(S)-3-[(1-Ethoxy­carbonyl-2-phenyl­ethyl)amino]-1-ferrocenylbut-2-en-1-one

The title compound {systematic name: (S)-ethyl 2-[1-(1-ferrocenylcarbon­yl)prop-1-en-2-ylamino]-3-phenyl­propionate}, [Fe(C₅H₅)(C₂₀H₂₂NO₃)], has been synthesized by the reaction of ferrocenoylacetone with ethyl L-phenyl­alanine in ethanol. The two nearly parallel cyclo­penta­dienyl rings in the ferrocenyl moiety adopt an eclipsed conformation.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.012 Å
• R factor = 0.044
• wR factor = 0.121
• Data-to-parameter ratio = 8.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C21

Alert level C
PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro .          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.01
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.09 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.70 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C23
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         Fe
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         12

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           26.00
           From the CIF: _reflns_number_total               2407
           Count of symmetry unique reflns         2458
           Completeness (_total/calc)             97.93%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present        yes

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

   3 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
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003) and OSCAIL-X (McArdle, 1995).

(S)-ethyl 2-[1-(1-ferrocenylcarbonyl)prop-1-en-2-ylamino]-3-phenylpropionate

Crystal data

[Fe(C5H5)(C20H22NO3)]	F(000) = 468
Mr = 445.33	Dx = 1.283 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.029 (2) Å	Cell parameters from 25 reflections
b = 7.4860 (15) Å	θ = 10–13°
c = 15.608 (3) Å	µ = 0.68 mm^−1
β = 100.26 (3)°	T = 293 K
V = 1153.1 (4) Å^3	Block, red
Z = 2	0.3 × 0.2 × 0.1 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	1770 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 26.0°, θmin = 1.3°
ω/2θ scans	h = 0→11
Absorption correction: empirical (using intensity measurements) via ψ scan (North et al., 1968)	k = 0→8
Tmin = 0.827, Tmax = 0.923	l = −18→18
2543 measured reflections	3 standard reflections every 200 reflections
2407 independent reflections	intensity decay: 0.1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.121	w = 1/[σ^2(Fo^2) + (0.061P)^2 + 0.3415P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
2407 reflections	Δρmax = 0.39 e Å^−3
273 parameters	Δρmin = −0.24 e Å^−3
32 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (4)

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Fe	0.73918 (7)	0.50240 (11)	0.48047 (6)	0.0471 (3)
O1	0.6138 (5)	0.7230 (10)	−0.0939 (3)	0.0891 (19)
O2	0.4837 (7)	0.7065 (14)	0.0067 (5)	0.121 (4)
O3	0.5688 (5)	0.6171 (8)	0.2545 (3)	0.0715 (14)
N	0.7018 (6)	0.7520 (9)	0.1368 (4)	0.0644 (16)
H1N	0.6316	0.6969	0.1480	0.077*
C1	0.5524 (11)	0.626 (2)	−0.2377 (6)	0.140 (5)
H1A	0.6277	0.6966	−0.2478	0.211*
H1B	0.4824	0.6286	−0.2884	0.211*
H1C	0.5815	0.5044	−0.2260	0.211*
C2	0.4998 (9)	0.6971 (18)	−0.1629 (6)	0.103 (3)
H2A	0.4359	0.6140	−0.1449	0.124*
H2B	0.4537	0.8097	−0.1781	0.124*
C3	0.5912 (8)	0.7231 (13)	−0.0131 (6)	0.078 (2)
C4	0.8097 (8)	0.5616 (12)	0.0387 (5)	0.079 (3)
H4A	0.7604	0.4586	0.0542	0.095*
H4B	0.8173	0.5496	−0.0222	0.095*
C5	0.7271 (7)	0.7323 (12)	0.0496 (5)	0.067 (2)
H5	0.7775	0.8368	0.0350	0.081*
C6	0.8795 (8)	0.9702 (11)	0.1840 (6)	0.082 (3)
H6A	0.9486	0.9042	0.1624	0.124*
H6B	0.9189	1.0318	0.2364	0.124*
H6C	0.8397	1.0554	0.1410	0.124*
C7	0.7728 (6)	0.8448 (10)	0.2030 (5)	0.0594 (18)
C8	0.7457 (6)	0.8279 (10)	0.2857 (5)	0.0562 (17)
H8	0.7946	0.8985	0.3293	0.067*
C9	0.6466 (6)	0.7078 (10)	0.3087 (5)	0.0527 (16)
C11	1.0559 (8)	0.6317 (15)	0.0600 (6)	0.088 (3)
H11	1.0418	0.6755	0.0033	0.105*
C12	0.9494 (7)	0.5603 (10)	0.0927 (5)	0.066 (2)
C13	0.9744 (8)	0.4950 (17)	0.1770 (5)	0.083 (2)
H13	0.9045	0.4433	0.2003	0.099*
C14	1.1027 (9)	0.506 (2)	0.2266 (6)	0.104 (3)
H14	1.1174	0.4650	0.2837	0.124*
C15	1.2073 (9)	0.5758 (16)	0.1937 (8)	0.104 (3)
H15	1.2933	0.5797	0.2277	0.125*
C16	1.1869 (9)	0.6395 (15)	0.1116 (8)	0.098 (3)
H16	1.2585	0.6884	0.0890	0.118*
C21	0.8933 (11)	0.3750 (17)	0.5568 (7)	0.112 (4)
H21	0.9336	0.4035	0.6171	0.135*
C22	0.9333 (7)	0.4406 (12)	0.4801 (10)	0.102 (3)
H22	1.0068	0.5254	0.4773	0.122*
C23	0.8521 (12)	0.3600 (17)	0.4102 (7)	0.104 (3)
H23	0.8568	0.3758	0.3484	0.125*
C24	0.7684 (10)	0.2470 (12)	0.4445 (8)	0.084 (3)
H24	0.6983	0.1732	0.4095	0.100*
C25	0.7899 (10)	0.2539 (13)	0.5283 (7)	0.087 (3)
H25	0.7404	0.1854	0.5660	0.105*
C31	0.5687 (6)	0.5785 (10)	0.5240 (5)	0.0564 (17)
H31	0.5216	0.5087	0.5626	0.068*
C32	0.6739 (6)	0.7020 (10)	0.5509 (5)	0.0527 (16)
H32	0.7121	0.7325	0.6114	0.063*
C33	0.7175 (6)	0.7704 (9)	0.4765 (5)	0.0475 (17)
H33	0.7897	0.8583	0.4758	0.057*
C34	0.6352 (5)	0.6897 (8)	0.4018 (4)	0.0456 (15)
C35	0.5434 (5)	0.5709 (9)	0.4327 (4)	0.0486 (15)
H35	0.4758	0.4953	0.3967	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe	0.0338 (4)	0.0342 (4)	0.0739 (6)	0.0023 (5)	0.0115 (3)	−0.0011 (7)
O1	0.071 (3)	0.130 (6)	0.064 (3)	−0.019 (4)	0.006 (3)	0.000 (4)
O2	0.056 (4)	0.217 (11)	0.092 (4)	−0.006 (5)	0.017 (3)	0.011 (6)
O3	0.065 (3)	0.079 (4)	0.068 (3)	−0.024 (3)	0.005 (2)	−0.002 (3)
N	0.059 (3)	0.067 (4)	0.068 (4)	−0.011 (3)	0.016 (3)	−0.001 (3)
C1	0.124 (9)	0.208 (16)	0.088 (7)	−0.046 (10)	0.015 (6)	−0.024 (9)
C2	0.096 (7)	0.125 (9)	0.080 (6)	−0.006 (7)	−0.008 (5)	0.018 (6)
C3	0.072 (5)	0.090 (6)	0.069 (5)	−0.012 (5)	0.010 (4)	0.008 (5)
C4	0.078 (5)	0.083 (7)	0.076 (5)	0.006 (4)	0.012 (4)	−0.011 (4)
C5	0.063 (4)	0.073 (5)	0.066 (5)	−0.007 (4)	0.011 (4)	−0.002 (4)
C6	0.096 (5)	0.060 (7)	0.096 (6)	−0.025 (5)	0.029 (4)	−0.004 (5)
C7	0.052 (4)	0.050 (4)	0.076 (5)	0.000 (3)	0.011 (4)	0.003 (4)
C8	0.050 (3)	0.048 (4)	0.070 (5)	−0.005 (3)	0.012 (3)	−0.004 (4)
C9	0.045 (3)	0.044 (4)	0.068 (4)	0.006 (3)	0.007 (3)	0.000 (3)
C11	0.080 (5)	0.095 (7)	0.096 (6)	0.009 (5)	0.037 (5)	0.002 (6)
C12	0.062 (4)	0.061 (5)	0.076 (5)	0.012 (3)	0.018 (4)	−0.009 (4)
C13	0.076 (4)	0.076 (5)	0.098 (6)	0.004 (7)	0.022 (4)	0.008 (8)
C14	0.085 (5)	0.108 (7)	0.112 (6)	0.025 (9)	0.001 (5)	0.018 (10)
C15	0.073 (6)	0.103 (8)	0.132 (8)	0.016 (5)	0.005 (6)	0.001 (7)
C16	0.064 (5)	0.089 (7)	0.150 (9)	0.002 (5)	0.041 (6)	0.002 (7)
C21	0.098 (6)	0.108 (7)	0.112 (6)	0.057 (5)	−0.034 (5)	−0.028 (5)
C22	0.038 (3)	0.059 (5)	0.214 (8)	0.006 (3)	0.033 (5)	0.015 (5)
C23	0.123 (6)	0.105 (6)	0.100 (6)	0.064 (5)	0.059 (5)	0.011 (5)
C24	0.078 (5)	0.054 (5)	0.112 (6)	0.017 (4)	−0.001 (5)	−0.016 (5)
C25	0.085 (5)	0.064 (5)	0.114 (6)	0.023 (4)	0.022 (5)	0.027 (5)
C31	0.039 (3)	0.053 (4)	0.081 (5)	0.005 (3)	0.022 (3)	0.000 (3)
C32	0.048 (3)	0.046 (4)	0.065 (4)	0.008 (3)	0.012 (3)	−0.011 (3)
C33	0.050 (4)	0.024 (3)	0.070 (5)	0.003 (3)	0.014 (4)	−0.005 (3)
C34	0.036 (3)	0.034 (3)	0.067 (4)	0.006 (2)	0.010 (3)	−0.003 (3)
C35	0.028 (3)	0.047 (3)	0.070 (4)	0.005 (2)	0.008 (3)	−0.004 (3)

Geometric parameters (Å, º)

O1—C2	1.438 (9)	C14—H14	0.9300
O1—C3	1.320 (9)	C15—C16	1.348 (13)
O2—C3	1.180 (10)	C15—H15	0.9300
O3—C9	1.245 (8)	C16—H16	0.9300
N—C5	1.435 (9)	C21—C25	1.390 (15)
N—C7	1.340 (9)	C21—C22	1.416 (14)
N—H1N	0.8600	C21—H21	0.9800
C1—C2	1.465 (12)	C22—C23	1.379 (14)
C1—H1A	0.9600	C22—H22	0.9800
C1—H1B	0.9600	C23—C24	1.366 (14)
C1—H1C	0.9600	C23—H23	0.9800
C2—H2A	0.9700	C24—C25	1.289 (13)
C2—H2B	0.9700	C24—H24	0.9800
C3—C5	1.532 (10)	C25—H25	0.9800
C4—C5	1.549 (11)	C31—C35	1.403 (9)
C4—C12	1.501 (10)	C31—C32	1.409 (9)
C4—H4A	0.9700	C31—H31	0.9800
C4—H4B	0.9700	C32—C33	1.409 (9)
C5—H5	0.9800	C32—H32	0.9800
C6—C7	1.493 (10)	C33—C34	1.436 (9)
C6—H6A	0.9600	C33—H33	0.9800
C6—H6B	0.9600	C34—C35	1.425 (8)
C6—H6C	0.9600	C35—H35	0.9800
C7—C8	1.371 (10)	Fe—C22	2.002 (7)
C8—C9	1.433 (9)	Fe—C21	2.015 (9)
C8—H8	0.9300	Fe—C23	2.017 (8)
C9—C34	1.484 (9)	Fe—C33	2.018 (6)
C11—C12	1.372 (11)	Fe—C34	2.026 (6)
C11—C16	1.414 (12)	Fe—C24	2.028 (9)
C11—H11	0.9300	Fe—C31	2.030 (6)
C12—C13	1.384 (11)	Fe—C32	2.032 (6)
C13—C14	1.381 (11)	Fe—C25	2.035 (9)
C13—H13	0.9300	Fe—C35	2.037 (5)
C14—C15	1.351 (13)
C22—Fe—C21	41.3 (4)	C7—C8—C9	123.8 (7)
C22—Fe—C23	40.1 (4)	C7—C8—H8	118.1
C21—Fe—C23	68.0 (4)	C9—C8—H8	118.1
C22—Fe—C33	109.2 (3)	O3—C9—C8	123.4 (6)
C21—Fe—C33	123.8 (4)	O3—C9—C34	117.9 (6)
C23—Fe—C33	125.2 (4)	C8—C9—C34	118.7 (6)
C22—Fe—C34	123.6 (4)	C12—C11—C16	120.7 (9)
C21—Fe—C34	160.6 (4)	C12—C11—H11	119.7
C23—Fe—C34	108.3 (4)	C16—C11—H11	119.7
C33—Fe—C34	41.6 (3)	C11—C12—C13	118.0 (7)
C22—Fe—C24	66.0 (4)	C11—C12—C4	120.0 (8)
C21—Fe—C24	65.4 (4)	C13—C12—C4	122.0 (7)
C23—Fe—C24	39.5 (4)	C14—C13—C12	120.3 (9)
C33—Fe—C24	161.6 (4)	C14—C13—H13	119.8
C34—Fe—C24	124.6 (4)	C12—C13—H13	119.8
C22—Fe—C31	160.6 (5)	C15—C14—C13	121.2 (9)
C21—Fe—C31	122.5 (4)	C15—C14—H14	119.4
C23—Fe—C31	156.7 (5)	C13—C14—H14	119.4
C33—Fe—C31	68.8 (3)	C16—C15—C14	120.1 (9)
C34—Fe—C31	68.6 (3)	C16—C15—H15	120.0
C24—Fe—C31	121.9 (4)	C14—C15—H15	120.0
C22—Fe—C32	125.4 (4)	C15—C16—C11	119.7 (9)
C21—Fe—C32	108.4 (4)	C15—C16—H16	120.2
C23—Fe—C32	161.8 (4)	C11—C16—H16	120.2
C33—Fe—C32	40.7 (3)	C25—C21—C22	105.3 (9)
C34—Fe—C32	68.8 (3)	C25—C21—Fe	70.7 (5)
C24—Fe—C32	156.8 (4)	C22—C21—Fe	68.8 (5)
C31—Fe—C32	40.6 (3)	C25—C21—H21	127.3
C22—Fe—C25	67.1 (4)	C22—C21—H21	127.3
C21—Fe—C25	40.1 (4)	Fe—C21—H21	127.3
C23—Fe—C25	65.7 (4)	C23—C22—C21	107.5 (9)
C33—Fe—C25	159.8 (4)	C23—C22—Fe	70.5 (5)
C34—Fe—C25	157.4 (4)	C21—C22—Fe	69.9 (5)
C24—Fe—C25	37.0 (4)	C23—C22—H22	126.2
C31—Fe—C25	107.7 (3)	C21—C22—H22	126.2
C32—Fe—C25	123.9 (4)	Fe—C22—H22	126.2
C22—Fe—C35	158.6 (4)	C24—C23—C22	106.1 (9)
C21—Fe—C35	157.3 (5)	C24—C23—Fe	70.7 (5)
C23—Fe—C35	122.1 (4)	C22—C23—Fe	69.3 (5)
C33—Fe—C35	69.3 (3)	C24—C23—H23	126.9
C34—Fe—C35	41.1 (2)	C22—C23—H23	126.9
C24—Fe—C35	108.2 (3)	Fe—C23—H23	126.9
C31—Fe—C35	40.3 (3)	C25—C24—C23	111.7 (10)
C32—Fe—C35	68.3 (3)	C25—C24—Fe	71.8 (6)
C25—Fe—C35	121.7 (3)	C23—C24—Fe	69.8 (6)
C3—O1—C2	117.8 (7)	C25—C24—H24	124.1
C7—N—C5	128.7 (6)	C23—C24—H24	124.1
C7—N—H1N	115.7	Fe—C24—H24	124.1
C5—N—H1N	115.7	C24—C25—C21	109.3 (10)
C2—C1—H1A	109.5	C24—C25—Fe	71.2 (5)
C2—C1—H1B	109.5	C21—C25—Fe	69.2 (6)
H1A—C1—H1B	109.5	C24—C25—H25	125.3
C2—C1—H1C	109.5	C21—C25—H25	125.3
H1A—C1—H1C	109.5	Fe—C25—H25	125.3
H1B—C1—H1C	109.5	C35—C31—C32	108.7 (6)
C1—C2—O1	107.2 (8)	C35—C31—Fe	70.1 (3)
C1—C2—H2A	110.3	C32—C31—Fe	69.7 (3)
O1—C2—H2A	110.3	C35—C31—H31	125.7
C1—C2—H2B	110.3	C32—C31—H31	125.7
O1—C2—H2B	110.3	Fe—C31—H31	125.7
H2A—C2—H2B	108.5	C31—C32—C33	108.6 (6)
O2—C3—O1	124.8 (8)	C31—C32—Fe	69.7 (4)
O1—C3—C5	109.0 (7)	C33—C32—Fe	69.1 (4)
O2—C3—C5	126.0 (8)	C31—C32—H32	125.7
C5—C4—C12	114.1 (7)	C33—C32—H32	125.7
C12—C4—H4A	108.7	Fe—C32—H32	125.7
C5—C4—H4A	108.7	C32—C33—C34	107.4 (6)
C12—C4—H4B	108.7	C32—C33—Fe	70.2 (4)
C5—C4—H4B	108.7	C34—C33—Fe	69.5 (4)
H4A—C4—H4B	107.6	C32—C33—H33	126.3
N—C5—C4	112.2 (7)	C34—C33—H33	126.3
N—C5—C3	108.8 (6)	Fe—C33—H33	126.3
C3—C5—C4	109.0 (7)	C35—C34—C33	107.4 (6)
N—C5—H5	108.9	C35—C34—C9	123.8 (6)
C3—C5—H5	108.9	C33—C34—C9	128.6 (6)
C4—C5—H5	108.9	C35—C34—Fe	69.9 (3)
C7—C6—H6A	109.5	C33—C34—Fe	68.9 (4)
C7—C6—H6B	109.5	C9—C34—Fe	122.4 (4)
H6A—C6—H6B	109.5	C31—C35—C34	107.9 (6)
C7—C6—H6C	109.5	C31—C35—Fe	69.6 (3)
H6A—C6—H6C	109.5	C34—C35—Fe	69.0 (3)
H6B—C6—H6C	109.5	C31—C35—H35	126.0
N—C7—C6	118.3 (7)	C34—C35—H35	126.0
N—C7—C8	120.7 (6)	Fe—C35—H35	126.0
C6—C7—C8	120.9 (7)
C3—O1—C2—C1	−155.8 (10)	C24—Fe—C25—C21	120.2 (9)
C2—O1—C3—O2	−1.4 (16)	C31—Fe—C25—C21	−119.8 (7)
C2—O1—C3—C5	174.0 (8)	C32—Fe—C25—C21	−78.1 (7)
C7—N—C5—C3	−145.0 (8)	C35—Fe—C25—C21	−161.8 (6)
C7—N—C5—C4	94.4 (9)	C22—Fe—C31—C35	170.5 (10)
O2—C3—C5—N	−10.9 (15)	C21—Fe—C31—C35	−160.0 (6)
O1—C3—C5—N	173.8 (7)	C23—Fe—C31—C35	−49.0 (11)
O2—C3—C5—C4	111.7 (12)	C33—Fe—C31—C35	82.6 (4)
O1—C3—C5—C4	−63.6 (9)	C34—Fe—C31—C35	37.8 (4)
C12—C4—C5—N	−63.2 (9)	C24—Fe—C31—C35	−80.6 (5)
C12—C4—C5—C3	176.2 (6)	C32—Fe—C31—C35	119.8 (6)
C5—N—C7—C8	−170.3 (7)	C25—Fe—C31—C35	−118.5 (5)
C5—N—C7—C6	11.3 (11)	C22—Fe—C31—C32	50.8 (12)
N—C7—C8—C9	2.8 (11)	C21—Fe—C31—C32	80.2 (6)
C6—C7—C8—C9	−178.8 (7)	C23—Fe—C31—C32	−168.8 (9)
C7—C8—C9—O3	−5.5 (11)	C33—Fe—C31—C32	−37.1 (4)
C7—C8—C9—C34	174.5 (6)	C34—Fe—C31—C32	−81.9 (4)
C16—C11—C12—C13	−0.6 (14)	C24—Fe—C31—C32	159.7 (5)
C16—C11—C12—C4	176.8 (8)	C25—Fe—C31—C32	121.8 (5)
C5—C4—C12—C11	−88.8 (9)	C35—Fe—C31—C32	−119.8 (6)
C5—C4—C12—C13	88.6 (11)	C35—C31—C32—C33	−1.2 (7)
C11—C12—C13—C14	1.5 (16)	Fe—C31—C32—C33	58.3 (4)
C4—C12—C13—C14	−175.9 (11)	C35—C31—C32—Fe	−59.5 (4)
C12—C13—C14—C15	−2 (2)	C22—Fe—C32—C31	−161.6 (5)
C13—C14—C15—C16	1 (2)	C21—Fe—C32—C31	−118.9 (6)
C14—C15—C16—C11	−0.5 (17)	C23—Fe—C32—C31	165.8 (11)
C12—C11—C16—C15	0.1 (16)	C33—Fe—C32—C31	120.3 (6)
C22—Fe—C21—C25	−115.8 (9)	C34—Fe—C32—C31	81.5 (4)
C23—Fe—C21—C25	−77.9 (7)	C24—Fe—C32—C31	−48.6 (9)
C33—Fe—C21—C25	163.5 (5)	C25—Fe—C32—C31	−77.3 (6)
C34—Fe—C21—C25	−160.6 (9)	C35—Fe—C32—C31	37.2 (4)
C24—Fe—C21—C25	−34.9 (6)	C22—Fe—C32—C33	78.1 (6)
C31—Fe—C21—C25	78.6 (7)	C21—Fe—C32—C33	120.8 (6)
C32—Fe—C21—C25	121.1 (6)	C23—Fe—C32—C33	45.4 (12)
C35—Fe—C21—C25	43.5 (12)	C34—Fe—C32—C33	−38.8 (4)
C23—Fe—C21—C22	37.9 (6)	C24—Fe—C32—C33	−168.9 (7)
C33—Fe—C21—C22	−80.7 (7)	C31—Fe—C32—C33	−120.3 (6)
C34—Fe—C21—C22	−44.8 (13)	C25—Fe—C32—C33	162.4 (5)
C24—Fe—C21—C22	80.9 (7)	C35—Fe—C32—C33	−83.1 (4)
C31—Fe—C21—C22	−165.6 (6)	C31—C32—C33—C34	1.2 (7)
C32—Fe—C21—C22	−123.1 (6)	Fe—C32—C33—C34	59.8 (4)
C25—Fe—C21—C22	115.8 (9)	C31—C32—C33—Fe	−58.6 (5)
C35—Fe—C21—C22	159.3 (8)	C22—Fe—C33—C32	−122.3 (5)
C25—C21—C22—C23	1.0 (10)	C21—Fe—C33—C32	−78.7 (6)
Fe—C21—C22—C23	−60.8 (6)	C23—Fe—C33—C32	−164.2 (5)
C25—C21—C22—Fe	61.8 (6)	C34—Fe—C33—C32	118.3 (5)
C21—Fe—C22—C23	118.0 (9)	C24—Fe—C33—C32	166.2 (9)
C33—Fe—C22—C23	−122.3 (7)	C31—Fe—C33—C32	37.0 (4)
C34—Fe—C22—C23	−78.3 (7)	C25—Fe—C33—C32	−46.7 (10)
C24—Fe—C22—C23	38.5 (6)	C35—Fe—C33—C32	80.4 (4)
C31—Fe—C22—C23	157.0 (10)	C22—Fe—C33—C34	119.4 (6)
C32—Fe—C22—C23	−164.8 (6)	C21—Fe—C33—C34	163.0 (5)
C25—Fe—C22—C23	79.0 (7)	C23—Fe—C33—C34	77.5 (6)
C35—Fe—C22—C23	−40.0 (12)	C24—Fe—C33—C34	47.9 (11)
C23—Fe—C22—C21	−118.0 (9)	C31—Fe—C33—C34	−81.3 (4)
C33—Fe—C22—C21	119.7 (7)	C32—Fe—C33—C34	−118.3 (5)
C34—Fe—C22—C21	163.7 (6)	C25—Fe—C33—C34	−165.0 (8)
C24—Fe—C22—C21	−79.5 (7)	C35—Fe—C33—C34	−37.9 (3)
C31—Fe—C22—C21	39.0 (14)	C32—C33—C34—C35	−0.7 (7)
C32—Fe—C22—C21	77.1 (7)	Fe—C33—C34—C35	59.5 (4)
C25—Fe—C22—C21	−39.1 (6)	C32—C33—C34—C9	−175.5 (6)
C35—Fe—C22—C21	−158.1 (9)	Fe—C33—C34—C9	−115.3 (6)
C21—C22—C23—C24	−1.2 (10)	C32—C33—C34—Fe	−60.2 (4)
Fe—C22—C23—C24	−61.5 (6)	O3—C9—C34—C35	1.9 (9)
C21—C22—C23—Fe	60.4 (6)	C8—C9—C34—C35	−178.1 (6)
C22—Fe—C23—C24	116.5 (9)	O3—C9—C34—C33	175.9 (6)
C21—Fe—C23—C24	77.6 (7)	C8—C9—C34—C33	−4.1 (10)
C33—Fe—C23—C24	−165.7 (5)	O3—C9—C34—Fe	88.2 (7)
C34—Fe—C23—C24	−122.7 (6)	C8—C9—C34—Fe	−91.8 (7)
C31—Fe—C23—C24	−44.3 (12)	C22—Fe—C34—C35	159.9 (5)
C32—Fe—C23—C24	159.6 (10)	C21—Fe—C34—C35	−166.1 (10)
C25—Fe—C23—C24	33.9 (6)	C23—Fe—C34—C35	118.2 (6)
C35—Fe—C23—C24	−79.6 (7)	C33—Fe—C34—C35	−118.9 (5)
C21—Fe—C23—C22	−38.9 (7)	C24—Fe—C34—C35	77.7 (5)
C33—Fe—C23—C22	77.7 (7)	C31—Fe—C34—C35	−37.2 (4)
C34—Fe—C23—C22	120.8 (6)	C32—Fe—C34—C35	−80.9 (4)
C24—Fe—C23—C22	−116.5 (9)	C25—Fe—C34—C35	47.7 (9)
C31—Fe—C23—C22	−160.8 (8)	C22—Fe—C34—C33	−81.2 (6)
C32—Fe—C23—C22	43.1 (14)	C21—Fe—C34—C33	−47.2 (12)
C25—Fe—C23—C22	−82.6 (7)	C23—Fe—C34—C33	−122.8 (6)
C35—Fe—C23—C22	163.9 (6)	C24—Fe—C34—C33	−163.4 (5)
C22—C23—C24—C25	1.0 (11)	C31—Fe—C34—C33	81.7 (4)
Fe—C23—C24—C25	−59.7 (7)	C32—Fe—C34—C33	38.0 (4)
C22—C23—C24—Fe	60.6 (6)	C25—Fe—C34—C33	166.6 (8)
C22—Fe—C24—C25	83.2 (7)	C35—Fe—C34—C33	118.9 (5)
C21—Fe—C24—C25	37.7 (7)	C22—Fe—C34—C9	42.0 (7)
C23—Fe—C24—C25	122.4 (9)	C21—Fe—C34—C9	75.9 (12)
C33—Fe—C24—C25	161.9 (8)	C23—Fe—C34—C9	0.3 (7)
C34—Fe—C24—C25	−161.4 (5)	C33—Fe—C34—C9	123.2 (7)
C31—Fe—C24—C25	−76.6 (7)	C24—Fe—C34—C9	−40.3 (7)
C32—Fe—C24—C25	−41.5 (11)	C31—Fe—C34—C9	−155.1 (6)
C35—Fe—C24—C25	−118.8 (6)	C32—Fe—C34—C9	161.2 (6)
C22—Fe—C24—C23	−39.2 (6)	C25—Fe—C34—C9	−70.2 (10)
C21—Fe—C24—C23	−84.7 (7)	C35—Fe—C34—C9	−117.9 (7)
C33—Fe—C24—C23	39.5 (12)	C32—C31—C35—C34	0.7 (7)
C34—Fe—C24—C23	76.2 (7)	Fe—C31—C35—C34	−58.5 (4)
C31—Fe—C24—C23	161.0 (6)	C32—C31—C35—Fe	59.3 (4)
C32—Fe—C24—C23	−163.9 (8)	C33—C34—C35—C31	0.0 (7)
C25—Fe—C24—C23	−122.4 (9)	C9—C34—C35—C31	175.1 (5)
C35—Fe—C24—C23	118.7 (6)	Fe—C34—C35—C31	58.9 (4)
C23—C24—C25—C21	−0.3 (11)	C33—C34—C35—Fe	−58.9 (4)
Fe—C24—C25—C21	−58.9 (7)	C9—C34—C35—Fe	116.2 (6)
C23—C24—C25—Fe	58.5 (7)	C22—Fe—C35—C31	−171.3 (9)
C22—C21—C25—C24	−0.4 (10)	C21—Fe—C35—C31	48.4 (11)
Fe—C21—C25—C24	60.1 (7)	C23—Fe—C35—C31	159.3 (6)
C22—C21—C25—Fe	−60.5 (6)	C33—Fe—C35—C31	−81.2 (4)
C22—Fe—C25—C24	−80.1 (7)	C34—Fe—C35—C31	−119.7 (6)
C21—Fe—C25—C24	−120.2 (9)	C24—Fe—C35—C31	118.2 (5)
C23—Fe—C25—C24	−36.1 (7)	C32—Fe—C35—C31	−37.4 (4)
C33—Fe—C25—C24	−163.4 (8)	C25—Fe—C35—C31	79.9 (5)
C34—Fe—C25—C24	43.1 (11)	C22—Fe—C35—C34	−51.7 (10)
C31—Fe—C25—C24	119.9 (6)	C21—Fe—C35—C34	168.1 (9)
C32—Fe—C25—C24	161.7 (6)	C23—Fe—C35—C34	−81.0 (6)
C35—Fe—C25—C24	77.9 (7)	C33—Fe—C35—C34	38.4 (4)
C22—Fe—C25—C21	40.2 (6)	C24—Fe—C35—C34	−122.2 (5)
C23—Fe—C25—C21	84.1 (7)	C31—Fe—C35—C34	119.7 (6)
C33—Fe—C25—C21	−43.2 (12)	C32—Fe—C35—C34	82.2 (4)
C34—Fe—C25—C21	163.3 (8)	C25—Fe—C35—C34	−160.5 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N—H1N···O3	0.86	1.97	2.655 (8)	135
C2—H2B···O3^i	0.97	2.58	3.472 (14)	152

Symmetry code: (i) −x+1, y+1/2, −z.