Similarities and differences in the crystal packing of halogen-substituted indole derivatives

The role of different intermolecular interactions in the crystal structures of halogen-substituted indoles which are fused with six-membered or seven-membered cyclic rings is investigated here. Several crystal structures show isostructural characteristics due to the presence of similar supramolecular motifs. In the absence of any strong hydrogen bonds, the molecular packing of reported structures is primarily stabilized by the presence of non-classical N—H...π and C—H...π interactions in addition to C—H...X (X = F/Cl/Br) interactions. The nature and energetics of primary and secondary dimeric motifs are partitioned into the electrostatics, polarization, dispersion and exchange–repulsion components using the PIXEL method. Short and directional N—H...π interactions are further explored by a topological analysis of the electron density based on quantum theory of atoms in molecules.

Computing details

For all structures, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).

(HxP)

Crystal data

C12H13N	F(000) = 368
Mr = 171.23	Dx = 1.198 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4226 reflections
a = 6.1147 (4) Å	θ = 2.8–24.3°
b = 7.9668 (5) Å	µ = 0.07 mm^−1
c = 19.4856 (13) Å	T = 298 K
V = 949.23 (11) Å^3	Plate, colourless
Z = 4	0.43 × 0.31 × 0.15 mm

Data collection

Bruker APEX-II CCD diffractometer	2179 independent reflections
Radiation source: fine-focus sealed tube	1530 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.077
φ and ω scans	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan SADABS	h = −7→7
Tmin = 0.971, Tmax = 0.990	k = −10→10
23905 measured reflections	l = −25→25

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.142	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0639P)^2 + 0.1768P] where P = (Fo^2 + 2Fc^2)/3
2179 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.17 e Å^−3
3 restraints	Δρmin = −0.18 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
N1	1.2444 (3)	−0.0992 (3)	0.45684 (10)	0.0557 (5)
H1	1.3645	−0.1524	0.4494	0.067*
C1	1.1441 (4)	−0.0809 (3)	0.51964 (11)	0.0451 (5)
C2	1.2033 (4)	−0.1409 (3)	0.58395 (13)	0.0561 (6)
H2	1.3298	−0.2040	0.5900	0.067*
C3	1.0691 (5)	−0.1038 (3)	0.63809 (12)	0.0621 (7)
H3	1.1044	−0.1431	0.6816	0.074*
C4	0.8810 (5)	−0.0084 (3)	0.62901 (13)	0.0643 (7)
H4	0.7934	0.0154	0.6668	0.077*
C5	0.8215 (4)	0.0514 (3)	0.56573 (12)	0.0551 (6)
H5	0.6953	0.1153	0.5605	0.066*
C6	0.9546 (3)	0.0145 (3)	0.50914 (11)	0.0423 (5)
C7	0.9435 (3)	0.0538 (3)	0.43771 (11)	0.0427 (5)
C8	1.1207 (3)	−0.0180 (3)	0.40760 (11)	0.0473 (5)
C9	1.1717 (4)	−0.0162 (4)	0.33303 (12)	0.0648 (7)
H9A	1.2155	−0.1273	0.3181	0.078*
H9B	1.2911	0.0609	0.3239	0.078*
C10A	0.9700 (14)	0.0387 (12)	0.2948 (4)	0.0672 (10)	0.395 (6)
H10A	0.8687	−0.0548	0.2924	0.081*	0.395 (6)
H10B	1.0104	0.0685	0.2483	0.081*	0.395 (6)
C11A	0.8553 (14)	0.1876 (12)	0.3282 (4)	0.0672 (10)	0.395 (6)
H11A	0.9560	0.2815	0.3304	0.081*	0.395 (6)
H11B	0.7323	0.2209	0.2998	0.081*	0.395 (6)
C10B	1.0303 (8)	0.1081 (9)	0.2959 (3)	0.0672 (10)	0.605 (6)
H10C	1.0340	0.0836	0.2472	0.081*	0.605 (6)
H10D	1.0898	0.2198	0.3025	0.081*	0.605 (6)
C11B	0.7930 (8)	0.1059 (9)	0.3204 (2)	0.0672 (10)	0.605 (6)
H11C	0.7311	−0.0045	0.3124	0.081*	0.605 (6)
H11D	0.7089	0.1866	0.2941	0.081*	0.605 (6)
C12	0.7762 (4)	0.1491 (3)	0.39788 (13)	0.0573 (6)
H12A	0.6430	0.0834	0.3949	0.069*
H12B	0.7424	0.2529	0.4216	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0469 (11)	0.0635 (13)	0.0566 (12)	0.0174 (10)	0.0036 (9)	−0.0016 (9)
C1	0.0449 (12)	0.0393 (11)	0.0511 (13)	−0.0006 (10)	0.0006 (10)	−0.0047 (9)
C2	0.0580 (14)	0.0475 (13)	0.0628 (15)	0.0055 (11)	−0.0080 (13)	0.0014 (11)
C3	0.0774 (18)	0.0576 (14)	0.0513 (15)	−0.0029 (15)	−0.0048 (13)	0.0035 (12)
C4	0.0689 (15)	0.0710 (16)	0.0531 (14)	−0.0006 (15)	0.0124 (12)	−0.0053 (13)
C5	0.0542 (13)	0.0532 (14)	0.0578 (15)	0.0069 (12)	0.0072 (11)	−0.0042 (11)
C6	0.0428 (10)	0.0361 (10)	0.0479 (11)	−0.0023 (10)	−0.0004 (9)	−0.0045 (9)
C7	0.0406 (11)	0.0392 (12)	0.0483 (12)	−0.0040 (10)	−0.0003 (9)	−0.0039 (9)
C8	0.0452 (11)	0.0463 (12)	0.0504 (12)	−0.0008 (10)	0.0001 (10)	−0.0017 (10)
C9	0.0618 (15)	0.0778 (17)	0.0549 (14)	0.0001 (15)	0.0109 (12)	−0.0020 (13)
C10A	0.061 (2)	0.087 (3)	0.0532 (14)	−0.0094 (18)	−0.0073 (15)	0.010 (2)
C11A	0.061 (2)	0.087 (3)	0.0532 (14)	−0.0094 (18)	−0.0073 (15)	0.010 (2)
C10B	0.061 (2)	0.087 (3)	0.0532 (14)	−0.0094 (18)	−0.0073 (15)	0.010 (2)
C11B	0.061 (2)	0.087 (3)	0.0532 (14)	−0.0094 (18)	−0.0073 (15)	0.010 (2)
C12	0.0522 (13)	0.0555 (14)	0.0644 (15)	0.0076 (12)	−0.0045 (12)	0.0010 (12)

Geometric parameters (Å, º)

N1—C1	1.376 (3)	C9—C10A	1.505 (8)
N1—C8	1.383 (3)	C9—H9A	0.9700
N1—H1	0.8600	C9—H9B	0.9700
C1—C2	1.389 (3)	C10A—C11A	1.524 (11)
C1—C6	1.401 (3)	C10A—H10A	0.9700
C2—C3	1.369 (3)	C10A—H10B	0.9700
C2—H2	0.9300	C11A—C12	1.474 (8)
C3—C4	1.390 (4)	C11A—H11A	0.9700
C3—H3	0.9300	C11A—H11B	0.9700
C4—C5	1.371 (3)	C10B—C11B	1.527 (7)
C4—H4	0.9300	C10B—H10C	0.9700
C5—C6	1.402 (3)	C10B—H10D	0.9700
C5—H5	0.9300	C11B—C12	1.553 (5)
C6—C7	1.428 (3)	C11B—H11C	0.9700
C7—C8	1.358 (3)	C11B—H11D	0.9700
C7—C12	1.492 (3)	C12—H12A	0.9700
C8—C9	1.486 (3)	C12—H12B	0.9700
C9—C10B	1.500 (6)
C1—N1—C8	108.88 (18)	H9A—C9—H9B	108.4
C1—N1—H1	125.6	C9—C10A—C11A	113.1 (7)
C8—N1—H1	125.6	C9—C10A—H10A	109.0
N1—C1—C2	130.5 (2)	C11A—C10A—H10A	109.0
N1—C1—C6	107.23 (19)	C9—C10A—H10B	109.0
C2—C1—C6	122.3 (2)	C11A—C10A—H10B	109.0
C3—C2—C1	117.7 (2)	H10A—C10A—H10B	107.8
C3—C2—H2	121.1	C12—C11A—C10A	112.5 (7)
C1—C2—H2	121.1	C12—C11A—H11A	109.1
C2—C3—C4	121.1 (2)	C10A—C11A—H11A	109.1
C2—C3—H3	119.5	C12—C11A—H11B	109.1
C4—C3—H3	119.5	C10A—C11A—H11B	109.1
C5—C4—C3	121.6 (2)	H11A—C11A—H11B	107.8
C5—C4—H4	119.2	C9—C10B—C11B	112.9 (5)
C3—C4—H4	119.2	C9—C10B—H10C	109.0
C4—C5—C6	118.7 (2)	C11B—C10B—H10C	109.0
C4—C5—H5	120.6	C9—C10B—H10D	109.0
C6—C5—H5	120.6	C11B—C10B—H10D	109.0
C1—C6—C5	118.6 (2)	H10C—C10B—H10D	107.8
C1—C6—C7	107.47 (18)	C10B—C11B—C12	111.3 (5)
C5—C6—C7	133.9 (2)	C10B—C11B—H11C	109.4
C8—C7—C6	106.92 (18)	C12—C11B—H11C	109.4
C8—C7—C12	122.5 (2)	C10B—C11B—H11D	109.4
C6—C7—C12	130.61 (19)	C12—C11B—H11D	109.4
C7—C8—N1	109.50 (19)	H11C—C11B—H11D	108.0
C7—C8—C9	125.8 (2)	C11A—C12—C7	111.1 (4)
N1—C8—C9	124.6 (2)	C7—C12—C11B	110.4 (3)
C8—C9—C10B	110.9 (3)	C11A—C12—H12A	109.4
C8—C9—C10A	108.3 (4)	C7—C12—H12A	109.4
C8—C9—H9A	110.0	C11B—C12—H12A	83.0
C10B—C9—H9A	128.1	C11A—C12—H12B	109.4
C10A—C9—H9A	110.0	C7—C12—H12B	109.4
C8—C9—H9B	110.0	C11B—C12—H12B	131.9
C10B—C9—H9B	85.9	H12A—C12—H12B	108.0
C10A—C9—H9B	110.0
C8—N1—C1—C2	179.2 (2)	C1—N1—C8—C7	0.6 (3)
C8—N1—C1—C6	−0.3 (3)	C1—N1—C8—C9	−177.3 (2)
N1—C1—C2—C3	−179.4 (2)	C7—C8—C9—C10B	12.9 (4)
C6—C1—C2—C3	0.0 (3)	N1—C8—C9—C10B	−169.5 (3)
C1—C2—C3—C4	−0.5 (4)	C7—C8—C9—C10A	−14.2 (5)
C2—C3—C4—C5	0.4 (4)	N1—C8—C9—C10A	163.4 (4)
C3—C4—C5—C6	0.1 (4)	C8—C9—C10A—C11A	43.9 (9)
N1—C1—C6—C5	−180.0 (2)	C10B—C9—C10A—C11A	−56.4 (9)
C2—C1—C6—C5	0.5 (3)	C9—C10A—C11A—C12	−62.1 (11)
N1—C1—C6—C7	−0.1 (2)	C8—C9—C10B—C11B	−41.6 (7)
C2—C1—C6—C7	−179.7 (2)	C10A—C9—C10B—C11B	47.3 (9)
C4—C5—C6—C1	−0.6 (3)	C9—C10B—C11B—C12	60.2 (8)
C4—C5—C6—C7	179.6 (2)	C10A—C11A—C12—C7	43.2 (9)
C1—C6—C7—C8	0.5 (2)	C10A—C11A—C12—C11B	−51.0 (7)
C5—C6—C7—C8	−179.7 (2)	C8—C7—C12—C11A	−13.5 (5)
C1—C6—C7—C12	178.8 (2)	C6—C7—C12—C11A	168.4 (5)
C5—C6—C7—C12	−1.3 (4)	C8—C7—C12—C11B	17.9 (4)
C6—C7—C8—N1	−0.7 (2)	C6—C7—C12—C11B	−160.3 (3)
C12—C7—C8—N1	−179.2 (2)	C10B—C11B—C12—C11A	51.4 (7)
C6—C7—C8—C9	177.2 (2)	C10B—C11B—C12—C7	−45.7 (6)
C12—C7—C8—C9	−1.3 (3)

(HpBR2)

Crystal data

C13H14BrN	F(000) = 536
Mr = 264.16	Dx = 1.612 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7115 reflections
a = 8.7856 (8) Å	θ = 3.1–30.0°
b = 11.6453 (10) Å	µ = 3.74 mm^−1
c = 10.6401 (11) Å	T = 100 K
β = 90.470 (4)°	PLATE, light brown
V = 1088.56 (18) Å^3	0.45 × 0.22 × 0.15 mm
Z = 4

Data collection

Bruker APEX-II CCD diffractometer	1924 independent reflections
Radiation source: fine-focus sealed tube	1719 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.071
φ and ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan SADABS	h = −10→10
Tmin = 0.284, Tmax = 0.604	k = −12→13
8642 measured reflections	l = −12→11

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0598P)^2 + 0.2238P] where P = (Fo^2 + 2Fc^2)/3
1924 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 1.06 e Å^−3
0 restraints	Δρmin = −0.95 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br1	0.96279 (3)	0.32770 (3)	0.31675 (3)	0.01614 (17)
N1	0.6130 (3)	0.2581 (2)	0.3921 (2)	0.0120 (5)
H1	0.6501	0.3165	0.4350	0.014*
C1	0.6877 (3)	0.1986 (3)	0.3002 (3)	0.0130 (6)
C2	0.8329 (3)	0.2112 (3)	0.2522 (3)	0.0142 (6)
C3	0.8811 (3)	0.1398 (3)	0.1573 (3)	0.0158 (7)
H3	0.9802	0.1483	0.1235	0.019*
C4	0.7828 (3)	0.0541 (3)	0.1107 (3)	0.0155 (7)
H4	0.8168	0.0050	0.0453	0.019*
C5	0.6387 (3)	0.0399 (3)	0.1577 (3)	0.0153 (7)
H5	0.5741	−0.0188	0.1256	0.018*
C6	0.5883 (3)	0.1126 (3)	0.2532 (3)	0.0125 (6)
C7	0.4493 (3)	0.1228 (3)	0.3231 (3)	0.0126 (7)
C8	0.4679 (3)	0.2107 (3)	0.4062 (3)	0.0124 (6)
C9	0.3606 (3)	0.2556 (3)	0.5021 (3)	0.0136 (6)
H9A	0.2721	0.2908	0.4587	0.016*
H9B	0.4122	0.3164	0.5514	0.016*
C10	0.3037 (3)	0.1625 (2)	0.5920 (3)	0.0157 (7)
H10A	0.2520	0.2003	0.6632	0.019*
H10B	0.3927	0.1206	0.6264	0.019*
C11	0.1938 (3)	0.0753 (3)	0.5324 (3)	0.0163 (7)
H11A	0.1489	0.0289	0.6007	0.020*
H11B	0.1097	0.1183	0.4916	0.020*
C12	0.2604 (3)	−0.0065 (3)	0.4361 (3)	0.0152 (7)
H12A	0.1839	−0.0667	0.4174	0.018*
H12B	0.3500	−0.0448	0.4744	0.018*
C13	0.3095 (3)	0.0483 (3)	0.3112 (3)	0.0163 (7)
H13A	0.3297	−0.0135	0.2497	0.020*
H13B	0.2245	0.0954	0.2778	0.020*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0096 (2)	0.0197 (3)	0.0192 (3)	−0.00247 (10)	0.00127 (14)	0.00092 (11)
N1	0.0102 (11)	0.0106 (13)	0.0154 (13)	−0.0027 (10)	0.0020 (10)	−0.0002 (10)
C1	0.0125 (14)	0.0121 (15)	0.0142 (15)	0.0026 (12)	−0.0004 (12)	0.0047 (13)
C2	0.0107 (13)	0.0132 (15)	0.0185 (16)	−0.0012 (13)	−0.0027 (12)	0.0027 (13)
C3	0.0141 (14)	0.0172 (16)	0.0161 (16)	0.0021 (13)	0.0034 (12)	0.0063 (13)
C4	0.0187 (15)	0.0138 (16)	0.0138 (15)	0.0016 (13)	0.0027 (12)	0.0019 (12)
C5	0.0184 (14)	0.0120 (16)	0.0155 (16)	−0.0003 (13)	−0.0016 (12)	0.0023 (13)
C6	0.0127 (13)	0.0097 (15)	0.0151 (15)	0.0011 (12)	−0.0011 (12)	0.0042 (12)
C7	0.0102 (14)	0.0137 (17)	0.0137 (16)	−0.0024 (12)	0.0000 (12)	0.0030 (12)
C8	0.0086 (13)	0.0131 (15)	0.0155 (15)	0.0001 (12)	−0.0005 (12)	0.0053 (13)
C9	0.0114 (13)	0.0121 (15)	0.0174 (16)	0.0001 (12)	0.0000 (12)	−0.0016 (12)
C10	0.0143 (14)	0.0154 (16)	0.0174 (17)	−0.0018 (12)	0.0053 (13)	−0.0017 (12)
C11	0.0111 (13)	0.0174 (17)	0.0203 (16)	−0.0027 (13)	0.0034 (12)	0.0034 (13)
C12	0.0117 (13)	0.0124 (16)	0.0215 (16)	−0.0059 (12)	0.0005 (12)	0.0014 (13)
C13	0.0127 (13)	0.0167 (17)	0.0195 (16)	−0.0050 (13)	−0.0012 (12)	−0.0004 (13)

Geometric parameters (Å, º)

Br1—C2	1.898 (3)	C8—C9	1.489 (4)
N1—C1	1.370 (4)	C9—C10	1.532 (4)
N1—C8	1.398 (4)	C9—H9A	0.9900
N1—H1	0.8800	C9—H9B	0.9900
C1—C2	1.386 (4)	C10—C11	1.535 (4)
C1—C6	1.417 (4)	C10—H10A	0.9900
C2—C3	1.378 (5)	C10—H10B	0.9900
C3—C4	1.407 (4)	C11—C12	1.520 (4)
C3—H3	0.9500	C11—H11A	0.9900
C4—C5	1.376 (4)	C11—H11B	0.9900
C4—H4	0.9500	C12—C13	1.539 (4)
C5—C6	1.398 (4)	C12—H12A	0.9900
C5—H5	0.9500	C12—H12B	0.9900
C6—C7	1.440 (4)	C13—H13A	0.9900
C7—C8	1.361 (5)	C13—H13B	0.9900
C7—C13	1.508 (4)
C1—N1—C8	108.6 (2)	C10—C9—H9A	109.0
C1—N1—H1	125.7	C8—C9—H9B	109.0
C8—N1—H1	125.7	C10—C9—H9B	109.0
N1—C1—C2	131.0 (3)	H9A—C9—H9B	107.8
N1—C1—C6	108.2 (2)	C9—C10—C11	114.7 (3)
C2—C1—C6	120.8 (3)	C9—C10—H10A	108.6
C3—C2—C1	119.7 (3)	C11—C10—H10A	108.6
C3—C2—Br1	120.6 (2)	C9—C10—H10B	108.6
C1—C2—Br1	119.7 (2)	C11—C10—H10B	108.6
C2—C3—C4	119.7 (3)	H10A—C10—H10B	107.6
C2—C3—H3	120.2	C12—C11—C10	116.7 (2)
C4—C3—H3	120.2	C12—C11—H11A	108.1
C5—C4—C3	121.4 (3)	C10—C11—H11A	108.1
C5—C4—H4	119.3	C12—C11—H11B	108.1
C3—C4—H4	119.3	C10—C11—H11B	108.1
C4—C5—C6	119.3 (3)	H11A—C11—H11B	107.3
C4—C5—H5	120.3	C11—C12—C13	115.8 (2)
C6—C5—H5	120.3	C11—C12—H12A	108.3
C5—C6—C1	119.1 (3)	C13—C12—H12A	108.3
C5—C6—C7	134.5 (3)	C11—C12—H12B	108.3
C1—C6—C7	106.4 (3)	C13—C12—H12B	108.3
C8—C7—C6	107.4 (3)	H12A—C12—H12B	107.4
C8—C7—C13	125.5 (3)	C7—C13—C12	113.6 (2)
C6—C7—C13	127.1 (3)	C7—C13—H13A	108.9
C7—C8—N1	109.4 (2)	C12—C13—H13A	108.9
C7—C8—C9	129.5 (3)	C7—C13—H13B	108.9
N1—C8—C9	121.2 (3)	C12—C13—H13B	108.9
C8—C9—C10	113.0 (2)	H13A—C13—H13B	107.7
C8—C9—H9A	109.0
C8—N1—C1—C2	−179.5 (3)	C1—C6—C7—C8	0.2 (3)
C8—N1—C1—C6	0.9 (3)	C5—C6—C7—C13	1.2 (6)
N1—C1—C2—C3	−179.3 (3)	C1—C6—C7—C13	−178.0 (3)
C6—C1—C2—C3	0.2 (5)	C6—C7—C8—N1	0.3 (3)
N1—C1—C2—Br1	0.2 (5)	C13—C7—C8—N1	178.6 (3)
C6—C1—C2—Br1	179.7 (2)	C6—C7—C8—C9	−178.8 (3)
C1—C2—C3—C4	−0.4 (4)	C13—C7—C8—C9	−0.5 (5)
Br1—C2—C3—C4	−179.9 (2)	C1—N1—C8—C7	−0.8 (3)
C2—C3—C4—C5	0.1 (5)	C1—N1—C8—C9	178.4 (3)
C3—C4—C5—C6	0.5 (5)	C7—C8—C9—C10	54.5 (4)
C4—C5—C6—C1	−0.7 (4)	N1—C8—C9—C10	−124.5 (3)
C4—C5—C6—C7	−179.8 (3)	C8—C9—C10—C11	−70.5 (3)
N1—C1—C6—C5	180.0 (2)	C9—C10—C11—C12	68.7 (3)
C2—C1—C6—C5	0.3 (4)	C10—C11—C12—C13	−68.7 (4)
N1—C1—C6—C7	−0.7 (3)	C8—C7—C13—C12	−53.1 (4)
C2—C1—C6—C7	179.7 (3)	C6—C7—C13—C12	124.7 (3)
C5—C6—C7—C8	179.4 (3)	C11—C12—C13—C7	70.7 (3)

(HpBR3)

Crystal data

C13H14BrN	F(000) = 1072
Mr = 264.16	Dx = 1.594 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 7115 reflections
a = 23.769 (4) Å	θ = 3.1–30.0°
b = 11.2921 (19) Å	µ = 3.70 mm^−1
c = 8.2022 (11) Å	T = 100 K
V = 2201.5 (6) Å^3	PLATE, pale yellow
Z = 8	0.38 × 0.21 × 0.15 mm

Data collection

Bruker APEX-II CCD diffractometer	1938 independent reflections
Radiation source: fine-focus sealed tube	1763 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan SADABS	h = −25→28
Tmin = 0.334, Tmax = 0.607	k = −10→13
8659 measured reflections	l = −9→8

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.37	w = 1/[σ^2(Fo^2) + (0.P)^2 + 7.6838P] where P = (Fo^2 + 2Fc^2)/3
1938 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.53 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br1	0.078995 (18)	0.10973 (4)	0.60491 (5)	0.02489 (16)
N1	0.29182 (15)	0.2542 (3)	0.6847 (4)	0.0200 (8)
H1	0.2877	0.3164	0.7481	0.024*
C1	0.24890 (19)	0.1875 (4)	0.6234 (5)	0.0192 (9)
C2	0.19062 (18)	0.1969 (4)	0.6469 (5)	0.0193 (9)
H2	0.1743	0.2588	0.7095	0.023*
C3	0.15861 (17)	0.1103 (4)	0.5730 (5)	0.0171 (9)
C4	0.18146 (19)	0.0193 (4)	0.4786 (5)	0.0204 (9)
H4	0.1574	−0.0377	0.4299	0.025*
C5	0.23865 (18)	0.0119 (4)	0.4558 (5)	0.0212 (9)
H5	0.2542	−0.0499	0.3915	0.025*
C6	0.27343 (19)	0.0958 (4)	0.5280 (5)	0.0195 (9)
C7	0.33344 (17)	0.1120 (4)	0.5358 (5)	0.0186 (9)
C8	0.34311 (18)	0.2091 (4)	0.6319 (5)	0.0202 (9)
C9	0.39629 (19)	0.2637 (4)	0.6888 (6)	0.0248 (10)
H9A	0.4102	0.2176	0.7832	0.030*
H9B	0.3878	0.3446	0.7284	0.030*
C10	0.44332 (19)	0.2723 (4)	0.5644 (5)	0.0235 (10)
H10A	0.4749	0.3168	0.6138	0.028*
H10B	0.4296	0.3189	0.4703	0.028*
C12	0.42744 (19)	0.0898 (4)	0.3826 (5)	0.0242 (10)
H12A	0.4500	0.0287	0.3259	0.029*
H12B	0.4145	0.1470	0.2992	0.029*
C13	0.37570 (19)	0.0298 (4)	0.4566 (6)	0.0239 (10)
H13A	0.3563	−0.0152	0.3695	0.029*
H13B	0.3886	−0.0281	0.5393	0.029*
C11	0.46577 (18)	0.1550 (4)	0.5016 (6)	0.0244 (10)
H11A	0.4730	0.1026	0.5962	0.029*
H11B	0.5023	0.1695	0.4473	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0200 (3)	0.0292 (3)	0.0255 (3)	0.00098 (19)	0.00006 (19)	−0.00126 (19)
N1	0.026 (2)	0.0181 (18)	0.0158 (18)	0.0006 (15)	0.0020 (16)	−0.0050 (15)
C1	0.028 (2)	0.0170 (19)	0.0120 (19)	−0.0048 (18)	−0.0048 (17)	0.0057 (16)
C2	0.027 (2)	0.019 (2)	0.013 (2)	0.0030 (18)	−0.0004 (17)	0.0014 (16)
C3	0.018 (2)	0.022 (2)	0.011 (2)	0.0013 (18)	−0.0006 (16)	0.0044 (17)
C4	0.028 (2)	0.020 (2)	0.013 (2)	0.0013 (19)	−0.0029 (18)	0.0037 (17)
C5	0.028 (2)	0.019 (2)	0.016 (2)	0.0025 (19)	−0.0002 (18)	−0.0005 (17)
C6	0.030 (2)	0.019 (2)	0.0101 (19)	0.0051 (18)	−0.0001 (18)	0.0041 (17)
C7	0.018 (2)	0.024 (2)	0.014 (2)	0.0004 (18)	−0.0013 (17)	0.0061 (18)
C8	0.026 (2)	0.022 (2)	0.012 (2)	0.0041 (18)	0.0028 (17)	0.0051 (17)
C9	0.030 (3)	0.024 (2)	0.021 (2)	0.001 (2)	0.000 (2)	−0.0008 (19)
C10	0.027 (2)	0.026 (2)	0.018 (2)	−0.0017 (19)	−0.0011 (18)	−0.0004 (18)
C12	0.029 (2)	0.023 (2)	0.021 (2)	0.0093 (19)	0.006 (2)	−0.0044 (18)
C13	0.031 (3)	0.020 (2)	0.020 (2)	0.0003 (19)	−0.0031 (19)	−0.0016 (18)
C11	0.020 (2)	0.030 (2)	0.023 (2)	0.0045 (19)	0.0023 (19)	0.0007 (19)

Geometric parameters (Å, º)

Br1—C3	1.910 (4)	C8—C9	1.482 (6)
N1—C1	1.364 (5)	C9—C10	1.517 (6)
N1—C8	1.390 (5)	C9—H9A	0.9900
N1—H1	0.8800	C9—H9B	0.9900
C1—C2	1.402 (6)	C10—C11	1.518 (6)
C1—C6	1.423 (6)	C10—H10A	0.9900
C2—C3	1.379 (6)	C10—H10B	0.9900
C2—H2	0.9500	C12—C11	1.525 (6)
C3—C4	1.397 (6)	C12—C13	1.530 (6)
C4—C5	1.375 (6)	C12—H12A	0.9900
C4—H4	0.9500	C12—H12B	0.9900
C5—C6	1.390 (6)	C13—H13A	0.9900
C5—H5	0.9500	C13—H13B	0.9900
C6—C7	1.439 (6)	C11—H11A	0.9900
C7—C8	1.369 (6)	C11—H11B	0.9900
C7—C13	1.515 (6)
C1—N1—C8	109.8 (3)	C10—C9—H9A	108.2
C1—N1—H1	125.1	C8—C9—H9B	108.2
C8—N1—H1	125.1	C10—C9—H9B	108.2
N1—C1—C2	130.3 (4)	H9A—C9—H9B	107.4
N1—C1—C6	107.3 (4)	C9—C10—C11	115.6 (4)
C2—C1—C6	122.4 (4)	C9—C10—H10A	108.4
C3—C2—C1	115.5 (4)	C11—C10—H10A	108.4
C3—C2—H2	122.2	C9—C10—H10B	108.4
C1—C2—H2	122.2	C11—C10—H10B	108.4
C2—C3—C4	123.4 (4)	H10A—C10—H10B	107.4
C2—C3—Br1	119.3 (3)	C11—C12—C13	116.1 (4)
C4—C3—Br1	117.3 (3)	C11—C12—H12A	108.3
C5—C4—C3	120.3 (4)	C13—C12—H12A	108.3
C5—C4—H4	119.8	C11—C12—H12B	108.3
C3—C4—H4	119.8	C13—C12—H12B	108.3
C4—C5—C6	119.2 (4)	H12A—C12—H12B	107.4
C4—C5—H5	120.4	C7—C13—C12	115.6 (4)
C6—C5—H5	120.4	C7—C13—H13A	108.4
C5—C6—C1	119.1 (4)	C12—C13—H13A	108.4
C5—C6—C7	134.0 (4)	C7—C13—H13B	108.4
C1—C6—C7	106.8 (4)	C12—C13—H13B	108.4
C8—C7—C6	107.1 (4)	H13A—C13—H13B	107.5
C8—C7—C13	128.8 (4)	C10—C11—C12	115.4 (4)
C6—C7—C13	124.0 (4)	C10—C11—H11A	108.4
C7—C8—N1	109.0 (4)	C12—C11—H11A	108.4
C7—C8—C9	131.1 (4)	C10—C11—H11B	108.4
N1—C8—C9	119.8 (4)	C12—C11—H11B	108.4
C8—C9—C10	116.3 (4)	H11A—C11—H11B	107.5
C8—C9—H9A	108.2
C8—N1—C1—C2	178.0 (4)	C5—C6—C7—C13	−0.1 (7)
C8—N1—C1—C6	0.2 (4)	C1—C6—C7—C13	177.2 (4)
N1—C1—C2—C3	−176.7 (4)	C6—C7—C8—N1	0.1 (5)
C6—C1—C2—C3	0.8 (6)	C13—C7—C8—N1	−176.9 (4)
C1—C2—C3—C4	−0.9 (6)	C6—C7—C8—C9	176.8 (4)
C1—C2—C3—Br1	177.1 (3)	C13—C7—C8—C9	−0.2 (8)
C2—C3—C4—C5	0.4 (6)	C1—N1—C8—C7	−0.1 (5)
Br1—C3—C4—C5	−177.6 (3)	C1—N1—C8—C9	−177.3 (4)
C3—C4—C5—C6	0.1 (6)	C7—C8—C9—C10	41.7 (7)
C4—C5—C6—C1	−0.1 (6)	N1—C8—C9—C10	−141.9 (4)
C4—C5—C6—C7	176.9 (4)	C8—C9—C10—C11	−63.4 (5)
N1—C1—C6—C5	177.6 (4)	C8—C7—C13—C12	−40.9 (6)
C2—C1—C6—C5	−0.4 (6)	C6—C7—C13—C12	142.6 (4)
N1—C1—C6—C7	−0.1 (4)	C11—C12—C13—C7	63.2 (5)
C2—C1—C6—C7	−178.1 (4)	C9—C10—C11—C12	74.0 (5)
C5—C6—C7—C8	−177.2 (4)	C13—C12—C11—C10	−74.3 (5)
C1—C6—C7—C8	0.0 (5)

(HpBR4)

Crystal data

C13H14BrN	F(000) = 536
Mr = 264.16	Dx = 1.587 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9362 reflections
a = 9.5400 (4) Å	θ = 3.3–30.5°
b = 6.2063 (2) Å	µ = 3.68 mm^−1
c = 18.8852 (8) Å	T = 100 K
β = 98.474 (1)°	Plate, pale yellow
V = 1105.95 (7) Å^3	0.33 × 0.22 × 0.15 mm
Z = 4

Data collection

Bruker APEX-II CCD diffractometer	3369 independent reflections
Radiation source: fine-focus sealed tube	2972 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 30.5°, θmin = 2.8°
Absorption correction: multi-scan SADABS	h = −13→13
Tmin = 0.376, Tmax = 0.608	k = −8→6
15446 measured reflections	l = −26→26

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.060	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0237P)^2 + 0.5348P] where P = (Fo^2 + 2Fc^2)/3
3369 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.55 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br1	0.933405 (13)	0.07054 (2)	0.336342 (8)	0.02152 (6)
N1	0.44045 (11)	0.67576 (19)	0.32380 (6)	0.0136 (2)
H1	0.4221	0.8057	0.3062	0.016*
C1	0.56209 (13)	0.5603 (2)	0.31979 (7)	0.0124 (2)
C2	0.68272 (14)	0.6149 (2)	0.28983 (7)	0.0151 (2)
H2	0.6890	0.7488	0.2661	0.018*
C3	0.79327 (14)	0.4671 (2)	0.29592 (7)	0.0162 (3)
H3	0.8776	0.4998	0.2769	0.019*
C4	0.77990 (13)	0.2700 (2)	0.33017 (7)	0.0150 (2)
C5	0.66103 (13)	0.2119 (2)	0.35975 (7)	0.0134 (2)
H5	0.6551	0.0759	0.3822	0.016*
C6	0.54952 (13)	0.3613 (2)	0.35529 (7)	0.0120 (2)
C7	0.41505 (13)	0.3629 (2)	0.38064 (7)	0.0121 (2)
C8	0.35152 (13)	0.5550 (2)	0.35994 (7)	0.0123 (2)
C9	0.21168 (13)	0.6392 (2)	0.37459 (7)	0.0151 (2)
H9A	0.1351	0.5463	0.3501	0.018*
H9B	0.1973	0.7862	0.3545	0.018*
C10	0.20123 (15)	0.6463 (2)	0.45492 (8)	0.0176 (3)
H10A	0.2869	0.7184	0.4801	0.021*
H10B	0.1183	0.7353	0.4620	0.021*
C11	0.18697 (14)	0.4254 (2)	0.48931 (8)	0.0165 (3)
H11A	0.1638	0.4488	0.5381	0.020*
H11B	0.1053	0.3502	0.4615	0.020*
C12	0.31531 (14)	0.2752 (2)	0.49504 (7)	0.0174 (3)
H12A	0.2969	0.1491	0.5244	0.021*
H12B	0.3984	0.3520	0.5209	0.021*
C13	0.35376 (14)	0.1931 (2)	0.42370 (7)	0.0151 (2)
H13A	0.4231	0.0743	0.4336	0.018*
H13B	0.2675	0.1335	0.3948	0.018*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.01277 (7)	0.02402 (9)	0.02763 (9)	0.00420 (5)	0.00248 (5)	−0.00545 (6)
N1	0.0153 (5)	0.0125 (5)	0.0132 (5)	0.0017 (4)	0.0026 (4)	0.0038 (4)
C1	0.0140 (5)	0.0140 (6)	0.0091 (5)	−0.0009 (4)	0.0013 (4)	0.0003 (4)
C2	0.0168 (6)	0.0176 (6)	0.0106 (6)	−0.0036 (5)	0.0016 (5)	0.0006 (5)
C3	0.0143 (5)	0.0225 (7)	0.0123 (6)	−0.0039 (5)	0.0035 (5)	−0.0030 (5)
C4	0.0115 (5)	0.0194 (7)	0.0137 (6)	0.0014 (5)	0.0005 (4)	−0.0041 (5)
C5	0.0144 (5)	0.0139 (6)	0.0115 (6)	0.0003 (5)	0.0010 (4)	−0.0008 (5)
C6	0.0128 (5)	0.0137 (6)	0.0092 (5)	−0.0008 (4)	0.0009 (4)	−0.0004 (5)
C7	0.0128 (5)	0.0120 (6)	0.0117 (6)	−0.0009 (4)	0.0025 (4)	−0.0008 (5)
C8	0.0134 (5)	0.0135 (6)	0.0100 (6)	−0.0012 (4)	0.0019 (4)	−0.0008 (4)
C9	0.0137 (5)	0.0161 (6)	0.0157 (6)	0.0029 (5)	0.0023 (5)	−0.0002 (5)
C10	0.0191 (6)	0.0168 (6)	0.0182 (7)	0.0014 (5)	0.0067 (5)	−0.0027 (5)
C11	0.0170 (6)	0.0186 (7)	0.0154 (6)	−0.0013 (5)	0.0078 (5)	−0.0018 (5)
C12	0.0201 (6)	0.0184 (7)	0.0146 (6)	−0.0011 (5)	0.0058 (5)	0.0030 (5)
C13	0.0168 (6)	0.0116 (6)	0.0178 (6)	−0.0012 (5)	0.0057 (5)	0.0005 (5)

Geometric parameters (Å, º)

Br1—C4	1.9081 (13)	C8—C9	1.4960 (17)
N1—C1	1.3754 (16)	C9—C10	1.5355 (19)
N1—C8	1.3847 (16)	C9—H9A	0.9900
N1—H1	0.8800	C9—H9B	0.9900
C1—C2	1.3968 (17)	C10—C11	1.532 (2)
C1—C6	1.4186 (18)	C10—H10A	0.9900
C2—C3	1.390 (2)	C10—H10B	0.9900
C2—H2	0.9500	C11—C12	1.5301 (19)
C3—C4	1.398 (2)	C11—H11A	0.9900
C3—H3	0.9500	C11—H11B	0.9900
C4—C5	1.3839 (17)	C12—C13	1.5343 (19)
C5—C6	1.4045 (18)	C12—H12A	0.9900
C5—H5	0.9500	C12—H12B	0.9900
C6—C7	1.4339 (17)	C13—H13A	0.9900
C7—C8	1.3683 (18)	C13—H13B	0.9900
C7—C13	1.5011 (18)
C1—N1—C8	109.18 (11)	C10—C9—H9A	109.1
C1—N1—H1	125.4	C8—C9—H9B	109.1
C8—N1—H1	125.4	C10—C9—H9B	109.1
N1—C1—C2	130.40 (12)	H9A—C9—H9B	107.8
N1—C1—C6	107.25 (11)	C11—C10—C9	114.57 (12)
C2—C1—C6	122.33 (12)	C11—C10—H10A	108.6
C3—C2—C1	117.81 (13)	C9—C10—H10A	108.6
C3—C2—H2	121.1	C11—C10—H10B	108.6
C1—C2—H2	121.1	C9—C10—H10B	108.6
C2—C3—C4	119.74 (12)	H10A—C10—H10B	107.6
C2—C3—H3	120.1	C12—C11—C10	117.09 (11)
C4—C3—H3	120.1	C12—C11—H11A	108.0
C5—C4—C3	123.43 (12)	C10—C11—H11A	108.0
C5—C4—Br1	118.25 (10)	C12—C11—H11B	108.0
C3—C4—Br1	118.32 (9)	C10—C11—H11B	108.0
C4—C5—C6	117.52 (12)	H11A—C11—H11B	107.3
C4—C5—H5	121.2	C11—C12—C13	115.62 (12)
C6—C5—H5	121.2	C11—C12—H12A	108.4
C5—C6—C1	119.15 (11)	C13—C12—H12A	108.4
C5—C6—C7	133.74 (12)	C11—C12—H12B	108.4
C1—C6—C7	107.10 (11)	C13—C12—H12B	108.4
C8—C7—C6	106.91 (11)	H12A—C12—H12B	107.4
C8—C7—C13	125.10 (11)	C7—C13—C12	113.92 (11)
C6—C7—C13	127.97 (12)	C7—C13—H13A	108.8
C7—C8—N1	109.55 (11)	C12—C13—H13A	108.8
C7—C8—C9	128.39 (12)	C7—C13—H13B	108.8
N1—C8—C9	122.01 (12)	C12—C13—H13B	108.8
C8—C9—C10	112.47 (11)	H13A—C13—H13B	107.7
C8—C9—H9A	109.1
C8—N1—C1—C2	−178.84 (14)	C5—C6—C7—C13	1.6 (2)
C8—N1—C1—C6	−0.62 (14)	C1—C6—C7—C13	−177.68 (13)
N1—C1—C2—C3	177.72 (13)	C6—C7—C8—N1	−0.94 (15)
C6—C1—C2—C3	−0.3 (2)	C13—C7—C8—N1	177.36 (12)
C1—C2—C3—C4	1.0 (2)	C6—C7—C8—C9	−178.24 (13)
C2—C3—C4—C5	−0.6 (2)	C13—C7—C8—C9	0.1 (2)
C2—C3—C4—Br1	179.29 (10)	C1—N1—C8—C7	0.99 (15)
C3—C4—C5—C6	−0.6 (2)	C1—N1—C8—C9	178.50 (12)
Br1—C4—C5—C6	179.46 (9)	C7—C8—C9—C10	56.10 (19)
C4—C5—C6—C1	1.40 (19)	N1—C8—C9—C10	−120.90 (14)
C4—C5—C6—C7	−177.84 (14)	C8—C9—C10—C11	−72.29 (15)
N1—C1—C6—C5	−179.37 (11)	C9—C10—C11—C12	67.89 (16)
C2—C1—C6—C5	−1.0 (2)	C10—C11—C12—C13	−66.52 (17)
N1—C1—C6—C7	0.05 (14)	C8—C7—C13—C12	−55.42 (18)
C2—C1—C6—C7	178.44 (12)	C6—C7—C13—C12	122.51 (14)
C5—C6—C7—C8	179.84 (14)	C11—C12—C13—C7	70.89 (15)
C1—C6—C7—C8	0.54 (15)

(HpCL2)

Crystal data

C13H14ClN	F(000) = 464
Mr = 219.70	Dx = 1.382 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1783 reflections
a = 8.6883 (15) Å	θ = 2.6–26.1°
b = 11.7901 (19) Å	µ = 0.32 mm^−1
c = 10.3129 (17) Å	T = 100 K
β = 90.892 (5)°	Plate, colourless
V = 1056.3 (3) Å^3	0.44 × 0.32 × 0.18 mm
Z = 4

Data collection

Bruker APEX-II CCD diffractometer	2155 independent reflections
Radiation source: fine-focus sealed tube	1427 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.092
φ and ω scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan SADABS	h = −10→10
Tmin = 0.871, Tmax = 0.944	k = −14→13
9349 measured reflections	l = −12→12

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: inferred from neighbouring sites
wR(F^2) = 0.145	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0575P)^2 + 1.3525P] where P = (Fo^2 + 2Fc^2)/3
2155 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.77 e Å^−3
0 restraints	Δρmin = −0.42 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl1	1.45427 (10)	0.31846 (8)	0.81290 (8)	0.0242 (3)
N1	1.1109 (3)	0.2571 (2)	0.8904 (2)	0.0162 (6)
H1	1.1467	0.3155	0.9347	0.019*
C1	1.1893 (4)	0.1981 (3)	0.7976 (3)	0.0163 (7)
C2	1.3378 (4)	0.2122 (3)	0.7503 (3)	0.0195 (8)
C3	1.3883 (4)	0.1410 (3)	0.6544 (3)	0.0225 (8)
H3	1.4889	0.1503	0.6211	0.027*
C4	1.2930 (4)	0.0550 (3)	0.6053 (3)	0.0205 (8)
H4	1.3294	0.0064	0.5390	0.025*
C5	1.1461 (4)	0.0399 (3)	0.6524 (3)	0.0189 (8)
H5	1.0824	−0.0193	0.6193	0.023*
C6	1.0917 (4)	0.1122 (3)	0.7493 (3)	0.0161 (7)
C7	0.9490 (4)	0.1214 (3)	0.8181 (3)	0.0148 (7)
C8	0.9659 (4)	0.2096 (3)	0.9026 (3)	0.0154 (7)
C9	0.8538 (4)	0.2538 (3)	1.0000 (3)	0.0167 (7)
H9A	0.7646	0.2876	0.9533	0.020*
H9B	0.9040	0.3146	1.0516	0.020*
C10	0.7962 (4)	0.1619 (3)	1.0917 (3)	0.0177 (7)
H10A	0.8865	0.1212	1.1285	0.021*
H10B	0.7430	0.1991	1.1645	0.021*
C11	0.6874 (4)	0.0755 (3)	1.0305 (3)	0.0196 (8)
H11A	0.6029	0.1171	0.9859	0.023*
H11B	0.6410	0.0305	1.1009	0.023*
C12	0.7581 (4)	−0.0070 (3)	0.9332 (3)	0.0183 (7)
H12A	0.6816	−0.0669	0.9129	0.022*
H12B	0.8481	−0.0442	0.9752	0.022*
C13	0.8102 (4)	0.0461 (3)	0.8052 (3)	0.0195 (8)
H13A	0.8333	−0.0155	0.7433	0.023*
H13B	0.7239	0.0910	0.7679	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0213 (5)	0.0279 (5)	0.0235 (4)	−0.0038 (4)	0.0008 (3)	0.0009 (4)
N1	0.0178 (15)	0.0124 (15)	0.0185 (14)	−0.0021 (12)	−0.0013 (11)	0.0007 (12)
C1	0.0180 (17)	0.0174 (19)	0.0134 (15)	−0.0001 (14)	−0.0021 (13)	0.0045 (14)
C2	0.0188 (18)	0.021 (2)	0.0181 (16)	−0.0016 (15)	−0.0050 (14)	0.0067 (15)
C3	0.0202 (19)	0.028 (2)	0.0191 (17)	0.0041 (16)	0.0039 (14)	0.0075 (16)
C4	0.025 (2)	0.020 (2)	0.0168 (16)	0.0066 (15)	0.0026 (14)	0.0036 (15)
C5	0.026 (2)	0.0168 (19)	0.0135 (15)	0.0026 (15)	−0.0029 (14)	0.0030 (14)
C6	0.0175 (17)	0.0161 (18)	0.0145 (15)	−0.0004 (14)	−0.0048 (13)	0.0067 (14)
C7	0.0157 (17)	0.0166 (18)	0.0121 (14)	−0.0007 (14)	−0.0019 (12)	0.0039 (14)
C8	0.0151 (17)	0.0161 (18)	0.0150 (15)	−0.0006 (13)	−0.0012 (13)	0.0065 (14)
C9	0.0178 (18)	0.0132 (18)	0.0191 (16)	−0.0003 (14)	−0.0016 (13)	−0.0026 (14)
C10	0.0185 (18)	0.0161 (19)	0.0186 (16)	−0.0004 (14)	0.0037 (13)	−0.0010 (14)
C11	0.0173 (18)	0.020 (2)	0.0218 (17)	−0.0008 (15)	0.0046 (14)	0.0023 (15)
C12	0.0189 (19)	0.0146 (18)	0.0213 (16)	−0.0044 (14)	−0.0018 (14)	0.0018 (14)
C13	0.0203 (19)	0.021 (2)	0.0175 (16)	−0.0024 (15)	−0.0034 (14)	−0.0016 (15)

Geometric parameters (Å, º)

Cl1—C2	1.729 (4)	C8—C9	1.503 (4)
N1—C1	1.373 (4)	C9—C10	1.528 (4)
N1—C8	1.387 (4)	C9—H9A	0.9900
N1—H1	0.8800	C9—H9B	0.9900
C1—C2	1.397 (5)	C10—C11	1.521 (5)
C1—C6	1.407 (5)	C10—H10A	0.9900
C2—C3	1.374 (5)	C10—H10B	0.9900
C3—C4	1.400 (5)	C11—C12	1.533 (4)
C3—H3	0.9500	C11—H11A	0.9900
C4—C5	1.384 (5)	C11—H11B	0.9900
C4—H4	0.9500	C12—C13	1.536 (4)
C5—C6	1.401 (4)	C12—H12A	0.9900
C5—H5	0.9500	C12—H12B	0.9900
C6—C7	1.442 (4)	C13—H13A	0.9900
C7—C8	1.364 (5)	C13—H13B	0.9900
C7—C13	1.502 (4)
C1—N1—C8	108.6 (3)	C10—C9—H9A	109.0
C1—N1—H1	125.7	C8—C9—H9B	109.0
C8—N1—H1	125.7	C10—C9—H9B	109.0
N1—C1—C2	130.9 (3)	H9A—C9—H9B	107.8
N1—C1—C6	108.0 (3)	C11—C10—C9	115.2 (3)
C2—C1—C6	121.1 (3)	C11—C10—H10A	108.5
C3—C2—C1	119.1 (3)	C9—C10—H10A	108.5
C3—C2—Cl1	121.3 (3)	C11—C10—H10B	108.5
C1—C2—Cl1	119.6 (3)	C9—C10—H10B	108.5
C2—C3—C4	120.6 (3)	H10A—C10—H10B	107.5
C2—C3—H3	119.7	C10—C11—C12	116.4 (3)
C4—C3—H3	119.7	C10—C11—H11A	108.2
C5—C4—C3	120.7 (3)	C12—C11—H11A	108.2
C5—C4—H4	119.7	C10—C11—H11B	108.2
C3—C4—H4	119.7	C12—C11—H11B	108.2
C4—C5—C6	119.6 (3)	H11A—C11—H11B	107.3
C4—C5—H5	120.2	C11—C12—C13	115.5 (3)
C6—C5—H5	120.2	C11—C12—H12A	108.4
C5—C6—C1	118.9 (3)	C13—C12—H12A	108.4
C5—C6—C7	134.3 (3)	C11—C12—H12B	108.4
C1—C6—C7	106.8 (3)	C13—C12—H12B	108.4
C8—C7—C6	106.7 (3)	H12A—C12—H12B	107.5
C8—C7—C13	125.8 (3)	C7—C13—C12	114.3 (3)
C6—C7—C13	127.4 (3)	C7—C13—H13A	108.7
C7—C8—N1	109.8 (3)	C12—C13—H13A	108.7
C7—C8—C9	128.9 (3)	C7—C13—H13B	108.7
N1—C8—C9	121.3 (3)	C12—C13—H13B	108.7
C8—C9—C10	112.9 (3)	H13A—C13—H13B	107.6
C8—C9—H9A	109.0
C8—N1—C1—C2	−179.8 (3)	C1—C6—C7—C8	−0.1 (3)
C8—N1—C1—C6	0.6 (3)	C5—C6—C7—C13	2.2 (6)
N1—C1—C2—C3	−179.2 (3)	C1—C6—C7—C13	−177.5 (3)
C6—C1—C2—C3	0.3 (5)	C6—C7—C8—N1	0.4 (4)
N1—C1—C2—Cl1	0.7 (5)	C13—C7—C8—N1	177.9 (3)
C6—C1—C2—Cl1	−179.7 (2)	C6—C7—C8—C9	−178.3 (3)
C1—C2—C3—C4	−0.5 (5)	C13—C7—C8—C9	−0.9 (5)
Cl1—C2—C3—C4	179.6 (3)	C1—N1—C8—C7	−0.6 (4)
C2—C3—C4—C5	0.0 (5)	C1—N1—C8—C9	178.2 (3)
C3—C4—C5—C6	0.7 (5)	C7—C8—C9—C10	54.0 (5)
C4—C5—C6—C1	−0.8 (5)	N1—C8—C9—C10	−124.6 (3)
C4—C5—C6—C7	179.5 (3)	C8—C9—C10—C11	−71.1 (4)
N1—C1—C6—C5	179.9 (3)	C9—C10—C11—C12	69.6 (4)
C2—C1—C6—C5	0.3 (5)	C10—C11—C12—C13	−68.4 (4)
N1—C1—C6—C7	−0.3 (3)	C8—C7—C13—C12	−52.5 (5)
C2—C1—C6—C7	−179.9 (3)	C6—C7—C13—C12	124.4 (3)
C5—C6—C7—C8	179.6 (3)	C11—C12—C13—C7	70.0 (4)

(HpCL3)

Crystal data

C13H14ClN	F(000) = 464
Mr = 219.70	Dx = 1.393 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5151 reflections
a = 12.1278 (11) Å	θ = 3.1–30.5°
b = 8.1084 (7) Å	µ = 0.33 mm^−1
c = 11.2668 (10) Å	T = 100 K
β = 108.995 (2)°	PLATE, colourless
V = 1047.61 (16) Å^3	0.51 × 0.32 × 0.18 mm
Z = 4

Data collection

Bruker APEX-II CCD diffractometer	3176 independent reflections
Radiation source: fine-focus sealed tube	2619 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 30.5°, θmin = 3.1°
Absorption correction: multi-scan SADABS	h = −17→16
Tmin = 0.851, Tmax = 0.944	k = −9→11
9700 measured reflections	l = −16→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: inferred from neighbouring sites
wR(F^2) = 0.098	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.046P)^2 + 0.3172P] where P = (Fo^2 + 2Fc^2)/3
3176 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.45 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl1	0.14167 (2)	0.11360 (4)	0.54252 (3)	0.01942 (10)
N1	0.58708 (8)	0.01534 (12)	0.75259 (9)	0.0138 (2)
H1	0.5892	−0.0566	0.8118	0.017*
C1	0.48762 (10)	0.08207 (14)	0.67010 (11)	0.0126 (2)
C2	0.37103 (10)	0.05571 (15)	0.65859 (11)	0.0141 (2)
H2	0.3487	−0.0170	0.7129	0.017*
C3	0.28970 (10)	0.14136 (15)	0.56376 (12)	0.0145 (2)
C4	0.32036 (11)	0.24875 (15)	0.48210 (12)	0.0159 (2)
H4	0.2614	0.3041	0.4177	0.019*
C5	0.43702 (11)	0.27412 (15)	0.49547 (11)	0.0149 (2)
H5	0.4583	0.3466	0.4403	0.018*
C6	0.52293 (10)	0.19179 (14)	0.59103 (11)	0.0127 (2)
C7	0.64825 (10)	0.18824 (14)	0.63056 (11)	0.0132 (2)
C8	0.68402 (10)	0.07884 (15)	0.72836 (11)	0.0134 (2)
C9	0.80265 (10)	0.01759 (15)	0.80233 (12)	0.0165 (2)
H9A	0.8257	−0.0684	0.7526	0.020*
H9B	0.7982	−0.0353	0.8798	0.020*
C10	0.89796 (10)	0.14886 (16)	0.83913 (12)	0.0171 (2)
H10A	0.9699	0.0983	0.8964	0.020*
H10B	0.8737	0.2368	0.8864	0.020*
C11	0.92656 (11)	0.22812 (17)	0.72945 (12)	0.0199 (3)
H11A	0.9350	0.1397	0.6725	0.024*
H11B	1.0028	0.2848	0.7627	0.024*
C12	0.83606 (11)	0.35218 (16)	0.65310 (12)	0.0178 (2)
H12A	0.8176	0.4292	0.7122	0.021*
H12B	0.8717	0.4177	0.6009	0.021*
C13	0.72194 (10)	0.27888 (15)	0.56736 (11)	0.0159 (2)
H13A	0.6746	0.3694	0.5169	0.019*
H13B	0.7406	0.2020	0.5083	0.019*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.01316 (14)	0.01847 (16)	0.02327 (17)	−0.00035 (10)	0.00129 (11)	−0.00036 (12)
N1	0.0143 (5)	0.0137 (5)	0.0122 (5)	−0.0002 (4)	0.0025 (4)	0.0038 (4)
C1	0.0156 (5)	0.0108 (5)	0.0099 (5)	0.0001 (4)	0.0022 (4)	−0.0007 (4)
C2	0.0158 (5)	0.0126 (5)	0.0131 (5)	−0.0011 (4)	0.0034 (4)	−0.0007 (5)
C3	0.0133 (5)	0.0130 (5)	0.0150 (5)	−0.0007 (4)	0.0015 (4)	−0.0037 (4)
C4	0.0179 (6)	0.0126 (5)	0.0131 (5)	0.0013 (4)	−0.0007 (4)	−0.0003 (5)
C5	0.0199 (6)	0.0117 (5)	0.0113 (5)	−0.0006 (4)	0.0026 (4)	0.0004 (4)
C6	0.0163 (5)	0.0102 (5)	0.0110 (5)	−0.0008 (4)	0.0036 (4)	−0.0018 (4)
C7	0.0152 (5)	0.0118 (5)	0.0121 (5)	−0.0013 (4)	0.0036 (4)	−0.0016 (4)
C8	0.0144 (5)	0.0115 (5)	0.0134 (5)	−0.0008 (4)	0.0035 (4)	−0.0014 (4)
C9	0.0150 (5)	0.0141 (6)	0.0184 (6)	0.0015 (4)	0.0028 (5)	0.0014 (5)
C10	0.0132 (5)	0.0193 (6)	0.0168 (6)	0.0003 (4)	0.0023 (4)	−0.0003 (5)
C11	0.0154 (5)	0.0251 (7)	0.0194 (6)	−0.0032 (5)	0.0060 (5)	−0.0010 (5)
C12	0.0205 (6)	0.0178 (6)	0.0157 (6)	−0.0054 (5)	0.0069 (5)	−0.0010 (5)
C13	0.0190 (6)	0.0151 (6)	0.0134 (5)	−0.0025 (4)	0.0049 (4)	0.0007 (5)

Geometric parameters (Å, º)

Cl1—C3	1.7468 (12)	C8—C9	1.4935 (16)
N1—C1	1.3718 (15)	C9—C10	1.5261 (17)
N1—C8	1.3896 (15)	C9—H9A	0.9900
N1—H1	0.8800	C9—H9B	0.9900
C1—C2	1.3937 (16)	C10—C11	1.5294 (18)
C1—C6	1.4202 (16)	C10—H10A	0.9900
C2—C3	1.3822 (17)	C10—H10B	0.9900
C2—H2	0.9500	C11—C12	1.5303 (19)
C3—C4	1.4019 (18)	C11—H11A	0.9900
C4—C5	1.3886 (17)	C11—H11B	0.9900
C4—H4	0.9500	C12—C13	1.5270 (17)
C5—C6	1.4001 (16)	C12—H12A	0.9900
C5—H5	0.9500	C12—H12B	0.9900
C6—C7	1.4382 (16)	C13—H13A	0.9900
C7—C8	1.3704 (17)	C13—H13B	0.9900
C7—C13	1.5033 (16)
C1—N1—C8	109.53 (10)	C10—C9—H9A	108.5
C1—N1—H1	125.2	C8—C9—H9B	108.5
C8—N1—H1	125.2	C10—C9—H9B	108.5
N1—C1—C2	130.11 (11)	H9A—C9—H9B	107.5
N1—C1—C6	107.09 (10)	C9—C10—C11	115.12 (11)
C2—C1—C6	122.80 (11)	C9—C10—H10A	108.5
C3—C2—C1	116.22 (11)	C11—C10—H10A	108.5
C3—C2—H2	121.9	C9—C10—H10B	108.5
C1—C2—H2	121.9	C11—C10—H10B	108.5
C2—C3—C4	122.99 (11)	H10A—C10—H10B	107.5
C2—C3—Cl1	118.95 (10)	C10—C11—C12	114.87 (10)
C4—C3—Cl1	118.06 (9)	C10—C11—H11A	108.5
C5—C4—C3	119.95 (11)	C12—C11—H11A	108.5
C5—C4—H4	120.0	C10—C11—H11B	108.5
C3—C4—H4	120.0	C12—C11—H11B	108.5
C4—C5—C6	119.33 (11)	H11A—C11—H11B	107.5
C4—C5—H5	120.3	C13—C12—C11	115.87 (11)
C6—C5—H5	120.3	C13—C12—H12A	108.3
C5—C6—C1	118.69 (11)	C11—C12—H12A	108.3
C5—C6—C7	134.00 (11)	C13—C12—H12B	108.3
C1—C6—C7	107.30 (10)	C11—C12—H12B	108.3
C8—C7—C6	106.74 (10)	H12A—C12—H12B	107.4
C8—C7—C13	128.02 (11)	C7—C13—C12	116.54 (10)
C6—C7—C13	125.08 (11)	C7—C13—H13A	108.2
C7—C8—N1	109.34 (10)	C12—C13—H13A	108.2
C7—C8—C9	131.24 (11)	C7—C13—H13B	108.2
N1—C8—C9	119.35 (11)	C12—C13—H13B	108.2
C8—C9—C10	115.25 (10)	H13A—C13—H13B	107.3
C8—C9—H9A	108.5
C8—N1—C1—C2	−179.98 (12)	C5—C6—C7—C13	−2.4 (2)
C8—N1—C1—C6	−0.07 (13)	C1—C6—C7—C13	176.22 (11)
N1—C1—C2—C3	−179.29 (12)	C6—C7—C8—N1	−0.64 (13)
C6—C1—C2—C3	0.82 (17)	C13—C7—C8—N1	−176.10 (11)
C1—C2—C3—C4	0.31 (18)	C6—C7—C8—C9	176.28 (12)
C1—C2—C3—Cl1	179.49 (9)	C13—C7—C8—C9	0.8 (2)
C2—C3—C4—C5	−0.67 (19)	C1—N1—C8—C7	0.46 (13)
Cl1—C3—C4—C5	−179.86 (9)	C1—N1—C8—C9	−176.88 (10)
C3—C4—C5—C6	−0.10 (18)	C7—C8—C9—C10	42.59 (19)
C4—C5—C6—C1	1.16 (17)	N1—C8—C9—C10	−140.74 (11)
C4—C5—C6—C7	179.61 (12)	C8—C9—C10—C11	−65.39 (15)
N1—C1—C6—C5	178.52 (10)	C9—C10—C11—C12	74.90 (14)
C2—C1—C6—C5	−1.56 (17)	C10—C11—C12—C13	−73.40 (14)
N1—C1—C6—C7	−0.31 (13)	C8—C7—C13—C12	−42.89 (18)
C2—C1—C6—C7	179.60 (11)	C6—C7—C13—C12	142.42 (12)
C5—C6—C7—C8	−177.99 (13)	C11—C12—C13—C7	63.88 (15)
C1—C6—C7—C8	0.59 (13)

(HpCL4)

Crystal data

C26H28Cl2N2	F(000) = 928
Mr = 439.40	Dx = 1.340 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9918 reflections
a = 9.8035 (5) Å	θ = 2.7–30.5°
b = 22.7092 (12) Å	µ = 0.31 mm^−1
c = 9.9786 (6) Å	T = 100 K
β = 101.405 (2)°	PLATE, colourless
V = 2177.7 (2) Å^3	0.43 × 0.28 × 0.15 mm
Z = 4

Data collection

Bruker APEX-II CCD diffractometer	6657 independent reflections
Radiation source: fine-focus sealed tube	5351 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 30.6°, θmin = 2.3°
Absorption correction: multi-scan SADABS	h = −13→14
Tmin = 0.877, Tmax = 0.954	k = −32→32
30504 measured reflections	l = −14→14

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0428P)^2 + 0.8539P] where P = (Fo^2 + 2Fc^2)/3
6657 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.42 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl1	0.16113 (3)	−0.105318 (13)	0.09600 (3)	0.02383 (8)
Cl2	0.06028 (4)	0.206920 (14)	0.64757 (4)	0.02666 (9)
N1	0.32298 (11)	0.10366 (4)	0.42810 (11)	0.0168 (2)
H1	0.3551	0.1096	0.5158	0.020*
N2	0.44333 (10)	0.01285 (5)	0.82468 (11)	0.0196 (2)
H2	0.5339	0.0102	0.8541	0.024*
C1	0.29819 (12)	0.04944 (5)	0.36662 (12)	0.0152 (2)
C2	0.31199 (13)	−0.00662 (5)	0.42355 (13)	0.0186 (2)
H2A	0.3474	−0.0123	0.5184	0.022*
C3	0.27210 (13)	−0.05394 (5)	0.33662 (14)	0.0194 (2)
H3	0.2804	−0.0930	0.3715	0.023*
C4	0.21957 (12)	−0.04408 (5)	0.19725 (13)	0.0170 (2)
C5	0.20915 (12)	0.01115 (5)	0.13837 (13)	0.0158 (2)
H5	0.1764	0.0163	0.0429	0.019*
C6	0.24892 (11)	0.05955 (5)	0.22516 (12)	0.0142 (2)
C7	0.24567 (12)	0.12218 (5)	0.20414 (12)	0.0153 (2)
C8	0.28944 (12)	0.14742 (5)	0.33024 (13)	0.0157 (2)
C9	0.30181 (13)	0.21097 (5)	0.36927 (14)	0.0198 (2)
H9A	0.3845	0.2277	0.3401	0.024*
H9B	0.3169	0.2141	0.4701	0.024*
C10	0.17374 (14)	0.24760 (5)	0.30626 (14)	0.0219 (3)
H10A	0.0898	0.2277	0.3254	0.026*
H10B	0.1807	0.2865	0.3520	0.026*
C11	0.15443 (14)	0.25738 (5)	0.15225 (15)	0.0228 (3)
H11A	0.2443	0.2705	0.1316	0.027*
H11B	0.0867	0.2897	0.1262	0.027*
C12	0.10420 (13)	0.20379 (5)	0.06284 (14)	0.0212 (3)
H12A	0.0194	0.1882	0.0901	0.025*
H12B	0.0775	0.2171	−0.0333	0.025*
C13	0.20896 (13)	0.15351 (6)	0.06927 (13)	0.0198 (2)
H13A	0.1708	0.1243	−0.0020	0.024*
H13B	0.2955	0.1695	0.0465	0.024*
C14	0.37166 (12)	0.06421 (5)	0.78873 (13)	0.0172 (2)
C15	0.41828 (13)	0.12215 (6)	0.78713 (13)	0.0200 (2)
H15	0.5142	0.1315	0.8145	0.024*
C16	0.32024 (14)	0.16573 (6)	0.74435 (13)	0.0206 (3)
H16	0.3484	0.2057	0.7425	0.025*
C17	0.17952 (13)	0.15060 (5)	0.70386 (13)	0.0188 (2)
C18	0.13122 (12)	0.09357 (5)	0.70514 (12)	0.0170 (2)
H18	0.0350	0.0848	0.6777	0.020*
C19	0.22912 (12)	0.04893 (5)	0.74841 (12)	0.0152 (2)
C20	0.21868 (12)	−0.01379 (5)	0.76100 (13)	0.0160 (2)
C21	0.35155 (12)	−0.03410 (6)	0.80770 (13)	0.0178 (2)
C22	0.40245 (13)	−0.09576 (6)	0.83594 (15)	0.0227 (3)
H22A	0.3714	−0.1103	0.9185	0.027*
H22B	0.5055	−0.0956	0.8557	0.027*
C23	0.35115 (14)	−0.13812 (6)	0.71786 (16)	0.0251 (3)
H23A	0.4042	−0.1754	0.7356	0.030*
H23B	0.3719	−0.1209	0.6330	0.030*
C24	0.19567 (14)	−0.15237 (6)	0.69423 (16)	0.0259 (3)
H24A	0.1776	−0.1866	0.6319	0.031*
H24B	0.1732	−0.1645	0.7827	0.031*
C25	0.09598 (13)	−0.10292 (6)	0.63475 (14)	0.0215 (3)
H25A	0.1236	−0.0885	0.5503	0.026*
H25B	0.0014	−0.1198	0.6080	0.026*
C26	0.08842 (12)	−0.05017 (5)	0.72794 (13)	0.0185 (2)
H26A	0.0109	−0.0244	0.6838	0.022*
H26B	0.0659	−0.0646	0.8146	0.022*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.02640 (16)	0.01897 (14)	0.02623 (17)	−0.00167 (11)	0.00544 (13)	−0.00661 (11)
Cl2	0.03049 (17)	0.02073 (15)	0.02851 (19)	0.00787 (12)	0.00522 (14)	−0.00213 (12)
N1	0.0185 (5)	0.0195 (5)	0.0118 (5)	−0.0019 (4)	0.0014 (4)	−0.0010 (4)
N2	0.0105 (4)	0.0264 (5)	0.0210 (6)	−0.0003 (4)	0.0008 (4)	0.0038 (4)
C1	0.0127 (5)	0.0196 (5)	0.0138 (6)	−0.0013 (4)	0.0040 (4)	−0.0012 (4)
C2	0.0192 (6)	0.0220 (6)	0.0153 (6)	0.0002 (4)	0.0049 (5)	0.0025 (4)
C3	0.0197 (6)	0.0181 (5)	0.0219 (6)	0.0000 (4)	0.0076 (5)	0.0024 (5)
C4	0.0143 (5)	0.0180 (5)	0.0196 (6)	−0.0009 (4)	0.0051 (5)	−0.0046 (4)
C5	0.0128 (5)	0.0202 (5)	0.0144 (6)	0.0015 (4)	0.0029 (4)	−0.0020 (4)
C6	0.0111 (5)	0.0183 (5)	0.0141 (6)	0.0010 (4)	0.0045 (4)	0.0007 (4)
C7	0.0137 (5)	0.0182 (5)	0.0144 (6)	0.0012 (4)	0.0038 (4)	0.0000 (4)
C8	0.0124 (5)	0.0186 (5)	0.0163 (6)	−0.0007 (4)	0.0035 (4)	0.0006 (4)
C9	0.0200 (6)	0.0187 (6)	0.0198 (6)	−0.0040 (4)	0.0018 (5)	−0.0030 (5)
C10	0.0226 (6)	0.0161 (5)	0.0269 (7)	−0.0007 (4)	0.0049 (5)	−0.0047 (5)
C11	0.0221 (6)	0.0176 (6)	0.0278 (7)	0.0012 (5)	0.0029 (5)	0.0021 (5)
C12	0.0197 (6)	0.0212 (6)	0.0212 (7)	0.0047 (5)	0.0008 (5)	0.0018 (5)
C13	0.0217 (6)	0.0224 (6)	0.0155 (6)	0.0055 (5)	0.0041 (5)	0.0020 (5)
C14	0.0143 (5)	0.0234 (6)	0.0140 (6)	−0.0004 (4)	0.0032 (4)	−0.0005 (4)
C15	0.0183 (6)	0.0261 (6)	0.0155 (6)	−0.0056 (5)	0.0032 (5)	−0.0031 (5)
C16	0.0255 (6)	0.0205 (6)	0.0164 (6)	−0.0037 (5)	0.0061 (5)	−0.0038 (4)
C17	0.0224 (6)	0.0196 (6)	0.0150 (6)	0.0045 (5)	0.0050 (5)	−0.0017 (4)
C18	0.0147 (5)	0.0225 (6)	0.0139 (6)	0.0014 (4)	0.0036 (4)	−0.0016 (4)
C19	0.0132 (5)	0.0210 (6)	0.0115 (6)	−0.0005 (4)	0.0032 (4)	−0.0014 (4)
C20	0.0122 (5)	0.0206 (5)	0.0157 (6)	0.0002 (4)	0.0038 (4)	0.0013 (4)
C21	0.0128 (5)	0.0243 (6)	0.0169 (6)	0.0003 (4)	0.0042 (5)	0.0040 (5)
C22	0.0142 (5)	0.0261 (6)	0.0283 (7)	0.0038 (5)	0.0052 (5)	0.0109 (5)
C23	0.0238 (6)	0.0205 (6)	0.0338 (8)	0.0053 (5)	0.0128 (6)	0.0061 (5)
C24	0.0249 (7)	0.0204 (6)	0.0336 (8)	−0.0017 (5)	0.0088 (6)	0.0027 (5)
C25	0.0198 (6)	0.0226 (6)	0.0224 (7)	−0.0041 (5)	0.0048 (5)	0.0009 (5)
C26	0.0124 (5)	0.0226 (6)	0.0205 (6)	−0.0011 (4)	0.0037 (5)	0.0021 (5)

Geometric parameters (Å, º)

Cl1—C4	1.7475 (12)	C12—H12A	0.9900
Cl2—C17	1.7488 (13)	C12—H12B	0.9900
N1—C1	1.3757 (15)	C13—H13A	0.9900
N1—C8	1.3865 (16)	C13—H13B	0.9900
N1—H1	0.8800	C14—C15	1.3941 (17)
N2—C14	1.3722 (16)	C14—C19	1.4187 (16)
N2—C21	1.3837 (16)	C15—C16	1.3868 (18)
N2—H2	0.8800	C15—H15	0.9500
C1—C2	1.3897 (17)	C16—C17	1.4015 (18)
C1—C6	1.4173 (17)	C16—H16	0.9500
C2—C3	1.3877 (18)	C17—C18	1.3798 (17)
C2—H2A	0.9500	C18—C19	1.4040 (16)
C3—C4	1.4022 (18)	C18—H18	0.9500
C3—H3	0.9500	C19—C20	1.4353 (16)
C4—C5	1.3803 (17)	C20—C21	1.3735 (16)
C5—C6	1.4059 (16)	C20—C26	1.5019 (16)
C5—H5	0.9500	C21—C22	1.4946 (17)
C6—C7	1.4370 (16)	C22—C23	1.527 (2)
C7—C8	1.3722 (17)	C22—H22A	0.9900
C7—C13	1.5018 (17)	C22—H22B	0.9900
C8—C9	1.4934 (16)	C23—C24	1.5302 (19)
C9—C10	1.5334 (18)	C23—H23A	0.9900
C9—H9A	0.9900	C23—H23B	0.9900
C9—H9B	0.9900	C24—C25	1.5295 (19)
C10—C11	1.527 (2)	C24—H24A	0.9900
C10—H10A	0.9900	C24—H24B	0.9900
C10—H10B	0.9900	C25—C26	1.5273 (18)
C11—C12	1.5315 (18)	C25—H25A	0.9900
C11—H11A	0.9900	C25—H25B	0.9900
C11—H11B	0.9900	C26—H26A	0.9900
C12—C13	1.5286 (17)	C26—H26B	0.9900
C1—N1—C8	109.34 (10)	C7—C13—H13B	108.4
C1—N1—H1	125.3	C12—C13—H13B	108.4
C8—N1—H1	125.3	H13A—C13—H13B	107.5
C14—N2—C21	109.63 (10)	N2—C14—C15	130.78 (11)
C14—N2—H2	125.2	N2—C14—C19	106.92 (10)
C21—N2—H2	125.2	C15—C14—C19	122.29 (11)
N1—C1—C2	130.04 (11)	C16—C15—C14	117.92 (11)
N1—C1—C6	107.13 (10)	C16—C15—H15	121.0
C2—C1—C6	122.81 (11)	C14—C15—H15	121.0
C3—C2—C1	117.47 (12)	C15—C16—C17	119.77 (11)
C3—C2—H2A	121.3	C15—C16—H16	120.1
C1—C2—H2A	121.3	C17—C16—H16	120.1
C2—C3—C4	119.95 (11)	C18—C17—C16	123.20 (11)
C2—C3—H3	120.0	C18—C17—Cl2	118.73 (10)
C4—C3—H3	120.0	C16—C17—Cl2	118.07 (10)
C5—C4—C3	123.29 (11)	C17—C18—C19	117.75 (11)
C5—C4—Cl1	119.26 (10)	C17—C18—H18	121.1
C3—C4—Cl1	117.43 (9)	C19—C18—H18	121.1
C4—C5—C6	117.39 (11)	C18—C19—C14	119.06 (11)
C4—C5—H5	121.3	C18—C19—C20	133.41 (11)
C6—C5—H5	121.3	C14—C19—C20	107.52 (10)
C5—C6—C1	119.03 (11)	C21—C20—C19	106.48 (10)
C5—C6—C7	133.50 (11)	C21—C20—C26	126.72 (11)
C1—C6—C7	107.40 (10)	C19—C20—C26	126.79 (10)
C8—C7—C6	106.60 (10)	C20—C21—N2	109.45 (11)
C8—C7—C13	126.86 (11)	C20—C21—C22	129.60 (11)
C6—C7—C13	126.46 (11)	N2—C21—C22	120.93 (10)
C7—C8—N1	109.51 (10)	C21—C22—C23	113.45 (11)
C7—C8—C9	129.60 (11)	C21—C22—H22A	108.9
N1—C8—C9	120.88 (11)	C23—C22—H22A	108.9
C8—C9—C10	113.55 (10)	C21—C22—H22B	108.9
C8—C9—H9A	108.9	C23—C22—H22B	108.9
C10—C9—H9A	108.9	H22A—C22—H22B	107.7
C8—C9—H9B	108.9	C22—C23—C24	114.72 (11)
C10—C9—H9B	108.9	C22—C23—H23A	108.6
H9A—C9—H9B	107.7	C24—C23—H23A	108.6
C11—C10—C9	114.84 (11)	C22—C23—H23B	108.6
C11—C10—H10A	108.6	C24—C23—H23B	108.6
C9—C10—H10A	108.6	H23A—C23—H23B	107.6
C11—C10—H10B	108.6	C25—C24—C23	116.43 (11)
C9—C10—H10B	108.6	C25—C24—H24A	108.2
H10A—C10—H10B	107.5	C23—C24—H24A	108.2
C10—C11—C12	115.61 (11)	C25—C24—H24B	108.2
C10—C11—H11A	108.4	C23—C24—H24B	108.2
C12—C11—H11A	108.4	H24A—C24—H24B	107.3
C10—C11—H11B	108.4	C26—C25—C24	116.35 (11)
C12—C11—H11B	108.4	C26—C25—H25A	108.2
H11A—C11—H11B	107.4	C24—C25—H25A	108.2
C13—C12—C11	115.67 (11)	C26—C25—H25B	108.2
C13—C12—H12A	108.4	C24—C25—H25B	108.2
C11—C12—H12A	108.4	H25A—C25—H25B	107.4
C13—C12—H12B	108.4	C20—C26—C25	115.07 (10)
C11—C12—H12B	108.4	C20—C26—H26A	108.5
H12A—C12—H12B	107.4	C25—C26—H26A	108.5
C7—C13—C12	115.56 (11)	C20—C26—H26B	108.5
C7—C13—H13A	108.4	C25—C26—H26B	108.5
C12—C13—H13A	108.4	H26A—C26—H26B	107.5
C8—N1—C1—C2	−177.75 (12)	C21—N2—C14—C15	−179.23 (13)
C8—N1—C1—C6	0.66 (13)	C21—N2—C14—C19	0.38 (14)
N1—C1—C2—C3	176.66 (12)	N2—C14—C15—C16	179.59 (13)
C6—C1—C2—C3	−1.53 (18)	C19—C14—C15—C16	0.02 (19)
C1—C2—C3—C4	−0.32 (18)	C14—C15—C16—C17	−0.35 (19)
C2—C3—C4—C5	2.37 (19)	C15—C16—C17—C18	0.6 (2)
C2—C3—C4—Cl1	−176.03 (9)	C15—C16—C17—Cl2	−178.77 (10)
C3—C4—C5—C6	−2.42 (17)	C16—C17—C18—C19	−0.48 (19)
Cl1—C4—C5—C6	175.95 (8)	Cl2—C17—C18—C19	178.88 (9)
C4—C5—C6—C1	0.53 (16)	C17—C18—C19—C14	0.14 (17)
C4—C5—C6—C7	−175.96 (12)	C17—C18—C19—C20	−178.86 (13)
N1—C1—C6—C5	−177.10 (10)	N2—C14—C19—C18	−179.57 (11)
C2—C1—C6—C5	1.45 (17)	C15—C14—C19—C18	0.08 (18)
N1—C1—C6—C7	0.22 (12)	N2—C14—C19—C20	−0.33 (13)
C2—C1—C6—C7	178.78 (11)	C15—C14—C19—C20	179.32 (11)
C5—C6—C7—C8	175.75 (12)	C18—C19—C20—C21	179.25 (13)
C1—C6—C7—C8	−1.02 (12)	C14—C19—C20—C21	0.17 (14)
C5—C6—C7—C13	−7.3 (2)	C18—C19—C20—C26	0.0 (2)
C1—C6—C7—C13	175.94 (11)	C14—C19—C20—C26	−179.12 (12)
C6—C7—C8—N1	1.45 (13)	C19—C20—C21—N2	0.06 (14)
C13—C7—C8—N1	−175.50 (11)	C26—C20—C21—N2	179.35 (11)
C6—C7—C8—C9	−177.80 (12)	C19—C20—C21—C22	−178.40 (13)
C13—C7—C8—C9	5.3 (2)	C26—C20—C21—C22	0.9 (2)
C1—N1—C8—C7	−1.35 (13)	C14—N2—C21—C20	−0.28 (15)
C1—N1—C8—C9	177.97 (10)	C14—N2—C21—C22	178.34 (11)
C7—C8—C9—C10	46.48 (18)	C20—C21—C22—C23	50.51 (18)
N1—C8—C9—C10	−132.69 (12)	N2—C21—C22—C23	−127.79 (13)
C8—C9—C10—C11	−70.53 (14)	C21—C22—C23—C24	−70.17 (14)
C9—C10—C11—C12	73.62 (14)	C22—C23—C24—C25	71.24 (16)
C10—C11—C12—C13	−69.35 (15)	C23—C24—C25—C26	−68.78 (16)
C8—C7—C13—C12	−51.75 (17)	C21—C20—C26—C25	−49.95 (18)
C6—C7—C13—C12	131.88 (12)	C19—C20—C26—C25	129.19 (13)
C11—C12—C13—C7	66.45 (15)	C24—C25—C26—C20	66.80 (15)

(HpF2)

Crystal data

C13H14FN	F(000) = 864
Mr = 203.25	Dx = 1.325 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 9989 reflections
a = 11.9582 (11) Å	θ = 2.8–30.5°
b = 9.1060 (9) Å	µ = 0.09 mm^−1
c = 18.7079 (19) Å	T = 100 K
V = 2037.1 (3) Å^3	PLATE, colourless
Z = 8	0.51 × 0.33 × 0.15 mm

Data collection

Bruker APEX-II CCD diffractometer	3125 independent reflections
Radiation source: fine-focus sealed tube	2724 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 30.6°, θmin = 2.8°
Absorption correction: multi-scan SADABS	h = −16→17
Tmin = 0.956, Tmax = 0.987	k = −12→13
40673 measured reflections	l = −26→26

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0601P)^2 + 0.8099P] where P = (Fo^2 + 2Fc^2)/3
3125 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.40 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
F1	0.28463 (5)	0.30858 (8)	0.30501 (3)	0.02404 (16)
N1	0.23030 (7)	0.41777 (9)	0.45027 (4)	0.01562 (17)
H1	0.2897	0.4673	0.4365	0.019*
C1	0.17733 (8)	0.31075 (10)	0.41148 (5)	0.01519 (18)
C2	0.19801 (8)	0.25362 (11)	0.34380 (5)	0.0182 (2)
C3	0.13219 (9)	0.14421 (12)	0.31622 (5)	0.0215 (2)
H3	0.1466	0.1061	0.2699	0.026*
C4	0.04295 (9)	0.08880 (12)	0.35735 (5)	0.0214 (2)
H4	−0.0023	0.0125	0.3383	0.026*
C5	0.01973 (8)	0.14325 (11)	0.42501 (5)	0.0183 (2)
H5	−0.0407	0.1049	0.4522	0.022*
C6	0.08717 (8)	0.25624 (10)	0.45273 (5)	0.01471 (18)
C7	0.08703 (8)	0.33781 (10)	0.51866 (5)	0.01427 (18)
C8	0.17466 (8)	0.43510 (10)	0.51498 (5)	0.01473 (18)
C9	0.21103 (9)	0.55190 (11)	0.56604 (5)	0.01872 (19)
H9A	0.1589	0.6360	0.5622	0.022*
H9B	0.2861	0.5869	0.5517	0.022*
C10	0.21568 (9)	0.50240 (13)	0.64409 (5)	0.0212 (2)
H10A	0.2517	0.5809	0.6726	0.025*
H10B	0.2639	0.4143	0.6472	0.025*
C11	0.10252 (9)	0.46627 (12)	0.67800 (5)	0.0213 (2)
H11A	0.1120	0.4631	0.7305	0.026*
H11B	0.0498	0.5470	0.6670	0.026*
C12	0.05007 (8)	0.32152 (11)	0.65371 (5)	0.01695 (19)
H12A	−0.0109	0.2960	0.6873	0.020*
H12B	0.1074	0.2434	0.6572	0.020*
C13	0.00273 (8)	0.32135 (11)	0.57774 (5)	0.01688 (19)
H13A	−0.0383	0.2282	0.5703	0.020*
H13B	−0.0521	0.4023	0.5737	0.020*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0235 (3)	0.0309 (4)	0.0177 (3)	−0.0003 (3)	0.0071 (2)	−0.0008 (2)
N1	0.0150 (4)	0.0182 (4)	0.0137 (3)	−0.0014 (3)	0.0025 (3)	0.0006 (3)
C1	0.0155 (4)	0.0156 (4)	0.0144 (4)	0.0019 (3)	−0.0009 (3)	0.0011 (3)
C2	0.0183 (4)	0.0213 (5)	0.0149 (4)	0.0033 (4)	0.0015 (3)	0.0013 (3)
C3	0.0260 (5)	0.0234 (5)	0.0151 (4)	0.0035 (4)	−0.0017 (4)	−0.0031 (3)
C4	0.0248 (5)	0.0201 (5)	0.0193 (5)	−0.0006 (4)	−0.0050 (4)	−0.0021 (3)
C5	0.0184 (4)	0.0184 (4)	0.0181 (4)	−0.0014 (3)	−0.0024 (3)	0.0018 (3)
C6	0.0151 (4)	0.0153 (4)	0.0138 (4)	0.0016 (3)	−0.0013 (3)	0.0022 (3)
C7	0.0148 (4)	0.0153 (4)	0.0127 (4)	0.0014 (3)	0.0000 (3)	0.0016 (3)
C8	0.0157 (4)	0.0161 (4)	0.0125 (4)	0.0011 (3)	0.0012 (3)	0.0014 (3)
C9	0.0217 (5)	0.0177 (4)	0.0168 (4)	−0.0044 (4)	0.0026 (3)	−0.0009 (3)
C10	0.0211 (5)	0.0279 (5)	0.0147 (4)	−0.0082 (4)	0.0006 (3)	−0.0016 (3)
C11	0.0233 (5)	0.0252 (5)	0.0153 (4)	−0.0057 (4)	0.0053 (3)	−0.0031 (4)
C12	0.0172 (4)	0.0195 (4)	0.0141 (4)	−0.0014 (3)	0.0015 (3)	0.0020 (3)
C13	0.0143 (4)	0.0216 (4)	0.0148 (4)	−0.0012 (3)	0.0009 (3)	0.0024 (3)

Geometric parameters (Å, º)

F1—C2	1.3602 (11)	C8—C9	1.4943 (13)
N1—C1	1.3702 (12)	C9—C10	1.5292 (14)
N1—C8	1.3903 (11)	C9—H9A	0.9900
N1—H1	0.8800	C9—H9B	0.9900
C1—C2	1.3910 (13)	C10—C11	1.5302 (14)
C1—C6	1.4157 (13)	C10—H10A	0.9900
C2—C3	1.3704 (15)	C10—H10B	0.9900
C3—C4	1.4091 (15)	C11—C12	1.5288 (14)
C3—H3	0.9500	C11—H11A	0.9900
C4—C5	1.3875 (14)	C11—H11B	0.9900
C4—H4	0.9500	C12—C13	1.5298 (13)
C5—C6	1.4063 (13)	C12—H12A	0.9900
C5—H5	0.9500	C12—H12B	0.9900
C6—C7	1.4398 (13)	C13—H13A	0.9900
C7—C8	1.3739 (13)	C13—H13B	0.9900
C7—C13	1.5034 (13)
C1—N1—C8	108.71 (8)	C10—C9—H9A	108.7
C1—N1—H1	125.6	C8—C9—H9B	108.7
C8—N1—H1	125.6	C10—C9—H9B	108.7
N1—C1—C2	131.76 (9)	H9A—C9—H9B	107.6
N1—C1—C6	108.22 (8)	C9—C10—C11	115.28 (9)
C2—C1—C6	120.02 (9)	C9—C10—H10A	108.5
F1—C2—C3	120.27 (9)	C11—C10—H10A	108.5
F1—C2—C1	118.90 (9)	C9—C10—H10B	108.5
C3—C2—C1	120.83 (9)	C11—C10—H10B	108.5
C2—C3—C4	119.32 (9)	H10A—C10—H10B	107.5
C2—C3—H3	120.3	C12—C11—C10	115.15 (8)
C4—C3—H3	120.3	C12—C11—H11A	108.5
C5—C4—C3	121.45 (10)	C10—C11—H11A	108.5
C5—C4—H4	119.3	C12—C11—H11B	108.5
C3—C4—H4	119.3	C10—C11—H11B	108.5
C4—C5—C6	118.88 (9)	H11A—C11—H11B	107.5
C4—C5—H5	120.6	C11—C12—C13	115.39 (8)
C6—C5—H5	120.6	C11—C12—H12A	108.4
C5—C6—C1	119.49 (9)	C13—C12—H12A	108.4
C5—C6—C7	133.83 (9)	C11—C12—H12B	108.4
C1—C6—C7	106.68 (8)	C13—C12—H12B	108.4
C8—C7—C6	106.79 (8)	H12A—C12—H12B	107.5
C8—C7—C13	127.77 (8)	C7—C13—C12	115.77 (8)
C6—C7—C13	125.39 (8)	C7—C13—H13A	108.3
C7—C8—N1	109.59 (8)	C12—C13—H13A	108.3
C7—C8—C9	130.46 (8)	C7—C13—H13B	108.3
N1—C8—C9	119.88 (8)	C12—C13—H13B	108.3
C8—C9—C10	114.28 (8)	H13A—C13—H13B	107.4
C8—C9—H9A	108.7
C8—N1—C1—C2	178.96 (10)	C1—C6—C7—C8	−0.22 (10)
C8—N1—C1—C6	−1.17 (10)	C5—C6—C7—C13	−2.50 (17)
N1—C1—C2—F1	−0.61 (16)	C1—C6—C7—C13	177.37 (8)
C6—C1—C2—F1	179.53 (8)	C6—C7—C8—N1	−0.49 (10)
N1—C1—C2—C3	179.67 (10)	C13—C7—C8—N1	−178.00 (9)
C6—C1—C2—C3	−0.19 (14)	C6—C7—C8—C9	176.48 (9)
F1—C2—C3—C4	179.95 (9)	C13—C7—C8—C9	−1.04 (16)
C1—C2—C3—C4	−0.34 (15)	C1—N1—C8—C7	1.04 (11)
C2—C3—C4—C5	0.44 (16)	C1—N1—C8—C9	−176.30 (8)
C3—C4—C5—C6	0.01 (15)	C7—C8—C9—C10	46.55 (14)
C4—C5—C6—C1	−0.54 (14)	N1—C8—C9—C10	−136.75 (9)
C4—C5—C6—C7	179.31 (10)	C8—C9—C10—C11	−67.08 (12)
N1—C1—C6—C5	−179.25 (8)	C9—C10—C11—C12	73.96 (12)
C2—C1—C6—C5	0.64 (14)	C10—C11—C12—C13	−72.94 (12)
N1—C1—C6—C7	0.85 (10)	C8—C7—C13—C12	−45.08 (13)
C2—C1—C6—C7	−179.25 (8)	C6—C7—C13—C12	137.84 (9)
C5—C6—C7—C8	179.91 (10)	C11—C12—C13—C7	66.14 (11)

(HpF4)

Crystal data

C13H14FN	F(000) = 864
Mr = 203.25	Dx = 1.293 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9834 reflections
a = 9.8202 (6) Å	θ = 2.7–30.5°
b = 22.0098 (16) Å	µ = 0.09 mm^−1
c = 9.8725 (7) Å	T = 100 K
β = 101.926 (3)°	Plate, colourless
V = 2087.8 (2) Å^3	0.38 × 0.23 × 0.18 mm
Z = 8

Data collection

Bruker APEX-II CCD diffractometer	6387 independent reflections
Radiation source: fine-focus sealed tube	5327 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
φ and ω scans	θmax = 30.6°, θmin = 2.3°
Absorption correction: multi-scan SADABS	h = −14→14
Tmin = 0.967, Tmax = 0.984	k = −31→31
37051 measured reflections	l = −14→14

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0675P)^2 + 0.603P] where P = (Fo^2 + 2Fc^2)/3
6387 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.46 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
F2	0.57950 (9)	−0.19745 (3)	0.13961 (8)	0.0360 (2)
F1	0.67913 (8)	0.10483 (3)	0.60587 (8)	0.03093 (18)
N2	0.94130 (9)	−0.01375 (4)	0.32141 (9)	0.01817 (18)
H2	1.0320	−0.0117	0.3515	0.022*
N1	0.82442 (9)	−0.09860 (4)	0.91375 (9)	0.01812 (18)
H1	0.8586	−0.1055	1.0020	0.022*
C1	0.79655 (10)	−0.04228 (5)	0.85450 (10)	0.01598 (19)
C2	0.80980 (11)	0.01527 (5)	0.91390 (11)	0.0205 (2)
H2A	0.8452	0.0206	1.0102	0.025*
C3	0.76955 (12)	0.06450 (5)	0.82762 (12)	0.0223 (2)
H3	0.7764	0.1046	0.8642	0.027*
C4	0.71879 (11)	0.05488 (5)	0.68653 (12)	0.0208 (2)
C5	0.70590 (10)	−0.00113 (5)	0.62426 (11)	0.0187 (2)
H5	0.6719	−0.0056	0.5274	0.022*
C6	0.74542 (10)	−0.05168 (5)	0.71079 (10)	0.01545 (18)
C7	0.74262 (10)	−0.11576 (5)	0.68689 (10)	0.01707 (19)
C8	0.79030 (10)	−0.14284 (5)	0.81279 (10)	0.01708 (19)
C9	0.81055 (12)	−0.20850 (5)	0.84872 (12)	0.0219 (2)
H9A	0.8275	−0.2128	0.9507	0.026*
H9B	0.8948	−0.2230	0.8183	0.026*
C10	0.68803 (12)	−0.24920 (5)	0.78432 (13)	0.0246 (2)
H10A	0.6023	−0.2325	0.8080	0.030*
H10B	0.7034	−0.2900	0.8267	0.030*
C11	0.66430 (13)	−0.25601 (5)	0.62703 (13)	0.0268 (2)
H11A	0.7543	−0.2665	0.6027	0.032*
H11B	0.6005	−0.2907	0.5991	0.032*
C12	0.60448 (12)	−0.20062 (5)	0.54205 (12)	0.0244 (2)
H12A	0.5752	−0.2132	0.4440	0.029*
H12B	0.5201	−0.1872	0.5739	0.029*
C13	0.70253 (13)	−0.14648 (5)	0.54905 (11)	0.0256 (2)
H13A	0.7886	−0.1604	0.5211	0.031*
H13B	0.6580	−0.1160	0.4802	0.031*
C14	0.86793 (10)	−0.06571 (5)	0.27752 (10)	0.01663 (19)
C15	0.91322 (12)	−0.12547 (5)	0.26972 (11)	0.0208 (2)
H15	1.0090	−0.1357	0.2959	0.025*
C16	0.81346 (13)	−0.16937 (5)	0.22244 (11)	0.0242 (2)
H16	0.8399	−0.2106	0.2157	0.029*
C17	0.67383 (13)	−0.15243 (5)	0.18490 (11)	0.0238 (2)
C18	0.62600 (11)	−0.09432 (5)	0.19094 (11)	0.0203 (2)
H18	0.5298	−0.0849	0.1642	0.024*
C19	0.72560 (10)	−0.04908 (4)	0.23843 (10)	0.01553 (18)
C20	0.71688 (10)	0.01496 (5)	0.25987 (10)	0.01551 (18)
C21	0.85031 (10)	0.03480 (5)	0.31092 (10)	0.01642 (19)
C22	0.90088 (11)	0.09712 (5)	0.35317 (12)	0.0219 (2)
H22A	1.0039	0.0968	0.3759	0.026*
H22B	0.8683	0.1085	0.4382	0.026*
C23	0.85192 (13)	0.14538 (5)	0.24235 (13)	0.0265 (2)
H23A	0.8759	0.1317	0.1546	0.032*
H23B	0.9040	0.1834	0.2706	0.032*
C24	0.69607 (13)	0.15948 (5)	0.21512 (13)	0.0272 (2)
H24A	0.6712	0.1694	0.3048	0.033*
H24B	0.6792	0.1964	0.1567	0.033*
C25	0.59730 (12)	0.10983 (5)	0.14549 (12)	0.0240 (2)
H25A	0.6270	0.0972	0.0598	0.029*
H25B	0.5029	0.1275	0.1178	0.029*
C26	0.58811 (10)	0.05328 (5)	0.23277 (11)	0.0206 (2)
H26A	0.5678	0.0661	0.3226	0.025*
H26B	0.5091	0.0281	0.1851	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F2	0.0468 (5)	0.0233 (4)	0.0352 (4)	−0.0165 (3)	0.0019 (3)	−0.0031 (3)
F1	0.0370 (4)	0.0194 (3)	0.0365 (4)	0.0032 (3)	0.0078 (3)	0.0105 (3)
N2	0.0120 (4)	0.0201 (4)	0.0216 (4)	0.0006 (3)	0.0016 (3)	−0.0018 (3)
N1	0.0217 (4)	0.0191 (4)	0.0129 (4)	0.0005 (3)	0.0021 (3)	0.0009 (3)
C1	0.0153 (4)	0.0179 (4)	0.0154 (4)	−0.0003 (3)	0.0048 (3)	0.0006 (3)
C2	0.0227 (5)	0.0215 (5)	0.0189 (5)	−0.0020 (4)	0.0078 (4)	−0.0031 (4)
C3	0.0251 (5)	0.0171 (5)	0.0274 (5)	−0.0007 (4)	0.0117 (4)	−0.0024 (4)
C4	0.0194 (5)	0.0181 (5)	0.0263 (5)	0.0012 (4)	0.0081 (4)	0.0066 (4)
C5	0.0165 (4)	0.0215 (5)	0.0181 (4)	−0.0025 (3)	0.0031 (3)	0.0040 (4)
C6	0.0131 (4)	0.0175 (4)	0.0163 (4)	−0.0022 (3)	0.0042 (3)	0.0008 (3)
C7	0.0181 (4)	0.0173 (4)	0.0161 (4)	−0.0041 (3)	0.0040 (3)	−0.0002 (3)
C8	0.0175 (4)	0.0168 (4)	0.0171 (4)	−0.0012 (3)	0.0041 (3)	−0.0008 (4)
C9	0.0247 (5)	0.0179 (5)	0.0222 (5)	0.0021 (4)	0.0027 (4)	0.0030 (4)
C10	0.0271 (5)	0.0162 (5)	0.0311 (6)	−0.0021 (4)	0.0072 (4)	0.0037 (4)
C11	0.0292 (6)	0.0183 (5)	0.0318 (6)	−0.0035 (4)	0.0037 (5)	−0.0038 (4)
C12	0.0263 (5)	0.0217 (5)	0.0238 (5)	−0.0075 (4)	0.0019 (4)	−0.0025 (4)
C13	0.0346 (6)	0.0253 (5)	0.0169 (5)	−0.0128 (4)	0.0054 (4)	−0.0030 (4)
C14	0.0180 (4)	0.0172 (4)	0.0149 (4)	0.0002 (3)	0.0038 (3)	0.0007 (3)
C15	0.0262 (5)	0.0202 (5)	0.0164 (4)	0.0055 (4)	0.0054 (4)	0.0026 (4)
C16	0.0396 (6)	0.0162 (5)	0.0176 (5)	0.0014 (4)	0.0074 (4)	0.0021 (4)
C17	0.0345 (6)	0.0193 (5)	0.0170 (5)	−0.0101 (4)	0.0043 (4)	−0.0005 (4)
C18	0.0210 (5)	0.0230 (5)	0.0163 (4)	−0.0056 (4)	0.0025 (4)	−0.0002 (4)
C19	0.0160 (4)	0.0177 (4)	0.0128 (4)	−0.0006 (3)	0.0029 (3)	0.0009 (3)
C20	0.0139 (4)	0.0179 (4)	0.0148 (4)	0.0002 (3)	0.0030 (3)	−0.0003 (3)
C21	0.0149 (4)	0.0181 (4)	0.0166 (4)	0.0001 (3)	0.0040 (3)	−0.0020 (3)
C22	0.0187 (5)	0.0214 (5)	0.0255 (5)	−0.0037 (4)	0.0043 (4)	−0.0070 (4)
C23	0.0312 (6)	0.0178 (5)	0.0337 (6)	−0.0035 (4)	0.0142 (5)	−0.0027 (4)
C24	0.0341 (6)	0.0194 (5)	0.0301 (6)	0.0059 (4)	0.0112 (5)	0.0003 (4)
C25	0.0248 (5)	0.0255 (5)	0.0212 (5)	0.0093 (4)	0.0034 (4)	0.0008 (4)
C26	0.0145 (4)	0.0238 (5)	0.0233 (5)	0.0032 (4)	0.0031 (4)	−0.0011 (4)

Geometric parameters (Å, º)

F2—C17	1.3669 (12)	C12—H12A	0.9900
F1—C4	1.3661 (12)	C12—H12B	0.9900
N2—C14	1.3732 (13)	C13—H13A	0.9900
N2—C21	1.3831 (13)	C13—H13B	0.9900
N2—H2	0.8800	C14—C15	1.3956 (14)
N1—C1	1.3739 (13)	C14—C19	1.4190 (13)
N1—C8	1.3841 (13)	C15—C16	1.3865 (16)
N1—H1	0.8800	C15—H15	0.9500
C1—C2	1.3906 (14)	C16—C17	1.3951 (17)
C1—C6	1.4189 (13)	C16—H16	0.9500
C2—C3	1.3846 (15)	C17—C18	1.3682 (16)
C2—H2A	0.9500	C18—C19	1.4065 (14)
C3—C4	1.3952 (16)	C18—H18	0.9500
C3—H3	0.9500	C19—C20	1.4304 (14)
C4—C5	1.3717 (15)	C20—C21	1.3743 (13)
C5—C6	1.4076 (14)	C20—C26	1.4975 (14)
C5—H5	0.9500	C21—C22	1.4888 (14)
C6—C7	1.4293 (14)	C22—C23	1.5294 (17)
C7—C8	1.3708 (14)	C22—H22A	0.9900
C7—C13	1.4974 (14)	C22—H22B	0.9900
C8—C9	1.4914 (15)	C23—C24	1.5300 (17)
C9—C10	1.5291 (16)	C23—H23A	0.9900
C9—H9A	0.9900	C23—H23B	0.9900
C9—H9B	0.9900	C24—C25	1.5270 (17)
C10—C11	1.5292 (17)	C24—H24A	0.9900
C10—H10A	0.9900	C24—H24B	0.9900
C10—H10B	0.9900	C25—C26	1.5271 (16)
C11—C12	1.5270 (17)	C25—H25A	0.9900
C11—H11A	0.9900	C25—H25B	0.9900
C11—H11B	0.9900	C26—H26A	0.9900
C12—C13	1.5246 (15)	C26—H26B	0.9900
C14—N2—C21	109.34 (8)	C7—C13—H13B	108.3
C14—N2—H2	125.3	C12—C13—H13B	108.3
C21—N2—H2	125.3	H13A—C13—H13B	107.4
C1—N1—C8	109.32 (8)	N2—C14—C15	130.53 (10)
C1—N1—H1	125.3	N2—C14—C19	107.11 (9)
C8—N1—H1	125.3	C15—C14—C19	122.37 (9)
N1—C1—C2	130.48 (9)	C16—C15—C14	117.66 (10)
N1—C1—C6	107.00 (9)	C16—C15—H15	121.2
C2—C1—C6	122.51 (9)	C14—C15—H15	121.2
C3—C2—C1	117.61 (10)	C15—C16—C17	119.38 (10)
C3—C2—H2A	121.2	C15—C16—H16	120.3
C1—C2—H2A	121.2	C17—C16—H16	120.3
C2—C3—C4	119.54 (10)	F2—C17—C18	118.45 (11)
C2—C3—H3	120.2	F2—C17—C16	117.11 (10)
C4—C3—H3	120.2	C18—C17—C16	124.44 (10)
F1—C4—C5	118.24 (10)	C17—C18—C19	117.07 (10)
F1—C4—C3	117.37 (10)	C17—C18—H18	121.5
C5—C4—C3	124.39 (10)	C19—C18—H18	121.5
C4—C5—C6	116.74 (9)	C18—C19—C14	119.08 (9)
C4—C5—H5	121.6	C18—C19—C20	133.48 (9)
C6—C5—H5	121.6	C14—C19—C20	107.43 (8)
C5—C6—C1	119.20 (9)	C21—C20—C19	106.60 (9)
C5—C6—C7	133.34 (9)	C21—C20—C26	126.33 (9)
C1—C6—C7	107.44 (9)	C19—C20—C26	127.07 (9)
C8—C7—C6	106.74 (9)	C20—C21—N2	109.52 (9)
C8—C7—C13	127.17 (10)	C20—C21—C22	129.28 (9)
C6—C7—C13	126.01 (9)	N2—C21—C22	121.20 (9)
C7—C8—N1	109.49 (9)	C21—C22—C23	113.71 (9)
C7—C8—C9	129.84 (10)	C21—C22—H22A	108.8
N1—C8—C9	120.65 (9)	C23—C22—H22A	108.8
C8—C9—C10	114.46 (9)	C21—C22—H22B	108.8
C8—C9—H9A	108.6	C23—C22—H22B	108.8
C10—C9—H9A	108.6	H22A—C22—H22B	107.7
C8—C9—H9B	108.6	C22—C23—C24	114.94 (9)
C10—C9—H9B	108.6	C22—C23—H23A	108.5
H9A—C9—H9B	107.6	C24—C23—H23A	108.5
C9—C10—C11	114.92 (10)	C22—C23—H23B	108.5
C9—C10—H10A	108.5	C24—C23—H23B	108.5
C11—C10—H10A	108.5	H23A—C23—H23B	107.5
C9—C10—H10B	108.5	C25—C24—C23	116.95 (9)
C11—C10—H10B	108.5	C25—C24—H24A	108.1
H10A—C10—H10B	107.5	C23—C24—H24A	108.1
C12—C11—C10	116.12 (10)	C25—C24—H24B	108.1
C12—C11—H11A	108.3	C23—C24—H24B	108.1
C10—C11—H11A	108.3	H24A—C24—H24B	107.3
C12—C11—H11B	108.3	C24—C25—C26	115.81 (9)
C10—C11—H11B	108.3	C24—C25—H25A	108.3
H11A—C11—H11B	107.4	C26—C25—H25A	108.3
C13—C12—C11	115.57 (10)	C24—C25—H25B	108.3
C13—C12—H12A	108.4	C26—C25—H25B	108.3
C11—C12—H12A	108.4	H25A—C25—H25B	107.4
C13—C12—H12B	108.4	C20—C26—C25	114.44 (9)
C11—C12—H12B	108.4	C20—C26—H26A	108.7
H12A—C12—H12B	107.4	C25—C26—H26A	108.7
C7—C13—C12	116.04 (9)	C20—C26—H26B	108.7
C7—C13—H13A	108.3	C25—C26—H26B	108.7
C12—C13—H13A	108.3	H26A—C26—H26B	107.6
C8—N1—C1—C2	178.00 (10)	C21—N2—C14—C15	−179.57 (11)
C8—N1—C1—C6	−1.04 (11)	C21—N2—C14—C19	−0.16 (11)
N1—C1—C2—C3	−178.24 (10)	N2—C14—C15—C16	179.00 (10)
C6—C1—C2—C3	0.68 (15)	C19—C14—C15—C16	−0.34 (15)
C1—C2—C3—C4	−0.37 (16)	C14—C15—C16—C17	0.06 (15)
C2—C3—C4—F1	179.37 (9)	C15—C16—C17—F2	−179.68 (9)
C2—C3—C4—C5	−0.42 (17)	C15—C16—C17—C18	0.11 (17)
F1—C4—C5—C6	−178.92 (9)	F2—C17—C18—C19	179.78 (9)
C3—C4—C5—C6	0.87 (16)	C16—C17—C18—C19	0.00 (16)
C4—C5—C6—C1	−0.54 (14)	C17—C18—C19—C14	−0.26 (15)
C4—C5—C6—C7	177.33 (10)	C17—C18—C19—C20	−179.46 (11)
N1—C1—C6—C5	178.92 (9)	N2—C14—C19—C18	−179.03 (9)
C2—C1—C6—C5	−0.21 (15)	C15—C14—C19—C18	0.45 (15)
N1—C1—C6—C7	0.55 (11)	N2—C14—C19—C20	0.36 (11)
C2—C1—C6—C7	−178.59 (9)	C15—C14—C19—C20	179.83 (9)
C5—C6—C7—C8	−177.90 (11)	C18—C19—C20—C21	178.83 (11)
C1—C6—C7—C8	0.15 (11)	C14—C19—C20—C21	−0.43 (11)
C5—C6—C7—C13	5.15 (18)	C18—C19—C20—C26	−0.99 (18)
C1—C6—C7—C13	−176.80 (10)	C14—C19—C20—C26	179.75 (9)
C6—C7—C8—N1	−0.79 (11)	C19—C20—C21—N2	0.34 (11)
C13—C7—C8—N1	176.12 (10)	C26—C20—C21—N2	−179.84 (9)
C6—C7—C8—C9	−179.32 (10)	C19—C20—C21—C22	−178.98 (10)
C13—C7—C8—C9	−2.42 (18)	C26—C20—C21—C22	0.84 (18)
C1—N1—C8—C7	1.16 (12)	C14—N2—C21—C20	−0.12 (12)
C1—N1—C8—C9	179.85 (9)	C14—N2—C21—C22	179.26 (9)
C7—C8—C9—C10	−46.68 (16)	C20—C21—C22—C23	−52.53 (15)
N1—C8—C9—C10	134.93 (10)	N2—C21—C22—C23	128.23 (10)
C8—C9—C10—C11	68.26 (13)	C21—C22—C23—C24	69.14 (13)
C9—C10—C11—C12	−72.52 (13)	C22—C23—C24—C25	−69.01 (14)
C10—C11—C12—C13	70.16 (14)	C23—C24—C25—C26	68.96 (14)
C8—C7—C13—C12	48.99 (16)	C21—C20—C26—C25	51.13 (14)
C6—C7—C13—C12	−134.68 (11)	C19—C20—C26—C25	−129.08 (11)
C11—C12—C13—C7	−66.18 (14)	C24—C25—C26—C20	−69.14 (12)

(HxBR3)

Crystal data

C12H12BrN	F(000) = 1008
Mr = 250.14	Dx = 1.624 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5845 reflections
a = 10.1791 (18) Å	θ = 2.7–29.7°
b = 8.7625 (15) Å	µ = 3.97 mm^−1
c = 22.946 (4) Å	T = 100 K
V = 2046.7 (6) Å^3	PLATE, colourless
Z = 8	0.43 × 0.28 × 0.15 mm

Data collection

Bruker APEX-II CCD diffractometer	3171 independent reflections
Radiation source: fine-focus sealed tube	1976 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.111
φ and ω scans	θmax = 30.8°, θmin = 2.7°
Absorption correction: multi-scan SADABS	h = −14→12
Tmin = 0.280, Tmax = 0.587	k = −12→12
22551 measured reflections	l = −32→32

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0682P)^2] where P = (Fo^2 + 2Fc^2)/3
3171 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.76 e Å^−3
0 restraints	Δρmin = −0.80 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br1	0.40172 (4)	0.07303 (4)	0.434652 (14)	0.02765 (14)
N1	0.5028 (3)	−0.0033 (3)	0.20763 (11)	0.0194 (5)
H1	0.5676	−0.0697	0.2084	0.023*
C1	0.4409 (3)	0.0575 (3)	0.25565 (14)	0.0176 (6)
C2	0.4613 (3)	0.0318 (3)	0.31469 (14)	0.0200 (6)
H2	0.5285	−0.0351	0.3279	0.024*
C3	0.3805 (3)	0.1071 (3)	0.35342 (14)	0.0192 (6)
C4	0.2802 (3)	0.2068 (3)	0.33488 (14)	0.0201 (6)
H4	0.2269	0.2578	0.3627	0.024*
C5	0.2597 (3)	0.2301 (4)	0.27601 (13)	0.0194 (6)
H5	0.1912	0.2957	0.2633	0.023*
C6	0.3405 (3)	0.1564 (3)	0.23509 (13)	0.0163 (6)
C7	0.3462 (3)	0.1542 (3)	0.17284 (13)	0.0184 (6)
C8	0.4462 (3)	0.0576 (3)	0.15769 (14)	0.0196 (7)
C9	0.4895 (4)	0.0220 (4)	0.09732 (14)	0.0246 (7)
H9A	0.4590	−0.0812	0.0861	0.030*
H9B	0.5866	0.0239	0.0951	0.030*
C10	0.4312 (4)	0.1419 (4)	0.05575 (15)	0.0339 (9)
H10A	0.4797	0.2391	0.0603	0.041*
H10B	0.4425	0.1070	0.0150	0.041*
C11	0.2859 (4)	0.1691 (4)	0.06765 (14)	0.0316 (8)
H11A	0.2377	0.0715	0.0637	0.038*
H11B	0.2506	0.2409	0.0382	0.038*
C12	0.2624 (3)	0.2348 (4)	0.12895 (14)	0.0232 (7)
H12A	0.2834	0.3451	0.1291	0.028*
H12B	0.1686	0.2229	0.1395	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0345 (2)	0.0297 (2)	0.0187 (2)	0.00086 (15)	−0.00122 (13)	−0.00172 (13)
N1	0.0179 (13)	0.0178 (13)	0.0225 (14)	0.0052 (10)	−0.0006 (11)	−0.0014 (10)
C1	0.0140 (14)	0.0143 (15)	0.0244 (17)	−0.0029 (11)	−0.0001 (12)	−0.0022 (12)
C2	0.0173 (15)	0.0179 (15)	0.0249 (17)	0.0003 (12)	−0.0025 (13)	−0.0007 (12)
C3	0.0215 (16)	0.0181 (15)	0.0180 (15)	−0.0045 (12)	0.0005 (12)	−0.0030 (12)
C4	0.0171 (15)	0.0182 (15)	0.0249 (16)	−0.0011 (12)	0.0028 (13)	−0.0037 (13)
C5	0.0163 (15)	0.0163 (15)	0.0255 (16)	0.0027 (12)	0.0018 (12)	0.0014 (12)
C6	0.0128 (14)	0.0124 (14)	0.0238 (15)	−0.0022 (11)	−0.0002 (12)	0.0000 (12)
C7	0.0168 (15)	0.0157 (15)	0.0226 (16)	−0.0016 (12)	0.0004 (13)	0.0004 (12)
C8	0.0223 (15)	0.0160 (16)	0.0206 (16)	−0.0044 (12)	−0.0006 (13)	−0.0020 (11)
C9	0.0307 (19)	0.0214 (16)	0.0217 (17)	−0.0006 (14)	0.0049 (15)	−0.0001 (13)
C10	0.049 (2)	0.0243 (19)	0.028 (2)	0.0052 (17)	0.0089 (16)	0.0038 (15)
C11	0.035 (2)	0.033 (2)	0.0271 (19)	0.0036 (16)	−0.0021 (15)	0.0069 (14)
C12	0.0234 (16)	0.0198 (16)	0.0263 (17)	0.0007 (13)	−0.0018 (13)	0.0050 (13)

Geometric parameters (Å, º)

Br1—C3	1.900 (3)	C7—C8	1.369 (4)
N1—C1	1.376 (4)	C7—C12	1.497 (4)
N1—C8	1.389 (4)	C8—C9	1.487 (4)
N1—H1	0.8800	C9—C10	1.538 (5)
C1—C2	1.389 (4)	C9—H9A	0.9900
C1—C6	1.421 (4)	C9—H9B	0.9900
C2—C3	1.379 (4)	C10—C11	1.523 (5)
C2—H2	0.9500	C10—H10A	0.9900
C3—C4	1.409 (4)	C10—H10B	0.9900
C4—C5	1.382 (4)	C11—C12	1.539 (5)
C4—H4	0.9500	C11—H11A	0.9900
C5—C6	1.405 (4)	C11—H11B	0.9900
C5—H5	0.9500	C12—H12A	0.9900
C6—C7	1.430 (4)	C12—H12B	0.9900
C1—N1—C8	108.8 (3)	N1—C8—C9	124.4 (3)
C1—N1—H1	125.6	C8—C9—C10	108.7 (3)
C8—N1—H1	125.6	C8—C9—H9A	109.9
N1—C1—C2	130.5 (3)	C10—C9—H9A	109.9
N1—C1—C6	107.4 (3)	C8—C9—H9B	109.9
C2—C1—C6	122.0 (3)	C10—C9—H9B	109.9
C3—C2—C1	117.5 (3)	H9A—C9—H9B	108.3
C3—C2—H2	121.2	C11—C10—C9	111.7 (3)
C1—C2—H2	121.2	C11—C10—H10A	109.3
C2—C3—C4	122.3 (3)	C9—C10—H10A	109.3
C2—C3—Br1	119.3 (2)	C11—C10—H10B	109.3
C4—C3—Br1	118.4 (2)	C9—C10—H10B	109.3
C5—C4—C3	119.7 (3)	H10A—C10—H10B	107.9
C5—C4—H4	120.1	C10—C11—C12	112.0 (3)
C3—C4—H4	120.1	C10—C11—H11A	109.2
C4—C5—C6	119.8 (3)	C12—C11—H11A	109.2
C4—C5—H5	120.1	C10—C11—H11B	109.2
C6—C5—H5	120.1	C12—C11—H11B	109.2
C5—C6—C1	118.6 (3)	H11A—C11—H11B	107.9
C5—C6—C7	134.2 (3)	C7—C12—C11	110.5 (3)
C1—C6—C7	107.1 (3)	C7—C12—H12A	109.6
C8—C7—C6	107.0 (3)	C11—C12—H12A	109.6
C8—C7—C12	123.0 (3)	C7—C12—H12B	109.6
C6—C7—C12	130.0 (3)	C11—C12—H12B	109.6
C7—C8—N1	109.7 (3)	H12A—C12—H12B	108.1
C7—C8—C9	125.9 (3)
C8—N1—C1—C2	179.5 (3)	C1—C6—C7—C8	0.0 (3)
C8—N1—C1—C6	1.4 (3)	C5—C6—C7—C12	−0.1 (6)
N1—C1—C2—C3	−178.2 (3)	C1—C6—C7—C12	178.9 (3)
C6—C1—C2—C3	−0.4 (4)	C6—C7—C8—N1	0.9 (3)
C1—C2—C3—C4	0.0 (4)	C12—C7—C8—N1	−178.1 (3)
C1—C2—C3—Br1	178.8 (2)	C6—C7—C8—C9	−178.9 (3)
C2—C3—C4—C5	0.8 (5)	C12—C7—C8—C9	2.1 (5)
Br1—C3—C4—C5	−178.0 (2)	C1—N1—C8—C7	−1.5 (3)
C3—C4—C5—C6	−1.2 (4)	C1—N1—C8—C9	178.3 (3)
C4—C5—C6—C1	0.8 (4)	C7—C8—C9—C10	15.3 (5)
C4—C5—C6—C7	179.6 (3)	N1—C8—C9—C10	−164.4 (3)
N1—C1—C6—C5	178.2 (3)	C8—C9—C10—C11	−46.4 (4)
C2—C1—C6—C5	0.0 (4)	C9—C10—C11—C12	63.1 (4)
N1—C1—C6—C7	−0.9 (3)	C8—C7—C12—C11	11.5 (4)
C2—C1—C6—C7	−179.1 (3)	C6—C7—C12—C11	−167.2 (3)
C5—C6—C7—C8	−178.9 (3)	C10—C11—C12—C7	−42.8 (4)

(HxBR4)

Crystal data

C12H12BrN	F(000) = 1008
Mr = 250.14	Dx = 1.642 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9171 reflections
a = 24.4539 (18) Å	θ = 2.5–30.5°
b = 6.1680 (4) Å	µ = 4.02 mm^−1
c = 16.2352 (12) Å	T = 100 K
β = 124.277 (2)°	Plate, pale yellow
V = 2023.5 (2) Å^3	0.43 × 0.28 × 0.15 mm
Z = 8

Data collection

Bruker APEX-II CCD diffractometer	3082 independent reflections
Radiation source: fine-focus sealed tube	2685 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
φ and ω scans	θmax = 30.5°, θmin = 3.0°
Absorption correction: multi-scan SADABS	h = −34→34
Tmin = 0.277, Tmax = 0.584	k = −8→6
16811 measured reflections	l = −23→23

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.071	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0357P)^2 + 1.4692P] where P = (Fo^2 + 2Fc^2)/3
3082 reflections	(Δ/σ)max = 0.001
146 parameters	Δρmax = 0.40 e Å^−3
3 restraints	Δρmin = −0.52 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
Br1	0.458794 (7)	0.33392 (3)	0.851043 (12)	0.02169 (7)
N1	0.22329 (6)	0.9268 (2)	0.64286 (9)	0.0163 (2)
H1	0.2140	1.0542	0.6565	0.020*
C1	0.28211 (8)	0.8162 (2)	0.70214 (11)	0.0145 (3)
C2	0.33916 (8)	0.8707 (2)	0.79429 (12)	0.0168 (3)
H2	0.3421	1.0031	0.8265	0.020*
C3	0.39171 (8)	0.7249 (3)	0.83755 (11)	0.0173 (3)
H3	0.4314	0.7571	0.9001	0.021*
C4	0.38598 (7)	0.5301 (2)	0.78858 (11)	0.0159 (3)
C5	0.33000 (7)	0.4744 (2)	0.69737 (11)	0.0161 (3)
H5	0.3276	0.3413	0.6661	0.019*
C6	0.27680 (8)	0.6199 (2)	0.65220 (11)	0.0139 (3)
C7	0.21225 (8)	0.6181 (2)	0.56098 (11)	0.0143 (3)
C8	0.18114 (8)	0.8045 (2)	0.55842 (11)	0.0143 (3)
C9	0.11144 (8)	0.8648 (2)	0.47915 (12)	0.0184 (3)
H9A	0.1109	0.9698	0.4326	0.022*
H9B	0.0903	0.9337	0.5096	0.022*
C10A	0.07346 (14)	0.6614 (5)	0.4229 (2)	0.0178 (8)	0.582 (7)
H10A	0.0297	0.7024	0.3632	0.021*	0.582 (7)
H10B	0.0661	0.5705	0.4661	0.021*	0.582 (7)
C11A	0.11230 (14)	0.5319 (6)	0.3912 (2)	0.0175 (7)	0.582 (7)
H11A	0.1196	0.6245	0.3485	0.021*	0.582 (7)
H11B	0.0855	0.4057	0.3510	0.021*	0.582 (7)
C10B	0.0845 (2)	0.7063 (7)	0.3894 (3)	0.0191 (11)	0.418 (7)
H10C	0.0356	0.7156	0.3470	0.023*	0.418 (7)
H10D	0.1010	0.7532	0.3488	0.023*	0.418 (7)
C11B	0.10460 (19)	0.4714 (7)	0.4206 (4)	0.0180 (10)	0.418 (7)
H11C	0.0842	0.3781	0.3607	0.022*	0.418 (7)
H11D	0.0886	0.4226	0.4616	0.022*	0.418 (7)
C12	0.17991 (8)	0.4504 (2)	0.48060 (11)	0.0178 (3)
H12A	0.1734	0.3158	0.5074	0.021*
H12B	0.2090	0.4162	0.4580	0.021*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.01260 (9)	0.02340 (10)	0.02086 (10)	0.00196 (5)	0.00445 (7)	−0.00300 (6)
N1	0.0175 (6)	0.0140 (5)	0.0153 (6)	0.0005 (5)	0.0079 (5)	−0.0028 (5)
C1	0.0151 (7)	0.0151 (6)	0.0147 (7)	−0.0007 (5)	0.0093 (6)	−0.0010 (5)
C2	0.0182 (8)	0.0172 (6)	0.0159 (7)	−0.0032 (5)	0.0101 (6)	−0.0045 (5)
C3	0.0158 (7)	0.0209 (7)	0.0135 (7)	−0.0037 (6)	0.0072 (6)	−0.0035 (5)
C4	0.0126 (7)	0.0180 (7)	0.0165 (7)	0.0008 (5)	0.0077 (6)	−0.0003 (5)
C5	0.0161 (7)	0.0155 (6)	0.0164 (7)	−0.0019 (5)	0.0091 (6)	−0.0035 (5)
C6	0.0147 (7)	0.0151 (6)	0.0130 (6)	−0.0021 (5)	0.0083 (6)	−0.0020 (5)
C7	0.0141 (7)	0.0155 (6)	0.0131 (6)	−0.0016 (5)	0.0076 (6)	−0.0016 (5)
C8	0.0143 (7)	0.0152 (6)	0.0129 (6)	−0.0015 (5)	0.0073 (6)	−0.0007 (5)
C9	0.0157 (7)	0.0184 (7)	0.0170 (7)	0.0024 (5)	0.0068 (6)	−0.0002 (5)
C10A	0.0127 (13)	0.0216 (14)	0.0163 (14)	−0.0008 (10)	0.0065 (11)	−0.0014 (10)
C11A	0.0165 (13)	0.0193 (14)	0.0116 (13)	−0.0028 (10)	0.0050 (11)	−0.0043 (10)
C10B	0.0143 (18)	0.0242 (19)	0.0123 (18)	−0.0009 (14)	0.0035 (15)	0.0008 (14)
C11B	0.0140 (18)	0.0194 (19)	0.015 (2)	−0.0045 (14)	0.0049 (15)	−0.0047 (16)
C12	0.0160 (7)	0.0169 (7)	0.0153 (7)	−0.0006 (5)	0.0057 (6)	−0.0034 (5)

Geometric parameters (Å, º)

Br1—C4	1.9051 (15)	C9—C10B	1.559 (4)
N1—C1	1.379 (2)	C9—H9A	0.9900
N1—C8	1.3852 (19)	C9—H9B	0.9900
N1—H1	0.8800	C10A—C11A	1.535 (4)
C1—C2	1.395 (2)	C10A—H10A	0.9900
C1—C6	1.4220 (19)	C10A—H10B	0.9900
C2—C3	1.392 (2)	C11A—C12	1.546 (3)
C2—H2	0.9500	C11A—H11A	0.9900
C3—C4	1.403 (2)	C11A—H11B	0.9900
C3—H3	0.9500	C10B—C11B	1.522 (6)
C4—C5	1.379 (2)	C10B—H10C	0.9900
C5—C6	1.400 (2)	C10B—H10D	0.9900
C5—H5	0.9500	C11B—C12	1.529 (4)
C6—C7	1.432 (2)	C11B—H11C	0.9900
C7—C8	1.367 (2)	C11B—H11D	0.9900
C7—C12	1.495 (2)	C12—H12A	0.9900
C8—C9	1.493 (2)	C12—H12B	0.9900
C9—C10A	1.521 (3)
C1—N1—C8	108.90 (12)	H9A—C9—H9B	108.3
C1—N1—H1	125.6	C9—C10A—C11A	110.3 (3)
C8—N1—H1	125.6	C9—C10A—H10A	109.6
N1—C1—C2	130.49 (13)	C11A—C10A—H10A	109.6
N1—C1—C6	107.39 (13)	C9—C10A—H10B	109.6
C2—C1—C6	122.12 (14)	C11A—C10A—H10B	109.6
C3—C2—C1	117.82 (14)	H10A—C10A—H10B	108.1
C3—C2—H2	121.1	C10A—C11A—C12	113.0 (3)
C1—C2—H2	121.1	C10A—C11A—H11A	109.0
C2—C3—C4	119.88 (14)	C12—C11A—H11A	109.0
C2—C3—H3	120.1	C10A—C11A—H11B	109.0
C4—C3—H3	120.1	C12—C11A—H11B	109.0
C5—C4—C3	122.92 (14)	H11A—C11A—H11B	107.8
C5—C4—Br1	118.59 (11)	C11B—C10B—C9	113.5 (4)
C3—C4—Br1	118.49 (11)	C11B—C10B—H10C	108.9
C4—C5—C6	118.07 (13)	C9—C10B—H10C	108.9
C4—C5—H5	121.0	C11B—C10B—H10D	108.9
C6—C5—H5	121.0	C9—C10B—H10D	108.9
C5—C6—C1	119.17 (14)	H10C—C10B—H10D	107.7
C5—C6—C7	133.98 (13)	C10B—C11B—C12	109.9 (4)
C1—C6—C7	106.84 (13)	C10B—C11B—H11C	109.7
C8—C7—C6	107.18 (13)	C12—C11B—H11C	109.7
C8—C7—C12	122.94 (14)	C10B—C11B—H11D	109.7
C6—C7—C12	129.87 (13)	C12—C11B—H11D	109.7
C7—C8—N1	109.68 (13)	H11C—C11B—H11D	108.2
C7—C8—C9	125.55 (14)	C7—C12—C11B	110.66 (18)
N1—C8—C9	124.73 (13)	C7—C12—C11A	110.79 (15)
C8—C9—C10A	109.09 (15)	C7—C12—H12A	109.5
C8—C9—C10B	109.02 (19)	C11B—C12—H12A	85.3
C8—C9—H9A	109.9	C11A—C12—H12A	109.5
C10A—C9—H9A	109.9	C7—C12—H12B	109.5
C10B—C9—H9A	83.1	C11B—C12—H12B	129.9
C8—C9—H9B	109.9	C11A—C12—H12B	109.5
C10A—C9—H9B	109.9	H12A—C12—H12B	108.1
C10B—C9—H9B	132.2
C8—N1—C1—C2	−179.31 (16)	C12—C7—C8—C9	2.1 (2)
C8—N1—C1—C6	0.91 (16)	C1—N1—C8—C7	−1.27 (17)
N1—C1—C2—C3	179.76 (15)	C1—N1—C8—C9	176.47 (14)
C6—C1—C2—C3	−0.5 (2)	C7—C8—C9—C10A	19.6 (3)
C1—C2—C3—C4	−0.3 (2)	N1—C8—C9—C10A	−157.8 (2)
C2—C3—C4—C5	0.5 (2)	C7—C8—C9—C10B	−11.5 (3)
C2—C3—C4—Br1	−179.43 (12)	N1—C8—C9—C10B	171.1 (3)
C3—C4—C5—C6	0.0 (2)	C8—C9—C10A—C11A	−49.5 (3)
Br1—C4—C5—C6	179.98 (11)	C10B—C9—C10A—C11A	45.5 (4)
C4—C5—C6—C1	−0.8 (2)	C9—C10A—C11A—C12	62.4 (4)
C4—C5—C6—C7	−179.34 (16)	C8—C9—C10B—C11B	41.3 (5)
N1—C1—C6—C5	−179.16 (13)	C10A—C9—C10B—C11B	−54.0 (4)
C2—C1—C6—C5	1.0 (2)	C9—C10B—C11B—C12	−62.3 (6)
N1—C1—C6—C7	−0.25 (16)	C8—C7—C12—C11B	−21.1 (3)
C2—C1—C6—C7	179.96 (14)	C6—C7—C12—C11B	157.3 (3)
C5—C6—C7—C8	178.17 (16)	C8—C7—C12—C11A	7.5 (3)
C1—C6—C7—C8	−0.51 (16)	C6—C7—C12—C11A	−174.1 (2)
C5—C6—C7—C12	−0.4 (3)	C10B—C11B—C12—C7	49.2 (5)
C1—C6—C7—C12	−179.09 (15)	C10B—C11B—C12—C11A	−46.2 (4)
C6—C7—C8—N1	1.09 (17)	C10A—C11A—C12—C7	−39.0 (4)
C12—C7—C8—N1	179.79 (14)	C10A—C11A—C12—C11B	55.9 (4)
C6—C7—C8—C9	−176.62 (14)

(HXCL2)

Crystal data

C12H12ClN	F(000) = 864
Mr = 205.68	Dx = 1.365 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7337 reflections
a = 10.8001 (9) Å	θ = 2.7–30.4°
b = 8.8083 (7) Å	µ = 0.34 mm^−1
c = 21.0408 (17) Å	T = 100 K
V = 2001.6 (3) Å^3	PLATE, colourless
Z = 8	0.38 × 0.33 × 0.15 mm

Data collection

Bruker APEX-II CCD diffractometer	3058 independent reflections
Radiation source: fine-focus sealed tube	2457 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
φ and ω scans	θmax = 30.6°, θmin = 2.7°
Absorption correction: multi-scan SADABS	h = −15→15
Tmin = 0.883, Tmax = 0.951	k = −12→12
17748 measured reflections	l = −30→25

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0549P)^2 + 0.799P] where P = (Fo^2 + 2Fc^2)/3
3058 reflections	(Δ/σ)max = 0.001
128 parameters	Δρmax = 0.48 e Å^−3
3 restraints	Δρmin = −0.35 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
Cl1	0.53903 (3)	0.27846 (4)	−0.099488 (15)	0.02341 (11)
N1	0.50731 (11)	0.27876 (12)	0.04963 (5)	0.0176 (2)
H1	0.5652	0.3423	0.0370	0.021*
C1	0.43544 (12)	0.19005 (14)	0.01101 (6)	0.0158 (2)
C2	0.43497 (12)	0.17349 (14)	−0.05465 (6)	0.0172 (2)
C3	0.35264 (13)	0.07467 (15)	−0.08275 (6)	0.0204 (3)
H3	0.3518	0.0630	−0.1276	0.024*
C4	0.26995 (13)	−0.00876 (15)	−0.04497 (7)	0.0225 (3)
H4	0.2137	−0.0769	−0.0648	0.027*
C5	0.26854 (13)	0.00620 (14)	0.02078 (6)	0.0208 (3)
H5	0.2120	−0.0509	0.0458	0.025*
C6	0.35175 (12)	0.10671 (13)	0.04941 (6)	0.0168 (2)
C7	0.37829 (12)	0.14969 (14)	0.11396 (6)	0.0176 (2)
C8	0.47334 (13)	0.25134 (15)	0.11199 (6)	0.0183 (3)
C9	0.53643 (14)	0.32084 (17)	0.16798 (6)	0.0259 (3)
H9A	0.5096	0.4276	0.1731	0.031*
H9B	0.6273	0.3195	0.1617	0.031*
C10A	0.50207 (18)	0.2288 (2)	0.22745 (7)	0.0287 (3)	0.915 (3)
H10A	0.5481	0.1316	0.2272	0.034*	0.915 (3)
H10B	0.5270	0.2861	0.2659	0.034*	0.915 (3)
C11A	0.36387 (18)	0.1963 (2)	0.23031 (7)	0.0287 (3)	0.915 (3)
H11A	0.3177	0.2934	0.2289	0.034*	0.915 (3)
H11B	0.3441	0.1454	0.2710	0.034*	0.915 (3)
C10B	0.4534 (18)	0.2970 (19)	0.2266 (7)	0.0287 (3)	0.085 (3)
H10C	0.5009	0.3209	0.2655	0.034*	0.085 (3)
H10D	0.3819	0.3673	0.2244	0.034*	0.085 (3)
C11B	0.4076 (19)	0.1380 (19)	0.2300 (7)	0.0287 (3)	0.085 (3)
H11C	0.3625	0.1238	0.2705	0.034*	0.085 (3)
H11D	0.4795	0.0683	0.2302	0.034*	0.085 (3)
C12	0.32209 (13)	0.09504 (16)	0.17487 (6)	0.0226 (3)
H12A	0.3479	−0.0111	0.1829	0.027*
H12B	0.2307	0.0973	0.1715	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.02540 (19)	0.02865 (19)	0.01618 (16)	−0.00357 (12)	0.00201 (11)	0.00301 (12)
N1	0.0185 (5)	0.0199 (5)	0.0145 (5)	−0.0034 (4)	−0.0013 (4)	0.0009 (4)
C1	0.0146 (6)	0.0156 (5)	0.0172 (6)	0.0024 (4)	−0.0005 (4)	0.0001 (4)
C2	0.0177 (6)	0.0179 (5)	0.0160 (5)	0.0036 (5)	0.0005 (4)	0.0014 (4)
C3	0.0212 (6)	0.0207 (6)	0.0193 (6)	0.0045 (5)	−0.0039 (5)	−0.0030 (5)
C4	0.0192 (7)	0.0200 (6)	0.0282 (7)	0.0000 (5)	−0.0040 (5)	−0.0038 (5)
C5	0.0175 (7)	0.0181 (5)	0.0267 (7)	−0.0008 (5)	0.0013 (5)	0.0006 (5)
C6	0.0151 (6)	0.0163 (5)	0.0191 (6)	0.0034 (4)	0.0007 (4)	0.0012 (4)
C7	0.0179 (6)	0.0187 (6)	0.0162 (5)	0.0039 (5)	0.0006 (5)	0.0021 (4)
C8	0.0200 (6)	0.0201 (6)	0.0149 (6)	0.0028 (5)	−0.0009 (5)	0.0010 (4)
C9	0.0304 (8)	0.0308 (7)	0.0163 (6)	−0.0044 (6)	−0.0040 (5)	0.0004 (5)
C10A	0.0342 (7)	0.0363 (7)	0.0155 (5)	0.0012 (5)	−0.0004 (4)	0.0038 (4)
C11A	0.0342 (7)	0.0363 (7)	0.0155 (5)	0.0012 (5)	−0.0004 (4)	0.0038 (4)
C10B	0.0342 (7)	0.0363 (7)	0.0155 (5)	0.0012 (5)	−0.0004 (4)	0.0038 (4)
C11B	0.0342 (7)	0.0363 (7)	0.0155 (5)	0.0012 (5)	−0.0004 (4)	0.0038 (4)
C12	0.0219 (7)	0.0269 (6)	0.0190 (6)	0.0024 (5)	0.0018 (5)	0.0060 (5)

Geometric parameters (Å, º)

Cl1—C2	1.7344 (13)	C9—C10B	1.539 (13)
N1—C1	1.3687 (16)	C9—H9A	0.9900
N1—C8	1.3837 (17)	C9—H9B	0.9900
N1—H1	0.8800	C10A—C11A	1.521 (3)
C1—C2	1.3891 (17)	C10A—H10A	0.9900
C1—C6	1.4173 (18)	C10A—H10B	0.9900
C2—C3	1.3777 (18)	C11A—C12	1.536 (2)
C3—C4	1.404 (2)	C11A—H11A	0.9900
C3—H3	0.9500	C11A—H11B	0.9900
C4—C5	1.3896 (19)	C10B—C11B	1.488 (17)
C4—H4	0.9500	C10B—H10C	0.9900
C5—C6	1.3980 (18)	C10B—H10D	0.9900
C5—H5	0.9500	C11B—C12	1.530 (13)
C6—C7	1.4390 (17)	C11B—H11C	0.9900
C7—C8	1.3628 (19)	C11B—H11D	0.9900
C7—C12	1.4975 (17)	C12—H12A	0.9900
C8—C9	1.4923 (19)	C12—H12B	0.9900
C9—C10A	1.536 (2)
C1—N1—C8	108.24 (11)	H9A—C9—H9B	108.4
C1—N1—H1	125.9	C11A—C10A—C9	111.63 (14)
C8—N1—H1	125.9	C11A—C10A—H10A	109.3
N1—C1—C2	130.73 (12)	C9—C10A—H10A	109.3
N1—C1—C6	108.59 (11)	C11A—C10A—H10B	109.3
C2—C1—C6	120.67 (12)	C9—C10A—H10B	109.3
C3—C2—C1	119.71 (12)	H10A—C10A—H10B	108.0
C3—C2—Cl1	121.43 (10)	C10A—C11A—C12	111.55 (14)
C1—C2—Cl1	118.86 (10)	C10A—C11A—H11A	109.3
C2—C3—C4	119.89 (12)	C12—C11A—H11A	109.3
C2—C3—H3	120.1	C10A—C11A—H11B	109.3
C4—C3—H3	120.1	C12—C11A—H11B	109.3
C5—C4—C3	121.41 (12)	H11A—C11A—H11B	108.0
C5—C4—H4	119.3	C11B—C10B—C9	111.1 (13)
C3—C4—H4	119.3	C11B—C10B—H10C	109.4
C4—C5—C6	118.81 (12)	C9—C10B—H10C	109.4
C4—C5—H5	120.6	C11B—C10B—H10D	109.4
C6—C5—H5	120.6	C9—C10B—H10D	109.4
C5—C6—C1	119.50 (12)	H10C—C10B—H10D	108.0
C5—C6—C7	134.54 (12)	C10B—C11B—C12	113.4 (13)
C1—C6—C7	105.95 (11)	C10B—C11B—H11C	108.9
C8—C7—C6	107.11 (11)	C12—C11B—H11C	108.9
C8—C7—C12	122.86 (12)	C10B—C11B—H11D	108.9
C6—C7—C12	129.98 (12)	C12—C11B—H11D	108.9
C7—C8—N1	110.08 (11)	H11C—C11B—H11D	107.7
C7—C8—C9	126.12 (12)	C7—C12—C11B	108.9 (7)
N1—C8—C9	123.78 (12)	C7—C12—C11A	110.12 (12)
C8—C9—C10A	108.44 (12)	C7—C12—H12A	109.6
C8—C9—C10B	108.1 (7)	C11B—C12—H12A	86.2
C8—C9—H9A	110.0	C11A—C12—H12A	109.6
C10A—C9—H9A	110.0	C7—C12—H12B	109.6
C10B—C9—H9A	82.6	C11B—C12—H12B	130.7
C8—C9—H9B	110.0	C11A—C12—H12B	109.6
C10A—C9—H9B	110.0	H12A—C12—H12B	108.1
C10B—C9—H9B	133.1
C8—N1—C1—C2	−178.52 (13)	C6—C7—C8—C9	−176.60 (13)
C8—N1—C1—C6	1.37 (14)	C12—C7—C8—C9	1.0 (2)
N1—C1—C2—C3	179.65 (13)	C1—N1—C8—C7	−1.77 (15)
C6—C1—C2—C3	−0.23 (18)	C1—N1—C8—C9	176.32 (12)
N1—C1—C2—Cl1	−0.28 (19)	C7—C8—C9—C10A	15.1 (2)
C6—C1—C2—Cl1	179.84 (9)	N1—C8—C9—C10A	−162.64 (13)
C1—C2—C3—C4	−0.09 (18)	C7—C8—C9—C10B	−16.6 (8)
Cl1—C2—C3—C4	179.83 (10)	N1—C8—C9—C10B	165.6 (8)
C2—C3—C4—C5	0.2 (2)	C8—C9—C10A—C11A	−46.19 (18)
C3—C4—C5—C6	−0.06 (19)	C10B—C9—C10A—C11A	48.2 (13)
C4—C5—C6—C1	−0.26 (18)	C9—C10A—C11A—C12	64.19 (19)
C4—C5—C6—C7	−178.91 (14)	C8—C9—C10B—C11B	46.4 (16)
N1—C1—C6—C5	−179.49 (11)	C10A—C9—C10B—C11B	−49.4 (12)
C2—C1—C6—C5	0.41 (18)	C9—C10B—C11B—C12	−65 (2)
N1—C1—C6—C7	−0.49 (13)	C8—C7—C12—C11B	−14.3 (8)
C2—C1—C6—C7	179.41 (11)	C6—C7—C12—C11B	162.8 (8)
C5—C6—C7—C8	178.21 (14)	C8—C7—C12—C11A	13.69 (19)
C1—C6—C7—C8	−0.57 (14)	C6—C7—C12—C11A	−169.30 (14)
C5—C6—C7—C12	0.8 (2)	C10B—C11B—C12—C7	45.6 (18)
C1—C6—C7—C12	−177.95 (13)	C10B—C11B—C12—C11A	−51.7 (13)
C6—C7—C8—N1	1.43 (15)	C10A—C11A—C12—C7	−44.90 (18)
C12—C7—C8—N1	179.04 (12)	C10A—C11A—C12—C11B	47.3 (14)

(HxCL3)

Crystal data

C12H12ClN	F(000) = 216
Mr = 205.68	Dx = 1.364 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3038 reflections
a = 5.7132 (12) Å	θ = 3.1–29.7°
b = 8.1116 (18) Å	µ = 0.34 mm^−1
c = 10.878 (2) Å	T = 100 K
β = 96.698 (8)°	PLATE, colourless
V = 500.67 (19) Å^3	0.41 × 0.33 × 0.16 mm
Z = 2

Data collection

Bruker APEX-II CCD diffractometer	1681 independent reflections
Radiation source: fine-focus sealed tube	1561 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan SADABS	h = −6→6
Tmin = 0.874, Tmax = 0.948	k = −9→9
4608 measured reflections	l = −12→12

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)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.078	w = 1/[σ^2(Fo^2) + (0.0328P)^2 + 0.0977P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
1681 reflections	Δρmax = 0.20 e Å^−3
146 parameters	Δρmin = −0.17 e Å^−3
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (7)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
Cl1	−0.03758 (11)	0.33390 (8)	0.12641 (5)	0.0408 (2)
N1	0.0569 (3)	0.2574 (2)	0.60331 (17)	0.0256 (5)
H1	−0.0623	0.1923	0.6142	0.031*
C1	0.1107 (4)	0.3157 (3)	0.49158 (19)	0.0212 (5)
C2	−0.0046 (4)	0.2901 (3)	0.3726 (2)	0.0238 (5)
H2	−0.1440	0.2257	0.3581	0.029*
C3	0.0959 (4)	0.3638 (3)	0.2780 (2)	0.0261 (6)
C4	0.3005 (4)	0.4595 (3)	0.2961 (2)	0.0264 (5)
H4	0.3629	0.5074	0.2271	0.032*
C5	0.4113 (4)	0.4842 (3)	0.4136 (2)	0.0252 (5)
H5	0.5508	0.5487	0.4264	0.030*
C6	0.3165 (4)	0.4133 (3)	0.5145 (2)	0.0210 (5)
C7	0.3818 (4)	0.4126 (3)	0.6458 (2)	0.0224 (5)
C8	0.2211 (4)	0.3178 (3)	0.69625 (19)	0.0239 (5)
C9	0.2188 (4)	0.2833 (3)	0.8303 (2)	0.0340 (6)
H9A	0.1953	0.1640	0.8437	0.041*
H9B	0.0887	0.3444	0.8624	0.041*
C10A	0.4620 (14)	0.3401 (11)	0.8992 (5)	0.0306 (16)	0.611 (18)
H10A	0.4503	0.3460	0.9892	0.037*	0.611 (18)
H10B	0.5835	0.2570	0.8859	0.037*	0.611 (18)
C11A	0.5386 (11)	0.5076 (12)	0.8544 (5)	0.0329 (17)	0.611 (18)
H11A	0.4157	0.5905	0.8655	0.039*	0.611 (18)
H11B	0.6859	0.5422	0.9049	0.039*	0.611 (18)
C10B	0.370 (3)	0.3962 (18)	0.9091 (9)	0.042 (3)	0.389 (18)
H10C	0.3990	0.3500	0.9937	0.051*	0.389 (18)
H10D	0.2881	0.5032	0.9142	0.051*	0.389 (18)
C11B	0.599 (2)	0.423 (2)	0.8597 (8)	0.041 (3)	0.389 (18)
H11C	0.6828	0.3164	0.8589	0.049*	0.389 (18)
H11D	0.6971	0.4976	0.9168	0.049*	0.389 (18)
C12	0.5781 (4)	0.5011 (3)	0.7222 (2)	0.0306 (6)
H12A	0.7289	0.4441	0.7145	0.037*
H12B	0.5903	0.6148	0.6904	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0572 (4)	0.0399 (4)	0.0234 (3)	−0.0043 (4)	−0.0035 (3)	0.0000 (3)
N1	0.0233 (10)	0.0274 (10)	0.0266 (10)	−0.0076 (8)	0.0046 (9)	−0.0009 (8)
C1	0.0217 (11)	0.0173 (11)	0.0252 (10)	0.0023 (10)	0.0054 (8)	−0.0021 (10)
C2	0.0227 (11)	0.0200 (14)	0.0280 (12)	−0.0011 (9)	0.0005 (10)	−0.0029 (9)
C3	0.0324 (13)	0.0208 (15)	0.0244 (11)	0.0054 (10)	0.0000 (10)	−0.0007 (10)
C4	0.0334 (13)	0.0186 (12)	0.0286 (12)	−0.0002 (10)	0.0093 (11)	0.0038 (10)
C5	0.0219 (11)	0.0153 (11)	0.0386 (13)	0.0005 (9)	0.0038 (10)	0.0019 (10)
C6	0.0209 (11)	0.0147 (10)	0.0272 (12)	0.0033 (9)	0.0019 (9)	0.0000 (9)
C7	0.0192 (11)	0.0192 (11)	0.0281 (12)	0.0033 (9)	0.0004 (10)	−0.0039 (10)
C8	0.0229 (11)	0.0238 (12)	0.0242 (10)	0.0036 (11)	−0.0009 (9)	−0.0031 (11)
C9	0.0330 (14)	0.0425 (18)	0.0268 (13)	0.0012 (11)	0.0043 (11)	0.0001 (11)
C10A	0.027 (3)	0.041 (4)	0.022 (2)	−0.001 (3)	−0.003 (2)	−0.007 (3)
C11A	0.027 (3)	0.031 (4)	0.038 (3)	0.006 (2)	−0.010 (2)	−0.009 (3)
C10B	0.040 (7)	0.059 (7)	0.027 (4)	0.001 (5)	0.000 (5)	0.000 (4)
C11B	0.035 (6)	0.048 (7)	0.037 (4)	−0.007 (5)	−0.013 (4)	−0.003 (5)
C12	0.0307 (13)	0.0183 (12)	0.0403 (14)	−0.0009 (10)	−0.0065 (11)	−0.0030 (11)

Geometric parameters (Å, º)

Cl1—C3	1.751 (2)	C9—C10A	1.569 (6)
N1—C1	1.372 (3)	C9—H9A	0.9900
N1—C8	1.386 (3)	C9—H9B	0.9900
N1—H1	0.8800	C10A—C11A	1.525 (13)
C1—C2	1.398 (3)	C10A—H10A	0.9900
C1—C6	1.415 (3)	C10A—H10B	0.9900
C2—C3	1.372 (3)	C11A—C12	1.482 (6)
C2—H2	0.9500	C11A—H11A	0.9900
C3—C4	1.398 (3)	C11A—H11B	0.9900
C4—C5	1.373 (3)	C10B—C11B	1.49 (2)
C4—H4	0.9500	C10B—H10C	0.9900
C5—C6	1.403 (3)	C10B—H10D	0.9900
C5—H5	0.9500	C11B—C12	1.615 (10)
C6—C7	1.434 (3)	C11B—H11C	0.9900
C7—C8	1.361 (3)	C11B—H11D	0.9900
C7—C12	1.499 (3)	C12—H12A	0.9900
C8—C9	1.487 (3)	C12—H12B	0.9900
C9—C10B	1.464 (10)
C1—N1—C8	108.76 (18)	H9A—C9—H9B	108.5
C1—N1—H1	125.6	C11A—C10A—C9	112.3 (6)
C8—N1—H1	125.6	C11A—C10A—H10A	109.1
N1—C1—C2	129.7 (2)	C9—C10A—H10A	109.1
N1—C1—C6	107.71 (18)	C11A—C10A—H10B	109.1
C2—C1—C6	122.6 (2)	C9—C10A—H10B	109.1
C3—C2—C1	115.9 (2)	H10A—C10A—H10B	107.9
C3—C2—H2	122.1	C12—C11A—C10A	111.1 (7)
C1—C2—H2	122.1	C12—C11A—H11A	109.4
C2—C3—C4	123.5 (2)	C10A—C11A—H11A	109.4
C2—C3—Cl1	118.11 (18)	C12—C11A—H11B	109.4
C4—C3—Cl1	118.34 (17)	C10A—C11A—H11B	109.4
C5—C4—C3	119.9 (2)	H11A—C11A—H11B	108.0
C5—C4—H4	120.0	C9—C10B—C11B	111.4 (12)
C3—C4—H4	120.0	C9—C10B—H10C	109.4
C4—C5—C6	119.4 (2)	C11B—C10B—H10C	109.4
C4—C5—H5	120.3	C9—C10B—H10D	109.4
C6—C5—H5	120.3	C11B—C10B—H10D	109.4
C5—C6—C1	118.71 (19)	H10C—C10B—H10D	108.0
C5—C6—C7	134.6 (2)	C10B—C11B—C12	114.7 (11)
C1—C6—C7	106.73 (19)	C10B—C11B—H11C	108.6
C8—C7—C6	107.11 (19)	C12—C11B—H11C	108.6
C8—C7—C12	122.9 (2)	C10B—C11B—H11D	108.6
C6—C7—C12	129.9 (2)	C12—C11B—H11D	108.6
C7—C8—N1	109.69 (19)	H11C—C11B—H11D	107.6
C7—C8—C9	125.8 (2)	C11A—C12—C7	111.5 (3)
N1—C8—C9	124.5 (2)	C7—C12—C11B	107.3 (4)
C10B—C9—C8	112.6 (4)	C11A—C12—H12A	109.3
C8—C9—C10A	107.7 (3)	C7—C12—H12A	109.3
C10B—C9—H9A	127.3	C11B—C12—H12A	85.6
C8—C9—H9A	110.2	C11A—C12—H12B	109.3
C10A—C9—H9A	110.2	C7—C12—H12B	109.3
C10B—C9—H9B	84.0	C11B—C12—H12B	133.4
C8—C9—H9B	110.2	H12A—C12—H12B	108.0
C10A—C9—H9B	110.2
C8—N1—C1—C2	−179.2 (2)	C12—C7—C8—C9	−2.1 (4)
C8—N1—C1—C6	1.0 (2)	C1—N1—C8—C7	−0.8 (3)
N1—C1—C2—C3	−178.9 (2)	C1—N1—C8—C9	179.1 (2)
C6—C1—C2—C3	0.9 (3)	C7—C8—C9—C10B	15.5 (9)
C1—C2—C3—C4	−0.1 (3)	N1—C8—C9—C10B	−164.3 (8)
C1—C2—C3—Cl1	179.02 (16)	C7—C8—C9—C10A	−12.8 (5)
C2—C3—C4—C5	−0.2 (3)	N1—C8—C9—C10A	167.4 (4)
Cl1—C3—C4—C5	−179.32 (17)	C10B—C9—C10A—C11A	−61.1 (13)
C3—C4—C5—C6	−0.3 (3)	C8—C9—C10A—C11A	44.1 (8)
C4—C5—C6—C1	1.1 (3)	C9—C10A—C11A—C12	−63.6 (10)
C4—C5—C6—C7	−180.0 (2)	C8—C9—C10B—C11B	−42.9 (17)
N1—C1—C6—C5	178.43 (19)	C10A—C9—C10B—C11B	41.9 (16)
C2—C1—C6—C5	−1.4 (3)	C9—C10B—C11B—C12	60 (2)
N1—C1—C6—C7	−0.8 (2)	C10A—C11A—C12—C7	45.7 (8)
C2—C1—C6—C7	179.3 (2)	C10A—C11A—C12—C11B	−40.9 (11)
C5—C6—C7—C8	−178.7 (2)	C8—C7—C12—C11A	−14.5 (5)
C1—C6—C7—C8	0.3 (2)	C6—C7—C12—C11A	162.3 (5)
C5—C6—C7—C12	4.0 (4)	C8—C7—C12—C11B	15.1 (8)
C1—C6—C7—C12	−176.9 (2)	C6—C7—C12—C11B	−168.0 (8)
C6—C7—C8—N1	0.3 (3)	C10B—C11B—C12—C11A	59.7 (17)
C12—C7—C8—N1	177.8 (2)	C10B—C11B—C12—C7	−43.7 (17)
C6—C7—C8—C9	−179.6 (2)

(HxCL4)

Crystal data

C12H12ClN	F(000) = 864
Mr = 205.68	Dx = 1.388 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9248 reflections
a = 24.4577 (12) Å	θ = 2.5–30.5°
b = 6.0867 (3) Å	µ = 0.34 mm^−1
c = 16.309 (1) Å	T = 100 K
β = 125.800 (3)°	Plate, colourless
V = 1969.15 (18) Å^3	0.51 × 0.33 × 0.15 mm
Z = 8

Data collection

Bruker APEX-II CCD diffractometer	3002 independent reflections
Radiation source: fine-focus sealed tube	2601 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 30.6°, θmin = 2.5°
Absorption correction: multi-scan SADABS	h = −34→34
Tmin = 0.845, Tmax = 0.950	k = −6→8
16814 measured reflections	l = −23→22

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: inferred from neighbouring sites
wR(F^2) = 0.101	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0511P)^2 + 1.6967P] where P = (Fo^2 + 2Fc^2)/3
3002 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.43 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
Cl1	0.455806 (13)	−0.15353 (5)	0.35318 (2)	0.02288 (10)
N1	0.22210 (5)	0.43143 (16)	0.14185 (7)	0.0162 (2)
H1	0.2126	0.5598	0.1555	0.019*
C1	0.28226 (5)	0.32026 (18)	0.20274 (8)	0.0140 (2)
C2	0.34070 (6)	0.37491 (19)	0.29723 (9)	0.0162 (2)
H2	0.3438	0.5087	0.3297	0.019*
C3	0.39403 (5)	0.2275 (2)	0.34214 (8)	0.0167 (2)
H3	0.4346	0.2602	0.4062	0.020*
C4	0.38816 (5)	0.03021 (19)	0.29305 (9)	0.0161 (2)
C5	0.33092 (5)	−0.02521 (18)	0.19905 (8)	0.0155 (2)
H5	0.3284	−0.1594	0.1672	0.019*
C6	0.27678 (5)	0.12264 (18)	0.15225 (8)	0.0135 (2)
C7	0.21084 (5)	0.12036 (18)	0.05860 (8)	0.0137 (2)
C8	0.17907 (5)	0.30778 (18)	0.05559 (8)	0.0146 (2)
C9	0.10755 (6)	0.36642 (19)	−0.02539 (9)	0.0183 (2)
H9A	0.1057	0.4760	−0.0718	0.022*
H9B	0.0861	0.4310	0.0050	0.022*
C10A	0.07010 (9)	0.1568 (4)	−0.08380 (19)	0.0186 (6)	0.643 (6)
H10A	0.0636	0.0616	−0.0409	0.022*	0.643 (6)
H10B	0.0250	0.1962	−0.1449	0.022*	0.643 (6)
C11A	0.10927 (10)	0.0304 (4)	−0.11515 (18)	0.0175 (5)	0.643 (6)
H11A	0.1160	0.1265	−0.1575	0.021*	0.643 (6)
H11B	0.0824	−0.0982	−0.1564	0.021*	0.643 (6)
C10B	0.07934 (19)	0.2146 (7)	−0.1155 (3)	0.0212 (11)	0.357 (6)
H10C	0.0947	0.2659	−0.1564	0.025*	0.357 (6)
H10D	0.0295	0.2234	−0.1583	0.025*	0.357 (6)
C11B	0.10043 (18)	−0.0235 (7)	−0.0857 (4)	0.0195 (10)	0.357 (6)
H11C	0.0787	−0.1152	−0.1474	0.023*	0.357 (6)
H11D	0.0850	−0.0763	−0.0450	0.023*	0.357 (6)
C12	0.17813 (5)	−0.04852 (19)	−0.02358 (9)	0.0175 (2)
H12A	0.1722	−0.1863	0.0027	0.021*
H12B	0.2078	−0.0803	−0.0449	0.021*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.01289 (14)	0.02337 (16)	0.02185 (16)	0.00255 (9)	0.00423 (11)	−0.00177 (11)
N1	0.0161 (4)	0.0146 (4)	0.0152 (4)	0.0013 (3)	0.0076 (4)	−0.0024 (3)
C1	0.0144 (5)	0.0147 (5)	0.0133 (5)	−0.0006 (4)	0.0083 (4)	−0.0007 (4)
C2	0.0176 (5)	0.0169 (5)	0.0141 (5)	−0.0030 (4)	0.0092 (4)	−0.0037 (4)
C3	0.0142 (5)	0.0201 (5)	0.0135 (5)	−0.0037 (4)	0.0068 (4)	−0.0029 (4)
C4	0.0121 (4)	0.0179 (5)	0.0152 (5)	0.0004 (4)	0.0063 (4)	0.0000 (4)
C5	0.0138 (4)	0.0153 (5)	0.0152 (5)	−0.0004 (4)	0.0073 (4)	−0.0024 (4)
C6	0.0129 (4)	0.0152 (5)	0.0125 (5)	−0.0014 (4)	0.0075 (4)	−0.0013 (4)
C7	0.0126 (4)	0.0144 (5)	0.0124 (5)	−0.0013 (4)	0.0063 (4)	−0.0015 (4)
C8	0.0147 (4)	0.0159 (5)	0.0121 (5)	−0.0007 (4)	0.0073 (4)	−0.0004 (4)
C9	0.0151 (5)	0.0193 (5)	0.0158 (5)	0.0034 (4)	0.0064 (4)	0.0005 (4)
C10A	0.0131 (8)	0.0228 (10)	0.0166 (10)	−0.0005 (7)	0.0069 (7)	−0.0001 (8)
C11A	0.0150 (8)	0.0195 (10)	0.0127 (9)	−0.0010 (7)	0.0051 (7)	−0.0022 (7)
C10B	0.0176 (15)	0.0253 (18)	0.0149 (17)	−0.0002 (13)	0.0063 (13)	0.0006 (14)
C11B	0.0153 (15)	0.0214 (18)	0.0146 (18)	−0.0046 (12)	0.0047 (13)	−0.0036 (14)
C12	0.0160 (5)	0.0160 (5)	0.0148 (5)	−0.0008 (4)	0.0058 (4)	−0.0037 (4)

Geometric parameters (Å, º)

Cl1—C4	1.7468 (11)	C9—C10A	1.534 (2)
N1—C1	1.3782 (14)	C9—H9A	0.9900
N1—C8	1.3860 (14)	C9—H9B	0.9900
N1—H1	0.8800	C10A—C11A	1.531 (4)
C1—C2	1.3969 (15)	C10A—H10A	0.9900
C1—C6	1.4191 (15)	C10A—H10B	0.9900
C2—C3	1.3875 (16)	C11A—C12	1.535 (2)
C2—H2	0.9500	C11A—H11A	0.9900
C3—C4	1.4033 (16)	C11A—H11B	0.9900
C3—H3	0.9500	C10B—C11B	1.520 (7)
C4—C5	1.3832 (15)	C10B—H10C	0.9900
C5—C6	1.4012 (15)	C10B—H10D	0.9900
C5—H5	0.9500	C11B—C12	1.552 (4)
C6—C7	1.4326 (14)	C11B—H11C	0.9900
C7—C8	1.3648 (15)	C11B—H11D	0.9900
C7—C12	1.4962 (15)	C12—H12A	0.9900
C8—C9	1.4930 (15)	C12—H12B	0.9900
C9—C10B	1.517 (4)
C1—N1—C8	108.75 (9)	H9A—C9—H9B	108.4
C1—N1—H1	125.6	C11A—C10A—C9	111.2 (2)
C8—N1—H1	125.6	C11A—C10A—H10A	109.4
N1—C1—C2	130.55 (10)	C9—C10A—H10A	109.4
N1—C1—C6	107.42 (9)	C11A—C10A—H10B	109.4
C2—C1—C6	122.03 (10)	C9—C10A—H10B	109.4
C3—C2—C1	117.88 (10)	H10A—C10A—H10B	108.0
C3—C2—H2	121.1	C10A—C11A—C12	112.2 (2)
C1—C2—H2	121.1	C10A—C11A—H11A	109.2
C2—C3—C4	120.09 (10)	C12—C11A—H11A	109.2
C2—C3—H3	120.0	C10A—C11A—H11B	109.2
C4—C3—H3	120.0	C12—C11A—H11B	109.2
C5—C4—C3	122.71 (10)	H11A—C11A—H11B	107.9
C5—C4—Cl1	118.57 (9)	C9—C10B—C11B	113.2 (4)
C3—C4—Cl1	118.71 (8)	C9—C10B—H10C	108.9
C4—C5—C6	117.93 (10)	C11B—C10B—H10C	108.9
C4—C5—H5	121.0	C9—C10B—H10D	108.9
C6—C5—H5	121.0	C11B—C10B—H10D	108.9
C5—C6—C1	119.33 (10)	H10C—C10B—H10D	107.7
C5—C6—C7	133.66 (10)	C10B—C11B—C12	111.1 (4)
C1—C6—C7	106.99 (9)	C10B—C11B—H11C	109.4
C8—C7—C6	107.00 (9)	C12—C11B—H11C	109.4
C8—C7—C12	123.18 (10)	C10B—C11B—H11D	109.4
C6—C7—C12	129.81 (10)	C12—C11B—H11D	109.4
C7—C8—N1	109.82 (9)	H11C—C11B—H11D	108.0
C7—C8—C9	125.41 (10)	C7—C12—C11A	111.35 (11)
N1—C8—C9	124.69 (10)	C7—C12—C11B	109.04 (16)
C8—C9—C10B	110.17 (16)	C7—C12—H12A	109.4
C8—C9—C10A	108.38 (11)	C11A—C12—H12A	109.4
C8—C9—H9A	110.0	C11B—C12—H12A	86.1
C10B—C9—H9A	83.0	C7—C12—H12B	109.4
C10A—C9—H9A	110.0	C11A—C12—H12B	109.4
C8—C9—H9B	110.0	C11B—C12—H12B	131.2
C10B—C9—H9B	130.7	H12A—C12—H12B	108.0
C10A—C9—H9B	110.0
C8—N1—C1—C2	−179.17 (12)	C12—C7—C8—C9	3.25 (18)
C8—N1—C1—C6	0.71 (13)	C1—N1—C8—C7	−1.24 (13)
N1—C1—C2—C3	179.05 (12)	C1—N1—C8—C9	175.73 (11)
C6—C1—C2—C3	−0.82 (17)	C7—C8—C9—C10B	−12.5 (3)
C1—C2—C3—C4	−0.36 (17)	N1—C8—C9—C10B	171.1 (3)
C2—C3—C4—C5	1.06 (18)	C7—C8—C9—C10A	18.1 (2)
C2—C3—C4—Cl1	−178.76 (9)	N1—C8—C9—C10A	−158.39 (16)
C3—C4—C5—C6	−0.53 (18)	C8—C9—C10A—C11A	−49.2 (3)
Cl1—C4—C5—C6	179.29 (9)	C10B—C9—C10A—C11A	49.4 (4)
C4—C5—C6—C1	−0.64 (17)	C9—C10A—C11A—C12	62.6 (3)
C4—C5—C6—C7	−178.78 (12)	C8—C9—C10B—C11B	41.2 (5)
N1—C1—C6—C5	−178.55 (10)	C10A—C9—C10B—C11B	−50.5 (5)
C2—C1—C6—C5	1.35 (17)	C9—C10B—C11B—C12	−61.9 (6)
N1—C1—C6—C7	0.04 (12)	C8—C7—C12—C11A	7.2 (2)
C2—C1—C6—C7	179.93 (10)	C6—C7—C12—C11A	−174.12 (17)
C5—C6—C7—C8	177.52 (12)	C8—C7—C12—C11B	−21.2 (3)
C1—C6—C7—C8	−0.78 (12)	C6—C7—C12—C11B	157.5 (3)
C5—C6—C7—C12	−1.3 (2)	C10A—C11A—C12—C7	−39.0 (3)
C1—C6—C7—C12	−179.63 (11)	C10A—C11A—C12—C11B	51.1 (4)
C6—C7—C8—N1	1.23 (13)	C10B—C11B—C12—C7	48.7 (5)
C12—C7—C8—N1	−179.82 (10)	C10B—C11B—C12—C11A	−51.2 (5)
C6—C7—C8—C9	−175.70 (11)

(HxF2)

Crystal data

C12H12FN	F(000) = 800
Mr = 189.23	Dx = 1.340 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7530 reflections
a = 17.4633 (7) Å	θ = 2.3–30.6°
b = 11.1118 (7) Å	µ = 0.09 mm^−1
c = 9.6718 (4) Å	T = 100 K
β = 91.282 (3)°	Block, colourless
V = 1876.33 (16) Å^3	0.42 × 0.35 × 0.21 mm
Z = 8

Data collection

Bruker APEX-II CCD diffractometer	2870 independent reflections
Radiation source: fine-focus sealed tube	2491 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 30.6°, θmin = 2.3°
Absorption correction: multi-scan SADABS	h = −24→20
Tmin = 0.962, Tmax = 0.981	k = −15→15
13542 measured reflections	l = −13→12

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0683P)^2 + 1.2047P] where P = (Fo^2 + 2Fc^2)/3
2870 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
F1	0.92018 (4)	−0.03548 (6)	0.64383 (7)	0.02511 (17)
N1	0.76446 (5)	0.02449 (8)	0.53512 (9)	0.01874 (19)
H1	0.7814	−0.0323	0.4803	0.022*
C1	0.80412 (6)	0.07465 (9)	0.64537 (10)	0.01744 (19)
C2	0.87599 (6)	0.04999 (9)	0.70323 (10)	0.0191 (2)
C3	0.90230 (6)	0.11086 (10)	0.81886 (10)	0.0212 (2)
H3	0.9510	0.0925	0.8591	0.025*
C4	0.85603 (6)	0.20070 (10)	0.87665 (10)	0.0212 (2)
H4	0.8744	0.2436	0.9556	0.025*
C5	0.78441 (6)	0.22811 (9)	0.82129 (10)	0.0199 (2)
H5	0.7541	0.2895	0.8612	0.024*
C6	0.75718 (6)	0.16404 (9)	0.70545 (10)	0.0172 (2)
C7	0.68670 (5)	0.16425 (9)	0.62658 (10)	0.0173 (2)
C8	0.69312 (5)	0.07894 (9)	0.52536 (10)	0.0179 (2)
C9	0.63198 (6)	0.04413 (10)	0.42238 (11)	0.0222 (2)
H9A	0.6119	−0.0366	0.4450	0.027*
H9B	0.6535	0.0409	0.3286	0.027*
C10	0.56711 (6)	0.13699 (10)	0.42573 (11)	0.0236 (2)
H10A	0.5824	0.2092	0.3731	0.028*
H10B	0.5208	0.1027	0.3797	0.028*
C11	0.54768 (6)	0.17423 (10)	0.57342 (11)	0.0242 (2)
H11A	0.5032	0.2296	0.5705	0.029*
H11B	0.5331	0.1020	0.6266	0.029*
C12	0.61548 (6)	0.23638 (9)	0.64661 (11)	0.0207 (2)
H12A	0.6222	0.3182	0.6083	0.025*
H12B	0.6054	0.2440	0.7466	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0229 (3)	0.0259 (3)	0.0267 (3)	0.0058 (2)	0.0023 (2)	−0.0022 (2)
N1	0.0198 (4)	0.0178 (4)	0.0187 (4)	0.0002 (3)	0.0016 (3)	−0.0031 (3)
C1	0.0200 (4)	0.0166 (4)	0.0158 (4)	−0.0025 (3)	0.0025 (3)	0.0006 (3)
C2	0.0194 (4)	0.0185 (4)	0.0195 (5)	0.0004 (3)	0.0041 (3)	0.0020 (3)
C3	0.0190 (4)	0.0256 (5)	0.0191 (5)	−0.0029 (4)	0.0013 (3)	0.0036 (4)
C4	0.0231 (5)	0.0244 (5)	0.0163 (4)	−0.0055 (4)	0.0014 (3)	−0.0009 (4)
C5	0.0230 (5)	0.0197 (5)	0.0171 (4)	−0.0023 (4)	0.0040 (3)	−0.0013 (3)
C6	0.0186 (4)	0.0173 (4)	0.0158 (4)	−0.0022 (3)	0.0037 (3)	0.0008 (3)
C7	0.0180 (4)	0.0175 (4)	0.0166 (4)	−0.0015 (3)	0.0029 (3)	0.0011 (3)
C8	0.0185 (4)	0.0174 (4)	0.0179 (4)	−0.0015 (3)	0.0018 (3)	0.0014 (3)
C9	0.0236 (5)	0.0217 (5)	0.0211 (5)	−0.0018 (4)	−0.0022 (4)	−0.0016 (4)
C10	0.0240 (5)	0.0246 (5)	0.0221 (5)	−0.0009 (4)	−0.0026 (4)	0.0025 (4)
C11	0.0187 (5)	0.0284 (5)	0.0256 (5)	−0.0001 (4)	0.0017 (4)	0.0028 (4)
C12	0.0201 (4)	0.0211 (5)	0.0211 (5)	0.0017 (4)	0.0036 (3)	0.0000 (4)

Geometric parameters (Å, º)

F1—C2	1.3591 (12)	C7—C8	1.3691 (14)
N1—C1	1.3764 (12)	C7—C12	1.4960 (14)
N1—C8	1.3862 (13)	C8—C9	1.4948 (14)
N1—H1	0.8800	C9—C10	1.5332 (15)
C1—C2	1.3900 (14)	C9—H9A	0.9900
C1—C6	1.4204 (13)	C9—H9B	0.9900
C2—C3	1.3771 (14)	C10—C11	1.5325 (15)
C3—C4	1.4078 (15)	C10—H10A	0.9900
C3—H3	0.9500	C10—H10B	0.9900
C4—C5	1.3834 (14)	C11—C12	1.5305 (15)
C4—H4	0.9500	C11—H11A	0.9900
C5—C6	1.4016 (14)	C11—H11B	0.9900
C5—H5	0.9500	C12—H12A	0.9900
C6—C7	1.4333 (14)	C12—H12B	0.9900
C1—N1—C8	108.17 (8)	N1—C8—C9	124.05 (9)
C1—N1—H1	125.9	C8—C9—C10	109.20 (9)
C8—N1—H1	125.9	C8—C9—H9A	109.8
N1—C1—C2	131.78 (9)	C10—C9—H9A	109.8
N1—C1—C6	108.36 (9)	C8—C9—H9B	109.8
C2—C1—C6	119.83 (9)	C10—C9—H9B	109.8
F1—C2—C3	120.28 (9)	H9A—C9—H9B	108.3
F1—C2—C1	118.93 (9)	C11—C10—C9	112.37 (9)
C3—C2—C1	120.79 (9)	C11—C10—H10A	109.1
C2—C3—C4	119.12 (9)	C9—C10—H10A	109.1
C2—C3—H3	120.4	C11—C10—H10B	109.1
C4—C3—H3	120.4	C9—C10—H10B	109.1
C5—C4—C3	121.63 (9)	H10A—C10—H10B	107.9
C5—C4—H4	119.2	C12—C11—C10	111.57 (8)
C3—C4—H4	119.2	C12—C11—H11A	109.3
C4—C5—C6	119.03 (9)	C10—C11—H11A	109.3
C4—C5—H5	120.5	C12—C11—H11B	109.3
C6—C5—H5	120.5	C10—C11—H11B	109.3
C5—C6—C1	119.58 (9)	H11A—C11—H11B	108.0
C5—C6—C7	134.15 (9)	C7—C12—C11	109.58 (9)
C1—C6—C7	106.26 (8)	C7—C12—H12A	109.8
C8—C7—C6	107.24 (8)	C11—C12—H12A	109.8
C8—C7—C12	123.04 (9)	C7—C12—H12B	109.8
C6—C7—C12	129.68 (9)	C11—C12—H12B	109.8
C7—C8—N1	109.96 (9)	H12A—C12—H12B	108.2
C7—C8—C9	125.94 (9)
C8—N1—C1—C2	177.16 (10)	C1—C6—C7—C8	−0.21 (10)
C8—N1—C1—C6	−0.84 (11)	C5—C6—C7—C12	−1.19 (18)
N1—C1—C2—F1	2.50 (16)	C1—C6—C7—C12	177.30 (10)
C6—C1—C2—F1	−179.70 (8)	C6—C7—C8—N1	−0.30 (11)
N1—C1—C2—C3	−177.49 (10)	C12—C7—C8—N1	−178.01 (9)
C6—C1—C2—C3	0.31 (15)	C6—C7—C8—C9	177.17 (9)
F1—C2—C3—C4	178.70 (9)	C12—C7—C8—C9	−0.54 (16)
C1—C2—C3—C4	−1.31 (15)	C1—N1—C8—C7	0.72 (11)
C2—C3—C4—C5	0.91 (15)	C1—N1—C8—C9	−176.81 (9)
C3—C4—C5—C6	0.50 (15)	C7—C8—C9—C10	12.50 (14)
C4—C5—C6—C1	−1.50 (14)	N1—C8—C9—C10	−170.37 (9)
C4—C5—C6—C7	176.82 (10)	C8—C9—C10—C11	−42.27 (12)
N1—C1—C6—C5	179.39 (9)	C9—C10—C11—C12	62.98 (12)
C2—C1—C6—C5	1.12 (14)	C8—C7—C12—C11	18.03 (13)
N1—C1—C6—C7	0.64 (10)	C6—C7—C12—C11	−159.12 (10)
C2—C1—C6—C7	−177.63 (9)	C10—C11—C12—C7	−47.60 (12)
C5—C6—C7—C8	−178.69 (11)

(HxF3)

Crystal data

C12H12FN	F(000) = 400
Mr = 189.23	Dx = 1.368 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7713 reflections
a = 6.1937 (6) Å	θ = 2.9–30.1°
b = 7.4492 (8) Å	µ = 0.09 mm^−1
c = 19.920 (2) Å	T = 100 K
V = 919.06 (16) Å^3	Plate, colourless
Z = 4	0.51 × 0.33 × 0.14 mm

Data collection

Bruker APEX-II CCD diffractometer	2806 independent reflections
Radiation source: fine-focus sealed tube	2449 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 30.6°, θmin = 2.9°
Absorption correction: multi-scan SADABS	h = −8→8
Tmin = 0.954, Tmax = 0.987	k = −8→10
13579 measured reflections	l = −28→28

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0616P)^2 + 0.1317P] where P = (Fo^2 + 2Fc^2)/3
2806 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
F1	1.09041 (15)	−0.15162 (13)	0.30553 (4)	0.0227 (2)
N1	1.23200 (18)	−0.07909 (17)	0.54325 (6)	0.0147 (3)
H1	1.3622	−0.1237	0.5491	0.018*
C1	1.1229 (2)	−0.07122 (19)	0.48324 (7)	0.0134 (3)
C2	1.1851 (2)	−0.13009 (19)	0.41932 (7)	0.0151 (3)
H2	1.3192	−0.1882	0.4114	0.018*
C3	1.0386 (2)	−0.0979 (2)	0.36892 (7)	0.0161 (3)
C4	0.8397 (2)	−0.0140 (2)	0.37787 (7)	0.0161 (3)
H4	0.7462	0.0047	0.3407	0.019*
C5	0.7798 (2)	0.0418 (2)	0.44167 (7)	0.0151 (3)
H5	0.6446	0.0990	0.4487	0.018*
C6	0.9207 (2)	0.01295 (18)	0.49555 (6)	0.0123 (3)
C7	0.9132 (2)	0.05264 (18)	0.56604 (6)	0.0125 (3)
C8	1.1028 (2)	−0.00496 (19)	0.59332 (6)	0.0131 (3)
C9	1.1674 (2)	0.0110 (2)	0.66534 (7)	0.0166 (3)
H9A	1.2753	0.1081	0.6706	0.020*
H9B	1.2334	−0.1028	0.6808	0.020*
C10	0.9663 (2)	0.0532 (2)	0.70753 (7)	0.0173 (3)
H10A	0.8803	−0.0577	0.7133	0.021*
H10B	1.0118	0.0945	0.7526	0.021*
C11	0.8252 (2)	0.1977 (2)	0.67489 (7)	0.0167 (3)
H11A	0.9119	0.3079	0.6682	0.020*
H11B	0.7039	0.2274	0.7053	0.020*
C12	0.7354 (2)	0.1348 (2)	0.60703 (7)	0.0152 (3)
H12A	0.6196	0.0453	0.6144	0.018*
H12B	0.6727	0.2382	0.5826	0.018*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0277 (5)	0.0284 (5)	0.0121 (4)	0.0005 (4)	0.0026 (4)	−0.0035 (3)
N1	0.0116 (5)	0.0187 (6)	0.0138 (5)	0.0032 (5)	−0.0021 (4)	−0.0009 (5)
C1	0.0138 (6)	0.0134 (6)	0.0131 (6)	0.0002 (5)	−0.0007 (5)	0.0022 (5)
C2	0.0156 (6)	0.0125 (6)	0.0173 (6)	0.0008 (5)	0.0013 (5)	−0.0008 (5)
C3	0.0216 (7)	0.0149 (7)	0.0119 (6)	−0.0028 (5)	0.0020 (5)	−0.0003 (5)
C4	0.0173 (6)	0.0172 (7)	0.0139 (6)	−0.0013 (5)	−0.0031 (5)	0.0019 (5)
C5	0.0136 (6)	0.0153 (7)	0.0163 (6)	0.0006 (5)	−0.0024 (5)	0.0002 (5)
C6	0.0121 (6)	0.0107 (6)	0.0141 (6)	−0.0012 (5)	0.0003 (5)	0.0002 (5)
C7	0.0133 (6)	0.0113 (6)	0.0128 (6)	−0.0012 (5)	0.0001 (5)	0.0000 (5)
C8	0.0141 (6)	0.0131 (6)	0.0122 (5)	−0.0004 (5)	0.0011 (5)	0.0003 (5)
C9	0.0157 (6)	0.0213 (7)	0.0127 (6)	0.0015 (6)	−0.0029 (5)	−0.0003 (5)
C10	0.0177 (6)	0.0226 (8)	0.0117 (6)	−0.0011 (6)	0.0012 (5)	0.0004 (5)
C11	0.0155 (6)	0.0192 (7)	0.0153 (6)	0.0003 (6)	0.0021 (5)	−0.0034 (5)
C12	0.0125 (6)	0.0169 (7)	0.0164 (6)	0.0015 (5)	−0.0002 (5)	−0.0024 (5)

Geometric parameters (Å, º)

F1—C3	1.3629 (15)	C7—C8	1.3637 (19)
N1—C1	1.3743 (17)	C7—C12	1.5012 (19)
N1—C8	1.3928 (17)	C8—C9	1.4940 (18)
N1—H1	0.8800	C9—C10	1.5352 (19)
C1—C2	1.4007 (19)	C9—H9A	0.9900
C1—C6	1.4219 (19)	C9—H9B	0.9900
C2—C3	1.3744 (19)	C10—C11	1.531 (2)
C2—H2	0.9500	C10—H10A	0.9900
C3—C4	1.393 (2)	C10—H10B	0.9900
C4—C5	1.3878 (19)	C11—C12	1.5351 (19)
C4—H4	0.9500	C11—H11A	0.9900
C5—C6	1.3999 (19)	C11—H11B	0.9900
C5—H5	0.9500	C12—H12A	0.9900
C6—C7	1.4357 (19)	C12—H12B	0.9900
C1—N1—C8	108.88 (11)	N1—C8—C9	124.43 (12)
C1—N1—H1	125.6	C8—C9—C10	108.94 (11)
C8—N1—H1	125.6	C8—C9—H9A	109.9
N1—C1—C2	129.95 (12)	C10—C9—H9A	109.9
N1—C1—C6	107.57 (11)	C8—C9—H9B	109.9
C2—C1—C6	122.48 (12)	C10—C9—H9B	109.9
C3—C2—C1	115.34 (13)	H9A—C9—H9B	108.3
C3—C2—H2	122.3	C11—C10—C9	112.00 (11)
C1—C2—H2	122.3	C11—C10—H10A	109.2
F1—C3—C2	118.05 (13)	C9—C10—H10A	109.2
F1—C3—C4	117.29 (12)	C11—C10—H10B	109.2
C2—C3—C4	124.66 (13)	C9—C10—H10B	109.2
C5—C4—C3	119.22 (13)	H10A—C10—H10B	107.9
C5—C4—H4	120.4	C10—C11—C12	111.50 (12)
C3—C4—H4	120.4	C10—C11—H11A	109.3
C4—C5—C6	119.30 (13)	C12—C11—H11A	109.3
C4—C5—H5	120.4	C10—C11—H11B	109.3
C6—C5—H5	120.4	C12—C11—H11B	109.3
C5—C6—C1	118.99 (12)	H11A—C11—H11B	108.0
C5—C6—C7	134.26 (13)	C7—C12—C11	109.72 (11)
C1—C6—C7	106.74 (12)	C7—C12—H12A	109.7
C8—C7—C6	107.27 (12)	C11—C12—H12A	109.7
C8—C7—C12	122.91 (12)	C7—C12—H12B	109.7
C6—C7—C12	129.78 (12)	C11—C12—H12B	109.7
C7—C8—N1	109.52 (11)	H12A—C12—H12B	108.2
C7—C8—C9	126.04 (12)
C8—N1—C1—C2	−179.32 (15)	C1—C6—C7—C8	0.32 (15)
C8—N1—C1—C6	0.98 (16)	C5—C6—C7—C12	3.6 (3)
N1—C1—C2—C3	−178.52 (14)	C1—C6—C7—C12	−177.50 (14)
C6—C1—C2—C3	1.1 (2)	C6—C7—C8—N1	0.28 (16)
C1—C2—C3—F1	179.76 (12)	C12—C7—C8—N1	178.28 (13)
C1—C2—C3—C4	−0.2 (2)	C6—C7—C8—C9	179.11 (14)
F1—C3—C4—C5	179.60 (13)	C12—C7—C8—C9	−2.9 (2)
C2—C3—C4—C5	−0.4 (2)	C1—N1—C8—C7	−0.80 (16)
C3—C4—C5—C6	0.1 (2)	C1—N1—C8—C9	−179.65 (13)
C4—C5—C6—C1	0.7 (2)	C7—C8—C9—C10	15.7 (2)
C4—C5—C6—C7	179.53 (15)	N1—C8—C9—C10	−165.64 (13)
N1—C1—C6—C5	178.33 (12)	C8—C9—C10—C11	−44.44 (17)
C2—C1—C6—C5	−1.4 (2)	C9—C10—C11—C12	63.30 (16)
N1—C1—C6—C7	−0.80 (15)	C8—C7—C12—C11	18.21 (19)
C2—C1—C6—C7	179.48 (13)	C6—C7—C12—C11	−164.27 (14)
C5—C6—C7—C8	−178.62 (15)	C10—C11—C12—C7	−46.95 (16)

(HxF4_I)

Crystal data

C12H12FN	F(000) = 400
Mr = 189.23	Dx = 1.317 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7741 reflections
a = 6.0226 (4) Å	θ = 2.8–29.7°
b = 7.8459 (6) Å	µ = 0.09 mm^−1
c = 20.1968 (14) Å	T = 100 K
V = 954.35 (12) Å^3	PLATE, colourless
Z = 4	0.43 × 0.16 × 0.05 mm

Data collection

Bruker APEX-II CCD diffractometer	2928 independent reflections
Radiation source: fine-focus sealed tube	2429 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
φ and ω scans	θmax = 30.6°, θmin = 2.8°
Absorption correction: multi-scan SADABS	h = −8→8
Tmin = 0.962, Tmax = 0.996	k = −11→10
25718 measured reflections	l = −28→28

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.116	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0601P)^2 + 0.2147P] where P = (Fo^2 + 2Fc^2)/3
2928 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.28 e Å^−3
3 restraints	Δρmin = −0.29 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
F1	1.1922 (2)	−0.03453 (15)	0.67274 (5)	0.0406 (3)
N1	0.7099 (2)	0.10305 (17)	0.45159 (6)	0.0234 (3)
H1	0.5858	0.1589	0.4440	0.028*
C1	0.8067 (2)	0.07927 (17)	0.51272 (7)	0.0185 (3)
C2	1.0018 (2)	−0.01816 (18)	0.50303 (7)	0.0175 (3)
C3	1.1358 (3)	−0.05919 (19)	0.55774 (7)	0.0227 (3)
H3	1.2675	−0.1248	0.5531	0.027*
C4	1.0668 (3)	0.0003 (2)	0.61808 (7)	0.0252 (3)
C5	0.8755 (3)	0.09568 (19)	0.62831 (7)	0.0236 (3)
H5	0.8373	0.1328	0.6716	0.028*
C6	0.7407 (3)	0.13636 (18)	0.57505 (7)	0.0230 (3)
H6	0.6084	0.2007	0.5808	0.028*
C7	0.8401 (2)	0.02455 (19)	0.40405 (7)	0.0206 (3)
C8	1.0182 (2)	−0.05175 (17)	0.43326 (7)	0.0183 (3)
C9	1.1957 (3)	−0.14330 (19)	0.39546 (7)	0.0240 (3)
H9A	1.1733	−0.2680	0.3990	0.029*
H9B	1.3432	−0.1154	0.4142	0.029*
C10A	1.1855 (6)	−0.0872 (6)	0.32062 (14)	0.0265 (9)	0.556 (8)
H10A	1.2513	0.0279	0.3161	0.032*	0.556 (8)
H10B	1.2755	−0.1669	0.2938	0.032*	0.556 (8)
C11A	0.9466 (7)	−0.0841 (6)	0.29359 (19)	0.0288 (9)	0.556 (8)
H11A	0.9500	−0.0478	0.2467	0.035*	0.556 (8)
H11B	0.8849	−0.2010	0.2952	0.035*	0.556 (8)
C10B	1.1315 (8)	−0.1739 (8)	0.3265 (2)	0.0300 (12)	0.444 (8)
H10C	1.0339	−0.2753	0.3244	0.036*	0.444 (8)
H10D	1.2661	−0.1984	0.3000	0.036*	0.444 (8)
C11B	1.0116 (10)	−0.0231 (8)	0.2968 (2)	0.0282 (11)	0.444 (8)
H11C	0.9758	−0.0505	0.2501	0.034*	0.444 (8)
H11D	1.1149	0.0750	0.2964	0.034*	0.444 (8)
C12	0.7972 (3)	0.0325 (2)	0.33132 (7)	0.0309 (4)
H12A	0.8196	0.1508	0.3157	0.037*
H12B	0.6407	0.0009	0.3226	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0457 (6)	0.0496 (6)	0.0265 (5)	0.0116 (5)	−0.0150 (5)	0.0001 (5)
N1	0.0164 (6)	0.0266 (6)	0.0272 (6)	0.0054 (5)	−0.0017 (5)	0.0014 (5)
C1	0.0168 (7)	0.0147 (6)	0.0240 (7)	0.0004 (5)	−0.0005 (6)	0.0016 (5)
C2	0.0167 (6)	0.0125 (6)	0.0233 (7)	−0.0007 (5)	−0.0007 (5)	0.0009 (5)
C3	0.0213 (7)	0.0202 (7)	0.0267 (7)	0.0027 (6)	−0.0029 (6)	0.0016 (6)
C4	0.0294 (8)	0.0225 (8)	0.0236 (7)	0.0008 (6)	−0.0070 (6)	0.0023 (6)
C5	0.0293 (8)	0.0193 (7)	0.0223 (7)	−0.0020 (6)	0.0040 (6)	−0.0016 (6)
C6	0.0220 (8)	0.0183 (6)	0.0289 (8)	0.0009 (6)	0.0043 (6)	−0.0002 (5)
C7	0.0191 (7)	0.0195 (6)	0.0233 (6)	−0.0020 (6)	−0.0016 (5)	−0.0003 (5)
C8	0.0172 (6)	0.0155 (6)	0.0222 (6)	−0.0013 (5)	−0.0002 (5)	−0.0003 (5)
C9	0.0224 (8)	0.0208 (7)	0.0287 (8)	0.0021 (6)	0.0033 (6)	−0.0034 (6)
C10A	0.0262 (17)	0.030 (2)	0.0232 (13)	−0.0079 (15)	0.0034 (12)	−0.0018 (13)
C11A	0.026 (2)	0.037 (2)	0.0237 (15)	−0.0140 (16)	−0.0034 (13)	−0.0022 (15)
C10B	0.030 (2)	0.034 (3)	0.0260 (19)	−0.005 (2)	0.0062 (16)	−0.0056 (18)
C11B	0.029 (3)	0.038 (3)	0.0173 (17)	−0.005 (2)	0.0028 (17)	−0.0009 (19)
C12	0.0244 (8)	0.0450 (9)	0.0233 (7)	−0.0021 (8)	−0.0045 (6)	−0.0011 (7)

Geometric parameters (Å, º)

F1—C4	1.3651 (17)	C9—C10A	1.576 (3)
N1—C1	1.3780 (19)	C9—H9A	0.9900
N1—C7	1.3841 (19)	C9—H9B	0.9900
N1—H1	0.8800	C10A—C11A	1.539 (6)
C1—C6	1.394 (2)	C10A—H10A	0.9900
C1—C2	1.416 (2)	C10A—H10B	0.9900
C2—C3	1.406 (2)	C11A—C12	1.493 (4)
C2—C8	1.437 (2)	C11A—H11A	0.9900
C3—C4	1.370 (2)	C11A—H11B	0.9900
C3—H3	0.9500	C10B—C11B	1.511 (7)
C4—C5	1.390 (2)	C10B—H10C	0.9900
C5—C6	1.385 (2)	C10B—H10D	0.9900
C5—H5	0.9500	C11B—C12	1.531 (5)
C6—H6	0.9500	C11B—H11C	0.9900
C7—C8	1.362 (2)	C11B—H11D	0.9900
C7—C12	1.493 (2)	C12—H12A	0.9900
C8—C9	1.497 (2)	C12—H12B	0.9900
C9—C10B	1.466 (4)
C1—N1—C7	108.77 (12)	H9A—C9—H9B	108.3
C1—N1—H1	125.6	C11A—C10A—C9	112.4 (3)
C7—N1—H1	125.6	C11A—C10A—H10A	109.1
N1—C1—C6	130.18 (14)	C9—C10A—H10A	109.1
N1—C1—C2	107.47 (12)	C11A—C10A—H10B	109.1
C6—C1—C2	122.34 (13)	C9—C10A—H10B	109.1
C3—C2—C1	119.45 (13)	H10A—C10A—H10B	107.9
C3—C2—C8	133.59 (14)	C12—C11A—C10A	113.1 (3)
C1—C2—C8	106.94 (12)	C12—C11A—H11A	109.0
C4—C3—C2	116.56 (14)	C10A—C11A—H11A	109.0
C4—C3—H3	121.7	C12—C11A—H11B	109.0
C2—C3—H3	121.7	C10A—C11A—H11B	109.0
F1—C4—C3	118.92 (14)	H11A—C11A—H11B	107.8
F1—C4—C5	116.51 (13)	C9—C10B—C11B	112.0 (4)
C3—C4—C5	124.57 (14)	C9—C10B—H10C	109.2
C6—C5—C4	119.65 (14)	C11B—C10B—H10C	109.2
C6—C5—H5	120.2	C9—C10B—H10D	109.2
C4—C5—H5	120.2	C11B—C10B—H10D	109.2
C5—C6—C1	117.41 (14)	H10C—C10B—H10D	107.9
C5—C6—H6	121.3	C10B—C11B—C12	116.4 (4)
C1—C6—H6	121.3	C10B—C11B—H11C	108.2
C8—C7—N1	109.94 (13)	C12—C11B—H11C	108.2
C8—C7—C12	125.50 (14)	C10B—C11B—H11D	108.2
N1—C7—C12	124.45 (14)	C12—C11B—H11D	108.2
C7—C8—C2	106.86 (13)	H11C—C11B—H11D	107.3
C7—C8—C9	123.52 (13)	C7—C12—C11A	111.86 (19)
C2—C8—C9	129.55 (13)	C7—C12—C11B	106.9 (2)
C10B—C9—C8	112.0 (2)	C7—C12—H12A	109.2
C8—C9—C10A	109.08 (16)	C11A—C12—H12A	109.2
C10B—C9—H9A	82.5	C11B—C12—H12A	90.4
C8—C9—H9A	109.9	C7—C12—H12B	109.2
C10A—C9—H9A	109.9	C11A—C12—H12B	109.2
C10B—C9—H9B	129.5	C11B—C12—H12B	130.6
C8—C9—H9B	109.9	H12A—C12—H12B	107.9
C10A—C9—H9B	109.9
C7—N1—C1—C6	178.71 (15)	C1—C2—C8—C7	0.42 (16)
C7—N1—C1—C2	−0.51 (16)	C3—C2—C8—C9	−1.3 (3)
N1—C1—C2—C3	179.05 (13)	C1—C2—C8—C9	177.45 (14)
C6—C1—C2—C3	−0.2 (2)	C7—C8—C9—C10B	−12.7 (3)
N1—C1—C2—C8	0.05 (15)	C2—C8—C9—C10B	170.7 (3)
C6—C1—C2—C8	−179.23 (13)	C7—C8—C9—C10A	17.9 (3)
C1—C2—C3—C4	−0.3 (2)	C2—C8—C9—C10A	−158.6 (2)
C8—C2—C3—C4	178.35 (15)	C10B—C9—C10A—C11A	56.3 (5)
C2—C3—C4—F1	−179.36 (14)	C8—C9—C10A—C11A	−44.9 (4)
C2—C3—C4—C5	0.5 (2)	C9—C10A—C11A—C12	58.5 (5)
F1—C4—C5—C6	179.77 (14)	C8—C9—C10B—C11B	40.3 (6)
C3—C4—C5—C6	−0.1 (2)	C10A—C9—C10B—C11B	−49.5 (5)
C4—C5—C6—C1	−0.5 (2)	C9—C10B—C11B—C12	−59.3 (8)
N1—C1—C6—C5	−178.48 (14)	C8—C7—C12—C11A	12.0 (3)
C2—C1—C6—C5	0.6 (2)	N1—C7—C12—C11A	−172.0 (2)
C1—N1—C7—C8	0.80 (17)	C8—C7—C12—C11B	−12.6 (3)
C1—N1—C7—C12	−175.76 (14)	N1—C7—C12—C11B	163.4 (3)
N1—C7—C8—C2	−0.74 (17)	C10A—C11A—C12—C7	−39.6 (5)
C12—C7—C8—C2	175.77 (14)	C10A—C11A—C12—C11B	42.6 (6)
N1—C7—C8—C9	−178.00 (13)	C10B—C11B—C12—C7	42.1 (6)
C12—C7—C8—C9	−1.5 (2)	C10B—C11B—C12—C11A	−64.0 (7)
C3—C2—C8—C7	−178.38 (16)

(HxF4_II)

Crystal data

C12H12FN	F(000) = 800
Mr = 189.23	Dx = 1.353 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9959 reflections
a = 10.5411 (11) Å	θ = 2.3–30.6°
b = 8.1081 (8) Å	µ = 0.09 mm^−1
c = 21.980 (2) Å	T = 100 K
β = 98.610 (2)°	BLOCK, colourless
V = 1857.4 (3) Å^3	0.62 × 0.34 × 0.22 mm
Z = 8

Data collection

Bruker APEX-II CCD diffractometer	5693 independent reflections
Radiation source: fine-focus sealed tube	4862 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
φ and ω scans	θmax = 30.6°, θmin = 2.3°
Absorption correction: multi-scan SADABS	h = −13→15
Tmin = 0.944, Tmax = 0.980	k = −11→11
24992 measured reflections	l = −29→31

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0608P)^2 + 0.7124P] where P = (Fo^2 + 2Fc^2)/3
5693 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.45 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
F1	0.39217 (6)	0.78959 (9)	0.28255 (3)	0.02305 (15)
F2	0.76893 (7)	0.31287 (9)	−0.03683 (3)	0.02504 (16)
N1	0.67546 (8)	0.50775 (10)	0.12241 (4)	0.01536 (17)
H1	0.6580	0.4380	0.0916	0.018*
N2	0.50074 (8)	0.01610 (11)	0.12634 (4)	0.01713 (17)
H2	0.5217	−0.0502	0.1580	0.021*
C1	0.58881 (9)	0.56572 (12)	0.15850 (4)	0.01384 (18)
C2	0.65613 (9)	0.67482 (11)	0.20254 (4)	0.01299 (18)
C3	0.58971 (9)	0.75204 (12)	0.24570 (4)	0.01523 (18)
H3	0.6314	0.8258	0.2758	0.018*
C4	0.46090 (10)	0.71529 (13)	0.24207 (5)	0.01628 (19)
C5	0.39396 (9)	0.60707 (13)	0.19925 (5)	0.0178 (2)
H5	0.3053	0.5862	0.1994	0.021*
C6	0.45866 (9)	0.53054 (13)	0.15654 (5)	0.01672 (19)
H6	0.4157	0.4565	0.1269	0.020*
C7	0.79439 (9)	0.57705 (12)	0.14245 (4)	0.01392 (18)
C8	0.78697 (9)	0.67917 (12)	0.19156 (4)	0.01372 (18)
C9	0.90030 (9)	0.77037 (13)	0.22503 (5)	0.01655 (19)
H9A	0.9036	0.7554	0.2699	0.020*
H9B	0.8911	0.8897	0.2159	0.020*
C10	1.02531 (10)	0.70621 (14)	0.20533 (5)	0.0198 (2)
H10A	1.0949	0.7869	0.2178	0.024*
H10B	1.0498	0.6011	0.2269	0.024*
C11	1.01177 (10)	0.67816 (14)	0.13575 (5)	0.0204 (2)
H11A	1.0960	0.6456	0.1247	0.025*
H11B	0.9853	0.7825	0.1141	0.025*
C12	0.91255 (9)	0.54364 (13)	0.11443 (5)	0.01628 (19)
H12A	0.8917	0.5443	0.0690	0.020*
H12B	0.9477	0.4339	0.1275	0.020*
C13	0.58439 (9)	0.08049 (12)	0.09000 (4)	0.01496 (18)
C14	0.51152 (9)	0.18020 (12)	0.04424 (4)	0.01368 (18)
C15	0.57378 (9)	0.26022 (12)	0.00040 (5)	0.01551 (19)
H15	0.5279	0.3267	−0.0311	0.019*
C16	0.70470 (10)	0.23790 (13)	0.00515 (5)	0.01719 (19)
C17	0.77749 (10)	0.14366 (13)	0.05069 (5)	0.0193 (2)
H17	0.8678	0.1351	0.0521	0.023*
C18	0.71695 (10)	0.06249 (13)	0.09393 (5)	0.0186 (2)
H18	0.7643	−0.0032	0.1252	0.022*
C19	0.37826 (9)	0.07284 (12)	0.10491 (5)	0.01544 (19)
C20	0.38102 (9)	0.17420 (12)	0.05534 (5)	0.01445 (18)
C21	0.26435 (9)	0.26211 (13)	0.02353 (5)	0.01636 (19)
H21A	0.2329	0.2067	−0.0160	0.020*
H21B	0.2868	0.3773	0.0146	0.020*
C22	0.15884 (10)	0.26129 (13)	0.06451 (5)	0.0198 (2)
H22A	0.0769	0.2971	0.0400	0.024*
H22B	0.1811	0.3411	0.0985	0.024*
C23	0.14129 (10)	0.08955 (14)	0.09146 (5)	0.0199 (2)
H23A	0.1199	0.0096	0.0574	0.024*
H23B	0.0686	0.0925	0.1152	0.024*
C24	0.26274 (10)	0.03136 (14)	0.13364 (5)	0.0196 (2)
H24A	0.2684	0.0860	0.1742	0.024*
H24B	0.2586	−0.0893	0.1400	0.024*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0220 (3)	0.0247 (3)	0.0249 (3)	0.0002 (3)	0.0114 (3)	−0.0045 (3)
F2	0.0243 (3)	0.0264 (4)	0.0272 (4)	−0.0018 (3)	0.0128 (3)	0.0012 (3)
N1	0.0157 (4)	0.0152 (4)	0.0147 (4)	−0.0006 (3)	0.0007 (3)	−0.0041 (3)
N2	0.0159 (4)	0.0180 (4)	0.0168 (4)	0.0022 (3)	0.0001 (3)	0.0044 (3)
C1	0.0152 (4)	0.0124 (4)	0.0132 (4)	0.0004 (3)	−0.0002 (3)	0.0001 (3)
C2	0.0150 (4)	0.0108 (4)	0.0127 (4)	0.0001 (3)	0.0006 (3)	0.0004 (3)
C3	0.0177 (4)	0.0136 (4)	0.0145 (4)	−0.0004 (3)	0.0027 (3)	−0.0004 (3)
C4	0.0179 (4)	0.0158 (4)	0.0160 (4)	0.0022 (4)	0.0053 (3)	0.0003 (3)
C5	0.0148 (4)	0.0179 (5)	0.0204 (5)	−0.0007 (4)	0.0015 (3)	0.0017 (4)
C6	0.0157 (4)	0.0164 (4)	0.0170 (4)	−0.0017 (3)	−0.0009 (3)	−0.0005 (4)
C7	0.0146 (4)	0.0128 (4)	0.0139 (4)	0.0005 (3)	0.0006 (3)	0.0006 (3)
C8	0.0143 (4)	0.0122 (4)	0.0141 (4)	−0.0002 (3)	0.0002 (3)	−0.0004 (3)
C9	0.0156 (4)	0.0158 (4)	0.0174 (4)	−0.0023 (3)	−0.0002 (3)	−0.0024 (4)
C10	0.0143 (4)	0.0201 (5)	0.0243 (5)	−0.0015 (4)	0.0004 (4)	−0.0035 (4)
C11	0.0177 (4)	0.0203 (5)	0.0241 (5)	−0.0022 (4)	0.0061 (4)	−0.0003 (4)
C12	0.0155 (4)	0.0178 (5)	0.0157 (4)	0.0015 (3)	0.0030 (3)	−0.0006 (3)
C13	0.0154 (4)	0.0137 (4)	0.0150 (4)	0.0013 (3)	−0.0003 (3)	−0.0009 (3)
C14	0.0146 (4)	0.0117 (4)	0.0141 (4)	0.0006 (3)	0.0000 (3)	−0.0019 (3)
C15	0.0177 (4)	0.0140 (4)	0.0147 (4)	0.0006 (3)	0.0018 (3)	−0.0015 (3)
C16	0.0179 (4)	0.0157 (4)	0.0190 (5)	−0.0017 (4)	0.0061 (4)	−0.0030 (4)
C17	0.0145 (4)	0.0195 (5)	0.0234 (5)	0.0009 (4)	0.0015 (4)	−0.0045 (4)
C18	0.0157 (4)	0.0189 (5)	0.0198 (5)	0.0030 (4)	−0.0020 (3)	−0.0014 (4)
C19	0.0147 (4)	0.0136 (4)	0.0176 (4)	0.0005 (3)	0.0009 (3)	−0.0005 (3)
C20	0.0138 (4)	0.0129 (4)	0.0161 (4)	0.0012 (3)	0.0003 (3)	−0.0010 (3)
C21	0.0150 (4)	0.0147 (4)	0.0186 (5)	0.0027 (3)	0.0000 (3)	0.0009 (3)
C22	0.0150 (4)	0.0189 (5)	0.0254 (5)	0.0029 (4)	0.0024 (4)	−0.0002 (4)
C23	0.0153 (4)	0.0207 (5)	0.0236 (5)	−0.0017 (4)	0.0025 (4)	−0.0006 (4)
C24	0.0173 (4)	0.0210 (5)	0.0209 (5)	−0.0005 (4)	0.0040 (4)	0.0031 (4)

Geometric parameters (Å, º)

F1—C4	1.3685 (12)	C11—H11A	0.9900
F2—C16	1.3662 (12)	C11—H11B	0.9900
N1—C1	1.3789 (13)	C12—H12A	0.9900
N1—C7	1.3843 (12)	C12—H12B	0.9900
N1—H1	0.8800	C13—C18	1.3946 (13)
N2—C13	1.3782 (13)	C13—C14	1.4226 (13)
N2—C19	1.3850 (12)	C14—C15	1.4033 (14)
N2—H2	0.8800	C14—C20	1.4335 (13)
C1—C6	1.3956 (13)	C15—C16	1.3802 (14)
C1—C2	1.4203 (13)	C15—H15	0.9500
C2—C3	1.4076 (13)	C16—C17	1.3944 (15)
C2—C8	1.4358 (13)	C17—C18	1.3876 (16)
C3—C4	1.3807 (14)	C17—H17	0.9500
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.3982 (14)	C19—C20	1.3685 (14)
C5—C6	1.3868 (15)	C19—C24	1.4916 (14)
C5—H5	0.9500	C20—C21	1.5007 (13)
C6—H6	0.9500	C21—C22	1.5324 (15)
C7—C8	1.3718 (13)	C21—H21A	0.9900
C7—C12	1.4946 (14)	C21—H21B	0.9900
C8—C9	1.5007 (13)	C22—C23	1.5352 (15)
C9—C10	1.5381 (14)	C22—H22A	0.9900
C9—H9A	0.9900	C22—H22B	0.9900
C9—H9B	0.9900	C23—C24	1.5381 (14)
C10—C11	1.5315 (16)	C23—H23A	0.9900
C10—H10A	0.9900	C23—H23B	0.9900
C10—H10B	0.9900	C24—H24A	0.9900
C11—C12	1.5350 (14)	C24—H24B	0.9900
C1—N1—C7	108.96 (8)	C7—C12—H12B	110.0
C1—N1—H1	125.5	C11—C12—H12B	110.0
C7—N1—H1	125.5	H12A—C12—H12B	108.4
C13—N2—C19	108.77 (8)	N2—C13—C18	130.28 (9)
C13—N2—H2	125.6	N2—C13—C14	107.49 (8)
C19—N2—H2	125.6	C18—C13—C14	122.22 (9)
N1—C1—C6	130.18 (9)	C15—C14—C13	119.32 (9)
N1—C1—C2	107.34 (8)	C15—C14—C20	133.78 (9)
C6—C1—C2	122.47 (9)	C13—C14—C20	106.90 (9)
C3—C2—C1	119.22 (9)	C16—C15—C14	116.90 (9)
C3—C2—C8	133.60 (9)	C16—C15—H15	121.5
C1—C2—C8	107.17 (8)	C14—C15—H15	121.5
C4—C3—C2	116.68 (9)	F2—C16—C15	118.79 (9)
C4—C3—H3	121.7	F2—C16—C17	116.97 (9)
C2—C3—H3	121.7	C15—C16—C17	124.24 (10)
F1—C4—C3	118.63 (9)	C18—C17—C16	119.44 (9)
F1—C4—C5	116.81 (9)	C18—C17—H17	120.3
C3—C4—C5	124.56 (9)	C16—C17—H17	120.3
C6—C5—C4	119.12 (9)	C17—C18—C13	117.85 (9)
C6—C5—H5	120.4	C17—C18—H18	121.1
C4—C5—H5	120.4	C13—C18—H18	121.1
C5—C6—C1	117.93 (9)	C20—C19—N2	109.90 (9)
C5—C6—H6	121.0	C20—C19—C24	126.05 (9)
C1—C6—H6	121.0	N2—C19—C24	124.03 (9)
C8—C7—N1	109.86 (9)	C19—C20—C14	106.93 (8)
C8—C7—C12	125.65 (9)	C19—C20—C21	122.86 (9)
N1—C7—C12	124.49 (9)	C14—C20—C21	130.16 (9)
C7—C8—C2	106.66 (8)	C20—C21—C22	109.90 (8)
C7—C8—C9	123.25 (9)	C20—C21—H21A	109.7
C2—C8—C9	130.08 (9)	C22—C21—H21A	109.7
C8—C9—C10	110.36 (8)	C20—C21—H21B	109.7
C8—C9—H9A	109.6	C22—C21—H21B	109.7
C10—C9—H9A	109.6	H21A—C21—H21B	108.2
C8—C9—H9B	109.6	C21—C22—C23	111.76 (9)
C10—C9—H9B	109.6	C21—C22—H22A	109.3
H9A—C9—H9B	108.1	C23—C22—H22A	109.3
C11—C10—C9	112.07 (8)	C21—C22—H22B	109.3
C11—C10—H10A	109.2	C23—C22—H22B	109.3
C9—C10—H10A	109.2	H22A—C22—H22B	107.9
C11—C10—H10B	109.2	C22—C23—C24	111.92 (8)
C9—C10—H10B	109.2	C22—C23—H23A	109.2
H10A—C10—H10B	107.9	C24—C23—H23A	109.2
C10—C11—C12	111.58 (9)	C22—C23—H23B	109.2
C10—C11—H11A	109.3	C24—C23—H23B	109.2
C12—C11—H11A	109.3	H23A—C23—H23B	107.9
C10—C11—H11B	109.3	C19—C24—C23	109.53 (9)
C12—C11—H11B	109.3	C19—C24—H24A	109.8
H11A—C11—H11B	108.0	C23—C24—H24A	109.8
C7—C12—C11	108.49 (8)	C19—C24—H24B	109.8
C7—C12—H12A	110.0	C23—C24—H24B	109.8
C11—C12—H12A	110.0	H24A—C24—H24B	108.2
C7—N1—C1—C6	−179.31 (10)	C19—N2—C13—C18	178.47 (10)
C7—N1—C1—C2	−0.02 (11)	C19—N2—C13—C14	−0.23 (11)
N1—C1—C2—C3	−179.90 (8)	N2—C13—C14—C15	−179.50 (8)
C6—C1—C2—C3	−0.54 (14)	C18—C13—C14—C15	1.68 (15)
N1—C1—C2—C8	−0.30 (10)	N2—C13—C14—C20	0.73 (11)
C6—C1—C2—C8	179.05 (9)	C18—C13—C14—C20	−178.10 (9)
C1—C2—C3—C4	0.03 (14)	C13—C14—C15—C16	−0.75 (14)
C8—C2—C3—C4	−179.44 (10)	C20—C14—C15—C16	178.96 (10)
C2—C3—C4—F1	−179.02 (8)	C14—C15—C16—F2	179.62 (8)
C2—C3—C4—C5	0.53 (15)	C14—C15—C16—C17	−0.81 (15)
F1—C4—C5—C6	178.98 (9)	F2—C16—C17—C18	−178.93 (9)
C3—C4—C5—C6	−0.57 (16)	C15—C16—C17—C18	1.49 (16)
C4—C5—C6—C1	0.04 (15)	C16—C17—C18—C13	−0.53 (15)
N1—C1—C6—C5	179.70 (10)	N2—C13—C18—C17	−179.54 (10)
C2—C1—C6—C5	0.50 (15)	C14—C13—C18—C17	−1.01 (15)
C1—N1—C7—C8	0.36 (11)	C13—N2—C19—C20	−0.39 (12)
C1—N1—C7—C12	−179.92 (9)	C13—N2—C19—C24	−178.81 (9)
N1—C7—C8—C2	−0.54 (11)	N2—C19—C20—C14	0.84 (11)
C12—C7—C8—C2	179.74 (9)	C24—C19—C20—C14	179.22 (10)
N1—C7—C8—C9	178.51 (9)	N2—C19—C20—C21	−176.96 (9)
C12—C7—C8—C9	−1.21 (16)	C24—C19—C20—C21	1.42 (16)
C3—C2—C8—C7	−179.98 (10)	C15—C14—C20—C19	179.31 (10)
C1—C2—C8—C7	0.51 (11)	C13—C14—C20—C19	−0.96 (11)
C3—C2—C8—C9	1.06 (18)	C15—C14—C20—C21	−3.11 (18)
C1—C2—C8—C9	−178.45 (10)	C13—C14—C20—C21	176.62 (10)
C7—C8—C9—C10	−11.40 (13)	C19—C20—C21—C22	16.06 (13)
C2—C8—C9—C10	167.41 (10)	C14—C20—C21—C22	−161.18 (10)
C8—C9—C10—C11	42.37 (12)	C20—C21—C22—C23	−46.69 (11)
C9—C10—C11—C12	−63.46 (12)	C21—C22—C23—C24	62.74 (12)
C8—C7—C12—C11	−16.90 (13)	C20—C19—C24—C23	11.84 (15)
N1—C7—C12—C11	163.42 (9)	N2—C19—C24—C23	−170.00 (9)
C10—C11—C12—C7	47.47 (11)	C22—C23—C24—C19	−42.38 (12)