Crystal structures of {1,1,1-tris­[(salicylaldimino)­meth­yl]ethane}­gallium as both a pyridine solvate and an aceto­nitrile 0.75-solvate and {1,1,1-tris[(salicylaldimino)­meth­yl]ethane}­indium di­chloro­methane solvate

Ventura, D.L.; Brennessel, W.W.; Durfee, W.S.

doi:10.1107/S2056989020004375

Crystal structures of {1,1,1-tris[(salicylaldimino)methyl]ethane}gallium as both a pyridine solvate and an acetonitrile 0.75-solvate and {1,1,1-tris[(salicylaldimino)methyl]ethane}indium dichloromethane solvate

D. L. Ventura, W. W. Brennessel and W. S. Durfee

The crystal structures of gallium and indium coordinated by the sexadentate ligand 1,1,1-tris[(salicylideneamino)methyl]ethane are presented as different solvates. The syntheses, melting points, infra-red (IR) spectra, high-resolution mass spectra, and ¹H and ¹³ NMR spectra are also reported.

Keywords: crystal structure; gallium; indium; sexadentate ligand; infra-red spectroscopy; IR; NMR.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989020004375/ex2030sup1.cif Contains datablocks 1a, 1b, 2, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020004375/ex20301asup2.hkl Contains datablock 1a
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020004375/ex20301bsup3.hkl Contains datablock 1b
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020004375/ex20302sup4.hkl Contains datablock 2

CCDC references: 1993782; 1993781; 1993780

checkCIF report

Key indicators

Structure: 1a

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.050
wR factor = 0.120
Data-to-parameter ratio = 36.1

Structure: 1b

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
Disorder in solvent or counterion
R factor = 0.048
wR factor = 0.119
Data-to-parameter ratio = 31.9

Structure: 2

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.029
wR factor = 0.064
Data-to-parameter ratio = 26.4

checkCIF/PLATON results

No syntax errors found



Datablock: 1a


Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15      ..O1       .       2.96 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16      ..O1       .       2.83 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H20      ..O1       .       2.78 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H22      ..O1       .       2.70 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H22      ..O2       .       2.87 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C22      ..O2               3.81 Ang.

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         23 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
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
   6 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
   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
   7 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: 1b


Alert level C
PLAT244_ALERT_4_C Low    Solvent Ueq as Compared to Neighbors of        C53 Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H34      ..O1       .       2.88 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15      ..O1       .       2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H24      ..O2       .       2.83 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H27A     ..O3       .       2.89 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6       ..O4       .       2.68 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8       ..O4       .       2.84 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8       ..O5       .       2.91 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H28A     ..N7       .       2.91 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H29B     ..N7       .       2.72 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H31C     ..N7       .       2.85 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C8       ..O5               3.81 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          6 Note
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT045_ALERT_1_G Calculated and Reported Z Differ by a Factor ...       0.25 Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          1 Report
PLAT300_ALERT_4_G Atom Site Occupancy of N8         Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C55        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C56        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H56A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H56B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H56C       Constrained at        0.5 Check
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  4  )       100% Note

Author Response: One cocrystallized acetonitrile solvent molecule is modeled as disordered over a crystallographic inversion center (50:50).

PLAT789_ALERT_4_G Atoms with Negative _atom_site_disorder_group  #          6 Check
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         12 Note

Author Response: Analogous bond lengths of the disordered solvent molecule were restrained to be similar to those of the ordered solvent molecule. Anisotropic displacement parameters were restrained toward the expected thermal motion of each atom along the solvent molecule.

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        269 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

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

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




Datablock: 2


Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6       ..O2       .       2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8       ..O2       .       2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H27B     ..O2       .       2.82 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H27B     ..O3       .       2.73 Ang.

Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600       1311 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 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
   4 ALERT level G = General information/check it is not something unexpected

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

Computing details top

Data collection: APEX2 (Bruker, 2011) for (1a), (1b); CrysAlis PRO (Rigaku OD, 2019) for (2). Cell refinement: SAINT (Bruker, 2009) for (1a), (1b); CrysAlis PRO (Rigaku OD, 2019) for (2). Data reduction: SAINT (Bruker, 2009) for (1a), (1b); CrysAlis PRO (Rigaku OD, 2019) for (2). Program(s) used to solve structure: SIR97 (Altomare et al., 1999) for (1a), (1b); ShelXT (Sheldrick, 2015a) for (2). Program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b) for (1a), (1b); SHELXL (Sheldrick, 2015b) for (2). Molecular graphics: SHELXTL (Sheldrick, 2015a) for (1a), (1b); OLEX2 (Dolomanov et al., 2009) for (2). Software used to prepare material for publication: SHELXTL (Sheldrick, 2015a) for (1a), (1b); OLEX2 (Dolomanov et al., 2009) for (2).

({[(2,2-Bis{[(2-oxidobenzylidene)amino-κ²N,O]methyl}propyl)imino]methyl}phenololato-κ²N,O)gallium(III) pyridine monosolvate (1a) top

Crystal data top

[Ga(C₂₆H₂₄N₃O₃)]·C₅H₅N	F(000) = 1192
M_r = 575.30	D_x = 1.453 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.359 (2) Å	Cell parameters from 4038 reflections
b = 20.413 (3) Å	θ = 2.5–29.3°
c = 9.7470 (15) Å	µ = 1.09 mm⁻¹
β = 98.326 (3)°	T = 100 K
V = 2629.9 (7) Å³	Block, light yellow-red
Z = 4	0.24 × 0.12 × 0.10 mm

Data collection top

Bruker SMART APEXII CCD platform diffractometer	12727 independent reflections
Radiation source: fine-focus sealed tube	7432 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.108
ω scans	θ_max = 36.3°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→22
T_min = 0.645, T_max = 0.748	k = −34→33
60216 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0454P)²] where P = (F_o² + 2F_c²)/3
12727 reflections	(Δ/σ)_max = 0.001
353 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.59 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
Ga1	0.77587 (2)	0.11922 (2)	0.10318 (2)	0.01430 (5)
O1	0.65211 (9)	0.16149 (6)	0.02567 (13)	0.0164 (3)
O2	0.76170 (10)	0.05883 (6)	−0.04912 (14)	0.0176 (3)
O3	0.86274 (9)	0.17434 (6)	0.01029 (14)	0.0165 (2)
N1	0.78187 (11)	0.17932 (7)	0.27268 (16)	0.0156 (3)
N2	0.70942 (11)	0.05079 (7)	0.21825 (16)	0.0164 (3)
N3	0.90865 (12)	0.07722 (7)	0.20645 (16)	0.0168 (3)
C1	0.84162 (14)	0.15801 (9)	0.40364 (19)	0.0179 (3)
H1A	0.817473	0.180960	0.482120	0.021*
H1B	0.913552	0.169687	0.403699	0.021*
C2	0.72347 (14)	0.06027 (10)	0.36926 (19)	0.0186 (4)
H2A	0.709864	0.018585	0.415092	0.022*
H2B	0.674714	0.093384	0.393262	0.022*
C3	0.90770 (14)	0.04766 (9)	0.3439 (2)	0.0193 (4)
H3A	0.976258	0.050283	0.398017	0.023*
H3B	0.888897	0.000841	0.332989	0.023*
C4	0.83209 (14)	0.08310 (9)	0.42247 (19)	0.0172 (3)
C5	0.85760 (15)	0.06699 (10)	0.5761 (2)	0.0220 (4)
H5A	0.925490	0.083305	0.611104	0.033*
H5B	0.855577	0.019421	0.588921	0.033*
H5C	0.808143	0.087887	0.627054	0.033*
C6	0.98866 (14)	0.07028 (9)	0.1487 (2)	0.0198 (4)
H6	1.040997	0.043083	0.193998	0.024*
C7	1.00473 (14)	0.10078 (9)	0.0203 (2)	0.0180 (4)
C8	1.08968 (14)	0.08049 (9)	−0.0384 (2)	0.0209 (4)
H8	1.130945	0.046128	0.004245	0.025*
C9	1.11419 (15)	0.10946 (10)	−0.1567 (2)	0.0237 (4)
H9	1.170891	0.094779	−0.196828	0.028*
C10	1.05410 (15)	0.16086 (10)	−0.2165 (2)	0.0219 (4)
H10	1.070829	0.181452	−0.297569	0.026*
C11	0.97104 (14)	0.18234 (9)	−0.1603 (2)	0.0192 (4)
H11	0.932365	0.217933	−0.202536	0.023*
C12	0.94230 (13)	0.15249 (9)	−0.04132 (19)	0.0158 (3)
C13	0.65794 (13)	0.00093 (9)	0.1673 (2)	0.0169 (3)
H13	0.628966	−0.026250	0.230209	0.020*
C14	0.64051 (13)	−0.01719 (9)	0.02280 (19)	0.0166 (3)
C15	0.57195 (14)	−0.06808 (9)	−0.0174 (2)	0.0191 (4)
H15	0.540261	−0.089511	0.051352	0.023*
C16	0.54908 (15)	−0.08796 (10)	−0.1531 (2)	0.0219 (4)
H16	0.502691	−0.122701	−0.178095	0.026*
C17	0.59570 (16)	−0.05586 (10)	−0.2530 (2)	0.0228 (4)
H17	0.579623	−0.068209	−0.347598	0.027*
C18	0.66476 (16)	−0.00649 (10)	−0.2167 (2)	0.0225 (4)
H18	0.695669	0.014241	−0.287057	0.027*
C19	0.69088 (14)	0.01416 (9)	−0.0783 (2)	0.0162 (3)
C20	0.73714 (13)	0.23531 (9)	0.27275 (19)	0.0165 (3)
H20	0.752561	0.261800	0.353170	0.020*
C21	0.66561 (13)	0.26093 (9)	0.16062 (19)	0.0156 (3)
C22	0.62965 (15)	0.32520 (9)	0.1758 (2)	0.0189 (4)
H22	0.659486	0.351438	0.251318	0.023*
C23	0.55173 (15)	0.35035 (10)	0.0823 (2)	0.0215 (4)
H23	0.529102	0.394032	0.091608	0.026*
C24	0.50667 (15)	0.31089 (10)	−0.0259 (2)	0.0215 (4)
H24	0.451558	0.327541	−0.088746	0.026*
C25	0.54059 (14)	0.24816 (10)	−0.0433 (2)	0.0195 (4)
H25	0.508355	0.222334	−0.117986	0.023*
C26	0.62226 (13)	0.22143 (9)	0.04754 (19)	0.0154 (3)
N4	0.27776 (15)	0.38182 (10)	0.0834 (2)	0.0345 (5)
C27	0.31372 (18)	0.33322 (12)	0.1663 (3)	0.0339 (5)
H27	0.356886	0.343928	0.249457	0.041*
C28	0.29220 (19)	0.26779 (12)	0.1390 (3)	0.0364 (5)
H28	0.320603	0.234671	0.201213	0.044*
C31	0.21756 (19)	0.36497 (12)	−0.0326 (3)	0.0350 (5)
H31	0.191992	0.398827	−0.094817	0.042*
C30	0.1903 (2)	0.30137 (13)	−0.0673 (3)	0.0411 (6)
H30	0.145712	0.291911	−0.149997	0.049*
C29	0.2291 (2)	0.25190 (13)	0.0203 (3)	0.0439 (7)
H29	0.212361	0.207478	−0.001198	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ga1	0.01435 (9)	0.01324 (9)	0.01559 (9)	0.00030 (8)	0.00307 (6)	−0.00056 (8)
O1	0.0160 (6)	0.0155 (6)	0.0177 (6)	0.0013 (5)	0.0023 (5)	−0.0019 (5)
O2	0.0178 (6)	0.0160 (6)	0.0199 (7)	−0.0024 (5)	0.0053 (5)	−0.0026 (5)
O3	0.0151 (6)	0.0151 (6)	0.0199 (6)	0.0016 (5)	0.0045 (5)	0.0002 (5)
N1	0.0162 (7)	0.0150 (7)	0.0158 (7)	−0.0006 (5)	0.0026 (6)	0.0005 (6)
N2	0.0161 (7)	0.0159 (7)	0.0171 (7)	0.0004 (6)	0.0019 (6)	0.0008 (6)
N3	0.0177 (7)	0.0143 (7)	0.0183 (8)	0.0005 (6)	0.0020 (6)	−0.0001 (6)
C1	0.0199 (8)	0.0174 (8)	0.0152 (8)	−0.0003 (7)	−0.0010 (7)	−0.0008 (7)
C2	0.0207 (9)	0.0196 (8)	0.0160 (9)	−0.0012 (7)	0.0039 (7)	0.0010 (7)
C3	0.0197 (9)	0.0191 (9)	0.0187 (9)	0.0026 (7)	0.0014 (7)	0.0027 (7)
C4	0.0197 (8)	0.0162 (8)	0.0153 (8)	0.0000 (7)	0.0008 (7)	0.0013 (7)
C5	0.0248 (10)	0.0222 (9)	0.0177 (9)	0.0000 (8)	−0.0010 (7)	0.0022 (7)
C6	0.0167 (8)	0.0176 (8)	0.0244 (10)	0.0034 (7)	0.0011 (7)	0.0008 (7)
C7	0.0175 (8)	0.0153 (8)	0.0220 (9)	0.0003 (6)	0.0056 (7)	−0.0028 (7)
C8	0.0173 (8)	0.0176 (8)	0.0285 (10)	0.0018 (7)	0.0061 (7)	−0.0032 (8)
C9	0.0191 (9)	0.0232 (10)	0.0308 (11)	−0.0009 (7)	0.0102 (8)	−0.0084 (8)
C10	0.0222 (9)	0.0231 (9)	0.0219 (10)	−0.0062 (8)	0.0076 (7)	−0.0050 (8)
C11	0.0203 (9)	0.0165 (8)	0.0210 (9)	−0.0002 (7)	0.0041 (7)	−0.0012 (7)
C12	0.0153 (8)	0.0134 (7)	0.0191 (9)	−0.0016 (6)	0.0034 (6)	−0.0039 (6)
C13	0.0146 (8)	0.0158 (8)	0.0200 (9)	0.0003 (6)	0.0022 (7)	0.0026 (7)
C14	0.0155 (8)	0.0147 (8)	0.0194 (9)	0.0006 (6)	0.0017 (7)	−0.0007 (7)
C15	0.0170 (8)	0.0182 (8)	0.0222 (9)	−0.0007 (7)	0.0030 (7)	0.0006 (7)
C16	0.0209 (9)	0.0178 (9)	0.0264 (10)	−0.0040 (7)	0.0017 (8)	−0.0046 (8)
C17	0.0277 (10)	0.0210 (9)	0.0198 (9)	−0.0038 (8)	0.0041 (8)	−0.0068 (7)
C18	0.0289 (10)	0.0196 (9)	0.0199 (9)	−0.0033 (8)	0.0071 (8)	−0.0037 (7)
C19	0.0156 (8)	0.0132 (7)	0.0201 (9)	0.0013 (6)	0.0037 (7)	−0.0009 (6)
C20	0.0176 (8)	0.0159 (8)	0.0171 (8)	−0.0019 (6)	0.0058 (7)	−0.0017 (7)
C21	0.0165 (8)	0.0142 (7)	0.0168 (8)	0.0013 (6)	0.0049 (6)	0.0003 (6)
C22	0.0224 (9)	0.0172 (8)	0.0178 (9)	0.0003 (7)	0.0055 (7)	0.0001 (7)
C23	0.0257 (10)	0.0169 (8)	0.0229 (10)	0.0052 (7)	0.0072 (8)	0.0025 (7)
C24	0.0223 (9)	0.0226 (9)	0.0198 (9)	0.0063 (7)	0.0039 (7)	0.0051 (7)
C25	0.0188 (8)	0.0221 (9)	0.0176 (9)	0.0004 (7)	0.0026 (7)	0.0011 (7)
C26	0.0147 (7)	0.0168 (8)	0.0156 (8)	0.0008 (6)	0.0052 (6)	0.0018 (6)
N4	0.0336 (10)	0.0283 (9)	0.0424 (12)	−0.0019 (9)	0.0080 (9)	−0.0097 (9)
C27	0.0279 (11)	0.0397 (13)	0.0345 (13)	−0.0025 (10)	0.0057 (10)	−0.0124 (11)
C28	0.0398 (14)	0.0325 (12)	0.0385 (14)	−0.0027 (10)	0.0113 (11)	−0.0008 (10)
C31	0.0390 (13)	0.0315 (12)	0.0352 (13)	−0.0004 (10)	0.0074 (10)	−0.0033 (10)
C30	0.0490 (15)	0.0442 (15)	0.0303 (13)	−0.0139 (13)	0.0061 (11)	−0.0122 (11)
C29	0.0610 (18)	0.0294 (13)	0.0419 (15)	−0.0146 (12)	0.0100 (13)	−0.0088 (11)

Geometric parameters (Å, º) top

Ga1—O2	1.9177 (13)	C11—C12	1.412 (3)
Ga1—O1	1.9201 (13)	C11—H11	0.9500
Ga1—O3	1.9331 (13)	C13—C14	1.442 (3)
Ga1—N1	2.0500 (16)	C13—H13	0.9500
Ga1—N2	2.0700 (16)	C14—C15	1.403 (3)
Ga1—N3	2.0923 (16)	C14—C19	1.423 (3)
O1—C26	1.314 (2)	C15—C16	1.375 (3)
O2—C19	1.315 (2)	C15—H15	0.9500
O3—C12	1.318 (2)	C16—C17	1.393 (3)
N1—C20	1.290 (2)	C16—H16	0.9500
N1—C1	1.470 (2)	C17—C18	1.378 (3)
N2—C13	1.287 (2)	C17—H17	0.9500
N2—C2	1.469 (2)	C18—C19	1.408 (3)
N3—C6	1.286 (2)	C18—H18	0.9500
N3—C3	1.471 (2)	C20—C21	1.442 (3)
C1—C4	1.547 (3)	C20—H20	0.9500
C1—H1A	0.9900	C21—C22	1.412 (3)
C1—H1B	0.9900	C21—C26	1.420 (3)
C2—C4	1.541 (3)	C22—C23	1.379 (3)
C2—H2A	0.9900	C22—H22	0.9500
C2—H2B	0.9900	C23—C24	1.393 (3)
C3—C4	1.534 (3)	C23—H23	0.9500
C3—H3A	0.9900	C24—C25	1.377 (3)
C3—H3B	0.9900	C24—H24	0.9500
C4—C5	1.523 (3)	C25—C26	1.411 (3)
C5—H5A	0.9800	C25—H25	0.9500
C5—H5B	0.9800	N4—C27	1.325 (3)
C5—H5C	0.9800	N4—C31	1.334 (3)
C6—C7	1.442 (3)	C27—C28	1.384 (3)
C6—H6	0.9500	C27—H27	0.9500
C7—C8	1.406 (3)	C28—C29	1.368 (4)
C7—C12	1.423 (3)	C28—H28	0.9500
C8—C9	1.376 (3)	C31—C30	1.377 (3)
C8—H8	0.9500	C31—H31	0.9500
C9—C10	1.396 (3)	C30—C29	1.374 (4)
C9—H9	0.9500	C30—H30	0.9500
C10—C11	1.378 (3)	C29—H29	0.9500
C10—H10	0.9500

O2—Ga1—O1	90.08 (6)	C10—C9—H9	120.6
O2—Ga1—O3	90.59 (6)	C11—C10—C9	121.38 (19)
O1—Ga1—O3	95.47 (6)	C11—C10—H10	119.3
O2—Ga1—N1	175.18 (6)	C9—C10—H10	119.3
O1—Ga1—N1	88.81 (6)	C10—C11—C12	121.29 (18)
O3—Ga1—N1	94.19 (6)	C10—C11—H11	119.4
O2—Ga1—N2	89.06 (6)	C12—C11—H11	119.4
O1—Ga1—N2	95.97 (6)	O3—C12—C11	119.86 (17)
O3—Ga1—N2	168.56 (6)	O3—C12—C7	123.07 (17)
N1—Ga1—N2	86.39 (6)	C11—C12—C7	117.03 (17)
O2—Ga1—N3	95.21 (6)	N2—C13—C14	125.55 (17)
O1—Ga1—N3	174.34 (6)	N2—C13—H13	117.2
O3—Ga1—N3	86.51 (6)	C14—C13—H13	117.2
N1—Ga1—N3	85.75 (6)	C15—C14—C19	119.62 (17)
N2—Ga1—N3	82.13 (6)	C15—C14—C13	118.01 (17)
C26—O1—Ga1	128.24 (12)	C19—C14—C13	122.37 (16)
C19—O2—Ga1	126.91 (12)	C16—C15—C14	122.20 (18)
C12—O3—Ga1	123.63 (11)	C16—C15—H15	118.9
C20—N1—C1	117.07 (16)	C14—C15—H15	118.9
C20—N1—Ga1	124.52 (13)	C15—C16—C17	118.28 (18)
C1—N1—Ga1	118.41 (12)	C15—C16—H16	120.9
C13—N2—C2	118.31 (16)	C17—C16—H16	120.9
C13—N2—Ga1	124.86 (13)	C18—C17—C16	120.99 (19)
C2—N2—Ga1	116.83 (12)	C18—C17—H17	119.5
C6—N3—C3	118.08 (16)	C16—C17—H17	119.5
C6—N3—Ga1	122.36 (13)	C17—C18—C19	121.96 (19)
C3—N3—Ga1	119.18 (12)	C17—C18—H18	119.0
N1—C1—C4	110.59 (15)	C19—C18—H18	119.0
N1—C1—H1A	109.5	O2—C19—C18	119.07 (17)
C4—C1—H1A	109.5	O2—C19—C14	124.00 (17)
N1—C1—H1B	109.5	C18—C19—C14	116.89 (17)
C4—C1—H1B	109.5	N1—C20—C21	125.27 (17)
H1A—C1—H1B	108.1	N1—C20—H20	117.4
N2—C2—C4	110.76 (15)	C21—C20—H20	117.4
N2—C2—H2A	109.5	C22—C21—C26	120.15 (17)
C4—C2—H2A	109.5	C22—C21—C20	117.11 (17)
N2—C2—H2B	109.5	C26—C21—C20	122.24 (16)
C4—C2—H2B	109.5	C23—C22—C21	120.80 (18)
H2A—C2—H2B	108.1	C23—C22—H22	119.6
N3—C3—C4	110.75 (15)	C21—C22—H22	119.6
N3—C3—H3A	109.5	C22—C23—C24	119.15 (18)
C4—C3—H3A	109.5	C22—C23—H23	120.4
N3—C3—H3B	109.5	C24—C23—H23	120.4
C4—C3—H3B	109.5	C25—C24—C23	121.16 (18)
H3A—C3—H3B	108.1	C25—C24—H24	119.4
C5—C4—C3	108.61 (15)	C23—C24—H24	119.4
C5—C4—C2	109.35 (16)	C24—C25—C26	121.36 (18)
C3—C4—C2	110.20 (15)	C24—C25—H25	119.3
C5—C4—C1	108.63 (15)	C26—C25—H25	119.3
C3—C4—C1	109.59 (15)	O1—C26—C25	118.91 (17)
C2—C4—C1	110.41 (15)	O1—C26—C21	123.76 (16)
C4—C5—H5A	109.5	C25—C26—C21	117.31 (17)
C4—C5—H5B	109.5	C27—N4—C31	116.4 (2)
H5A—C5—H5B	109.5	N4—C27—C28	124.0 (2)
C4—C5—H5C	109.5	N4—C27—H27	118.0
H5A—C5—H5C	109.5	C28—C27—H27	118.0
H5B—C5—H5C	109.5	C29—C28—C27	118.5 (3)
N3—C6—C7	124.76 (17)	C29—C28—H28	120.8
N3—C6—H6	117.6	C27—C28—H28	120.8
C7—C6—H6	117.6	N4—C31—C30	123.8 (3)
C8—C7—C12	120.33 (18)	N4—C31—H31	118.1
C8—C7—C6	117.20 (17)	C30—C31—H31	118.1
C12—C7—C6	122.34 (17)	C29—C30—C31	118.5 (2)
C9—C8—C7	121.23 (19)	C29—C30—H30	120.7
C9—C8—H8	119.4	C31—C30—H30	120.7
C7—C8—H8	119.4	C28—C29—C30	118.8 (2)
C8—C9—C10	118.71 (18)	C28—C29—H29	120.6
C8—C9—H9	120.6	C30—C29—H29	120.6

C20—N1—C1—C4	143.42 (16)	C19—C14—C15—C16	−1.8 (3)
Ga1—N1—C1—C4	−37.03 (19)	C13—C14—C15—C16	178.80 (18)
C13—N2—C2—C4	139.46 (17)	C14—C15—C16—C17	−0.3 (3)
Ga1—N2—C2—C4	−40.07 (19)	C15—C16—C17—C18	1.5 (3)
C6—N3—C3—C4	155.81 (17)	C16—C17—C18—C19	−0.5 (3)
Ga1—N3—C3—C4	−31.1 (2)	Ga1—O2—C19—C18	153.46 (14)
N3—C3—C4—C5	−161.58 (15)	Ga1—O2—C19—C14	−29.1 (2)
N3—C3—C4—C2	78.64 (19)	C17—C18—C19—O2	175.99 (18)
N3—C3—C4—C1	−43.0 (2)	C17—C18—C19—C14	−1.6 (3)
N2—C2—C4—C5	−157.84 (15)	C15—C14—C19—O2	−174.77 (17)
N2—C2—C4—C3	−38.5 (2)	C13—C14—C19—O2	4.6 (3)
N2—C2—C4—C1	82.69 (19)	C15—C14—C19—C18	2.7 (3)
N1—C1—C4—C5	−157.85 (15)	C13—C14—C19—C18	−177.91 (17)
N1—C1—C4—C3	83.63 (18)	C1—N1—C20—C21	−171.93 (17)
N1—C1—C4—C2	−37.9 (2)	Ga1—N1—C20—C21	8.6 (3)
C3—N3—C6—C7	−174.51 (18)	N1—C20—C21—C22	−175.78 (17)
Ga1—N3—C6—C7	12.6 (3)	N1—C20—C21—C26	12.3 (3)
N3—C6—C7—C8	−170.91 (19)	C26—C21—C22—C23	0.5 (3)
N3—C6—C7—C12	13.3 (3)	C20—C21—C22—C23	−171.58 (17)
C12—C7—C8—C9	−0.5 (3)	C21—C22—C23—C24	1.7 (3)
C6—C7—C8—C9	−176.32 (19)	C22—C23—C24—C25	−2.0 (3)
C7—C8—C9—C10	1.4 (3)	C23—C24—C25—C26	−0.1 (3)
C8—C9—C10—C11	−0.6 (3)	Ga1—O1—C26—C25	165.16 (13)
C9—C10—C11—C12	−1.1 (3)	Ga1—O1—C26—C21	−16.8 (2)
Ga1—O3—C12—C11	148.16 (14)	C24—C25—C26—O1	−179.51 (17)
Ga1—O3—C12—C7	−34.2 (2)	C24—C25—C26—C21	2.3 (3)
C10—C11—C12—O3	179.70 (17)	C22—C21—C26—O1	179.38 (16)
C10—C11—C12—C7	2.0 (3)	C20—C21—C26—O1	−8.9 (3)
C8—C7—C12—O3	−178.84 (17)	C22—C21—C26—C25	−2.5 (3)
C6—C7—C12—O3	−3.2 (3)	C20—C21—C26—C25	169.20 (17)
C8—C7—C12—C11	−1.2 (3)	C31—N4—C27—C28	−0.1 (4)
C6—C7—C12—C11	174.44 (17)	N4—C27—C28—C29	−0.8 (4)
C2—N2—C13—C14	−177.24 (17)	C27—N4—C31—C30	1.4 (4)
Ga1—N2—C13—C14	2.2 (3)	N4—C31—C30—C29	−1.7 (4)
N2—C13—C14—C15	−171.93 (17)	C27—C28—C29—C30	0.5 (4)
N2—C13—C14—C19	8.7 (3)	C31—C30—C29—C28	0.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1ⁱ	0.95	2.96	3.540 (2)	121
C16—H16···O1ⁱ	0.95	2.83	3.462 (2)	125
C20—H20···O1ⁱⁱ	0.95	2.78	3.552 (2)	139
C22—H22···O1ⁱⁱ	0.95	2.70	3.391 (2)	130
C20—H20···O3ⁱⁱ	0.95	2.36	3.233 (2)	153
C8—H8···O2ⁱⁱⁱ	0.95	2.58	3.502 (2)	164
C22—H22···O2ⁱⁱ	0.95	2.87	3.812 (2)	172

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

({[(2,2-Bis{[(2-oxidobenzylidene)amino-κ²N,O]methyl}propyl)imino]methyl}phenololato-κ²N,O)gallium(III) acetonitrile 0.75-solvate (1b) top

Crystal data top

[Ga(C₂₆H₂₄N₃O₃)]·0.75C₂H₃N	Z = 4
M_r = 526.99	F(000) = 1090
Triclinic, P1	D_x = 1.459 Mg m⁻³
a = 10.9053 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.1157 (8) Å	Cell parameters from 3787 reflections
c = 16.2324 (9) Å	θ = 2.3–31.6°
α = 93.915 (1)°	µ = 1.18 mm⁻¹
β = 103.120 (1)°	T = 173 K
γ = 97.600 (1)°	Block, colorless
V = 2399.6 (2) Å³	0.24 × 0.24 × 0.20 mm

Data collection top

Bruker SMART APEXII CCD platform diffractometer	20841 independent reflections
Radiation source: fine-focus sealed tube	12632 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
ω scans	θ_max = 35.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→17
T_min = 0.666, T_max = 0.748	k = −22→22
52020 measured reflections	l = −26→26

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0459P)²] where P = (F_o² + 2F_c²)/3
20841 reflections	(Δ/σ)_max = 0.001
653 parameters	Δρ_max = 0.62 e Å⁻³
12 restraints	Δρ_min = −0.55 e Å⁻³

Special details top

Refinement. One cocrystallized acetonitrile solvent molecule is modeled as disordered over a crystallographic inversion center (50:50). Analogous bond lengths of the disordered solvent molecule were restrained to be similar to those of the ordered solvent molecule. Anisotropic displacement parameters were restrained toward the expected thermal motion of each atom along the solvent molecule.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ga1	0.33445 (2)	0.03781 (2)	0.24211 (2)	0.01860 (5)
O1	0.44828 (12)	0.13910 (10)	0.31777 (8)	0.0220 (3)
O2	0.46507 (12)	−0.04363 (10)	0.25420 (8)	0.0218 (3)
O3	0.37262 (13)	0.08983 (10)	0.14315 (8)	0.0241 (3)
N1	0.18433 (15)	0.11232 (12)	0.24496 (10)	0.0212 (3)
N2	0.27584 (14)	−0.02693 (12)	0.34216 (10)	0.0209 (3)
N3	0.19786 (15)	−0.06598 (12)	0.16370 (10)	0.0217 (3)
C1	0.05468 (18)	0.05719 (15)	0.21985 (13)	0.0255 (4)
H1A	0.026618	0.046121	0.157090	0.031*
H1B	−0.005405	0.093924	0.240757	0.031*
C2	0.14316 (17)	−0.02575 (15)	0.34819 (12)	0.0246 (4)
H2A	0.135976	0.036435	0.377438	0.030*
H2B	0.117628	−0.077622	0.381760	0.030*
C3	0.09945 (18)	−0.11402 (15)	0.20160 (12)	0.0245 (4)
H3A	0.134205	−0.163818	0.236144	0.029*
H3B	0.026198	−0.145981	0.155998	0.029*
C4	0.05462 (18)	−0.04032 (15)	0.25812 (12)	0.0238 (4)
C5	−0.08040 (19)	−0.08028 (17)	0.26360 (15)	0.0329 (5)
H5A	−0.082878	−0.146596	0.278286	0.049*
H5B	−0.139827	−0.079009	0.208585	0.049*
H5C	−0.104986	−0.040845	0.307452	0.049*
C6	0.19550 (19)	0.20191 (15)	0.27144 (12)	0.0237 (4)
H6	0.119766	0.230078	0.263599	0.028*
C7	0.31410 (19)	0.26305 (14)	0.31215 (12)	0.0232 (4)
C8	0.3057 (2)	0.35909 (16)	0.33702 (15)	0.0331 (5)
H8	0.226524	0.381942	0.320075	0.040*
C9	0.4093 (2)	0.42044 (17)	0.38521 (16)	0.0387 (5)
H9	0.402551	0.485296	0.400841	0.046*
C10	0.5245 (2)	0.38591 (16)	0.41078 (14)	0.0336 (5)
H10	0.596392	0.427516	0.444869	0.040*
C11	0.5359 (2)	0.29228 (15)	0.38738 (12)	0.0266 (4)
H11	0.615473	0.270528	0.405827	0.032*
C12	0.43154 (18)	0.22808 (14)	0.33655 (11)	0.0219 (4)
C13	0.34944 (18)	−0.06416 (14)	0.40040 (11)	0.0218 (4)
H13	0.320358	−0.077190	0.449969	0.026*
C14	0.47214 (18)	−0.08761 (14)	0.39642 (12)	0.0219 (4)
C15	0.53730 (19)	−0.13112 (16)	0.46534 (13)	0.0277 (4)
H15	0.506073	−0.132892	0.515377	0.033*
C16	0.6443 (2)	−0.17097 (18)	0.46246 (14)	0.0339 (5)
H16	0.687720	−0.199144	0.509935	0.041*
C17	0.6879 (2)	−0.16919 (17)	0.38805 (14)	0.0329 (5)
H17	0.760288	−0.198519	0.384291	0.039*
C18	0.62782 (18)	−0.12554 (15)	0.31982 (13)	0.0260 (4)
H18	0.660432	−0.124775	0.270303	0.031*
C19	0.51916 (17)	−0.08206 (13)	0.32185 (12)	0.0204 (4)
C20	0.18695 (18)	−0.08578 (14)	0.08384 (12)	0.0228 (4)
H20	0.122273	−0.136873	0.055435	0.027*
C21	0.26351 (18)	−0.03783 (14)	0.03338 (11)	0.0220 (4)
C22	0.2445 (2)	−0.07568 (15)	−0.05216 (12)	0.0272 (4)
H22	0.187717	−0.133888	−0.072312	0.033*
C23	0.3057 (2)	−0.03073 (16)	−0.10647 (13)	0.0296 (4)
H23	0.293134	−0.057784	−0.163514	0.036*
C24	0.3869 (2)	0.05560 (16)	−0.07693 (13)	0.0290 (4)
H24	0.429615	0.087588	−0.114433	0.035*
C25	0.4062 (2)	0.09529 (15)	0.00563 (12)	0.0271 (4)
H25	0.459923	0.155256	0.023510	0.033*
C26	0.34797 (18)	0.04897 (14)	0.06428 (11)	0.0208 (4)
Ga2	0.88779 (2)	0.37876 (2)	0.20703 (2)	0.02138 (5)
O4	0.96341 (13)	0.33951 (10)	0.31629 (8)	0.0252 (3)
O5	1.03345 (14)	0.47499 (10)	0.21460 (9)	0.0274 (3)
O6	0.95907 (14)	0.28754 (10)	0.14551 (8)	0.0253 (3)
N4	0.72159 (16)	0.29010 (12)	0.20611 (10)	0.0234 (3)
N5	0.79794 (16)	0.48650 (12)	0.25177 (10)	0.0257 (3)
N6	0.79023 (16)	0.41376 (12)	0.08876 (10)	0.0258 (4)
C27	0.60495 (19)	0.30705 (15)	0.14703 (14)	0.0301 (5)
H27A	0.529706	0.275237	0.164450	0.036*
H27B	0.602541	0.278657	0.089103	0.036*
C28	0.6574 (2)	0.46920 (16)	0.23465 (14)	0.0304 (4)
H28A	0.625324	0.531380	0.238360	0.037*
H28B	0.630943	0.430783	0.278180	0.037*
C29	0.6718 (2)	0.45548 (16)	0.08224 (13)	0.0314 (5)
H29A	0.617476	0.439976	0.023830	0.038*
H29B	0.692541	0.526262	0.093844	0.038*
C30	0.5993 (2)	0.41555 (16)	0.14597 (13)	0.0298 (4)
C31	0.4592 (2)	0.4286 (2)	0.11911 (17)	0.0435 (6)
H31A	0.415714	0.408886	0.163195	0.065*
H31B	0.418523	0.389050	0.065437	0.065*
H31C	0.453512	0.496329	0.111512	0.065*
C32	0.70962 (18)	0.22489 (14)	0.25667 (12)	0.0224 (4)
H32	0.627549	0.188283	0.249186	0.027*
C33	0.80972 (18)	0.20277 (14)	0.32341 (12)	0.0213 (4)
C34	0.7804 (2)	0.12148 (15)	0.36508 (13)	0.0261 (4)
H34	0.698088	0.084187	0.347472	0.031*
C35	0.8688 (2)	0.09528 (15)	0.43072 (13)	0.0292 (4)
H35	0.848965	0.039562	0.457714	0.035*
C36	0.9883 (2)	0.15185 (16)	0.45706 (13)	0.0296 (4)
H36	1.050090	0.134068	0.502320	0.036*
C37	1.0184 (2)	0.23275 (15)	0.41893 (12)	0.0266 (4)
H37	1.099980	0.270522	0.439196	0.032*
C38	0.93063 (18)	0.26111 (14)	0.35021 (12)	0.0219 (4)
C39	0.8561 (2)	0.56736 (16)	0.29109 (13)	0.0302 (4)
H39	0.805555	0.611047	0.308692	0.036*
C40	0.9918 (2)	0.59753 (15)	0.31083 (13)	0.0298 (5)
C41	1.0425 (3)	0.67730 (16)	0.37092 (15)	0.0387 (5)
H41	0.986699	0.709721	0.395752	0.046*
C42	1.1712 (3)	0.70961 (18)	0.39470 (17)	0.0466 (7)
H42	1.204642	0.761936	0.437371	0.056*
C43	1.2517 (3)	0.66453 (17)	0.35532 (17)	0.0455 (7)
H43	1.340637	0.687230	0.370669	0.055*
C44	1.2049 (2)	0.58765 (16)	0.29454 (15)	0.0370 (5)
H44	1.261587	0.559550	0.267123	0.044*
C45	1.0733 (2)	0.54965 (14)	0.27215 (13)	0.0273 (4)
C46	0.8377 (2)	0.40946 (15)	0.02332 (12)	0.0290 (4)
H46	0.798146	0.438958	−0.024532	0.035*
C47	0.9459 (2)	0.36367 (15)	0.01634 (13)	0.0284 (4)
C48	0.9925 (2)	0.37474 (16)	−0.05753 (13)	0.0341 (5)
H48	0.954108	0.413589	−0.098494	0.041*
C49	1.0913 (2)	0.33087 (17)	−0.07124 (14)	0.0376 (6)
H49	1.122712	0.340226	−0.120547	0.045*
C50	1.1456 (2)	0.27204 (17)	−0.01189 (14)	0.0368 (5)
H50	1.214005	0.240870	−0.021336	0.044*
C51	1.1014 (2)	0.25852 (17)	0.06031 (13)	0.0318 (5)
H51	1.139212	0.217512	0.099417	0.038*
C52	1.00143 (19)	0.30438 (14)	0.07704 (12)	0.0254 (4)
N7	0.5915 (4)	0.6858 (2)	0.1290 (2)	0.0948 (12)
C53	0.5005 (4)	0.71106 (19)	0.13652 (19)	0.0567 (8)
C54	0.3847 (3)	0.7435 (2)	0.1459 (2)	0.0725 (10)
H54A	0.326486	0.740988	0.089818	0.109*
H54B	0.403900	0.809746	0.172898	0.109*
H54C	0.344580	0.701975	0.181432	0.109*
N8	0.1723 (7)	0.4753 (6)	0.5239 (4)	0.108 (3)	0.5
C55	0.0695 (12)	0.4891 (11)	0.5101 (7)	0.068 (3)	0.5
C56	−0.0654 (12)	0.4986 (14)	0.4977 (10)	0.092 (4)	0.5
H56A	−0.080115	0.559478	0.474522	0.137*	0.5
H56B	−0.089116	0.497416	0.552425	0.137*	0.5
H56C	−0.117265	0.445106	0.457992	0.137*	0.5

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ga1	0.01759 (10)	0.02105 (11)	0.01673 (9)	0.00134 (8)	0.00448 (7)	0.00080 (7)
O1	0.0196 (6)	0.0242 (7)	0.0205 (6)	0.0034 (5)	0.0025 (5)	−0.0019 (5)
O2	0.0220 (6)	0.0265 (7)	0.0182 (6)	0.0061 (5)	0.0062 (5)	0.0024 (5)
O3	0.0292 (7)	0.0235 (7)	0.0176 (6)	−0.0033 (6)	0.0064 (5)	−0.0012 (5)
N1	0.0190 (7)	0.0245 (8)	0.0196 (7)	0.0031 (6)	0.0031 (6)	0.0032 (6)
N2	0.0185 (7)	0.0250 (8)	0.0203 (7)	0.0032 (6)	0.0071 (6)	0.0008 (6)
N3	0.0214 (8)	0.0226 (8)	0.0209 (7)	0.0011 (6)	0.0061 (6)	0.0008 (6)
C1	0.0182 (9)	0.0300 (11)	0.0267 (10)	0.0034 (8)	0.0024 (7)	0.0024 (8)
C2	0.0193 (9)	0.0319 (11)	0.0244 (9)	0.0044 (8)	0.0086 (7)	0.0033 (8)
C3	0.0221 (9)	0.0255 (10)	0.0250 (9)	−0.0026 (7)	0.0075 (7)	0.0020 (8)
C4	0.0182 (8)	0.0285 (10)	0.0250 (9)	0.0022 (7)	0.0064 (7)	0.0022 (8)
C5	0.0209 (9)	0.0396 (13)	0.0391 (12)	0.0005 (9)	0.0112 (9)	0.0043 (10)
C6	0.0243 (9)	0.0269 (10)	0.0219 (9)	0.0073 (8)	0.0065 (7)	0.0052 (7)
C7	0.0257 (9)	0.0226 (10)	0.0227 (9)	0.0045 (7)	0.0080 (7)	0.0028 (7)
C8	0.0350 (12)	0.0249 (11)	0.0407 (12)	0.0078 (9)	0.0098 (10)	0.0027 (9)
C9	0.0454 (14)	0.0228 (11)	0.0465 (14)	0.0013 (10)	0.0127 (11)	−0.0057 (10)
C10	0.0362 (12)	0.0288 (11)	0.0326 (11)	−0.0050 (9)	0.0103 (9)	−0.0065 (9)
C11	0.0256 (10)	0.0309 (11)	0.0219 (9)	0.0005 (8)	0.0070 (8)	−0.0029 (8)
C12	0.0245 (9)	0.0259 (10)	0.0163 (8)	0.0017 (7)	0.0082 (7)	0.0021 (7)
C13	0.0241 (9)	0.0233 (9)	0.0177 (8)	0.0004 (7)	0.0066 (7)	0.0009 (7)
C14	0.0207 (9)	0.0237 (10)	0.0197 (8)	0.0001 (7)	0.0040 (7)	0.0004 (7)
C15	0.0259 (10)	0.0340 (12)	0.0222 (9)	0.0043 (9)	0.0034 (8)	0.0039 (8)
C16	0.0268 (10)	0.0434 (13)	0.0320 (11)	0.0124 (10)	0.0014 (9)	0.0119 (10)
C17	0.0223 (10)	0.0388 (13)	0.0381 (12)	0.0098 (9)	0.0048 (9)	0.0055 (10)
C18	0.0196 (9)	0.0305 (11)	0.0271 (10)	0.0020 (8)	0.0055 (8)	0.0000 (8)
C19	0.0182 (8)	0.0193 (9)	0.0220 (9)	0.0001 (7)	0.0032 (7)	−0.0003 (7)
C20	0.0220 (9)	0.0193 (9)	0.0248 (9)	−0.0006 (7)	0.0040 (7)	−0.0011 (7)
C21	0.0226 (9)	0.0236 (10)	0.0182 (8)	0.0030 (7)	0.0028 (7)	0.0000 (7)
C22	0.0302 (10)	0.0260 (10)	0.0216 (9)	−0.0009 (8)	0.0035 (8)	−0.0050 (8)
C23	0.0355 (11)	0.0342 (12)	0.0181 (9)	0.0033 (9)	0.0068 (8)	−0.0019 (8)
C24	0.0360 (11)	0.0303 (11)	0.0230 (9)	0.0027 (9)	0.0125 (8)	0.0054 (8)
C25	0.0299 (10)	0.0269 (10)	0.0227 (9)	−0.0019 (8)	0.0067 (8)	0.0011 (8)
C26	0.0229 (9)	0.0222 (9)	0.0169 (8)	0.0042 (7)	0.0040 (7)	0.0005 (7)
Ga2	0.02359 (11)	0.02028 (11)	0.01746 (10)	−0.00167 (8)	0.00174 (8)	0.00285 (8)
O4	0.0273 (7)	0.0247 (7)	0.0197 (6)	−0.0027 (6)	0.0010 (5)	0.0043 (5)
O5	0.0307 (7)	0.0243 (7)	0.0240 (7)	−0.0059 (6)	0.0065 (6)	0.0007 (6)
O6	0.0330 (8)	0.0219 (7)	0.0208 (7)	0.0010 (6)	0.0070 (6)	0.0041 (5)
N4	0.0243 (8)	0.0221 (8)	0.0205 (7)	−0.0007 (6)	0.0005 (6)	0.0039 (6)
N5	0.0269 (8)	0.0253 (9)	0.0225 (8)	0.0005 (7)	0.0025 (7)	0.0041 (7)
N6	0.0309 (9)	0.0219 (8)	0.0203 (8)	−0.0020 (7)	0.0002 (7)	0.0043 (6)
C27	0.0245 (10)	0.0294 (11)	0.0304 (10)	−0.0034 (8)	−0.0029 (8)	0.0078 (9)
C28	0.0272 (10)	0.0314 (11)	0.0333 (11)	0.0072 (9)	0.0058 (9)	0.0068 (9)
C29	0.0354 (11)	0.0289 (11)	0.0256 (10)	0.0034 (9)	−0.0020 (9)	0.0082 (8)
C30	0.0277 (10)	0.0297 (11)	0.0287 (10)	0.0020 (8)	−0.0002 (8)	0.0074 (8)
C31	0.0287 (12)	0.0487 (16)	0.0496 (15)	0.0070 (11)	−0.0021 (11)	0.0179 (12)
C32	0.0217 (9)	0.0208 (9)	0.0243 (9)	0.0010 (7)	0.0065 (7)	0.0007 (7)
C33	0.0240 (9)	0.0217 (9)	0.0204 (8)	0.0048 (7)	0.0085 (7)	0.0039 (7)
C34	0.0299 (10)	0.0233 (10)	0.0282 (10)	0.0048 (8)	0.0117 (8)	0.0056 (8)
C35	0.0429 (12)	0.0231 (10)	0.0262 (10)	0.0100 (9)	0.0130 (9)	0.0087 (8)
C36	0.0377 (12)	0.0313 (11)	0.0217 (9)	0.0137 (9)	0.0053 (8)	0.0051 (8)
C37	0.0276 (10)	0.0310 (11)	0.0206 (9)	0.0058 (8)	0.0039 (8)	0.0017 (8)
C38	0.0249 (9)	0.0236 (10)	0.0188 (8)	0.0053 (8)	0.0075 (7)	0.0028 (7)
C39	0.0377 (12)	0.0262 (11)	0.0253 (10)	0.0050 (9)	0.0049 (9)	0.0014 (8)
C40	0.0383 (12)	0.0210 (10)	0.0246 (10)	−0.0021 (9)	0.0002 (9)	0.0025 (8)
C41	0.0516 (15)	0.0249 (11)	0.0337 (12)	0.0029 (10)	0.0020 (11)	−0.0040 (9)
C42	0.0551 (16)	0.0261 (12)	0.0451 (14)	−0.0064 (11)	−0.0065 (12)	−0.0036 (11)
C43	0.0412 (14)	0.0308 (13)	0.0498 (15)	−0.0109 (11)	−0.0094 (12)	0.0030 (11)
C44	0.0336 (12)	0.0290 (12)	0.0423 (13)	−0.0062 (9)	0.0021 (10)	0.0055 (10)
C45	0.0339 (11)	0.0192 (9)	0.0238 (9)	−0.0036 (8)	0.0002 (8)	0.0055 (7)
C46	0.0391 (12)	0.0243 (10)	0.0189 (9)	−0.0030 (9)	0.0008 (8)	0.0051 (7)
C47	0.0372 (11)	0.0229 (10)	0.0217 (9)	−0.0053 (8)	0.0061 (8)	0.0016 (7)
C48	0.0473 (13)	0.0290 (11)	0.0219 (10)	−0.0088 (10)	0.0083 (9)	0.0032 (8)
C49	0.0495 (14)	0.0363 (13)	0.0243 (10)	−0.0124 (11)	0.0156 (10)	−0.0017 (9)
C50	0.0356 (12)	0.0390 (13)	0.0325 (12)	−0.0082 (10)	0.0120 (10)	−0.0054 (10)
C51	0.0319 (11)	0.0347 (12)	0.0261 (10)	−0.0011 (9)	0.0058 (9)	−0.0001 (9)
C52	0.0298 (10)	0.0220 (10)	0.0190 (9)	−0.0084 (8)	0.0031 (7)	−0.0032 (7)
N7	0.123 (3)	0.0493 (18)	0.141 (3)	0.0348 (19)	0.077 (3)	0.0124 (19)
C53	0.090 (2)	0.0246 (13)	0.0566 (18)	0.0070 (15)	0.0214 (17)	−0.0010 (12)
C54	0.064 (2)	0.0500 (19)	0.092 (3)	0.0034 (16)	0.0055 (19)	−0.0236 (18)
N8	0.085 (4)	0.156 (8)	0.067 (4)	−0.042 (5)	0.024 (4)	−0.003 (4)
C55	0.101 (5)	0.062 (6)	0.031 (4)	−0.032 (5)	0.025 (5)	−0.005 (4)
C56	0.096 (6)	0.083 (9)	0.076 (7)	0.000 (7)	−0.021 (6)	0.044 (6)

Geometric parameters (Å, º) top

Ga1—O3	1.9175 (13)	Ga2—N6	2.0984 (16)
Ga1—O1	1.9215 (13)	O4—C38	1.313 (2)
Ga1—O2	1.9302 (13)	O5—C45	1.316 (2)
Ga1—N1	2.0668 (16)	O6—C52	1.321 (2)
Ga1—N3	2.0719 (16)	N4—C32	1.288 (2)
Ga1—N2	2.0976 (16)	N4—C27	1.467 (2)
O1—C12	1.318 (2)	N5—C39	1.280 (3)
O2—C19	1.312 (2)	N5—C28	1.478 (3)
O3—C26	1.321 (2)	N6—C46	1.284 (3)
N1—C6	1.288 (2)	N6—C29	1.474 (3)
N1—C1	1.475 (2)	C27—C30	1.542 (3)
N2—C13	1.284 (2)	C27—H27A	0.9900
N2—C2	1.474 (2)	C27—H27B	0.9900
N3—C20	1.282 (2)	C28—C30	1.535 (3)
N3—C3	1.468 (2)	C28—H28A	0.9900
C1—C4	1.548 (3)	C28—H28B	0.9900
C1—H1A	0.9900	C29—C30	1.531 (3)
C1—H1B	0.9900	C29—H29A	0.9900
C2—C4	1.542 (3)	C29—H29B	0.9900
C2—H2A	0.9900	C30—C31	1.531 (3)
C2—H2B	0.9900	C31—H31A	0.9800
C3—C4	1.540 (3)	C31—H31B	0.9800
C3—H3A	0.9900	C31—H31C	0.9800
C3—H3B	0.9900	C32—C33	1.436 (3)
C4—C5	1.530 (3)	C32—H32	0.9500
C5—H5A	0.9800	C33—C34	1.408 (3)
C5—H5B	0.9800	C33—C38	1.418 (3)
C5—H5C	0.9800	C34—C35	1.372 (3)
C6—C7	1.447 (3)	C34—H34	0.9500
C6—H6	0.9500	C35—C36	1.394 (3)
C7—C8	1.409 (3)	C35—H35	0.9500
C7—C12	1.416 (3)	C36—C37	1.373 (3)
C8—C9	1.373 (3)	C36—H36	0.9500
C8—H8	0.9500	C37—C38	1.413 (3)
C9—C10	1.393 (3)	C37—H37	0.9500
C9—H9	0.9500	C39—C40	1.440 (3)
C10—C11	1.379 (3)	C39—H39	0.9500
C10—H10	0.9500	C40—C41	1.402 (3)
C11—C12	1.413 (3)	C40—C45	1.413 (3)
C11—H11	0.9500	C41—C42	1.374 (4)
C13—C14	1.434 (3)	C41—H41	0.9500
C13—H13	0.9500	C42—C43	1.390 (4)
C14—C15	1.408 (3)	C42—H42	0.9500
C14—C19	1.421 (3)	C43—C44	1.375 (3)
C15—C16	1.369 (3)	C43—H43	0.9500
C15—H15	0.9500	C44—C45	1.419 (3)
C16—C17	1.396 (3)	C44—H44	0.9500
C16—H16	0.9500	C46—C47	1.441 (3)
C17—C18	1.381 (3)	C46—H46	0.9500
C17—H17	0.9500	C47—C48	1.414 (3)
C18—C19	1.410 (3)	C47—C52	1.419 (3)
C18—H18	0.9500	C48—C49	1.364 (3)
C20—C21	1.436 (3)	C48—H48	0.9500
C20—H20	0.9500	C49—C50	1.396 (3)
C21—C22	1.413 (3)	C49—H49	0.9500
C21—C26	1.417 (3)	C50—C51	1.380 (3)
C22—C23	1.362 (3)	C50—H50	0.9500
C22—H22	0.9500	C51—C52	1.407 (3)
C23—C24	1.393 (3)	C51—H51	0.9500
C23—H23	0.9500	N7—C53	1.126 (4)
C24—C25	1.376 (3)	C53—C54	1.435 (4)
C24—H24	0.9500	C54—H54A	0.9800
C25—C26	1.409 (3)	C54—H54B	0.9800
C25—H25	0.9500	C54—H54C	0.9800
Ga2—O6	1.9238 (14)	N8—C55	1.138 (9)
Ga2—O5	1.9239 (14)	C55—C56	1.464 (7)
Ga2—O4	1.9296 (13)	C56—H56A	0.9800
Ga2—N4	2.0583 (16)	C56—H56B	0.9800
Ga2—N5	2.0897 (18)	C56—H56C	0.9800

O3—Ga1—O1	92.70 (6)	O5—Ga2—N5	87.99 (6)
O3—Ga1—O2	94.28 (6)	O4—Ga2—N5	97.10 (6)
O1—Ga1—O2	91.39 (6)	N4—Ga2—N5	84.35 (7)
O3—Ga1—N1	95.36 (6)	O6—Ga2—N6	87.38 (6)
O1—Ga1—N1	89.77 (6)	O5—Ga2—N6	93.86 (6)
O2—Ga1—N1	170.22 (6)	O4—Ga2—N6	174.83 (6)
O3—Ga1—N3	89.22 (6)	N4—Ga2—N6	85.69 (6)
O1—Ga1—N3	174.65 (6)	N5—Ga2—N6	82.12 (7)
O2—Ga1—N3	93.44 (6)	C38—O4—Ga2	128.73 (12)
N1—Ga1—N3	85.08 (6)	C45—O5—Ga2	126.13 (13)
O3—Ga1—N2	174.19 (6)	C52—O6—Ga2	124.41 (13)
O1—Ga1—N2	92.79 (6)	C32—N4—C27	116.98 (17)
O2—Ga1—N2	87.50 (6)	C32—N4—Ga2	125.53 (13)
N1—Ga1—N2	82.74 (6)	C27—N4—Ga2	117.33 (12)
N3—Ga1—N2	85.15 (6)	C39—N5—C28	117.77 (19)
C12—O1—Ga1	129.23 (12)	C39—N5—Ga2	124.47 (15)
C19—O2—Ga1	128.71 (12)	C28—N5—Ga2	117.73 (13)
C26—O3—Ga1	129.25 (12)	C46—N6—C29	118.37 (18)
C6—N1—C1	117.43 (17)	C46—N6—Ga2	121.62 (15)
C6—N1—Ga1	125.09 (13)	C29—N6—Ga2	119.60 (13)
C1—N1—Ga1	117.36 (13)	N4—C27—C30	110.78 (16)
C13—N2—C2	117.85 (16)	N4—C27—H27A	109.5
C13—N2—Ga1	124.19 (13)	C30—C27—H27A	109.5
C2—N2—Ga1	117.90 (12)	N4—C27—H27B	109.5
C20—N3—C3	117.81 (16)	C30—C27—H27B	109.5
C20—N3—Ga1	125.21 (14)	H27A—C27—H27B	108.1
C3—N3—Ga1	116.74 (12)	N5—C28—C30	110.71 (17)
N1—C1—C4	109.32 (15)	N5—C28—H28A	109.5
N1—C1—H1A	109.8	C30—C28—H28A	109.5
C4—C1—H1A	109.8	N5—C28—H28B	109.5
N1—C1—H1B	109.8	C30—C28—H28B	109.5
C4—C1—H1B	109.8	H28A—C28—H28B	108.1
H1A—C1—H1B	108.3	N6—C29—C30	110.29 (17)
N2—C2—C4	109.46 (15)	N6—C29—H29A	109.6
N2—C2—H2A	109.8	C30—C29—H29A	109.6
C4—C2—H2A	109.8	N6—C29—H29B	109.6
N2—C2—H2B	109.8	C30—C29—H29B	109.6
C4—C2—H2B	109.8	H29A—C29—H29B	108.1
H2A—C2—H2B	108.2	C31—C30—C29	110.19 (18)
N3—C3—C4	110.14 (16)	C31—C30—C28	108.7 (2)
N3—C3—H3A	109.6	C29—C30—C28	109.88 (17)
C4—C3—H3A	109.6	C31—C30—C27	107.98 (18)
N3—C3—H3B	109.6	C29—C30—C27	109.15 (19)
C4—C3—H3B	109.6	C28—C30—C27	110.96 (17)
H3A—C3—H3B	108.1	C30—C31—H31A	109.5
C5—C4—C3	107.96 (17)	C30—C31—H31B	109.5
C5—C4—C2	109.08 (16)	H31A—C31—H31B	109.5
C3—C4—C2	109.90 (16)	C30—C31—H31C	109.5
C5—C4—C1	109.85 (17)	H31A—C31—H31C	109.5
C3—C4—C1	110.62 (16)	H31B—C31—H31C	109.5
C2—C4—C1	109.40 (16)	N4—C32—C33	125.58 (18)
C4—C5—H5A	109.5	N4—C32—H32	117.2
C4—C5—H5B	109.5	C33—C32—H32	117.2
H5A—C5—H5B	109.5	C34—C33—C38	120.46 (18)
C4—C5—H5C	109.5	C34—C33—C32	116.57 (18)
H5A—C5—H5C	109.5	C38—C33—C32	122.89 (17)
H5B—C5—H5C	109.5	C35—C34—C33	121.1 (2)
N1—C6—C7	125.26 (18)	C35—C34—H34	119.5
N1—C6—H6	117.4	C33—C34—H34	119.5
C7—C6—H6	117.4	C34—C35—C36	118.82 (19)
C8—C7—C12	119.92 (19)	C34—C35—H35	120.6
C8—C7—C6	116.42 (18)	C36—C35—H35	120.6
C12—C7—C6	123.18 (18)	C37—C36—C35	121.33 (19)
C9—C8—C7	121.5 (2)	C37—C36—H36	119.3
C9—C8—H8	119.3	C35—C36—H36	119.3
C7—C8—H8	119.3	C36—C37—C38	121.5 (2)
C8—C9—C10	118.9 (2)	C36—C37—H37	119.3
C8—C9—H9	120.6	C38—C37—H37	119.3
C10—C9—H9	120.6	O4—C38—C37	119.25 (18)
C11—C10—C9	121.1 (2)	O4—C38—C33	123.93 (17)
C11—C10—H10	119.5	C37—C38—C33	116.80 (18)
C9—C10—H10	119.5	N5—C39—C40	125.3 (2)
C10—C11—C12	121.3 (2)	N5—C39—H39	117.3
C10—C11—H11	119.3	C40—C39—H39	117.3
C12—C11—H11	119.3	C41—C40—C45	119.9 (2)
O1—C12—C11	118.23 (18)	C41—C40—C39	117.7 (2)
O1—C12—C7	124.37 (17)	C45—C40—C39	122.34 (19)
C11—C12—C7	117.34 (18)	C42—C41—C40	121.5 (2)
N2—C13—C14	125.08 (17)	C42—C41—H41	119.3
N2—C13—H13	117.5	C40—C41—H41	119.3
C14—C13—H13	117.5	C41—C42—C43	118.9 (2)
C15—C14—C19	119.84 (18)	C41—C42—H42	120.5
C15—C14—C13	116.94 (17)	C43—C42—H42	120.5
C19—C14—C13	122.51 (17)	C44—C43—C42	121.2 (2)
C16—C15—C14	122.03 (19)	C44—C43—H43	119.4
C16—C15—H15	119.0	C42—C43—H43	119.4
C14—C15—H15	119.0	C43—C44—C45	121.0 (2)
C15—C16—C17	118.4 (2)	C43—C44—H44	119.5
C15—C16—H16	120.8	C45—C44—H44	119.5
C17—C16—H16	120.8	O5—C45—C40	123.83 (19)
C18—C17—C16	121.2 (2)	O5—C45—C44	118.7 (2)
C18—C17—H17	119.4	C40—C45—C44	117.4 (2)
C16—C17—H17	119.4	N6—C46—C47	125.52 (19)
C17—C18—C19	121.59 (19)	N6—C46—H46	117.2
C17—C18—H18	119.2	C47—C46—H46	117.2
C19—C18—H18	119.2	C48—C47—C52	119.5 (2)
O2—C19—C18	118.49 (17)	C48—C47—C46	117.3 (2)
O2—C19—C14	124.48 (17)	C52—C47—C46	123.03 (19)
C18—C19—C14	116.94 (18)	C49—C48—C47	121.5 (2)
N3—C20—C21	126.00 (18)	C49—C48—H48	119.3
N3—C20—H20	117.0	C47—C48—H48	119.3
C21—C20—H20	117.0	C48—C49—C50	119.2 (2)
C22—C21—C26	119.79 (18)	C48—C49—H49	120.4
C22—C21—C20	117.58 (17)	C50—C49—H49	120.4
C26—C21—C20	122.42 (17)	C51—C50—C49	120.9 (2)
C23—C22—C21	121.60 (19)	C51—C50—H50	119.5
C23—C22—H22	119.2	C49—C50—H50	119.5
C21—C22—H22	119.2	C50—C51—C52	121.2 (2)
C22—C23—C24	118.88 (18)	C50—C51—H51	119.4
C22—C23—H23	120.6	C52—C51—H51	119.4
C24—C23—H23	120.6	O6—C52—C51	119.52 (19)
C25—C24—C23	121.10 (19)	O6—C52—C47	122.7 (2)
C25—C24—H24	119.5	C51—C52—C47	117.70 (19)
C23—C24—H24	119.5	N7—C53—C54	179.8 (4)
C24—C25—C26	121.47 (19)	C53—C54—H54A	109.5
C24—C25—H25	119.3	C53—C54—H54B	109.5
C26—C25—H25	119.3	H54A—C54—H54B	109.5
O3—C26—C25	118.51 (17)	C53—C54—H54C	109.5
O3—C26—C21	124.38 (17)	H54A—C54—H54C	109.5
C25—C26—C21	117.09 (17)	H54B—C54—H54C	109.5
O6—Ga2—O5	91.00 (6)	N8—C55—C56	173.9 (10)
O6—Ga2—O4	93.51 (6)	C55—C56—H56A	109.5
O5—Ga2—O4	91.22 (6)	C55—C56—H56B	109.5
O6—Ga2—N4	96.64 (6)	H56A—C56—H56B	109.5
O5—Ga2—N4	172.32 (7)	C55—C56—H56C	109.5
O4—Ga2—N4	89.15 (6)	H56A—C56—H56C	109.5
O6—Ga2—N5	169.36 (6)	H56B—C56—H56C	109.5

C6—N1—C1—C4	−134.82 (18)	C32—N4—C27—C30	134.21 (19)
Ga1—N1—C1—C4	41.39 (19)	Ga2—N4—C27—C30	−41.6 (2)
C13—N2—C2—C4	−144.97 (18)	C39—N5—C28—C30	140.67 (19)
Ga1—N2—C2—C4	37.7 (2)	Ga2—N5—C28—C30	−37.6 (2)
C20—N3—C3—C4	−132.89 (18)	C46—N6—C29—C30	154.60 (18)
Ga1—N3—C3—C4	41.7 (2)	Ga2—N6—C29—C30	−32.7 (2)
N3—C3—C4—C5	155.31 (17)	N6—C29—C30—C31	−159.72 (19)
N3—C3—C4—C2	−85.82 (19)	N6—C29—C30—C28	80.6 (2)
N3—C3—C4—C1	35.1 (2)	N6—C29—C30—C27	−41.3 (2)
N2—C2—C4—C5	156.62 (17)	N5—C28—C30—C31	−161.28 (18)
N2—C2—C4—C3	38.4 (2)	N5—C28—C30—C29	−40.7 (2)
N2—C2—C4—C1	−83.20 (19)	N5—C28—C30—C27	80.2 (2)
N1—C1—C4—C5	157.89 (17)	N4—C27—C30—C31	−154.34 (19)
N1—C1—C4—C3	−83.03 (19)	N4—C27—C30—C29	85.9 (2)
N1—C1—C4—C2	38.2 (2)	N4—C27—C30—C28	−35.4 (2)
C1—N1—C6—C7	168.79 (18)	C27—N4—C32—C33	−174.73 (19)
Ga1—N1—C6—C7	−7.1 (3)	Ga2—N4—C32—C33	0.6 (3)
N1—C6—C7—C8	−179.54 (19)	N4—C32—C33—C34	−172.83 (19)
N1—C6—C7—C12	−7.5 (3)	N4—C32—C33—C38	10.3 (3)
C12—C7—C8—C9	−0.3 (3)	C38—C33—C34—C35	−1.9 (3)
C6—C7—C8—C9	172.0 (2)	C32—C33—C34—C35	−178.84 (19)
C7—C8—C9—C10	−0.9 (4)	C33—C34—C35—C36	1.4 (3)
C8—C9—C10—C11	1.0 (4)	C34—C35—C36—C37	0.2 (3)
C9—C10—C11—C12	0.2 (3)	C35—C36—C37—C38	−1.3 (3)
Ga1—O1—C12—C11	−173.14 (13)	Ga2—O4—C38—C37	162.04 (14)
Ga1—O1—C12—C7	9.6 (3)	Ga2—O4—C38—C33	−19.5 (3)
C10—C11—C12—O1	−178.80 (18)	C36—C37—C38—O4	179.43 (18)
C10—C11—C12—C7	−1.4 (3)	C36—C37—C38—C33	0.8 (3)
C8—C7—C12—O1	178.68 (18)	C34—C33—C38—O4	−177.79 (18)
C6—C7—C12—O1	6.9 (3)	C32—C33—C38—O4	−1.0 (3)
C8—C7—C12—C11	1.4 (3)	C34—C33—C38—C37	0.7 (3)
C6—C7—C12—C11	−170.34 (17)	C32—C33—C38—C37	177.52 (18)
C2—N2—C13—C14	167.67 (18)	C28—N5—C39—C40	−178.1 (2)
Ga1—N2—C13—C14	−15.2 (3)	Ga2—N5—C39—C40	0.1 (3)
N2—C13—C14—C15	−177.88 (19)	N5—C39—C40—C41	−165.2 (2)
N2—C13—C14—C19	−7.6 (3)	N5—C39—C40—C45	14.7 (3)
C19—C14—C15—C16	−1.6 (3)	C45—C40—C41—C42	−1.2 (3)
C13—C14—C15—C16	169.0 (2)	C39—C40—C41—C42	178.7 (2)
C14—C15—C16—C17	−1.0 (3)	C40—C41—C42—C43	2.9 (4)
C15—C16—C17—C18	2.2 (3)	C41—C42—C43—C44	−1.2 (4)
C16—C17—C18—C19	−0.8 (3)	C42—C43—C44—C45	−2.2 (4)
Ga1—O2—C19—C18	−169.20 (13)	Ga2—O5—C45—C40	−31.3 (3)
Ga1—O2—C19—C14	14.2 (3)	Ga2—O5—C45—C44	151.55 (16)
C17—C18—C19—O2	−178.59 (19)	C41—C40—C45—O5	−179.26 (19)
C17—C18—C19—C14	−1.7 (3)	C39—C40—C45—O5	0.9 (3)
C15—C14—C19—O2	179.53 (18)	C41—C40—C45—C44	−2.1 (3)
C13—C14—C19—O2	9.5 (3)	C39—C40—C45—C44	178.0 (2)
C15—C14—C19—C18	2.9 (3)	C43—C44—C45—O5	−178.9 (2)
C13—C14—C19—C18	−167.11 (18)	C43—C44—C45—C40	3.8 (3)
C3—N3—C20—C21	171.62 (19)	C29—N6—C46—C47	−174.31 (19)
Ga1—N3—C20—C21	−2.5 (3)	Ga2—N6—C46—C47	13.2 (3)
N3—C20—C21—C22	174.4 (2)	N6—C46—C47—C48	−173.7 (2)
N3—C20—C21—C26	−10.9 (3)	N6—C46—C47—C52	10.2 (3)
C26—C21—C22—C23	0.0 (3)	C52—C47—C48—C49	−1.1 (3)
C20—C21—C22—C23	174.9 (2)	C46—C47—C48—C49	−177.4 (2)
C21—C22—C23—C24	−1.3 (3)	C47—C48—C49—C50	1.5 (3)
C22—C23—C24—C25	0.3 (3)	C48—C49—C50—C51	−0.5 (3)
C23—C24—C25—C26	2.0 (3)	C49—C50—C51—C52	−0.8 (3)
Ga1—O3—C26—C25	−168.30 (14)	Ga2—O6—C52—C51	149.73 (15)
Ga1—O3—C26—C21	13.5 (3)	Ga2—O6—C52—C47	−33.5 (2)
C24—C25—C26—O3	178.51 (19)	C50—C51—C52—O6	178.01 (18)
C24—C25—C26—C21	−3.2 (3)	C50—C51—C52—C47	1.1 (3)
C22—C21—C26—O3	−179.63 (18)	C48—C47—C52—O6	−176.98 (18)
C20—C21—C26—O3	5.8 (3)	C46—C47—C52—O6	−0.9 (3)
C22—C21—C26—C25	2.2 (3)	C48—C47—C52—C51	−0.2 (3)
C20—C21—C26—C25	−172.45 (19)	C46—C47—C52—C51	175.84 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C32—H32···O1	0.95	2.51	3.333 (2)	146
C34—H34···O1	0.95	2.88	3.574 (2)	131
C15—H15···O1ⁱ	0.95	2.65	3.499 (2)	149
C24—H24···O2ⁱⁱ	0.95	2.83	3.610 (2)	140
C54—H54B···O2ⁱⁱⁱ	0.98	2.31	3.282 (3)	171
C27—H27A···O3	0.99	2.89	3.697 (2)	140
C6—H6···O4^iv	0.95	2.68	3.557 (2)	153
C8—H8···O4^iv	0.95	2.84	3.642 (3)	143
C8—H8···O5^iv	0.95	2.91	3.806 (3)	157
C48—H48···O5^v	0.95	2.55	3.413 (3)	151
C6—H6···O6^iv	0.95	2.54	3.325 (2)	140
C22—H22···O6ⁱⁱ	0.95	2.56	3.502 (2)	173
C28—H28A···N7	0.99	2.91	3.680 (4)	135
C29—H29B···N7	0.99	2.72	3.554 (4)	143
C31—H31C···N7	0.98	2.85	3.703 (4)	146
C10—H10···N8^vi	0.95	2.63	3.508 (7)	154

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

({[(2,2-Bis{[(2-oxidobenzylidene)amino-κ²N,O]methyl}propyl)imino]methyl}phenololato-κ²N,O)indium(III) dichloromethane monosolvate (2) top

Crystal data top

[In(C₂₆H₂₄N₃O₃)]·CH₂Cl₂	F(000) = 1264
M_r = 626.23	D_x = 1.591 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.0704 (2) Å	Cell parameters from 17154 reflections
b = 16.2514 (4) Å	θ = 2.4–32.9°
c = 16.1749 (4) Å	µ = 1.14 mm⁻¹
β = 99.130 (2)°	T = 100 K
V = 2613.62 (11) Å³	Needle, colourless
Z = 4	0.34 × 0.14 × 0.07 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	8621 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Mo) X-ray Source	7401 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.037
Detector resolution: 10.0000 pixels mm^-1	θ_max = 33.1°, θ_min = 2.5°
ω scans	h = −15→13
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2019)	k = −21→24
T_min = 0.676, T_max = 1.000	l = −22→24
31229 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.064	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0232P)² + 0.8708P] where P = (F_o² + 2F_c²)/3
8621 reflections	(Δ/σ)_max = 0.003
326 parameters	Δρ_max = 0.62 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
In1	0.44234 (2)	0.76734 (2)	0.60863 (2)	0.01380 (4)
O1	0.30272 (11)	0.85701 (7)	0.63247 (7)	0.0179 (2)
O2	0.40058 (12)	0.78742 (7)	0.47927 (7)	0.0192 (2)
O3	0.29061 (11)	0.67774 (7)	0.60288 (8)	0.0194 (2)
N1	0.51813 (14)	0.77671 (8)	0.74596 (8)	0.0165 (3)
N2	0.63141 (13)	0.83756 (8)	0.59915 (8)	0.0168 (3)
N3	0.58328 (13)	0.65939 (8)	0.62197 (8)	0.0161 (3)
C1	0.65051 (17)	0.73976 (10)	0.77773 (10)	0.0196 (3)
H1A	0.638433	0.682044	0.789904	0.024*
H1B	0.688637	0.766753	0.829572	0.024*
C2	0.73966 (16)	0.83319 (10)	0.67196 (10)	0.0196 (3)
H2A	0.723603	0.874388	0.712624	0.024*
H2B	0.824759	0.845933	0.653984	0.024*
C3	0.72684 (15)	0.67764 (10)	0.64906 (11)	0.0195 (3)
H3A	0.766964	0.693095	0.600612	0.023*
H3B	0.771881	0.628327	0.672869	0.023*
C4	0.74959 (16)	0.74748 (10)	0.71434 (11)	0.0183 (3)
C5	0.89334 (18)	0.73819 (11)	0.76248 (12)	0.0250 (4)
H5A	0.955679	0.735006	0.723426	0.038*
H5B	0.899158	0.688889	0.795556	0.038*
H5C	0.914876	0.784863	0.798484	0.038*
C6	0.44813 (16)	0.80394 (10)	0.79995 (10)	0.0174 (3)
H6	0.483528	0.795509	0.855990	0.021*
C7	0.31986 (16)	0.84640 (10)	0.78311 (10)	0.0168 (3)
C8	0.26184 (17)	0.86798 (11)	0.85429 (11)	0.0228 (3)
H8	0.301662	0.849411	0.906786	0.027*
C9	0.14814 (18)	0.91570 (12)	0.84762 (12)	0.0282 (4)
H9	0.112293	0.929965	0.895214	0.034*
C10	0.08675 (18)	0.94264 (12)	0.76874 (12)	0.0274 (4)
H10	0.009923	0.975165	0.763955	0.033*
C11	0.13927 (17)	0.92134 (11)	0.69770 (11)	0.0225 (3)
H11	0.096553	0.939458	0.645680	0.027*
C12	0.25668 (16)	0.87255 (10)	0.70252 (10)	0.0173 (3)
C13	0.64839 (16)	0.88497 (10)	0.53775 (10)	0.0179 (3)
H13	0.729159	0.913720	0.543284	0.021*
C14	0.55527 (16)	0.89815 (10)	0.46131 (10)	0.0170 (3)
C15	0.58775 (17)	0.96171 (10)	0.40835 (10)	0.0208 (3)
H15	0.666516	0.991607	0.423808	0.025*
C16	0.50515 (18)	0.98046 (10)	0.33410 (10)	0.0223 (3)
H16	0.528051	1.022498	0.299972	0.027*
C17	0.38735 (18)	0.93571 (11)	0.31103 (10)	0.0219 (3)
H17	0.330829	0.948394	0.261440	0.026*
C18	0.35340 (17)	0.87253 (10)	0.36106 (10)	0.0193 (3)
H18	0.274314	0.843322	0.344230	0.023*
C19	0.43559 (15)	0.85131 (10)	0.43689 (9)	0.0159 (3)
C20	0.54875 (15)	0.58334 (10)	0.61401 (10)	0.0160 (3)
H20	0.617996	0.544907	0.622622	0.019*
C21	0.41363 (15)	0.55107 (10)	0.59307 (9)	0.0151 (3)
C22	0.40479 (16)	0.46536 (10)	0.57930 (10)	0.0190 (3)
H22	0.483626	0.435241	0.580611	0.023*
C23	0.28335 (17)	0.42487 (10)	0.56399 (11)	0.0219 (3)
H23	0.279604	0.368547	0.553733	0.026*
C24	0.16602 (16)	0.47043 (11)	0.56423 (10)	0.0208 (3)
H24	0.083232	0.443813	0.555089	0.025*
C25	0.17059 (16)	0.55445 (10)	0.57782 (10)	0.0191 (3)
H25	0.090731	0.583086	0.578182	0.023*
C26	0.29404 (15)	0.59796 (10)	0.59120 (9)	0.0154 (3)
Cl1	0.03175 (6)	0.90823 (3)	0.44842 (3)	0.03845 (12)
Cl2	−0.06104 (5)	0.74882 (3)	0.49805 (4)	0.03799 (12)
C27	0.07878 (16)	0.80653 (11)	0.47822 (12)	0.0239 (4)
H27A	0.118092	0.780353	0.433928	0.029*
H27B	0.146259	0.807633	0.528180	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
In1	0.01471 (6)	0.01451 (6)	0.01177 (5)	−0.00124 (4)	0.00086 (4)	−0.00034 (4)
O1	0.0219 (5)	0.0169 (5)	0.0149 (5)	0.0031 (4)	0.0029 (4)	0.0005 (4)
O2	0.0230 (6)	0.0218 (6)	0.0123 (5)	−0.0078 (5)	0.0012 (4)	−0.0006 (4)
O3	0.0149 (5)	0.0168 (6)	0.0264 (6)	−0.0005 (4)	0.0030 (4)	−0.0010 (5)
N1	0.0185 (6)	0.0164 (6)	0.0140 (6)	−0.0020 (5)	0.0012 (5)	0.0012 (5)
N2	0.0182 (6)	0.0156 (6)	0.0154 (6)	−0.0023 (5)	−0.0002 (5)	−0.0012 (5)
N3	0.0138 (6)	0.0177 (6)	0.0170 (6)	−0.0022 (5)	0.0030 (5)	−0.0025 (5)
C1	0.0215 (8)	0.0204 (8)	0.0150 (7)	0.0015 (6)	−0.0027 (6)	0.0019 (6)
C2	0.0189 (7)	0.0198 (8)	0.0184 (8)	−0.0044 (6)	−0.0023 (6)	0.0000 (6)
C3	0.0122 (7)	0.0207 (8)	0.0253 (8)	−0.0018 (6)	0.0016 (6)	−0.0007 (6)
C4	0.0164 (7)	0.0179 (7)	0.0190 (8)	−0.0021 (6)	−0.0022 (6)	0.0004 (6)
C5	0.0200 (8)	0.0253 (9)	0.0270 (9)	−0.0036 (7)	−0.0049 (7)	0.0019 (7)
C6	0.0232 (8)	0.0159 (7)	0.0126 (7)	−0.0067 (6)	0.0012 (6)	0.0010 (6)
C7	0.0188 (7)	0.0161 (7)	0.0156 (7)	−0.0059 (6)	0.0036 (6)	−0.0006 (6)
C8	0.0222 (8)	0.0287 (9)	0.0180 (8)	−0.0089 (7)	0.0051 (6)	−0.0019 (7)
C9	0.0229 (8)	0.0380 (11)	0.0263 (9)	−0.0056 (8)	0.0117 (7)	−0.0083 (8)
C10	0.0190 (8)	0.0322 (10)	0.0317 (10)	0.0003 (7)	0.0064 (7)	−0.0065 (8)
C11	0.0215 (8)	0.0232 (8)	0.0228 (8)	0.0006 (7)	0.0031 (7)	−0.0015 (7)
C12	0.0195 (7)	0.0138 (7)	0.0188 (8)	−0.0043 (6)	0.0035 (6)	−0.0011 (6)
C13	0.0177 (7)	0.0159 (7)	0.0205 (8)	−0.0028 (6)	0.0045 (6)	−0.0024 (6)
C14	0.0204 (7)	0.0153 (7)	0.0158 (7)	−0.0001 (6)	0.0043 (6)	−0.0014 (6)
C15	0.0249 (8)	0.0172 (8)	0.0205 (8)	−0.0037 (6)	0.0039 (6)	−0.0011 (6)
C16	0.0333 (9)	0.0165 (8)	0.0179 (8)	−0.0006 (7)	0.0060 (7)	0.0027 (6)
C17	0.0298 (9)	0.0218 (8)	0.0140 (7)	0.0040 (7)	0.0036 (6)	−0.0004 (6)
C18	0.0210 (8)	0.0220 (8)	0.0147 (7)	−0.0011 (6)	0.0024 (6)	−0.0034 (6)
C19	0.0194 (7)	0.0160 (7)	0.0133 (7)	0.0011 (6)	0.0053 (6)	−0.0026 (5)
C20	0.0154 (7)	0.0167 (7)	0.0163 (7)	0.0008 (6)	0.0031 (6)	−0.0004 (6)
C21	0.0167 (7)	0.0163 (7)	0.0122 (7)	−0.0024 (6)	0.0024 (5)	0.0010 (5)
C22	0.0190 (7)	0.0177 (8)	0.0195 (8)	−0.0005 (6)	0.0007 (6)	0.0005 (6)
C23	0.0253 (8)	0.0159 (8)	0.0235 (8)	−0.0057 (7)	0.0010 (7)	0.0017 (6)
C24	0.0179 (7)	0.0229 (8)	0.0206 (8)	−0.0070 (6)	0.0006 (6)	0.0030 (6)
C25	0.0153 (7)	0.0224 (8)	0.0193 (8)	−0.0022 (6)	0.0020 (6)	0.0018 (6)
C26	0.0167 (7)	0.0180 (7)	0.0114 (7)	−0.0028 (6)	0.0023 (5)	0.0017 (5)
Cl1	0.0511 (3)	0.0208 (2)	0.0417 (3)	0.0032 (2)	0.0019 (2)	−0.00014 (19)
Cl2	0.0281 (2)	0.0428 (3)	0.0453 (3)	−0.0093 (2)	0.0126 (2)	0.0067 (2)
C27	0.0167 (7)	0.0207 (8)	0.0340 (10)	−0.0018 (6)	0.0030 (7)	−0.0023 (7)

Geometric parameters (Å, º) top

In1—O1	2.1027 (11)	C9—H9	0.9300
In1—O2	2.0935 (11)	C9—C10	1.397 (3)
In1—O3	2.1020 (11)	C10—H10	0.9300
In1—N1	2.2365 (14)	C10—C11	1.383 (2)
In1—N2	2.2458 (13)	C11—H11	0.9300
In1—N3	2.2453 (13)	C11—C12	1.416 (2)
O1—C12	1.3151 (19)	C13—H13	0.9300
O2—C19	1.3224 (19)	C13—C14	1.444 (2)
O3—C26	1.3116 (19)	C14—C15	1.413 (2)
N1—C1	1.478 (2)	C14—C19	1.427 (2)
N1—C6	1.285 (2)	C15—H15	0.9300
N2—C2	1.474 (2)	C15—C16	1.382 (2)
N2—C13	1.290 (2)	C16—H16	0.9300
N3—C3	1.473 (2)	C16—C17	1.391 (3)
N3—C20	1.285 (2)	C17—H17	0.9300
C1—H1A	0.9700	C17—C18	1.383 (2)
C1—H1B	0.9700	C18—H18	0.9300
C1—C4	1.545 (2)	C18—C19	1.409 (2)
C2—H2A	0.9700	C20—H20	0.9300
C2—H2B	0.9700	C20—C21	1.447 (2)
C2—C4	1.549 (2)	C21—C22	1.411 (2)
C3—H3A	0.9700	C21—C26	1.421 (2)
C3—H3B	0.9700	C22—H22	0.9300
C3—C4	1.542 (2)	C22—C23	1.376 (2)
C4—C5	1.538 (2)	C23—H23	0.9300
C5—H5A	0.9600	C23—C24	1.395 (2)
C5—H5B	0.9600	C24—H24	0.9300
C5—H5C	0.9600	C24—C25	1.383 (2)
C6—H6	0.9300	C25—H25	0.9300
C6—C7	1.452 (2)	C25—C26	1.417 (2)
C7—C8	1.415 (2)	Cl1—C27	1.7651 (18)
C7—C12	1.422 (2)	Cl2—C27	1.7631 (17)
C8—H8	0.9300	C27—H27A	0.9700
C8—C9	1.373 (3)	C27—H27B	0.9700

O1—In1—N1	84.46 (5)	C7—C8—H8	119.2
O1—In1—N2	105.02 (5)	C9—C8—C7	121.52 (17)
O1—In1—N3	162.70 (5)	C9—C8—H8	119.2
O2—In1—O1	92.35 (5)	C8—C9—H9	120.3
O2—In1—O3	91.97 (5)	C8—C9—C10	119.44 (16)
O2—In1—N1	164.77 (5)	C10—C9—H9	120.3
O2—In1—N2	83.71 (5)	C9—C10—H10	119.7
O2—In1—N3	103.97 (5)	C11—C10—C9	120.54 (17)
O3—In1—O1	89.18 (4)	C11—C10—H10	119.7
O3—In1—N1	102.84 (5)	C10—C11—H11	119.3
O3—In1—N2	165.28 (5)	C10—C11—C12	121.38 (17)
O3—In1—N3	84.66 (5)	C12—C11—H11	119.3
N1—In1—N2	82.75 (5)	O1—C12—C7	124.40 (15)
N1—In1—N3	81.19 (5)	O1—C12—C11	117.76 (15)
N3—In1—N2	82.75 (5)	C11—C12—C7	117.79 (15)
C12—O1—In1	128.94 (10)	N2—C13—H13	116.5
C19—O2—In1	127.79 (10)	N2—C13—C14	126.90 (15)
C26—O3—In1	130.97 (10)	C14—C13—H13	116.5
C1—N1—In1	117.67 (10)	C15—C14—C13	116.49 (15)
C6—N1—In1	124.12 (11)	C15—C14—C19	119.25 (15)
C6—N1—C1	117.74 (14)	C19—C14—C13	124.26 (14)
C2—N2—In1	116.64 (10)	C14—C15—H15	119.2
C13—N2—In1	125.01 (11)	C16—C15—C14	121.52 (16)
C13—N2—C2	118.19 (13)	C16—C15—H15	119.2
C3—N3—In1	116.55 (10)	C15—C16—H16	120.4
C20—N3—In1	125.81 (11)	C15—C16—C17	119.20 (15)
C20—N3—C3	117.44 (14)	C17—C16—H16	120.4
N1—C1—H1A	109.2	C16—C17—H17	119.7
N1—C1—H1B	109.2	C18—C17—C16	120.70 (16)
N1—C1—C4	112.22 (13)	C18—C17—H17	119.7
H1A—C1—H1B	107.9	C17—C18—H18	119.2
C4—C1—H1A	109.2	C17—C18—C19	121.68 (16)
C4—C1—H1B	109.2	C19—C18—H18	119.2
N2—C2—H2A	109.1	O2—C19—C14	123.92 (14)
N2—C2—H2B	109.1	O2—C19—C18	118.37 (14)
N2—C2—C4	112.62 (13)	C18—C19—C14	117.64 (14)
H2A—C2—H2B	107.8	N3—C20—H20	116.5
C4—C2—H2A	109.1	N3—C20—C21	126.97 (15)
C4—C2—H2B	109.1	C21—C20—H20	116.5
N3—C3—H3A	109.1	C22—C21—C20	115.34 (14)
N3—C3—H3B	109.1	C22—C21—C26	119.59 (14)
N3—C3—C4	112.59 (13)	C26—C21—C20	124.93 (14)
H3A—C3—H3B	107.8	C21—C22—H22	118.9
C4—C3—H3A	109.1	C23—C22—C21	122.16 (16)
C4—C3—H3B	109.1	C23—C22—H22	118.9
C1—C4—C2	111.33 (14)	C22—C23—H23	120.8
C3—C4—C1	110.68 (13)	C22—C23—C24	118.34 (16)
C3—C4—C2	111.51 (14)	C24—C23—H23	120.8
C5—C4—C1	108.12 (14)	C23—C24—H24	119.4
C5—C4—C2	107.57 (13)	C25—C24—C23	121.18 (15)
C5—C4—C3	107.45 (14)	C25—C24—H24	119.4
C4—C5—H5A	109.5	C24—C25—H25	119.2
C4—C5—H5B	109.5	C24—C25—C26	121.57 (15)
C4—C5—H5C	109.5	C26—C25—H25	119.2
H5A—C5—H5B	109.5	O3—C26—C21	124.64 (14)
H5A—C5—H5C	109.5	O3—C26—C25	118.23 (14)
H5B—C5—H5C	109.5	C25—C26—C21	117.11 (14)
N1—C6—H6	116.4	Cl1—C27—H27A	109.4
N1—C6—C7	127.16 (15)	Cl1—C27—H27B	109.4
C7—C6—H6	116.4	Cl2—C27—Cl1	111.12 (9)
C8—C7—C6	115.79 (15)	Cl2—C27—H27A	109.4
C8—C7—C12	119.30 (15)	Cl2—C27—H27B	109.4
C12—C7—C6	124.71 (14)	H27A—C27—H27B	108.0

In1—O1—C12—C7	18.4 (2)	C6—C7—C12—C11	−173.00 (15)
In1—O1—C12—C11	−164.25 (11)	C7—C8—C9—C10	1.0 (3)
In1—O2—C19—C14	31.0 (2)	C8—C7—C12—O1	179.02 (15)
In1—O2—C19—C18	−152.00 (11)	C8—C7—C12—C11	1.6 (2)
In1—O3—C26—C21	11.0 (2)	C8—C9—C10—C11	0.3 (3)
In1—O3—C26—C25	−170.70 (11)	C9—C10—C11—C12	−0.6 (3)
In1—N1—C1—C4	34.62 (17)	C10—C11—C12—O1	−177.97 (16)
In1—N1—C6—C7	−11.7 (2)	C10—C11—C12—C7	−0.4 (2)
In1—N2—C2—C4	36.43 (16)	C12—C7—C8—C9	−2.0 (2)
In1—N2—C13—C14	−4.6 (2)	C13—N2—C2—C4	−147.93 (15)
In1—N3—C3—C4	37.20 (17)	C13—C14—C15—C16	−179.20 (15)
In1—N3—C20—C21	1.6 (2)	C13—C14—C19—O2	−4.1 (2)
N1—C1—C4—C2	41.27 (18)	C13—C14—C19—C18	178.85 (15)
N1—C1—C4—C3	−83.35 (17)	C14—C15—C16—C17	0.0 (3)
N1—C1—C4—C5	159.22 (14)	C15—C14—C19—O2	175.61 (14)
N1—C6—C7—C8	178.28 (16)	C15—C14—C19—C18	−1.5 (2)
N1—C6—C7—C12	−6.9 (3)	C15—C16—C17—C18	−0.7 (3)
N2—C2—C4—C1	−84.71 (17)	C16—C17—C18—C19	0.3 (3)
N2—C2—C4—C3	39.44 (18)	C17—C18—C19—O2	−176.42 (15)
N2—C2—C4—C5	157.01 (14)	C17—C18—C19—C14	0.8 (2)
N2—C13—C14—C15	171.32 (16)	C19—C14—C15—C16	1.1 (2)
N2—C13—C14—C19	−9.0 (3)	C20—N3—C3—C4	−137.89 (15)
N3—C3—C4—C1	40.04 (19)	C20—C21—C22—C23	175.90 (15)
N3—C3—C4—C2	−84.47 (17)	C20—C21—C26—O3	4.7 (2)
N3—C3—C4—C5	157.89 (14)	C20—C21—C26—C25	−173.64 (14)
N3—C20—C21—C22	173.34 (16)	C21—C22—C23—C24	−1.6 (3)
N3—C20—C21—C26	−11.0 (3)	C22—C21—C26—O3	−179.78 (15)
C1—N1—C6—C7	176.28 (15)	C22—C21—C26—C25	1.9 (2)
C2—N2—C13—C14	−179.82 (15)	C22—C23—C24—C25	1.3 (3)
C3—N3—C20—C21	176.14 (15)	C23—C24—C25—C26	0.6 (3)
C6—N1—C1—C4	−152.81 (14)	C24—C25—C26—O3	179.35 (15)
C6—C7—C8—C9	173.12 (16)	C24—C25—C26—C21	−2.2 (2)
C6—C7—C12—O1	4.4 (3)	C26—C21—C22—C23	0.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.93	2.65	3.3596 (19)	134
C8—H8···O2ⁱ	0.93	2.63	3.394 (2)	139
C27—H27B···O1	0.97	2.26	3.193 (2)	160
C27—H27B···O2	0.97	2.82	3.253 (2)	108
C27—H27B···O3	0.97	2.73	3.411 (2)	127

Symmetry code: (i) x, −y+3/2, z+1/2.

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Crystal structures of {1,1,1-tris­[(salicylaldimino)­meth­yl]ethane}­gallium as both a pyridine solvate and an aceto­nitrile 0.75-solvate and {1,1,1-tris[(salicylaldimino)­meth­yl]ethane}­indium di­chloro­methane solvate

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structures of {1,1,1-tris[(salicylaldimino)methyl]ethane}gallium as both a pyridine solvate and an acetonitrile 0.75-solvate and {1,1,1-tris[(salicylaldimino)methyl]ethane}indium dichloromethane solvate