Substituent effects in bis(arene)chromium compounds containing a CN group in the aromatic ring

The crystal structures of Cr(PhCN)₂ (2), (PhCN)Cr(PhCH₃) (3) and (PhCN)Cr(PhCF₃) (4) prepared by means of the Metal Vapor Synthesis (MVS) technique have been determined. Compounds (2), (3) and (4) crystallize as discrete sandwich complexes having intrinsic C_2v(mm2), C_s(m) and C₁(1) symmetries, respectively. The X-ray diffraction study has revealed a synperiplanar conformation for (2) and (3), and a synclinal conformation for (4) with a torsion angle (C_ipso1–Centroid1–Centroid2–C_ipso2) of φ = 63.5°. The angles between the ligand planes are 2.2, 3.9 and 1.8°, respectively. The Cr atom is slightly (by 0.04–0.06 Å) displaced towards the substituents from the line connecting the centers of the opposite aromatic rings. The Cr—C_ipso distances are 2.115 (2)–2.137 (2), 2.112 (2) and 2.185 (3) Å for CN, CF₃ and CH₃ groups, respectively. The CN groups as well as the H atoms lie out of the C₆ ring planes and are bent towards the Cr atom, but the C atom of the CH₃ group also lying out of the C₆ ring plane is bent away from the Cr atom. The C atom of the CF₃ group is essentially coplanar to the C₆ ring plane. There are no unusual intermolecular contacts in the structures of (2)–(4).

Computing details

For all compounds, data collection: SMART (Bruker, 1998b); cell refinement: SAINTPlus (Bruker, 1998a); data reduction: SAINTPlus (Bruker, 1998a). Program(s) used to solve structure: SHELXTL ver. 5.1 (Sheldrick, 1998b) for (2), (3); SHELXTL ver. 5.10 (Sheldrick, 1998b) for (4). Program(s) used to refine structure: SHELXTL ver. 5.1 (Sheldrick, 1998b) for (2), (3); SHELXTL ver. 5.10 (Sheldrick, 1998b) for (4). Molecular graphics: SHELXTL ver. 5.1 (Sheldrick, 1998b) for (2), (3); SHELXTL ver. 5.10 (Sheldrick, 1998b) for (4). Software used to prepare material for publication: SHELXTL ver. 5.1 (Sheldrick, 1998b) for (2), (3); SHELXTL ver. 5.10 (Sheldrick, 1998b) for (4).

Figures

(2)

Crystal data

C14H10CrN2	F(000) = 528
Mr = 258.24	Dx = 1.643 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.7300 (5) Å	Cell parameters from 4186 reflections
b = 12.0887 (8) Å	θ = 2.5–30.0°
c = 11.1762 (8) Å	µ = 1.07 mm^−1
β = 91.683 (1)°	T = 120 K
V = 1043.92 (12) Å^3	Prism, brown
Z = 4	0.36 × 0.28 × 0.24 mm

Data collection

Bruker SMART 1000 CCD area detector diffractometer	2984 independent reflections
Radiation source: normal-focus sealed tube	2343 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
phi and ω scans	θmax = 30.0°, θmin = 2.5°
Absorption correction: multi-scan SADABS (Sheldrick, 1998a)	h = −10→10
Tmin = 0.700, Tmax = 0.784	k = −14→17
7835 measured reflections	l = −13→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: difference Fourier map
wR(F^2) = 0.086	All H-atom parameters refined
S = 1.02	w = 1/[σ^2(Fo^2) + (0.030P)^2 + 1.5P] where P = (Fo^2 + 2Fc^2)/3
2984 reflections	(Δ/σ)max < 0.001
194 parameters	Δρmax = 0.83 e Å^−3
0 restraints	Δρmin = −0.52 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.

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
Cr1	0.04345 (3)	0.75146 (2)	0.93561 (2)	0.01128 (8)
N1	−0.3609 (2)	0.51400 (15)	0.87685 (16)	0.0258 (4)
N2	−0.0860 (2)	0.52292 (15)	0.65612 (16)	0.0258 (4)
C1	−0.1888 (2)	0.66959 (14)	0.98524 (15)	0.0148 (3)
C2	−0.0529 (2)	0.64107 (15)	1.06843 (15)	0.0161 (3)
C3	0.0421 (2)	0.72575 (16)	1.12641 (16)	0.0174 (3)
C4	0.0049 (2)	0.83751 (16)	1.10249 (16)	0.0183 (3)
C5	−0.1295 (2)	0.86610 (15)	1.01993 (16)	0.0172 (3)
C6	−0.2267 (2)	0.78284 (15)	0.95990 (16)	0.0153 (3)
C7	−0.2835 (2)	0.58377 (15)	0.92391 (17)	0.0179 (3)
C8	0.0919 (2)	0.67404 (15)	0.76786 (15)	0.0151 (3)
C9	0.2242 (2)	0.64241 (15)	0.85240 (16)	0.0159 (3)
C10	0.3166 (2)	0.72568 (16)	0.91566 (16)	0.0176 (3)
C11	0.2796 (2)	0.83835 (16)	0.89506 (17)	0.0194 (4)
C12	0.1483 (2)	0.86904 (15)	0.81068 (16)	0.0180 (3)
C13	0.0530 (2)	0.78747 (16)	0.74723 (15)	0.0165 (3)
C14	−0.0070 (2)	0.59033 (16)	0.70591 (16)	0.0186 (3)
H2	−0.023 (3)	0.565 (2)	1.084 (2)	0.028 (6)*
H3	0.141 (3)	0.705 (2)	1.179 (2)	0.032 (7)*
H4	0.078 (3)	0.8996 (19)	1.141 (2)	0.019 (6)*
H5	−0.153 (3)	0.943 (2)	1.000 (2)	0.024 (6)*
H6	−0.324 (3)	0.805 (2)	0.900 (2)	0.028 (6)*
H9	0.251 (3)	0.566 (2)	0.866 (2)	0.027 (6)*
H10	0.400 (3)	0.704 (2)	0.978 (2)	0.027 (6)*
H11	0.344 (3)	0.898 (2)	0.944 (2)	0.028 (6)*
H12	0.119 (3)	0.947 (2)	0.802 (2)	0.022 (6)*
H13	−0.046 (3)	0.814 (2)	0.693 (2)	0.036 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cr1	0.01087 (13)	0.01296 (13)	0.01005 (13)	−0.00019 (9)	0.00075 (8)	−0.00013 (10)
N1	0.0232 (8)	0.0236 (8)	0.0303 (9)	−0.0034 (7)	−0.0025 (7)	−0.0013 (7)
N2	0.0273 (8)	0.0254 (8)	0.0245 (8)	0.0029 (7)	−0.0040 (7)	−0.0064 (7)
C1	0.0135 (7)	0.0172 (8)	0.0139 (7)	−0.0019 (6)	0.0029 (6)	−0.0010 (6)
C2	0.0166 (8)	0.0169 (8)	0.0150 (8)	0.0015 (6)	0.0032 (6)	0.0045 (6)
C3	0.0151 (7)	0.0267 (9)	0.0104 (7)	0.0002 (7)	0.0008 (6)	0.0007 (7)
C4	0.0177 (8)	0.0234 (9)	0.0139 (8)	−0.0020 (7)	0.0044 (6)	−0.0048 (7)
C5	0.0188 (8)	0.0161 (8)	0.0169 (8)	0.0020 (6)	0.0053 (6)	−0.0016 (6)
C6	0.0113 (7)	0.0191 (8)	0.0155 (8)	0.0021 (6)	0.0019 (6)	0.0013 (6)
C7	0.0160 (8)	0.0174 (8)	0.0202 (8)	−0.0006 (6)	0.0008 (6)	0.0021 (7)
C8	0.0153 (7)	0.0184 (8)	0.0115 (7)	0.0004 (6)	0.0023 (6)	−0.0020 (6)
C9	0.0145 (7)	0.0181 (8)	0.0154 (8)	0.0023 (6)	0.0039 (6)	0.0004 (7)
C10	0.0106 (7)	0.0274 (9)	0.0149 (8)	−0.0004 (6)	0.0025 (6)	−0.0014 (7)
C11	0.0175 (8)	0.0230 (9)	0.0179 (8)	−0.0050 (7)	0.0058 (6)	−0.0010 (7)
C12	0.0216 (8)	0.0156 (8)	0.0171 (8)	−0.0006 (7)	0.0055 (6)	0.0029 (7)
C13	0.0178 (8)	0.0207 (8)	0.0112 (7)	0.0032 (7)	0.0027 (6)	0.0020 (6)
C14	0.0187 (8)	0.0208 (8)	0.0162 (8)	0.0030 (7)	−0.0014 (6)	−0.0027 (7)

Geometric parameters (Å, º)

Cr1—C1	2.1374 (17)	C1—C2	1.425 (2)
Cr1—C8	2.1383 (17)	C1—C6	1.427 (2)
Cr1—C2	2.1457 (17)	C1—C7	1.433 (2)
Cr1—C6	2.1477 (17)	C2—C3	1.407 (3)
Cr1—C9	2.1521 (17)	C3—C4	1.405 (3)
Cr1—C10	2.1522 (17)	C4—C5	1.412 (3)
Cr1—C13	2.1532 (17)	C5—C6	1.414 (3)
Cr1—C3	2.1553 (18)	C8—C13	1.421 (3)
Cr1—C5	2.1608 (17)	C8—C9	1.424 (2)
Cr1—C4	2.1639 (18)	C8—C14	1.434 (2)
Cr1—C11	2.1652 (18)	C9—C10	1.412 (3)
Cr1—C12	2.1665 (18)	C10—C11	1.409 (3)
N1—C7	1.152 (3)	C11—C12	1.414 (3)
N2—C14	1.152 (3)	C12—C13	1.410 (3)
C1—Cr1—C8	101.25 (7)	C1—Cr1—C12	143.52 (7)
C1—Cr1—C2	38.85 (7)	C8—Cr1—C12	69.12 (7)
C8—Cr1—C2	114.06 (7)	C2—Cr1—C12	176.34 (7)
C1—Cr1—C6	38.89 (7)	C6—Cr1—C12	110.44 (7)
C8—Cr1—C6	112.60 (7)	C9—Cr1—C12	82.15 (7)
C2—Cr1—C6	70.36 (7)	C10—Cr1—C12	68.99 (7)
C1—Cr1—C9	112.93 (7)	C13—Cr1—C12	38.10 (7)
C8—Cr1—C9	38.77 (7)	C3—Cr1—C12	138.16 (7)
C2—Cr1—C9	99.26 (7)	C5—Cr1—C12	96.21 (7)
C6—Cr1—C9	144.00 (7)	C4—Cr1—C12	107.68 (7)
C1—Cr1—C10	142.55 (7)	C11—Cr1—C12	38.11 (7)
C8—Cr1—C10	69.39 (7)	C2—C1—C6	120.34 (16)
C2—Cr1—C10	110.07 (7)	C2—C1—C7	119.57 (16)
C6—Cr1—C10	177.71 (7)	C6—C1—C7	120.05 (16)
C9—Cr1—C10	38.29 (7)	C2—C1—Cr1	70.89 (10)
C1—Cr1—C13	113.60 (7)	C6—C1—Cr1	70.94 (9)
C8—Cr1—C13	38.68 (7)	C7—C1—Cr1	129.22 (12)
C2—Cr1—C13	145.56 (7)	C3—C2—C1	119.30 (16)
C6—Cr1—C13	98.57 (7)	C3—C2—Cr1	71.28 (10)
C9—Cr1—C13	70.13 (7)	C1—C2—Cr1	70.26 (10)
C10—Cr1—C13	82.31 (7)	C4—C3—C2	120.70 (17)
C1—Cr1—C3	69.39 (7)	C4—C3—Cr1	71.34 (10)
C8—Cr1—C3	144.14 (7)	C2—C3—Cr1	70.54 (10)
C2—Cr1—C3	38.19 (7)	C3—C4—C5	120.16 (17)
C6—Cr1—C3	82.38 (7)	C3—C4—Cr1	70.68 (10)
C9—Cr1—C3	111.18 (7)	C5—C4—Cr1	70.83 (10)
C10—Cr1—C3	96.60 (7)	C4—C5—C6	120.44 (17)
C13—Cr1—C3	176.23 (7)	C4—C5—Cr1	71.07 (10)
C1—Cr1—C5	69.43 (7)	C6—C5—Cr1	70.34 (10)
C8—Cr1—C5	142.15 (7)	C5—C6—C1	119.05 (16)
C2—Cr1—C5	82.26 (7)	C5—C6—Cr1	71.35 (10)
C6—Cr1—C5	38.31 (7)	C1—C6—Cr1	70.17 (9)
C9—Cr1—C5	177.58 (7)	N1—C7—C1	178.6 (2)
C10—Cr1—C5	139.40 (7)	C13—C8—C9	120.76 (16)
C13—Cr1—C5	109.64 (7)	C13—C8—C14	119.66 (16)
C3—Cr1—C5	68.90 (7)	C9—C8—C14	119.55 (16)
C1—Cr1—C4	82.00 (7)	C13—C8—Cr1	71.23 (10)
C8—Cr1—C4	176.60 (7)	C9—C8—Cr1	71.14 (10)
C2—Cr1—C4	69.10 (7)	C14—C8—Cr1	128.85 (12)
C6—Cr1—C4	69.32 (7)	C10—C9—C8	118.91 (16)
C9—Cr1—C4	140.77 (7)	C10—C9—Cr1	70.85 (10)
C10—Cr1—C4	108.63 (7)	C8—C9—Cr1	70.09 (10)
C13—Cr1—C4	139.03 (7)	C11—C10—C9	120.67 (17)
C3—Cr1—C4	37.98 (7)	C11—C10—Cr1	71.45 (10)
C5—Cr1—C4	38.10 (7)	C9—C10—Cr1	70.85 (10)
C1—Cr1—C11	176.85 (7)	C10—C11—C12	120.05 (17)
C8—Cr1—C11	81.85 (7)	C10—C11—Cr1	70.45 (10)
C2—Cr1—C11	139.32 (7)	C12—C11—Cr1	70.99 (10)
C6—Cr1—C11	140.31 (7)	C13—C12—C11	120.41 (17)
C9—Cr1—C11	69.19 (7)	C13—C12—Cr1	70.44 (10)
C10—Cr1—C11	38.10 (7)	C11—C12—Cr1	70.90 (10)
C13—Cr1—C11	69.15 (7)	C12—C13—C8	119.20 (16)
C3—Cr1—C11	107.79 (7)	C12—C13—Cr1	71.46 (10)
C5—Cr1—C11	108.43 (7)	C8—C13—Cr1	70.10 (10)
C4—Cr1—C11	94.91 (7)	N2—C14—C8	179.8 (2)
C8—Cr1—C1—C2	114.57 (11)	C1—Cr1—C8—C13	113.87 (11)
C6—Cr1—C1—C2	−133.26 (15)	C2—Cr1—C8—C13	152.54 (10)
C9—Cr1—C1—C2	75.73 (12)	C6—Cr1—C8—C13	74.84 (11)
C10—Cr1—C1—C2	43.86 (16)	C9—Cr1—C8—C13	−133.38 (15)
C13—Cr1—C1—C2	153.15 (10)	C10—Cr1—C8—C13	−103.95 (11)
C3—Cr1—C1—C2	−29.34 (10)	C3—Cr1—C8—C13	−175.85 (11)
C5—Cr1—C1—C2	−103.68 (11)	C5—Cr1—C8—C13	43.00 (15)
C4—Cr1—C1—C2	−66.44 (11)	C4—Cr1—C8—C13	−49.1 (12)
C11—Cr1—C1—C2	−56.1 (13)	C11—Cr1—C8—C13	−66.64 (11)
C12—Cr1—C1—C2	−175.45 (12)	C12—Cr1—C8—C13	−29.41 (10)
C8—Cr1—C1—C6	−112.17 (10)	C1—Cr1—C8—C9	−112.74 (11)
C2—Cr1—C1—C6	133.26 (15)	C2—Cr1—C8—C9	−74.07 (11)
C9—Cr1—C1—C6	−151.01 (10)	C6—Cr1—C8—C9	−151.78 (10)
C10—Cr1—C1—C6	177.12 (11)	C10—Cr1—C8—C9	29.44 (10)
C13—Cr1—C1—C6	−73.59 (11)	C13—Cr1—C8—C9	133.38 (15)
C3—Cr1—C1—C6	103.92 (11)	C3—Cr1—C8—C9	−42.46 (16)
C5—Cr1—C1—C6	29.57 (10)	C5—Cr1—C8—C9	176.39 (11)
C4—Cr1—C1—C6	66.82 (11)	C4—Cr1—C8—C9	84.3 (12)
C11—Cr1—C1—C6	77.2 (13)	C11—Cr1—C8—C9	66.74 (11)
C12—Cr1—C1—C6	−42.19 (16)	C12—Cr1—C8—C9	103.97 (11)
C8—Cr1—C1—C7	1.53 (17)	C1—Cr1—C8—C14	0.46 (17)
C2—Cr1—C1—C7	−113.0 (2)	C2—Cr1—C8—C14	39.13 (18)
C6—Cr1—C1—C7	113.7 (2)	C6—Cr1—C8—C14	−38.57 (18)
C9—Cr1—C1—C7	−37.31 (18)	C9—Cr1—C8—C14	113.2 (2)
C10—Cr1—C1—C7	−69.2 (2)	C10—Cr1—C8—C14	142.64 (18)
C13—Cr1—C1—C7	40.11 (18)	C13—Cr1—C8—C14	−113.4 (2)
C3—Cr1—C1—C7	−142.38 (18)	C3—Cr1—C8—C14	70.7 (2)
C5—Cr1—C1—C7	143.28 (18)	C5—Cr1—C8—C14	−70.4 (2)
C4—Cr1—C1—C7	−179.48 (17)	C4—Cr1—C8—C14	−162.5 (11)
C11—Cr1—C1—C7	−169.1 (12)	C11—Cr1—C8—C14	179.95 (17)
C12—Cr1—C1—C7	71.5 (2)	C12—Cr1—C8—C14	−142.82 (18)
C6—C1—C2—C3	0.8 (2)	C13—C8—C9—C10	0.0 (2)
C7—C1—C2—C3	178.61 (16)	C14—C8—C9—C10	−177.87 (16)
Cr1—C1—C2—C3	53.67 (14)	Cr1—C8—C9—C10	−53.24 (14)
C6—C1—C2—Cr1	−52.90 (14)	C13—C8—C9—Cr1	53.20 (14)
C7—C1—C2—Cr1	124.95 (16)	C14—C8—C9—Cr1	−124.63 (16)
C1—Cr1—C2—C3	−132.12 (15)	C1—Cr1—C9—C10	−148.79 (11)
C8—Cr1—C2—C3	150.22 (10)	C8—Cr1—C9—C10	132.07 (16)
C6—Cr1—C2—C3	−103.07 (12)	C2—Cr1—C9—C10	−110.76 (11)
C9—Cr1—C2—C3	112.62 (11)	C6—Cr1—C9—C10	−179.97 (11)
C10—Cr1—C2—C3	74.54 (12)	C13—Cr1—C9—C10	103.19 (12)
C13—Cr1—C2—C3	−179.15 (12)	C3—Cr1—C9—C10	−73.03 (12)
C5—Cr1—C2—C3	−65.48 (11)	C5—Cr1—C9—C10	18.2 (17)
C4—Cr1—C2—C3	−28.44 (10)	C4—Cr1—C9—C10	−42.59 (16)
C11—Cr1—C2—C3	43.87 (16)	C11—Cr1—C9—C10	28.71 (11)
C12—Cr1—C2—C3	0.2 (11)	C12—Cr1—C9—C10	65.83 (11)
C8—Cr1—C2—C1	−77.66 (11)	C1—Cr1—C9—C8	79.14 (11)
C6—Cr1—C2—C1	29.05 (10)	C2—Cr1—C9—C8	117.17 (11)
C9—Cr1—C2—C1	−115.26 (11)	C6—Cr1—C9—C8	47.96 (16)
C10—Cr1—C2—C1	−153.35 (10)	C10—Cr1—C9—C8	−132.07 (16)
C13—Cr1—C2—C1	−47.03 (16)	C13—Cr1—C9—C8	−28.88 (10)
C3—Cr1—C2—C1	132.12 (15)	C3—Cr1—C9—C8	154.90 (10)
C5—Cr1—C2—C1	66.64 (11)	C5—Cr1—C9—C8	−113.8 (17)
C4—Cr1—C2—C1	103.68 (11)	C4—Cr1—C9—C8	−174.65 (11)
C11—Cr1—C2—C1	175.99 (11)	C11—Cr1—C9—C8	−103.36 (11)
C12—Cr1—C2—C1	132.3 (11)	C12—Cr1—C9—C8	−66.24 (11)
C1—C2—C3—C4	−0.4 (3)	C8—C9—C10—C11	−0.4 (3)
Cr1—C2—C3—C4	52.81 (15)	Cr1—C9—C10—C11	−53.31 (15)
C1—C2—C3—Cr1	−53.19 (14)	C8—C9—C10—Cr1	52.88 (14)
C1—Cr1—C3—C4	−103.89 (11)	C1—Cr1—C10—C11	−174.97 (11)
C8—Cr1—C3—C4	175.58 (11)	C8—Cr1—C10—C11	103.54 (12)
C2—Cr1—C3—C4	−133.70 (16)	C2—Cr1—C10—C11	−147.41 (11)
C6—Cr1—C3—C4	−65.95 (11)	C6—Cr1—C10—C11	−47.2 (18)
C9—Cr1—C3—C4	148.62 (10)	C9—Cr1—C10—C11	133.32 (16)
C10—Cr1—C3—C4	111.99 (11)	C13—Cr1—C10—C11	65.81 (11)
C13—Cr1—C3—C4	39.0 (11)	C3—Cr1—C10—C11	−110.55 (11)
C5—Cr1—C3—C4	−28.79 (10)	C5—Cr1—C10—C11	−45.52 (16)
C11—Cr1—C3—C4	74.63 (12)	C4—Cr1—C10—C11	−73.53 (12)
C12—Cr1—C3—C4	46.32 (15)	C12—Cr1—C10—C11	28.82 (11)
C1—Cr1—C3—C2	29.81 (10)	C1—Cr1—C10—C9	51.71 (16)
C8—Cr1—C3—C2	−50.72 (16)	C8—Cr1—C10—C9	−29.78 (10)
C6—Cr1—C3—C2	67.75 (11)	C2—Cr1—C10—C9	79.27 (12)
C9—Cr1—C3—C2	−77.68 (11)	C6—Cr1—C10—C9	180 (100)
C10—Cr1—C3—C2	−114.31 (11)	C13—Cr1—C10—C9	−67.51 (11)
C13—Cr1—C3—C2	172.7 (10)	C3—Cr1—C10—C9	116.13 (11)
C5—Cr1—C3—C2	104.91 (11)	C5—Cr1—C10—C9	−178.84 (11)
C4—Cr1—C3—C2	133.70 (16)	C4—Cr1—C10—C9	153.15 (11)
C11—Cr1—C3—C2	−151.67 (11)	C11—Cr1—C10—C9	−133.32 (16)
C12—Cr1—C3—C2	−179.98 (11)	C12—Cr1—C10—C9	−104.50 (12)
C2—C3—C4—C5	0.2 (3)	C9—C10—C11—C12	0.2 (3)
Cr1—C3—C4—C5	52.69 (15)	Cr1—C10—C11—C12	−52.79 (15)
C2—C3—C4—Cr1	−52.45 (15)	C9—C10—C11—Cr1	53.04 (15)
C1—Cr1—C4—C3	66.58 (11)	C1—Cr1—C11—C10	103.9 (13)
C8—Cr1—C4—C3	−130.3 (12)	C8—Cr1—C11—C10	−66.82 (11)
C2—Cr1—C4—C3	28.58 (10)	C2—Cr1—C11—C10	50.91 (15)
C6—Cr1—C4—C3	104.67 (11)	C6—Cr1—C11—C10	177.37 (11)
C9—Cr1—C4—C3	−50.16 (15)	C9—Cr1—C11—C10	−28.84 (11)
C10—Cr1—C4—C3	−76.42 (12)	C13—Cr1—C11—C10	−104.69 (12)
C13—Cr1—C4—C3	−176.38 (11)	C3—Cr1—C11—C10	77.66 (12)
C5—Cr1—C4—C3	133.27 (16)	C5—Cr1—C11—C10	150.70 (11)
C11—Cr1—C4—C3	−112.86 (11)	C4—Cr1—C11—C10	114.21 (11)
C12—Cr1—C4—C3	−149.58 (11)	C12—Cr1—C11—C10	−133.18 (16)
C1—Cr1—C4—C5	−66.70 (11)	C1—Cr1—C11—C12	−122.9 (13)
C8—Cr1—C4—C5	96.4 (12)	C8—Cr1—C11—C12	66.36 (11)
C2—Cr1—C4—C5	−104.69 (12)	C2—Cr1—C11—C12	−175.90 (11)
C6—Cr1—C4—C5	−28.61 (11)	C6—Cr1—C11—C12	−49.45 (16)
C9—Cr1—C4—C5	176.57 (11)	C9—Cr1—C11—C12	104.35 (12)
C10—Cr1—C4—C5	150.31 (11)	C10—Cr1—C11—C12	133.18 (16)
C13—Cr1—C4—C5	50.35 (15)	C13—Cr1—C11—C12	28.49 (11)
C3—Cr1—C4—C5	−133.27 (16)	C3—Cr1—C11—C12	−149.16 (11)
C11—Cr1—C4—C5	113.87 (11)	C5—Cr1—C11—C12	−76.12 (12)
C12—Cr1—C4—C5	77.15 (12)	C4—Cr1—C11—C12	−112.61 (11)
C3—C4—C5—C6	−0.5 (3)	C10—C11—C12—C13	0.4 (3)
Cr1—C4—C5—C6	52.12 (15)	Cr1—C11—C12—C13	−52.12 (15)
C3—C4—C5—Cr1	−52.62 (15)	C10—C11—C12—Cr1	52.54 (15)
C1—Cr1—C5—C4	103.74 (12)	C1—Cr1—C12—C13	−50.70 (16)
C8—Cr1—C5—C4	−174.50 (11)	C8—Cr1—C12—C13	29.82 (10)
C2—Cr1—C5—C4	65.78 (11)	C2—Cr1—C12—C13	−179 (57)
C6—Cr1—C5—C4	133.73 (16)	C6—Cr1—C12—C13	−77.44 (12)
C9—Cr1—C5—C4	−63.5 (17)	C9—Cr1—C12—C13	67.66 (11)
C10—Cr1—C5—C4	−46.16 (16)	C10—Cr1—C12—C13	104.93 (12)
C13—Cr1—C5—C4	−147.59 (11)	C3—Cr1—C12—C13	−179.22 (11)
C3—Cr1—C5—C4	28.70 (11)	C5—Cr1—C12—C13	−114.14 (11)
C11—Cr1—C5—C4	−73.81 (12)	C4—Cr1—C12—C13	−151.38 (11)
C12—Cr1—C5—C4	−110.87 (11)	C11—Cr1—C12—C13	133.75 (16)
C1—Cr1—C5—C6	−29.99 (10)	C1—Cr1—C12—C11	175.55 (11)
C8—Cr1—C5—C6	51.77 (16)	C8—Cr1—C12—C11	−103.93 (12)
C2—Cr1—C5—C6	−67.95 (11)	C2—Cr1—C12—C11	46.9 (11)
C9—Cr1—C5—C6	162.8 (16)	C6—Cr1—C12—C11	148.81 (11)
C10—Cr1—C5—C6	−179.89 (11)	C9—Cr1—C12—C11	−66.09 (11)
C13—Cr1—C5—C6	78.68 (12)	C10—Cr1—C12—C11	−28.82 (11)
C3—Cr1—C5—C6	−105.03 (12)	C13—Cr1—C12—C11	−133.75 (16)
C4—Cr1—C5—C6	−133.73 (16)	C3—Cr1—C12—C11	47.03 (15)
C11—Cr1—C5—C6	152.46 (11)	C5—Cr1—C12—C11	112.11 (11)
C12—Cr1—C5—C6	115.40 (11)	C4—Cr1—C12—C11	74.87 (12)
C4—C5—C6—C1	0.9 (3)	C11—C12—C13—C8	−0.9 (3)
Cr1—C5—C6—C1	53.34 (14)	Cr1—C12—C13—C8	−53.21 (14)
C4—C5—C6—Cr1	−52.44 (15)	C11—C12—C13—Cr1	52.32 (15)
C2—C1—C6—C5	−1.0 (2)	C9—C8—C13—C12	0.7 (3)
C7—C1—C6—C5	−178.86 (16)	C14—C8—C13—C12	178.52 (16)
Cr1—C1—C6—C5	−53.90 (14)	Cr1—C8—C13—C12	53.86 (15)
C2—C1—C6—Cr1	52.87 (14)	C9—C8—C13—Cr1	−53.16 (14)
C7—C1—C6—Cr1	−124.96 (16)	C14—C8—C13—Cr1	124.67 (16)
C1—Cr1—C6—C5	131.80 (15)	C1—Cr1—C13—C12	149.87 (11)
C8—Cr1—C6—C5	−148.53 (11)	C8—Cr1—C13—C12	−131.97 (15)
C2—Cr1—C6—C5	102.78 (12)	C2—Cr1—C13—C12	179.93 (12)
C9—Cr1—C6—C5	−178.78 (12)	C6—Cr1—C13—C12	112.34 (11)
C10—Cr1—C6—C5	1.7 (18)	C9—Cr1—C13—C12	−103.03 (12)
C13—Cr1—C6—C5	−110.94 (11)	C10—Cr1—C13—C12	−65.53 (11)
C3—Cr1—C6—C5	65.37 (11)	C3—Cr1—C13—C12	7.9 (11)
C4—Cr1—C6—C5	28.46 (11)	C5—Cr1—C13—C12	74.41 (12)
C11—Cr1—C6—C5	−43.39 (16)	C4—Cr1—C13—C12	44.12 (15)
C12—Cr1—C6—C5	−73.42 (12)	C11—Cr1—C13—C12	−28.49 (11)
C8—Cr1—C6—C1	79.67 (11)	C1—Cr1—C13—C8	−78.17 (11)
C2—Cr1—C6—C1	−29.02 (10)	C2—Cr1—C13—C8	−48.10 (16)
C9—Cr1—C6—C1	49.42 (16)	C6—Cr1—C13—C8	−115.69 (10)
C10—Cr1—C6—C1	−130.1 (17)	C9—Cr1—C13—C8	28.94 (10)
C13—Cr1—C6—C1	117.26 (11)	C10—Cr1—C13—C8	66.44 (11)
C3—Cr1—C6—C1	−66.43 (11)	C3—Cr1—C13—C8	139.9 (10)
C5—Cr1—C6—C1	−131.80 (15)	C5—Cr1—C13—C8	−153.62 (10)
C4—Cr1—C6—C1	−103.34 (11)	C4—Cr1—C13—C8	176.09 (10)
C11—Cr1—C6—C1	−175.19 (11)	C11—Cr1—C13—C8	103.48 (11)
C12—Cr1—C6—C1	154.78 (10)	C12—Cr1—C13—C8	131.97 (15)
C2—C1—C7—N1	63 (8)	C13—C8—C14—N2	140 (100)
C6—C1—C7—N1	−119 (8)	C9—C8—C14—N2	−42 (64)
Cr1—C1—C7—N1	152 (8)	Cr1—C8—C14—N2	−131 (100)

(3)

Crystal data

C14H13CrN	Dx = 1.541 Mg m^−3
Mr = 247.25	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 2085 reflections
a = 12.9628 (19) Å	θ = 3.0–28.8°
b = 12.0803 (18) Å	µ = 1.04 mm^−1
c = 13.610 (2) Å	T = 120 K
V = 2131.3 (5) Å^3	Prism, brown
Z = 8	0.24 × 0.21 × 0.12 mm
F(000) = 1024

Data collection

Bruker SMART 1000 CCD area detector diffractometer	2318 independent reflections
Radiation source: normal-focus sealed tube	1353 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
phi and ω scans	θmax = 27.0°, θmin = 2.8°
Absorption correction: multi-scan SADABS (Sheldrick, 1998a)	h = −15→16
Tmin = 0.788, Tmax = 0.885	k = −15→15
15653 measured reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	Hydrogen site location: difference Fourier map
wR(F^2) = 0.143	All H-atom parameters refined
S = 1.05	w = 1/[σ^2(Fo^2) + (0.070P)^2 + 1.5P] where P = (Fo^2 + 2Fc^2)/3
2318 reflections	(Δ/σ)max = 0.001
197 parameters	Δρmax = 1.79 e Å^−3
0 restraints	Δρmin = −0.77 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.

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
Cr1	0.02733 (4)	0.75470 (4)	0.43790 (4)	0.0212 (2)
N1	0.2266 (2)	0.5167 (3)	0.5709 (2)	0.0384 (8)
C1	0.0901 (3)	0.6728 (3)	0.5620 (3)	0.0220 (7)
C2	0.1205 (3)	0.7856 (3)	0.5645 (3)	0.0243 (7)
C3	0.0457 (3)	0.8684 (3)	0.5580 (3)	0.0264 (8)
C4	−0.0586 (3)	0.8408 (3)	0.5476 (3)	0.0292 (9)
C5	−0.0895 (3)	0.7292 (3)	0.5472 (3)	0.0273 (9)
C6	−0.0154 (3)	0.6443 (3)	0.5533 (3)	0.0256 (8)
C7	0.1664 (3)	0.5863 (3)	0.5669 (3)	0.0277 (8)
C8	0.1099 (3)	0.6736 (3)	0.3179 (2)	0.0265 (8)
C9	0.1378 (3)	0.7857 (3)	0.3223 (2)	0.0301 (9)
C10	0.0623 (4)	0.8695 (3)	0.3222 (3)	0.0338 (9)
C11	−0.0409 (3)	0.8426 (4)	0.3175 (3)	0.0375 (11)
C12	−0.0719 (3)	0.7315 (4)	0.3146 (3)	0.0334 (10)
C13	0.0037 (3)	0.6466 (3)	0.3156 (3)	0.0291 (9)
C14	0.1907 (3)	0.5844 (3)	0.3142 (3)	0.0357 (9)
H2	0.205 (4)	0.802 (4)	0.571 (3)	0.069 (15)*
H3	0.066 (3)	0.944 (3)	0.560 (3)	0.036 (10)*
H4	−0.105 (3)	0.901 (3)	0.539 (2)	0.033 (10)*
H5	−0.153 (3)	0.713 (3)	0.537 (3)	0.026 (10)*
H6	−0.039 (3)	0.571 (3)	0.548 (3)	0.034 (11)*
H9	0.210 (3)	0.800 (4)	0.333 (3)	0.054 (14)*
H10	0.093 (3)	0.953 (4)	0.336 (3)	0.057 (13)*
H11	−0.093 (3)	0.902 (3)	0.319 (3)	0.045 (12)*
H12	−0.129 (3)	0.717 (3)	0.316 (3)	0.025 (11)*
H13	−0.020 (3)	0.579 (3)	0.317 (2)	0.021 (10)*
H14A	0.208 (3)	0.563 (3)	0.243 (3)	0.044 (12)*
H14B	0.164 (3)	0.512 (3)	0.346 (3)	0.050 (12)*
H14C	0.254 (4)	0.606 (4)	0.355 (4)	0.089 (17)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cr1	0.0199 (3)	0.0241 (3)	0.0196 (3)	0.0007 (2)	−0.0008 (2)	0.0005 (2)
N1	0.0333 (18)	0.0333 (18)	0.049 (2)	0.0032 (15)	−0.0030 (16)	0.0055 (16)
C1	0.0251 (18)	0.0211 (16)	0.0198 (16)	0.0048 (14)	−0.0013 (15)	0.0010 (15)
C2	0.0259 (19)	0.0268 (17)	0.0202 (16)	−0.0049 (14)	−0.0044 (16)	−0.0005 (18)
C3	0.034 (2)	0.0189 (17)	0.0260 (18)	−0.0022 (15)	0.0005 (17)	−0.0029 (16)
C4	0.032 (2)	0.030 (2)	0.026 (2)	0.0090 (17)	0.0062 (16)	0.0001 (16)
C5	0.0172 (17)	0.038 (2)	0.026 (2)	−0.0021 (16)	0.0034 (15)	0.0011 (16)
C6	0.031 (2)	0.0218 (18)	0.0245 (19)	−0.0051 (15)	0.0030 (16)	0.0011 (16)
C7	0.0262 (19)	0.0258 (19)	0.0310 (19)	0.0006 (15)	−0.0025 (16)	0.0056 (17)
C8	0.030 (2)	0.034 (2)	0.0156 (17)	0.0078 (16)	0.0016 (14)	−0.0041 (15)
C9	0.031 (2)	0.040 (2)	0.0198 (18)	−0.0074 (18)	0.0038 (16)	0.0004 (18)
C10	0.049 (3)	0.030 (2)	0.023 (2)	−0.0011 (19)	0.0021 (18)	0.0048 (16)
C11	0.052 (3)	0.042 (3)	0.018 (2)	0.016 (2)	−0.0057 (18)	0.0012 (18)
C12	0.0222 (19)	0.057 (3)	0.0206 (17)	−0.006 (2)	−0.0076 (18)	−0.0013 (19)
C13	0.042 (2)	0.025 (2)	0.021 (2)	−0.0060 (18)	−0.0032 (17)	−0.0027 (16)
C14	0.037 (2)	0.034 (2)	0.036 (2)	0.0043 (18)	0.0063 (19)	−0.003 (2)

Geometric parameters (Å, º)

Cr1—C1	2.120 (3)	C1—C2	1.419 (5)
Cr1—C4	2.133 (4)	C1—C7	1.440 (5)
Cr1—C12	2.133 (4)	C2—C3	1.396 (5)
Cr1—C6	2.133 (4)	C3—C4	1.400 (5)
Cr1—C2	2.138 (3)	C4—C5	1.406 (5)
Cr1—C13	2.138 (4)	C5—C6	1.407 (5)
Cr1—C11	2.144 (4)	C8—C9	1.403 (6)
Cr1—C5	2.145 (4)	C8—C13	1.416 (5)
Cr1—C10	2.146 (4)	C8—C14	1.503 (5)
Cr1—C3	2.149 (4)	C9—C10	1.409 (6)
Cr1—C9	2.160 (4)	C10—C11	1.378 (6)
Cr1—C8	2.185 (3)	C11—C12	1.401 (6)
N1—C7	1.148 (4)	C12—C13	1.418 (6)
C1—C6	1.416 (5)
C1—Cr1—C4	82.55 (14)	C1—Cr1—C8	101.45 (12)
C1—Cr1—C12	142.87 (15)	C4—Cr1—C8	176.00 (14)
C4—Cr1—C12	107.45 (16)	C12—Cr1—C8	69.40 (15)
C1—Cr1—C6	38.88 (14)	C6—Cr1—C8	113.40 (14)
C4—Cr1—C6	69.76 (15)	C2—Cr1—C8	113.84 (14)
C12—Cr1—C6	109.91 (16)	C13—Cr1—C8	38.22 (14)
C1—Cr1—C2	38.94 (13)	C11—Cr1—C8	81.52 (15)
C4—Cr1—C2	69.26 (15)	C5—Cr1—C8	143.13 (15)
C12—Cr1—C2	176.52 (15)	C10—Cr1—C8	68.77 (15)
C6—Cr1—C2	70.29 (14)	C3—Cr1—C8	143.25 (14)
C1—Cr1—C13	112.98 (14)	C9—Cr1—C8	37.66 (15)
C4—Cr1—C13	140.14 (16)	C6—C1—C2	120.3 (3)
C12—Cr1—C13	38.80 (16)	C6—C1—C7	119.4 (3)
C6—Cr1—C13	98.85 (14)	C2—C1—C7	120.3 (3)
C2—Cr1—C13	144.65 (15)	C6—C1—Cr1	71.1 (2)
C1—Cr1—C11	177.03 (15)	C2—C1—Cr1	71.2 (2)
C4—Cr1—C11	94.48 (15)	C7—C1—Cr1	129.7 (3)
C12—Cr1—C11	38.24 (16)	C3—C2—C1	119.6 (3)
C6—Cr1—C11	139.92 (16)	C3—C2—Cr1	71.4 (2)
C2—Cr1—C11	139.73 (16)	C1—C2—Cr1	69.87 (19)
C13—Cr1—C11	69.40 (17)	C2—C3—C4	120.4 (3)
C1—Cr1—C5	69.58 (14)	C2—C3—Cr1	70.6 (2)
C4—Cr1—C5	38.37 (14)	C4—C3—Cr1	70.3 (2)
C12—Cr1—C5	95.83 (16)	C3—C4—C5	120.3 (3)
C6—Cr1—C5	38.40 (14)	C3—C4—Cr1	71.5 (2)
C2—Cr1—C5	82.23 (15)	C5—C4—Cr1	71.3 (2)
C13—Cr1—C5	110.55 (16)	C4—C5—C6	120.3 (3)
C11—Cr1—C5	108.08 (16)	C4—C5—Cr1	70.3 (2)
C1—Cr1—C10	143.60 (15)	C6—C5—Cr1	70.3 (2)
C4—Cr1—C10	107.97 (15)	C5—C6—C1	119.1 (3)
C12—Cr1—C10	68.58 (17)	C5—C6—Cr1	71.3 (2)
C6—Cr1—C10	176.96 (16)	C1—C6—Cr1	70.05 (19)
C2—Cr1—C10	111.04 (15)	N1—C7—C1	179.4 (4)
C13—Cr1—C10	81.61 (16)	C9—C8—C13	118.3 (3)
C11—Cr1—C10	37.48 (16)	C9—C8—C14	120.9 (3)
C5—Cr1—C10	138.64 (16)	C13—C8—C14	120.8 (4)
C1—Cr1—C3	69.49 (13)	C9—C8—Cr1	70.2 (2)
C4—Cr1—C3	38.17 (14)	C13—C8—Cr1	69.1 (2)
C12—Cr1—C3	138.54 (15)	C14—C8—Cr1	133.4 (3)
C6—Cr1—C3	82.45 (15)	C8—C9—C10	121.0 (4)
C2—Cr1—C3	38.02 (13)	C8—C9—Cr1	72.2 (2)
C13—Cr1—C3	177.31 (15)	C10—C9—Cr1	70.4 (2)
C11—Cr1—C3	108.10 (16)	C11—C10—C9	120.3 (4)
C5—Cr1—C3	69.04 (14)	C11—C10—Cr1	71.2 (2)
C10—Cr1—C3	96.97 (14)	C9—C10—Cr1	71.4 (2)
C1—Cr1—C9	113.99 (14)	C10—C11—C12	120.4 (4)
C4—Cr1—C9	140.48 (16)	C10—C11—Cr1	71.4 (2)
C12—Cr1—C9	81.34 (17)	C12—C11—Cr1	70.5 (2)
C6—Cr1—C9	144.74 (15)	C11—C12—C13	119.6 (4)
C2—Cr1—C9	100.49 (15)	C11—C12—Cr1	71.3 (2)
C13—Cr1—C9	68.53 (15)	C13—C12—Cr1	70.8 (2)
C11—Cr1—C9	68.35 (16)	C8—C13—C12	120.3 (4)
C5—Cr1—C9	176.43 (15)	C8—C13—Cr1	72.7 (2)
C10—Cr1—C9	38.19 (15)	C12—C13—Cr1	70.4 (2)
C3—Cr1—C9	111.70 (15)
C4—Cr1—C1—C6	66.8 (2)	Cr1—C1—C7—N1	−98 (37)
C12—Cr1—C1—C6	−42.3 (3)	C1—Cr1—C8—C9	−114.6 (2)
C2—Cr1—C1—C6	132.8 (3)	C4—Cr1—C8—C9	65 (2)
C13—Cr1—C1—C6	−74.9 (2)	C12—Cr1—C8—C9	102.9 (3)
C11—Cr1—C1—C6	68 (3)	C6—Cr1—C8—C9	−153.6 (2)
C5—Cr1—C1—C6	29.5 (2)	C2—Cr1—C8—C9	−75.7 (2)
C10—Cr1—C1—C6	177.1 (2)	C13—Cr1—C8—C9	132.6 (3)
C3—Cr1—C1—C6	103.9 (2)	C11—Cr1—C8—C9	65.3 (2)
C9—Cr1—C1—C6	−150.7 (2)	C5—Cr1—C8—C9	174.2 (2)
C8—Cr1—C1—C6	−113.2 (2)	C10—Cr1—C8—C9	28.7 (2)
C4—Cr1—C1—C2	−66.0 (2)	C3—Cr1—C8—C9	−43.7 (3)
C12—Cr1—C1—C2	−175.2 (3)	C1—Cr1—C8—C13	112.7 (2)
C6—Cr1—C1—C2	−132.8 (3)	C4—Cr1—C8—C13	−68 (2)
C13—Cr1—C1—C2	152.2 (2)	C12—Cr1—C8—C13	−29.7 (2)
C11—Cr1—C1—C2	−65 (3)	C6—Cr1—C8—C13	73.8 (2)
C5—Cr1—C1—C2	−103.4 (2)	C2—Cr1—C8—C13	151.7 (2)
C10—Cr1—C1—C2	44.3 (3)	C11—Cr1—C8—C13	−67.3 (2)
C3—Cr1—C1—C2	−28.9 (2)	C5—Cr1—C8—C13	41.6 (3)
C9—Cr1—C1—C2	76.5 (2)	C10—Cr1—C8—C13	−103.9 (2)
C8—Cr1—C1—C2	113.9 (2)	C3—Cr1—C8—C13	−176.3 (2)
C4—Cr1—C1—C7	179.8 (3)	C9—Cr1—C8—C13	−132.6 (3)
C12—Cr1—C1—C7	70.6 (4)	C1—Cr1—C8—C14	−0.4 (4)
C6—Cr1—C1—C7	113.0 (4)	C4—Cr1—C8—C14	179 (85)
C2—Cr1—C1—C7	−114.2 (4)	C12—Cr1—C8—C14	−142.8 (4)
C13—Cr1—C1—C7	38.0 (4)	C6—Cr1—C8—C14	−39.3 (4)
C11—Cr1—C1—C7	−179 (100)	C2—Cr1—C8—C14	38.6 (4)
C5—Cr1—C1—C7	142.4 (3)	C13—Cr1—C8—C14	−113.1 (5)
C10—Cr1—C1—C7	−69.9 (4)	C11—Cr1—C8—C14	179.6 (4)
C3—Cr1—C1—C7	−143.1 (3)	C5—Cr1—C8—C14	−71.5 (5)
C9—Cr1—C1—C7	−37.7 (4)	C10—Cr1—C8—C14	143.0 (4)
C8—Cr1—C1—C7	−0.3 (3)	C3—Cr1—C8—C14	70.6 (5)
C6—C1—C2—C3	−0.2 (5)	C9—Cr1—C8—C14	114.3 (5)
C7—C1—C2—C3	178.9 (4)	C13—C8—C9—C10	−1.5 (5)
Cr1—C1—C2—C3	53.3 (3)	C14—C8—C9—C10	177.7 (3)
C6—C1—C2—Cr1	−53.4 (3)	Cr1—C8—C9—C10	−52.8 (3)
C7—C1—C2—Cr1	125.6 (3)	C13—C8—C9—Cr1	51.3 (3)
C1—Cr1—C2—C3	−132.7 (3)	C14—C8—C9—Cr1	−129.5 (3)
C4—Cr1—C2—C3	−28.3 (2)	C1—Cr1—C9—C8	77.2 (2)
C12—Cr1—C2—C3	−9 (3)	C4—Cr1—C9—C8	−174.3 (2)
C6—Cr1—C2—C3	−103.4 (2)	C12—Cr1—C9—C8	−67.4 (2)
C13—Cr1—C2—C3	179.5 (2)	C6—Cr1—C9—C8	45.1 (4)
C11—Cr1—C2—C3	43.2 (3)	C2—Cr1—C9—C8	115.7 (2)
C5—Cr1—C2—C3	−65.7 (2)	C13—Cr1—C9—C8	−29.3 (2)
C10—Cr1—C2—C3	73.7 (2)	C11—Cr1—C9—C8	−104.8 (3)
C9—Cr1—C2—C3	112.0 (2)	C5—Cr1—C9—C8	−105 (2)
C8—Cr1—C2—C3	149.0 (2)	C10—Cr1—C9—C8	−133.5 (3)
C4—Cr1—C2—C1	104.4 (2)	C3—Cr1—C9—C8	153.6 (2)
C12—Cr1—C2—C1	123 (3)	C1—Cr1—C9—C10	−149.2 (2)
C6—Cr1—C2—C1	29.3 (2)	C4—Cr1—C9—C10	−40.8 (4)
C13—Cr1—C2—C1	−47.9 (3)	C12—Cr1—C9—C10	66.2 (2)
C11—Cr1—C2—C1	175.8 (2)	C6—Cr1—C9—C10	178.6 (3)
C5—Cr1—C2—C1	67.0 (2)	C2—Cr1—C9—C10	−110.8 (2)
C10—Cr1—C2—C1	−153.7 (2)	C13—Cr1—C9—C10	104.3 (3)
C3—Cr1—C2—C1	132.7 (3)	C11—Cr1—C9—C10	28.8 (2)
C9—Cr1—C2—C1	−115.4 (2)	C5—Cr1—C9—C10	28 (3)
C8—Cr1—C2—C1	−78.4 (2)	C3—Cr1—C9—C10	−72.9 (3)
C1—C2—C3—C4	−1.0 (6)	C8—Cr1—C9—C10	133.5 (3)
Cr1—C2—C3—C4	51.6 (3)	C8—C9—C10—C11	−0.1 (5)
C1—C2—C3—Cr1	−52.5 (3)	Cr1—C9—C10—C11	−53.7 (3)
C1—Cr1—C3—C2	29.6 (2)	C8—C9—C10—Cr1	53.6 (3)
C4—Cr1—C3—C2	134.2 (3)	C1—Cr1—C10—C11	−175.4 (2)
C12—Cr1—C3—C2	179.1 (2)	C4—Cr1—C10—C11	−73.3 (3)
C6—Cr1—C3—C2	67.5 (2)	C12—Cr1—C10—C11	28.9 (2)
C13—Cr1—C3—C2	−173 (3)	C6—Cr1—C10—C11	−32 (3)
C11—Cr1—C3—C2	−152.3 (2)	C2—Cr1—C10—C11	−147.3 (2)
C5—Cr1—C3—C2	104.8 (2)	C13—Cr1—C10—C11	66.9 (3)
C10—Cr1—C3—C2	−115.5 (2)	C5—Cr1—C10—C11	−44.8 (3)
C9—Cr1—C3—C2	−79.0 (2)	C3—Cr1—C10—C11	−110.8 (3)
C8—Cr1—C3—C2	−52.0 (3)	C9—Cr1—C10—C11	132.6 (4)
C1—Cr1—C3—C4	−104.6 (2)	C8—Cr1—C10—C11	104.3 (3)
C12—Cr1—C3—C4	45.0 (3)	C1—Cr1—C10—C9	52.0 (3)
C6—Cr1—C3—C4	−66.7 (2)	C4—Cr1—C10—C9	154.1 (2)
C2—Cr1—C3—C4	−134.2 (3)	C12—Cr1—C10—C9	−103.7 (3)
C13—Cr1—C3—C4	52 (3)	C6—Cr1—C10—C9	−165 (3)
C11—Cr1—C3—C4	73.6 (3)	C2—Cr1—C10—C9	80.0 (3)
C5—Cr1—C3—C4	−29.4 (2)	C13—Cr1—C10—C9	−65.7 (2)
C10—Cr1—C3—C4	110.3 (2)	C11—Cr1—C10—C9	−132.6 (4)
C9—Cr1—C3—C4	146.8 (2)	C5—Cr1—C10—C9	−177.4 (2)
C8—Cr1—C3—C4	173.8 (2)	C3—Cr1—C10—C9	116.6 (2)
C2—C3—C4—C5	2.4 (6)	C8—Cr1—C10—C9	−28.4 (2)
Cr1—C3—C4—C5	54.1 (3)	C9—C10—C11—C12	1.2 (6)
C2—C3—C4—Cr1	−51.7 (3)	Cr1—C10—C11—C12	−52.7 (3)
C1—Cr1—C4—C3	66.1 (2)	C9—C10—C11—Cr1	53.9 (3)
C12—Cr1—C4—C3	−150.6 (2)	C1—Cr1—C11—C10	113 (3)
C6—Cr1—C4—C3	104.0 (2)	C4—Cr1—C11—C10	114.0 (3)
C2—Cr1—C4—C3	28.2 (2)	C12—Cr1—C11—C10	−133.3 (4)
C13—Cr1—C4—C3	−176.7 (2)	C6—Cr1—C11—C10	177.5 (2)
C11—Cr1—C4—C3	−113.9 (2)	C2—Cr1—C11—C10	51.2 (3)
C5—Cr1—C4—C3	132.4 (3)	C13—Cr1—C11—C10	−103.5 (3)
C10—Cr1—C4—C3	−78.1 (2)	C5—Cr1—C11—C10	150.7 (2)
C9—Cr1—C4—C3	−53.0 (3)	C3—Cr1—C11—C10	77.5 (3)
C8—Cr1—C4—C3	−113 (2)	C9—Cr1—C11—C10	−29.3 (2)
C1—Cr1—C4—C5	−66.3 (2)	C8—Cr1—C11—C10	−66.0 (3)
C12—Cr1—C4—C5	77.0 (3)	C1—Cr1—C11—C12	−114 (3)
C6—Cr1—C4—C5	−28.4 (2)	C4—Cr1—C11—C12	−112.7 (3)
C2—Cr1—C4—C5	−104.2 (2)	C6—Cr1—C11—C12	−49.2 (4)
C13—Cr1—C4—C5	50.9 (3)	C2—Cr1—C11—C12	−175.5 (2)
C11—Cr1—C4—C5	113.7 (3)	C13—Cr1—C11—C12	29.7 (2)
C10—Cr1—C4—C5	149.5 (2)	C5—Cr1—C11—C12	−76.0 (3)
C3—Cr1—C4—C5	−132.4 (3)	C10—Cr1—C11—C12	133.3 (4)
C9—Cr1—C4—C5	174.6 (2)	C3—Cr1—C11—C12	−149.2 (2)
C8—Cr1—C4—C5	115 (2)	C9—Cr1—C11—C12	104.0 (3)
C3—C4—C5—C6	−2.7 (5)	C8—Cr1—C11—C12	67.3 (3)
Cr1—C4—C5—C6	51.5 (3)	C10—C11—C12—C13	−0.6 (6)
C3—C4—C5—Cr1	−54.2 (3)	Cr1—C11—C12—C13	−53.6 (3)
C1—Cr1—C5—C4	104.3 (2)	C10—C11—C12—Cr1	53.1 (3)
C12—Cr1—C5—C4	−110.9 (2)	C1—Cr1—C12—C11	175.5 (2)
C6—Cr1—C5—C4	134.1 (3)	C4—Cr1—C12—C11	74.5 (3)
C2—Cr1—C5—C4	66.2 (2)	C6—Cr1—C12—C11	148.8 (2)
C13—Cr1—C5—C4	−147.9 (2)	C2—Cr1—C12—C11	56 (3)
C11—Cr1—C5—C4	−73.7 (3)	C13—Cr1—C12—C11	−132.2 (4)
C10—Cr1—C5—C4	−46.9 (3)	C5—Cr1—C12—C11	112.0 (3)
C3—Cr1—C5—C4	29.3 (2)	C10—Cr1—C12—C11	−28.4 (2)
C9—Cr1—C5—C4	−73 (2)	C3—Cr1—C12—C11	47.3 (4)
C8—Cr1—C5—C4	−173.9 (2)	C9—Cr1—C12—C11	−65.8 (3)
C1—Cr1—C5—C6	−29.8 (2)	C8—Cr1—C12—C11	−102.9 (3)
C4—Cr1—C5—C6	−134.1 (3)	C1—Cr1—C12—C13	−52.4 (4)
C12—Cr1—C5—C6	115.0 (2)	C4—Cr1—C12—C13	−153.3 (2)
C2—Cr1—C5—C6	−67.9 (2)	C6—Cr1—C12—C13	−79.1 (3)
C13—Cr1—C5—C6	78.0 (2)	C2—Cr1—C12—C13	−172 (2)
C11—Cr1—C5—C6	152.1 (2)	C11—Cr1—C12—C13	132.2 (4)
C10—Cr1—C5—C6	178.9 (2)	C5—Cr1—C12—C13	−115.9 (2)
C3—Cr1—C5—C6	−104.9 (2)	C10—Cr1—C12—C13	103.8 (3)
C9—Cr1—C5—C6	152 (2)	C3—Cr1—C12—C13	179.4 (2)
C8—Cr1—C5—C6	51.9 (3)	C9—Cr1—C12—C13	66.3 (2)
C4—C5—C6—C1	1.5 (5)	C8—Cr1—C12—C13	29.3 (2)
Cr1—C5—C6—C1	53.0 (3)	C9—C8—C13—C12	2.1 (5)
C4—C5—C6—Cr1	−51.5 (3)	C14—C8—C13—C12	−177.1 (3)
C2—C1—C6—C5	−0.1 (5)	Cr1—C8—C13—C12	53.9 (3)
C7—C1—C6—C5	−179.2 (3)	C9—C8—C13—Cr1	−51.8 (3)
Cr1—C1—C6—C5	−53.6 (3)	C14—C8—C13—Cr1	129.0 (3)
C2—C1—C6—Cr1	53.5 (3)	C11—C12—C13—C8	−1.1 (6)
C7—C1—C6—Cr1	−125.6 (3)	Cr1—C12—C13—C8	−55.0 (3)
C1—Cr1—C6—C5	132.1 (3)	C11—C12—C13—Cr1	53.9 (3)
C4—Cr1—C6—C5	28.3 (2)	C1—Cr1—C13—C8	−79.0 (2)
C12—Cr1—C6—C5	−73.6 (2)	C4—Cr1—C13—C8	174.2 (2)
C2—Cr1—C6—C5	102.8 (2)	C12—Cr1—C13—C8	132.2 (3)
C13—Cr1—C6—C5	−112.1 (2)	C6—Cr1—C13—C8	−116.9 (2)
C11—Cr1—C6—C5	−43.7 (3)	C2—Cr1—C13—C8	−48.6 (3)
C10—Cr1—C6—C5	−14 (3)	C11—Cr1—C13—C8	102.9 (2)
C3—Cr1—C6—C5	65.6 (2)	C5—Cr1—C13—C8	−154.8 (2)
C9—Cr1—C6—C5	−177.1 (3)	C10—Cr1—C13—C8	66.2 (2)
C8—Cr1—C6—C5	−149.0 (2)	C3—Cr1—C13—C8	124 (3)
C4—Cr1—C6—C1	−103.7 (2)	C9—Cr1—C13—C8	28.9 (2)
C12—Cr1—C6—C1	154.4 (2)	C1—Cr1—C13—C12	148.7 (2)
C2—Cr1—C6—C1	−29.3 (2)	C4—Cr1—C13—C12	42.0 (4)
C13—Cr1—C6—C1	115.9 (2)	C6—Cr1—C13—C12	110.9 (3)
C11—Cr1—C6—C1	−175.7 (2)	C2—Cr1—C13—C12	179.1 (3)
C5—Cr1—C6—C1	−132.1 (3)	C11—Cr1—C13—C12	−29.3 (2)
C10—Cr1—C6—C1	−146 (3)	C5—Cr1—C13—C12	73.0 (3)
C3—Cr1—C6—C1	−66.5 (2)	C10—Cr1—C13—C12	−66.1 (3)
C9—Cr1—C6—C1	50.8 (3)	C3—Cr1—C13—C12	−8 (3)
C8—Cr1—C6—C1	78.9 (2)	C9—Cr1—C13—C12	−103.3 (3)
C6—C1—C7—N1	−9 (37)	C8—Cr1—C13—C12	−132.2 (3)
C2—C1—C7—N1	172 (100)

(4)

Crystal data

C14H10CrF3N	F(000) = 608
Mr = 301.23	Dx = 1.690 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.7145 (13) Å	Cell parameters from 5825 reflections
b = 7.8227 (11) Å	θ = 2.3–30.0°
c = 15.740 (2) Å	µ = 0.99 mm^−1
β = 98.276 (4)°	T = 120 K
V = 1183.7 (3) Å^3	Prism, dark brown
Z = 4	0.40 × 0.30 × 0.30 mm

Data collection

Bruker SMART 1000 CCD area detector diffractometer	3386 independent reflections
Radiation source: normal-focus sealed tube	2915 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
phi and ω scans	θmax = 30.0°, θmin = 2.1°
Absorption correction: multi-scan SADABS (Sheldrick, 1998a)	h = −13→13
Tmin = 0.693, Tmax = 0.756	k = −10→10
9037 measured reflections	l = −22→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	All H-atom parameters refined
wR(F^2) = 0.106	w = 1/[σ^2(Fo^2) + (0.060P)^2 + 1.2P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
3386 reflections	Δρmax = 0.77 e Å^−3
213 parameters	Δρmin = −0.80 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.034 (2)

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
Cr1	0.23976 (3)	0.78584 (3)	0.159876 (16)	0.01590 (11)
F1	0.64882 (12)	0.6413 (2)	0.08990 (9)	0.0384 (3)
F2	0.56491 (14)	0.89709 (17)	0.08127 (8)	0.0352 (3)
F3	0.47221 (13)	0.70009 (17)	−0.00357 (8)	0.0309 (3)
N1	0.0822 (2)	0.6483 (3)	−0.09338 (11)	0.0347 (4)
C1	0.10681 (18)	0.8344 (2)	0.04372 (11)	0.0212 (3)
C2	0.02336 (18)	0.7971 (2)	0.10911 (12)	0.0235 (4)
C3	0.0461 (2)	0.8913 (3)	0.18630 (13)	0.0293 (4)
C4	0.1504 (2)	1.0177 (3)	0.19988 (14)	0.0321 (4)
C5	0.2311 (2)	1.0566 (2)	0.13388 (15)	0.0299 (4)
C6	0.20944 (19)	0.9658 (2)	0.05590 (12)	0.0244 (4)
C7	0.09272 (19)	0.7303 (3)	−0.03259 (12)	0.0242 (4)
C8	0.43493 (17)	0.6854 (2)	0.14121 (11)	0.0177 (3)
C9	0.33359 (17)	0.5544 (2)	0.12301 (11)	0.0180 (3)
C10	0.24465 (17)	0.5155 (2)	0.18354 (12)	0.0198 (3)
C11	0.25856 (18)	0.6043 (2)	0.26328 (11)	0.0215 (3)
C12	0.36271 (19)	0.7299 (2)	0.28213 (11)	0.0214 (3)
C13	0.45068 (17)	0.7728 (2)	0.22129 (11)	0.0191 (3)
C14	0.52827 (19)	0.7303 (2)	0.07751 (12)	0.0232 (3)
H2	−0.042 (3)	0.707 (3)	0.1031 (18)	0.029 (6)*
H3	0.007 (3)	0.859 (4)	0.2370 (18)	0.033 (7)*
H4	0.170 (4)	1.072 (5)	0.256 (2)	0.055 (9)*
H5	0.311 (3)	1.139 (4)	0.140 (2)	0.045 (8)*
H6	0.272 (2)	0.982 (3)	0.0104 (15)	0.021 (5)*
H9	0.322 (2)	0.502 (3)	0.0692 (15)	0.021 (5)*
H10	0.163 (2)	0.438 (3)	0.1674 (14)	0.018 (5)*
H11	0.194 (3)	0.590 (3)	0.3008 (17)	0.031 (6)*
H12	0.367 (3)	0.796 (4)	0.3290 (19)	0.035 (7)*
H13	0.517 (3)	0.865 (3)	0.2292 (16)	0.028 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cr1	0.01696 (15)	0.01619 (16)	0.01472 (16)	0.00166 (8)	0.00287 (10)	−0.00070 (9)
F1	0.0228 (5)	0.0562 (9)	0.0388 (7)	0.0103 (5)	0.0129 (5)	0.0066 (6)
F2	0.0418 (7)	0.0336 (6)	0.0336 (6)	−0.0134 (5)	0.0168 (5)	−0.0007 (5)
F3	0.0353 (6)	0.0415 (7)	0.0170 (5)	−0.0013 (5)	0.0074 (5)	−0.0011 (5)
N1	0.0349 (9)	0.0456 (11)	0.0225 (8)	−0.0049 (8)	0.0005 (7)	−0.0021 (7)
C1	0.0204 (7)	0.0254 (8)	0.0175 (8)	0.0046 (6)	0.0019 (6)	0.0040 (6)
C2	0.0163 (7)	0.0321 (9)	0.0225 (9)	0.0064 (6)	0.0044 (6)	0.0064 (7)
C3	0.0274 (9)	0.0366 (10)	0.0256 (9)	0.0140 (8)	0.0093 (7)	0.0026 (8)
C4	0.0402 (11)	0.0263 (9)	0.0297 (10)	0.0141 (8)	0.0046 (8)	−0.0066 (8)
C5	0.0366 (10)	0.0153 (8)	0.0366 (10)	0.0046 (7)	0.0017 (8)	−0.0001 (7)
C6	0.0275 (8)	0.0208 (8)	0.0249 (9)	0.0030 (6)	0.0035 (7)	0.0071 (7)
C7	0.0219 (8)	0.0318 (9)	0.0181 (8)	0.0006 (7)	0.0001 (6)	0.0048 (7)
C8	0.0165 (7)	0.0207 (7)	0.0162 (7)	0.0014 (6)	0.0036 (5)	0.0011 (6)
C9	0.0186 (7)	0.0169 (7)	0.0185 (7)	0.0022 (5)	0.0024 (6)	−0.0010 (6)
C10	0.0184 (7)	0.0153 (7)	0.0261 (8)	0.0006 (5)	0.0042 (6)	0.0021 (6)
C11	0.0209 (7)	0.0245 (8)	0.0197 (8)	0.0008 (6)	0.0046 (6)	0.0044 (6)
C12	0.0233 (8)	0.0263 (8)	0.0143 (7)	−0.0005 (6)	0.0018 (6)	−0.0017 (6)
C13	0.0175 (7)	0.0231 (8)	0.0164 (7)	−0.0014 (6)	0.0009 (6)	−0.0005 (6)
C14	0.0212 (8)	0.0297 (9)	0.0197 (8)	−0.0016 (6)	0.0069 (6)	−0.0006 (7)

Geometric parameters (Å, º)

Cr1—C8	2.1118 (16)	N1—C7	1.144 (3)
Cr1—C1	2.1153 (17)	C1—C6	1.426 (3)
Cr1—C13	2.1384 (17)	C1—C2	1.429 (2)
Cr1—C2	2.1405 (18)	C1—C7	1.441 (3)
Cr1—C9	2.1443 (16)	C2—C3	1.411 (3)
Cr1—C4	2.1444 (19)	C3—C4	1.410 (3)
Cr1—C6	2.1467 (18)	C4—C5	1.421 (3)
Cr1—C10	2.1470 (17)	C5—C6	1.408 (3)
Cr1—C11	2.1479 (18)	C8—C9	1.421 (2)
Cr1—C3	2.1491 (18)	C8—C13	1.423 (2)
Cr1—C5	2.1566 (19)	C8—C14	1.488 (2)
Cr1—C12	2.1584 (18)	C9—C10	1.409 (2)
F1—C14	1.352 (2)	C10—C11	1.424 (3)
F2—C14	1.351 (2)	C11—C12	1.411 (3)
F3—C14	1.335 (2)	C12—C13	1.413 (2)
C8—Cr1—C1	113.28 (7)	C2—Cr1—C12	136.79 (7)
C8—Cr1—C13	39.12 (7)	C9—Cr1—C12	82.41 (7)
C1—Cr1—C13	145.62 (7)	C4—Cr1—C12	96.03 (8)
C8—Cr1—C2	144.74 (7)	C6—Cr1—C12	144.11 (7)
C1—Cr1—C2	39.23 (7)	C10—Cr1—C12	69.52 (7)
C13—Cr1—C2	175.09 (7)	C11—Cr1—C12	38.26 (7)
C8—Cr1—C9	39.00 (6)	C3—Cr1—C12	107.02 (7)
C1—Cr1—C9	98.52 (7)	C5—Cr1—C12	111.69 (8)
C13—Cr1—C9	70.44 (7)	C6—C1—C2	120.56 (17)
C2—Cr1—C9	111.51 (7)	C6—C1—C7	120.00 (16)
C8—Cr1—C4	139.93 (8)	C2—C1—C7	119.31 (17)
C1—Cr1—C4	83.07 (8)	C6—C1—Cr1	71.65 (10)
C13—Cr1—C4	108.03 (8)	C2—C1—Cr1	71.34 (10)
C2—Cr1—C4	69.96 (8)	C7—C1—Cr1	126.30 (13)
C9—Cr1—C4	178.37 (7)	C3—C2—C1	118.62 (18)
C8—Cr1—C6	99.52 (7)	C3—C2—Cr1	71.13 (11)
C1—Cr1—C6	39.08 (7)	C1—C2—Cr1	69.44 (10)
C13—Cr1—C6	113.15 (7)	C4—C3—C2	121.13 (18)
C2—Cr1—C6	70.66 (7)	C4—C3—Cr1	70.65 (11)
C9—Cr1—C6	111.37 (7)	C2—C3—Cr1	70.47 (10)
C4—Cr1—C6	69.65 (8)	C3—C4—C5	119.93 (19)
C8—Cr1—C10	70.10 (6)	C3—C4—Cr1	71.01 (11)
C1—Cr1—C10	108.80 (7)	C5—C4—Cr1	71.17 (11)
C13—Cr1—C10	83.04 (7)	C6—C5—C4	120.05 (19)
C2—Cr1—C10	95.82 (7)	C6—C5—Cr1	70.53 (10)
C9—Cr1—C10	38.32 (6)	C4—C5—Cr1	70.24 (11)
C4—Cr1—C10	141.46 (8)	C5—C6—C1	119.65 (17)
C6—Cr1—C10	140.85 (7)	C5—C6—Cr1	71.29 (11)
C8—Cr1—C11	83.06 (7)	C1—C6—Cr1	69.27 (10)
C1—Cr1—C11	138.44 (7)	N1—C7—C1	179.5 (2)
C13—Cr1—C11	69.79 (7)	C9—C8—C13	120.55 (15)
C2—Cr1—C11	106.38 (7)	C9—C8—C14	120.43 (15)
C9—Cr1—C11	69.74 (7)	C13—C8—C14	119.01 (15)
C4—Cr1—C11	109.31 (8)	C9—C8—Cr1	71.73 (9)
C6—Cr1—C11	177.02 (7)	C13—C8—Cr1	71.45 (9)
C10—Cr1—C11	38.72 (7)	C14—C8—Cr1	130.72 (12)
C8—Cr1—C3	176.73 (7)	C10—C9—C8	119.61 (15)
C1—Cr1—C3	69.87 (7)	C10—C9—Cr1	70.94 (9)
C13—Cr1—C3	137.67 (8)	C8—C9—Cr1	69.26 (9)
C2—Cr1—C3	38.41 (8)	C9—C10—C11	120.07 (15)
C9—Cr1—C3	142.63 (8)	C9—C10—Cr1	70.73 (9)
C4—Cr1—C3	38.34 (9)	C11—C10—Cr1	70.67 (10)
C6—Cr1—C3	82.41 (8)	C12—C11—C10	119.97 (16)
C10—Cr1—C3	110.05 (8)	C12—C11—Cr1	71.28 (10)
C11—Cr1—C3	95.08 (7)	C10—C11—Cr1	70.61 (10)
C8—Cr1—C5	110.53 (7)	C11—C12—C13	120.55 (16)
C1—Cr1—C5	69.96 (8)	C11—C12—Cr1	70.47 (10)
C13—Cr1—C5	98.12 (8)	C13—C12—Cr1	70.04 (10)
C2—Cr1—C5	83.06 (8)	C12—C13—C8	119.20 (15)
C9—Cr1—C5	141.68 (8)	C12—C13—Cr1	71.57 (10)
C4—Cr1—C5	38.59 (8)	C8—C13—Cr1	69.43 (9)
C6—Cr1—C5	38.18 (8)	F3—C14—F2	106.36 (15)
C10—Cr1—C5	178.74 (7)	F3—C14—F1	105.80 (15)
C11—Cr1—C5	142.18 (8)	F2—C14—F1	105.89 (15)
C3—Cr1—C5	69.39 (9)	F3—C14—C8	113.46 (15)
C8—Cr1—C12	69.88 (7)	F2—C14—C8	112.40 (15)
C1—Cr1—C12	175.95 (7)	F1—C14—C8	112.34 (15)
C13—Cr1—C12	38.38 (7)
C8—Cr1—C1—C6	−75.87 (12)	C4—Cr1—C8—C9	178.06 (12)
C13—Cr1—C1—C6	−45.96 (17)	C6—Cr1—C8—C9	−112.34 (10)
C2—Cr1—C1—C6	132.65 (16)	C10—Cr1—C8—C9	28.52 (10)
C9—Cr1—C1—C6	−113.59 (11)	C11—Cr1—C8—C9	66.17 (10)
C4—Cr1—C1—C6	66.04 (12)	C3—Cr1—C8—C9	121.7 (13)
C10—Cr1—C1—C6	−151.68 (10)	C5—Cr1—C8—C9	−150.31 (10)
C11—Cr1—C1—C6	177.45 (11)	C12—Cr1—C8—C9	103.24 (11)
C3—Cr1—C1—C6	103.19 (12)	C1—Cr1—C8—C13	153.50 (10)
C5—Cr1—C1—C6	28.58 (11)	C2—Cr1—C8—C13	−174.96 (12)
C12—Cr1—C1—C6	143.4 (10)	C9—Cr1—C8—C13	−132.47 (15)
C8—Cr1—C1—C2	151.48 (11)	C4—Cr1—C8—C13	45.58 (16)
C13—Cr1—C1—C2	−178.62 (12)	C6—Cr1—C8—C13	115.19 (11)
C9—Cr1—C1—C2	113.76 (11)	C10—Cr1—C8—C13	−103.95 (11)
C4—Cr1—C1—C2	−66.62 (12)	C11—Cr1—C8—C13	−66.31 (10)
C6—Cr1—C1—C2	−132.65 (16)	C3—Cr1—C8—C13	−10.8 (13)
C10—Cr1—C1—C2	75.67 (12)	C5—Cr1—C8—C13	77.21 (12)
C11—Cr1—C1—C2	44.80 (15)	C12—Cr1—C8—C13	−29.23 (10)
C3—Cr1—C1—C2	−29.46 (12)	C1—Cr1—C8—C14	40.78 (18)
C5—Cr1—C1—C2	−104.08 (12)	C13—Cr1—C8—C14	−112.7 (2)
C12—Cr1—C1—C2	10.8 (10)	C2—Cr1—C8—C14	72.3 (2)
C8—Cr1—C1—C7	38.34 (18)	C9—Cr1—C8—C14	114.8 (2)
C13—Cr1—C1—C7	68.2 (2)	C4—Cr1—C8—C14	−67.1 (2)
C2—Cr1—C1—C7	−113.1 (2)	C6—Cr1—C8—C14	2.47 (17)
C9—Cr1—C1—C7	0.61 (17)	C10—Cr1—C8—C14	143.33 (18)
C4—Cr1—C1—C7	−179.76 (17)	C11—Cr1—C8—C14	−179.03 (17)
C6—Cr1—C1—C7	114.2 (2)	C3—Cr1—C8—C14	−123.5 (13)
C10—Cr1—C1—C7	−37.48 (17)	C5—Cr1—C8—C14	−35.51 (18)
C11—Cr1—C1—C7	−68.35 (19)	C12—Cr1—C8—C14	−141.96 (18)
C3—Cr1—C1—C7	−142.61 (18)	C13—C8—C9—C10	2.4 (2)
C5—Cr1—C1—C7	142.78 (18)	C14—C8—C9—C10	−178.99 (16)
C12—Cr1—C1—C7	−102.4 (10)	Cr1—C8—C9—C10	−51.92 (14)
C6—C1—C2—C3	−0.9 (3)	C13—C8—C9—Cr1	54.29 (14)
C7—C1—C2—C3	175.05 (16)	C14—C8—C9—Cr1	−127.07 (16)
Cr1—C1—C2—C3	53.25 (15)	C8—Cr1—C9—C10	133.61 (15)
C6—C1—C2—Cr1	−54.17 (15)	C1—Cr1—C9—C10	−109.63 (11)
C7—C1—C2—Cr1	121.80 (16)	C13—Cr1—C9—C10	104.02 (11)
C8—Cr1—C2—C3	178.57 (12)	C2—Cr1—C9—C10	−71.16 (11)
C1—Cr1—C2—C3	−131.99 (17)	C4—Cr1—C9—C10	84 (3)
C13—Cr1—C2—C3	38.9 (9)	C6—Cr1—C9—C10	−147.98 (11)
C9—Cr1—C2—C3	151.38 (12)	C11—Cr1—C9—C10	29.06 (10)
C4—Cr1—C2—C3	−27.88 (12)	C3—Cr1—C9—C10	−41.80 (16)
C6—Cr1—C2—C3	−102.55 (13)	C5—Cr1—C9—C10	−177.97 (12)
C10—Cr1—C2—C3	115.23 (12)	C12—Cr1—C9—C10	66.38 (11)
C11—Cr1—C2—C3	77.17 (13)	C1—Cr1—C9—C8	116.75 (10)
C5—Cr1—C2—C3	−65.35 (13)	C13—Cr1—C9—C8	−29.59 (10)
C12—Cr1—C2—C3	49.12 (16)	C2—Cr1—C9—C8	155.22 (10)
C8—Cr1—C2—C1	−49.45 (17)	C4—Cr1—C9—C8	−50 (3)
C13—Cr1—C2—C1	170.8 (8)	C6—Cr1—C9—C8	78.41 (11)
C9—Cr1—C2—C1	−76.64 (12)	C10—Cr1—C9—C8	−133.61 (15)
C4—Cr1—C2—C1	104.10 (13)	C11—Cr1—C9—C8	−104.55 (11)
C6—Cr1—C2—C1	29.43 (11)	C3—Cr1—C9—C8	−175.42 (11)
C10—Cr1—C2—C1	−112.79 (11)	C5—Cr1—C9—C8	48.42 (16)
C11—Cr1—C2—C1	−150.84 (11)	C12—Cr1—C9—C8	−67.23 (10)
C3—Cr1—C2—C1	131.99 (17)	C8—C9—C10—C11	−1.4 (2)
C5—Cr1—C2—C1	66.64 (12)	Cr1—C9—C10—C11	−52.59 (14)
C12—Cr1—C2—C1	−178.89 (11)	C8—C9—C10—Cr1	51.15 (14)
C1—C2—C3—C4	−1.1 (3)	C8—Cr1—C10—C9	−28.99 (10)
Cr1—C2—C3—C4	51.32 (17)	C1—Cr1—C10—C9	79.72 (11)
C1—C2—C3—Cr1	−52.45 (14)	C13—Cr1—C10—C9	−67.07 (10)
C8—Cr1—C3—C4	59.8 (13)	C2—Cr1—C10—C9	117.74 (10)
C1—Cr1—C3—C4	−104.86 (13)	C4—Cr1—C10—C9	−177.40 (12)
C13—Cr1—C3—C4	49.67 (17)	C6—Cr1—C10—C9	51.45 (15)
C2—Cr1—C3—C4	−134.91 (18)	C11—Cr1—C10—C9	−133.24 (15)
C9—Cr1—C3—C4	177.86 (12)	C3—Cr1—C10—C9	154.49 (10)
C6—Cr1—C3—C4	−66.60 (13)	C5—Cr1—C10—C9	91 (4)
C10—Cr1—C3—C4	151.75 (12)	C12—Cr1—C10—C9	−104.19 (11)
C11—Cr1—C3—C4	115.01 (13)	C8—Cr1—C10—C11	104.25 (11)
C5—Cr1—C3—C4	−29.46 (12)	C1—Cr1—C10—C11	−147.04 (10)
C12—Cr1—C3—C4	77.87 (13)	C13—Cr1—C10—C11	66.17 (10)
C8—Cr1—C3—C2	−165.3 (13)	C2—Cr1—C10—C11	−109.02 (10)
C1—Cr1—C3—C2	30.04 (11)	C9—Cr1—C10—C11	133.24 (15)
C13—Cr1—C3—C2	−175.42 (11)	C4—Cr1—C10—C11	−44.16 (16)
C9—Cr1—C3—C2	−47.24 (17)	C6—Cr1—C10—C11	−175.31 (11)
C4—Cr1—C3—C2	134.91 (18)	C3—Cr1—C10—C11	−72.28 (11)
C6—Cr1—C3—C2	68.30 (12)	C5—Cr1—C10—C11	−136 (4)
C10—Cr1—C3—C2	−73.34 (12)	C12—Cr1—C10—C11	29.05 (10)
C11—Cr1—C3—C2	−110.09 (12)	C9—C10—C11—C12	−0.8 (3)
C5—Cr1—C3—C2	105.45 (13)	Cr1—C10—C11—C12	−53.43 (15)
C12—Cr1—C3—C2	−147.22 (11)	C9—C10—C11—Cr1	52.62 (14)
C2—C3—C4—C5	2.5 (3)	C8—Cr1—C11—C12	66.08 (11)
Cr1—C3—C4—C5	53.70 (16)	C1—Cr1—C11—C12	−176.34 (10)
C2—C3—C4—Cr1	−51.24 (16)	C13—Cr1—C11—C12	28.09 (10)
C8—Cr1—C4—C3	−175.61 (11)	C2—Cr1—C11—C12	−148.67 (11)
C1—Cr1—C4—C3	66.09 (12)	C9—Cr1—C11—C12	103.94 (11)
C13—Cr1—C4—C3	−147.33 (12)	C4—Cr1—C11—C12	−74.65 (12)
C2—Cr1—C4—C3	27.93 (12)	C6—Cr1—C11—C12	−143.7 (14)
C9—Cr1—C4—C3	−127 (3)	C10—Cr1—C11—C12	132.73 (15)
C6—Cr1—C4—C3	104.00 (13)	C3—Cr1—C11—C12	−111.21 (12)
C10—Cr1—C4—C3	−45.54 (18)	C5—Cr1—C11—C12	−48.70 (16)
C11—Cr1—C4—C3	−73.04 (13)	C8—Cr1—C11—C10	−66.64 (10)
C5—Cr1—C4—C3	132.44 (18)	C1—Cr1—C11—C10	50.93 (14)
C12—Cr1—C4—C3	−109.94 (12)	C13—Cr1—C11—C10	−104.64 (11)
C8—Cr1—C4—C5	51.94 (17)	C2—Cr1—C11—C10	78.60 (11)
C1—Cr1—C4—C5	−66.36 (13)	C9—Cr1—C11—C10	−28.79 (9)
C13—Cr1—C4—C5	80.23 (13)	C4—Cr1—C11—C10	152.62 (11)
C2—Cr1—C4—C5	−104.52 (13)	C6—Cr1—C11—C10	83.6 (14)
C9—Cr1—C4—C5	100 (3)	C3—Cr1—C11—C10	116.06 (11)
C6—Cr1—C4—C5	−28.45 (12)	C5—Cr1—C11—C10	178.57 (12)
C10—Cr1—C4—C5	−177.98 (12)	C12—Cr1—C11—C10	−132.73 (15)
C11—Cr1—C4—C5	154.52 (12)	C10—C11—C12—C13	2.2 (3)
C3—Cr1—C4—C5	−132.44 (18)	Cr1—C11—C12—C13	−50.96 (15)
C12—Cr1—C4—C5	117.62 (13)	C10—C11—C12—Cr1	53.12 (15)
C3—C4—C5—C6	−1.7 (3)	C8—Cr1—C12—C11	−104.88 (11)
Cr1—C4—C5—C6	51.90 (16)	C1—Cr1—C12—C11	36.8 (10)
C3—C4—C5—Cr1	−53.63 (16)	C13—Cr1—C12—C11	−134.63 (16)
C8—Cr1—C5—C6	79.03 (12)	C2—Cr1—C12—C11	46.78 (15)
C1—Cr1—C5—C6	−29.20 (11)	C9—Cr1—C12—C11	−66.71 (11)
C13—Cr1—C5—C6	117.45 (12)	C4—Cr1—C12—C11	113.77 (12)
C2—Cr1—C5—C6	−67.36 (12)	C6—Cr1—C12—C11	176.99 (12)
C9—Cr1—C5—C6	48.85 (17)	C10—Cr1—C12—C11	−29.37 (10)
C4—Cr1—C5—C6	−133.74 (18)	C3—Cr1—C12—C11	76.20 (12)
C10—Cr1—C5—C6	−40 (4)	C5—Cr1—C12—C11	150.27 (11)
C11—Cr1—C5—C6	−175.20 (11)	C8—Cr1—C12—C13	29.75 (10)
C3—Cr1—C5—C6	−104.46 (13)	C1—Cr1—C12—C13	171.5 (9)
C12—Cr1—C5—C6	154.76 (11)	C2—Cr1—C12—C13	−178.59 (11)
C8—Cr1—C5—C4	−147.23 (12)	C9—Cr1—C12—C13	67.92 (11)
C1—Cr1—C5—C4	104.54 (13)	C4—Cr1—C12—C13	−111.59 (12)
C13—Cr1—C5—C4	−108.81 (13)	C6—Cr1—C12—C13	−48.37 (17)
C2—Cr1—C5—C4	66.38 (13)	C10—Cr1—C12—C13	105.26 (11)
C9—Cr1—C5—C4	−177.41 (12)	C11—Cr1—C12—C13	134.63 (16)
C6—Cr1—C5—C4	133.74 (18)	C3—Cr1—C12—C13	−149.17 (11)
C10—Cr1—C5—C4	93 (4)	C5—Cr1—C12—C13	−75.09 (12)
C11—Cr1—C5—C4	−41.46 (18)	C11—C12—C13—C8	−1.2 (3)
C3—Cr1—C5—C4	29.28 (13)	Cr1—C12—C13—C8	−52.38 (14)
C12—Cr1—C5—C4	−71.50 (14)	C11—C12—C13—Cr1	51.14 (15)
C4—C5—C6—C1	−0.3 (3)	C9—C8—C13—C12	−1.0 (2)
Cr1—C5—C6—C1	51.48 (15)	C14—C8—C13—C12	−179.70 (16)
C4—C5—C6—Cr1	−51.77 (16)	Cr1—C8—C13—C12	53.38 (15)
C2—C1—C6—C5	1.6 (3)	C9—C8—C13—Cr1	−54.42 (14)
C7—C1—C6—C5	−174.32 (17)	C14—C8—C13—Cr1	126.92 (15)
Cr1—C1—C6—C5	−52.40 (15)	C8—Cr1—C13—C12	−132.39 (15)
C2—C1—C6—Cr1	54.02 (15)	C1—Cr1—C13—C12	−178.94 (12)
C7—C1—C6—Cr1	−121.91 (16)	C2—Cr1—C13—C12	11.3 (9)
C8—Cr1—C6—C5	−111.22 (12)	C9—Cr1—C13—C12	−102.88 (11)
C1—Cr1—C6—C5	133.37 (17)	C4—Cr1—C13—C12	76.52 (12)
C13—Cr1—C6—C5	−72.83 (13)	C6—Cr1—C13—C12	151.53 (11)
C2—Cr1—C6—C5	103.83 (13)	C10—Cr1—C13—C12	−65.57 (11)
C9—Cr1—C6—C5	−149.91 (12)	C11—Cr1—C13—C12	−28.00 (11)
C4—Cr1—C6—C5	28.73 (12)	C3—Cr1—C13—C12	46.70 (16)
C10—Cr1—C6—C5	178.71 (12)	C5—Cr1—C13—C12	114.91 (12)
C11—Cr1—C6—C5	98.8 (14)	C1—Cr1—C13—C8	−46.54 (17)
C3—Cr1—C6—C5	66.12 (13)	C2—Cr1—C13—C8	143.7 (8)
C12—Cr1—C6—C5	−42.52 (18)	C9—Cr1—C13—C8	29.51 (10)
C8—Cr1—C6—C1	115.42 (11)	C4—Cr1—C13—C8	−151.08 (11)
C13—Cr1—C6—C1	153.80 (10)	C6—Cr1—C13—C8	−76.07 (11)
C2—Cr1—C6—C1	−29.53 (11)	C10—Cr1—C13—C8	66.82 (10)
C9—Cr1—C6—C1	76.72 (11)	C11—Cr1—C13—C8	104.39 (11)
C4—Cr1—C6—C1	−104.64 (12)	C3—Cr1—C13—C8	179.09 (11)
C10—Cr1—C6—C1	45.34 (15)	C5—Cr1—C13—C8	−112.70 (11)
C11—Cr1—C6—C1	−34.6 (14)	C12—Cr1—C13—C8	132.39 (15)
C3—Cr1—C6—C1	−67.25 (12)	C9—C8—C14—F3	28.1 (2)
C5—Cr1—C6—C1	−133.37 (17)	C13—C8—C14—F3	−153.22 (16)
C12—Cr1—C6—C1	−175.88 (11)	Cr1—C8—C14—F3	−63.4 (2)
C6—C1—C7—N1	−2 (33)	C9—C8—C14—F2	148.85 (16)
C2—C1—C7—N1	−178 (100)	C13—C8—C14—F2	−32.5 (2)
Cr1—C1—C7—N1	−91 (33)	Cr1—C8—C14—F2	57.4 (2)
C1—Cr1—C8—C9	−74.03 (11)	C9—C8—C14—F1	−91.8 (2)
C13—Cr1—C8—C9	132.47 (15)	C13—C8—C14—F1	86.8 (2)
C2—Cr1—C8—C9	−42.49 (16)	Cr1—C8—C14—F1	176.68 (13)