Crystal structure of bis­[4-(1H-pyrrol-1-yl)phen­yl] ferrocene-1,1′-di­carboxyl­ate: a potential chemotherapeutic drug

The solid-state structure of a disubstituted ferrocene with electrochemically active pendant groups has been determined. This is a potential chemotherapeutic drug.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.044
• wR factor = 0.117
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      3.081 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          3 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1 Note

Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          2 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          9 Note

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

   0 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
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Bis[4-(1H-pyrrol-1-yl)phenyl] ferrocene-1,1'-dicarboxylate

Crystal data

[Fe(C16H12NO2)2]	Dx = 1.537 Mg m^−3
Mr = 556.38	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 2807 reflections
a = 10.6386 (15) Å	θ = 2.7–28.1°
b = 7.3948 (10) Å	µ = 0.67 mm^−1
c = 30.554 (4) Å	T = 100 K
V = 2403.7 (6) Å^3	Block, orange
Z = 4	0.28 × 0.26 × 0.23 mm
F(000) = 1152

Data collection

Bruker APEXII CCD diffractometer	2247 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.077
Absorption correction: multi-scan (SADABS; Bruker, 2010)	θmax = 28.4°, θmin = 2.7°
Tmin = 0.833, Tmax = 0.877	h = −13→14
12444 measured reflections	k = −9→9
2999 independent reflections	l = −37→40

Refinement

Refinement on F^2	0 restraints
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) = 0.117	w = 1/[σ^2(Fo^2) + (0.047P)^2 + 0.928P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
2999 reflections	Δρmax = 0.34 e Å^−3
178 parameters	Δρmin = −0.62 e Å^−3

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.

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

	x	y	z	Uiso*/Ueq
Fe1	0.5000	0.5000	0.5000	0.01323 (14)
O1	0.23108 (15)	0.4748 (2)	0.41347 (5)	0.0213 (4)
O2	0.41465 (13)	0.3430 (2)	0.39352 (4)	0.0173 (3)
N1	0.37269 (16)	0.3889 (2)	0.21120 (5)	0.0133 (4)
C1	0.3680 (2)	0.3523 (3)	0.46783 (7)	0.0149 (4)
C2	0.3145 (2)	0.4294 (3)	0.50667 (6)	0.0169 (4)
H2A	0.2415	0.5142	0.5081	0.020*
C3	0.3857 (2)	0.3643 (3)	0.54286 (7)	0.0216 (5)
H3A	0.3716	0.3970	0.5742	0.026*
C4	0.4812 (2)	0.2469 (3)	0.52692 (7)	0.0191 (5)
H4A	0.5454	0.1827	0.5451	0.023*
C5	0.4712 (2)	0.2403 (3)	0.48035 (7)	0.0166 (4)
H5A	0.5262	0.1693	0.4601	0.020*
C6	0.3264 (2)	0.3975 (3)	0.42318 (6)	0.0144 (4)
C7	0.3923 (2)	0.3684 (3)	0.34853 (6)	0.0145 (4)
C8	0.48316 (19)	0.4601 (3)	0.32540 (7)	0.0155 (4)
H8A	0.5502	0.5182	0.3404	0.019*
C9	0.47630 (19)	0.4673 (3)	0.27993 (7)	0.0151 (4)
H9A	0.5398	0.5288	0.2639	0.018*
C10	0.37736 (19)	0.3853 (2)	0.25769 (6)	0.0121 (4)
C11	0.28353 (19)	0.2994 (3)	0.28206 (7)	0.0149 (4)
H11A	0.2137	0.2469	0.2674	0.018*
C12	0.29095 (19)	0.2899 (3)	0.32731 (6)	0.0154 (4)
H12A	0.2272	0.2302	0.3436	0.018*
C13	0.2795 (2)	0.3154 (3)	0.18518 (7)	0.0174 (4)
H13A	0.2077	0.2518	0.1954	0.021*
C14	0.3076 (2)	0.3494 (3)	0.14240 (7)	0.0195 (5)
H14A	0.2587	0.3153	0.1177	0.023*
C15	0.4232 (2)	0.4449 (3)	0.14143 (7)	0.0213 (5)
H15A	0.4661	0.4862	0.1161	0.026*
C16	0.4613 (2)	0.4663 (3)	0.18374 (7)	0.0184 (4)
H16A	0.5364	0.5248	0.1929	0.022*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0159 (2)	0.0111 (2)	0.0127 (2)	−0.00228 (16)	−0.00142 (16)	0.00108 (15)
O1	0.0196 (9)	0.0274 (8)	0.0169 (8)	0.0076 (7)	−0.0004 (6)	−0.0006 (6)
O2	0.0162 (8)	0.0220 (8)	0.0137 (7)	0.0029 (6)	−0.0003 (6)	−0.0013 (6)
N1	0.0123 (8)	0.0123 (8)	0.0154 (8)	−0.0003 (7)	0.0015 (7)	−0.0003 (6)
C1	0.0164 (10)	0.0125 (9)	0.0160 (10)	−0.0039 (8)	0.0003 (8)	−0.0003 (7)
C2	0.0161 (10)	0.0168 (10)	0.0179 (10)	−0.0040 (9)	0.0031 (8)	0.0006 (8)
C3	0.0292 (12)	0.0190 (11)	0.0165 (11)	−0.0081 (10)	0.0015 (9)	0.0016 (8)
C4	0.0232 (12)	0.0139 (10)	0.0201 (11)	−0.0055 (9)	−0.0051 (9)	0.0046 (8)
C5	0.0197 (11)	0.0105 (9)	0.0197 (11)	−0.0009 (9)	−0.0040 (9)	0.0007 (8)
C6	0.0149 (10)	0.0121 (9)	0.0162 (10)	−0.0015 (8)	0.0004 (8)	−0.0014 (7)
C7	0.0157 (10)	0.0137 (9)	0.0142 (10)	0.0024 (8)	−0.0008 (8)	−0.0014 (7)
C8	0.0135 (10)	0.0150 (10)	0.0180 (10)	−0.0025 (8)	−0.0008 (8)	−0.0027 (8)
C9	0.0127 (10)	0.0135 (9)	0.0192 (10)	−0.0006 (8)	0.0023 (8)	0.0003 (8)
C10	0.0127 (10)	0.0085 (9)	0.0151 (10)	0.0031 (8)	0.0003 (8)	−0.0006 (7)
C11	0.0118 (10)	0.0136 (9)	0.0193 (10)	−0.0027 (8)	−0.0012 (8)	0.0004 (8)
C12	0.0150 (10)	0.0138 (9)	0.0173 (10)	−0.0010 (8)	0.0023 (8)	0.0018 (8)
C13	0.0139 (10)	0.0163 (10)	0.0219 (11)	−0.0002 (9)	−0.0005 (8)	−0.0016 (8)
C14	0.0211 (11)	0.0196 (11)	0.0177 (10)	0.0066 (9)	−0.0016 (9)	−0.0022 (8)
C15	0.0250 (13)	0.0211 (11)	0.0179 (11)	0.0031 (10)	0.0048 (9)	0.0015 (9)
C16	0.0161 (10)	0.0176 (10)	0.0217 (11)	−0.0032 (9)	0.0035 (9)	0.0024 (8)

Geometric parameters (Å, º)

Fe1—C1	2.032 (2)	C3—H3A	1.0000
Fe1—C1^i	2.033 (2)	C4—C5	1.428 (3)
Fe1—C5	2.035 (2)	C4—H4A	1.0000
Fe1—C5^i	2.035 (2)	C5—H5A	1.0000
Fe1—C3^i	2.050 (2)	C7—C8	1.376 (3)
Fe1—C3	2.050 (2)	C7—C12	1.386 (3)
Fe1—C2	2.051 (2)	C8—C9	1.392 (3)
Fe1—C2^i	2.051 (2)	C8—H8A	0.9500
Fe1—C4^i	2.055 (2)	C9—C10	1.392 (3)
Fe1—C4	2.055 (2)	C9—H9A	0.9500
O1—C6	1.201 (3)	C10—C11	1.398 (3)
O2—C6	1.366 (2)	C11—C12	1.387 (3)
O2—C7	1.407 (2)	C11—H11A	0.9500
N1—C13	1.382 (3)	C12—H12A	0.9500
N1—C16	1.386 (3)	C13—C14	1.364 (3)
N1—C10	1.422 (3)	C13—H13A	0.9500
C1—C5	1.427 (3)	C14—C15	1.418 (3)
C1—C2	1.434 (3)	C14—H14A	0.9500
C1—C6	1.473 (3)	C15—C16	1.364 (3)
C2—C3	1.424 (3)	C15—H15A	0.9500
C2—H2A	1.0000	C16—H16A	0.9500
C3—C4	1.423 (3)
C1—Fe1—C1^i	180.0	C3—C2—Fe1	69.63 (13)
C1—Fe1—C5	41.09 (8)	C1—C2—Fe1	68.75 (12)
C1^i—Fe1—C5	138.91 (8)	C3—C2—H2A	126.3
C1—Fe1—C5^i	138.91 (8)	C1—C2—H2A	126.3
C1^i—Fe1—C5^i	41.09 (8)	Fe1—C2—H2A	126.3
C5—Fe1—C5^i	180.0	C4—C3—C2	108.66 (19)
C1—Fe1—C3^i	111.35 (8)	C4—C3—Fe1	69.90 (12)
C1^i—Fe1—C3^i	68.66 (8)	C2—C3—Fe1	69.74 (12)
C5—Fe1—C3^i	111.27 (9)	C4—C3—H3A	125.7
C5^i—Fe1—C3^i	68.73 (9)	C2—C3—H3A	125.7
C1—Fe1—C3	68.65 (8)	Fe1—C3—H3A	125.7
C1^i—Fe1—C3	111.34 (8)	C3—C4—C5	107.97 (18)
C5—Fe1—C3	68.73 (9)	C3—C4—Fe1	69.54 (12)
C5^i—Fe1—C3	111.27 (9)	C5—C4—Fe1	68.84 (11)
C3^i—Fe1—C3	180.0	C3—C4—H4A	126.0
C1—Fe1—C2	41.11 (8)	C5—C4—H4A	126.0
C1^i—Fe1—C2	138.89 (8)	Fe1—C4—H4A	126.0
C5—Fe1—C2	69.15 (9)	C1—C5—C4	107.75 (18)
C5^i—Fe1—C2	110.85 (9)	C1—C5—Fe1	69.36 (11)
C3^i—Fe1—C2	139.37 (9)	C4—C5—Fe1	70.30 (11)
C3—Fe1—C2	40.63 (9)	C1—C5—H5A	126.1
C1—Fe1—C2^i	138.89 (8)	C4—C5—H5A	126.1
C1^i—Fe1—C2^i	41.11 (8)	Fe1—C5—H5A	126.1
C5—Fe1—C2^i	110.85 (9)	O1—C6—O2	123.84 (18)
C5^i—Fe1—C2^i	69.15 (9)	O1—C6—C1	126.17 (19)
C3^i—Fe1—C2^i	40.63 (9)	O2—C6—C1	109.97 (18)
C3—Fe1—C2^i	139.37 (9)	C8—C7—C12	120.85 (19)
C2—Fe1—C2^i	180.0	C8—C7—O2	116.66 (18)
C1—Fe1—C4^i	111.29 (8)	C12—C7—O2	122.16 (18)
C1^i—Fe1—C4^i	68.71 (8)	C7—C8—C9	119.63 (19)
C5—Fe1—C4^i	139.13 (9)	C7—C8—H8A	120.2
C5^i—Fe1—C4^i	40.87 (9)	C9—C8—H8A	120.2
C3^i—Fe1—C4^i	40.56 (9)	C10—C9—C8	120.67 (19)
C3—Fe1—C4^i	139.44 (9)	C10—C9—H9A	119.7
C2—Fe1—C4^i	111.44 (9)	C8—C9—H9A	119.7
C2^i—Fe1—C4^i	68.56 (9)	C9—C10—C11	118.55 (18)
C1—Fe1—C4	68.71 (8)	C9—C10—N1	120.40 (18)
C1^i—Fe1—C4	111.29 (8)	C11—C10—N1	121.05 (17)
C5—Fe1—C4	40.87 (9)	C12—C11—C10	120.90 (19)
C5^i—Fe1—C4	139.13 (9)	C12—C11—H11A	119.5
C3^i—Fe1—C4	139.44 (9)	C10—C11—H11A	119.5
C3—Fe1—C4	40.56 (9)	C7—C12—C11	119.31 (19)
C2—Fe1—C4	68.56 (9)	C7—C12—H12A	120.3
C2^i—Fe1—C4	111.44 (9)	C11—C12—H12A	120.3
C4^i—Fe1—C4	180.00 (11)	C14—C13—N1	108.78 (19)
C6—O2—C7	119.52 (16)	C14—C13—H13A	125.6
C13—N1—C16	107.58 (17)	N1—C13—H13A	125.6
C13—N1—C10	126.34 (17)	C13—C14—C15	107.54 (19)
C16—N1—C10	126.08 (18)	C13—C14—H14A	126.2
C5—C1—C2	108.28 (18)	C15—C14—H14A	126.2
C5—C1—C6	127.65 (19)	C16—C15—C14	107.2 (2)
C2—C1—C6	123.89 (19)	C16—C15—H15A	126.4
C5—C1—Fe1	69.56 (12)	C14—C15—H15A	126.4
C2—C1—Fe1	70.14 (12)	C15—C16—N1	108.9 (2)
C6—C1—Fe1	122.25 (14)	C15—C16—H16A	125.6
C3—C2—C1	107.3 (2)	N1—C16—H16A	125.6

Symmetry code: (i) −x+1, −y+1, −z+1.