Ammonium bis­{3-anilinocarbonyl-1-[(5-chloro-2-oxidophen­yl)diazen­yl]-2-naphtholato}ferrate(III) methanol solvate

The title compound, (NH₄)[Fe(C₂₃H₂₄ClN₃O₃)₂]·CH₄O, is a charge-control agent used in electrophotography. The central Fe^III atom is coordinated by four O atoms and two N atoms of two symmetry-independent ligands. The metallic complex has no crystallographic symmetry. The structure features hydrogen-bonded double chains, which run along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 93 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.054
• wR factor = 0.157
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found





Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT353_ALERT_3_C Long    N-H Bond (0.87A)   N7     -   H1A    ...       1.06 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2006 or 2005??); program(s) used to solve structure: SIR2004 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure.

Ammonium bis{3-anilinocarbonyl-1-[(5-chloro-2-oxidophenyl)diazenyl]- 2-naphtholato}ferrate(III) methanol solvate

Crystal data

(NH4)[Fe(C23H24ClN3O3)2]·CH4O	Z = 2
Mr = 937.58	F(000) = 966.00
Triclinic, P1	Dx = 1.501 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 10.1107 (4) Å	Cell parameters from 32362 reflections
b = 14.1645 (6) Å	θ = 3.0–68.3°
c = 15.3877 (7) Å	µ = 0.56 mm^−1
α = 103.2240 (11)°	T = 93 K
β = 102.8270 (12)°	Platelet, black
γ = 94.0860 (12)°	0.20 × 0.20 × 0.10 mm
V = 2074.39 (15) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	6242 reflections with F^2 > 2σ(F^2)
Detector resolution: 10 pixels mm^-1	Rint = 0.054
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = 0→13
Tmin = 0.896, Tmax = 0.940	k = −18→18
32362 measured reflections	l = −19→19
9404 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.054	w = 1/[σ^2(Fo^2) + (0.0804P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.157	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.77 e Å^−3
9404 reflections	Δρmin = −0.92 e Å^−3
578 parameters

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Fe1	0.23749 (4)	0.53196 (3)	0.21829 (3)	0.02151 (13)
Cl1	0.06721 (10)	0.98812 (6)	0.24890 (7)	0.0414 (2)
Cl2	−0.14568 (9)	0.09132 (6)	0.06240 (6)	0.0355 (2)
O1	0.1200 (2)	0.59087 (15)	0.29181 (14)	0.0235 (4)
O2	0.3505 (2)	0.47977 (15)	0.14409 (14)	0.0236 (4)
O3	0.7114 (2)	0.36729 (16)	0.17350 (16)	0.0309 (5)
O4	0.0807 (2)	0.49931 (15)	0.11767 (14)	0.0241 (4)
O5	0.3887 (2)	0.56088 (15)	0.32109 (14)	0.0230 (4)
O6	0.8019 (2)	0.62629 (16)	0.44624 (16)	0.0286 (5)
O7	−0.0202 (3)	0.3349 (2)	0.4066 (2)	0.0641 (9)
N1	0.2756 (2)	0.65931 (18)	0.20137 (17)	0.0219 (5)
N2	0.3672 (2)	0.69369 (18)	0.16663 (17)	0.0235 (5)
N3	0.4816 (2)	0.32169 (19)	0.12315 (18)	0.0264 (5)
N4	0.1971 (2)	0.40401 (18)	0.23214 (17)	0.0218 (5)
N5	0.2654 (2)	0.35501 (18)	0.28254 (17)	0.0230 (5)
N6	0.6079 (2)	0.69220 (18)	0.40075 (18)	0.0248 (5)
N7	−0.0926 (2)	0.4810 (2)	0.32164 (19)	0.0294 (6)
C1	0.1074 (3)	0.6820 (2)	0.2846 (2)	0.0235 (6)
C2	0.0176 (3)	0.7386 (2)	0.3252 (2)	0.0260 (6)
C3	0.0069 (3)	0.8324 (2)	0.3137 (2)	0.0299 (7)
C4	0.0875 (3)	0.8715 (2)	0.2644 (2)	0.0296 (7)
C5	0.1784 (3)	0.8189 (2)	0.2255 (2)	0.0254 (6)
C6	0.1869 (3)	0.7237 (2)	0.2351 (2)	0.0219 (6)
C7	0.4585 (3)	0.5339 (2)	0.1372 (2)	0.0227 (6)
C8	0.4633 (3)	0.6347 (2)	0.1408 (2)	0.0222 (6)
C9	0.5776 (3)	0.6854 (2)	0.1201 (2)	0.0251 (6)
C10	0.5832 (3)	0.7841 (2)	0.1153 (2)	0.0291 (7)
C11	0.6956 (3)	0.8288 (2)	0.0962 (2)	0.0306 (7)
C12	0.8071 (3)	0.7783 (2)	0.0816 (2)	0.0307 (7)
C13	0.8034 (3)	0.6826 (2)	0.0853 (2)	0.0303 (7)
C14	0.6892 (3)	0.6340 (2)	0.1048 (2)	0.0265 (6)
C15	0.6873 (3)	0.5369 (2)	0.1117 (2)	0.0266 (6)
C16	0.5771 (3)	0.4863 (2)	0.1272 (2)	0.0248 (6)
C17	0.5952 (3)	0.3871 (2)	0.1430 (2)	0.0248 (6)
C18	0.4708 (3)	0.2267 (2)	0.1371 (2)	0.0270 (7)
C19	0.5821 (3)	0.1770 (2)	0.1605 (2)	0.0332 (7)
C20	0.5582 (4)	0.0837 (2)	0.1732 (2)	0.0381 (8)
C21	0.4276 (4)	0.0390 (2)	0.1613 (2)	0.0392 (8)
C22	0.3167 (3)	0.0885 (2)	0.1373 (2)	0.0335 (7)
C23	0.3380 (3)	0.1820 (2)	0.1258 (2)	0.0282 (7)
C24	0.0246 (3)	0.4081 (2)	0.1041 (2)	0.0227 (6)
C25	−0.0867 (3)	0.3628 (2)	0.0296 (2)	0.0255 (6)
C26	−0.1396 (3)	0.2669 (2)	0.0192 (2)	0.0270 (7)
C27	−0.0819 (3)	0.2143 (2)	0.0814 (2)	0.0264 (6)
C28	0.0260 (3)	0.2557 (2)	0.1557 (2)	0.0254 (6)
C29	0.0783 (3)	0.3528 (2)	0.1663 (2)	0.0233 (6)
C30	0.4527 (3)	0.4942 (2)	0.3544 (2)	0.0230 (6)
C31	0.3926 (3)	0.3966 (2)	0.3398 (2)	0.0218 (6)
C32	0.4649 (3)	0.3291 (2)	0.3842 (2)	0.0220 (6)
C33	0.4090 (3)	0.2308 (2)	0.3715 (2)	0.0255 (6)
C34	0.4793 (3)	0.1704 (2)	0.4174 (2)	0.0285 (7)
C35	0.6085 (3)	0.2049 (2)	0.4796 (2)	0.0292 (7)
C36	0.6662 (3)	0.2987 (2)	0.4917 (2)	0.0276 (7)
C37	0.5965 (3)	0.3616 (2)	0.4435 (2)	0.0237 (6)
C38	0.6575 (3)	0.4579 (2)	0.4521 (2)	0.0248 (6)
C39	0.5923 (3)	0.5221 (2)	0.4090 (2)	0.0225 (6)
C40	0.6739 (3)	0.6182 (2)	0.4204 (2)	0.0246 (6)
C41	0.6664 (3)	0.7903 (2)	0.4124 (2)	0.0249 (6)
C42	0.7825 (3)	0.8338 (2)	0.4818 (2)	0.0287 (7)
C43	0.8317 (3)	0.9308 (2)	0.4928 (2)	0.0334 (7)
C44	0.7668 (3)	0.9843 (2)	0.4354 (2)	0.0353 (8)
C45	0.6500 (3)	0.9413 (2)	0.3667 (2)	0.0358 (8)
C46	0.6001 (2)	0.84463 (18)	0.35574 (18)	0.0308 (7)
C47	−0.0829 (2)	0.23704 (18)	0.36963 (18)	0.0448 (9)
H2	−0.0354	0.7127	0.3602	0.031*
H3	−0.0555	0.8701	0.3395	0.036*
H3N	0.4045	0.3409	0.0983	0.032*
H4	0.5095	0.8197	0.1253	0.035*
H5	0.2338	0.8467	0.1930	0.030*
H6N	0.5188	0.6789	0.3782	0.030*
H1A	−0.0130	0.5219	0.3057	0.035*
H1B	−0.1277	0.5294	0.3612	0.035*
H1C	−0.0615	0.4325	0.3484	0.035*
H1D	−0.1555	0.4519	0.2751	0.035*
H7O	0.0495	0.3370	0.4489	0.077*
H11	0.6977	0.8950	0.0929	0.037*
H12	0.8840	0.8105	0.0694	0.037*
H13	0.8779	0.6481	0.0748	0.036*
H15	0.7652	0.5048	0.1054	0.032*
H19	0.6726	0.2063	0.1676	0.040*
H20	0.6338	0.0500	0.1905	0.046*
H21	0.4134	−0.0251	0.1694	0.047*
H22	0.2263	0.0581	0.1289	0.040*
H23	0.2621	0.2161	0.1102	0.034*
H25	−0.1253	0.3979	−0.0135	0.031*
H26	−0.2157	0.2366	−0.0305	0.032*
H28	0.0635	0.2197	0.1982	0.031*
H33	0.3218	0.2065	0.3306	0.031*
H34	0.4408	0.1045	0.4073	0.034*
H35	0.6549	0.1631	0.5127	0.035*
H36	0.7535	0.3217	0.5328	0.033*
H38	0.7478	0.4786	0.4896	0.030*
H42	0.8278	0.7973	0.5214	0.034*
H43	0.9108	0.9607	0.5402	0.040*
H44	0.8019	1.0505	0.4429	0.042*
H45	0.6045	0.9781	0.3275	0.043*
H46	0.5200	0.8153	0.3090	0.037*
H47A	−0.1722	0.2358	0.3280	0.054*
H47B	−0.0954	0.2081	0.4198	0.054*
H47C	−0.0247	0.1995	0.3355	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0238 (2)	0.0190 (2)	0.0233 (2)	0.00484 (17)	0.00399 (18)	0.00955 (18)
Cl1	0.0592 (6)	0.0257 (4)	0.0539 (5)	0.0200 (4)	0.0282 (4)	0.0208 (4)
Cl2	0.0380 (4)	0.0215 (4)	0.0421 (5)	−0.0007 (3)	0.0022 (3)	0.0070 (3)
O1	0.0253 (11)	0.0220 (11)	0.0267 (11)	0.0069 (8)	0.0068 (9)	0.0112 (9)
O2	0.0273 (11)	0.0188 (10)	0.0254 (11)	0.0040 (8)	0.0057 (9)	0.0077 (9)
O3	0.0277 (12)	0.0255 (12)	0.0424 (13)	0.0077 (9)	0.0066 (10)	0.0146 (10)
O4	0.0259 (11)	0.0204 (10)	0.0271 (11)	0.0029 (8)	0.0044 (9)	0.0100 (9)
O5	0.0233 (11)	0.0200 (10)	0.0277 (11)	0.0051 (8)	0.0046 (9)	0.0108 (9)
O6	0.0244 (12)	0.0247 (11)	0.0374 (13)	0.0055 (9)	0.0060 (10)	0.0102 (10)
O7	0.0588 (19)	0.0429 (16)	0.075 (2)	−0.0060 (14)	−0.0285 (16)	0.0315 (16)
N1	0.0263 (13)	0.0180 (12)	0.0224 (13)	0.0045 (10)	0.0037 (10)	0.0085 (10)
N2	0.0260 (14)	0.0223 (13)	0.0225 (13)	0.0038 (10)	0.0024 (11)	0.0096 (10)
N3	0.0273 (14)	0.0228 (13)	0.0307 (14)	0.0074 (11)	0.0050 (11)	0.0111 (11)
N4	0.0242 (13)	0.0197 (12)	0.0221 (12)	0.0042 (10)	0.0036 (10)	0.0078 (10)
N5	0.0255 (13)	0.0213 (13)	0.0231 (13)	0.0043 (10)	0.0042 (10)	0.0087 (10)
N6	0.0255 (14)	0.0201 (13)	0.0305 (14)	0.0037 (10)	0.0053 (11)	0.0108 (11)
N7	0.0287 (14)	0.0261 (14)	0.0359 (15)	0.0062 (11)	0.0084 (12)	0.0112 (12)
C1	0.0264 (16)	0.0201 (15)	0.0237 (15)	0.0047 (12)	0.0029 (12)	0.0076 (12)
C2	0.0245 (16)	0.0261 (16)	0.0304 (17)	0.0052 (12)	0.0081 (13)	0.0111 (14)
C3	0.0339 (18)	0.0258 (16)	0.0341 (18)	0.0119 (14)	0.0124 (15)	0.0095 (14)
C4	0.042 (2)	0.0188 (15)	0.0328 (18)	0.0120 (13)	0.0094 (15)	0.0135 (13)
C5	0.0272 (16)	0.0228 (15)	0.0283 (16)	0.0040 (12)	0.0060 (13)	0.0113 (13)
C6	0.0245 (15)	0.0184 (14)	0.0233 (15)	0.0073 (12)	0.0034 (12)	0.0070 (12)
C7	0.0228 (15)	0.0266 (16)	0.0209 (14)	0.0039 (12)	0.0056 (12)	0.0102 (13)
C8	0.0240 (15)	0.0222 (15)	0.0217 (15)	0.0056 (12)	0.0035 (12)	0.0090 (12)
C9	0.0285 (17)	0.0250 (16)	0.0207 (15)	0.0027 (12)	0.0018 (12)	0.0076 (13)
C10	0.0328 (18)	0.0259 (17)	0.0302 (17)	0.0044 (13)	0.0071 (14)	0.0101 (14)
C11	0.0389 (19)	0.0230 (16)	0.0317 (18)	0.0011 (14)	0.0097 (15)	0.0105 (14)
C12	0.0328 (18)	0.0330 (18)	0.0287 (17)	0.0004 (14)	0.0094 (14)	0.0119 (14)
C13	0.0295 (17)	0.0327 (18)	0.0304 (17)	0.0059 (14)	0.0068 (14)	0.0115 (14)
C14	0.0285 (17)	0.0276 (17)	0.0254 (16)	0.0054 (13)	0.0065 (13)	0.0103 (13)
C15	0.0286 (17)	0.0255 (16)	0.0283 (16)	0.0073 (13)	0.0090 (13)	0.0086 (13)
C16	0.0279 (16)	0.0228 (15)	0.0241 (15)	0.0054 (12)	0.0035 (13)	0.0086 (13)
C17	0.0283 (17)	0.0227 (16)	0.0260 (16)	0.0051 (12)	0.0086 (13)	0.0086 (13)
C18	0.0362 (18)	0.0198 (15)	0.0253 (16)	0.0070 (13)	0.0073 (14)	0.0052 (13)
C19	0.0334 (19)	0.0273 (17)	0.041 (2)	0.0069 (14)	0.0071 (15)	0.0142 (15)
C20	0.042 (2)	0.0262 (18)	0.050 (2)	0.0114 (15)	0.0113 (18)	0.0149 (16)
C21	0.051 (2)	0.0250 (17)	0.046 (2)	0.0066 (16)	0.0137 (18)	0.0163 (16)
C22	0.041 (2)	0.0280 (17)	0.0297 (17)	−0.0007 (15)	0.0072 (15)	0.0062 (14)
C23	0.0336 (18)	0.0220 (16)	0.0282 (17)	0.0042 (13)	0.0073 (14)	0.0044 (13)
C24	0.0253 (16)	0.0211 (15)	0.0248 (15)	0.0043 (12)	0.0089 (12)	0.0084 (12)
C25	0.0240 (16)	0.0295 (17)	0.0242 (16)	0.0071 (12)	0.0032 (12)	0.0107 (13)
C26	0.0255 (16)	0.0275 (17)	0.0257 (16)	0.0022 (13)	0.0042 (13)	0.0044 (13)
C27	0.0286 (17)	0.0199 (15)	0.0328 (17)	0.0021 (12)	0.0113 (14)	0.0075 (13)
C28	0.0290 (17)	0.0217 (15)	0.0270 (16)	0.0047 (12)	0.0062 (13)	0.0091 (13)
C29	0.0220 (15)	0.0228 (15)	0.0248 (15)	0.0040 (12)	0.0043 (12)	0.0065 (13)
C30	0.0289 (16)	0.0193 (15)	0.0224 (15)	0.0072 (12)	0.0053 (12)	0.0081 (12)
C31	0.0228 (15)	0.0231 (15)	0.0205 (14)	0.0059 (12)	0.0043 (12)	0.0075 (12)
C32	0.0261 (16)	0.0203 (15)	0.0210 (14)	0.0056 (12)	0.0050 (12)	0.0081 (12)
C33	0.0298 (17)	0.0232 (15)	0.0237 (15)	0.0036 (13)	0.0057 (13)	0.0073 (13)
C34	0.0368 (19)	0.0225 (16)	0.0296 (17)	0.0079 (13)	0.0095 (14)	0.0105 (13)
C35	0.0334 (18)	0.0284 (17)	0.0317 (17)	0.0124 (14)	0.0093 (14)	0.0153 (14)
C36	0.0308 (17)	0.0274 (17)	0.0266 (16)	0.0108 (13)	0.0036 (13)	0.0121 (13)
C37	0.0278 (16)	0.0232 (15)	0.0219 (15)	0.0082 (12)	0.0056 (12)	0.0079 (13)
C38	0.0253 (16)	0.0240 (15)	0.0248 (15)	0.0045 (12)	0.0041 (13)	0.0071 (13)
C39	0.0257 (16)	0.0192 (14)	0.0237 (15)	0.0048 (12)	0.0058 (12)	0.0073 (12)
C40	0.0265 (17)	0.0241 (16)	0.0244 (16)	0.0056 (12)	0.0059 (13)	0.0081 (13)
C41	0.0294 (16)	0.0184 (15)	0.0279 (16)	0.0037 (12)	0.0084 (13)	0.0063 (13)
C42	0.0303 (17)	0.0245 (16)	0.0317 (17)	0.0067 (13)	0.0059 (14)	0.0087 (14)
C43	0.0306 (18)	0.0264 (17)	0.0394 (19)	0.0011 (14)	0.0074 (15)	0.0026 (15)
C44	0.042 (2)	0.0193 (16)	0.049 (2)	0.0048 (14)	0.0192 (18)	0.0103 (15)
C45	0.048 (2)	0.0248 (17)	0.0366 (19)	0.0079 (15)	0.0072 (16)	0.0131 (15)
C46	0.0372 (19)	0.0229 (16)	0.0296 (17)	0.0046 (13)	0.0031 (14)	0.0061 (14)
C47	0.043 (2)	0.039 (2)	0.051 (2)	0.0028 (17)	0.0074 (19)	0.0122 (19)

Geometric parameters (Å, º)

Fe1—O1	1.921 (2)	C15—C16	1.376 (4)
Fe1—O2	1.863 (2)	C15—H15	0.950
Fe1—O4	1.8978 (18)	C16—C17	1.497 (4)
Fe1—O5	1.8833 (18)	C18—C19	1.392 (5)
Fe1—N1	1.905 (2)	C18—C23	1.399 (4)
Fe1—N4	1.899 (2)	C19—C20	1.393 (5)
Cl1—C4	1.742 (3)	C19—H19	0.950
Cl2—C27	1.749 (3)	C20—C21	1.378 (5)
O1—C1	1.333 (3)	C20—H20	0.950
O2—C7	1.327 (3)	C21—C22	1.389 (5)
O3—C17	1.242 (3)	C21—H21	0.950
O4—C24	1.324 (3)	C22—C23	1.385 (5)
O5—C30	1.317 (4)	C22—H22	0.950
O6—C40	1.255 (3)	C23—H23	0.950
O7—C47	1.415 (3)	C24—C25	1.408 (3)
O7—H7O	0.840	C24—C29	1.413 (4)
N1—N2	1.287 (4)	C25—C26	1.385 (4)
N1—C6	1.418 (4)	C25—H25	0.950
N2—C8	1.391 (4)	C26—C27	1.397 (5)
N3—C17	1.354 (4)	C26—H26	0.950
N3—C18	1.411 (4)	C27—C28	1.375 (3)
N3—H3N	0.880	C28—C29	1.398 (4)
N4—N5	1.279 (3)	C28—H28	0.950
N4—C29	1.412 (3)	C30—C31	1.417 (4)
N5—C31	1.389 (3)	C30—C39	1.448 (4)
N6—C40	1.338 (4)	C31—C32	1.447 (4)
N6—C41	1.426 (4)	C32—C33	1.418 (4)
N6—H6N	0.880	C32—C37	1.413 (3)
N7—H1A	1.063	C33—C34	1.369 (4)
N7—H1B	0.953	C33—H33	0.950
N7—H1C	0.919	C34—C35	1.415 (4)
N7—H1D	0.844	C34—H34	0.950
C1—C2	1.409 (4)	C35—C36	1.366 (4)
C1—C6	1.409 (5)	C35—H35	0.950
C2—C3	1.388 (4)	C36—C37	1.414 (4)
C2—H2	0.950	C36—H36	0.950
C3—C4	1.396 (5)	C37—C38	1.420 (4)
C3—H3	0.950	C38—C39	1.367 (4)
C4—C5	1.376 (5)	C38—H38	0.950
C5—C6	1.397 (4)	C39—C40	1.494 (4)
C5—H5	0.950	C41—C42	1.392 (3)
C7—C8	1.413 (4)	C41—C46	1.387 (4)
C7—C16	1.437 (4)	C42—C43	1.387 (4)
C8—C9	1.450 (4)	C42—H42	0.950
C9—C10	1.414 (4)	C43—C44	1.379 (5)
C9—C14	1.420 (4)	C43—H43	0.950
C10—C11	1.382 (5)	C44—C45	1.391 (4)
C10—H4	0.950	C44—H44	0.950
C11—C12	1.409 (5)	C45—C46	1.384 (4)
C11—H11	0.950	C45—H45	0.950
C12—C13	1.369 (5)	C46—H46	0.950
C12—H12	0.950	C47—H47A	0.980
C13—C14	1.424 (5)	C47—H47B	0.980
C13—H13	0.950	C47—H47C	0.980
C14—C15	1.403 (4)
O1···N7	2.747 (3)	H7O···H1C	2.425
O1···H1A	1.687	H7O···H42^i	2.418
O1···H36^i	2.677	H11···H20^vi	2.573
O3···N7^ii	2.753 (3)	H12···H23^vii	2.755
O3···H1D^ii	1.916	H15···C25^ii	2.790
O4···H25^iii	2.488	H15···H25^ii	2.596
O6···O7^i	2.709 (3)	H19···H47A^ii	2.539
O6···H2^ii	2.716	H20···H11^viii	2.573
O6···H1B^ii	1.957	H20···H45^viii	2.603
O6···H7O^i	1.886	H21···H4^viii	2.479
O7···O6^i	2.709 (3)	H21···H5^viii	2.617
O7···N7	2.748 (4)	H21···H45^viii	2.738
O7···H1C	1.835	H23···H12^vii	2.755
N2···H26^iii	2.728	H25···O4^iii	2.488
N7···O1	2.747 (3)	H25···H15^iv	2.596
N7···O3^iv	2.753 (3)	H26···N2^iii	2.728
N7···O7	2.748 (4)	H26···H5^iii	2.468
C1···H1A	2.618	H28···H47C	2.533
C25···H15^iv	2.790	H34···H45^viii	2.788
C40···H1B^ii	2.661	H35···H44^viii	2.484
H2···O6^iv	2.716	H36···O1^i	2.677
H2···H1A	2.683	H38···H1B^ii	2.763
H2···H1B	2.700	H42···H7O^i	2.418
H3···H43^v	2.753	H42···H47B^i	2.668
H4···H21^vi	2.479	H42···H47C^i	2.609
H5···H21^vi	2.617	H43···H3^v	2.753
H5···H26^iii	2.468	H43···H43^ix	2.712
H1A···O1	1.687	H44···H35^vi	2.484
H1A···C1	2.618	H44···H47B^x	2.527
H1A···H2	2.683	H45···H20^vi	2.603
H1B···O6^iv	1.957	H45···H21^vi	2.738
H1B···C40^iv	2.661	H45···H34^vi	2.788
H1B···H2	2.700	H47A···H19^iv	2.539
H1B···H38^iv	2.763	H47B···H42^i	2.668
H1C···O7	1.835	H47B···H44^xi	2.527
H1C···H7O	2.425	H47C···H28	2.533
H1D···O3^iv	1.916	H47C···H42^i	2.609
H7O···O6^i	1.886
O1—Fe1—O2	177.20 (10)	N3—C18—C23	116.0 (2)
O1—Fe1—O4	86.78 (8)	C19—C18—C23	119.9 (3)
O1—Fe1—O5	91.82 (8)	C18—C19—C20	118.8 (3)
O1—Fe1—N1	85.30 (10)	C18—C19—H19	120.6
O1—Fe1—N4	95.17 (11)	C20—C19—H19	120.6
O2—Fe1—O4	92.26 (9)	C19—C20—C21	121.6 (3)
O2—Fe1—O5	89.25 (9)	C19—C20—H20	119.2
O2—Fe1—N1	92.12 (11)	C21—C20—H20	119.2
O2—Fe1—N4	87.38 (11)	C20—C21—C22	119.5 (3)
O4—Fe1—O5	177.27 (10)	C20—C21—H21	120.3
O4—Fe1—N1	92.75 (9)	C22—C21—H21	120.3
O4—Fe1—N4	85.99 (9)	C21—C22—C23	120.0 (3)
O5—Fe1—N1	89.47 (9)	C21—C22—H22	120.0
O5—Fe1—N4	91.81 (9)	C23—C22—H22	120.0
N1—Fe1—N4	178.62 (9)	C18—C23—C22	120.3 (3)
Fe1—O1—C1	110.8 (2)	C18—C23—H23	119.9
Fe1—O2—C7	121.25 (18)	C22—C23—H23	119.8
Fe1—O4—C24	111.15 (19)	O4—C24—C25	122.9 (3)
Fe1—O5—C30	124.08 (16)	O4—C24—C29	119.2 (2)
C47—O7—H7O	109.5	C25—C24—C29	117.9 (2)
Fe1—N1—N2	130.5 (2)	C24—C25—C26	119.8 (3)
Fe1—N1—C6	111.7 (2)	C24—C25—H25	120.1
N2—N1—C6	117.8 (2)	C26—C25—H25	120.1
N1—N2—C8	118.9 (2)	C25—C26—C27	120.4 (2)
C17—N3—C18	128.5 (2)	C25—C26—H26	119.8
C17—N3—H3N	115.8	C27—C26—H26	119.8
C18—N3—H3N	115.8	Cl2—C27—C26	119.1 (2)
Fe1—N4—N5	131.30 (18)	Cl2—C27—C28	119.0 (2)
Fe1—N4—C29	111.7 (2)	C26—C27—C28	121.9 (2)
N5—N4—C29	116.5 (2)	C27—C28—C29	117.5 (3)
N4—N5—C31	119.5 (2)	C27—C28—H28	121.3
C40—N6—C41	127.0 (2)	C29—C28—H28	121.3
C40—N6—H6N	116.5	N4—C29—C24	111.7 (2)
C41—N6—H6N	116.5	N4—C29—C28	125.5 (2)
H1A—N7—H1B	103.3	C24—C29—C28	122.5 (2)
H1A—N7—H1C	112.2	O5—C30—C31	123.7 (2)
H1A—N7—H1D	113.7	O5—C30—C39	118.3 (2)
H1B—N7—H1C	113.2	C31—C30—C39	118.1 (2)
H1B—N7—H1D	109.8	N5—C31—C30	125.7 (2)
H1C—N7—H1D	104.9	N5—C31—C32	113.4 (2)
O1—C1—C2	122.3 (3)	C30—C31—C32	120.8 (2)
O1—C1—C6	119.1 (2)	C31—C32—C33	122.8 (2)
C2—C1—C6	118.6 (2)	C31—C32—C37	119.3 (2)
C1—C2—C3	119.6 (3)	C33—C32—C37	117.9 (2)
C1—C2—H2	120.2	C32—C33—C34	120.8 (2)
C3—C2—H2	120.2	C32—C33—H33	119.6
C2—C3—C4	120.2 (3)	C34—C33—H33	119.6
C2—C3—H3	119.9	C33—C34—C35	120.8 (3)
C4—C3—H3	119.9	C33—C34—H34	119.6
Cl1—C4—C3	118.6 (2)	C35—C34—H34	119.6
Cl1—C4—C5	119.7 (2)	C34—C35—C36	119.6 (3)
C3—C4—C5	121.6 (3)	C34—C35—H35	120.2
C4—C5—C6	118.2 (3)	C36—C35—H35	120.2
C4—C5—H5	120.9	C35—C36—C37	120.4 (2)
C6—C5—H5	120.9	C35—C36—H36	119.8
N1—C6—C1	111.9 (2)	C37—C36—H36	119.8
N1—C6—C5	126.4 (3)	C32—C37—C36	120.4 (2)
C1—C6—C5	121.7 (3)	C32—C37—C38	118.5 (2)
O2—C7—C8	123.7 (2)	C36—C37—C38	121.1 (2)
O2—C7—C16	117.2 (2)	C37—C38—C39	123.0 (2)
C8—C7—C16	119.1 (2)	C37—C38—H38	118.5
N2—C8—C7	125.1 (3)	C39—C38—H38	118.5
N2—C8—C9	114.7 (2)	C30—C39—C38	119.9 (2)
C7—C8—C9	120.1 (2)	C30—C39—C40	123.8 (2)
C8—C9—C10	122.9 (3)	C38—C39—C40	116.3 (2)
C8—C9—C14	118.6 (3)	O6—C40—N6	122.3 (2)
C10—C9—C14	118.5 (3)	O6—C40—C39	119.0 (2)
C9—C10—C11	120.2 (3)	N6—C40—C39	118.7 (2)
C9—C10—H4	119.9	N6—C41—C42	121.9 (3)
C11—C10—H4	119.9	N6—C41—C46	118.3 (2)
C10—C11—C12	121.4 (3)	C42—C41—C46	119.7 (2)
C10—C11—H11	119.3	C41—C42—C43	119.6 (3)
C12—C11—H11	119.3	C41—C42—H42	120.2
C11—C12—C13	119.4 (3)	C43—C42—H42	120.2
C11—C12—H12	120.3	C42—C43—C44	120.6 (2)
C13—C12—H12	120.3	C42—C43—H43	119.7
C12—C13—C14	120.8 (3)	C44—C43—H43	119.7
C12—C13—H13	119.6	C43—C44—C45	120.0 (3)
C14—C13—H13	119.6	C43—C44—H44	120.0
C9—C14—C13	119.7 (3)	C45—C44—H44	120.0
C9—C14—C15	119.4 (3)	C44—C45—C46	119.7 (3)
C13—C14—C15	120.9 (3)	C44—C45—H45	120.2
C14—C15—C16	122.7 (3)	C46—C45—H45	120.2
C14—C15—H15	118.6	C41—C46—C45	120.5 (2)
C16—C15—H15	118.7	C41—C46—H46	119.8
C7—C16—C15	119.4 (3)	C45—C46—H46	119.7
C7—C16—C17	123.5 (3)	O7—C47—H47A	109.5
C15—C16—C17	116.7 (3)	O7—C47—H47B	109.5
O3—C17—N3	122.3 (3)	O7—C47—H47C	109.5
O3—C17—C16	120.0 (2)	H47A—C47—H47B	109.5
N3—C17—C16	117.7 (2)	H47A—C47—H47C	109.5
N3—C18—C19	124.2 (3)	H47B—C47—H47C	109.5
O1—Fe1—O4—C24	−97.4 (2)	C16—C7—C8—C9	9.6 (4)
O4—Fe1—O1—C1	−84.39 (17)	N2—C8—C9—C10	−7.5 (4)
O1—Fe1—O5—C30	116.4 (2)	N2—C8—C9—C14	172.0 (2)
O5—Fe1—O1—C1	97.96 (17)	C7—C8—C9—C10	174.9 (2)
O1—Fe1—N1—N2	169.2 (2)	C7—C8—C9—C14	−5.7 (4)
O1—Fe1—N1—C6	−9.71 (17)	C8—C9—C10—C11	179.3 (2)
N1—Fe1—O1—C1	8.64 (17)	C8—C9—C14—C13	−179.3 (2)
O1—Fe1—N4—N5	−103.0 (2)	C8—C9—C14—C15	−1.2 (4)
O1—Fe1—N4—C29	85.6 (2)	C10—C9—C14—C13	0.2 (3)
N4—Fe1—O1—C1	−170.06 (17)	C10—C9—C14—C15	178.2 (2)
O2—Fe1—O4—C24	85.2 (2)	C14—C9—C10—C11	−0.1 (3)
O4—Fe1—O2—C7	122.3 (2)	C9—C10—C11—C12	−0.4 (4)
O2—Fe1—O5—C30	−66.2 (2)	C10—C11—C12—C13	0.8 (4)
O5—Fe1—O2—C7	−60.0 (2)	C11—C12—C13—C14	−0.7 (4)
O2—Fe1—N1—N2	−11.9 (2)	C12—C13—C14—C9	0.3 (4)
O2—Fe1—N1—C6	169.19 (18)	C12—C13—C14—C15	−177.8 (2)
N1—Fe1—O2—C7	29.5 (2)	C9—C14—C15—C16	4.2 (4)
O2—Fe1—N4—N5	78.2 (2)	C13—C14—C15—C16	−177.7 (2)
O2—Fe1—N4—C29	−93.2 (2)	C14—C15—C16—C7	−0.2 (4)
N4—Fe1—O2—C7	−151.8 (2)	C14—C15—C16—C17	−173.7 (2)
O4—Fe1—N1—N2	−104.3 (2)	C7—C16—C17—O3	−147.9 (3)
O4—Fe1—N1—C6	76.83 (18)	C7—C16—C17—N3	32.0 (4)
N1—Fe1—O4—C24	177.4 (2)	C15—C16—C17—O3	25.2 (4)
O4—Fe1—N4—N5	170.6 (3)	C15—C16—C17—N3	−154.8 (2)
O4—Fe1—N4—C29	−0.8 (2)	N3—C18—C19—C20	179.4 (3)
N4—Fe1—O4—C24	−2.0 (2)	N3—C18—C23—C22	179.5 (2)
O5—Fe1—N1—N2	77.3 (2)	C19—C18—C23—C22	−0.3 (4)
O5—Fe1—N1—C6	−101.57 (18)	C23—C18—C19—C20	−0.8 (5)
N1—Fe1—O5—C30	−158.4 (2)	C18—C19—C20—C21	1.4 (5)
O5—Fe1—N4—N5	−11.0 (2)	C19—C20—C21—C22	−1.0 (5)
O5—Fe1—N4—C29	177.6 (2)	C20—C21—C22—C23	−0.2 (4)
N4—Fe1—O5—C30	21.1 (2)	C21—C22—C23—C18	0.8 (5)
Fe1—O1—C1—C2	174.4 (2)	O4—C24—C25—C26	179.5 (3)
Fe1—O1—C1—C6	−6.0 (2)	O4—C24—C29—N4	−5.3 (4)
Fe1—O2—C7—C8	−33.9 (3)	O4—C24—C29—C28	−179.0 (3)
Fe1—O2—C7—C16	145.1 (2)	C25—C24—C29—N4	174.3 (2)
Fe1—O4—C24—C25	−175.0 (2)	C25—C24—C29—C28	0.7 (5)
Fe1—O4—C24—C29	4.6 (3)	C29—C24—C25—C26	−0.1 (3)
Fe1—O5—C30—C31	−22.4 (4)	C24—C25—C26—C27	−1.0 (5)
Fe1—O5—C30—C39	157.5 (2)	C25—C26—C27—Cl2	−176.5 (2)
Fe1—N1—N2—C8	−4.6 (3)	C25—C26—C27—C28	1.7 (5)
Fe1—N1—C6—C1	8.8 (2)	Cl2—C27—C28—C29	177.1 (2)
Fe1—N1—C6—C5	−173.3 (2)	C26—C27—C28—C29	−1.1 (5)
N2—N1—C6—C1	−170.2 (2)	C27—C28—C29—N4	−172.8 (3)
N2—N1—C6—C5	7.6 (3)	C27—C28—C29—C24	−0.1 (4)
C6—N1—N2—C8	174.2 (2)	O5—C30—C31—N5	6.4 (5)
N1—N2—C8—C7	9.4 (4)	O5—C30—C31—C32	−175.2 (3)
N1—N2—C8—C9	−168.1 (2)	O5—C30—C39—C38	173.7 (3)
C17—N3—C18—C19	−11.5 (5)	O5—C30—C39—C40	−7.7 (4)
C17—N3—C18—C23	168.7 (3)	C31—C30—C39—C38	−6.4 (4)
C18—N3—C17—O3	4.1 (5)	C31—C30—C39—C40	172.3 (3)
C18—N3—C17—C16	−175.8 (3)	C39—C30—C31—N5	−173.5 (3)
Fe1—N4—N5—C31	0.2 (4)	C39—C30—C31—C32	4.8 (4)
Fe1—N4—C29—C24	3.3 (3)	N5—C31—C32—C33	−1.3 (4)
Fe1—N4—C29—C28	176.7 (2)	N5—C31—C32—C37	179.2 (2)
N5—N4—C29—C24	−169.6 (2)	C30—C31—C32—C33	−179.8 (3)
N5—N4—C29—C28	3.9 (4)	C30—C31—C32—C37	0.7 (4)
C29—N4—N5—C31	171.3 (2)	C31—C32—C33—C34	−177.8 (3)
N4—N5—C31—C30	5.5 (4)	C31—C32—C37—C36	176.5 (3)
N4—N5—C31—C32	−173.0 (2)	C31—C32—C37—C38	−4.6 (4)
C40—N6—C41—C42	−30.6 (5)	C33—C32—C37—C36	−3.1 (4)
C40—N6—C41—C46	153.1 (3)	C33—C32—C37—C38	175.9 (3)
C41—N6—C40—O6	−5.5 (5)	C37—C32—C33—C34	1.8 (5)
C41—N6—C40—C39	175.9 (3)	C32—C33—C34—C35	0.9 (5)
O1—C1—C2—C3	−178.7 (2)	C33—C34—C35—C36	−2.3 (5)
O1—C1—C6—N1	−1.8 (3)	C34—C35—C36—C37	0.9 (5)
O1—C1—C6—C5	−179.8 (2)	C35—C36—C37—C32	1.7 (5)
C2—C1—C6—N1	177.8 (2)	C35—C36—C37—C38	−177.1 (3)
C2—C1—C6—C5	−0.1 (3)	C32—C37—C38—C39	3.1 (5)
C6—C1—C2—C3	1.6 (3)	C36—C37—C38—C39	−178.0 (3)
C1—C2—C3—C4	−1.8 (4)	C37—C38—C39—C30	2.5 (5)
C2—C3—C4—Cl1	178.2 (2)	C37—C38—C39—C40	−176.2 (3)
C2—C3—C4—C5	0.5 (4)	C30—C39—C40—O6	−160.4 (3)
Cl1—C4—C5—C6	−176.7 (2)	C30—C39—C40—N6	18.2 (4)
C3—C4—C5—C6	1.0 (4)	C38—C39—C40—O6	18.3 (4)
C4—C5—C6—N1	−178.8 (2)	C38—C39—C40—N6	−163.1 (3)
C4—C5—C6—C1	−1.2 (4)	N6—C41—C42—C43	−177.1 (3)
O2—C7—C8—N2	11.1 (4)	N6—C41—C46—C45	177.5 (3)
O2—C7—C8—C9	−171.5 (2)	C42—C41—C46—C45	1.1 (5)
O2—C7—C16—C15	174.3 (2)	C46—C41—C42—C43	−0.8 (5)
O2—C7—C16—C17	−12.8 (4)	C41—C42—C43—C44	−0.2 (4)
C8—C7—C16—C15	−6.7 (4)	C42—C43—C44—C45	0.9 (6)
C8—C7—C16—C17	166.2 (2)	C43—C44—C45—C46	−0.6 (6)
C16—C7—C8—N2	−167.8 (2)	C44—C45—C46—C41	−0.4 (5)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H1A···O1	1.063	1.687	2.747 (3)	174.2
N7—H1B···O6^iv	0.953	1.957	2.910 (3)	177.8
N7—H1C···O7	0.919	1.835	2.748 (4)	172.6
N7—H1D···O3^iv	0.844	1.916	2.753 (3)	171.0
O7—H7O···O6^i	0.84	1.89	2.709 (3)	166
N3—H3N···O2	0.88	2.09	2.675 (3)	124
N6—H6N···O5	0.88	1.95	2.653 (2)	136

Symmetry codes: (i) −x+1, −y+1, −z+1; (iv) x−1, y, z.