Crystal structures of 6-cyclo­propyl-1,3-diphenylfulvene and 6-(2,3-di­meth­oxy­naphth­yl)-1,3-di­phenylfulvene

The title compounds were prepared from 1,3-di­phenyl­cyclo­penta­diene, pyrrolidine, and the corresponding aldehydes in an ethano­lic solution. Each compound crystallizes with one mol­ecule per asymmetric unit and exhibits the alternating short and long bond lengths typical of fulvenes. A network of C—H...C ring inter­actions as well as C—H...O inter­actions is observed, resulting in the compact packing found in each structure.

Key indicators

Structure: 1

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.036
• wR factor = 0.094
• Data-to-parameter ratio = 17.6

Structure: 2

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.034
• wR factor = 0.082
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level G
PLAT013_ALERT_1_G N.O.K.   _shelx_hkl_checksum Found in CIF ......     Please Check
PLAT142_ALERT_4_G s.u. on b - Axis Small or Missing ..............    0.00010 Ang.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         76 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         20 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

   1 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
   0 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: 2


Alert level C
STRVA01_ALERT_4_C           Flack parameter is too small
           From the CIF: _refine_ls_abs_structure_Flack   -0.300
           From the CIF: _refine_ls_abs_structure_Flack_su    0.400

Alert level G
PLAT013_ALERT_1_G N.O.K.   _shelx_hkl_checksum Found in CIF ......     Please Check
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      0.400 Report
PLAT142_ALERT_4_G s.u. on b - Axis Small or Missing ..............    0.00010 Ang.
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         48 Note
PLAT916_ALERT_2_G Hooft y and Flack x Parameter Values Differ by .       0.11 Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         14 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 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
   1 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

For both structures, data collection: CrysAlis PRO (Rigaku OD, 2019); cell refinement: CrysAlis PRO (Rigaku OD, 2019); data reduction: CrysAlis PRO (Rigaku OD, 2019); program(s) used to solve structure: ShelXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

5-(Cyclopropylmethylidene)-1,3-diphenylcyclopenta-1,3-diene (1)

Crystal data

C21H18	Dx = 1.194 Mg m^−3
Mr = 270.35	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 50470 reflections
a = 12.9844 (2) Å	θ = 2.1–27.4°
b = 11.9583 (1) Å	µ = 0.07 mm^−1
c = 19.3729 (2) Å	T = 100 K
V = 3008.06 (6) Å^3	Block, orange
Z = 8	0.38 × 0.25 × 0.15 mm
F(000) = 1152

Data collection

XtaLAB Synergy, Single source at offset/far, HyPix3000 diffractometer	3353 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Mo) X-ray Source	2967 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.030
Detector resolution: 10.0000 pixels mm^-1	θmax = 27.4°, θmin = 2.1°
ω scans	h = −16→16
Absorption correction: empirical (using intensity measurements) (CrysAlisPro; Rigaku OD, 2019)	k = −15→15
Tmin = 0.404, Tmax = 1.000	l = −24→24
74031 measured 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)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.045P)^2 + 0.7758P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
3353 reflections	Δρmax = 0.20 e Å^−3
190 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	0.44298 (7)	0.64490 (8)	0.32819 (5)	0.0198 (2)
C2	0.50655 (7)	0.60105 (8)	0.37681 (5)	0.0203 (2)
H2	0.5051	0.6191	0.4246	0.024*
C3	0.57790 (7)	0.52136 (8)	0.34441 (5)	0.0204 (2)
C4	0.55715 (7)	0.51958 (8)	0.27550 (5)	0.0227 (2)
H4	0.5918	0.4750	0.2422	0.027*
C5	0.47342 (7)	0.59679 (8)	0.26098 (5)	0.0216 (2)
C6	0.43760 (7)	0.62688 (8)	0.19814 (5)	0.0224 (2)
H6	0.3823	0.6788	0.1965	0.027*
C7	0.35860 (7)	0.72504 (8)	0.33954 (5)	0.0207 (2)
C8	0.26145 (8)	0.70904 (9)	0.30946 (5)	0.0249 (2)
H8	0.2502	0.6466	0.2801	0.030*
C9	0.18165 (8)	0.78343 (9)	0.32221 (5)	0.0293 (2)
H9	0.1163	0.7718	0.3013	0.035*
C10	0.19672 (8)	0.87480 (9)	0.36532 (6)	0.0316 (2)
H10	0.1422	0.9260	0.3737	0.038*
C11	0.29212 (8)	0.89076 (9)	0.39608 (6)	0.0298 (2)
H11	0.3026	0.9526	0.4260	0.036*
C12	0.37234 (8)	0.81683 (8)	0.38334 (5)	0.0242 (2)
H12	0.4373	0.8287	0.4046	0.029*
C13	0.65376 (7)	0.45139 (8)	0.38061 (5)	0.0214 (2)
C14	0.65376 (7)	0.44071 (8)	0.45261 (5)	0.0240 (2)
H14	0.6078	0.4848	0.4794	0.029*
C15	0.72009 (8)	0.36649 (8)	0.48540 (5)	0.0278 (2)
H15	0.7187	0.3597	0.5343	0.033*
C16	0.78805 (9)	0.30253 (9)	0.44717 (6)	0.0311 (2)
H16	0.8319	0.2503	0.4696	0.037*
C17	0.79200 (9)	0.31494 (9)	0.37585 (6)	0.0318 (2)
H17	0.8400	0.2727	0.3495	0.038*
C18	0.72593 (8)	0.38887 (8)	0.34322 (5)	0.0269 (2)
H18	0.7296	0.3974	0.2945	0.032*
C19	0.47766 (8)	0.58544 (8)	0.13271 (5)	0.0245 (2)
H19	0.5338	0.5284	0.1360	0.029*
C20	0.48463 (8)	0.66600 (9)	0.07225 (5)	0.0268 (2)
H20A	0.4598	0.7434	0.0795	0.032*
H20B	0.5447	0.6592	0.0411	0.032*
C21	0.40700 (9)	0.57559 (9)	0.07072 (5)	0.0298 (2)
H21A	0.4188	0.5125	0.0386	0.036*
H21B	0.3339	0.5968	0.0769	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0211 (4)	0.0180 (4)	0.0203 (4)	−0.0038 (3)	0.0031 (3)	−0.0006 (3)
C2	0.0216 (4)	0.0199 (4)	0.0194 (4)	−0.0045 (4)	0.0023 (3)	−0.0010 (3)
C3	0.0212 (4)	0.0181 (4)	0.0218 (5)	−0.0036 (4)	0.0017 (4)	0.0002 (3)
C4	0.0256 (5)	0.0218 (5)	0.0208 (5)	0.0028 (4)	0.0020 (4)	−0.0006 (4)
C5	0.0236 (5)	0.0202 (4)	0.0209 (5)	−0.0002 (4)	0.0021 (4)	−0.0007 (4)
C6	0.0236 (5)	0.0213 (5)	0.0223 (5)	0.0019 (4)	0.0016 (4)	0.0001 (4)
C7	0.0232 (5)	0.0203 (4)	0.0187 (4)	−0.0013 (4)	0.0045 (4)	0.0026 (3)
C8	0.0246 (5)	0.0271 (5)	0.0230 (5)	−0.0025 (4)	0.0035 (4)	0.0011 (4)
C9	0.0225 (5)	0.0363 (6)	0.0291 (5)	0.0013 (4)	0.0040 (4)	0.0068 (4)
C10	0.0300 (5)	0.0297 (5)	0.0350 (6)	0.0086 (4)	0.0107 (4)	0.0063 (4)
C11	0.0359 (6)	0.0217 (5)	0.0318 (5)	0.0025 (4)	0.0073 (4)	−0.0014 (4)
C12	0.0267 (5)	0.0211 (5)	0.0248 (5)	−0.0016 (4)	0.0026 (4)	0.0006 (4)
C13	0.0221 (4)	0.0184 (4)	0.0237 (5)	−0.0039 (4)	−0.0019 (4)	−0.0003 (4)
C14	0.0234 (5)	0.0243 (5)	0.0244 (5)	−0.0057 (4)	−0.0002 (4)	0.0007 (4)
C15	0.0312 (5)	0.0272 (5)	0.0252 (5)	−0.0087 (4)	−0.0065 (4)	0.0046 (4)
C16	0.0321 (5)	0.0248 (5)	0.0366 (6)	−0.0004 (4)	−0.0138 (5)	0.0019 (4)
C17	0.0314 (6)	0.0292 (5)	0.0348 (6)	0.0074 (4)	−0.0080 (4)	−0.0071 (4)
C18	0.0290 (5)	0.0277 (5)	0.0240 (5)	0.0028 (4)	−0.0036 (4)	−0.0037 (4)
C19	0.0285 (5)	0.0250 (5)	0.0199 (5)	0.0059 (4)	−0.0001 (4)	−0.0002 (4)
C20	0.0300 (5)	0.0298 (5)	0.0207 (5)	0.0005 (4)	0.0025 (4)	0.0014 (4)
C21	0.0327 (5)	0.0344 (6)	0.0223 (5)	−0.0031 (4)	−0.0024 (4)	−0.0032 (4)

Geometric parameters (Å, º)

C1—C2	1.3577 (13)	C11—C12	1.3882 (14)
C1—C5	1.4774 (13)	C12—H12	0.9500
C1—C7	1.4721 (13)	C13—C14	1.4008 (14)
C2—H2	0.9500	C13—C18	1.4006 (14)
C2—C3	1.4699 (13)	C14—H14	0.9500
C3—C4	1.3621 (13)	C14—C15	1.3903 (14)
C3—C13	1.4704 (13)	C15—H15	0.9500
C4—H4	0.9500	C15—C16	1.3829 (16)
C4—C5	1.4538 (13)	C16—H16	0.9500
C5—C6	1.3520 (13)	C16—C17	1.3905 (16)
C6—H6	0.9500	C17—H17	0.9500
C6—C19	1.4570 (13)	C17—C18	1.3847 (14)
C7—C8	1.4027 (14)	C18—H18	0.9500
C7—C12	1.3988 (13)	C19—H19	1.0000
C8—H8	0.9500	C19—C20	1.5193 (14)
C8—C9	1.3879 (14)	C19—C21	1.5159 (14)
C9—H9	0.9500	C20—H20A	0.9900
C9—C10	1.3891 (16)	C20—H20B	0.9900
C10—H10	0.9500	C20—C21	1.4784 (15)
C10—C11	1.3878 (16)	C21—H21A	0.9900
C11—H11	0.9500	C21—H21B	0.9900
C2—C1—C5	107.36 (8)	C14—C13—C3	121.79 (9)
C2—C1—C7	126.89 (9)	C18—C13—C3	120.35 (9)
C7—C1—C5	125.75 (8)	C18—C13—C14	117.80 (9)
C1—C2—H2	125.1	C13—C14—H14	119.6
C1—C2—C3	109.71 (8)	C15—C14—C13	120.88 (9)
C3—C2—H2	125.1	C15—C14—H14	119.6
C2—C3—C13	125.97 (8)	C14—C15—H15	119.9
C4—C3—C2	107.70 (8)	C16—C15—C14	120.24 (10)
C4—C3—C13	126.23 (9)	C16—C15—H15	119.9
C3—C4—H4	125.4	C15—C16—H16	120.1
C3—C4—C5	109.12 (8)	C15—C16—C17	119.78 (10)
C5—C4—H4	125.4	C17—C16—H16	120.1
C4—C5—C1	106.08 (8)	C16—C17—H17	120.0
C6—C5—C1	126.72 (9)	C18—C17—C16	119.93 (10)
C6—C5—C4	126.91 (9)	C18—C17—H17	120.0
C5—C6—H6	117.6	C13—C18—H18	119.4
C5—C6—C19	124.75 (9)	C17—C18—C13	121.28 (10)
C19—C6—H6	117.6	C17—C18—H18	119.4
C8—C7—C1	121.23 (9)	C6—C19—H19	115.9
C12—C7—C1	120.44 (9)	C6—C19—C20	118.44 (9)
C12—C7—C8	118.28 (9)	C6—C19—C21	119.97 (9)
C7—C8—H8	119.7	C20—C19—H19	115.9
C9—C8—C7	120.66 (10)	C21—C19—H19	115.9
C9—C8—H8	119.7	C21—C19—C20	58.30 (7)
C8—C9—H9	119.8	C19—C20—H20A	117.7
C8—C9—C10	120.40 (10)	C19—C20—H20B	117.7
C10—C9—H9	119.8	H20A—C20—H20B	114.8
C9—C10—H10	120.3	C21—C20—C19	60.74 (7)
C11—C10—C9	119.48 (10)	C21—C20—H20A	117.7
C11—C10—H10	120.3	C21—C20—H20B	117.7
C10—C11—H11	119.8	C19—C21—H21A	117.7
C10—C11—C12	120.38 (10)	C19—C21—H21B	117.7
C12—C11—H11	119.8	C20—C21—C19	60.96 (7)
C7—C12—H12	119.6	C20—C21—H21A	117.7
C11—C12—C7	120.79 (10)	C20—C21—H21B	117.7
C11—C12—H12	119.6	H21A—C21—H21B	114.8

5-[(3,4-Dimethoxynaphthalen-2-yl)methylidene]-1,3-diphenylcyclopenta-1,3-diene (2)

Crystal data

C30H24O2	Dx = 1.267 Mg m^−3
Mr = 416.49	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 35583 reflections
a = 7.3431 (1) Å	θ = 1.9–27.3°
b = 11.5468 (1) Å	µ = 0.08 mm^−1
c = 25.7555 (3) Å	T = 100 K
V = 2183.79 (4) Å^3	Block, red
Z = 4	0.27 × 0.15 × 0.13 mm
F(000) = 880

Data collection

XtaLAB Synergy, Single source at offset/far, HyPix3000 diffractometer	4798 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Mo) X-ray Source	4437 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.036
Detector resolution: 10.0000 pixels mm^-1	θmax = 27.4°, θmin = 1.9°
ω scans	h = −9→9
Absorption correction: empirical (using intensity measurements) (CrysAlisPro; Rigaku OD, 2019)	k = −14→14
Tmin = 0.735, Tmax = 1.000	l = −32→32
54562 measured reflections

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)] = 0.034	w = 1/[σ^2(Fo^2) + (0.0415P)^2 + 0.3848P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.082	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.16 e Å^−3
4798 reflections	Δρmin = −0.18 e Å^−3
291 parameters	Absolute structure: Flack x determined using 1774 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: −0.3 (4)
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.

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

	x	y	z	Uiso*/Ueq
O1	0.44518 (18)	0.62766 (11)	0.68257 (5)	0.0247 (3)
O2	0.61050 (17)	0.49358 (11)	0.75201 (5)	0.0259 (3)
C1	−0.0406 (2)	0.65397 (15)	0.55785 (7)	0.0198 (4)
C2	−0.0799 (2)	0.59770 (15)	0.51299 (7)	0.0211 (4)
H2	−0.1346	0.6322	0.4834	0.025*
C3	−0.0254 (2)	0.47506 (15)	0.51698 (7)	0.0197 (4)
C4	0.0428 (3)	0.45757 (16)	0.56522 (6)	0.0207 (4)
H4	0.0855	0.3857	0.5784	0.025*
C5	0.0400 (2)	0.56652 (15)	0.59360 (6)	0.0196 (4)
C6	0.1117 (2)	0.58571 (15)	0.64113 (7)	0.0204 (4)
H6	0.1098	0.6635	0.6531	0.024*
C7	−0.0696 (2)	0.77839 (15)	0.56788 (7)	0.0201 (4)
C8	−0.1120 (3)	0.82200 (15)	0.61722 (7)	0.0232 (4)
H8	−0.1192	0.7705	0.6459	0.028*
C9	−0.1436 (3)	0.93976 (16)	0.62481 (8)	0.0276 (4)
H9	−0.1710	0.9678	0.6586	0.033*
C10	−0.1352 (3)	1.01607 (17)	0.58346 (8)	0.0302 (4)
H10	−0.1570	1.0963	0.5887	0.036*
C11	−0.0945 (3)	0.97418 (17)	0.53435 (8)	0.0302 (4)
H11	−0.0895	1.0260	0.5058	0.036*
C12	−0.0612 (3)	0.85764 (16)	0.52664 (7)	0.0252 (4)
H12	−0.0321	0.8307	0.4928	0.030*
C13	−0.0383 (2)	0.38948 (15)	0.47494 (6)	0.0198 (4)
C14	−0.1483 (3)	0.40870 (16)	0.43146 (7)	0.0240 (4)
H14	−0.2167	0.4783	0.4289	0.029*
C15	−0.1585 (3)	0.32715 (17)	0.39190 (7)	0.0274 (4)
H15	−0.2351	0.3408	0.3628	0.033*
C16	−0.0574 (3)	0.22612 (16)	0.39474 (7)	0.0252 (4)
H16	−0.0638	0.1707	0.3675	0.030*
C17	0.0532 (3)	0.20609 (16)	0.43754 (7)	0.0243 (4)
H17	0.1233	0.1371	0.4395	0.029*
C18	0.0617 (3)	0.28622 (16)	0.47734 (7)	0.0229 (4)
H18	0.1363	0.2711	0.5067	0.028*
C19	0.1926 (2)	0.49925 (15)	0.67648 (7)	0.0194 (4)
C20	0.3601 (2)	0.52592 (15)	0.69714 (7)	0.0206 (4)
C21	0.4485 (3)	0.45362 (15)	0.73404 (6)	0.0211 (4)
C22	0.3672 (3)	0.35129 (15)	0.74809 (7)	0.0216 (4)
H22	0.4269	0.3012	0.7719	0.026*
C23	0.1953 (3)	0.31938 (15)	0.72749 (6)	0.0198 (4)
C24	0.1143 (3)	0.21256 (16)	0.74162 (7)	0.0233 (4)
H24	0.1763	0.1620	0.7647	0.028*
C25	−0.0526 (3)	0.18134 (16)	0.72228 (7)	0.0254 (4)
H25	−0.1043	0.1087	0.7314	0.030*
C26	−0.1476 (3)	0.25666 (16)	0.68892 (7)	0.0250 (4)
H26	−0.2644	0.2353	0.6762	0.030*
C27	−0.0726 (2)	0.36052 (16)	0.67463 (6)	0.0222 (4)
H27	−0.1393	0.4111	0.6526	0.027*
C28	0.1027 (2)	0.39369 (15)	0.69210 (6)	0.0187 (4)
C29	0.5376 (3)	0.61847 (19)	0.63345 (8)	0.0317 (4)
H29A	0.4567	0.5819	0.6080	0.048*
H29B	0.6476	0.5714	0.6376	0.048*
H29C	0.5714	0.6960	0.6213	0.048*
C30	0.6930 (3)	0.42942 (18)	0.79361 (8)	0.0297 (4)
H30A	0.7212	0.3508	0.7817	0.044*
H30B	0.6085	0.4256	0.8230	0.044*
H30C	0.8055	0.4681	0.8045	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0290 (7)	0.0200 (6)	0.0252 (6)	−0.0041 (6)	−0.0044 (6)	0.0013 (5)
O2	0.0258 (6)	0.0266 (7)	0.0251 (7)	−0.0008 (6)	−0.0095 (6)	0.0015 (5)
C1	0.0178 (8)	0.0220 (9)	0.0195 (8)	−0.0005 (7)	−0.0003 (7)	0.0025 (7)
C2	0.0220 (9)	0.0227 (9)	0.0186 (8)	0.0009 (8)	−0.0026 (7)	0.0029 (7)
C3	0.0175 (8)	0.0227 (9)	0.0189 (8)	−0.0013 (7)	0.0002 (7)	0.0006 (7)
C4	0.0225 (8)	0.0208 (9)	0.0187 (8)	0.0006 (7)	−0.0008 (7)	0.0008 (7)
C5	0.0182 (8)	0.0218 (9)	0.0188 (8)	−0.0006 (7)	0.0002 (7)	0.0022 (7)
C6	0.0214 (8)	0.0184 (8)	0.0212 (8)	0.0014 (7)	−0.0005 (7)	−0.0004 (7)
C7	0.0167 (8)	0.0206 (9)	0.0229 (9)	−0.0004 (7)	−0.0033 (7)	0.0032 (7)
C8	0.0244 (9)	0.0224 (9)	0.0226 (9)	0.0014 (8)	−0.0031 (7)	0.0023 (7)
C9	0.0281 (10)	0.0264 (10)	0.0283 (10)	0.0029 (8)	−0.0048 (8)	−0.0039 (8)
C10	0.0294 (10)	0.0193 (9)	0.0420 (11)	0.0030 (8)	−0.0075 (9)	0.0002 (8)
C11	0.0322 (10)	0.0247 (10)	0.0336 (10)	−0.0016 (9)	−0.0049 (9)	0.0108 (8)
C12	0.0250 (9)	0.0269 (10)	0.0239 (9)	−0.0012 (8)	−0.0017 (8)	0.0027 (7)
C13	0.0198 (8)	0.0220 (9)	0.0174 (8)	−0.0025 (7)	0.0010 (7)	0.0013 (7)
C14	0.0258 (9)	0.0248 (9)	0.0215 (9)	0.0000 (8)	−0.0017 (7)	0.0013 (7)
C15	0.0312 (10)	0.0309 (10)	0.0201 (9)	−0.0032 (8)	−0.0048 (8)	−0.0002 (8)
C16	0.0294 (10)	0.0253 (9)	0.0211 (9)	−0.0052 (8)	0.0031 (8)	−0.0043 (7)
C17	0.0251 (9)	0.0227 (9)	0.0252 (9)	0.0000 (8)	0.0026 (8)	−0.0002 (7)
C18	0.0249 (9)	0.0250 (9)	0.0189 (9)	0.0002 (8)	−0.0010 (7)	0.0015 (7)
C19	0.0240 (9)	0.0186 (9)	0.0155 (8)	0.0026 (7)	0.0000 (7)	−0.0027 (7)
C20	0.0251 (9)	0.0187 (9)	0.0179 (8)	0.0016 (8)	0.0005 (7)	−0.0025 (7)
C21	0.0228 (9)	0.0235 (9)	0.0170 (8)	0.0039 (7)	−0.0025 (7)	−0.0038 (7)
C22	0.0257 (9)	0.0227 (9)	0.0164 (8)	0.0047 (7)	−0.0025 (7)	0.0001 (7)
C23	0.0243 (9)	0.0207 (9)	0.0145 (8)	0.0031 (7)	0.0019 (7)	−0.0016 (7)
C24	0.0295 (10)	0.0232 (9)	0.0172 (8)	0.0031 (8)	0.0007 (7)	0.0007 (7)
C25	0.0317 (10)	0.0233 (9)	0.0210 (9)	−0.0039 (8)	0.0044 (8)	0.0011 (7)
C26	0.0236 (9)	0.0295 (10)	0.0219 (9)	−0.0030 (8)	0.0000 (8)	−0.0008 (7)
C27	0.0237 (9)	0.0248 (9)	0.0182 (8)	0.0027 (8)	0.0000 (7)	0.0005 (7)
C28	0.0219 (8)	0.0195 (8)	0.0148 (8)	0.0021 (7)	0.0016 (7)	−0.0019 (6)
C29	0.0296 (10)	0.0336 (11)	0.0320 (10)	−0.0052 (9)	0.0038 (9)	0.0054 (9)
C30	0.0308 (10)	0.0321 (11)	0.0261 (10)	0.0024 (9)	−0.0096 (9)	−0.0006 (8)

Geometric parameters (Å, º)

O1—C20	1.383 (2)	C14—C15	1.389 (3)
O1—C29	1.439 (2)	C15—H15	0.9500
O2—C21	1.357 (2)	C15—C16	1.385 (3)
O2—C30	1.436 (2)	C16—H16	0.9500
C1—C2	1.357 (2)	C16—C17	1.389 (3)
C1—C5	1.489 (2)	C17—H17	0.9500
C1—C7	1.475 (2)	C17—C18	1.382 (3)
C2—H2	0.9500	C18—H18	0.9500
C2—C3	1.475 (2)	C19—C20	1.375 (2)
C3—C4	1.354 (2)	C19—C28	1.443 (2)
C3—C13	1.469 (2)	C20—C21	1.422 (2)
C4—H4	0.9500	C21—C22	1.372 (3)
C4—C5	1.455 (2)	C22—H22	0.9500
C5—C6	1.351 (2)	C22—C23	1.418 (3)
C6—H6	0.9500	C23—C24	1.417 (3)
C6—C19	1.476 (2)	C23—C28	1.425 (2)
C7—C8	1.402 (2)	C24—H24	0.9500
C7—C12	1.403 (2)	C24—C25	1.371 (3)
C8—H8	0.9500	C25—H25	0.9500
C8—C9	1.393 (3)	C25—C26	1.408 (3)
C9—H9	0.9500	C26—H26	0.9500
C9—C10	1.384 (3)	C26—C27	1.370 (3)
C10—H10	0.9500	C27—H27	0.9500
C10—C11	1.387 (3)	C27—C28	1.417 (3)
C11—H11	0.9500	C29—H29A	0.9800
C11—C12	1.382 (3)	C29—H29B	0.9800
C12—H12	0.9500	C29—H29C	0.9800
C13—C14	1.398 (2)	C30—H30A	0.9800
C13—C18	1.402 (3)	C30—H30B	0.9800
C14—H14	0.9500	C30—H30C	0.9800
C20—O1—C29	112.90 (14)	C17—C16—H16	120.1
C21—O2—C30	116.64 (15)	C16—C17—H17	119.9
C2—C1—C5	106.64 (15)	C18—C17—C16	120.23 (18)
C2—C1—C7	125.79 (16)	C18—C17—H17	119.9
C7—C1—C5	127.55 (15)	C13—C18—H18	119.6
C1—C2—H2	125.0	C17—C18—C13	120.86 (17)
C1—C2—C3	110.03 (15)	C17—C18—H18	119.6
C3—C2—H2	125.0	C20—C19—C6	116.56 (16)
C4—C3—C2	107.90 (15)	C20—C19—C28	119.35 (16)
C4—C3—C13	126.85 (17)	C28—C19—C6	124.01 (16)
C13—C3—C2	125.22 (15)	O1—C20—C21	118.28 (16)
C3—C4—H4	125.5	C19—C20—O1	119.31 (16)
C3—C4—C5	109.07 (16)	C19—C20—C21	122.39 (17)
C5—C4—H4	125.5	O2—C21—C20	115.38 (16)
C4—C5—C1	106.34 (14)	O2—C21—C22	125.74 (16)
C6—C5—C1	127.15 (16)	C22—C21—C20	118.88 (17)
C6—C5—C4	126.27 (16)	C21—C22—H22	119.6
C5—C6—H6	116.4	C21—C22—C23	120.82 (16)
C5—C6—C19	127.22 (16)	C23—C22—H22	119.6
C19—C6—H6	116.4	C22—C23—C28	120.52 (16)
C8—C7—C1	122.72 (16)	C24—C23—C22	120.26 (17)
C8—C7—C12	117.49 (16)	C24—C23—C28	119.22 (17)
C12—C7—C1	119.75 (16)	C23—C24—H24	119.6
C7—C8—H8	119.5	C25—C24—C23	120.73 (18)
C9—C8—C7	120.99 (17)	C25—C24—H24	119.6
C9—C8—H8	119.5	C24—C25—H25	119.9
C8—C9—H9	119.8	C24—C25—C26	120.15 (18)
C10—C9—C8	120.40 (18)	C26—C25—H25	119.9
C10—C9—H9	119.8	C25—C26—H26	119.8
C9—C10—H10	120.3	C27—C26—C25	120.37 (18)
C9—C10—C11	119.30 (17)	C27—C26—H26	119.8
C11—C10—H10	120.3	C26—C27—H27	119.4
C10—C11—H11	119.7	C26—C27—C28	121.11 (17)
C12—C11—C10	120.59 (18)	C28—C27—H27	119.4
C12—C11—H11	119.7	C23—C28—C19	117.96 (16)
C7—C12—H12	119.4	C27—C28—C19	123.74 (16)
C11—C12—C7	121.22 (17)	C27—C28—C23	118.30 (16)
C11—C12—H12	119.4	O1—C29—H29A	109.5
C14—C13—C3	121.39 (16)	O1—C29—H29B	109.5
C14—C13—C18	118.22 (16)	O1—C29—H29C	109.5
C18—C13—C3	120.38 (16)	H29A—C29—H29B	109.5
C13—C14—H14	119.6	H29A—C29—H29C	109.5
C15—C14—C13	120.73 (17)	H29B—C29—H29C	109.5
C15—C14—H14	119.6	O2—C30—H30A	109.5
C14—C15—H15	119.9	O2—C30—H30B	109.5
C16—C15—C14	120.21 (18)	O2—C30—H30C	109.5
C16—C15—H15	119.9	H30A—C30—H30B	109.5
C15—C16—H16	120.1	H30A—C30—H30C	109.5
C15—C16—C17	119.73 (17)	H30B—C30—H30C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···O1^i	0.95	2.50	3.429 (2)	164
C24—H24···O2^i	0.95	2.53	3.241 (2)	131

Symmetry code: (i) −x+1, y−1/2, −z+3/2.