(Tris{2-[(5-chloro-2-oxido­benzyl­idene-κO)amino-κN]eth­yl}amine-κN)­ytterbium(III): crystal structure and Hirshfeld surface analysis

Lee, S.M.; Lo, K.M.; Tan, S.L.; Tiekink, E.R.T.

doi:10.1107/S2056989016013748

(Tris{2-[(5-chloro-2-oxidobenzylidene-κO)amino-κN]ethyl}amine-κN)ytterbium(III): crystal structure and Hirshfeld surface analysis

S. M. Lee, K. M. Lo, S. L. Tan and E. R. T. Tiekink

The title compound features an amine-N-capped octahedral coordination geometry for Yb^III defined by an N₄O₃ donor set. The packing features supramolecular layers sustained by C—H

O, C—H

π(aryl) and C—Cl

π(aryl) interactions.

Keywords: crystal structure; lanthanide; coordination complex; heptadentate ligand; Hirshfeld surface analysis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989016013748/hb7612sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989016013748/hb7612Isup2.hkl Contains datablock I

CCDC reference: 1501230

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
R factor = 0.022
wR factor = 0.055
Data-to-parameter ratio = 23.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.71 Report
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.206 Report
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          3 Report

Alert level G
PLAT432_ALERT_2_G Short Inter X...Y Contact  Cl3    ..  C9      ..       3.19 Ang.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        468 Note
PLAT933_ALERT_2_G Number of OMIT records in Embedded RES .........          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density          11 Note

   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
   4 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2008); cell refinement: SMART (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

(Tris{2-[(5-chloro-2-oxidobenzylidene-κO)amino-κN]ethyl}amine-κN)ytterbium(III) top

Crystal data top

C₂₇H₂₄Cl₃N₄O₃Yb	F(000) = 1436
M_r = 731.89	D_x = 1.779 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.0452 (2) Å	Cell parameters from 9874 reflections
b = 13.1510 (2) Å	θ = 2.5–30.5°
c = 21.0926 (4) Å	µ = 3.75 mm⁻¹
β = 101.221 (1)°	T = 100 K
V = 2733.16 (9) Å³	Needle, yellow
Z = 4	0.37 × 0.06 × 0.04 mm

Data collection top

Bruker SMART APEX CCD diffractometer	7882 independent reflections
Radiation source: fine-focus sealed tube	6584 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
φ and ω scans	θ_max = 30.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→13
T_min = 0.337, T_max = 0.864	k = −18→18
29037 measured reflections	l = −30→30

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.022	H-atom parameters constrained
wR(F²) = 0.055	w = 1/[σ²(F_o²) + (0.0236P)² + 2.0547P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.004
7882 reflections	Δρ_max = 1.65 e Å⁻³
343 parameters	Δρ_min = −0.45 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Yb	0.46352 (2)	0.75973 (2)	0.57731 (2)	0.01267 (3)
Cl1	0.12533 (9)	1.28195 (5)	0.58909 (5)	0.0416 (2)
Cl2	−0.02898 (6)	0.51120 (5)	0.75694 (3)	0.02505 (14)
Cl3	0.36458 (6)	0.53255 (4)	0.23696 (3)	0.01926 (12)
O1	0.29667 (17)	0.85663 (12)	0.58719 (8)	0.0167 (3)
O2	0.33581 (17)	0.62842 (12)	0.58381 (8)	0.0164 (3)
O3	0.38891 (18)	0.76939 (12)	0.47425 (8)	0.0159 (3)
N1	0.7240 (2)	0.76956 (14)	0.63698 (10)	0.0151 (4)
N2	0.5557 (2)	0.93115 (14)	0.58045 (10)	0.0154 (4)
N3	0.4951 (2)	0.72213 (14)	0.69249 (10)	0.0148 (4)
N4	0.6072 (2)	0.64484 (14)	0.52919 (10)	0.0148 (4)
C1	0.7729 (2)	0.87631 (18)	0.64050 (12)	0.0175 (5)
H1A	0.8721	0.8773	0.6424	0.021*
H1B	0.7546	0.9087	0.6803	0.021*
C2	0.7024 (2)	0.93543 (18)	0.58208 (13)	0.0184 (5)
H2A	0.7338	1.0069	0.5851	0.022*
H2B	0.7234	0.9053	0.5422	0.022*
C3	0.4962 (3)	1.01700 (17)	0.58504 (12)	0.0171 (5)
H3	0.5514	1.0762	0.5881	0.021*
C4	0.3547 (3)	1.03227 (17)	0.58600 (11)	0.0164 (5)
C5	0.3105 (3)	1.13402 (18)	0.58747 (12)	0.0208 (5)
H5	0.3743	1.1880	0.5900	0.025*
C6	0.1758 (3)	1.15543 (19)	0.58521 (14)	0.0246 (6)
C7	0.0807 (3)	1.0776 (2)	0.58029 (14)	0.0252 (6)
H7	−0.0127	1.0932	0.5772	0.030*
C8	0.1222 (3)	0.97781 (19)	0.57992 (13)	0.0217 (5)
H8	0.0562	0.9253	0.5766	0.026*
C9	0.2601 (2)	0.95123 (17)	0.58435 (11)	0.0148 (4)
C10	0.7392 (3)	0.72872 (18)	0.70367 (12)	0.0178 (5)
H10A	0.8250	0.7538	0.7304	0.021*
H10B	0.7432	0.6535	0.7026	0.021*
C11	0.6200 (3)	0.76202 (18)	0.73361 (12)	0.0176 (5)
H11A	0.6300	0.7347	0.7780	0.021*
H11B	0.6163	0.8371	0.7357	0.021*
C12	0.4136 (2)	0.67362 (17)	0.72151 (12)	0.0162 (5)
H12	0.4367	0.6702	0.7673	0.019*
C13	0.2894 (2)	0.62359 (17)	0.69055 (12)	0.0158 (5)
C14	0.2018 (3)	0.59174 (17)	0.73117 (13)	0.0177 (5)
H14	0.2243	0.6056	0.7762	0.021*
C15	0.0842 (3)	0.54082 (18)	0.70628 (13)	0.0190 (5)
C16	0.0522 (2)	0.51588 (17)	0.64104 (13)	0.0187 (5)
H16	−0.0277	0.4782	0.6245	0.022*
C17	0.1368 (2)	0.54595 (17)	0.60038 (13)	0.0176 (5)
H17	0.1141	0.5285	0.5559	0.021*
C18	0.2572 (2)	0.60244 (16)	0.62333 (12)	0.0157 (5)
C19	0.8079 (3)	0.70835 (18)	0.60012 (12)	0.0178 (5)
H19A	0.8942	0.6891	0.6289	0.021*
H19B	0.8297	0.7496	0.5642	0.021*
C20	0.7321 (3)	0.61317 (18)	0.57314 (12)	0.0176 (5)
H20A	0.7890	0.5719	0.5495	0.021*
H20B	0.7098	0.5714	0.6087	0.021*
C21	0.5862 (2)	0.60742 (17)	0.47208 (12)	0.0164 (5)
H21	0.6498	0.5586	0.4632	0.020*
C22	0.4753 (2)	0.63213 (17)	0.41975 (11)	0.0137 (4)
C23	0.4692 (3)	0.57793 (17)	0.36155 (12)	0.0164 (5)
H23	0.5354	0.5275	0.3586	0.020*
C24	0.3680 (3)	0.59760 (17)	0.30922 (12)	0.0161 (5)
C25	0.2680 (3)	0.66999 (18)	0.31321 (12)	0.0175 (5)
H25	0.1961	0.6813	0.2774	0.021*
C26	0.2742 (2)	0.72490 (17)	0.36935 (12)	0.0159 (5)
H26	0.2058	0.7739	0.3716	0.019*
C27	0.3794 (2)	0.71038 (17)	0.42369 (12)	0.0147 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Yb	0.01552 (5)	0.00985 (5)	0.01280 (5)	0.00054 (4)	0.00315 (3)	−0.00017 (4)
Cl1	0.0456 (5)	0.0175 (3)	0.0678 (6)	0.0137 (3)	0.0262 (4)	0.0038 (3)
Cl2	0.0180 (3)	0.0273 (3)	0.0318 (4)	0.0009 (2)	0.0095 (3)	0.0094 (3)
Cl3	0.0252 (3)	0.0186 (3)	0.0143 (3)	−0.0015 (2)	0.0047 (2)	−0.0031 (2)
O1	0.0187 (9)	0.0123 (7)	0.0203 (9)	0.0016 (6)	0.0065 (7)	−0.0012 (6)
O2	0.0189 (9)	0.0128 (7)	0.0184 (9)	−0.0011 (6)	0.0058 (7)	−0.0016 (6)
O3	0.0211 (9)	0.0139 (7)	0.0124 (8)	0.0029 (6)	0.0027 (7)	0.0000 (6)
N1	0.0164 (10)	0.0133 (9)	0.0157 (10)	−0.0005 (7)	0.0031 (8)	0.0004 (7)
N2	0.0172 (10)	0.0142 (9)	0.0151 (10)	0.0007 (7)	0.0037 (8)	0.0014 (7)
N3	0.0163 (10)	0.0128 (9)	0.0146 (10)	−0.0001 (7)	0.0016 (8)	−0.0007 (7)
N4	0.0137 (9)	0.0132 (9)	0.0171 (10)	0.0015 (7)	0.0018 (8)	0.0007 (7)
C1	0.0164 (12)	0.0174 (11)	0.0182 (12)	−0.0035 (9)	0.0022 (10)	−0.0022 (9)
C2	0.0178 (12)	0.0159 (11)	0.0231 (13)	−0.0014 (9)	0.0078 (10)	0.0006 (9)
C3	0.0248 (13)	0.0125 (10)	0.0146 (12)	−0.0014 (9)	0.0052 (10)	0.0024 (8)
C4	0.0231 (12)	0.0147 (10)	0.0115 (11)	0.0031 (9)	0.0033 (9)	0.0024 (8)
C5	0.0295 (14)	0.0144 (11)	0.0202 (13)	0.0020 (10)	0.0093 (11)	0.0018 (9)
C6	0.0335 (15)	0.0140 (11)	0.0283 (15)	0.0103 (10)	0.0112 (12)	0.0022 (10)
C7	0.0219 (14)	0.0266 (13)	0.0283 (15)	0.0096 (10)	0.0077 (11)	0.0020 (11)
C8	0.0218 (13)	0.0210 (12)	0.0235 (14)	0.0016 (10)	0.0078 (11)	−0.0022 (10)
C9	0.0206 (12)	0.0146 (10)	0.0099 (11)	0.0028 (9)	0.0044 (9)	0.0001 (8)
C10	0.0170 (11)	0.0192 (11)	0.0162 (12)	0.0001 (9)	0.0008 (9)	0.0014 (9)
C11	0.0177 (11)	0.0182 (11)	0.0157 (11)	−0.0056 (9)	0.0001 (9)	0.0004 (9)
C12	0.0196 (12)	0.0135 (10)	0.0160 (12)	0.0026 (9)	0.0042 (9)	0.0000 (8)
C13	0.0169 (12)	0.0115 (10)	0.0190 (12)	0.0012 (8)	0.0038 (9)	0.0022 (8)
C14	0.0195 (12)	0.0146 (10)	0.0202 (13)	0.0024 (9)	0.0066 (10)	0.0023 (9)
C15	0.0176 (12)	0.0145 (10)	0.0270 (14)	0.0038 (9)	0.0096 (10)	0.0071 (9)
C16	0.0133 (11)	0.0133 (10)	0.0285 (14)	0.0009 (8)	0.0021 (10)	0.0015 (9)
C17	0.0172 (12)	0.0132 (10)	0.0222 (13)	0.0035 (9)	0.0030 (10)	−0.0017 (9)
C18	0.0153 (11)	0.0085 (9)	0.0236 (13)	0.0025 (8)	0.0043 (10)	0.0001 (8)
C19	0.0151 (11)	0.0197 (11)	0.0189 (12)	0.0020 (9)	0.0039 (9)	−0.0003 (9)
C20	0.0181 (12)	0.0167 (11)	0.0165 (12)	0.0047 (9)	0.0000 (9)	−0.0007 (9)
C21	0.0163 (12)	0.0136 (10)	0.0195 (12)	0.0022 (8)	0.0037 (10)	0.0006 (8)
C22	0.0138 (11)	0.0135 (10)	0.0142 (11)	−0.0007 (8)	0.0034 (9)	0.0002 (8)
C23	0.0191 (12)	0.0133 (10)	0.0173 (12)	0.0018 (9)	0.0049 (10)	−0.0012 (8)
C24	0.0231 (12)	0.0131 (10)	0.0128 (11)	−0.0029 (9)	0.0052 (9)	−0.0018 (8)
C25	0.0197 (12)	0.0168 (11)	0.0152 (12)	0.0003 (9)	0.0014 (10)	0.0019 (9)
C26	0.0167 (11)	0.0141 (10)	0.0160 (11)	0.0026 (8)	0.0008 (9)	0.0011 (8)
C27	0.0171 (11)	0.0120 (10)	0.0163 (11)	−0.0015 (8)	0.0059 (9)	0.0010 (8)

Geometric parameters (Å, º) top

Yb—O1	2.1476 (16)	C7—H7	0.9500
Yb—O2	2.1715 (16)	C8—C9	1.414 (3)
Yb—O3	2.1608 (17)	C8—H8	0.9500
Yb—N1	2.677 (2)	C10—C11	1.522 (4)
Yb—N2	2.4331 (19)	C10—H10A	0.9900
Yb—N3	2.439 (2)	C10—H10B	0.9900
Yb—N4	2.442 (2)	C11—H11A	0.9900
Cl1—C6	1.746 (2)	C11—H11B	0.9900
Cl2—C15	1.749 (3)	C12—C13	1.449 (3)
Cl3—C24	1.742 (2)	C12—H12	0.9500
O1—C9	1.295 (3)	C13—C14	1.406 (3)
O3—C27	1.307 (3)	C13—C18	1.419 (3)
O2—C18	1.300 (3)	C14—C15	1.371 (4)
N1—C1	1.484 (3)	C14—H14	0.9500
N1—C10	1.485 (3)	C15—C16	1.390 (4)
N1—C19	1.489 (3)	C16—C17	1.378 (4)
N2—C3	1.290 (3)	C16—H16	0.9500
N2—C2	1.469 (3)	C17—C18	1.421 (3)
N3—C12	1.283 (3)	C17—H17	0.9500
N3—C11	1.476 (3)	C19—C20	1.517 (3)
N4—C21	1.280 (3)	C19—H19A	0.9900
N4—C20	1.468 (3)	C19—H19B	0.9900
C1—C2	1.511 (3)	C20—H20A	0.9900
C1—H1A	0.9900	C20—H20B	0.9900
C1—H1B	0.9900	C21—C22	1.445 (3)
C2—H2A	0.9900	C21—H21	0.9500
C2—H2B	0.9900	C22—C23	1.410 (3)
C3—C4	1.440 (3)	C22—C27	1.423 (3)
C3—H3	0.9500	C23—C24	1.372 (3)
C4—C5	1.412 (3)	C23—H23	0.9500
C4—C9	1.424 (3)	C24—C25	1.398 (3)
C5—C6	1.374 (4)	C25—C26	1.378 (3)
C5—H5	0.9500	C25—H25	0.9500
C6—C7	1.390 (4)	C26—C27	1.412 (3)
C7—C8	1.377 (4)	C26—H26	0.9500

O1—Yb—N2	75.38 (6)	O1—C9—C8	120.4 (2)
O2—Yb—N3	74.91 (6)	O1—C9—C4	122.4 (2)
O3—Yb—N4	74.67 (6)	C8—C9—C4	117.2 (2)
O1—Yb—N4	160.51 (7)	N1—C10—C11	110.14 (19)
O2—Yb—N2	164.04 (7)	N1—C10—H10A	109.6
O3—Yb—N3	165.13 (7)	C11—C10—H10A	109.6
O1—Yb—O3	86.46 (6)	N1—C10—H10B	109.6
O1—Yb—O2	89.08 (6)	C11—C10—H10B	109.6
O3—Yb—O2	90.96 (6)	H10A—C10—H10B	108.1
O3—Yb—N2	91.64 (6)	N3—C11—C10	107.5 (2)
O1—Yb—N3	88.64 (7)	N3—C11—H11A	110.2
N2—Yb—N3	100.70 (7)	C10—C11—H11A	110.2
O2—Yb—N4	86.47 (6)	N3—C11—H11B	110.2
N2—Yb—N4	109.39 (7)	C10—C11—H11B	110.2
N3—Yb—N4	108.41 (7)	H11A—C11—H11B	108.5
O1—Yb—N1	129.46 (6)	N3—C12—C13	125.8 (2)
O3—Yb—N1	125.89 (6)	N3—C12—H12	117.1
O2—Yb—N1	122.97 (6)	C13—C12—H12	117.1
N2—Yb—N1	67.08 (6)	C14—C13—C18	120.2 (2)
N3—Yb—N1	67.39 (7)	C14—C13—C12	116.5 (2)
N4—Yb—N1	67.84 (6)	C18—C13—C12	123.2 (2)
C9—O1—Yb	141.74 (16)	C15—C14—C13	120.5 (2)
C27—O3—Yb	137.88 (15)	C15—C14—H14	119.8
C18—O2—Yb	133.58 (15)	C13—C14—H14	119.8
C1—N1—C10	108.82 (19)	C14—C15—C16	120.7 (2)
C1—N1—C19	108.78 (19)	C14—C15—Cl2	119.3 (2)
C10—N1—C19	109.54 (18)	C16—C15—Cl2	120.01 (19)
C1—N1—Yb	110.66 (14)	C17—C16—C15	119.8 (2)
C10—N1—Yb	109.81 (14)	C17—C16—H16	120.1
C19—N1—Yb	109.20 (14)	C15—C16—H16	120.1
C3—N2—C2	116.2 (2)	C16—C17—C18	121.7 (2)
C3—N2—Yb	129.32 (17)	C16—C17—H17	119.2
C2—N2—Yb	114.26 (14)	C18—C17—H17	119.2
C12—N3—C11	116.4 (2)	O2—C18—C13	122.7 (2)
C12—N3—Yb	127.19 (17)	O2—C18—C17	120.1 (2)
C11—N3—Yb	116.37 (15)	C13—C18—C17	117.1 (2)
C21—N4—C20	116.7 (2)	N1—C19—C20	110.4 (2)
C21—N4—Yb	128.79 (16)	N1—C19—H19A	109.6
C20—N4—Yb	114.50 (15)	C20—C19—H19A	109.6
N1—C1—C2	110.35 (19)	N1—C19—H19B	109.6
N1—C1—H1A	109.6	C20—C19—H19B	109.6
C2—C1—H1A	109.6	H19A—C19—H19B	108.1
N1—C1—H1B	109.6	N4—C20—C19	107.91 (19)
C2—C1—H1B	109.6	N4—C20—H20A	110.1
H1A—C1—H1B	108.1	C19—C20—H20A	110.1
N2—C2—C1	107.95 (19)	N4—C20—H20B	110.1
N2—C2—H2A	110.1	C19—C20—H20B	110.1
C1—C2—H2A	110.1	H20A—C20—H20B	108.4
N2—C2—H2B	110.1	N4—C21—C22	126.4 (2)
C1—C2—H2B	110.1	N4—C21—H21	116.8
H2A—C2—H2B	108.4	C22—C21—H21	116.8
N2—C3—C4	126.6 (2)	C23—C22—C27	120.1 (2)
N2—C3—H3	116.7	C23—C22—C21	116.6 (2)
C4—C3—H3	116.7	C27—C22—C21	123.2 (2)
C5—C4—C9	119.9 (2)	C24—C23—C22	120.3 (2)
C5—C4—C3	116.6 (2)	C24—C23—H23	119.8
C9—C4—C3	123.5 (2)	C22—C23—H23	119.8
C6—C5—C4	120.3 (2)	C23—C24—C25	120.6 (2)
C6—C5—H5	119.8	C23—C24—Cl3	119.79 (19)
C4—C5—H5	119.8	C25—C24—Cl3	119.66 (19)
C5—C6—C7	120.6 (2)	C26—C25—C24	119.7 (2)
C5—C6—Cl1	119.1 (2)	C26—C25—H25	120.1
C7—C6—Cl1	120.2 (2)	C24—C25—H25	120.1
C8—C7—C6	119.8 (3)	C25—C26—C27	121.9 (2)
C8—C7—H7	120.1	C25—C26—H26	119.1
C6—C7—H7	120.1	C27—C26—H26	119.1
C7—C8—C9	121.9 (2)	O3—C27—C26	120.4 (2)
C7—C8—H8	119.0	O3—C27—C22	122.3 (2)
C9—C8—H8	119.0	C26—C27—C22	117.3 (2)

C10—N1—C1—C2	−153.1 (2)	C13—C14—C15—Cl2	−174.95 (18)
C19—N1—C1—C2	87.6 (2)	C14—C15—C16—C17	−2.5 (4)
Yb—N1—C1—C2	−32.3 (2)	Cl2—C15—C16—C17	175.23 (18)
C3—N2—C2—C1	118.2 (2)	C15—C16—C17—C18	0.0 (3)
Yb—N2—C2—C1	−57.5 (2)	Yb—O2—C18—C13	−36.9 (3)
N1—C1—C2—N2	58.5 (3)	Yb—O2—C18—C17	146.44 (17)
C2—N2—C3—C4	−178.6 (2)	C14—C13—C18—O2	−178.7 (2)
Yb—N2—C3—C4	−3.6 (4)	C12—C13—C18—O2	−1.5 (3)
N2—C3—C4—C5	−176.3 (2)	C14—C13—C18—C17	−1.9 (3)
N2—C3—C4—C9	2.5 (4)	C12—C13—C18—C17	175.2 (2)
C9—C4—C5—C6	−2.1 (4)	C16—C17—C18—O2	179.0 (2)
C3—C4—C5—C6	176.8 (2)	C16—C17—C18—C13	2.2 (3)
C4—C5—C6—C7	−1.2 (4)	C1—N1—C19—C20	−158.2 (2)
C4—C5—C6—Cl1	178.5 (2)	C10—N1—C19—C20	83.0 (2)
C5—C6—C7—C8	2.3 (4)	Yb—N1—C19—C20	−37.3 (2)
Cl1—C6—C7—C8	−177.3 (2)	C21—N4—C20—C19	126.9 (2)
C6—C7—C8—C9	−0.1 (4)	Yb—N4—C20—C19	−54.7 (2)
Yb—O1—C9—C8	165.02 (19)	N1—C19—C20—N4	61.0 (3)
Yb—O1—C9—C4	−15.5 (4)	C20—N4—C21—C22	−176.0 (2)
C7—C8—C9—O1	176.5 (2)	Yb—N4—C21—C22	5.9 (4)
C7—C8—C9—C4	−3.1 (4)	N4—C21—C22—C23	−177.3 (2)
C5—C4—C9—O1	−175.4 (2)	N4—C21—C22—C27	6.0 (4)
C3—C4—C9—O1	5.8 (4)	C27—C22—C23—C24	−2.4 (3)
C5—C4—C9—C8	4.1 (3)	C21—C22—C23—C24	−179.2 (2)
C3—C4—C9—C8	−174.7 (2)	C22—C23—C24—C25	−1.4 (4)
C1—N1—C10—C11	81.9 (2)	C22—C23—C24—Cl3	178.20 (18)
C19—N1—C10—C11	−159.25 (19)	C23—C24—C25—C26	2.6 (4)
Yb—N1—C10—C11	−39.3 (2)	Cl3—C24—C25—C26	−176.95 (19)
C12—N3—C11—C10	129.8 (2)	C24—C25—C26—C27	0.0 (4)
Yb—N3—C11—C10	−51.8 (2)	Yb—O3—C27—C26	151.26 (19)
N1—C10—C11—N3	59.8 (2)	Yb—O3—C27—C22	−31.0 (4)
C11—N3—C12—C13	−176.5 (2)	C25—C26—C27—O3	174.3 (2)
Yb—N3—C12—C13	5.3 (3)	C25—C26—C27—C22	−3.6 (3)
N3—C12—C13—C14	−168.2 (2)	C23—C22—C27—O3	−173.0 (2)
N3—C12—C13—C18	14.6 (4)	C21—C22—C27—O3	3.5 (4)
C18—C13—C14—C15	−0.6 (3)	C23—C22—C27—C26	4.8 (3)
C12—C13—C14—C15	−177.9 (2)	C21—C22—C27—C26	−178.6 (2)
C13—C14—C15—C16	2.8 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3ⁱ	0.95	2.55	3.369 (3)	144
C23—H23···O2ⁱⁱ	0.95	2.60	3.413 (3)	144
C2—H2B···Cg1ⁱ	0.99	2.88	3.744 (3)	146
C24—Cl3···Cg1ⁱⁱⁱ	1.74 (1)	3.48 (1)	5.109 (3)	155 (1)

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

Percentage contribution of the different intermolecular contacts to the Hirshfeld surface of (I) top

Contact	% Contribution
H···H	35.3
C···H/H···C	25.9
Cl···H/H···Cl	23.9
Cl···C/C···Cl	5.9
O···H/H···O	5.0
Other	4.0

Geometric data (Å, °) for (I) and literature analogues top

Ln	Ln—O	Ln—N(imine)	Ln—N(amine)	Reference
Sm	2.237 (5)-2.243 (6)	2.545 (6)–2.562 (7)	2.778 (6)	Kanesato et al. (2001a)
Gd	2.216 (7)–2.235 (7)	2.529 (8)–2.542 (8)	2.737 (8)	Kanesato et al. (2001b)
Tb	2.206 (3)–2.218 (3)	2.495 (3)–2.510 (4)	2.748 (4)	Hu et al. (2015)
Er	2.175 (2)–2.1878 (19)	2.444 (2)–2.465 (2)	2.696 (2)	Pedersen et al. (2014)
Yb	2.1476 (16)–2.1715 (16)	2.4331 (19)–2.442 (2)	2.677 (2)	This work

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(Tris{2-[(5-chloro-2-oxido­benzyl­idene-κO)amino-κN]eth­yl}amine-κN)­ytterbium(III): crystal structure and Hirshfeld surface analysis

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(Tris{2-[(5-chloro-2-oxidobenzylidene-κO)amino-κN]ethyl}amine-κN)ytterbium(III): crystal structure and Hirshfeld surface analysis