Download citation
Download citation
link to html
The title compound, (NH4)[Fe(C23H24ClN3O3)2]·C3H6O, is a charge-control agent used in electrophotography. The central FeIII atom is coordinated by four O atoms and two N atoms of two symmetry-independent ligands. The metallic complex has no crystallographic symmetry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807016571/sa2047sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807016571/sa2047Isup2.hkl
Contains datablock I

CCDC reference: 647319

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.089
  • wR factor = 0.257
  • Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found




Alert level B RINTA01_ALERT_3_B The value of Rint is greater than 0.15 Rint given 0.196 PLAT020_ALERT_3_B The value of Rint is greater than 0.10 ......... 0.20
Alert level C RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.257 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT084_ALERT_2_C High R2 Value .................................. 0.26 PLAT230_ALERT_2_C Hirshfeld Test Diff for O6 - C28 .. 5.89 su PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT352_ALERT_3_C Short N-H Bond (0.87A) N7 - H1A ... 0.71 Ang. PLAT353_ALERT_3_C Long N-H Bond (0.87A) N7 - H1B ... 1.01 Ang. PLAT353_ALERT_3_C Long N-H Bond (0.87A) N7 - H1D ... 1.01 Ang. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 33 N3 -FE1 -N1 -C40 33.00 18.00 1.555 1.555 1.555 1.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 H4 N
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 7 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

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) acetone solvate top
Crystal data top
(NH4N)[Fe(C23H24ClN3O3)2]·C3H6OF(000) = 1988.00
Mr = 963.61Dx = 1.480 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ynCell parameters from 25840 reflections
a = 11.3199 (14) Åθ = 3.4–26.1°
b = 13.7962 (17) ŵ = 0.54 mm1
c = 27.757 (4) ÅT = 100 K
β = 93.747 (3)°Platelet, black
V = 4325.6 (10) Å30.10 × 0.10 × 0.04 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4761 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.196
ω scansθmax = 26.0°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1313
Tmin = 0.950, Tmax = 0.979k = 1616
53581 measured reflectionsl = 3434
8466 independent reflections
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.089 w = 1/[σ2(Fo2) + (0.1296P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.257(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.98 e Å3
8466 reflectionsΔρmin = 0.61 e Å3
612 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
Fe10.21487 (7)0.76853 (5)0.51841 (3)0.0398 (2)
Cl10.02245 (15)0.95536 (11)0.30403 (6)0.0569 (4)
Cl20.08330 (15)0.74126 (12)0.72061 (6)0.0581 (4)
O10.0497 (3)0.7323 (2)0.51960 (13)0.0429 (8)
O20.1578 (3)0.8980 (2)0.50934 (14)0.0448 (9)
O30.3729 (3)0.8127 (2)0.52097 (13)0.0407 (8)
O40.2634 (3)0.6372 (2)0.52365 (13)0.0408 (8)
O50.7199 (3)0.8882 (2)0.50362 (15)0.0522 (10)
O60.3147 (3)0.3443 (2)0.54840 (15)0.0513 (10)
O70.0200 (4)0.6631 (3)0.37983 (18)0.0667 (12)
N10.2126 (3)0.7740 (2)0.58653 (17)0.0395 (10)
N20.2937 (4)0.7919 (3)0.61973 (16)0.0435 (11)
N30.2156 (3)0.7635 (3)0.45023 (17)0.0411 (10)
N40.2564 (4)0.7018 (3)0.42215 (17)0.0454 (11)
N50.3146 (4)0.4919 (3)0.58535 (16)0.0431 (10)
N60.5355 (4)0.8866 (3)0.46648 (17)0.0453 (11)
N70.1252 (5)0.7851 (4)0.4485 (2)0.0517 (13)
C10.4042 (4)0.8177 (3)0.6074 (2)0.0398 (12)
C20.4846 (4)0.8373 (3)0.6490 (2)0.0414 (12)
C30.4548 (5)0.8188 (4)0.6964 (2)0.0468 (13)
C40.5314 (5)0.8385 (4)0.7346 (2)0.0524 (14)
C50.6436 (5)0.8788 (4)0.7276 (2)0.0601 (17)
C60.6762 (5)0.8969 (4)0.6817 (2)0.0573 (16)
C70.6005 (5)0.8744 (4)0.6414 (2)0.0487 (14)
C80.6326 (5)0.8864 (3)0.5937 (2)0.0445 (13)
C90.5598 (5)0.8655 (3)0.5538 (2)0.0438 (13)
C100.4407 (4)0.8296 (3)0.55976 (19)0.0392 (12)
C110.6119 (5)0.8801 (3)0.5057 (2)0.0432 (13)
C120.5607 (5)0.8979 (3)0.4178 (2)0.0460 (13)
C130.6630 (5)0.9446 (3)0.4037 (2)0.0513 (14)
C140.6792 (5)0.9540 (4)0.3549 (2)0.0562 (16)
C150.5965 (6)0.9203 (4)0.3202 (2)0.0582 (16)
C160.4934 (6)0.8756 (4)0.3343 (2)0.0609 (16)
C170.4779 (6)0.8644 (4)0.3832 (2)0.0555 (15)
C180.2984 (4)0.5827 (3)0.4880 (2)0.0415 (12)
C190.3014 (4)0.6160 (3)0.43994 (19)0.0414 (12)
C200.3453 (4)0.5542 (3)0.4029 (2)0.0419 (12)
C210.3551 (5)0.5861 (4)0.3547 (2)0.0461 (13)
C220.3919 (5)0.5231 (4)0.3200 (2)0.0499 (14)
C230.4213 (5)0.4262 (4)0.3316 (2)0.0482 (14)
C240.4145 (5)0.3954 (4)0.3782 (2)0.0462 (13)
C250.3776 (4)0.4568 (3)0.4146 (2)0.0428 (12)
C260.3677 (4)0.4253 (3)0.4624 (2)0.0453 (13)
C270.3296 (4)0.4830 (3)0.4983 (2)0.0414 (12)
C280.3183 (5)0.4339 (4)0.5463 (2)0.0481 (13)
C290.3066 (5)0.4661 (3)0.6341 (2)0.0452 (13)
C300.2867 (5)0.5422 (4)0.6658 (2)0.0492 (14)
C310.2818 (5)0.5240 (4)0.7147 (2)0.0541 (15)
C320.2930 (5)0.4305 (4)0.7322 (2)0.0571 (15)
C330.3118 (5)0.3560 (4)0.7010 (2)0.0567 (16)
C340.3203 (5)0.3720 (4)0.6520 (2)0.0528 (15)
C350.0151 (5)0.7351 (3)0.5646 (2)0.0403 (12)
C360.1033 (5)0.7211 (3)0.5766 (2)0.0436 (13)
C370.1330 (5)0.7247 (3)0.6237 (2)0.0467 (13)
C380.0453 (5)0.7420 (3)0.6607 (2)0.0453 (13)
C390.0703 (5)0.7571 (3)0.6506 (2)0.0421 (12)
C400.0983 (5)0.7546 (3)0.6029 (2)0.0406 (12)
C410.1309 (5)0.9149 (3)0.4636 (2)0.0429 (12)
C420.1586 (5)0.8474 (3)0.4282 (2)0.0439 (13)
C430.1296 (5)0.8569 (3)0.3799 (2)0.0460 (13)
C440.0683 (5)0.9396 (3)0.3643 (2)0.0487 (14)
C450.0401 (5)1.0105 (3)0.3977 (2)0.0466 (13)
C460.0710 (5)0.9996 (4)0.4461 (2)0.0466 (13)
C470.0053 (6)0.5341 (4)0.4368 (2)0.0602 (16)
C480.0015 (5)0.5781 (4)0.3870 (2)0.0556 (15)
C490.0257 (6)0.5100 (4)0.3469 (2)0.0619 (17)
H30.37950.79190.70180.056*
H40.50960.82510.76640.063*
H50.69650.89350.75460.072*
H5N0.31760.55450.57950.052*
H60.75120.92500.67720.069*
H6N0.45990.88330.47200.054*
H1A0.105 (6)0.779 (4)0.425 (2)0.05 (2)*
H1B0.155 (6)0.852 (5)0.456 (2)0.08 (2)*
H1C0.178 (7)0.730 (6)0.444 (2)0.09 (2)*
H1D0.060 (6)0.772 (4)0.474 (2)0.060 (18)*
H80.70960.91050.58890.053*
H130.72000.96930.42710.062*
H140.74890.98450.34510.067*
H150.60950.92740.28690.070*
H160.43500.85310.31080.073*
H170.40870.83300.39300.067*
H210.33620.65130.34620.055*
H220.39750.54540.28780.060*
H230.44540.38300.30740.058*
H240.43530.33040.38610.055*
H260.38870.36020.47010.054*
H300.27650.60630.65390.059*
H310.27070.57610.73630.065*
H320.28780.41810.76570.069*
H330.31920.29180.71330.068*
H340.33520.31970.63090.063*
H360.16310.70890.55170.052*
H370.21290.71540.63120.056*
H390.12950.76900.67570.050*
H430.15060.80850.35760.055*
H450.00121.06720.38680.056*
H460.05211.04910.46810.056*
H47a0.01850.46590.43440.072*
H47b0.04910.56930.45660.072*
H47c0.08590.53860.45180.072*
H49a0.07950.45870.35930.074*
H49b0.06240.54560.32120.074*
H49c0.04880.48100.33400.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0430 (4)0.0347 (4)0.0413 (5)0.0017 (3)0.0002 (3)0.0001 (3)
Cl10.0720 (10)0.0500 (8)0.0482 (9)0.0031 (7)0.0002 (7)0.0039 (6)
Cl20.0585 (9)0.0720 (10)0.0445 (9)0.0039 (7)0.0099 (7)0.0074 (6)
O10.047 (2)0.042 (2)0.039 (2)0.0005 (16)0.0009 (17)0.0018 (15)
O20.051 (2)0.0334 (19)0.049 (2)0.0024 (16)0.0042 (18)0.0010 (16)
O30.044 (2)0.0383 (19)0.040 (2)0.0011 (16)0.0017 (17)0.0006 (15)
O40.046 (2)0.0367 (19)0.040 (2)0.0029 (16)0.0012 (16)0.0008 (15)
O50.044 (2)0.058 (2)0.055 (2)0.0071 (18)0.0059 (19)0.0035 (18)
O60.056 (2)0.034 (2)0.063 (2)0.0034 (18)0.002 (2)0.0009 (17)
O70.055 (2)0.043 (2)0.100 (3)0.000 (2)0.000 (2)0.002 (2)
N10.036 (2)0.034 (2)0.048 (2)0.0036 (18)0.003 (2)0.0006 (19)
N20.051 (3)0.035 (2)0.044 (2)0.003 (2)0.002 (2)0.0029 (19)
N30.036 (2)0.041 (2)0.046 (2)0.0035 (19)0.004 (2)0.001 (2)
N40.045 (2)0.039 (2)0.052 (2)0.002 (2)0.002 (2)0.003 (2)
N50.046 (2)0.037 (2)0.046 (2)0.003 (2)0.001 (2)0.002 (2)
N60.036 (2)0.049 (2)0.052 (3)0.003 (2)0.008 (2)0.000 (2)
N70.052 (3)0.060 (3)0.043 (3)0.001 (2)0.004 (3)0.006 (2)
C10.041 (3)0.027 (2)0.052 (3)0.004 (2)0.002 (2)0.002 (2)
C20.043 (3)0.035 (2)0.046 (3)0.006 (2)0.002 (2)0.004 (2)
C30.050 (3)0.044 (3)0.046 (3)0.009 (2)0.001 (2)0.005 (2)
C40.051 (3)0.062 (3)0.045 (3)0.005 (2)0.005 (2)0.010 (2)
C50.056 (4)0.071 (4)0.052 (4)0.001 (3)0.012 (3)0.015 (3)
C60.053 (3)0.063 (3)0.056 (4)0.000 (3)0.003 (3)0.016 (3)
C70.048 (3)0.047 (3)0.051 (3)0.006 (2)0.002 (2)0.009 (2)
C80.037 (3)0.041 (3)0.056 (3)0.003 (2)0.009 (2)0.004 (2)
C90.049 (3)0.035 (2)0.047 (3)0.007 (2)0.001 (2)0.003 (2)
C100.043 (3)0.033 (2)0.042 (3)0.004 (2)0.007 (2)0.003 (2)
C110.048 (3)0.031 (2)0.051 (3)0.002 (2)0.003 (2)0.000 (2)
C120.054 (3)0.039 (2)0.046 (3)0.008 (2)0.006 (2)0.002 (2)
C130.062 (4)0.040 (3)0.053 (3)0.005 (2)0.009 (3)0.003 (2)
C140.055 (3)0.050 (3)0.065 (4)0.008 (2)0.015 (3)0.004 (2)
C150.072 (4)0.048 (3)0.057 (4)0.008 (3)0.022 (3)0.003 (2)
C160.077 (4)0.054 (3)0.051 (3)0.003 (3)0.004 (3)0.007 (2)
C170.062 (4)0.053 (3)0.052 (3)0.004 (3)0.011 (3)0.002 (2)
C180.035 (2)0.043 (3)0.046 (3)0.005 (2)0.002 (2)0.004 (2)
C190.043 (3)0.038 (2)0.043 (3)0.003 (2)0.001 (2)0.000 (2)
C200.036 (2)0.043 (3)0.046 (3)0.001 (2)0.001 (2)0.004 (2)
C210.045 (3)0.047 (3)0.045 (3)0.005 (2)0.001 (2)0.001 (2)
C220.050 (3)0.053 (3)0.046 (3)0.001 (2)0.002 (2)0.004 (2)
C230.042 (3)0.047 (3)0.055 (3)0.004 (2)0.004 (2)0.015 (2)
C240.042 (3)0.041 (3)0.056 (3)0.001 (2)0.002 (2)0.004 (2)
C250.041 (3)0.039 (2)0.048 (3)0.004 (2)0.001 (2)0.005 (2)
C260.034 (3)0.039 (2)0.062 (3)0.002 (2)0.001 (2)0.002 (2)
C270.040 (3)0.037 (2)0.047 (3)0.004 (2)0.001 (2)0.001 (2)
C280.039 (3)0.055 (3)0.050 (3)0.000 (2)0.002 (2)0.000 (2)
C290.041 (3)0.043 (3)0.051 (3)0.004 (2)0.004 (2)0.002 (2)
C300.045 (3)0.048 (3)0.055 (3)0.002 (2)0.006 (2)0.006 (2)
C310.044 (3)0.059 (3)0.060 (4)0.002 (2)0.010 (2)0.000 (2)
C320.060 (4)0.059 (3)0.053 (3)0.006 (3)0.004 (3)0.008 (3)
C330.057 (3)0.048 (3)0.064 (4)0.005 (2)0.008 (3)0.014 (2)
C340.060 (3)0.043 (3)0.054 (3)0.004 (2)0.007 (3)0.005 (2)
C350.046 (3)0.030 (2)0.044 (3)0.001 (2)0.002 (2)0.002 (2)
C360.040 (3)0.038 (2)0.052 (3)0.005 (2)0.003 (2)0.002 (2)
C370.051 (3)0.039 (2)0.050 (3)0.001 (2)0.008 (2)0.003 (2)
C380.057 (3)0.040 (2)0.039 (3)0.004 (2)0.009 (2)0.004 (2)
C390.048 (3)0.033 (2)0.044 (3)0.002 (2)0.001 (2)0.002 (2)
C400.043 (3)0.031 (2)0.047 (3)0.005 (2)0.000 (2)0.001 (2)
C410.047 (3)0.037 (2)0.044 (3)0.002 (2)0.001 (2)0.000 (2)
C420.045 (3)0.043 (3)0.044 (3)0.003 (2)0.002 (2)0.006 (2)
C430.048 (3)0.036 (2)0.055 (3)0.001 (2)0.008 (2)0.003 (2)
C440.052 (3)0.040 (3)0.054 (3)0.003 (2)0.001 (2)0.003 (2)
C450.048 (3)0.037 (2)0.055 (3)0.004 (2)0.005 (2)0.006 (2)
C460.045 (3)0.043 (3)0.052 (3)0.000 (2)0.004 (2)0.002 (2)
C470.056 (3)0.059 (3)0.066 (4)0.005 (3)0.005 (3)0.009 (3)
C480.047 (3)0.044 (3)0.075 (4)0.003 (2)0.001 (3)0.002 (3)
C490.066 (4)0.052 (3)0.068 (4)0.003 (3)0.007 (3)0.007 (3)
Geometric parameters (Å, º) top
Fe1—O11.937 (3)C16—H160.95
Fe1—O21.910 (3)C17—H170.95
Fe1—O31.887 (3)C18—C191.414 (7)
Fe1—O41.896 (3)C18—C271.444 (7)
Fe1—N11.894 (4)C19—C201.448 (7)
Fe1—N31.894 (4)C20—C211.421 (7)
Cl1—C441.734 (6)C20—C251.423 (7)
Cl2—C381.745 (5)C21—C221.382 (8)
O1—C351.333 (6)C21—H210.95
O2—C411.307 (6)C22—C231.409 (8)
O3—C101.302 (6)C22—H220.95
O4—C181.323 (6)C23—C241.369 (8)
O5—C111.233 (7)C23—H230.95
O6—C281.238 (6)C24—C251.402 (8)
O7—C481.212 (7)C24—H240.95
N1—N21.282 (6)C25—C261.409 (8)
N1—C401.425 (7)C26—C271.368 (8)
N2—C11.366 (7)C26—H260.95
N3—N41.262 (6)C27—C281.507 (8)
N3—C421.441 (6)C29—C301.398 (8)
N4—C191.368 (6)C29—C341.395 (7)
N5—C281.350 (7)C30—C311.384 (8)
N5—C291.407 (7)C30—H300.95
N5—H5N0.88C31—C321.381 (8)
N6—C111.349 (7)C31—H310.95
N6—C121.407 (7)C32—C331.370 (9)
N6—H6N0.88C32—H320.95
N7—H1A0.70 (7)C33—C341.389 (9)
N7—H1B1.00 (7)C33—H330.95
N7—H1C0.97 (8)C34—H340.95
N7—H1D1.01 (6)C35—C361.416 (8)
C1—C21.448 (7)C35—C401.400 (7)
C1—C101.420 (7)C36—C371.371 (8)
C2—C31.404 (8)C36—H360.95
C2—C71.437 (8)C37—C381.402 (8)
C3—C41.354 (8)C37—H370.95
C3—H30.95C38—C391.371 (8)
C4—C51.412 (9)C39—C401.381 (8)
C4—H40.95C39—H390.95
C5—C61.373 (9)C41—C421.403 (7)
C5—H50.95C41—C461.419 (7)
C6—C71.398 (8)C42—C431.367 (7)
C6—H60.95C43—C441.389 (7)
C7—C81.404 (8)C43—H430.95
C8—C91.368 (7)C44—C451.399 (8)
C8—H80.95C45—C461.375 (8)
C9—C101.456 (8)C45—H450.95
C9—C111.507 (8)C46—H460.95
C12—C131.404 (8)C47—C481.508 (9)
C12—C171.377 (8)C47—H47a0.98
C13—C141.382 (9)C47—H47b0.98
C13—H130.95C47—H47c0.98
C14—C151.380 (9)C48—C491.496 (8)
C14—H140.95C49—H49a0.98
C15—C161.398 (10)C49—H49b0.98
C15—H150.95C49—H49c0.98
C16—C171.389 (9)
O1···H1D1.80 (6)H1C···H47b2.66
O2···H46i2.601H1D···O11.80 (6)
O5···N7ii2.791 (7)H1D···C352.65 (6)
O5···H1Bii2.06 (7)H1D···H362.66
O5···H46iii2.785H13···H1Bii2.26
O6···N7iv2.797 (7)H14···H32ix2.644
O6···H1Civ1.87 (8)H15···H31ix2.376
O7···H1A2.28 (6)H22···H5x2.543
O7···H1C2.76 (8)H24···C1vi2.730
N7···O5v2.791 (7)H24···C2vi2.691
N7···O6iv2.797 (7)H24···H37iv2.610
C1···H24vi2.731H26···H36iv2.757
C2···H24vi2.691H31···H15xi2.376
C13···H1Bii2.76 (7)H32···H3xii2.767
C18···H47c2.617H32···H14xi2.644
C19···H47c2.702H32···H39xii2.748
C24···H37iv2.744H34···H1Civ2.73
C28···H1Civ2.78 (8)H36···H1D2.660
C30···H49civ2.713H36···H26iv2.757
C35···H1D2.65 (6)H37···C24iv2.744
C35···H47aiv2.774H37···H24iv2.610
C37···H49aiv2.637H39···H32vii2.748
C39···H45i2.731H45···C39i2.731
C40···H45i2.717H45···C40i2.717
H3···H32vii2.767H46···O2i2.601
H4···H49bviii2.395H46···O5iii2.785
H5···H22viii2.543H46···H1Bi2.71
H5···H49bviii2.607H46···H46i2.575
H1A···O72.28 (6)H47a···C35iv2.774
H1B···O5v2.06 (7)H47b···H1C2.66
H1B···C13v2.76 (7)H47c···C182.617
H1B···H13v2.26H47c···C192.702
H1B···H46i2.71H49a···C37iv2.637
H1C···O6iv1.87 (8)H49b···H4x2.395
H1C···O72.76 (8)H49b···H5x2.607
H1C···C28iv2.78 (8)H49c···C30iv2.713
H1C···H34iv2.73
O1—Fe1—O285.69 (15)C19—C20—C21122.5 (4)
O1—Fe1—O3174.98 (15)C19—C20—C25119.3 (4)
O1—Fe1—O491.57 (15)C21—C20—C25118.1 (5)
O1—Fe1—N185.24 (17)C20—C21—C22120.5 (5)
O1—Fe1—N394.30 (17)C20—C21—H21119.7
O2—Fe1—O390.83 (15)C22—C21—H21119.8
O2—Fe1—O4175.77 (15)C21—C22—C23121.0 (5)
O2—Fe1—N193.88 (17)C21—C22—H22119.5
O2—Fe1—N385.76 (17)C23—C22—H22119.5
O3—Fe1—O492.10 (15)C22—C23—C24118.9 (5)
O3—Fe1—N191.39 (17)C22—C23—H23120.5
O3—Fe1—N389.04 (17)C24—C23—H23120.5
O4—Fe1—N189.10 (16)C23—C24—C25122.0 (5)
O4—Fe1—N391.24 (17)C23—C24—H24119.0
N1—Fe1—N3179.44 (19)C25—C24—H24119.0
Fe1—O1—C35110.6 (3)C20—C25—C24119.4 (5)
Fe1—O2—C41110.5 (3)C20—C25—C26118.1 (4)
Fe1—O3—C10126.5 (3)C24—C25—C26122.5 (4)
Fe1—O4—C18125.8 (3)C25—C26—C27123.8 (5)
Fe1—N1—N2132.0 (3)C25—C26—H26118.1
Fe1—N1—C40112.5 (3)C27—C26—H26118.1
N2—N1—C40115.4 (4)C18—C27—C26119.6 (5)
N1—N2—C1119.6 (4)C18—C27—C28124.7 (4)
Fe1—N3—N4131.9 (3)C26—C27—C28115.6 (4)
Fe1—N3—C42111.3 (3)O6—C28—N5123.5 (5)
N4—N3—C42116.9 (4)O6—C28—C27119.7 (5)
N3—N4—C19120.2 (4)N5—C28—C27116.9 (4)
C28—N5—C29129.0 (4)N5—C29—C30116.1 (4)
C28—N5—H5N115.5N5—C29—C34124.4 (5)
C29—N5—H5N115.5C30—C29—C34119.5 (5)
C11—N6—C12128.5 (4)C29—C30—C31120.0 (5)
C11—N6—H6N115.7C29—C30—H30120.0
C12—N6—H6N115.7C31—C30—H30120.0
H1A—N7—H1B116 (6)C30—C31—C32120.4 (5)
H1A—N7—H1C91 (7)C30—C31—H31119.8
H1A—N7—H1D112 (6)C32—C31—H31119.8
H1B—N7—H1C122 (6)C31—C32—C33119.5 (6)
H1B—N7—H1D105 (5)C31—C32—H32120.2
H1C—N7—H1D112 (5)C33—C32—H32120.2
N2—C1—C2112.7 (4)C32—C33—C34121.6 (5)
N2—C1—C10126.2 (4)C32—C33—H33119.2
C2—C1—C10121.0 (4)C34—C33—H33119.2
C1—C2—C3122.5 (5)C29—C34—C33119.0 (5)
C1—C2—C7118.8 (5)C29—C34—H34120.5
C3—C2—C7118.7 (5)C33—C34—H34120.5
C2—C3—C4121.2 (5)O1—C35—C36123.9 (4)
C2—C3—H3119.4O1—C35—C40119.6 (5)
C4—C3—H3119.4C36—C35—C40116.5 (5)
C3—C4—C5120.5 (5)C35—C36—C37121.0 (5)
C3—C4—H4119.8C35—C36—H36119.5
C5—C4—H4119.8C37—C36—H36119.5
C4—C5—C6119.9 (5)C36—C37—C38119.9 (5)
C4—C5—H5120.1C36—C37—H37120.0
C6—C5—H5120.1C38—C37—H37120.1
C5—C6—C7121.0 (6)Cl2—C38—C37119.4 (4)
C5—C6—H6119.5Cl2—C38—C39119.6 (4)
C7—C6—H6119.5C37—C38—C39121.0 (5)
C2—C7—C6118.6 (5)C38—C39—C40118.3 (5)
C2—C7—C8118.4 (5)C38—C39—H39120.9
C6—C7—C8123.0 (5)C40—C39—H39120.9
C7—C8—C9124.0 (5)N1—C40—C35111.9 (4)
C7—C8—H8118.0N1—C40—C39124.9 (4)
C9—C8—H8118.0C35—C40—C39123.3 (5)
C8—C9—C10119.6 (5)O2—C41—C42120.8 (4)
C8—C9—C11116.0 (5)O2—C41—C46123.6 (4)
C10—C9—C11124.4 (4)C42—C41—C46115.5 (4)
O3—C10—C1123.9 (4)N3—C42—C41110.6 (4)
O3—C10—C9117.9 (4)N3—C42—C43124.4 (4)
C1—C10—C9118.2 (4)C41—C42—C43125.0 (5)
O5—C11—N6122.8 (5)C42—C43—C44117.8 (5)
O5—C11—C9120.1 (5)C42—C43—H43121.1
N6—C11—C9117.2 (5)C44—C43—H43121.1
N6—C12—C13122.9 (5)Cl1—C44—C43121.0 (4)
N6—C12—C17117.4 (5)Cl1—C44—C45119.0 (4)
C13—C12—C17119.6 (5)C43—C44—C45120.0 (5)
C12—C13—C14118.8 (5)C44—C45—C46121.0 (5)
C12—C13—H13120.6C44—C45—H45119.5
C14—C13—H13120.6C46—C45—H45119.5
C13—C14—C15121.6 (6)C41—C46—C45120.6 (5)
C13—C14—H14119.2C41—C46—H46119.7
C15—C14—H14119.2C45—C46—H46119.7
C14—C15—C16119.6 (6)C48—C47—H47a109.5
C14—C15—H15120.2C48—C47—H47b109.5
C16—C15—H15120.2C48—C47—H47c109.5
C15—C16—C17119.0 (6)H47a—C47—H47b109.5
C15—C16—H16120.5H47a—C47—H47c109.5
C17—C16—H16120.5H47b—C47—H47c109.5
C12—C17—C16121.4 (6)O7—C48—C47122.3 (6)
C12—C17—H17119.3O7—C48—C49122.0 (6)
C16—C17—H17119.3C47—C48—C49115.7 (5)
O4—C18—C19123.2 (4)C48—C49—H49a109.5
O4—C18—C27118.3 (4)C48—C49—H49b109.5
C19—C18—C27118.4 (4)C48—C49—H49c109.5
N4—C19—C18126.2 (4)H49a—C49—H49b109.5
N4—C19—C20113.0 (4)H49a—C49—H49c109.5
C18—C19—C20120.6 (4)H49b—C49—H49c109.5
O1—Fe1—O2—C4185.4 (3)C6—C7—C8—C9179.5 (5)
O2—Fe1—O1—C3590.3 (3)C7—C8—C9—C100.7 (8)
O1—Fe1—O4—C18103.3 (4)C7—C8—C9—C11178.0 (4)
O4—Fe1—O1—C3592.9 (3)C8—C9—C10—O3178.4 (4)
O1—Fe1—N1—N2177.7 (4)C8—C9—C10—C10.1 (5)
O1—Fe1—N1—C402.5 (3)C8—C9—C11—O516.1 (7)
N1—Fe1—O1—C354.0 (3)C8—C9—C11—N6162.1 (4)
O1—Fe1—N3—N4103.9 (4)C10—C9—C11—O5162.6 (4)
O1—Fe1—N3—C4276.4 (3)C10—C9—C11—N619.2 (7)
N3—Fe1—O1—C35175.7 (3)C11—C9—C10—O33.0 (7)
O2—Fe1—O3—C1097.8 (3)C11—C9—C10—C1178.8 (4)
O3—Fe1—O2—C4198.2 (3)N6—C12—C13—C14178.7 (5)
O2—Fe1—N1—N296.9 (4)N6—C12—C17—C16177.7 (5)
O2—Fe1—N1—C4082.9 (3)C13—C12—C17—C160.2 (7)
N1—Fe1—O2—C41170.3 (3)C17—C12—C13—C141.3 (8)
O2—Fe1—N3—N4170.7 (5)C12—C13—C14—C151.2 (9)
O2—Fe1—N3—C429.0 (3)C13—C14—C15—C160.1 (7)
N3—Fe1—O2—C419.3 (3)C14—C15—C16—C171.3 (9)
O3—Fe1—O4—C1880.1 (4)C15—C16—C17—C121.1 (9)
O4—Fe1—O3—C1085.2 (3)O4—C18—C19—N48.6 (8)
O3—Fe1—N1—N26.0 (4)O4—C18—C19—C20177.4 (4)
O3—Fe1—N1—C40173.8 (3)O4—C18—C27—C26179.1 (4)
N1—Fe1—O3—C103.9 (4)O4—C18—C27—C284.0 (7)
O3—Fe1—N3—N479.8 (4)C19—C18—C27—C263.8 (7)
O3—Fe1—N3—C4299.9 (3)C19—C18—C27—C28173.1 (5)
N3—Fe1—O3—C10176.5 (4)C27—C18—C19—N4168.4 (5)
O4—Fe1—N1—N286.1 (4)C27—C18—C19—C205.6 (7)
O4—Fe1—N1—C4094.1 (3)N4—C19—C20—C218.2 (7)
N1—Fe1—O4—C18171.5 (4)N4—C19—C20—C25170.3 (4)
O4—Fe1—N3—N412.3 (4)C18—C19—C20—C21177.0 (5)
O4—Fe1—N3—C42168.0 (3)C18—C19—C20—C254.5 (7)
N3—Fe1—O4—C189.0 (4)C19—C20—C21—C22176.7 (5)
N3—Fe1—N1—C4033 (18)C19—C20—C25—C24176.8 (5)
Fe1—O1—C35—C36174.0 (3)C19—C20—C25—C261.4 (7)
Fe1—O1—C35—C404.9 (5)C21—C20—C25—C241.8 (7)
Fe1—O2—C41—C427.9 (6)C21—C20—C25—C26179.9 (3)
Fe1—O2—C41—C46170.9 (4)C25—C20—C21—C221.8 (8)
Fe1—O3—C10—C10.6 (6)C20—C21—C22—C230.4 (7)
Fe1—O3—C10—C9178.7 (3)C21—C22—C23—C240.9 (8)
Fe1—O4—C18—C191.5 (7)C22—C23—C24—C250.9 (8)
Fe1—O4—C18—C27178.5 (3)C23—C24—C25—C200.5 (7)
Fe1—N1—N2—C14.2 (6)C23—C24—C25—C26178.5 (5)
Fe1—N1—C40—C350.6 (5)C20—C25—C26—C270.5 (7)
Fe1—N1—C40—C39177.6 (4)C24—C25—C26—C27178.5 (5)
N2—N1—C40—C35179.6 (4)C25—C26—C27—C180.7 (8)
N2—N1—C40—C392.3 (6)C25—C26—C27—C28176.5 (5)
C40—N1—N2—C1175.7 (4)C18—C27—C28—O6159.7 (5)
N1—N2—C1—C2178.8 (4)C18—C27—C28—N521.4 (7)
N1—N2—C1—C101.5 (7)C26—C27—C28—O617.4 (7)
Fe1—N3—N4—C196.7 (7)C26—C27—C28—N5161.5 (5)
Fe1—N3—C42—C417.0 (5)N5—C29—C30—C31177.7 (5)
Fe1—N3—C42—C43169.4 (4)N5—C29—C34—C33179.2 (5)
N4—N3—C42—C41172.7 (4)C30—C29—C34—C331.0 (8)
N4—N3—C42—C4310.8 (7)C34—C29—C30—C310.6 (8)
C42—N3—N4—C19173.6 (4)C29—C30—C31—C321.9 (8)
N3—N4—C19—C186.1 (8)C30—C31—C32—C331.5 (9)
N3—N4—C19—C20179.4 (4)C31—C32—C33—C340.2 (7)
C28—N5—C29—C30170.8 (5)C32—C33—C34—C291.5 (9)
C28—N5—C29—C3411.0 (9)O1—C35—C36—C37179.9 (3)
C29—N5—C28—O60.1 (7)O1—C35—C40—N13.0 (6)
C29—N5—C28—C27178.7 (5)O1—C35—C40—C39178.8 (4)
C11—N6—C12—C1328.3 (8)C36—C35—C40—N1176.0 (4)
C11—N6—C12—C17154.3 (5)C36—C35—C40—C392.2 (7)
C12—N6—C11—O53.4 (8)C40—C35—C36—C371.2 (7)
C12—N6—C11—C9178.4 (4)C35—C36—C37—C380.3 (6)
N2—C1—C2—C37.9 (7)C36—C37—C38—Cl2177.3 (4)
N2—C1—C2—C7174.0 (4)C36—C37—C38—C391.1 (7)
N2—C1—C10—O33.3 (8)Cl2—C38—C39—C40178.2 (3)
N2—C1—C10—C9174.8 (4)C37—C38—C39—C400.2 (5)
C2—C1—C10—O3179.6 (4)C38—C39—C40—N1176.4 (4)
C2—C1—C10—C92.2 (7)C38—C39—C40—C351.5 (7)
C10—C1—C2—C3174.6 (4)O2—C41—C42—N30.7 (7)
C10—C1—C2—C73.4 (7)O2—C41—C42—C43177.1 (5)
C1—C2—C3—C4179.5 (5)O2—C41—C46—C45176.7 (5)
C1—C2—C7—C6177.5 (5)C42—C41—C46—C452.2 (8)
C1—C2—C7—C82.5 (7)C46—C41—C42—N3178.2 (4)
C3—C2—C7—C64.4 (8)C46—C41—C42—C431.8 (8)
C3—C2—C7—C8175.6 (5)N3—C42—C43—C44176.1 (5)
C7—C2—C3—C42.4 (8)C41—C42—C43—C440.2 (6)
C2—C3—C4—C50.3 (7)C42—C43—C44—Cl1177.3 (4)
C3—C4—C5—C61.0 (9)C42—C43—C44—C451.1 (8)
C4—C5—C6—C71.0 (9)Cl1—C44—C45—C46177.8 (4)
C5—C6—C7—C23.7 (9)C43—C44—C45—C460.7 (8)
C5—C6—C7—C8176.3 (5)C44—C45—C46—C411.0 (8)
C2—C7—C8—C90.5 (8)
Symmetry codes: (i) x, y+2, z+1; (ii) x+1, y, z; (iii) x+1, y+2, z+1; (iv) x, y+1, z+1; (v) x1, y, z; (vi) x+1, y+1, z+1; (vii) x+1/2, y+1/2, z+3/2; (viii) x+1/2, y+3/2, z+1/2; (ix) x+1/2, y+3/2, z1/2; (x) x1/2, y+3/2, z1/2; (xi) x1/2, y+3/2, z+1/2; (xii) x+1/2, y1/2, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5N···O40.881.992.675 (5)134
N6—H6N···O30.881.982.661 (6)133
N7—H1A···O70.70 (7)2.28 (6)2.860 (8)140 (6)
N7—H1B···O5v1.00 (7)2.06 (7)2.791 (7)128 (5)
N7—H1C···O6iv0.98 (8)1.87 (8)2.797 (7)156 (7)
N7—H1D···O11.01 (6)1.80 (6)2.800 (7)172 (5)
Symmetry codes: (iv) x, y+1, z+1; (v) x1, y, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds