Chlorido­[5,10,15,20-tetra­kis­(quinoline-7-carboxamido)­porphinato]iron(III)

The title compound, [Fe(C₈₄H₅₂N₁₂O₄)Cl], crystallizes in space group C2/c. The central Fe^III cation (site symmetry 2) is coordinated in a fivefold manner, with four pyrrole N atoms of the porphyrin core in the basal sites and one Cl atom (site symmetry 2) in the apical position, which completes a slightly distorted square-pyramidal environment. The porphyrin macrocycle shows a characteristic ruffled-shape distortion and the iron atom is displaced out of the porphyrin plane by 0.42 Å with the average Fe—N distance being 2.054 (4) Å; the Fe—Cl bond length is 2.2042 (7) Å. Inter­molecular C—H...N and C—H...O hydrogen bonds occur in the crystal structure.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.088
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT420_ALERT_2_C D-H Bond Without Acceptor  N3       --H3       .     Please Check
PLAT420_ALERT_2_C D-H Bond Without Acceptor  N4       --H4       .     Please Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          5 Note
                1  1  0,   2  0  0,  -1  1  1,   1  1  1,   0  0  2,
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         46 Report
                0  2  0,   0  4  0,   0  6  0,   1  3  0,   2  2  0,   4  0  0,
                6  0  0,   0  2  1,   0  4  1,   1  5  1,   3  1  1,   4  2  1,
                5  1  1,  -9  1  2,  -6  0  2,  -3  1  2,   0  2  2,   4  0  2,
                6  0  2,  -3  1  3,   3  1  3,   4 10  3,   5  1  3,   7  1  3,
               -6  0  4,  -4  0  4,  -2  0  4,  -1  1  4,   2  0  4,   4  0  4,
                6  0  4,  -3  1  5,   1  1  5,   3  1  5,  -8  0  6,  -4  0  6,
                0  0  6,   2  0  6,  -9  1  7,  -5  1  7,   2  0  8,   6  0  8,
                8  0  8,  -1  1  9,  -5  1 10,  -5  1 26,
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....         17 Note
                0  2  0,   0  6  0,   1  3  0,   6  0  0,   0  2  1,   3  1  1,
               -6  0  2,  -3  1  3,   5  1  3,   7  1  3,  -6  0  4,  -4  0  4,
                4  0  4,  -3  1  5,   1  1  5,  -4  0  6,   8  0  8,

Alert level G
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large      12.37 Why ?
PLAT794_ALERT_5_G Tentative Bond Valency for Fe1       (III)     .       2.83 Info
PLAT795_ALERT_4_G C-Atom in CIF Coordinate List Out-of-Sequence ..         C4 Note
PLAT797_ALERT_4_G N-Atom in CIF Coordinate List Out-of-Sequence ..         N2 Note
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         11 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          2 Note
               -1  1  1,   4  0  4,
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ...........       3.74 Note
              Predicted wR2: Based on SigI   2  2.34 or SHELX Weight  8.46       
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         16 Info

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   4 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

---

Computing details

Chlorido[5,10,15,20-tetrakis(quinoline-7-carboxamido)porphinato]iron(III)

Crystal data

[Fe(C84H52N12O4)Cl]	F(000) = 2860
Mr = 1384.68	Dx = 1.399 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 23.1771 (19) Å	Cell parameters from 9906 reflections
b = 12.7959 (10) Å	θ = 2.5–26.4°
c = 22.5404 (16) Å	µ = 0.34 mm^−1
β = 100.332 (3)°	T = 100 K
V = 6576.5 (9) Å^3	Block, black
Z = 4	0.47 × 0.24 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer	Rint = 0.041
φ and ω scans	θmax = 26.4°, θmin = 2.3°
56518 measured reflections	h = −28→28
6685 independent reflections	k = −16→16
5979 reflections with I > 2σ(I)	l = −28→25

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.0246P)^2 + 12.3743P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
6685 reflections	Δρmax = 0.38 e Å^−3
469 parameters	Δρmin = −0.46 e Å^−3
0 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.

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

	x	y	z	Uiso*/Ueq
Fe1	0.500000	0.19602 (2)	0.250000	0.01406 (8)
Cl1	0.500000	0.36828 (5)	0.250000	0.03714 (17)
O1	0.41885 (5)	0.50579 (9)	0.49890 (5)	0.0241 (3)
N1	0.41780 (6)	0.16016 (10)	0.26565 (6)	0.0170 (3)
N3	0.43287 (6)	0.37351 (11)	0.43536 (6)	0.0205 (3)
N2	0.53043 (5)	0.16349 (10)	0.33957 (6)	0.0150 (3)
O2	0.22888 (6)	0.45237 (12)	0.08918 (6)	0.0395 (3)
N6	0.30417 (7)	0.79208 (13)	0.18249 (7)	0.0305 (3)
N5	0.48009 (7)	0.83155 (12)	0.40947 (7)	0.0280 (3)
N4	0.29534 (7)	0.33119 (13)	0.13238 (7)	0.0283 (3)
C5	0.43699 (7)	0.17883 (12)	0.37670 (7)	0.0161 (3)
C27	0.40879 (7)	0.19029 (13)	0.43123 (7)	0.0170 (3)
C4	0.49801 (7)	0.17192 (12)	0.38512 (7)	0.0157 (3)
C33	0.43741 (7)	0.47455 (13)	0.45470 (7)	0.0189 (3)
C3	0.53593 (7)	0.16678 (12)	0.44304 (7)	0.0180 (3)
H3A	0.524266	0.170362	0.481303	0.022*
C6	0.39996 (7)	0.17128 (12)	0.32058 (7)	0.0173 (3)
C9	0.36683 (7)	0.15418 (13)	0.22305 (7)	0.0189 (3)
C40	0.51885 (7)	0.69603 (13)	0.35087 (7)	0.0202 (3)
C32	0.40714 (7)	0.28739 (13)	0.46001 (7)	0.0179 (3)
C36	0.48723 (7)	0.72863 (13)	0.39614 (7)	0.0198 (3)
C1	0.58807 (7)	0.15469 (12)	0.36826 (7)	0.0165 (3)
C10	0.36335 (7)	0.14926 (13)	0.16065 (7)	0.0182 (3)
C11	0.30400 (7)	0.14485 (14)	0.12114 (7)	0.0209 (3)
C39	0.54339 (8)	0.77432 (14)	0.31872 (8)	0.0240 (4)
H39	0.564563	0.755848	0.287869	0.029*
C2	0.59132 (7)	0.15590 (13)	0.43272 (7)	0.0197 (3)
H2	0.625887	0.150127	0.462395	0.024*
C35	0.46154 (7)	0.65284 (13)	0.42850 (7)	0.0198 (3)
H35	0.440172	0.674535	0.458579	0.024*
C34	0.46684 (7)	0.54836 (13)	0.41734 (7)	0.0191 (3)
C28	0.38285 (8)	0.10387 (14)	0.45276 (8)	0.0243 (4)
H28	0.384045	0.038161	0.433394	0.029*
C18	0.30038 (7)	0.50730 (15)	0.17230 (8)	0.0266 (4)
C31	0.38000 (7)	0.29535 (14)	0.51067 (7)	0.0219 (3)
H31	0.379183	0.360378	0.530841	0.026*
C13	0.22732 (8)	0.04515 (16)	0.05918 (8)	0.0301 (4)
H13	0.211626	−0.020147	0.044043	0.036*
C8	0.31670 (7)	0.15940 (15)	0.25228 (8)	0.0250 (4)
H8	0.276745	0.154920	0.233226	0.030*
C26	0.29544 (7)	0.61104 (15)	0.15667 (8)	0.0256 (4)
H26	0.279465	0.630038	0.116320	0.031*
C41	0.52447 (8)	0.58790 (14)	0.34060 (8)	0.0252 (4)
H41	0.545774	0.564905	0.310748	0.030*
C25	0.31377 (7)	0.68972 (15)	0.19966 (8)	0.0254 (4)
C12	0.28099 (7)	0.04982 (15)	0.09838 (7)	0.0250 (4)
H12	0.302142	−0.012795	0.109711	0.030*
C38	0.53627 (8)	0.87648 (14)	0.33257 (8)	0.0286 (4)
H38	0.552389	0.930464	0.311643	0.034*
C29	0.35514 (8)	0.11235 (15)	0.50233 (8)	0.0280 (4)
H29	0.336836	0.053119	0.516364	0.034*
C30	0.35440 (8)	0.20768 (14)	0.53110 (8)	0.0253 (4)
H30	0.336037	0.213161	0.565423	0.030*
C21	0.33789 (7)	0.66073 (15)	0.25996 (8)	0.0273 (4)
C7	0.33700 (7)	0.17192 (15)	0.31210 (8)	0.0245 (4)
H7	0.313943	0.179663	0.342672	0.029*
C16	0.27200 (7)	0.23702 (15)	0.10545 (8)	0.0240 (4)
C15	0.21837 (7)	0.23219 (16)	0.06521 (8)	0.0282 (4)
H15	0.196822	0.294312	0.053655	0.034*
C24	0.31731 (9)	0.86345 (17)	0.22469 (9)	0.0350 (4)
H24	0.310255	0.934447	0.213352	0.042*
C42	0.49958 (8)	0.51593 (14)	0.37317 (8)	0.0247 (4)
H42	0.504288	0.443490	0.366117	0.030*
C14	0.19709 (8)	0.13711 (17)	0.04254 (8)	0.0306 (4)
H14	0.160962	0.134436	0.014936	0.037*
C19	0.32623 (8)	0.47828 (16)	0.23208 (9)	0.0322 (4)
H19	0.330884	0.406488	0.242582	0.039*
C17	0.27158 (8)	0.42904 (15)	0.12683 (8)	0.0274 (4)
C20	0.34444 (8)	0.55349 (16)	0.27455 (9)	0.0322 (4)
H20	0.361704	0.533286	0.314336	0.039*
C22	0.35155 (8)	0.74137 (17)	0.30306 (9)	0.0322 (4)
H22	0.367841	0.725187	0.343748	0.039*
C23	0.34113 (9)	0.84233 (17)	0.28562 (9)	0.0355 (4)
H23	0.349714	0.897659	0.313930	0.043*
C37	0.50447 (9)	0.90062 (15)	0.37861 (9)	0.0325 (4)
H37	0.500383	0.972306	0.388010	0.039*
H3	0.4477 (10)	0.3583 (18)	0.4048 (11)	0.037 (6)*
H4	0.3277 (12)	0.325 (2)	0.1580 (12)	0.050 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.01562 (15)	0.01438 (16)	0.01258 (15)	0.000	0.00360 (11)	0.000
Cl1	0.0760 (5)	0.0140 (3)	0.0224 (3)	0.000	0.0114 (3)	0.000
O1	0.0304 (6)	0.0229 (6)	0.0211 (6)	0.0027 (5)	0.0099 (5)	−0.0028 (5)
N1	0.0161 (6)	0.0209 (7)	0.0141 (6)	0.0000 (5)	0.0031 (5)	−0.0001 (5)
N3	0.0269 (7)	0.0189 (7)	0.0182 (7)	−0.0011 (6)	0.0106 (6)	−0.0017 (5)
N2	0.0148 (6)	0.0159 (6)	0.0149 (6)	−0.0024 (5)	0.0042 (5)	−0.0013 (5)
O2	0.0380 (8)	0.0403 (8)	0.0345 (8)	0.0130 (6)	−0.0093 (6)	0.0028 (6)
N6	0.0326 (8)	0.0328 (9)	0.0283 (8)	0.0036 (7)	0.0114 (6)	0.0024 (7)
N5	0.0375 (9)	0.0183 (7)	0.0306 (8)	−0.0004 (6)	0.0126 (7)	−0.0022 (6)
N4	0.0179 (7)	0.0311 (8)	0.0327 (8)	0.0035 (6)	−0.0044 (6)	0.0022 (7)
C5	0.0194 (7)	0.0137 (7)	0.0161 (7)	−0.0019 (6)	0.0060 (6)	−0.0007 (6)
C27	0.0157 (7)	0.0216 (8)	0.0140 (7)	−0.0010 (6)	0.0033 (6)	−0.0005 (6)
C4	0.0199 (8)	0.0132 (7)	0.0145 (7)	−0.0017 (6)	0.0046 (6)	−0.0003 (5)
C33	0.0189 (7)	0.0204 (8)	0.0170 (7)	0.0023 (6)	0.0022 (6)	−0.0010 (6)
C3	0.0221 (8)	0.0181 (8)	0.0140 (7)	−0.0030 (6)	0.0041 (6)	−0.0015 (6)
C6	0.0169 (7)	0.0193 (8)	0.0170 (7)	−0.0008 (6)	0.0064 (6)	−0.0001 (6)
C9	0.0156 (7)	0.0228 (8)	0.0179 (8)	0.0001 (6)	0.0022 (6)	−0.0003 (6)
C40	0.0192 (8)	0.0228 (8)	0.0181 (8)	−0.0016 (6)	0.0020 (6)	−0.0012 (6)
C32	0.0173 (7)	0.0204 (8)	0.0163 (7)	−0.0002 (6)	0.0038 (6)	0.0006 (6)
C36	0.0216 (8)	0.0186 (8)	0.0186 (8)	0.0000 (6)	0.0020 (6)	−0.0022 (6)
C1	0.0164 (7)	0.0170 (7)	0.0155 (7)	−0.0020 (6)	0.0012 (6)	0.0001 (6)
C10	0.0158 (7)	0.0212 (8)	0.0176 (7)	0.0016 (6)	0.0024 (6)	−0.0002 (6)
C11	0.0160 (7)	0.0325 (9)	0.0144 (7)	−0.0004 (7)	0.0037 (6)	0.0000 (7)
C39	0.0252 (8)	0.0258 (9)	0.0217 (8)	−0.0034 (7)	0.0059 (7)	−0.0012 (7)
C2	0.0209 (8)	0.0223 (8)	0.0152 (7)	−0.0016 (6)	0.0016 (6)	−0.0006 (6)
C35	0.0209 (8)	0.0209 (8)	0.0179 (8)	0.0011 (6)	0.0040 (6)	−0.0026 (6)
C34	0.0201 (8)	0.0199 (8)	0.0171 (7)	−0.0002 (6)	0.0027 (6)	−0.0009 (6)
C28	0.0292 (9)	0.0228 (8)	0.0231 (8)	−0.0067 (7)	0.0105 (7)	−0.0030 (7)
C18	0.0197 (8)	0.0339 (10)	0.0263 (9)	0.0058 (7)	0.0040 (7)	0.0037 (7)
C31	0.0243 (8)	0.0250 (9)	0.0175 (8)	0.0018 (7)	0.0071 (6)	−0.0029 (6)
C13	0.0230 (9)	0.0430 (11)	0.0245 (9)	−0.0058 (8)	0.0047 (7)	−0.0095 (8)
C8	0.0156 (8)	0.0385 (10)	0.0213 (8)	−0.0006 (7)	0.0045 (6)	−0.0024 (7)
C26	0.0218 (8)	0.0347 (10)	0.0215 (8)	0.0073 (7)	0.0067 (7)	0.0050 (7)
C41	0.0308 (9)	0.0234 (9)	0.0241 (9)	−0.0001 (7)	0.0122 (7)	−0.0047 (7)
C25	0.0184 (8)	0.0343 (10)	0.0254 (9)	0.0040 (7)	0.0087 (7)	0.0045 (7)
C12	0.0228 (8)	0.0344 (10)	0.0183 (8)	0.0002 (7)	0.0051 (6)	−0.0046 (7)
C38	0.0354 (10)	0.0227 (9)	0.0292 (9)	−0.0044 (7)	0.0099 (8)	0.0031 (7)
C29	0.0340 (10)	0.0283 (9)	0.0246 (9)	−0.0092 (8)	0.0132 (7)	0.0004 (7)
C30	0.0270 (9)	0.0328 (10)	0.0186 (8)	−0.0013 (7)	0.0112 (7)	−0.0001 (7)
C21	0.0170 (8)	0.0378 (10)	0.0272 (9)	0.0009 (7)	0.0044 (7)	0.0037 (8)
C7	0.0175 (8)	0.0373 (10)	0.0197 (8)	−0.0009 (7)	0.0063 (6)	−0.0026 (7)
C16	0.0177 (8)	0.0340 (10)	0.0202 (8)	−0.0010 (7)	0.0028 (6)	0.0006 (7)
C15	0.0175 (8)	0.0423 (11)	0.0235 (9)	0.0028 (7)	−0.0001 (7)	0.0043 (8)
C24	0.0396 (11)	0.0336 (11)	0.0336 (10)	0.0018 (9)	0.0118 (9)	0.0001 (8)
C42	0.0311 (9)	0.0189 (8)	0.0259 (9)	−0.0002 (7)	0.0100 (7)	−0.0046 (7)
C14	0.0175 (8)	0.0519 (12)	0.0213 (9)	−0.0028 (8)	0.0007 (7)	−0.0021 (8)
C19	0.0284 (9)	0.0325 (10)	0.0331 (10)	0.0049 (8)	−0.0016 (8)	0.0085 (8)
C17	0.0236 (9)	0.0334 (10)	0.0245 (9)	0.0046 (7)	0.0027 (7)	0.0051 (7)
C20	0.0260 (9)	0.0405 (11)	0.0272 (9)	0.0033 (8)	−0.0034 (7)	0.0066 (8)
C22	0.0234 (9)	0.0469 (12)	0.0259 (9)	−0.0007 (8)	0.0037 (7)	0.0011 (8)
C23	0.0343 (10)	0.0416 (11)	0.0318 (10)	−0.0018 (9)	0.0091 (8)	−0.0059 (9)
C37	0.0450 (11)	0.0194 (9)	0.0364 (10)	−0.0020 (8)	0.0159 (9)	−0.0019 (7)

Geometric parameters (Å, º)

Fe1—Cl1	2.2042 (7)	C2—H2	0.9500
Fe1—N1^i	2.0508 (13)	C35—H35	0.9500
Fe1—N1	2.0508 (13)	C35—C34	1.370 (2)
Fe1—N2	2.0581 (13)	C34—C42	1.418 (2)
Fe1—N2^i	2.0581 (13)	C28—H28	0.9500
O1—C33	1.2212 (19)	C28—C29	1.389 (2)
N1—C6	1.381 (2)	C18—C26	1.373 (3)
N1—C9	1.384 (2)	C18—C19	1.422 (3)
N3—C33	1.362 (2)	C18—C17	1.501 (3)
N3—C32	1.413 (2)	C31—H31	0.9500
N3—H3	0.85 (2)	C31—C30	1.386 (2)
N2—C4	1.3811 (19)	C13—H13	0.9500
N2—C1	1.381 (2)	C13—C12	1.392 (2)
O2—C17	1.220 (2)	C13—C14	1.386 (3)
N6—C25	1.373 (2)	C8—H8	0.9500
N6—C24	1.314 (3)	C8—C7	1.356 (2)
N5—C36	1.367 (2)	C26—H26	0.9500
N5—C37	1.314 (2)	C26—C25	1.409 (3)
N4—C16	1.413 (2)	C41—H41	0.9500
N4—C17	1.365 (2)	C41—C42	1.368 (2)
N4—H4	0.86 (3)	C25—C21	1.423 (2)
C5—C27	1.499 (2)	C12—H12	0.9500
C5—C4	1.396 (2)	C38—H38	0.9500
C5—C6	1.399 (2)	C38—C37	1.411 (3)
C27—C32	1.405 (2)	C29—H29	0.9500
C27—C28	1.387 (2)	C29—C30	1.383 (3)
C4—C3	1.439 (2)	C30—H30	0.9500
C33—C34	1.507 (2)	C21—C20	1.413 (3)
C3—H3A	0.9500	C21—C22	1.414 (3)
C3—C2	1.352 (2)	C7—H7	0.9500
C6—C7	1.437 (2)	C16—C15	1.402 (2)
C9—C10	1.396 (2)	C15—H15	0.9500
C9—C8	1.436 (2)	C15—C14	1.376 (3)
C40—C36	1.421 (2)	C24—H24	0.9500
C40—C39	1.414 (2)	C24—C23	1.411 (3)
C40—C41	1.413 (2)	C42—H42	0.9500
C32—C31	1.403 (2)	C14—H14	0.9500
C36—C35	1.408 (2)	C19—H19	0.9500
C1—C10^i	1.400 (2)	C19—C20	1.370 (3)
C1—C2	1.442 (2)	C20—H20	0.9500
C10—C11	1.500 (2)	C22—H22	0.9500
C11—C12	1.389 (2)	C22—C23	1.359 (3)
C11—C16	1.404 (2)	C23—H23	0.9500
C39—H39	0.9500	C37—H37	0.9500
C39—C38	1.361 (3)
N1^i—Fe1—Cl1	102.93 (4)	C27—C28—H28	119.6
N1—Fe1—Cl1	102.93 (4)	C27—C28—C29	120.72 (16)
N1^i—Fe1—N1	154.14 (8)	C29—C28—H28	119.6
N1—Fe1—N2^i	87.60 (5)	C26—C18—C19	119.81 (18)
N1^i—Fe1—N2^i	87.22 (5)	C26—C18—C17	117.61 (16)
N1^i—Fe1—N2	87.59 (5)	C19—C18—C17	122.20 (17)
N1—Fe1—N2	87.22 (5)	C32—C31—H31	120.2
N2—Fe1—Cl1	101.67 (4)	C30—C31—C32	119.54 (15)
N2^i—Fe1—Cl1	101.67 (4)	C30—C31—H31	120.2
N2^i—Fe1—N2	156.66 (7)	C12—C13—H13	120.5
C6—N1—Fe1	124.61 (10)	C14—C13—H13	120.5
C6—N1—C9	105.79 (13)	C14—C13—C12	119.09 (18)
C9—N1—Fe1	126.62 (10)	C9—C8—H8	126.4
C33—N3—C32	128.91 (14)	C7—C8—C9	107.25 (15)
C33—N3—H3	117.3 (16)	C7—C8—H8	126.4
C32—N3—H3	113.8 (16)	C18—C26—H26	119.6
C4—N2—Fe1	125.25 (10)	C18—C26—C25	120.89 (16)
C1—N2—Fe1	127.49 (10)	C25—C26—H26	119.6
C1—N2—C4	105.54 (12)	C40—C41—H41	119.6
C24—N6—C25	117.01 (17)	C42—C41—C40	120.76 (16)
C37—N5—C36	116.81 (15)	C42—C41—H41	119.6
C16—N4—H4	115.2 (17)	N6—C25—C26	118.31 (16)
C17—N4—C16	128.76 (15)	N6—C25—C21	122.29 (17)
C17—N4—H4	115.8 (17)	C26—C25—C21	119.27 (17)
C4—C5—C27	118.36 (14)	C11—C12—C13	120.82 (17)
C4—C5—C6	124.14 (14)	C11—C12—H12	119.6
C6—C5—C27	117.45 (13)	C13—C12—H12	119.6
C32—C27—C5	121.12 (14)	C39—C38—H38	120.7
C28—C27—C5	119.27 (14)	C39—C38—C37	118.69 (17)
C28—C27—C32	119.60 (14)	C37—C38—H38	120.7
N2—C4—C5	125.24 (14)	C28—C29—H29	120.3
N2—C4—C3	110.24 (13)	C30—C29—C28	119.50 (16)
C5—C4—C3	124.44 (14)	C30—C29—H29	120.3
O1—C33—N3	123.59 (15)	C31—C30—H30	119.5
O1—C33—C34	120.77 (15)	C29—C30—C31	121.07 (15)
N3—C33—C34	115.64 (14)	C29—C30—H30	119.5
C4—C3—H3A	126.5	C20—C21—C25	118.88 (17)
C2—C3—C4	107.03 (14)	C20—C21—C22	123.20 (17)
C2—C3—H3A	126.5	C22—C21—C25	117.86 (18)
N1—C6—C5	125.72 (14)	C6—C7—H7	126.4
N1—C6—C7	109.96 (14)	C8—C7—C6	107.14 (14)
C5—C6—C7	124.31 (14)	C8—C7—H7	126.4
N1—C9—C10	126.12 (14)	C11—C16—N4	117.64 (15)
N1—C9—C8	109.83 (14)	C15—C16—N4	122.84 (17)
C10—C9—C8	123.98 (15)	C15—C16—C11	119.52 (17)
C39—C40—C36	117.80 (15)	C16—C15—H15	120.1
C41—C40—C36	118.65 (15)	C14—C15—C16	119.74 (18)
C41—C40—C39	123.54 (15)	C14—C15—H15	120.1
C27—C32—N3	117.36 (14)	N6—C24—H24	117.6
C31—C32—N3	123.08 (15)	N6—C24—C23	124.8 (2)
C31—C32—C27	119.55 (15)	C23—C24—H24	117.6
N5—C36—C40	122.59 (15)	C34—C42—H42	119.7
N5—C36—C35	118.05 (15)	C41—C42—C34	120.66 (16)
C35—C36—C40	119.35 (15)	C41—C42—H42	119.7
N2—C1—C10^i	125.27 (14)	C13—C14—H14	119.3
N2—C1—C2	110.02 (13)	C15—C14—C13	121.31 (16)
C10^i—C1—C2	124.67 (14)	C15—C14—H14	119.3
C9—C10—C1^i	124.11 (14)	C18—C19—H19	119.9
C9—C10—C11	118.76 (14)	C20—C19—C18	120.23 (18)
C1^i—C10—C11	117.00 (14)	C20—C19—H19	119.9
C12—C11—C10	120.19 (15)	O2—C17—N4	123.52 (18)
C12—C11—C16	119.47 (15)	O2—C17—C18	121.18 (17)
C16—C11—C10	120.31 (15)	N4—C17—C18	115.26 (15)
C40—C39—H39	120.4	C21—C20—H20	119.6
C38—C39—C40	119.10 (16)	C19—C20—C21	120.86 (17)
C38—C39—H39	120.4	C19—C20—H20	119.6
C3—C2—C1	107.16 (14)	C21—C22—H22	120.4
C3—C2—H2	126.4	C23—C22—C21	119.26 (18)
C1—C2—H2	126.4	C23—C22—H22	120.4
C36—C35—H35	119.4	C24—C23—H23	120.6
C34—C35—C36	121.12 (15)	C22—C23—C24	118.78 (19)
C34—C35—H35	119.4	C22—C23—H23	120.6
C35—C34—C33	116.39 (14)	N5—C37—C38	124.99 (17)
C35—C34—C42	119.43 (15)	N5—C37—H37	117.5
C42—C34—C33	124.17 (15)	C38—C37—H37	117.5
Fe1—N1—C6—C5	−19.5 (2)	C32—C31—C30—C29	0.0 (3)
Fe1—N1—C6—C7	161.64 (11)	C36—N5—C37—C38	1.1 (3)
Fe1—N1—C9—C10	14.7 (2)	C36—C40—C39—C38	0.5 (2)
Fe1—N1—C9—C8	−162.24 (12)	C36—C40—C41—C42	0.6 (3)
Fe1—N2—C4—C5	16.4 (2)	C36—C35—C34—C33	−179.90 (14)
Fe1—N2—C4—C3	−166.77 (10)	C36—C35—C34—C42	1.1 (2)
Fe1—N2—C1—C10^i	−11.3 (2)	C1—N2—C4—C5	−177.68 (15)
Fe1—N2—C1—C2	166.51 (11)	C1—N2—C4—C3	−0.84 (17)
O1—C33—C34—C35	−12.0 (2)	C1^i—C10—C11—C12	84.9 (2)
O1—C33—C34—C42	166.96 (16)	C1^i—C10—C11—C16	−93.30 (19)
N1—C6—C7—C8	1.0 (2)	C10—C9—C8—C7	−175.04 (17)
N1—C9—C10—C1^i	−3.2 (3)	C10^i—C1—C2—C3	177.04 (15)
N1—C9—C10—C11	−179.00 (15)	C10—C11—C12—C13	−176.68 (15)
N1—C9—C8—C7	1.9 (2)	C10—C11—C16—N4	−5.5 (2)
N3—C33—C34—C35	167.42 (15)	C10—C11—C16—C15	175.72 (15)
N3—C33—C34—C42	−13.6 (2)	C11—C16—C15—C14	1.4 (3)
N3—C32—C31—C30	178.28 (15)	C39—C40—C36—N5	−0.2 (2)
N2—C4—C3—C2	0.36 (18)	C39—C40—C36—C35	179.16 (15)
N2—C1—C2—C3	−0.80 (18)	C39—C40—C41—C42	−179.88 (17)
N6—C25—C21—C20	177.71 (17)	C39—C38—C37—N5	−0.8 (3)
N6—C25—C21—C22	0.7 (3)	C35—C34—C42—C41	−1.8 (3)
N6—C24—C23—C22	−0.1 (3)	C28—C27—C32—N3	−178.40 (15)
N5—C36—C35—C34	179.82 (16)	C28—C27—C32—C31	0.9 (2)
N4—C16—C15—C14	−177.35 (16)	C28—C29—C30—C31	1.1 (3)
C5—C27—C32—N3	0.2 (2)	C18—C26—C25—N6	−175.69 (16)
C5—C27—C32—C31	179.55 (14)	C18—C26—C25—C21	0.3 (2)
C5—C27—C28—C29	−178.49 (16)	C18—C19—C20—C21	0.1 (3)
C5—C4—C3—C2	177.23 (15)	C8—C9—C10—C1^i	173.32 (16)
C5—C6—C7—C8	−177.82 (16)	C8—C9—C10—C11	−2.5 (3)
C27—C5—C4—N2	−178.50 (14)	C26—C18—C19—C20	2.1 (3)
C27—C5—C4—C3	5.1 (2)	C26—C18—C17—O2	−27.1 (3)
C27—C5—C6—N1	−179.83 (14)	C26—C18—C17—N4	155.05 (17)
C27—C5—C6—C7	−1.2 (2)	C26—C25—C21—C20	1.9 (2)
C27—C32—C31—C30	−1.0 (2)	C26—C25—C21—C22	−175.12 (16)
C27—C28—C29—C30	−1.2 (3)	C41—C40—C36—N5	179.38 (16)
C4—N2—C1—C10^i	−176.82 (15)	C41—C40—C36—C35	−1.3 (2)
C4—N2—C1—C2	0.99 (17)	C41—C40—C39—C38	−179.03 (17)
C4—C5—C27—C32	79.19 (19)	C25—N6—C24—C23	0.9 (3)
C4—C5—C27—C28	−102.17 (18)	C25—C21—C20—C19	−2.1 (3)
C4—C5—C6—N1	−2.7 (3)	C25—C21—C22—C23	0.2 (3)
C4—C5—C6—C7	176.00 (16)	C12—C11—C16—N4	176.33 (15)
C4—C3—C2—C1	0.25 (18)	C12—C11—C16—C15	−2.4 (2)
C33—N3—C32—C27	−179.50 (15)	C12—C13—C14—C15	−1.7 (3)
C33—N3—C32—C31	1.2 (3)	C21—C22—C23—C24	−0.5 (3)
C33—C34—C42—C41	179.28 (16)	C16—N4—C17—O2	−11.7 (3)
C6—N1—C9—C10	175.64 (16)	C16—N4—C17—C18	166.07 (17)
C6—N1—C9—C8	−1.26 (18)	C16—C11—C12—C13	1.5 (2)
C6—C5—C27—C32	−103.49 (18)	C16—C15—C14—C13	0.7 (3)
C6—C5—C27—C28	75.2 (2)	C24—N6—C25—C26	174.62 (16)
C6—C5—C4—N2	4.4 (2)	C24—N6—C25—C21	−1.2 (3)
C6—C5—C4—C3	−172.04 (15)	C14—C13—C12—C11	0.6 (3)
C9—N1—C6—C5	179.00 (15)	C19—C18—C26—C25	−2.3 (3)
C9—N1—C6—C7	0.17 (18)	C19—C18—C17—O2	145.79 (19)
C9—C10—C11—C12	−99.02 (19)	C19—C18—C17—N4	−32.1 (2)
C9—C10—C11—C16	82.8 (2)	C17—N4—C16—C11	−176.58 (17)
C9—C8—C7—C6	−1.8 (2)	C17—N4—C16—C15	2.1 (3)
C40—C36—C35—C34	0.4 (2)	C17—C18—C26—C25	170.75 (15)
C40—C39—C38—C37	−0.1 (3)	C17—C18—C19—C20	−170.57 (17)
C40—C41—C42—C34	1.0 (3)	C20—C21—C22—C23	−176.70 (18)
C32—N3—C33—O1	0.4 (3)	C22—C21—C20—C19	174.78 (18)
C32—N3—C33—C34	−179.03 (15)	C37—N5—C36—C40	−0.6 (3)
C32—C27—C28—C29	0.2 (3)	C37—N5—C36—C35	−179.97 (17)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O2	0.95	2.25	2.871 (3)	122
C31—H31···O1	0.95	2.25	2.867 (2)	122
C42—H42···Cl1	0.95	2.77	3.3596 (18)	121
C3—H3A···N5^ii	0.95	2.48	3.411 (2)	166
C14—H14···O1^iii	0.95	2.45	3.165 (2)	132

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