079165	0.946387	0.031*
C16	0.58769 (6)	0.6439 (3)	0.52940 (7)	0.0279 (4)
H16	0.586508	0.687795	0.490425	0.033*
C21	0.71147 (6)	0.8557 (3)	0.92605 (7)	0.0241 (4)
C9	0.51823 (6)	−0.2643 (3)	0.83749 (8)	0.0263 (4)
H9	0.507883	−0.409838	0.823913	0.032*
C22	0.75145 (6)	0.8155 (3)	0.90470 (7)	0.0258 (4)
C15	0.57181 (6)	0.4318 (3)	0.54404 (7)	0.0273 (4)
H15	0.559312	0.331309	0.515037	0.033*
C25	0.63232 (6)	0.7587 (3)	0.93028 (8)	0.0274 (4)
H25A	0.634909	0.720712	0.971033	0.041*
H25B	0.610176	0.660797	0.909650	0.041*
H25C	0.623921	0.920034	0.925004	0.041*
C17	0.60526 (6)	0.7913 (3)	0.57185 (7)	0.0262 (4)
H17	0.615984	0.936980	0.561929	0.031*
C29	0.72431 (6)	0.3065 (4)	0.80483 (8)	0.0315 (5)
H29A	0.697383	0.217050	0.799632	0.047*
H29B	0.748259	0.207275	0.820370	0.047*
H29C	0.730603	0.368437	0.767938	0.047*
C26	0.70788 (6)	1.0445 (3)	0.96918 (8)	0.0323 (5)
H26A	0.728286	1.014941	1.003141	0.048*
H26B	0.678224	1.049016	0.979974	0.048*
H26C	0.714808	1.192160	0.952417	0.048*
C28	0.79882 (6)	0.5958 (4)	0.84287 (8)	0.0361 (5)
H28A	0.810760	0.740673	0.830322	0.054*
H28B	0.794943	0.488770	0.810634	0.054*
H28C	0.818874	0.529184	0.873492	0.054*
C27	0.79006 (6)	0.9625 (4)	0.92679 (8)	0.0353 (5)
H27A	0.796079	0.942774	0.968195	0.053*
H27B	0.783513	1.124120	0.918115	0.053*
H27C	0.815519	0.915727	0.908311	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C13	0.0167 (8)	0.0278 (10)	0.0198 (8)	0.0020 (7)	0.0020 (7)	0.0000 (7)
C7	0.0150 (8)	0.0271 (9)	0.0210 (8)	−0.0010 (7)	−0.0020 (7)	0.0029 (7)
C19	0.0204 (9)	0.0265 (9)	0.0164 (8)	−0.0024 (7)	−0.0016 (7)	0.0039 (7)
C5	0.0197 (9)	0.0242 (9)	0.0222 (9)	−0.0013 (7)	0.0009 (7)	−0.0007 (7)
C20	0.0216 (9)	0.0257 (9)	0.0182 (8)	−0.0012 (7)	−0.0015 (7)	0.0046 (7)
C4	0.0203 (9)	0.0263 (9)	0.0215 (9)	−0.0013 (7)	0.0019 (7)	0.0020 (7)
C14	0.0212 (9)	0.0273 (10)	0.0242 (9)	0.0018 (7)	0.0027 (7)	−0.0006 (7)
C12	0.0196 (9)	0.0258 (9)	0.0224 (9)	−0.0016 (7)	−0.0022 (7)	0.0006 (7)
C8	0.0198 (9)	0.0264 (10)	0.0232 (9)	0.0009 (7)	−0.0003 (7)	0.0012 (7)
C3	0.0205 (9)	0.0229 (9)	0.0216 (9)	0.0015 (7)	0.0033 (7)	0.0004 (7)
C1	0.0205 (9)	0.0250 (9)	0.0208 (9)	−0.0005 (7)	0.0009 (7)	0.0000 (7)
C2	0.0190 (9)	0.0258 (9)	0.0210 (8)	−0.0018 (7)	0.0000 (7)	−0.0019 (7)
C18	0.0225 (9)	0.0275 (10)	0.0219 (9)	0.0007 (8)	0.0011 (7)	−0.0005 (7)
C6	0.0228 (9)	0.0257 (9)	0.0204 (8)	−0.0028 (7)	0.0018 (7)	0.0021 (7)
C24	0.0240 (9)	0.0301 (10)	0.0191 (8)	0.0002 (8)	−0.0016 (7)	0.0044 (7)
C23	0.0197 (9)	0.0344 (11)	0.0231 (9)	−0.0015 (8)	−0.0004 (7)	0.0067 (8)
C10	0.0195 (9)	0.0336 (11)	0.0283 (10)	−0.0031 (8)	0.0002 (7)	0.0079 (8)
C11	0.0204 (9)	0.0350 (11)	0.0217 (9)	0.0010 (8)	0.0015 (7)	0.0013 (8)
C16	0.0276 (10)	0.0373 (11)	0.0190 (9)	0.0081 (8)	0.0035 (7)	0.0040 (8)
C21	0.0245 (9)	0.0261 (10)	0.0206 (8)	−0.0023 (8)	−0.0025 (7)	0.0043 (7)
C9	0.0227 (9)	0.0238 (10)	0.0312 (10)	−0.0034 (7)	−0.0033 (8)	0.0028 (8)
C22	0.0207 (9)	0.0316 (10)	0.0238 (9)	−0.0042 (8)	−0.0037 (7)	0.0069 (8)
C15	0.0245 (9)	0.0362 (11)	0.0208 (9)	0.0040 (8)	0.0001 (7)	−0.0049 (8)
C25	0.0211 (9)	0.0343 (11)	0.0265 (9)	−0.0006 (8)	0.0012 (7)	0.0012 (8)
C17	0.0234 (9)	0.0300 (10)	0.0255 (9)	0.0028 (8)	0.0047 (7)	0.0049 (8)
C29	0.0275 (10)	0.0393 (12)	0.0274 (10)	0.0010 (9)	0.0016 (8)	−0.0027 (8)
C26	0.0303 (10)	0.0333 (11)	0.0321 (10)	−0.0053 (9)	−0.0025 (8)	−0.0029 (8)
C28	0.0234 (10)	0.0534 (14)	0.0315 (10)	0.0003 (9)	0.0026 (8)	0.0057 (10)
C27	0.0271 (10)	0.0425 (12)	0.0350 (11)	−0.0111 (9)	−0.0025 (8)	0.0037 (9)

Geometric parameters (Å, º)

C13—C14	1.397 (2)	C23—C22	1.402 (3)
C13—C3	1.473 (2)	C23—C28	1.516 (3)
C13—C18	1.397 (3)	C10—H10	0.9500
C7—C12	1.405 (2)	C10—C11	1.389 (3)
C7—C8	1.396 (3)	C10—C9	1.387 (3)
C7—C1	1.475 (2)	C11—H11	0.9500
C19—C20	1.409 (2)	C16—H16	0.9500
C19—C6	1.487 (2)	C16—C15	1.388 (3)
C19—C24	1.404 (2)	C16—C17	1.384 (3)
C5—C4	1.457 (2)	C21—C22	1.406 (3)
C5—C1	1.490 (2)	C21—C26	1.510 (3)
C5—C6	1.346 (2)	C9—H9	0.9500
C20—C21	1.403 (2)	C22—C27	1.517 (3)
C20—C25	1.509 (2)	C15—H15	0.9500
C4—H4	0.9500	C25—H25A	0.9800
C4—C3	1.363 (2)	C25—H25B	0.9800
C14—H14	0.9500	C25—H25C	0.9800
C14—C15	1.391 (2)	C17—H17	0.9500
C12—H12	0.9500	C29—H29A	0.9800
C12—C11	1.390 (2)	C29—H29B	0.9800
C8—H8	0.9500	C29—H29C	0.9800
C8—C9	1.386 (2)	C26—H26A	0.9800
C3—C2	1.472 (2)	C26—H26B	0.9800
C1—C2	1.352 (2)	C26—H26C	0.9800
C2—H2	0.9500	C28—H28A	0.9800
C18—H18	0.9500	C28—H28B	0.9800
C18—C17	1.391 (2)	C28—H28C	0.9800
C6—H6	0.9500	C27—H27A	0.9800
C24—C23	1.415 (3)	C27—H27B	0.9800
C24—C29	1.511 (3)	C27—H27C	0.9800
C14—C13—C3	120.24 (16)	C12—C11—H11	119.8
C14—C13—C18	118.70 (16)	C10—C11—C12	120.48 (17)
C18—C13—C3	121.06 (16)	C10—C11—H11	119.8
C12—C7—C1	121.66 (16)	C15—C16—H16	120.1
C8—C7—C12	118.08 (16)	C17—C16—H16	120.1
C8—C7—C1	120.18 (16)	C17—C16—C15	119.70 (17)
C20—C19—C6	117.68 (15)	C20—C21—C22	119.81 (17)
C24—C19—C20	120.83 (16)	C20—C21—C26	120.60 (16)
C24—C19—C6	121.39 (16)	C22—C21—C26	119.59 (16)
C4—C5—C1	106.01 (14)	C8—C9—C10	120.46 (17)
C6—C5—C4	127.44 (16)	C8—C9—H9	119.8
C6—C5—C1	126.35 (16)	C10—C9—H9	119.8
C19—C20—C25	119.69 (16)	C23—C22—C21	120.30 (16)
C21—C20—C19	119.79 (16)	C23—C22—C27	121.28 (17)
C21—C20—C25	120.52 (16)	C21—C22—C27	118.42 (17)
C5—C4—H4	125.6	C14—C15—H15	119.9
C3—C4—C5	108.87 (16)	C16—C15—C14	120.25 (17)
C3—C4—H4	125.6	C16—C15—H15	119.9
C13—C14—H14	119.8	C20—C25—H25A	109.5
C15—C14—C13	120.50 (18)	C20—C25—H25B	109.5
C15—C14—H14	119.8	C20—C25—H25C	109.5
C7—C12—H12	119.7	H25A—C25—H25B	109.5
C11—C12—C7	120.59 (17)	H25A—C25—H25C	109.5
C11—C12—H12	119.7	H25B—C25—H25C	109.5
C7—C8—H8	119.5	C18—C17—H17	119.8
C9—C8—C7	121.08 (17)	C16—C17—C18	120.32 (18)
C9—C8—H8	119.5	C16—C17—H17	119.8
C4—C3—C13	127.69 (16)	C24—C29—H29A	109.5
C4—C3—C2	107.95 (15)	C24—C29—H29B	109.5
C2—C3—C13	124.37 (15)	C24—C29—H29C	109.5
C7—C1—C5	127.02 (15)	H29A—C29—H29B	109.5
C2—C1—C7	125.79 (16)	H29A—C29—H29C	109.5
C2—C1—C5	107.15 (15)	H29B—C29—H29C	109.5
C3—C2—H2	125.0	C21—C26—H26A	109.5
C1—C2—C3	109.98 (15)	C21—C26—H26B	109.5
C1—C2—H2	125.0	C21—C26—H26C	109.5
C13—C18—H18	119.8	H26A—C26—H26B	109.5
C17—C18—C13	120.49 (17)	H26A—C26—H26C	109.5
C17—C18—H18	119.8	H26B—C26—H26C	109.5
C19—C6—H6	116.7	C23—C28—H28A	109.5
C5—C6—C19	126.66 (16)	C23—C28—H28B	109.5
C5—C6—H6	116.7	C23—C28—H28C	109.5
C19—C24—C23	118.97 (17)	H28A—C28—H28B	109.5
C19—C24—C29	121.18 (16)	H28A—C28—H28C	109.5
C23—C24—C29	119.81 (16)	H28B—C28—H28C	109.5
C24—C23—C28	119.87 (17)	C22—C27—H27A	109.5
C22—C23—C24	120.31 (17)	C22—C27—H27B	109.5
C22—C23—C28	119.81 (17)	C22—C27—H27C	109.5
C11—C10—H10	120.4	H27A—C27—H27B	109.5
C9—C10—H10	120.4	H27A—C27—H27C	109.5
C9—C10—C11	119.27 (17)	H27B—C27—H27C	109.5
C13—C14—C15—C16	−0.1 (3)	C3—C13—C18—C17	177.71 (16)
C13—C3—C2—C1	−179.76 (16)	C1—C7—C12—C11	176.90 (16)
C13—C18—C17—C16	1.2 (3)	C1—C7—C8—C9	−175.49 (16)
C7—C12—C11—C10	−0.8 (3)	C1—C5—C4—C3	−1.99 (19)
C7—C8—C9—C10	−2.1 (3)	C1—C5—C6—C19	178.18 (17)
C7—C1—C2—C3	175.98 (16)	C18—C13—C14—C15	1.7 (3)
C19—C20—C21—C22	−0.3 (2)	C18—C13—C3—C4	−25.0 (3)
C19—C20—C21—C26	−179.85 (16)	C18—C13—C3—C2	155.29 (17)
C19—C24—C23—C22	0.4 (3)	C6—C19—C20—C21	176.97 (15)
C19—C24—C23—C28	179.05 (16)	C6—C19—C20—C25	−2.7 (2)
C5—C4—C3—C13	−178.73 (16)	C6—C19—C24—C23	−176.92 (16)
C5—C4—C3—C2	1.0 (2)	C6—C19—C24—C29	0.7 (3)
C5—C1—C2—C3	−1.7 (2)	C6—C5—C4—C3	173.08 (18)
C20—C19—C6—C5	112.0 (2)	C6—C5—C1—C7	9.5 (3)
C20—C19—C24—C23	−0.5 (3)	C6—C5—C1—C2	−172.87 (18)
C20—C19—C24—C29	177.06 (16)	C24—C19—C20—C21	0.4 (2)
C20—C21—C22—C23	0.2 (3)	C24—C19—C20—C25	−179.27 (16)
C20—C21—C22—C27	−178.62 (16)	C24—C19—C6—C5	−71.5 (3)
C4—C5—C1—C7	−175.40 (16)	C24—C23—C22—C21	−0.3 (3)
C4—C5—C1—C2	2.27 (19)	C24—C23—C22—C27	178.50 (16)
C4—C5—C6—C19	4.1 (3)	C11—C10—C9—C8	1.2 (3)
C4—C3—C2—C1	0.5 (2)	C9—C10—C11—C12	0.2 (3)
C14—C13—C3—C4	154.94 (18)	C15—C16—C17—C18	0.4 (3)
C14—C13—C3—C2	−24.7 (3)	C25—C20—C21—C22	179.43 (16)
C14—C13—C18—C17	−2.3 (3)	C25—C20—C21—C26	−0.1 (2)
C12—C7—C8—C9	1.5 (2)	C17—C16—C15—C14	−1.0 (3)
C12—C7—C1—C5	42.2 (3)	C29—C24—C23—C22	−177.17 (16)
C12—C7—C1—C2	−135.07 (19)	C29—C24—C23—C28	1.4 (3)
C8—C7—C12—C11	0.0 (2)	C26—C21—C22—C23	179.79 (16)
C8—C7—C1—C5	−140.94 (18)	C26—C21—C22—C27	1.0 (2)
C8—C7—C1—C2	41.8 (3)	C28—C23—C22—C21	−178.90 (16)
C3—C13—C14—C15	−178.30 (16)	C28—C23—C22—C27	−0.1 (3)

Hydrogen-bond geometry (Å, º)

Cg10 is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cg10^i	0.95	2.70	3.4521 (9)	136

Symmetry code: (i) −x, y+1, −z+1/2.