Redetermination of the crystal structure of bis­(tri-2-pyridyl­amine)­iron(II) bis­(perchlorate), and a new refinement of the isotypic nickel(II) analogue: treatment of the perchlorate anion disorder

The crystal structure of bis­(tri-2-pyridyl­amine)­iron(II) bis­(perchlorate) has been redetermined, and that of the isotypic bis­(tri-2-pyridyl­amine)­nickel(II) bis­(perchlorate) complex has been rerefined. In each case, the perchlorate anion is disordered over four sets of atomic sites, and the ions are linked by C—H...O hydrogen bonds to form a supra­molecular three-dimensional framework.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in solvent or counterion
• R factor = 0.049
• wR factor = 0.114
• Data-to-parameter ratio = 12.1

Structure: III

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in solvent or counterion
• R factor = 0.043
• wR factor = 0.109
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     13.327 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.338 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         20 Note
PLAT068_ALERT_1_G Reported F000 Differs from Calcd (or Missing)...     Please Check
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records         15 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          3 Report
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )       100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  3  )       100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  4  )       100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  5  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ...... Resd  2          2.08 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ...... Resd  3          1.33 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ...... Resd  4          1.28 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ...... Resd  5          0.31 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O43      ..C25              2.99 Ang.
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         61 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
  15 ALERT level G = General information/check it is not something unexpected

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




Datablock: III



Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.080 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         20 Note
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records         15 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          3 Report
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )       100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  3  )       100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  4  )       100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  5  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ...... Resd  2          2.12 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ...... Resd  3          1.40 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ...... Resd  4          1.22 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ...... Resd  5          0.26 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O42      ..C24              2.97 Ang.
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         61 Note
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        108 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

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

   1 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
   4 ALERT type 3 Indicator that the structure quality may be low
  11 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002) for (I); SMART (Bruker, 2007) for (III). Cell refinement: X-AREA (Stoe & Cie, 2002) for (I); SAINT (Bruker, 2007) for (III). Data reduction: X-RED32 (Stoe & Cie, 2002) for (I); SAINT (Bruker, 2007) for (III). Program(s) used to solve structure: SHELXS86 (Sheldrick, 2008) for (I); SHELXS (Sheldrick, 2008) for (III). For both structures, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

Bis(tri-2-pyridylamine)iron(II) bis(perchlorate) (I)

Crystal data

[Fe(C15H12N4)2](ClO4)2	F(000) = 768
Mr = 751.32	Dx = 1.571 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.3251 (7) Å	Cell parameters from 3322 reflections
b = 17.4731 (11) Å	θ = 2.2–26.6°
c = 11.0495 (9) Å	µ = 0.71 mm^−1
β = 98.716 (7)°	T = 296 K
V = 1588.8 (2) Å^3	Prism, red
Z = 2	0.42 × 0.21 × 0.12 mm

Data collection

STOE IPDS 2 diffractometer	3287 independent reflections
Radiation source: fine focus sealed tube	2098 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.074
rotation method scans	θmax = 26.5°, θmin = 2.2°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −9→10
Tmin = 0.899, Tmax = 0.919	k = −21→21
13886 measured reflections	l = −13→13

Refinement

Refinement on F^2	61 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.114	w = 1/[σ^2(Fo^2) + (0.0569P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max = 0.001
3287 reflections	Δρmax = 0.37 e Å^−3
272 parameters	Δρmin = −0.21 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Fe1	0.5000	0.5000	0.5000	0.03891 (18)
N1	0.3758 (3)	0.44032 (16)	0.7164 (2)	0.0448 (6)
N11	0.3667 (3)	0.55621 (16)	0.6050 (2)	0.0423 (6)
C12	0.3230 (4)	0.51828 (18)	0.7007 (3)	0.0418 (8)
C13	0.2334 (4)	0.5506 (2)	0.7821 (3)	0.0549 (9)
H13	0.2080	0.5228	0.8485	0.066*
C14	0.1822 (5)	0.6252 (2)	0.7631 (4)	0.0624 (10)
H14	0.1197	0.6485	0.8157	0.075*
C15	0.2251 (4)	0.6648 (2)	0.6648 (3)	0.0582 (9)
H15	0.1917	0.7152	0.6503	0.070*
C16	0.3174 (4)	0.6291 (2)	0.5889 (3)	0.0493 (8)
H16	0.3470	0.6565	0.5236	0.059*
N21	0.3542 (3)	0.41161 (15)	0.5048 (2)	0.0420 (6)
C22	0.3112 (4)	0.39352 (19)	0.6139 (3)	0.0415 (7)
C23	0.2113 (4)	0.3321 (2)	0.6298 (3)	0.0504 (8)
H23	0.1831	0.3214	0.7063	0.061*
C24	0.1550 (4)	0.2877 (2)	0.5306 (4)	0.0580 (9)
H24	0.0878	0.2461	0.5387	0.070*
C25	0.1988 (4)	0.3052 (2)	0.4180 (3)	0.0553 (9)
H25	0.1625	0.2752	0.3498	0.066*
C26	0.2966 (4)	0.3674 (2)	0.4084 (3)	0.0473 (8)
H26	0.3241	0.3794	0.3322	0.057*
N31	0.6312 (3)	0.45990 (15)	0.6513 (2)	0.0428 (6)
C32	0.5506 (4)	0.43509 (19)	0.7411 (3)	0.0439 (7)
C33	0.6251 (5)	0.4056 (2)	0.8493 (3)	0.0568 (9)
H33	0.5643	0.3899	0.9088	0.068*
C34	0.7919 (5)	0.3995 (2)	0.8690 (3)	0.0645 (10)
H34	0.8458	0.3788	0.9416	0.077*
C35	0.8774 (5)	0.4245 (2)	0.7794 (3)	0.0594 (9)
H35	0.9902	0.4214	0.7911	0.071*
C36	0.7957 (4)	0.4539 (2)	0.6731 (3)	0.0504 (8)
H36	0.8551	0.4705	0.6133	0.061*
Cl1	0.2289 (10)	0.3486 (6)	0.0675 (8)	0.0622 (9)	0.415 (3)
O11	0.1418 (13)	0.4123 (5)	0.1027 (19)	0.097 (3)	0.415 (3)
O12	0.223 (3)	0.3449 (12)	−0.0609 (8)	0.111 (2)	0.415 (3)
O13	0.3942 (10)	0.3496 (8)	0.1242 (11)	0.101 (4)	0.415 (3)
O14	0.1517 (15)	0.2816 (6)	0.1090 (9)	0.090 (3)	0.415 (3)
Cl2	0.2526 (16)	0.3447 (7)	0.0642 (13)	0.0622 (9)	0.267 (3)
O21	0.120 (2)	0.3833 (9)	0.103 (3)	0.097 (3)	0.267 (3)
O22	0.232 (4)	0.3364 (16)	−0.0645 (12)	0.111 (2)	0.267 (3)
O23	0.4019 (18)	0.3833 (13)	0.104 (2)	0.101 (4)	0.267 (3)
O24	0.261 (2)	0.2702 (7)	0.1209 (13)	0.090 (3)	0.267 (3)
Cl3	0.2227 (13)	0.3347 (8)	0.0565 (11)	0.0622 (9)	0.256 (3)
O31	0.184 (2)	0.4097 (8)	0.090 (3)	0.097 (3)	0.256 (3)
O32	0.261 (3)	0.3320 (18)	−0.0639 (11)	0.111 (2)	0.256 (3)
O33	0.3546 (16)	0.3034 (13)	0.1385 (14)	0.101 (4)	0.256 (3)
O34	0.0812 (17)	0.2883 (10)	0.0635 (16)	0.090 (3)	0.256 (3)
Cl4	0.215 (3)	0.3423 (16)	0.032 (2)	0.0622 (9)	0.061 (3)
O41	0.168 (6)	0.4201 (17)	0.025 (5)	0.097 (3)	0.061 (3)
O42	0.377 (3)	0.332 (3)	0.012 (4)	0.111 (2)	0.061 (3)
O43	0.195 (5)	0.309 (3)	0.147 (3)	0.101 (4)	0.061 (3)
O44	0.107 (5)	0.303 (2)	−0.062 (3)	0.090 (3)	0.061 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0467 (3)	0.0396 (4)	0.0320 (3)	−0.0034 (3)	0.0112 (2)	0.0034 (3)
N1	0.0521 (16)	0.0463 (17)	0.0374 (14)	−0.0063 (13)	0.0116 (12)	0.0021 (12)
N11	0.0504 (15)	0.0400 (16)	0.0376 (14)	−0.0032 (12)	0.0100 (12)	0.0000 (12)
C12	0.0468 (16)	0.044 (2)	0.0352 (15)	−0.0050 (14)	0.0095 (13)	−0.0013 (13)
C13	0.059 (2)	0.064 (3)	0.046 (2)	−0.0069 (19)	0.0209 (16)	−0.0067 (17)
C14	0.061 (2)	0.068 (3)	0.063 (2)	0.004 (2)	0.0243 (19)	−0.014 (2)
C15	0.061 (2)	0.049 (2)	0.065 (2)	0.0080 (18)	0.0099 (18)	−0.0076 (19)
C16	0.055 (2)	0.043 (2)	0.050 (2)	0.0002 (16)	0.0068 (16)	0.0017 (16)
N21	0.0481 (15)	0.0419 (16)	0.0370 (14)	−0.0034 (12)	0.0100 (11)	0.0035 (12)
C22	0.0472 (17)	0.0394 (19)	0.0386 (16)	0.0005 (15)	0.0089 (13)	0.0043 (14)
C23	0.058 (2)	0.045 (2)	0.0506 (19)	−0.0057 (17)	0.0176 (16)	0.0082 (16)
C24	0.060 (2)	0.048 (2)	0.067 (2)	−0.0125 (18)	0.0106 (18)	0.0049 (19)
C25	0.060 (2)	0.050 (2)	0.055 (2)	−0.0109 (17)	0.0029 (16)	−0.0058 (17)
C26	0.056 (2)	0.046 (2)	0.0396 (17)	−0.0057 (16)	0.0065 (14)	−0.0023 (15)
N31	0.0507 (15)	0.0410 (16)	0.0371 (14)	−0.0028 (13)	0.0081 (12)	0.0024 (12)
C32	0.0555 (19)	0.0420 (19)	0.0341 (16)	−0.0018 (15)	0.0061 (14)	0.0024 (14)
C33	0.071 (2)	0.060 (2)	0.0397 (18)	−0.0058 (19)	0.0086 (16)	0.0078 (17)
C34	0.074 (3)	0.068 (3)	0.047 (2)	0.003 (2)	−0.0062 (18)	0.0132 (19)
C35	0.058 (2)	0.059 (2)	0.058 (2)	0.0013 (18)	−0.0022 (17)	0.0021 (18)
C36	0.0514 (19)	0.053 (2)	0.0473 (19)	−0.0037 (17)	0.0094 (15)	0.0013 (17)
Cl1	0.0683 (17)	0.081 (2)	0.0385 (11)	0.0170 (11)	0.0109 (12)	−0.0146 (12)
O11	0.088 (6)	0.072 (5)	0.143 (5)	0.010 (4)	0.058 (5)	−0.036 (6)
O12	0.163 (6)	0.130 (5)	0.0448 (19)	0.013 (5)	0.034 (2)	−0.011 (2)
O13	0.052 (3)	0.163 (15)	0.085 (6)	−0.006 (5)	0.006 (3)	0.020 (9)
O14	0.099 (9)	0.095 (5)	0.075 (5)	−0.001 (6)	0.014 (6)	0.003 (4)
Cl2	0.0683 (17)	0.081 (2)	0.0385 (11)	0.0170 (11)	0.0109 (12)	−0.0146 (12)
O21	0.088 (6)	0.072 (5)	0.143 (5)	0.010 (4)	0.058 (5)	−0.036 (6)
O22	0.163 (6)	0.130 (5)	0.0448 (19)	0.013 (5)	0.034 (2)	−0.011 (2)
O23	0.052 (3)	0.163 (15)	0.085 (6)	−0.006 (5)	0.006 (3)	0.020 (9)
O24	0.099 (9)	0.095 (5)	0.075 (5)	−0.001 (6)	0.014 (6)	0.003 (4)
Cl3	0.0683 (17)	0.081 (2)	0.0385 (11)	0.0170 (11)	0.0109 (12)	−0.0146 (12)
O31	0.088 (6)	0.072 (5)	0.143 (5)	0.010 (4)	0.058 (5)	−0.036 (6)
O32	0.163 (6)	0.130 (5)	0.0448 (19)	0.013 (5)	0.034 (2)	−0.011 (2)
O33	0.052 (3)	0.163 (15)	0.085 (6)	−0.006 (5)	0.006 (3)	0.020 (9)
O34	0.099 (9)	0.095 (5)	0.075 (5)	−0.001 (6)	0.014 (6)	0.003 (4)
Cl4	0.0683 (17)	0.081 (2)	0.0385 (11)	0.0170 (11)	0.0109 (12)	−0.0146 (12)
O41	0.088 (6)	0.072 (5)	0.143 (5)	0.010 (4)	0.058 (5)	−0.036 (6)
O42	0.163 (6)	0.130 (5)	0.0448 (19)	0.013 (5)	0.034 (2)	−0.011 (2)
O43	0.052 (3)	0.163 (15)	0.085 (6)	−0.006 (5)	0.006 (3)	0.020 (9)
O44	0.099 (9)	0.095 (5)	0.075 (5)	−0.001 (6)	0.014 (6)	0.003 (4)

Geometric parameters (Å, º)

Fe1—N21^i	1.970 (3)	C26—H26	0.9300
Fe1—N21	1.970 (3)	N31—C32	1.350 (4)
Fe1—N31^i	1.982 (3)	N31—C36	1.359 (4)
Fe1—N31	1.982 (3)	C32—C33	1.361 (5)
Fe1—N11	1.983 (2)	C33—C34	1.377 (5)
Fe1—N11^i	1.983 (2)	C33—H33	0.9300
N1—C22	1.433 (4)	C34—C35	1.376 (5)
N1—C12	1.434 (4)	C34—H34	0.9300
N1—C32	1.442 (4)	C35—C36	1.365 (5)
N11—C16	1.342 (4)	C35—H35	0.9300
N11—C12	1.344 (4)	C36—H36	0.9300
C12—C13	1.374 (4)	Cl1—O12	1.413 (4)
C13—C14	1.378 (5)	Cl1—O11	1.416 (5)
C13—H13	0.9300	Cl1—O13	1.423 (6)
C14—C15	1.380 (5)	Cl1—O14	1.443 (6)
C14—H14	0.9300	Cl2—O22	1.413 (5)
C15—C16	1.371 (5)	Cl2—O21	1.414 (5)
C15—H15	0.9300	Cl2—O23	1.424 (7)
C16—H16	0.9300	Cl2—O24	1.441 (7)
N21—C26	1.344 (4)	Cl3—O32	1.414 (5)
N21—C22	1.346 (4)	Cl3—O31	1.414 (5)
C22—C23	1.385 (4)	Cl3—O33	1.423 (7)
C23—C24	1.367 (5)	Cl3—O34	1.442 (7)
C23—H23	0.9300	Cl4—O42	1.413 (6)
C24—C25	1.383 (5)	Cl4—O41	1.415 (6)
C24—H24	0.9300	Cl4—O43	1.423 (7)
C25—C26	1.371 (5)	Cl4—O44	1.442 (7)
C25—H25	0.9300
N21^i—Fe1—N21	180.0	C26—C25—C24	119.0 (3)
N21^i—Fe1—N31^i	87.88 (11)	C26—C25—H25	120.5
N21—Fe1—N31^i	92.12 (11)	C24—C25—H25	120.5
N21^i—Fe1—N31	92.11 (11)	N21—C26—C25	122.6 (3)
N21—Fe1—N31	87.89 (11)	N21—C26—H26	118.7
N31^i—Fe1—N31	180.0	C25—C26—H26	118.7
N21^i—Fe1—N11	91.67 (10)	C32—N31—C36	116.4 (3)
N21—Fe1—N11	88.33 (10)	C32—N31—Fe1	117.5 (2)
N31^i—Fe1—N11	91.89 (11)	C36—N31—Fe1	126.1 (2)
N31—Fe1—N11	88.11 (11)	N31—C32—C33	123.7 (3)
N21^i—Fe1—N11^i	88.33 (10)	N31—C32—N1	116.1 (3)
N21—Fe1—N11^i	91.66 (10)	C33—C32—N1	120.2 (3)
N31^i—Fe1—N11^i	88.11 (10)	C32—C33—C34	118.9 (3)
N31—Fe1—N11^i	91.89 (11)	C32—C33—H33	120.6
N11—Fe1—N11^i	180.0	C34—C33—H33	120.6
C22—N1—C12	112.0 (3)	C35—C34—C33	118.7 (4)
C22—N1—C32	111.1 (2)	C35—C34—H34	120.7
C12—N1—C32	111.4 (3)	C33—C34—H34	120.7
C16—N11—C12	117.3 (3)	C36—C35—C34	119.7 (4)
C16—N11—Fe1	125.4 (2)	C36—C35—H35	120.2
C12—N11—Fe1	117.3 (2)	C34—C35—H35	120.2
N11—C12—C13	123.4 (3)	N31—C36—C35	122.6 (3)
N11—C12—N1	116.7 (2)	N31—C36—H36	118.7
C13—C12—N1	119.9 (3)	C35—C36—H36	118.7
C12—C13—C14	118.4 (3)	O12—Cl1—O11	111.7 (5)
C12—C13—H13	120.8	O12—Cl1—O13	109.2 (5)
C14—C13—H13	120.8	O11—Cl1—O13	111.7 (5)
C13—C14—C15	118.9 (3)	O12—Cl1—O14	109.4 (5)
C13—C14—H14	120.5	O11—Cl1—O14	106.2 (5)
C15—C14—H14	120.5	O13—Cl1—O14	108.5 (6)
C16—C15—C14	119.3 (4)	O22—Cl2—O21	111.9 (6)
C16—C15—H15	120.4	O22—Cl2—O23	109.1 (6)
C14—C15—H15	120.4	O21—Cl2—O23	111.3 (6)
N11—C16—C15	122.7 (3)	O22—Cl2—O24	109.6 (6)
N11—C16—H16	118.7	O21—Cl2—O24	106.6 (6)
C15—C16—H16	118.7	O23—Cl2—O24	108.2 (7)
C26—N21—C22	117.6 (3)	O32—Cl3—O31	111.8 (6)
C26—N21—Fe1	125.2 (2)	O32—Cl3—O33	108.9 (6)
C22—N21—Fe1	117.2 (2)	O31—Cl3—O33	111.8 (7)
N21—C22—C23	122.8 (3)	O32—Cl3—O34	109.5 (6)
N21—C22—N1	117.0 (3)	O31—Cl3—O34	106.7 (6)
C23—C22—N1	120.2 (3)	O33—Cl3—O34	107.9 (7)
C24—C23—C22	118.5 (3)	O42—Cl4—O41	111.8 (7)
C24—C23—H23	120.7	O42—Cl4—O43	109.2 (7)
C22—C23—H23	120.7	O41—Cl4—O43	111.8 (8)
C23—C24—C25	119.4 (3)	O42—Cl4—O44	109.4 (7)
C23—C24—H24	120.3	O41—Cl4—O44	106.4 (7)
C25—C24—H24	120.3	O43—Cl4—O44	108.1 (8)
C16—N11—C12—C13	−0.9 (5)	N21—C22—C23—C24	0.5 (5)
Fe1—N11—C12—C13	178.8 (3)	N1—C22—C23—C24	−178.5 (3)
C16—N11—C12—N1	179.7 (3)	C22—C23—C24—C25	−0.1 (5)
Fe1—N11—C12—N1	−0.7 (4)	C23—C24—C25—C26	−0.7 (6)
C22—N1—C12—N11	−61.6 (3)	C22—N21—C26—C25	−0.7 (5)
C32—N1—C12—N11	63.6 (3)	Fe1—N21—C26—C25	178.2 (3)
C22—N1—C12—C13	118.9 (3)	C24—C25—C26—N21	1.1 (5)
C32—N1—C12—C13	−115.9 (3)	C36—N31—C32—C33	0.3 (5)
N11—C12—C13—C14	1.7 (6)	Fe1—N31—C32—C33	179.5 (3)
N1—C12—C13—C14	−178.9 (3)	C36—N31—C32—N1	−178.9 (3)
C12—C13—C14—C15	−1.2 (6)	Fe1—N31—C32—N1	0.2 (4)
C13—C14—C15—C16	−0.1 (6)	C22—N1—C32—N31	62.5 (4)
C12—N11—C16—C15	−0.5 (5)	C12—N1—C32—N31	−63.2 (3)
Fe1—N11—C16—C15	180.0 (3)	C22—N1—C32—C33	−116.7 (3)
C14—C15—C16—N11	0.9 (6)	C12—N1—C32—C33	117.5 (3)
C26—N21—C22—C23	−0.1 (5)	N31—C32—C33—C34	−0.9 (6)
Fe1—N21—C22—C23	−179.1 (3)	N1—C32—C33—C34	178.3 (3)
C26—N21—C22—N1	178.9 (3)	C32—C33—C34—C35	1.0 (6)
Fe1—N21—C22—N1	−0.1 (4)	C33—C34—C35—C36	−0.6 (6)
C12—N1—C22—N21	62.3 (3)	C32—N31—C36—C35	0.1 (5)
C32—N1—C22—N21	−63.0 (4)	Fe1—N31—C36—C35	−179.0 (3)
C12—N1—C22—C23	−118.6 (3)	C34—C35—C36—N31	0.1 (6)
C32—N1—C22—C23	116.0 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O21^ii	0.93	2.38	3.11 (2)	136
C14—H14···O34^ii	0.93	2.54	3.470 (17)	173
C15—H15···O22^iii	0.93	2.44	3.24 (3)	143
C15—H15···O32^iii	0.93	2.31	3.14 (3)	147
C23—H23···O12^iv	0.93	2.58	3.412 (10)	150
C23—H23···O22^iv	0.93	2.52	3.357 (14)	150
C23—H23···O32^iv	0.93	2.53	3.347 (12)	147
C24—H24···O13^v	0.93	2.60	3.496 (12)	163
C24—H24···O33^v	0.93	2.53	3.334 (17)	145
C24—H24···O42^v	0.93	2.21	3.10 (4)	161
C26—H26···O13	0.93	2.51	3.375 (12)	155
C26—H26···O33	0.93	2.56	3.289 (17)	135
C33—H33···O42^iv	0.93	2.30	3.21 (4)	164

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

Bis(tri-2-pyridylamine)nickel(II) bis(perchlorate) (III)

Crystal data

[Ni(C15H12N4)2](ClO4)2	F(000) = 772
Mr = 754.18	Dx = 1.549 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.360 (4) Å	Cell parameters from 2895 reflections
b = 17.570 (8) Å	θ = 2.3–28.4°
c = 11.165 (5) Å	µ = 0.83 mm^−1
β = 99.542 (5)°	T = 296 K
V = 1617.3 (13) Å^3	Block, purple
Z = 2	0.22 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer	3895 independent reflections
Radiation source: fine focus sealed tube	2611 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
φ and ω scans	θmax = 28.4°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→10
Tmin = 0.861, Tmax = 0.920	k = −22→22
14055 measured reflections	l = −14→14

Refinement

Refinement on F^2	61 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.109	w = 1/[σ^2(Fo^2) + (0.0471P)^2 + 0.3274P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
3895 reflections	Δρmax = 0.34 e Å^−3
272 parameters	Δρmin = −0.36 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ni1	0.5000	0.5000	0.5000	0.03796 (15)
N1	0.3741 (3)	0.44195 (11)	0.71780 (17)	0.0413 (5)
N11	0.3603 (3)	0.55818 (11)	0.60850 (17)	0.0425 (5)
C12	0.3193 (3)	0.51938 (14)	0.7020 (2)	0.0402 (6)
C13	0.2283 (3)	0.55033 (16)	0.7809 (2)	0.0523 (7)
H13	0.2027	0.5220	0.8455	0.063*
C14	0.1757 (4)	0.62410 (17)	0.7626 (3)	0.0618 (8)
H14	0.1120	0.6463	0.8139	0.074*
C15	0.2179 (3)	0.66449 (16)	0.6685 (3)	0.0571 (7)
H15	0.1843	0.7147	0.6555	0.068*
C16	0.3101 (3)	0.63049 (15)	0.5931 (2)	0.0491 (6)
H16	0.3388	0.6585	0.5292	0.059*
N21	0.3472 (3)	0.40791 (11)	0.50938 (17)	0.0421 (5)
C22	0.3077 (3)	0.39311 (13)	0.6185 (2)	0.0398 (6)
C23	0.2089 (3)	0.33333 (14)	0.6379 (2)	0.0487 (6)
H23	0.1817	0.3248	0.7143	0.058*
C24	0.1512 (4)	0.28645 (16)	0.5418 (3)	0.0586 (7)
H24	0.0852	0.2453	0.5526	0.070*
C25	0.1917 (3)	0.30088 (15)	0.4301 (3)	0.0544 (7)
H25	0.1539	0.2697	0.3642	0.065*
C26	0.2887 (3)	0.36191 (15)	0.4173 (2)	0.0494 (6)
H26	0.3151	0.3718	0.3411	0.059*
N31	0.6341 (3)	0.45832 (11)	0.66281 (17)	0.0421 (5)
C32	0.5477 (3)	0.43591 (13)	0.7471 (2)	0.0410 (6)
C33	0.6174 (4)	0.40688 (16)	0.8578 (2)	0.0547 (7)
H33	0.5540	0.3925	0.9150	0.066*
C34	0.7836 (4)	0.39971 (17)	0.8818 (3)	0.0642 (8)
H34	0.8342	0.3799	0.9557	0.077*
C35	0.8739 (4)	0.42181 (16)	0.7965 (3)	0.0573 (7)
H35	0.9863	0.4170	0.8111	0.069*
C36	0.7953 (3)	0.45125 (16)	0.6888 (2)	0.0531 (7)
H36	0.8570	0.4670	0.6313	0.064*
Cl1	0.2327 (9)	0.3463 (5)	0.0711 (7)	0.0603 (7)	0.424 (3)
O11	0.1382 (11)	0.4106 (4)	0.0898 (16)	0.104 (2)	0.424 (3)
O12	0.238 (2)	0.3337 (11)	−0.0522 (7)	0.1217 (17)	0.424 (3)
O13	0.3919 (9)	0.3541 (7)	0.1374 (10)	0.104 (3)	0.424 (3)
O14	0.1568 (12)	0.2813 (4)	0.1163 (8)	0.095 (2)	0.424 (3)
Cl2	0.2562 (14)	0.3409 (6)	0.0680 (11)	0.0603 (7)	0.280 (3)
O21	0.1225 (17)	0.3830 (7)	0.095 (2)	0.104 (2)	0.280 (3)
O22	0.246 (4)	0.3265 (14)	−0.0566 (11)	0.1217 (17)	0.280 (3)
O23	0.4031 (15)	0.3795 (11)	0.113 (2)	0.104 (3)	0.280 (3)
O24	0.2573 (17)	0.2693 (6)	0.1296 (11)	0.095 (2)	0.280 (3)
Cl3	0.2238 (12)	0.3356 (7)	0.0680 (11)	0.0603 (7)	0.244 (3)
O31	0.190 (2)	0.4077 (7)	0.114 (3)	0.104 (2)	0.244 (3)
O32	0.260 (3)	0.340 (2)	−0.0501 (11)	0.1217 (17)	0.244 (3)
O33	0.3537 (13)	0.3010 (10)	0.1470 (11)	0.104 (3)	0.244 (3)
O34	0.0822 (14)	0.2890 (8)	0.0645 (13)	0.095 (2)	0.244 (3)
Cl4	0.196 (2)	0.3332 (12)	0.0342 (16)	0.0603 (7)	0.052 (2)
O41	0.177 (5)	0.4126 (12)	0.016 (4)	0.104 (2)	0.052 (2)
O42	0.356 (3)	0.309 (2)	0.034 (3)	0.1217 (17)	0.052 (2)
O43	0.143 (5)	0.312 (3)	0.143 (2)	0.104 (3)	0.052 (2)
O44	0.094 (4)	0.296 (2)	−0.065 (3)	0.095 (2)	0.052 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0482 (3)	0.0388 (2)	0.0288 (2)	−0.0034 (2)	0.01177 (18)	0.00442 (18)
N1	0.0527 (13)	0.0397 (11)	0.0330 (11)	−0.0033 (10)	0.0114 (9)	0.0027 (9)
N11	0.0527 (13)	0.0418 (11)	0.0348 (11)	0.0006 (9)	0.0122 (9)	0.0028 (9)
C12	0.0432 (14)	0.0467 (14)	0.0318 (12)	−0.0051 (11)	0.0095 (11)	−0.0012 (10)
C13	0.0587 (18)	0.0594 (17)	0.0427 (15)	−0.0064 (14)	0.0201 (13)	−0.0062 (13)
C14	0.0608 (19)	0.0673 (19)	0.0622 (19)	0.0041 (15)	0.0244 (15)	−0.0156 (16)
C15	0.0600 (18)	0.0490 (16)	0.0617 (18)	0.0085 (14)	0.0088 (15)	−0.0076 (14)
C16	0.0579 (17)	0.0438 (14)	0.0459 (15)	0.0018 (12)	0.0096 (13)	0.0041 (12)
N21	0.0543 (13)	0.0413 (11)	0.0309 (10)	−0.0060 (10)	0.0080 (9)	0.0037 (9)
C22	0.0456 (14)	0.0384 (13)	0.0359 (13)	−0.0011 (11)	0.0085 (11)	0.0067 (10)
C23	0.0529 (16)	0.0467 (14)	0.0485 (15)	−0.0042 (12)	0.0143 (13)	0.0101 (12)
C24	0.0600 (18)	0.0470 (15)	0.0686 (19)	−0.0157 (13)	0.0097 (15)	0.0025 (14)
C25	0.0588 (18)	0.0474 (15)	0.0547 (17)	−0.0076 (13)	0.0026 (14)	−0.0058 (13)
C26	0.0599 (18)	0.0515 (15)	0.0371 (14)	−0.0048 (13)	0.0085 (12)	−0.0006 (12)
N31	0.0477 (13)	0.0450 (12)	0.0336 (11)	−0.0035 (10)	0.0070 (9)	0.0046 (9)
C32	0.0534 (16)	0.0385 (13)	0.0315 (12)	−0.0019 (11)	0.0085 (11)	0.0034 (10)
C33	0.069 (2)	0.0583 (17)	0.0361 (14)	−0.0048 (15)	0.0079 (13)	0.0108 (12)
C34	0.072 (2)	0.070 (2)	0.0447 (16)	0.0036 (17)	−0.0072 (15)	0.0123 (14)
C35	0.0529 (18)	0.0607 (18)	0.0548 (18)	0.0014 (14)	−0.0015 (14)	0.0024 (14)
C36	0.0531 (18)	0.0570 (17)	0.0493 (16)	−0.0028 (14)	0.0087 (13)	0.0060 (13)
Cl1	0.0585 (17)	0.0840 (14)	0.0389 (6)	0.0191 (10)	0.0099 (9)	−0.0132 (8)
O11	0.081 (5)	0.076 (4)	0.156 (6)	0.012 (3)	0.025 (5)	−0.052 (5)
O12	0.184 (4)	0.142 (4)	0.0458 (16)	−0.004 (3)	0.039 (2)	−0.019 (2)
O13	0.053 (3)	0.177 (10)	0.080 (5)	−0.015 (4)	0.003 (3)	0.010 (6)
O14	0.104 (8)	0.099 (4)	0.086 (5)	0.015 (5)	0.024 (6)	0.015 (3)
Cl2	0.0585 (17)	0.0840 (14)	0.0389 (6)	0.0191 (10)	0.0099 (9)	−0.0132 (8)
O21	0.081 (5)	0.076 (4)	0.156 (6)	0.012 (3)	0.025 (5)	−0.052 (5)
O22	0.184 (4)	0.142 (4)	0.0458 (16)	−0.004 (3)	0.039 (2)	−0.019 (2)
O23	0.053 (3)	0.177 (10)	0.080 (5)	−0.015 (4)	0.003 (3)	0.010 (6)
O24	0.104 (8)	0.099 (4)	0.086 (5)	0.015 (5)	0.024 (6)	0.015 (3)
Cl3	0.0585 (17)	0.0840 (14)	0.0389 (6)	0.0191 (10)	0.0099 (9)	−0.0132 (8)
O31	0.081 (5)	0.076 (4)	0.156 (6)	0.012 (3)	0.025 (5)	−0.052 (5)
O32	0.184 (4)	0.142 (4)	0.0458 (16)	−0.004 (3)	0.039 (2)	−0.019 (2)
O33	0.053 (3)	0.177 (10)	0.080 (5)	−0.015 (4)	0.003 (3)	0.010 (6)
O34	0.104 (8)	0.099 (4)	0.086 (5)	0.015 (5)	0.024 (6)	0.015 (3)
Cl4	0.0585 (17)	0.0840 (14)	0.0389 (6)	0.0191 (10)	0.0099 (9)	−0.0132 (8)
O41	0.081 (5)	0.076 (4)	0.156 (6)	0.012 (3)	0.025 (5)	−0.052 (5)
O42	0.184 (4)	0.142 (4)	0.0458 (16)	−0.004 (3)	0.039 (2)	−0.019 (2)
O43	0.053 (3)	0.177 (10)	0.080 (5)	−0.015 (4)	0.003 (3)	0.010 (6)
O44	0.104 (8)	0.099 (4)	0.086 (5)	0.015 (5)	0.024 (6)	0.015 (3)

Geometric parameters (Å, º)

Ni1—N21	2.075 (2)	C26—H26	0.9300
Ni1—N21^i	2.075 (2)	N31—C36	1.336 (3)
Ni1—N11	2.084 (2)	N31—C32	1.337 (3)
Ni1—N11^i	2.085 (2)	C32—C33	1.374 (3)
Ni1—N31	2.103 (2)	C33—C34	1.377 (4)
Ni1—N31^i	2.103 (2)	C33—H33	0.9300
N1—C12	1.437 (3)	C34—C35	1.365 (4)
N1—C32	1.438 (3)	C34—H34	0.9300
N1—C22	1.439 (3)	C35—C36	1.373 (4)
N11—C12	1.338 (3)	C35—H35	0.9300
N11—C16	1.340 (3)	C36—H36	0.9300
C12—C13	1.369 (3)	Cl1—O12	1.402 (4)
C13—C14	1.373 (4)	Cl1—O11	1.415 (4)
C13—H13	0.9300	Cl1—O13	1.419 (5)
C14—C15	1.362 (4)	Cl1—O14	1.438 (5)
C14—H14	0.9300	Cl2—O22	1.402 (4)
C15—C16	1.369 (4)	Cl2—O21	1.412 (5)
C15—H15	0.9300	Cl2—O23	1.419 (5)
C16—H16	0.9300	Cl2—O24	1.434 (6)
N21—C26	1.335 (3)	Cl3—O32	1.402 (4)
N21—C22	1.339 (3)	Cl3—O31	1.413 (5)
C22—C23	1.376 (3)	Cl3—O33	1.418 (6)
C23—C24	1.375 (4)	Cl3—O34	1.434 (6)
C23—H23	0.9300	Cl4—O42	1.401 (5)
C24—C25	1.368 (4)	Cl4—O41	1.415 (5)
C24—H24	0.9300	Cl4—O43	1.417 (6)
C25—C26	1.366 (4)	Cl4—O44	1.435 (6)
C25—H25	0.9300
N21—Ni1—N21^i	180.0	C26—C25—C24	118.8 (3)
N21—Ni1—N11	86.80 (8)	C26—C25—H25	120.6
N21^i—Ni1—N11	93.20 (8)	C24—C25—H25	120.6
N21—Ni1—N11^i	93.20 (8)	N21—C26—C25	122.8 (2)
N21^i—Ni1—N11^i	86.80 (8)	N21—C26—H26	118.6
N11—Ni1—N11^i	180.0	C25—C26—H26	118.6
N21—Ni1—N31	85.94 (8)	C36—N31—C32	117.5 (2)
N21^i—Ni1—N31	94.06 (8)	C36—N31—Ni1	126.46 (17)
N11—Ni1—N31	86.46 (8)	C32—N31—Ni1	116.00 (17)
N11^i—Ni1—N31	93.54 (8)	N31—C32—C33	123.0 (3)
N21—Ni1—N31^i	94.06 (8)	N31—C32—N1	117.4 (2)
N21^i—Ni1—N31^i	85.94 (8)	C33—C32—N1	119.5 (2)
N11—Ni1—N31^i	93.54 (8)	C32—C33—C34	118.2 (3)
N11^i—Ni1—N31^i	86.46 (8)	C32—C33—H33	120.9
N31—Ni1—N31^i	180.0	C34—C33—H33	120.9
C12—N1—C32	112.76 (18)	C35—C34—C33	119.7 (3)
C12—N1—C22	113.31 (19)	C35—C34—H34	120.1
C32—N1—C22	112.13 (19)	C33—C34—H34	120.1
C12—N11—C16	117.9 (2)	C34—C35—C36	118.5 (3)
C12—N11—Ni1	116.37 (16)	C34—C35—H35	120.7
C16—N11—Ni1	125.75 (17)	C36—C35—H35	120.7
N11—C12—C13	122.8 (2)	N31—C36—C35	123.0 (3)
N11—C12—N1	117.4 (2)	N31—C36—H36	118.5
C13—C12—N1	119.8 (2)	C35—C36—H36	118.5
C12—C13—C14	118.5 (2)	O12—Cl1—O11	112.3 (4)
C12—C13—H13	120.7	O12—Cl1—O13	110.3 (5)
C14—C13—H13	120.7	O11—Cl1—O13	110.1 (5)
C15—C14—C13	119.3 (3)	O12—Cl1—O14	107.9 (5)
C15—C14—H14	120.4	O11—Cl1—O14	107.1 (4)
C13—C14—H14	120.4	O13—Cl1—O14	108.9 (5)
C14—C15—C16	119.4 (3)	O22—Cl2—O21	112.5 (5)
C14—C15—H15	120.3	O22—Cl2—O23	110.1 (6)
C16—C15—H15	120.3	O21—Cl2—O23	110.1 (6)
N11—C16—C15	122.1 (2)	O22—Cl2—O24	108.2 (6)
N11—C16—H16	118.9	O21—Cl2—O24	107.5 (6)
C15—C16—H16	118.9	O23—Cl2—O24	108.3 (6)
C26—N21—C22	118.0 (2)	O32—Cl3—O31	112.3 (6)
C26—N21—Ni1	125.66 (17)	O32—Cl3—O33	110.3 (6)
C22—N21—Ni1	116.35 (16)	O31—Cl3—O33	109.7 (6)
N21—C22—C23	122.5 (2)	O32—Cl3—O34	108.1 (6)
N21—C22—N1	117.6 (2)	O31—Cl3—O34	107.9 (6)
C23—C22—N1	119.9 (2)	O33—Cl3—O34	108.5 (6)
C24—C23—C22	118.4 (2)	O42—Cl4—O41	112.3 (7)
C24—C23—H23	120.8	O42—Cl4—O43	110.8 (7)
C22—C23—H23	120.8	O41—Cl4—O43	110.0 (7)
C25—C24—C23	119.5 (2)	O42—Cl4—O44	108.2 (7)
C25—C24—H24	120.3	O41—Cl4—O44	107.2 (7)
C23—C24—H24	120.3	O43—Cl4—O44	108.2 (7)
C16—N11—C12—C13	0.4 (4)	N21—C22—C23—C24	1.2 (4)
Ni1—N11—C12—C13	179.8 (2)	N1—C22—C23—C24	−178.2 (2)
C16—N11—C12—N1	−179.9 (2)	C22—C23—C24—C25	−0.7 (4)
Ni1—N11—C12—N1	−0.4 (3)	C23—C24—C25—C26	−0.1 (4)
C32—N1—C12—N11	65.2 (3)	C22—N21—C26—C25	−0.2 (4)
C22—N1—C12—N11	−63.5 (3)	Ni1—N21—C26—C25	178.2 (2)
C32—N1—C12—C13	−115.0 (3)	C24—C25—C26—N21	0.6 (4)
C22—N1—C12—C13	116.2 (3)	C36—N31—C32—C33	0.4 (4)
N11—C12—C13—C14	0.6 (4)	Ni1—N31—C32—C33	179.5 (2)
N1—C12—C13—C14	−179.1 (2)	C36—N31—C32—N1	−178.6 (2)
C12—C13—C14—C15	−1.2 (4)	Ni1—N31—C32—N1	0.5 (3)
C13—C14—C15—C16	0.8 (5)	C12—N1—C32—N31	−65.0 (3)
C12—N11—C16—C15	−0.9 (4)	C22—N1—C32—N31	64.3 (3)
Ni1—N11—C16—C15	179.8 (2)	C12—N1—C32—C33	115.9 (2)
C14—C15—C16—N11	0.3 (4)	C22—N1—C32—C33	−114.8 (2)
C26—N21—C22—C23	−0.7 (4)	N31—C32—C33—C34	−0.9 (4)
Ni1—N21—C22—C23	−179.29 (19)	N1—C32—C33—C34	178.1 (2)
C26—N21—C22—N1	178.7 (2)	C32—C33—C34—C35	0.5 (4)
Ni1—N21—C22—N1	0.1 (3)	C33—C34—C35—C36	0.4 (5)
C12—N1—C22—N21	63.9 (3)	C32—N31—C36—C35	0.5 (4)
C32—N1—C22—N21	−65.1 (3)	Ni1—N31—C36—C35	−178.5 (2)
C12—N1—C22—C23	−116.7 (2)	C34—C35—C36—N31	−1.0 (4)
C32—N1—C22—C23	114.3 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O21^ii	0.93	2.41	3.174 (17)	139
C14—H14···O34^ii	0.93	2.55	3.477 (14)	174
C14—H14···O43^ii	0.93	2.38	3.23 (4)	151
C15—H15···O12^iii	0.93	2.52	3.289 (18)	140
C15—H15···O22^iii	0.93	2.37	3.14 (3)	140
C15—H15···O32^iii	0.93	2.57	3.37 (3)	144
C23—H23···O12^iv	0.93	2.58	3.428 (8)	152
C23—H23···O22^iv	0.93	2.53	3.376 (13)	152
C24—H24···O33^v	0.93	2.49	3.301 (13)	146
C24—H24···O42^v	0.93	2.12	2.97 (3)	152
C26—H26···O13	0.93	2.48	3.380 (11)	162
C26—H26···O33	0.93	2.57	3.331 (13)	140

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