X-ray structure analysis of symmetrically substituted 1,1′-diformyl­ruthenocene

The crystal and mol­ecular structure of 1,1′-formyl­ruthenocene has been determined. The mol­ecules self-assemble in a two-dimensional structure by C—H...O and C—H...π inter­actions with cisoid relative orientations of the two formyl groups.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.017 Å
• R factor = 0.053
• wR factor = 0.123
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.430
           From the CIF: _refine_ls_abs_structure_Flack_su    0.120
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.01667 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         20 Report
PLAT973_ALERT_2_C Check Calcd Positive Resid. Density on       Ru1       1.27 eA-3
PLAT973_ALERT_2_C Check Calcd Positive Resid. Density on       Ru2       1.19 eA-3
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT033_ALERT_4_G Flack x Value Deviates > 3.0 * sigma from Zero .      0.430 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          8 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 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
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2012); cell refinement: APEX2 (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS2012 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CIFTAB (Sheldrick, 2013).

1,1'-Diformylruthenocene

Crystal data

[Ru(C6H5O)2]	Dx = 1.926 Mg m^−3
Mr = 287.27	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 3163 reflections
a = 8.944 (2) Å	θ = 2.5–27.4°
b = 10.797 (3) Å	µ = 1.55 mm^−1
c = 20.520 (5) Å	T = 298 K
V = 1981.6 (8) Å^3	Needle, yellow
Z = 8	0.48 × 0.12 × 0.05 mm
F(000) = 1136

Data collection

Bruker SMART APEX CCD diffractometer	4288 independent reflections
Radiation source: fine-focus sealed tube	3556 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
Detector resolution: 8.333 pixels mm^-1	θmax = 27.1°, θmin = 2.0°
ω scans	h = −7→11
Absorption correction: multi-scan (SADABS; Bruker, 2012)	k = −13→8
Tmin = 0.499, Tmax = 0.922	l = −26→26
6151 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)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.123	w = 1/[σ^2(Fo^2) + (0.0369P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
4288 reflections	Δρmax = 1.28 e Å^−3
272 parameters	Δρmin = −0.68 e Å^−3
0 restraints	Absolute structure: Refined as an inversion twin
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.43 (12)

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
Ru1	0.80791 (9)	0.43584 (8)	0.21733 (4)	0.0277 (2)
O1	0.7067 (12)	0.7801 (9)	0.1729 (5)	0.061 (3)
O2	0.4211 (10)	0.5356 (10)	0.1480 (5)	0.065 (3)
C1	0.8625 (12)	0.6319 (9)	0.2228 (6)	0.033 (3)
C2	0.9145 (12)	0.5713 (11)	0.2804 (6)	0.037 (3)
H2	0.8837	0.5912	0.3250	0.045*
C3	1.0219 (12)	0.4849 (11)	0.2632 (6)	0.036 (3)
H3	1.0794	0.4330	0.2933	0.043*
C4	1.0382 (12)	0.4888 (11)	0.1942 (6)	0.038 (3)
H4	1.1091	0.4397	0.1685	0.045*
C5	0.9390 (12)	0.5777 (12)	0.1693 (5)	0.038 (3)
H5	0.9302	0.6028	0.1236	0.046*
C6	0.5752 (11)	0.3939 (11)	0.2021 (6)	0.034 (3)
C7	0.6230 (13)	0.3378 (11)	0.2614 (6)	0.039 (3)
H7	0.5812	0.3536	0.3047	0.047*
C8	0.7370 (15)	0.2513 (12)	0.2465 (6)	0.045 (3)
H8	0.7882	0.1966	0.2774	0.054*
C9	0.7569 (13)	0.2533 (11)	0.1764 (6)	0.038 (3)
H9	0.8262	0.2011	0.1516	0.045*
C10	0.6593 (14)	0.3402 (12)	0.1503 (6)	0.042 (3)
H10	0.6475	0.3589	0.1039	0.050*
C11	0.7431 (12)	0.7226 (10)	0.2206 (6)	0.038 (3)
H11	0.6906	0.7374	0.2589	0.046*
C12	0.4648 (13)	0.4892 (13)	0.1974 (6)	0.047 (3)
H12	0.4233	0.5177	0.2361	0.057*
Ru2	0.66487 (9)	0.45422 (8)	0.46810 (4)	0.0282 (2)
O21	0.7700 (12)	0.7744 (9)	0.3943 (5)	0.062 (3)
O22	1.0724 (10)	0.5577 (11)	0.4277 (5)	0.064 (3)
C21	0.6048 (13)	0.6452 (10)	0.4527 (6)	0.036 (3)
C22	0.5427 (12)	0.5738 (10)	0.4021 (5)	0.031 (2)
H22	0.5617	0.5840	0.3554	0.038*
C23	0.4408 (14)	0.4905 (12)	0.4307 (7)	0.046 (3)
H23	0.3775	0.4313	0.4072	0.055*
C24	0.4395 (13)	0.5115 (12)	0.4982 (7)	0.045 (3)
H24	0.3765	0.4677	0.5298	0.054*
C25	0.5434 (13)	0.6059 (11)	0.5137 (5)	0.036 (3)
H25	0.5622	0.6423	0.5567	0.043*
C26	0.9013 (12)	0.4147 (9)	0.4733 (5)	0.033 (2)
C27	0.8409 (14)	0.3525 (11)	0.4189 (6)	0.037 (3)
H27	0.8719	0.3641	0.3735	0.045*
C28	0.7321 (14)	0.2679 (12)	0.4410 (6)	0.042 (3)
H28	0.6749	0.2100	0.4140	0.051*
C29	0.7277 (14)	0.2767 (11)	0.5106 (6)	0.042 (3)
H29	0.6644	0.2264	0.5392	0.051*
C30	0.8295 (12)	0.3670 (10)	0.5314 (5)	0.035 (2)
H30	0.8524	0.3897	0.5765	0.042*
C31	0.7200 (15)	0.7386 (11)	0.4468 (7)	0.048 (3)
H31	0.7581	0.7735	0.4848	0.057*
C32	1.0095 (12)	0.5178 (11)	0.4742 (7)	0.044 (3)
H32	1.0301	0.5543	0.5142	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ru1	0.0257 (4)	0.0277 (4)	0.0298 (4)	0.0009 (4)	0.0001 (4)	−0.0011 (4)
O1	0.070 (7)	0.052 (6)	0.061 (6)	0.010 (6)	−0.008 (6)	0.012 (5)
O2	0.050 (5)	0.075 (7)	0.071 (6)	0.017 (6)	−0.012 (5)	0.023 (6)
C1	0.032 (6)	0.023 (5)	0.044 (7)	−0.005 (4)	−0.002 (5)	−0.006 (5)
C2	0.042 (6)	0.037 (6)	0.033 (6)	0.004 (5)	−0.006 (5)	−0.004 (6)
C3	0.021 (5)	0.038 (7)	0.048 (7)	0.003 (5)	−0.002 (5)	0.002 (5)
C4	0.020 (5)	0.049 (7)	0.044 (6)	−0.001 (5)	0.006 (5)	−0.001 (6)
C5	0.030 (6)	0.051 (8)	0.034 (6)	−0.013 (6)	0.004 (5)	0.000 (6)
C6	0.023 (5)	0.032 (6)	0.046 (7)	−0.003 (5)	−0.006 (5)	0.003 (5)
C7	0.033 (6)	0.035 (6)	0.050 (7)	0.001 (5)	−0.003 (5)	0.005 (6)
C8	0.054 (8)	0.032 (7)	0.049 (8)	−0.003 (6)	0.001 (6)	0.015 (6)
C9	0.046 (7)	0.021 (6)	0.046 (7)	0.003 (5)	−0.001 (6)	−0.008 (5)
C10	0.038 (7)	0.045 (7)	0.042 (7)	−0.006 (6)	−0.005 (6)	−0.012 (6)
C11	0.039 (6)	0.032 (6)	0.045 (7)	−0.002 (5)	−0.005 (6)	−0.007 (6)
C12	0.030 (6)	0.066 (9)	0.046 (7)	−0.006 (6)	0.001 (5)	0.003 (7)
Ru2	0.0265 (4)	0.0270 (4)	0.0310 (4)	−0.0004 (4)	−0.0024 (4)	−0.0014 (4)
O21	0.078 (8)	0.049 (6)	0.060 (6)	−0.014 (5)	0.018 (5)	0.010 (5)
O22	0.049 (5)	0.082 (7)	0.061 (6)	−0.015 (6)	0.008 (4)	0.028 (6)
C21	0.034 (6)	0.020 (5)	0.055 (8)	0.014 (5)	0.000 (6)	0.003 (5)
C22	0.035 (5)	0.026 (6)	0.033 (5)	0.006 (5)	−0.010 (5)	−0.003 (5)
C23	0.032 (7)	0.043 (8)	0.062 (8)	0.010 (6)	−0.017 (6)	−0.011 (6)
C24	0.025 (6)	0.045 (8)	0.065 (8)	−0.001 (5)	0.003 (6)	−0.003 (6)
C25	0.033 (6)	0.039 (7)	0.034 (6)	0.011 (5)	0.007 (5)	−0.001 (5)
C26	0.039 (6)	0.023 (5)	0.036 (6)	0.013 (5)	−0.002 (5)	−0.007 (5)
C27	0.038 (6)	0.040 (6)	0.034 (6)	0.015 (6)	0.006 (5)	−0.005 (5)
C28	0.050 (8)	0.037 (7)	0.040 (7)	0.009 (6)	−0.007 (6)	−0.012 (6)
C29	0.041 (7)	0.029 (6)	0.056 (8)	0.007 (5)	0.000 (6)	0.015 (6)
C30	0.030 (5)	0.047 (6)	0.028 (5)	−0.001 (5)	−0.004 (5)	0.005 (5)
C31	0.052 (8)	0.024 (6)	0.067 (9)	0.007 (6)	0.007 (7)	0.001 (6)
C32	0.027 (5)	0.048 (7)	0.058 (8)	0.001 (5)	−0.006 (6)	0.001 (7)

Geometric parameters (Å, º)

Ru1—C6	2.153 (10)	Ru2—C21	2.154 (10)
Ru1—C7	2.161 (12)	Ru2—C26	2.160 (11)
Ru1—C5	2.166 (11)	Ru2—C22	2.166 (10)
Ru1—C2	2.173 (11)	Ru2—C27	2.169 (11)
Ru1—C10	2.173 (11)	Ru2—C28	2.172 (12)
Ru1—C8	2.175 (12)	Ru2—C25	2.177 (11)
Ru1—C1	2.175 (10)	Ru2—C30	2.177 (11)
Ru1—C4	2.190 (11)	Ru2—C29	2.179 (11)
Ru1—C9	2.190 (12)	Ru2—C23	2.182 (12)
Ru1—C3	2.198 (11)	Ru2—C24	2.197 (12)
O1—C11	1.203 (14)	O21—C31	1.229 (15)
O2—C12	1.196 (14)	O22—C32	1.188 (14)
C1—C5	1.418 (15)	C21—C22	1.407 (15)
C1—C2	1.430 (15)	C21—C25	1.430 (16)
C1—C11	1.450 (15)	C21—C31	1.447 (17)
C2—C3	1.385 (15)	C22—C23	1.408 (17)
C2—H2	0.9800	C22—H22	0.9800
C3—C4	1.425 (15)	C23—C24	1.405 (17)
C3—H3	0.9800	C23—H23	0.9800
C4—C5	1.403 (16)	C24—C25	1.415 (17)
C4—H4	0.9800	C24—H24	0.9800
C5—H5	0.9800	C25—H25	0.9800
C6—C7	1.425 (16)	C26—C27	1.410 (15)
C6—C10	1.425 (16)	C26—C30	1.449 (15)
C6—C12	1.430 (17)	C26—C32	1.475 (16)
C7—C8	1.416 (17)	C27—C28	1.410 (17)
C7—H7	0.9800	C27—H27	0.9800
C8—C9	1.448 (16)	C28—C29	1.431 (16)
C8—H8	0.9800	C28—H28	0.9800
C9—C10	1.389 (17)	C29—C30	1.402 (16)
C9—H9	0.9800	C29—H29	0.9800
C10—H10	0.9800	C30—H30	0.9800
C11—H11	0.9300	C31—H31	0.9300
C12—H12	0.9300	C32—H32	0.9300
C6—Ru1—C7	38.6 (4)	C21—Ru2—C26	116.1 (4)
C6—Ru1—C5	127.3 (4)	C21—Ru2—C22	38.0 (4)
C7—Ru1—C5	161.9 (4)	C26—Ru2—C22	130.0 (4)
C6—Ru1—C2	130.7 (4)	C21—Ru2—C27	126.7 (5)
C7—Ru1—C2	114.6 (5)	C26—Ru2—C27	38.0 (4)
C5—Ru1—C2	63.8 (4)	C22—Ru2—C27	112.1 (4)
C6—Ru1—C10	38.5 (4)	C21—Ru2—C28	156.6 (5)
C7—Ru1—C10	64.2 (5)	C26—Ru2—C28	63.8 (4)
C5—Ru1—C10	112.3 (4)	C22—Ru2—C28	122.1 (4)
C2—Ru1—C10	164.8 (4)	C27—Ru2—C28	37.9 (5)
C6—Ru1—C8	64.2 (5)	C21—Ru2—C25	38.6 (4)
C7—Ru1—C8	38.1 (5)	C26—Ru2—C25	128.0 (4)
C5—Ru1—C8	158.5 (5)	C22—Ru2—C25	64.4 (4)
C2—Ru1—C8	125.5 (5)	C27—Ru2—C25	160.6 (4)
C10—Ru1—C8	63.9 (5)	C28—Ru2—C25	160.9 (5)
C6—Ru1—C1	115.4 (4)	C21—Ru2—C30	132.1 (4)
C7—Ru1—C1	128.8 (5)	C26—Ru2—C30	39.0 (4)
C5—Ru1—C1	38.1 (4)	C22—Ru2—C30	166.3 (4)
C2—Ru1—C1	38.4 (4)	C27—Ru2—C30	64.4 (4)
C10—Ru1—C1	129.2 (5)	C28—Ru2—C30	64.2 (4)
C8—Ru1—C1	160.6 (5)	C25—Ru2—C30	114.0 (4)
C6—Ru1—C4	158.9 (4)	C21—Ru2—C29	164.8 (5)
C7—Ru1—C4	159.8 (4)	C26—Ru2—C29	63.5 (4)
C5—Ru1—C4	37.6 (4)	C22—Ru2—C29	154.7 (4)
C2—Ru1—C4	62.7 (4)	C27—Ru2—C29	63.5 (5)
C10—Ru1—C4	124.2 (5)	C28—Ru2—C29	38.4 (4)
C8—Ru1—C4	125.0 (5)	C25—Ru2—C29	128.2 (5)
C1—Ru1—C4	63.0 (4)	C30—Ru2—C29	37.5 (4)
C6—Ru1—C9	63.5 (4)	C21—Ru2—C23	63.1 (5)
C7—Ru1—C9	63.9 (5)	C26—Ru2—C23	162.2 (5)
C5—Ru1—C9	125.1 (5)	C22—Ru2—C23	37.8 (5)
C2—Ru1—C9	157.7 (4)	C27—Ru2—C23	126.4 (5)
C10—Ru1—C9	37.1 (4)	C28—Ru2—C23	109.3 (5)
C8—Ru1—C9	38.7 (4)	C25—Ru2—C23	63.7 (5)
C1—Ru1—C9	160.4 (4)	C30—Ru2—C23	155.3 (5)
C4—Ru1—C9	110.3 (5)	C29—Ru2—C23	122.4 (5)
C6—Ru1—C3	162.7 (4)	C21—Ru2—C24	62.8 (5)
C7—Ru1—C3	127.2 (4)	C26—Ru2—C24	160.0 (5)
C5—Ru1—C3	63.5 (4)	C22—Ru2—C24	63.0 (5)
C2—Ru1—C3	36.9 (4)	C27—Ru2—C24	160.0 (5)
C10—Ru1—C3	156.7 (4)	C28—Ru2—C24	125.9 (5)
C8—Ru1—C3	110.9 (5)	C25—Ru2—C24	37.7 (4)
C1—Ru1—C3	63.1 (4)	C30—Ru2—C24	125.1 (5)
C4—Ru1—C3	37.9 (4)	C29—Ru2—C24	111.8 (5)
C9—Ru1—C3	124.2 (4)	C23—Ru2—C24	37.4 (5)
C5—C1—C2	107.1 (10)	C22—C21—C25	109.3 (10)
C5—C1—C11	127.6 (12)	C22—C21—C31	127.0 (12)
C2—C1—C11	125.0 (11)	C25—C21—C31	123.6 (12)
C5—C1—Ru1	70.6 (6)	C22—C21—Ru2	71.5 (6)
C2—C1—Ru1	70.7 (6)	C25—C21—Ru2	71.6 (6)
C11—C1—Ru1	119.3 (7)	C31—C21—Ru2	120.1 (8)
C3—C2—C1	108.8 (10)	C21—C22—C23	107.4 (10)
C3—C2—Ru1	72.5 (7)	C21—C22—Ru2	70.5 (6)
C1—C2—Ru1	70.9 (6)	C23—C22—Ru2	71.7 (7)
C3—C2—H2	125.5	C21—C22—H22	126.3
C1—C2—H2	125.5	C23—C22—H22	126.3
Ru1—C2—H2	125.5	Ru2—C22—H22	126.3
C2—C3—C4	107.7 (10)	C24—C23—C22	108.2 (11)
C2—C3—Ru1	70.6 (6)	C24—C23—Ru2	71.9 (7)
C4—C3—Ru1	70.7 (6)	C22—C23—Ru2	70.5 (7)
C2—C3—H3	126.1	C24—C23—H23	125.9
C4—C3—H3	126.1	C22—C23—H23	125.9
Ru1—C3—H3	126.1	Ru2—C23—H23	125.9
C5—C4—C3	108.5 (10)	C23—C24—C25	109.4 (12)
C5—C4—Ru1	70.3 (6)	C23—C24—Ru2	70.7 (7)
C3—C4—Ru1	71.4 (6)	C25—C24—Ru2	70.3 (6)
C5—C4—H4	125.8	C23—C24—H24	125.3
C3—C4—H4	125.8	C25—C24—H24	125.3
Ru1—C4—H4	125.8	Ru2—C24—H24	125.3
C4—C5—C1	107.8 (10)	C24—C25—C21	105.7 (11)
C4—C5—Ru1	72.1 (7)	C24—C25—Ru2	71.9 (7)
C1—C5—Ru1	71.3 (6)	C21—C25—Ru2	69.9 (6)
C4—C5—H5	126.0	C24—C25—H25	127.1
C1—C5—H5	126.0	C21—C25—H25	127.1
Ru1—C5—H5	126.0	Ru2—C25—H25	127.1
C7—C6—C10	107.8 (10)	C27—C26—C30	108.2 (10)
C7—C6—C12	124.8 (11)	C27—C26—C32	128.3 (11)
C10—C6—C12	127.4 (11)	C30—C26—C32	123.3 (10)
C7—C6—Ru1	71.0 (6)	C27—C26—Ru2	71.3 (6)
C10—C6—Ru1	71.6 (6)	C30—C26—Ru2	71.1 (6)
C12—C6—Ru1	121.8 (8)	C32—C26—Ru2	119.6 (7)
C8—C7—C6	108.2 (11)	C28—C27—C26	108.6 (11)
C8—C7—Ru1	71.5 (7)	C28—C27—Ru2	71.2 (7)
C6—C7—Ru1	70.4 (7)	C26—C27—Ru2	70.7 (6)
C8—C7—H7	125.9	C28—C27—H27	125.7
C6—C7—H7	125.9	C26—C27—H27	125.7
Ru1—C7—H7	125.9	Ru2—C27—H27	125.7
C7—C8—C9	107.0 (11)	C27—C28—C29	107.3 (11)
C7—C8—Ru1	70.4 (7)	C27—C28—Ru2	70.9 (7)
C9—C8—Ru1	71.2 (7)	C29—C28—Ru2	71.1 (7)
C7—C8—H8	126.4	C27—C28—H28	126.3
C9—C8—H8	126.4	C29—C28—H28	126.3
Ru1—C8—H8	126.4	Ru2—C28—H28	126.3
C10—C9—C8	108.4 (11)	C30—C29—C28	109.4 (11)
C10—C9—Ru1	70.8 (7)	C30—C29—Ru2	71.2 (7)
C8—C9—Ru1	70.1 (7)	C28—C29—Ru2	70.5 (7)
C10—C9—H9	125.8	C30—C29—H29	125.3
C8—C9—H9	125.8	C28—C29—H29	125.3
Ru1—C9—H9	125.8	Ru2—C29—H29	125.3
C9—C10—C6	108.6 (11)	C29—C30—C26	106.5 (10)
C9—C10—Ru1	72.1 (7)	C29—C30—Ru2	71.3 (6)
C6—C10—Ru1	70.0 (6)	C26—C30—Ru2	69.8 (6)
C9—C10—H10	125.7	C29—C30—H30	126.7
C6—C10—H10	125.7	C26—C30—H30	126.7
Ru1—C10—H10	125.7	Ru2—C30—H30	126.7
O1—C11—C1	125.0 (13)	O21—C31—C21	123.5 (13)
O1—C11—H11	117.5	O21—C31—H31	118.3
C1—C11—H11	117.5	C21—C31—H31	118.3
O2—C12—C6	125.7 (13)	O22—C32—C26	125.1 (13)
O2—C12—H12	117.1	O22—C32—H32	117.4
C6—C12—H12	117.1	C26—C32—H32	117.4
C5—C1—C2—C3	1.4 (12)	C25—C21—C22—C23	0.8 (13)
C11—C1—C2—C3	175.9 (10)	C31—C21—C22—C23	176.9 (10)
Ru1—C1—C2—C3	63.0 (8)	Ru2—C21—C22—C23	62.7 (8)
C5—C1—C2—Ru1	−61.6 (7)	C25—C21—C22—Ru2	−61.9 (8)
C11—C1—C2—Ru1	112.9 (10)	C31—C21—C22—Ru2	114.2 (11)
C1—C2—C3—C4	−0.6 (13)	C21—C22—C23—C24	0.5 (14)
Ru1—C2—C3—C4	61.3 (8)	Ru2—C22—C23—C24	62.4 (9)
C1—C2—C3—Ru1	−61.9 (8)	C21—C22—C23—Ru2	−61.9 (7)
C2—C3—C4—C5	−0.4 (14)	C22—C23—C24—C25	−1.6 (15)
Ru1—C3—C4—C5	60.8 (8)	Ru2—C23—C24—C25	59.9 (9)
C2—C3—C4—Ru1	−61.2 (8)	C22—C23—C24—Ru2	−61.5 (8)
C3—C4—C5—C1	1.3 (13)	C23—C24—C25—C21	2.0 (14)
Ru1—C4—C5—C1	62.8 (7)	Ru2—C24—C25—C21	62.1 (7)
C3—C4—C5—Ru1	−61.5 (8)	C23—C24—C25—Ru2	−60.1 (9)
C2—C1—C5—C4	−1.6 (12)	C22—C21—C25—C24	−1.7 (12)
C11—C1—C5—C4	−175.9 (10)	C31—C21—C25—C24	−178.0 (10)
Ru1—C1—C5—C4	−63.3 (8)	Ru2—C21—C25—C24	−63.5 (8)
C2—C1—C5—Ru1	61.7 (7)	C22—C21—C25—Ru2	61.8 (8)
C11—C1—C5—Ru1	−112.6 (11)	C31—C21—C25—Ru2	−114.5 (11)
C10—C6—C7—C8	0.7 (14)	C30—C26—C27—C28	0.6 (12)
C12—C6—C7—C8	−177.8 (11)	C32—C26—C27—C28	−174.8 (10)
Ru1—C6—C7—C8	−61.8 (9)	Ru2—C26—C27—C28	−61.4 (8)
C10—C6—C7—Ru1	62.5 (8)	C30—C26—C27—Ru2	61.9 (7)
C12—C6—C7—Ru1	−116.0 (11)	C32—C26—C27—Ru2	−113.4 (11)
C6—C7—C8—C9	−1.0 (14)	C26—C27—C28—C29	−1.1 (13)
Ru1—C7—C8—C9	−62.2 (9)	Ru2—C27—C28—C29	−62.2 (8)
C6—C7—C8—Ru1	61.1 (8)	C26—C27—C28—Ru2	61.1 (8)
C7—C8—C9—C10	1.0 (15)	C27—C28—C29—C30	1.3 (14)
Ru1—C8—C9—C10	−60.7 (9)	Ru2—C28—C29—C30	−60.8 (8)
C7—C8—C9—Ru1	61.7 (9)	C27—C28—C29—Ru2	62.1 (8)
C8—C9—C10—C6	−0.5 (15)	C28—C29—C30—C26	−0.9 (13)
Ru1—C9—C10—C6	−60.8 (8)	Ru2—C29—C30—C26	−61.3 (7)
C8—C9—C10—Ru1	60.2 (9)	C28—C29—C30—Ru2	60.4 (9)
C7—C6—C10—C9	−0.1 (14)	C27—C26—C30—C29	0.2 (12)
C12—C6—C10—C9	178.4 (11)	C32—C26—C30—C29	175.9 (10)
Ru1—C6—C10—C9	62.1 (9)	Ru2—C26—C30—C29	62.3 (8)
C7—C6—C10—Ru1	−62.2 (8)	C27—C26—C30—Ru2	−62.1 (8)
C12—C6—C10—Ru1	116.3 (12)	C32—C26—C30—Ru2	113.6 (9)
C5—C1—C11—O1	−12.4 (18)	C22—C21—C31—O21	6.2 (19)
C2—C1—C11—O1	174.3 (12)	C25—C21—C31—O21	−178.2 (12)
Ru1—C1—C11—O1	−99.6 (13)	Ru2—C21—C31—O21	94.9 (14)
C7—C6—C12—O2	−178.4 (13)	C27—C26—C32—O22	−6.7 (19)
C10—C6—C12—O2	3 (2)	C30—C26—C32—O22	178.6 (12)
Ru1—C6—C12—O2	93.6 (15)	Ru2—C26—C32—O22	−95.5 (13)

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the C1–C5 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O21	0.98	2.64	3.456 (16)	141
C3—H3···O1^i	0.98	2.62	3.536 (15)	156
C4—H4···O21^i	0.98	2.45	3.406 (16)	164
C9—H9···O22^i	0.98	2.42	3.370 (16)	162
C23—H23···O1^ii	0.98	2.44	3.379 (17)	161
C28—H28···O2^ii	0.98	2.43	3.392 (16)	167
C30—H30···O2^iii	0.98	2.63	3.436 (14)	140
C8—H8···Cg^i	0.98	2.78	3.546 (15)	135

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