Racemic cis-bis­[bis­(pyrimidin-2-yl)amine-κN]bis(dicyanamido-κN¹)iron(II) dihydrate: synthesis, crystal structure and Hirshfeld surface analysis

The solvothermal synthesis, crystal structure and Hirshfeld surface analysis of a new iron(II) complex containing dicyanamido and di(pyrimidin-2-yl)amine ligands are reported

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 170 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.067
• wR factor = 0.157
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.54 Report
PLAT220_ALERT_2_C NonSolvent   Resd 1  N   Ueq(max)/Ueq(min) Range        3.4 Ratio
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        N53 Check
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        N63 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C62 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C64 Check
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00613 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.888 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          7 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          8 Note
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       5.93 Why ?
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          4 Report
PLAT300_ALERT_4_G Atom Site Occupancy of H72        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H73        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H82        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H83        Constrained at        0.5 Check
PLAT794_ALERT_5_G Tentative Bond Valency for Fe1       (II)      .       2.05 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         12 Note
PLAT870_ALERT_4_G ALERTS Related to Twinning Effects Suppressed ..          ! Info
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         23 Note
PLAT931_ALERT_5_G CIFcalcFCF  Twin Law         [ 1 0 0] Est.d BASF       0.19 Check
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          1 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        1.0 Low

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   9 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

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

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2020) and Mercury (Macrae et al., 2020); software used to prepare material for publication: PLATON (Spek, 2020) and publCIF (Westrip, 2010).

cis-Bis[bis(pyrimidin-2-yl)amine-κN]bis(dicyanamido-κN¹)iron(II) dihydrate

Crystal data

[Fe(C2N3)2(C8H7N5)2]·2H2O	Z = 2
Mr = 570.35	F(000) = 584
Triclinic, P1	Dx = 1.549 Mg m^−3
a = 8.1960 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.4671 (11) Å	Cell parameters from 6057 reflections
c = 14.7926 (14) Å	θ = 2.5–28.4°
α = 105.254 (4)°	µ = 0.67 mm^−1
β = 92.903 (3)°	T = 170 K
γ = 90.356 (4)°	Needle, yellow
V = 1222.5 (2) Å^3	0.25 × 0.20 × 0.15 mm

Data collection

Rigaku Oxford Diffraction SuperNova, single source at offset/far, Eos diffractometer	6056 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	5802 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.037
ω scans	θmax = 28.4°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −10→10
Tmin = 0.623, Tmax = 0.906	k = −13→13
6056 measured reflections	l = −19→19

Refinement

Refinement on F^2	Primary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.067	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.157	w = 1/[σ^2(Fo^2) + 5.9338P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
6056 reflections	Δρmax = 1.47 e Å^−3
377 parameters	Δρmin = −0.58 e Å^−3
12 restraints

Special details

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

Refinement. Refined as a 2-component twin.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Fe1	0.28878 (7)	0.59497 (5)	0.32111 (3)	0.01841 (13)
N1	0.5194 (4)	0.5167 (3)	0.1355 (2)	0.0228 (7)
H1	0.547 (6)	0.478 (5)	0.081 (3)	0.027*
N11	0.5331 (4)	0.5184 (3)	0.2957 (2)	0.0219 (6)
C12	0.5903 (5)	0.4757 (4)	0.2095 (3)	0.0215 (7)
N13	0.7127 (4)	0.3911 (3)	0.1857 (2)	0.0278 (7)
C14	0.7890 (5)	0.3528 (4)	0.2551 (3)	0.0306 (9)
H14	0.8742	0.2908	0.2405	0.037*
C15	0.7495 (5)	0.3994 (4)	0.3485 (3)	0.0306 (9)
H15	0.8100	0.3757	0.3979	0.037*
C16	0.6190 (5)	0.4812 (4)	0.3648 (3)	0.0286 (8)
H16	0.5870	0.5134	0.4275	0.034*
N21	0.3681 (4)	0.6974 (3)	0.2158 (2)	0.0202 (6)
C22	0.4278 (5)	0.6255 (3)	0.1357 (3)	0.0196 (7)
N23	0.4029 (4)	0.6478 (3)	0.0507 (2)	0.0262 (7)
C24	0.3213 (6)	0.7560 (4)	0.0474 (3)	0.0312 (9)
H24	0.2981	0.7733	−0.0118	0.037*
C25	0.2687 (6)	0.8452 (4)	0.1280 (3)	0.0290 (8)
H25	0.2186	0.9259	0.1257	0.035*
C26	0.2932 (5)	0.8103 (4)	0.2110 (3)	0.0241 (8)
H26	0.2561	0.8676	0.2669	0.029*
N3	0.0205 (4)	0.5704 (3)	0.1378 (2)	0.0221 (6)
H3	−0.026 (6)	0.586 (5)	0.086 (3)	0.027*
N31	0.0422 (4)	0.6630 (3)	0.3022 (2)	0.0233 (7)
C32	−0.0328 (5)	0.6564 (4)	0.2185 (3)	0.0208 (7)
N33	−0.1591 (4)	0.7287 (3)	0.2022 (2)	0.0278 (7)
C34	−0.2224 (5)	0.8094 (4)	0.2778 (3)	0.0309 (9)
H34	−0.3109	0.8639	0.2692	0.037*
C35	−0.1622 (6)	0.8155 (5)	0.3684 (3)	0.0344 (10)
H35	−0.2121	0.8683	0.4218	0.041*
C36	−0.0275 (5)	0.7417 (4)	0.3772 (3)	0.0294 (9)
H36	0.0184	0.7461	0.4382	0.035*
N41	0.1913 (4)	0.4328 (3)	0.2006 (2)	0.0206 (6)
C42	0.1115 (5)	0.4589 (4)	0.1268 (2)	0.0198 (7)
N43	0.1116 (4)	0.3831 (3)	0.0374 (2)	0.0253 (7)
C44	0.1914 (6)	0.2702 (4)	0.0234 (3)	0.0289 (9)
H44	0.1978	0.2163	−0.0389	0.035*
C45	0.2662 (5)	0.2281 (4)	0.0969 (3)	0.0267 (8)
H45	0.3150	0.1437	0.0868	0.032*
C46	0.2661 (5)	0.3141 (4)	0.1844 (3)	0.0211 (7)
H46	0.3202	0.2900	0.2356	0.025*
N51	0.2329 (5)	0.4644 (4)	0.4057 (2)	0.0326 (8)
C52	0.1779 (5)	0.3624 (4)	0.4059 (3)	0.0276 (8)
N53	0.1117 (7)	0.2525 (4)	0.4132 (3)	0.0489 (12)
C54	0.0792 (6)	0.1549 (5)	0.3370 (3)	0.0356 (10)
N55	0.0436 (6)	0.0672 (4)	0.2730 (3)	0.0485 (11)
N61	0.3620 (5)	0.7507 (4)	0.4355 (2)	0.0338 (8)
C62	0.4141 (6)	0.8241 (4)	0.5033 (3)	0.0326 (9)
N63	0.4727 (9)	0.9156 (5)	0.5750 (3)	0.0694 (19)
C64	0.4855 (6)	0.8965 (4)	0.6591 (3)	0.0325 (9)
N65	0.5029 (6)	0.8940 (4)	0.7348 (3)	0.0404 (9)
O71	−0.0803 (5)	0.0590 (4)	0.0801 (3)	0.0548 (10)
H71	−0.037 (8)	0.059 (7)	0.134 (3)	0.082*
H72	−0.177 (6)	0.025 (11)	0.079 (6)	0.082*	0.5
H73	−0.028 (11)	0.002 (9)	0.041 (4)	0.082*	0.5
O81	0.4001 (5)	0.9987 (4)	0.9222 (2)	0.0492 (10)
H81	0.439 (8)	0.981 (7)	0.868 (2)	0.074*
H82	0.309 (7)	0.955 (9)	0.915 (6)	0.074*	0.5
H83	0.464 (9)	0.960 (9)	0.954 (5)	0.074*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0221 (3)	0.0223 (3)	0.0094 (2)	0.0008 (2)	−0.00059 (18)	0.00175 (18)
N1	0.0282 (17)	0.0237 (16)	0.0160 (14)	0.0051 (13)	0.0043 (12)	0.0041 (12)
N11	0.0203 (15)	0.0290 (16)	0.0161 (14)	−0.0020 (12)	−0.0004 (11)	0.0055 (12)
C12	0.0218 (17)	0.0214 (17)	0.0211 (17)	0.0000 (14)	0.0009 (14)	0.0051 (14)
N13	0.0311 (18)	0.0271 (17)	0.0277 (17)	0.0068 (14)	0.0048 (14)	0.0108 (14)
C14	0.027 (2)	0.032 (2)	0.036 (2)	0.0074 (17)	0.0041 (17)	0.0158 (18)
C15	0.027 (2)	0.037 (2)	0.031 (2)	0.0004 (17)	−0.0056 (16)	0.0145 (18)
C16	0.030 (2)	0.038 (2)	0.0184 (17)	−0.0032 (17)	−0.0054 (15)	0.0086 (16)
N21	0.0252 (16)	0.0181 (14)	0.0165 (14)	−0.0010 (12)	0.0024 (12)	0.0027 (11)
C22	0.0225 (17)	0.0163 (16)	0.0199 (16)	−0.0033 (13)	0.0034 (13)	0.0044 (13)
N23	0.0364 (19)	0.0249 (16)	0.0193 (15)	0.0050 (14)	0.0054 (13)	0.0088 (13)
C24	0.046 (3)	0.026 (2)	0.026 (2)	0.0066 (18)	0.0070 (18)	0.0135 (16)
C25	0.040 (2)	0.0185 (17)	0.032 (2)	0.0050 (16)	0.0084 (18)	0.0099 (15)
C26	0.030 (2)	0.0152 (16)	0.0243 (18)	−0.0006 (14)	0.0052 (15)	0.0005 (14)
N3	0.0288 (17)	0.0225 (15)	0.0128 (13)	0.0029 (13)	−0.0043 (12)	0.0020 (12)
N31	0.0244 (16)	0.0262 (16)	0.0161 (14)	0.0041 (13)	0.0018 (12)	−0.0004 (12)
C32	0.0222 (17)	0.0200 (17)	0.0200 (16)	0.0016 (14)	0.0008 (14)	0.0051 (13)
N33	0.0292 (18)	0.0227 (16)	0.0276 (17)	0.0056 (14)	−0.0048 (14)	0.0005 (13)
C34	0.025 (2)	0.027 (2)	0.037 (2)	0.0053 (16)	−0.0007 (17)	0.0029 (17)
C35	0.033 (2)	0.037 (2)	0.029 (2)	0.0061 (18)	0.0088 (17)	0.0004 (18)
C36	0.034 (2)	0.033 (2)	0.0193 (18)	0.0025 (17)	0.0056 (16)	0.0026 (16)
N41	0.0249 (16)	0.0199 (15)	0.0167 (14)	−0.0003 (12)	0.0005 (12)	0.0044 (11)
C42	0.0245 (18)	0.0181 (16)	0.0154 (15)	−0.0042 (13)	−0.0021 (13)	0.0029 (13)
N43	0.0369 (19)	0.0203 (15)	0.0157 (14)	0.0020 (13)	−0.0047 (13)	0.0007 (12)
C44	0.045 (2)	0.0206 (18)	0.0182 (17)	0.0039 (17)	−0.0035 (16)	0.0005 (14)
C45	0.037 (2)	0.0200 (17)	0.0225 (18)	0.0045 (16)	−0.0027 (16)	0.0061 (14)
C46	0.0248 (18)	0.0201 (17)	0.0200 (16)	−0.0005 (14)	−0.0015 (14)	0.0087 (14)
N51	0.044 (2)	0.038 (2)	0.0158 (15)	−0.0006 (17)	0.0008 (14)	0.0076 (14)
C52	0.035 (2)	0.034 (2)	0.0154 (16)	0.0064 (17)	0.0033 (15)	0.0094 (15)
N53	0.083 (4)	0.041 (2)	0.0258 (19)	−0.007 (2)	0.013 (2)	0.0110 (17)
C54	0.035 (2)	0.035 (2)	0.040 (2)	0.0089 (19)	0.0094 (19)	0.014 (2)
N55	0.052 (3)	0.039 (2)	0.049 (3)	0.002 (2)	0.006 (2)	0.002 (2)
N61	0.043 (2)	0.0331 (19)	0.0202 (16)	−0.0012 (16)	−0.0024 (15)	−0.0008 (14)
C62	0.048 (3)	0.027 (2)	0.0219 (19)	−0.0028 (19)	−0.0040 (18)	0.0072 (16)
N63	0.142 (6)	0.037 (2)	0.025 (2)	−0.033 (3)	−0.023 (3)	0.0074 (18)
C64	0.044 (3)	0.0227 (19)	0.025 (2)	−0.0026 (18)	−0.0047 (18)	−0.0018 (16)
N65	0.050 (3)	0.040 (2)	0.0263 (19)	−0.0017 (19)	−0.0038 (17)	0.0014 (16)
O71	0.046 (2)	0.066 (3)	0.048 (2)	−0.002 (2)	0.0036 (18)	0.005 (2)
O81	0.042 (2)	0.070 (3)	0.0287 (17)	0.0037 (19)	0.0054 (15)	−0.0011 (17)

Geometric parameters (Å, º)

Fe1—N61	2.077 (4)	N31—C36	1.350 (5)
Fe1—N51	2.144 (4)	C32—N33	1.335 (5)
Fe1—N11	2.175 (3)	N33—C34	1.342 (5)
Fe1—N31	2.176 (3)	C34—C35	1.388 (6)
Fe1—N41	2.224 (3)	C34—H34	0.9500
Fe1—N21	2.230 (3)	C35—C36	1.372 (6)
N1—C22	1.367 (5)	C35—H35	0.9500
N1—C12	1.381 (5)	C36—H36	0.9500
N1—H1	0.84 (5)	N41—C42	1.335 (5)
N11—C12	1.344 (5)	N41—C46	1.357 (5)
N11—C16	1.354 (5)	C42—N43	1.351 (4)
C12—N13	1.341 (5)	N43—C44	1.327 (5)
N13—C14	1.327 (5)	C44—C45	1.394 (5)
C14—C15	1.394 (6)	C44—H44	0.9500
C14—H14	0.9500	C45—C46	1.368 (5)
C15—C16	1.365 (6)	C45—H45	0.9500
C15—H15	0.9500	C46—H46	0.9500
C16—H16	0.9500	N51—C52	1.157 (6)
N21—C22	1.343 (5)	C52—N53	1.301 (6)
N21—C26	1.352 (5)	N53—C54	1.321 (6)
C22—N23	1.343 (5)	C54—N55	1.156 (6)
N23—C24	1.330 (5)	N61—C62	1.151 (5)
C24—C25	1.396 (6)	C62—N63	1.297 (6)
C24—H24	0.9500	N63—C64	1.310 (6)
C25—C26	1.375 (6)	C64—N65	1.129 (6)
C25—H25	0.9500	O71—H71	0.860 (19)
C26—H26	0.9500	O71—H72	0.86 (2)
N3—C42	1.367 (5)	O71—H73	0.85 (2)
N3—C32	1.385 (5)	O81—H81	0.858 (19)
N3—H3	0.89 (5)	O81—H82	0.86 (2)
N31—C32	1.340 (5)	O81—H83	0.86 (2)
N61—Fe1—N51	93.91 (15)	C42—N3—C32	130.2 (3)
N61—Fe1—N11	95.09 (14)	C42—N3—H3	117 (3)
N51—Fe1—N11	93.49 (14)	C32—N3—H3	112 (3)
N61—Fe1—N31	96.63 (14)	C32—N31—C36	115.9 (3)
N51—Fe1—N31	97.71 (14)	C32—N31—Fe1	124.0 (3)
N11—Fe1—N31	163.16 (11)	C36—N31—Fe1	118.5 (3)
N61—Fe1—N41	175.73 (15)	N33—C32—N31	126.1 (3)
N51—Fe1—N41	85.54 (13)	N33—C32—N3	113.3 (3)
N11—Fe1—N41	89.17 (12)	N31—C32—N3	120.6 (3)
N31—Fe1—N41	79.26 (12)	C32—N33—C34	116.4 (4)
N61—Fe1—N21	94.04 (13)	N33—C34—C35	122.0 (4)
N51—Fe1—N21	169.19 (13)	N33—C34—H34	119.0
N11—Fe1—N21	78.51 (12)	C35—C34—H34	119.0
N31—Fe1—N21	88.64 (12)	C36—C35—C34	116.9 (4)
N41—Fe1—N21	87.07 (11)	C36—C35—H35	121.5
C22—N1—C12	130.0 (3)	C34—C35—H35	121.5
C22—N1—H1	112 (3)	N31—C36—C35	122.4 (4)
C12—N1—H1	117 (3)	N31—C36—H36	118.8
C12—N11—C16	115.6 (3)	C35—C36—H36	118.8
C12—N11—Fe1	123.4 (3)	C42—N41—C46	116.1 (3)
C16—N11—Fe1	119.1 (3)	C42—N41—Fe1	121.2 (2)
N13—C12—N11	125.8 (4)	C46—N41—Fe1	117.7 (2)
N13—C12—N1	114.0 (3)	N41—C42—N43	125.5 (3)
N11—C12—N1	120.2 (3)	N41—C42—N3	120.4 (3)
C14—N13—C12	116.3 (4)	N43—C42—N3	114.2 (3)
N13—C14—C15	122.9 (4)	C44—N43—C42	116.7 (3)
N13—C14—H14	118.5	N43—C44—C45	122.3 (4)
C15—C14—H14	118.5	N43—C44—H44	118.9
C16—C15—C14	116.1 (4)	C45—C44—H44	118.9
C16—C15—H15	121.9	C46—C45—C44	116.7 (4)
C14—C15—H15	121.9	C46—C45—H45	121.6
N11—C16—C15	122.9 (4)	C44—C45—H45	121.6
N11—C16—H16	118.5	N41—C46—C45	122.3 (3)
C15—C16—H16	118.5	N41—C46—H46	118.8
C22—N21—C26	115.9 (3)	C45—C46—H46	118.8
C22—N21—Fe1	119.2 (2)	C52—N51—Fe1	145.4 (3)
C26—N21—Fe1	118.4 (2)	N51—C52—N53	175.0 (4)
N23—C22—N21	125.8 (3)	C52—N53—C54	119.7 (4)
N23—C22—N1	114.0 (3)	N55—C54—N53	176.1 (6)
N21—C22—N1	120.2 (3)	C62—N61—Fe1	170.6 (4)
C24—N23—C22	116.6 (3)	N61—C62—N63	174.3 (5)
N23—C24—C25	122.2 (4)	C62—N63—C64	121.4 (4)
N23—C24—H24	118.9	N65—C64—N63	172.4 (5)
C25—C24—H24	118.9	H71—O71—H72	105 (3)
C26—C25—C24	116.7 (4)	H71—O71—H73	106 (3)
C26—C25—H25	121.7	H72—O71—H73	106 (3)
C24—C25—H25	121.7	H81—O81—H82	105 (3)
N21—C26—C25	122.3 (3)	H81—O81—H83	104 (3)
N21—C26—H26	118.8	H82—O81—H83	105 (3)
C25—C26—H26	118.8
C16—N11—C12—N13	6.7 (6)	C36—N31—C32—N33	6.5 (6)
Fe1—N11—C12—N13	−157.3 (3)	Fe1—N31—C32—N33	−158.9 (3)
C16—N11—C12—N1	−174.9 (4)	C36—N31—C32—N3	−174.7 (4)
Fe1—N11—C12—N1	21.1 (5)	Fe1—N31—C32—N3	19.8 (5)
C22—N1—C12—N13	−159.5 (4)	C42—N3—C32—N33	−159.9 (4)
C22—N1—C12—N11	21.9 (6)	C42—N3—C32—N31	21.2 (6)
N11—C12—N13—C14	−4.0 (6)	N31—C32—N33—C34	−4.5 (6)
N1—C12—N13—C14	177.5 (4)	N3—C32—N33—C34	176.7 (4)
C12—N13—C14—C15	−1.8 (6)	C32—N33—C34—C35	−1.3 (6)
N13—C14—C15—C16	4.3 (7)	N33—C34—C35—C36	4.2 (7)
C12—N11—C16—C15	−3.7 (6)	C32—N31—C36—C35	−3.0 (6)
Fe1—N11—C16—C15	161.0 (3)	Fe1—N31—C36—C35	163.3 (4)
C14—C15—C16—N11	−1.3 (6)	C34—C35—C36—N31	−2.0 (7)
C26—N21—C22—N23	−8.3 (6)	C46—N41—C42—N43	−6.1 (6)
Fe1—N21—C22—N23	143.1 (3)	Fe1—N41—C42—N43	148.2 (3)
C26—N21—C22—N1	173.6 (3)	C46—N41—C42—N3	174.3 (3)
Fe1—N21—C22—N1	−35.0 (5)	Fe1—N41—C42—N3	−31.4 (5)
C12—N1—C22—N23	168.6 (4)	C32—N3—C42—N41	−14.0 (6)
C12—N1—C22—N21	−13.1 (6)	C32—N3—C42—N43	166.4 (4)
N21—C22—N23—C24	5.0 (6)	N41—C42—N43—C44	3.6 (6)
N1—C22—N23—C24	−176.8 (4)	N3—C42—N43—C44	−176.8 (4)
C22—N23—C24—C25	2.2 (7)	C42—N43—C44—C45	2.6 (6)
N23—C24—C25—C26	−5.3 (7)	N43—C44—C45—C46	−5.5 (7)
C22—N21—C26—C25	4.6 (6)	C42—N41—C46—C45	2.7 (6)
Fe1—N21—C26—C25	−147.1 (3)	Fe1—N41—C46—C45	−152.6 (3)
C24—C25—C26—N21	1.7 (6)	C44—C45—C46—N41	2.7 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N23^i	0.84 (4)	2.11 (5)	2.942 (4)	170 (5)
N3—H3···N43^ii	0.89 (5)	2.03 (5)	2.918 (4)	175 (5)
O71—H71···N55	0.86 (5)	2.11 (5)	2.959 (6)	173 (6)
O71—H72···O81^iii	0.86 (6)	1.84 (5)	2.683 (6)	164 (11)
O71—H73···O71^iv	0.85 (8)	1.99 (7)	2.770 (6)	152 (8)
O81—H81···N65	0.85 (4)	2.04 (4)	2.871 (5)	166 (7)
O81—H82···O71^iii	0.86 (7)	1.89 (6)	2.683 (6)	153 (8)
O81—H83···O81^v	0.86 (8)	2.04 (7)	2.751 (5)	140 (8)
C36—H36···N53^iii	0.95	2.49	3.195 (6)	131
C46—H46···N65^vi	0.95	2.53	3.309 (6)	139

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