Redetermination of the crystal structure of boron subphthalocyanine chloride (Cl-BsubPc) enabled by slow train sublimation

The crystal structure of boron subphthalocyanine chloride [systematic name: chlorido­(subphthalocyaninato)boron], C₂₄H₁₂BClN₆, a material of widespread inter­est in organic electronic device applications, has been redetermined with a higher precision using large single crystals obtained via slow train sublimation. Details are given for the construction and operation of the train sublimation system, which has been designed to reproducibly yield single crystals suitable for diffraction experiments in a manner which approximates the vacuum deposition conditions commonly used to fabricate organic electronic devices. Diffraction experiments were conducted using two crystal samples and four temperatures (90, 123, 147 and 295 K), enabling a discussion of changes in the unit cell and inter­molecular inter­actions with respect to temperature and in comparison to two previously published structures of Cl-BsubPc. The redetermined structure confirms the original structure published 41 years ago [Meller & Ossko (1972). Monatsh. Chem. 103, 150–155], with significantly improved precision for the geo­metric parameters. Analysis of the crystal structure revealed three inter­secting ribbon motifs formed through a combination of π–π and halogen–π (specifically B—Cl...π) inter­actions. H atoms were refined independently in order to facilitate a thorough discussion of these inter­molecular inter­actions using Hirshfeld surface analysis.

Computing details

For all compounds, data collection: APEX2 (Bruker, 2014); cell refinement: APEX2 (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b). Molecular graphics: PLATON (Spek, 2009), POV-RAY for Windows (Cason, 2004) and Mercury (Macrae et al., 2008) for d13188, d1597, d1596, d1599; PLATON (Spek, 2009) for d1598. For all compounds, software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(d13188) Chlorido(subphthalocyaninato)boron

Crystal data

C24H12BClN6	Dx = 1.560 Mg m^−3
Mr = 430.66	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnma	Cell parameters from 8009 reflections
a = 12.0347 (18) Å	θ = 2.6–27.5°
b = 14.806 (2) Å	µ = 0.24 mm^−1
c = 10.2883 (17) Å	T = 147 K
V = 1833.2 (5) Å^3	Block, purple
Z = 4	0.36 × 0.19 × 0.18 mm
F(000) = 880

Data collection

Bruker Kappa APEX DUO CCD diffractometer	1997 reflections with I > 2σ(I)
Radiation source: sealed tube with Bruker Triumph monochromator	Rint = 0.026
φ and ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −15→15
Tmin = 0.682, Tmax = 0.746	k = −19→18
15856 measured reflections	l = −13→9
2189 independent reflections

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)] = 0.030	Hydrogen site location: difference Fourier map
wR(F^2) = 0.084	All H-atom parameters refined
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0425P)^2 + 1.0469P] where P = (Fo^2 + 2Fc^2)/3
2189 reflections	(Δ/σ)max < 0.001
175 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
Cl1	0.18666 (3)	0.2500	1.23892 (4)	0.01566 (12)
N1	0.00602 (11)	0.2500	0.90628 (14)	0.0137 (3)
N2	0.16170 (8)	0.32919 (6)	0.99213 (10)	0.0126 (2)
N3	0.33415 (8)	0.40651 (7)	0.97337 (10)	0.0146 (2)
N4	0.32883 (11)	0.2500	1.02311 (14)	0.0134 (3)
C1	0.06074 (9)	0.32724 (8)	0.93079 (11)	0.0131 (2)
C2	0.04561 (10)	0.41771 (8)	0.87890 (12)	0.0134 (2)
C3	−0.04140 (10)	0.45721 (8)	0.80988 (12)	0.0159 (2)
H3	−0.1077 (13)	0.4251 (11)	0.7895 (15)	0.020 (4)*
C4	−0.02902 (11)	0.54566 (9)	0.76895 (12)	0.0181 (3)
H4	−0.0891 (14)	0.5722 (12)	0.7206 (16)	0.024 (4)*
C5	0.06884 (10)	0.59402 (9)	0.79406 (13)	0.0181 (3)
H5	0.0743 (13)	0.6569 (12)	0.7650 (15)	0.023 (4)*
C6	0.15803 (10)	0.55468 (8)	0.85781 (12)	0.0162 (2)
H6	0.2258 (13)	0.5885 (11)	0.8743 (15)	0.021 (4)*
C7	0.14593 (10)	0.46614 (8)	0.90108 (12)	0.0138 (2)
C8	0.22259 (10)	0.40493 (8)	0.96551 (11)	0.0134 (2)
C9	0.38567 (10)	0.32727 (8)	0.99394 (11)	0.0144 (2)
C10	0.49861 (10)	0.29813 (8)	0.96487 (11)	0.0154 (3)
C11	0.59457 (10)	0.34633 (9)	0.93370 (12)	0.0193 (3)
H11	0.5940 (13)	0.4132 (11)	0.9329 (15)	0.020 (4)*
C12	0.68940 (10)	0.29737 (10)	0.90464 (14)	0.0232 (3)
H12	0.7583 (14)	0.3285 (11)	0.8847 (17)	0.030 (4)*
B1	0.20973 (15)	0.2500	1.05833 (18)	0.0126 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0216 (2)	0.0128 (2)	0.0126 (2)	0.000	0.00084 (15)	0.000
N1	0.0140 (6)	0.0126 (7)	0.0145 (7)	0.000	0.0018 (5)	0.000
N2	0.0135 (4)	0.0112 (5)	0.0131 (5)	−0.0001 (4)	0.0001 (4)	0.0000 (4)
N3	0.0155 (5)	0.0141 (5)	0.0143 (5)	−0.0011 (4)	−0.0007 (4)	0.0002 (4)
N4	0.0141 (7)	0.0124 (7)	0.0137 (7)	0.000	−0.0007 (5)	0.000
C1	0.0126 (5)	0.0143 (6)	0.0123 (6)	0.0012 (4)	0.0019 (4)	−0.0001 (4)
C2	0.0158 (5)	0.0120 (5)	0.0125 (5)	0.0011 (4)	0.0030 (4)	−0.0013 (4)
C3	0.0154 (5)	0.0168 (6)	0.0154 (6)	0.0016 (4)	0.0000 (4)	−0.0005 (5)
C4	0.0196 (6)	0.0183 (6)	0.0163 (6)	0.0056 (5)	0.0000 (5)	0.0019 (5)
C5	0.0234 (6)	0.0140 (6)	0.0168 (6)	0.0022 (5)	0.0037 (5)	0.0030 (5)
C6	0.0183 (5)	0.0139 (6)	0.0163 (6)	−0.0003 (4)	0.0028 (4)	0.0007 (5)
C7	0.0151 (5)	0.0140 (5)	0.0123 (5)	0.0014 (4)	0.0014 (4)	−0.0002 (4)
C8	0.0168 (5)	0.0119 (5)	0.0117 (5)	−0.0010 (4)	0.0006 (4)	−0.0005 (4)
C9	0.0144 (5)	0.0157 (6)	0.0131 (6)	−0.0027 (4)	−0.0013 (4)	0.0001 (4)
C10	0.0139 (5)	0.0193 (6)	0.0131 (6)	0.0006 (4)	−0.0025 (4)	0.0003 (5)
C11	0.0171 (6)	0.0226 (6)	0.0182 (6)	−0.0034 (5)	−0.0028 (5)	0.0027 (5)
C12	0.0148 (6)	0.0315 (8)	0.0234 (7)	−0.0038 (5)	0.0005 (5)	0.0031 (6)
B1	0.0148 (8)	0.0109 (8)	0.0122 (9)	0.000	−0.0002 (7)	0.000

Geometric parameters (Å, º)

Cl1—B1	1.879 (2)	C4—C5	1.4023 (18)
N1—C1	1.3435 (14)	C4—H4	0.962 (17)
N1—C1^i	1.3436 (14)	C5—C6	1.3861 (17)
N2—C8	1.3673 (15)	C5—H5	0.980 (17)
N2—C1	1.3694 (15)	C6—C7	1.3921 (17)
N2—B1	1.4739 (15)	C6—H6	0.971 (16)
N3—C9	1.3437 (15)	C7—C8	1.4532 (16)
N3—C8	1.3451 (15)	C9—C10	1.4570 (16)
N4—C9	1.3663 (14)	C10—C11	1.3950 (17)
N4—C9^i	1.3663 (14)	C10—C10^i	1.425 (2)
N4—B1	1.478 (2)	C11—C12	1.3847 (19)
C1—C2	1.4535 (16)	C11—H11	0.991 (16)
C2—C3	1.3939 (17)	C12—C12^i	1.403 (3)
C2—C7	1.4225 (16)	C12—H12	0.970 (17)
C3—C4	1.3836 (18)	B1—N2^i	1.4739 (15)
C3—H3	0.952 (16)
C1—N1—C1^i	116.68 (14)	C7—C6—H6	121.1 (9)
C8—N2—C1	113.61 (10)	C6—C7—C2	120.80 (11)
C8—N2—B1	122.33 (11)	C6—C7—C8	131.81 (11)
C1—N2—B1	122.96 (11)	C2—C7—C8	107.32 (10)
C9—N3—C8	117.05 (10)	N3—C8—N2	122.49 (11)
C9—N4—C9^i	113.72 (14)	N3—C8—C7	130.56 (11)
C9—N4—B1	122.63 (7)	N2—C8—C7	105.22 (10)
C9^i—N4—B1	122.63 (7)	N3—C9—N4	122.32 (11)
N1—C1—N2	122.64 (11)	N3—C9—C10	131.04 (11)
N1—C1—C2	130.85 (11)	N4—C9—C10	105.32 (11)
N2—C1—C2	105.13 (10)	C11—C10—C10^i	120.77 (8)
C3—C2—C7	120.52 (11)	C11—C10—C9	131.92 (12)
C3—C2—C1	131.91 (11)	C10^i—C10—C9	107.22 (7)
C7—C2—C1	107.41 (10)	C12—C11—C10	117.66 (12)
C4—C3—C2	118.11 (11)	C12—C11—H11	121.8 (9)
C4—C3—H3	119.7 (10)	C10—C11—H11	120.5 (9)
C2—C3—H3	122.2 (10)	C11—C12—C12^i	121.57 (8)
C3—C4—C5	121.18 (12)	C11—C12—H12	120.1 (10)
C3—C4—H4	117.6 (10)	C12^i—C12—H12	118.3 (10)
C5—C4—H4	121.2 (10)	N2^i—B1—N2	105.39 (14)
C6—C5—C4	121.53 (12)	N2^i—B1—N4	105.48 (10)
C6—C5—H5	119.4 (9)	N2—B1—N4	105.48 (10)
C4—C5—H5	119.1 (9)	N2^i—B1—Cl1	113.52 (9)
C5—C6—C7	117.78 (11)	N2—B1—Cl1	113.52 (9)
C5—C6—H6	121.1 (9)	N4—B1—Cl1	112.68 (12)
C1^i—N1—C1—N2	−7.7 (2)	C2—C7—C8—N3	157.86 (12)
C1^i—N1—C1—C2	156.78 (9)	C6—C7—C8—N2	175.97 (12)
C8—N2—C1—N1	156.43 (12)	C2—C7—C8—N2	−7.04 (13)
B1—N2—C1—N1	−11.83 (19)	C8—N3—C9—N4	−8.59 (18)
C8—N2—C1—C2	−11.48 (13)	C8—N3—C9—C10	156.27 (12)
B1—N2—C1—C2	−179.73 (12)	C9^i—N4—C9—N3	157.04 (9)
N1—C1—C2—C3	15.0 (2)	B1—N4—C9—N3	−11.6 (2)
N2—C1—C2—C3	−178.44 (12)	C9^i—N4—C9—C10	−11.17 (18)
N1—C1—C2—C7	−160.27 (13)	B1—N4—C9—C10	−179.86 (13)
N2—C1—C2—C7	6.24 (13)	N3—C9—C10—C11	16.0 (2)
C7—C2—C3—C4	−2.76 (18)	N4—C9—C10—C11	−177.23 (13)
C1—C2—C3—C4	−177.56 (12)	N3—C9—C10—C10^i	−160.40 (11)
C2—C3—C4—C5	1.03 (18)	N4—C9—C10—C10^i	6.37 (10)
C3—C4—C5—C6	1.7 (2)	C10^i—C10—C11—C12	−0.81 (15)
C4—C5—C6—C7	−2.49 (19)	C9—C10—C11—C12	−176.81 (12)
C5—C6—C7—C2	0.73 (18)	C10—C11—C12—C12^i	0.82 (15)
C5—C6—C7—C8	177.38 (12)	C8—N2—B1—N2^i	−140.44 (10)
C3—C2—C7—C6	1.92 (18)	C1—N2—B1—N2^i	26.8 (2)
C1—C2—C7—C6	177.87 (11)	C8—N2—B1—N4	−29.12 (16)
C3—C2—C7—C8	−175.47 (11)	C1—N2—B1—N4	138.12 (11)
C1—C2—C7—C8	0.48 (13)	C8—N2—B1—Cl1	94.73 (14)
C9—N3—C8—N2	7.61 (17)	C1—N2—B1—Cl1	−98.03 (12)
C9—N3—C8—C7	−155.05 (12)	C9—N4—B1—N2^i	139.47 (12)
C1—N2—C8—N3	−154.65 (11)	C9^i—N4—B1—N2^i	−28.22 (19)
B1—N2—C8—N3	13.69 (18)	C9—N4—B1—N2	28.22 (19)
C1—N2—C8—C7	11.79 (13)	C9^i—N4—B1—N2	−139.47 (12)
B1—N2—C8—C7	−179.88 (12)	C9—N4—B1—Cl1	−96.16 (13)
C6—C7—C8—N3	−19.1 (2)	C9^i—N4—B1—Cl1	96.15 (13)

Symmetry code: (i) x, −y+1/2, z.

(d1597) Chlorido(subphthalocyaninato)boron

Crystal data

C24H12BClN6	Dx = 1.569 Mg m^−3
Mr = 430.66	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnma	Cell parameters from 6209 reflections
a = 12.0156 (13) Å	θ = 2.6–27.5°
b = 14.8099 (16) Å	µ = 0.24 mm^−1
c = 10.2420 (11) Å	T = 90 K
V = 1822.6 (3) Å^3	Plate, purple
Z = 4	0.19 × 0.15 × 0.08 mm
F(000) = 880

Data collection

Bruker Kappa APEX DUO CCD diffractometer	1729 reflections with I > 2σ(I)
Radiation source: sealed tube with Bruker Triumph monochromator	Rint = 0.048
φ and ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −15→15
Tmin = 0.690, Tmax = 0.746	k = −19→19
20761 measured reflections	l = −13→13
2181 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	All H-atom parameters refined
wR(F^2) = 0.082	w = 1/[σ^2(Fo^2) + (0.0334P)^2 + 1.3736P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
2181 reflections	Δρmax = 0.35 e Å^−3
175 parameters	Δρmin = −0.39 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
Cl1	0.18696 (4)	0.2500	1.24001 (5)	0.01312 (13)
N1	0.00591 (14)	0.2500	0.90613 (17)	0.0115 (4)
N2	0.16160 (10)	0.32930 (8)	0.99236 (12)	0.0110 (3)
N3	0.33435 (10)	0.40677 (8)	0.97351 (12)	0.0125 (3)
N4	0.32907 (14)	0.2500	1.02322 (17)	0.0114 (4)
C1	0.06065 (12)	0.32737 (10)	0.93082 (14)	0.0116 (3)
C2	0.04546 (12)	0.41791 (10)	0.87875 (14)	0.0118 (3)
C3	−0.04158 (13)	0.45752 (10)	0.80944 (15)	0.0133 (3)
H3	−0.1082 (14)	0.4255 (11)	0.7872 (16)	0.012 (4)*
C4	−0.02901 (13)	0.54624 (10)	0.76855 (15)	0.0150 (3)
H4	−0.0896 (14)	0.5742 (12)	0.7188 (17)	0.016 (4)*
C5	0.06867 (13)	0.59463 (10)	0.79417 (15)	0.0145 (3)
H5	0.0742 (13)	0.6583 (12)	0.7653 (17)	0.015 (4)*
C6	0.15773 (13)	0.55512 (10)	0.85793 (15)	0.0135 (3)
H6	0.2265 (14)	0.5894 (11)	0.8734 (16)	0.016 (4)*
C7	0.14593 (12)	0.46648 (10)	0.90117 (14)	0.0118 (3)
C8	0.22265 (12)	0.40514 (10)	0.96550 (14)	0.0117 (3)
C9	0.38594 (12)	0.32726 (10)	0.99383 (14)	0.0125 (3)
C10	0.49889 (12)	0.29834 (10)	0.96477 (14)	0.0127 (3)
C11	0.59494 (13)	0.34631 (11)	0.93346 (15)	0.0154 (3)
H11	0.5950 (14)	0.4128 (12)	0.9342 (16)	0.014 (4)*
C12	0.68997 (13)	0.29744 (11)	0.90427 (16)	0.0179 (3)
H12	0.7590 (15)	0.3300 (12)	0.8838 (18)	0.022 (5)*
B1	0.2098 (2)	0.2500	1.0583 (2)	0.0119 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0171 (2)	0.0110 (2)	0.0112 (2)	0.000	0.0007 (2)	0.000
N1	0.0127 (9)	0.0107 (9)	0.0112 (9)	0.000	0.0018 (7)	0.000
N2	0.0116 (6)	0.0095 (6)	0.0118 (6)	−0.0002 (5)	0.0001 (5)	−0.0002 (5)
N3	0.0137 (6)	0.0126 (6)	0.0114 (6)	−0.0001 (5)	−0.0008 (5)	−0.0002 (5)
N4	0.0133 (9)	0.0103 (8)	0.0104 (9)	0.000	−0.0009 (7)	0.000
C1	0.0120 (7)	0.0136 (7)	0.0092 (7)	0.0009 (6)	0.0018 (6)	0.0003 (6)
C2	0.0145 (7)	0.0103 (7)	0.0108 (7)	0.0007 (6)	0.0029 (6)	−0.0011 (5)
C3	0.0132 (7)	0.0148 (7)	0.0119 (7)	0.0004 (6)	0.0006 (6)	−0.0024 (6)
C4	0.0171 (7)	0.0152 (7)	0.0126 (7)	0.0049 (6)	−0.0001 (6)	0.0006 (6)
C5	0.0194 (8)	0.0117 (7)	0.0124 (7)	0.0011 (6)	0.0027 (6)	0.0009 (6)
C6	0.0151 (7)	0.0123 (7)	0.0129 (7)	0.0004 (6)	0.0018 (6)	−0.0009 (6)
C7	0.0130 (7)	0.0123 (7)	0.0102 (7)	0.0004 (6)	0.0018 (6)	−0.0012 (5)
C8	0.0148 (7)	0.0109 (7)	0.0094 (7)	−0.0017 (6)	0.0012 (6)	−0.0004 (5)
C9	0.0132 (7)	0.0137 (7)	0.0106 (7)	−0.0019 (6)	−0.0008 (6)	−0.0003 (6)
C10	0.0139 (7)	0.0149 (7)	0.0092 (7)	0.0006 (6)	−0.0025 (6)	0.0006 (6)
C11	0.0161 (7)	0.0172 (8)	0.0129 (8)	−0.0017 (6)	−0.0019 (6)	0.0015 (6)
C12	0.0141 (7)	0.0238 (8)	0.0158 (8)	−0.0036 (7)	−0.0002 (6)	0.0021 (7)
B1	0.0138 (11)	0.0112 (11)	0.0107 (11)	0.000	0.0009 (9)	0.000

Geometric parameters (Å, º)

Cl1—B1	1.881 (2)	C4—C5	1.400 (2)
N1—C1	1.3452 (17)	C4—H4	0.980 (17)
N1—C1^i	1.3452 (17)	C5—C6	1.383 (2)
N2—C1	1.3674 (18)	C5—H5	0.991 (17)
N2—C8	1.3693 (18)	C6—C7	1.393 (2)
N2—B1	1.4734 (19)	C6—H6	0.983 (17)
N3—C8	1.3449 (19)	C7—C8	1.452 (2)
N3—C9	1.3468 (19)	C9—C10	1.454 (2)
N4—C9^i	1.3663 (17)	C10—C11	1.393 (2)
N4—C9	1.3663 (17)	C10—C10^i	1.432 (3)
N4—B1	1.478 (3)	C11—C12	1.385 (2)
C1—C2	1.454 (2)	C11—H11	0.985 (17)
C2—C3	1.394 (2)	C12—C12^i	1.405 (3)
C2—C7	1.424 (2)	C12—H12	0.982 (18)
C3—C4	1.387 (2)	B1—N2^i	1.4734 (19)
C3—H3	0.958 (17)
C1—N1—C1^i	116.82 (17)	C7—C6—H6	121.4 (10)
C1—N2—C8	113.56 (12)	C6—C7—C2	120.75 (14)
C1—N2—B1	122.91 (13)	C6—C7—C8	132.01 (14)
C8—N2—B1	122.37 (13)	C2—C7—C8	107.17 (12)
C8—N3—C9	116.93 (12)	N3—C8—N2	122.48 (13)
C9^i—N4—C9	113.75 (17)	N3—C8—C7	130.53 (13)
C9^i—N4—B1	122.59 (9)	N2—C8—C7	105.32 (12)
C9—N4—B1	122.59 (9)	N3—C9—N4	122.42 (13)
N1—C1—N2	122.57 (13)	N3—C9—C10	130.96 (14)
N1—C1—C2	130.92 (14)	N4—C9—C10	105.38 (13)
N2—C1—C2	105.13 (12)	C11—C10—C10^i	120.67 (9)
C3—C2—C7	120.38 (13)	C11—C10—C9	132.10 (14)
C3—C2—C1	131.99 (14)	C10^i—C10—C9	107.13 (8)
C7—C2—C1	107.47 (12)	C12—C11—C10	117.80 (15)
C4—C3—C2	118.09 (14)	C12—C11—H11	121.6 (10)
C4—C3—H3	119.2 (10)	C10—C11—H11	120.6 (10)
C2—C3—H3	122.7 (10)	C11—C12—C12^i	121.52 (9)
C3—C4—C5	121.30 (14)	C11—C12—H12	119.1 (10)
C3—C4—H4	118.4 (10)	C12^i—C12—H12	119.4 (10)
C5—C4—H4	120.3 (10)	N2^i—B1—N2	105.71 (17)
C6—C5—C4	121.36 (14)	N2^i—B1—N4	105.63 (13)
C6—C5—H5	119.5 (10)	N2—B1—N4	105.63 (13)
C4—C5—H5	119.2 (10)	N2^i—B1—Cl1	113.35 (11)
C5—C6—C7	118.03 (14)	N2—B1—Cl1	113.35 (11)
C5—C6—H6	120.5 (10)	N4—B1—Cl1	112.47 (15)
C1^i—N1—C1—N2	−7.6 (3)	C2—C7—C8—N3	157.97 (15)
C1^i—N1—C1—C2	156.84 (11)	C6—C7—C8—N2	175.83 (15)
C8—N2—C1—N1	156.35 (15)	C2—C7—C8—N2	−7.24 (16)
B1—N2—C1—N1	−11.6 (2)	C8—N3—C9—N4	−8.9 (2)
C8—N2—C1—C2	−11.56 (16)	C8—N3—C9—C10	156.38 (15)
B1—N2—C1—C2	−179.52 (15)	C9^i—N4—C9—N3	157.21 (10)
N1—C1—C2—C3	15.1 (3)	B1—N4—C9—N3	−11.3 (3)
N2—C1—C2—C3	−178.46 (15)	C9^i—N4—C9—C10	−11.3 (2)
N1—C1—C2—C7	−160.28 (16)	B1—N4—C9—C10	−179.78 (17)
N2—C1—C2—C7	6.20 (15)	N3—C9—C10—C11	15.6 (3)
C7—C2—C3—C4	−2.8 (2)	N4—C9—C10—C11	−177.23 (16)
C1—C2—C3—C4	−177.62 (15)	N3—C9—C10—C10^i	−160.71 (14)
C2—C3—C4—C5	0.9 (2)	N4—C9—C10—C10^i	6.44 (13)
C3—C4—C5—C6	1.9 (2)	C10^i—C10—C11—C12	−0.83 (17)
C4—C5—C6—C7	−2.7 (2)	C9—C10—C11—C12	−176.75 (15)
C5—C6—C7—C2	0.7 (2)	C10—C11—C12—C12^i	0.83 (17)
C5—C6—C7—C8	177.32 (15)	C1—N2—B1—N2^i	26.4 (2)
C3—C2—C7—C6	2.0 (2)	C8—N2—B1—N2^i	−140.47 (12)
C1—C2—C7—C6	177.99 (13)	C1—N2—B1—N4	138.11 (14)
C3—C2—C7—C8	−175.34 (13)	C8—N2—B1—N4	−28.8 (2)
C1—C2—C7—C8	0.65 (16)	C1—N2—B1—Cl1	−98.31 (15)
C9—N3—C8—N2	7.9 (2)	C8—N2—B1—Cl1	94.78 (17)
C9—N3—C8—C7	−155.12 (15)	C9^i—N4—B1—N2^i	−27.9 (2)
C1—N2—C8—N3	−154.72 (14)	C9—N4—B1—N2^i	139.59 (15)
B1—N2—C8—N3	13.3 (2)	C9^i—N4—B1—N2	−139.59 (15)
C1—N2—C8—C7	11.98 (16)	C9—N4—B1—N2	27.9 (2)
B1—N2—C8—C7	−179.98 (14)	C9^i—N4—B1—Cl1	96.27 (16)
C6—C7—C8—N3	−19.0 (3)	C9—N4—B1—Cl1	−96.27 (16)

Symmetry code: (i) x, −y+1/2, z.

(d1596) Chlorido(subphthalocyaninato)boron

Crystal data

C24H12BClN6	Dx = 1.575 Mg m^−3
Mr = 430.66	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnma	Cell parameters from 1240 reflections
a = 11.9993 (15) Å	θ = 2.6–24.7°
b = 14.7761 (14) Å	µ = 0.24 mm^−1
c = 10.2420 (13) Å	T = 123 K
V = 1815.9 (4) Å^3	Plate, purple
Z = 4	0.19 × 0.15 × 0.08 mm
F(000) = 880

Data collection

Bruker Kappa APEX DUO CCD diffractometer	1541 reflections with I > 2σ(I)
Radiation source: sealed tube with Bruker Triumph monochromator	Rint = 0.064
φ and ω scans	θmax = 27.6°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −15→15
Tmin = 0.675, Tmax = 0.746	k = −15→19
8774 measured reflections	l = −13→11
2170 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	All H-atom parameters refined
wR(F^2) = 0.096	w = 1/[σ^2(Fo^2) + (0.0369P)^2 + 0.9339P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
2170 reflections	Δρmax = 0.29 e Å^−3
175 parameters	Δρmin = −0.34 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
Cl1	0.18681 (6)	0.2500	1.23941 (6)	0.01548 (18)
N1	0.0061 (2)	0.2500	0.9062 (2)	0.0131 (5)
N2	0.16158 (14)	0.32929 (10)	0.99219 (15)	0.0123 (4)
N3	0.33393 (14)	0.40664 (11)	0.97365 (15)	0.0142 (4)
N4	0.3289 (2)	0.2500	1.0232 (2)	0.0126 (5)
C1	0.06092 (17)	0.32731 (13)	0.93092 (18)	0.0127 (4)
C2	0.04554 (17)	0.41774 (12)	0.87894 (19)	0.0131 (4)
C3	−0.04120 (19)	0.45758 (14)	0.80987 (19)	0.0153 (4)
H3	−0.108 (2)	0.4248 (15)	0.788 (2)	0.020 (6)*
C4	−0.02895 (19)	0.54590 (14)	0.7688 (2)	0.0175 (4)
H4	−0.0860 (18)	0.5730 (14)	0.721 (2)	0.012 (5)*
C5	0.06896 (19)	0.59408 (14)	0.79404 (19)	0.0177 (5)
H5	0.0743 (17)	0.6584 (14)	0.762 (2)	0.013 (5)*
C6	0.15775 (18)	0.55508 (13)	0.8577 (2)	0.0154 (4)
H6	0.2282 (18)	0.5884 (13)	0.8727 (19)	0.010 (5)*
C7	0.14569 (17)	0.46619 (13)	0.90106 (19)	0.0138 (4)
C8	0.22313 (18)	0.40489 (12)	0.96549 (18)	0.0136 (4)
C9	0.38622 (18)	0.32716 (13)	0.99407 (18)	0.0142 (4)
C10	0.49856 (17)	0.29825 (14)	0.96479 (18)	0.0146 (4)
C11	0.59480 (18)	0.34613 (15)	0.9336 (2)	0.0180 (5)
H11	0.5941 (17)	0.4108 (14)	0.933 (2)	0.010 (5)*
C12	0.68951 (19)	0.29737 (15)	0.9044 (2)	0.0214 (5)
H12	0.757 (2)	0.3302 (15)	0.884 (2)	0.027 (6)*
B1	0.2098 (3)	0.2500	1.0584 (3)	0.0130 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0205 (4)	0.0140 (3)	0.0119 (3)	0.000	0.0007 (3)	0.000
N1	0.0149 (13)	0.0127 (12)	0.0118 (11)	0.000	0.0019 (10)	0.000
N2	0.0133 (9)	0.0109 (8)	0.0127 (8)	−0.0006 (7)	−0.0002 (7)	−0.0002 (6)
N3	0.0137 (9)	0.0158 (9)	0.0131 (8)	−0.0002 (7)	−0.0002 (7)	0.0004 (6)
N4	0.0152 (14)	0.0116 (11)	0.0110 (11)	0.000	0.0007 (9)	0.000
C1	0.0123 (10)	0.0151 (10)	0.0108 (9)	0.0003 (8)	0.0017 (8)	−0.0001 (7)
C2	0.0146 (10)	0.0128 (9)	0.0118 (9)	0.0015 (8)	0.0025 (8)	−0.0008 (7)
C3	0.0152 (11)	0.0171 (10)	0.0135 (10)	0.0008 (9)	0.0011 (8)	−0.0019 (8)
C4	0.0200 (11)	0.0183 (10)	0.0142 (10)	0.0053 (9)	0.0001 (9)	0.0012 (8)
C5	0.0244 (12)	0.0142 (10)	0.0145 (10)	0.0018 (9)	0.0032 (8)	0.0009 (8)
C6	0.0172 (11)	0.0154 (10)	0.0136 (10)	−0.0010 (8)	0.0026 (8)	−0.0011 (8)
C7	0.0156 (11)	0.0147 (10)	0.0109 (9)	0.0014 (8)	0.0018 (8)	−0.0017 (7)
C8	0.0168 (11)	0.0126 (10)	0.0114 (9)	−0.0007 (8)	0.0002 (8)	−0.0004 (7)
C9	0.0158 (11)	0.0159 (10)	0.0108 (9)	−0.0032 (9)	−0.0014 (8)	0.0002 (7)
C10	0.0139 (11)	0.0198 (10)	0.0102 (9)	−0.0003 (8)	−0.0018 (8)	0.0007 (8)
C11	0.0173 (12)	0.0204 (12)	0.0162 (10)	−0.0008 (9)	−0.0028 (8)	0.0017 (9)
C12	0.0148 (11)	0.0295 (11)	0.0198 (11)	−0.0043 (10)	−0.0004 (9)	0.0034 (9)
B1	0.0148 (18)	0.0154 (16)	0.0088 (14)	0.000	0.0002 (12)	0.000

Geometric parameters (Å, º)

Cl1—B1	1.874 (3)	C4—C5	1.398 (3)
N1—C1	1.342 (2)	C4—H4	0.93 (2)
N1—C1^i	1.342 (2)	C5—C6	1.376 (3)
N2—C1	1.361 (3)	C5—H5	1.01 (2)
N2—C8	1.367 (2)	C6—C7	1.394 (3)
N2—B1	1.472 (2)	C6—H6	0.99 (2)
N3—C8	1.332 (3)	C7—C8	1.456 (3)
N3—C9	1.348 (3)	C9—C10	1.446 (3)
N4—C9^i	1.364 (2)	C10—C11	1.391 (3)
N4—C9	1.365 (2)	C10—C10^i	1.426 (4)
N4—B1	1.474 (4)	C11—C12	1.379 (3)
C1—C2	1.450 (3)	C11—H11	0.956 (19)
C2—C3	1.389 (3)	C12—C12^i	1.400 (4)
C2—C7	1.417 (3)	C12—H12	0.97 (3)
C3—C4	1.379 (3)	B1—N2^i	1.472 (2)
C3—H3	0.96 (2)
C1—N1—C1^i	116.6 (2)	C7—C6—H6	120.5 (11)
C1—N2—C8	113.87 (16)	C6—C7—C2	120.87 (19)
C1—N2—B1	122.97 (17)	C6—C7—C8	131.63 (19)
C8—N2—B1	122.01 (18)	C2—C7—C8	107.43 (16)
C8—N3—C9	117.21 (16)	N3—C8—N2	122.85 (17)
C9^i—N4—C9	113.4 (2)	N3—C8—C7	130.79 (18)
C9^i—N4—B1	122.82 (12)	N2—C8—C7	104.74 (17)
C9—N4—B1	122.82 (12)	N3—C9—N4	121.84 (19)
N1—C1—N2	122.69 (17)	N3—C9—C10	131.25 (18)
N1—C1—C2	130.73 (19)	N4—C9—C10	105.56 (17)
N2—C1—C2	105.21 (16)	C11—C10—C10^i	120.56 (12)
C3—C2—C7	120.18 (18)	C11—C10—C9	132.17 (19)
C3—C2—C1	132.27 (19)	C10^i—C10—C9	107.19 (11)
C7—C2—C1	107.39 (17)	C12—C11—C10	117.9 (2)
C4—C3—C2	118.4 (2)	C12—C11—H11	121.8 (13)
C4—C3—H3	119.6 (13)	C10—C11—H11	120.2 (13)
C2—C3—H3	121.9 (13)	C11—C12—C12^i	121.51 (13)
C3—C4—C5	121.0 (2)	C11—C12—H12	118.5 (14)
C3—C4—H4	119.3 (13)	C12^i—C12—H12	120.0 (13)
C5—C4—H4	119.7 (13)	N2^i—B1—N2	105.4 (2)
C6—C5—C4	121.69 (19)	N2^i—B1—N4	105.58 (17)
C6—C5—H5	120.1 (12)	N2—B1—N4	105.58 (17)
C4—C5—H5	118.2 (12)	N2^i—B1—Cl1	113.44 (15)
C5—C6—C7	117.7 (2)	N2—B1—Cl1	113.44 (15)
C5—C6—H6	121.8 (11)	N4—B1—Cl1	112.6 (2)
C1^i—N1—C1—N2	−7.6 (4)	C2—C7—C8—N3	158.1 (2)
C1^i—N1—C1—C2	156.93 (15)	C6—C7—C8—N2	175.9 (2)
C8—N2—C1—N1	156.18 (19)	C2—C7—C8—N2	−7.3 (2)
B1—N2—C1—N1	−11.8 (3)	C8—N3—C9—N4	−8.9 (3)
C8—N2—C1—C2	−11.7 (2)	C8—N3—C9—C10	155.9 (2)
B1—N2—C1—C2	−179.67 (19)	C9^i—N4—C9—N3	157.30 (13)
N1—C1—C2—C3	15.0 (4)	B1—N4—C9—N3	−11.6 (3)
N2—C1—C2—C3	−178.4 (2)	C9^i—N4—C9—C10	−10.9 (3)
N1—C1—C2—C7	−160.3 (2)	B1—N4—C9—C10	−179.7 (2)
N2—C1—C2—C7	6.3 (2)	N3—C9—C10—C11	16.2 (4)
C7—C2—C3—C4	−2.7 (3)	N4—C9—C10—C11	−177.2 (2)
C1—C2—C3—C4	−177.5 (2)	N3—C9—C10—C10^i	−160.37 (18)
C2—C3—C4—C5	1.0 (3)	N4—C9—C10—C10^i	6.22 (16)
C3—C4—C5—C6	1.6 (3)	C10^i—C10—C11—C12	−0.7 (2)
C4—C5—C6—C7	−2.3 (3)	C9—C10—C11—C12	−176.9 (2)
C5—C6—C7—C2	0.6 (3)	C10—C11—C12—C12^i	0.7 (2)
C5—C6—C7—C8	177.1 (2)	C1—N2—B1—N2^i	26.6 (3)
C3—C2—C7—C6	1.9 (3)	C8—N2—B1—N2^i	−140.37 (16)
C1—C2—C7—C6	177.91 (17)	C1—N2—B1—N4	138.09 (19)
C3—C2—C7—C8	−175.33 (17)	C8—N2—B1—N4	−28.9 (3)
C1—C2—C7—C8	0.6 (2)	C1—N2—B1—Cl1	−98.1 (2)
C9—N3—C8—N2	8.0 (3)	C8—N2—B1—Cl1	94.9 (2)
C9—N3—C8—C7	−155.12 (19)	C9^i—N4—B1—N2^i	−28.2 (3)
C1—N2—C8—N3	−154.79 (18)	C9—N4—B1—N2^i	139.60 (19)
B1—N2—C8—N3	13.3 (3)	C9^i—N4—B1—N2	−139.60 (19)
C1—N2—C8—C7	12.1 (2)	C9—N4—B1—N2	28.2 (3)
B1—N2—C8—C7	−179.85 (18)	C9^i—N4—B1—Cl1	96.1 (2)
C6—C7—C8—N3	−18.7 (4)	C9—N4—B1—Cl1	−96.1 (2)

Symmetry code: (i) x, −y+1/2, z.

(d1599) Chlorido(subphthalocyaninato)boron

Crystal data

C24H12BClN6	Dx = 1.567 Mg m^−3
Mr = 430.66	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnma	Cell parameters from 1648 reflections
a = 12.0187 (10) Å	θ = 2.6–23.7°
b = 14.7980 (13) Å	µ = 0.24 mm^−1
c = 10.2632 (8) Å	T = 147 K
V = 1825.3 (3) Å^3	Plate, purple
Z = 4	0.19 × 0.15 × 0.08 mm
F(000) = 880

Data collection

Bruker Kappa APEX DUO CCD diffractometer	1597 reflections with I > 2σ(I)
Radiation source: sealed tube with Bruker Triupmh monochromator	Rint = 0.071
φ and ω scans	θmax = 27.8°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −15→15
Tmin = 0.688, Tmax = 0.746	k = −19→11
12814 measured reflections	l = −9→13
2221 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	All H-atom parameters refined
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.039P)^2 + 0.7856P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
2221 reflections	Δρmax = 0.31 e Å^−3
175 parameters	Δρmin = −0.33 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
Cl1	0.18681 (6)	0.2500	1.23911 (6)	0.01767 (17)
N1	0.00598 (18)	0.2500	0.9064 (2)	0.0151 (5)
N2	0.16156 (12)	0.32914 (10)	0.99203 (14)	0.0139 (3)
N3	0.33402 (13)	0.40656 (10)	0.97343 (14)	0.0160 (4)
N4	0.32865 (18)	0.2500	1.0230 (2)	0.0149 (5)
C1	0.06075 (15)	0.32725 (12)	0.93072 (17)	0.0143 (4)
C2	0.04551 (16)	0.41777 (12)	0.87880 (17)	0.0151 (4)
C3	−0.04118 (17)	0.45752 (13)	0.80993 (18)	0.0172 (4)
H3	−0.1075 (18)	0.4246 (15)	0.790 (2)	0.028 (6)*
C4	−0.02883 (17)	0.54576 (13)	0.76890 (19)	0.0201 (4)
H4	−0.0895 (16)	0.5741 (14)	0.7194 (19)	0.020 (5)*
C5	0.06880 (17)	0.59423 (13)	0.79411 (18)	0.0192 (4)
H5	0.0742 (16)	0.6565 (14)	0.7637 (19)	0.023 (6)*
C6	0.15755 (17)	0.55470 (12)	0.85764 (18)	0.0175 (4)
H6	0.2264 (17)	0.5884 (14)	0.8721 (18)	0.021 (5)*
C7	0.14595 (15)	0.46615 (12)	0.90102 (17)	0.0152 (4)
C8	0.22282 (16)	0.40503 (12)	0.96534 (17)	0.0150 (4)
C9	0.38608 (16)	0.32725 (12)	0.99403 (17)	0.0155 (4)
C10	0.49859 (16)	0.29816 (12)	0.96481 (17)	0.0164 (4)
C11	0.59463 (17)	0.34607 (14)	0.93374 (19)	0.0198 (4)
H11	0.5935 (17)	0.4113 (14)	0.932 (2)	0.022 (6)*
C12	0.68945 (18)	0.29722 (14)	0.90441 (19)	0.0243 (5)
H12	0.7574 (19)	0.3323 (15)	0.881 (2)	0.033 (6)*
B1	0.2096 (3)	0.2500	1.0580 (3)	0.0145 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0241 (4)	0.0145 (3)	0.0144 (3)	0.000	0.0008 (3)	0.000
N1	0.0162 (12)	0.0137 (11)	0.0154 (11)	0.000	0.0019 (9)	0.000
N2	0.0142 (8)	0.0123 (7)	0.0153 (7)	−0.0009 (6)	−0.0003 (6)	0.0001 (6)
N3	0.0159 (9)	0.0167 (8)	0.0155 (8)	−0.0012 (6)	−0.0017 (6)	0.0004 (6)
N4	0.0173 (13)	0.0129 (10)	0.0145 (11)	0.000	−0.0010 (9)	0.000
C1	0.0130 (9)	0.0170 (9)	0.0130 (8)	0.0010 (7)	0.0021 (7)	0.0001 (7)
C2	0.0185 (10)	0.0134 (8)	0.0135 (9)	0.0011 (8)	0.0039 (8)	−0.0010 (7)
C3	0.0176 (11)	0.0171 (9)	0.0170 (10)	0.0014 (8)	0.0005 (8)	−0.0016 (7)
C4	0.0224 (11)	0.0208 (10)	0.0171 (10)	0.0067 (8)	0.0004 (9)	0.0016 (8)
C5	0.0274 (11)	0.0134 (9)	0.0167 (9)	0.0021 (8)	0.0030 (8)	0.0024 (7)
C6	0.0202 (11)	0.0144 (9)	0.0179 (10)	−0.0010 (8)	0.0032 (8)	0.0001 (7)
C7	0.0169 (10)	0.0150 (9)	0.0136 (9)	0.0011 (8)	0.0025 (8)	−0.0005 (7)
C8	0.0186 (10)	0.0121 (9)	0.0144 (9)	−0.0017 (7)	0.0011 (7)	−0.0010 (7)
C9	0.0177 (10)	0.0164 (9)	0.0125 (9)	−0.0038 (8)	−0.0006 (7)	−0.0013 (7)
C10	0.0167 (10)	0.0190 (10)	0.0136 (9)	−0.0005 (7)	−0.0029 (8)	0.0005 (7)
C11	0.0195 (11)	0.0217 (10)	0.0183 (10)	−0.0024 (8)	−0.0020 (8)	0.0015 (8)
C12	0.0177 (11)	0.0323 (11)	0.0231 (10)	−0.0047 (9)	0.0001 (9)	0.0031 (9)
B1	0.0158 (16)	0.0121 (13)	0.0154 (14)	0.000	−0.0010 (12)	0.000

Geometric parameters (Å, º)

Cl1—B1	1.879 (3)	C4—C5	1.399 (3)
N1—C1	1.342 (2)	C4—H4	0.98 (2)
N1—C1^i	1.342 (2)	C5—C6	1.380 (3)
N2—C1	1.366 (2)	C5—H5	0.97 (2)
N2—C8	1.371 (2)	C6—C7	1.391 (3)
N2—B1	1.471 (2)	C6—H6	0.98 (2)
N3—C8	1.339 (2)	C7—C8	1.452 (3)
N3—C9	1.347 (2)	C9—C10	1.451 (3)
N4—C9	1.368 (2)	C10—C11	1.392 (3)
N4—C9^i	1.368 (2)	C10—C10^i	1.425 (4)
N4—B1	1.475 (4)	C11—C12	1.383 (3)
C1—C2	1.453 (2)	C11—H11	0.97 (2)
C2—C3	1.390 (3)	C12—C12^i	1.398 (4)
C2—C7	1.422 (3)	C12—H12	1.00 (2)
C3—C4	1.380 (3)	B1—N2^i	1.471 (2)
C3—H3	0.95 (2)
C1—N1—C1^i	116.7 (2)	C7—C6—H6	121.1 (12)
C1—N2—C8	113.66 (15)	C6—C7—C2	120.54 (17)
C1—N2—B1	122.96 (16)	C6—C7—C8	131.97 (18)
C8—N2—B1	122.25 (17)	C2—C7—C8	107.43 (15)
C8—N3—C9	117.30 (16)	N3—C8—N2	122.51 (16)
C9—N4—C9^i	113.3 (2)	N3—C8—C7	130.75 (17)
C9—N4—B1	122.84 (12)	N2—C8—C7	105.05 (16)
C9^i—N4—B1	122.84 (12)	N3—C9—N4	121.87 (18)
N1—C1—N2	122.56 (17)	N3—C9—C10	131.25 (17)
N1—C1—C2	130.91 (17)	N4—C9—C10	105.51 (17)
N2—C1—C2	105.18 (15)	C11—C10—C10^i	120.63 (11)
C3—C2—C7	120.33 (17)	C11—C10—C9	132.02 (18)
C3—C2—C1	132.16 (18)	C10^i—C10—C9	107.27 (10)
C7—C2—C1	107.36 (16)	C12—C11—C10	117.85 (19)
C4—C3—C2	118.37 (19)	C12—C11—H11	122.0 (13)
C4—C3—H3	120.5 (13)	C10—C11—H11	120.1 (12)
C2—C3—H3	121.1 (13)	C11—C12—C12^i	121.52 (12)
C3—C4—C5	121.25 (19)	C11—C12—H12	117.0 (13)
C3—C4—H4	118.8 (12)	C12^i—C12—H12	121.4 (13)
C5—C4—H4	119.9 (12)	N2—B1—N2^i	105.6 (2)
C6—C5—C4	121.21 (18)	N2—B1—N4	105.60 (16)
C6—C5—H5	120.0 (12)	N2^i—B1—N4	105.60 (16)
C4—C5—H5	118.7 (12)	N2—B1—Cl1	113.46 (14)
C5—C6—C7	118.22 (18)	N2^i—B1—Cl1	113.46 (14)
C5—C6—H6	120.7 (12)	N4—B1—Cl1	112.45 (19)
C1^i—N1—C1—N2	−7.9 (3)	C2—C7—C8—N3	158.00 (18)
C1^i—N1—C1—C2	156.76 (14)	C6—C7—C8—N2	175.92 (19)
C8—N2—C1—N1	156.51 (18)	C2—C7—C8—N2	−7.09 (19)
B1—N2—C1—N1	−11.6 (3)	C8—N3—C9—N4	−8.6 (3)
C8—N2—C1—C2	−11.56 (19)	C8—N3—C9—C10	155.95 (18)
B1—N2—C1—C2	−179.65 (18)	C9^i—N4—C9—N3	157.27 (13)
N1—C1—C2—C3	14.9 (3)	B1—N4—C9—N3	−11.7 (3)
N2—C1—C2—C3	−178.41 (19)	C9^i—N4—C9—C10	−10.7 (3)
N1—C1—C2—C7	−160.4 (2)	B1—N4—C9—C10	−179.7 (2)
N2—C1—C2—C7	6.28 (19)	N3—C9—C10—C11	16.3 (3)
C7—C2—C3—C4	−2.7 (3)	N4—C9—C10—C11	−177.3 (2)
C1—C2—C3—C4	−177.47 (19)	N3—C9—C10—C10^i	−160.27 (17)
C2—C3—C4—C5	0.8 (3)	N4—C9—C10—C10^i	6.15 (15)
C3—C4—C5—C6	1.9 (3)	C10^i—C10—C11—C12	−0.6 (2)
C4—C5—C6—C7	−2.6 (3)	C9—C10—C11—C12	−176.85 (19)
C5—C6—C7—C2	0.7 (3)	C10—C11—C12—C12^i	0.6 (2)
C5—C6—C7—C8	177.37 (19)	C1—N2—B1—N2^i	26.6 (3)
C3—C2—C7—C6	1.9 (3)	C8—N2—B1—N2^i	−140.46 (15)
C1—C2—C7—C6	177.92 (16)	C1—N2—B1—N4	138.19 (17)
C3—C2—C7—C8	−175.46 (16)	C8—N2—B1—N4	−28.9 (2)
C1—C2—C7—C8	0.5 (2)	C1—N2—B1—Cl1	−98.21 (18)
C9—N3—C8—N2	7.8 (3)	C8—N2—B1—Cl1	94.7 (2)
C9—N3—C8—C7	−155.11 (18)	C9—N4—B1—N2	28.2 (3)
C1—N2—C8—N3	−154.76 (17)	C9^i—N4—B1—N2	−139.72 (18)
B1—N2—C8—N3	13.4 (3)	C9—N4—B1—N2^i	139.72 (18)
C1—N2—C8—C7	11.87 (19)	C9^i—N4—B1—N2^i	−28.2 (3)
B1—N2—C8—C7	−179.94 (17)	C9—N4—B1—Cl1	−96.04 (19)
C6—C7—C8—N3	−19.0 (3)	C9^i—N4—B1—Cl1	96.04 (19)

Symmetry code: (i) x, −y+1/2, z.

(d1598) Chlorido(subphthalocyaninato)boron

Crystal data

C24H12BClN6	Dx = 1.535 Mg m^−3
Mr = 430.66	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnma	Cell parameters from 1837 reflections
a = 12.0634 (9) Å	θ = 2.7–25.5°
b = 14.8634 (11) Å	µ = 0.23 mm^−1
c = 10.3901 (6) Å	T = 295 K
V = 1863.0 (2) Å^3	Plate, purple
Z = 4	0.19 × 0.15 × 0.08 mm
F(000) = 880

Data collection

Bruker Kappa APEX DUO CCD diffractometer	1581 reflections with I > 2σ(I)
Radiation source: sealed tube with Bruker Triumph monochromator	Rint = 0.044
φ and ω scans	θmax = 27.4°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −15→15
Tmin = 0.701, Tmax = 0.746	k = −19→11
9199 measured reflections	l = −13→9
2187 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	All H-atom parameters refined
wR(F^2) = 0.096	w = 1/[σ^2(Fo^2) + (0.0407P)^2 + 0.780P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
2187 reflections	Δρmax = 0.29 e Å^−3
175 parameters	Δρmin = −0.30 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
Cl1	0.18599 (6)	0.2500	1.23566 (6)	0.03204 (19)
N1	0.00654 (18)	0.2500	0.9068 (2)	0.0266 (5)
N2	0.16161 (12)	0.32896 (9)	0.99164 (13)	0.0243 (3)
N3	0.33338 (13)	0.40592 (10)	0.97310 (14)	0.0277 (4)
N4	0.32808 (18)	0.2500	1.02278 (19)	0.0258 (5)
C1	0.06145 (15)	0.32705 (11)	0.93108 (16)	0.0243 (4)
C2	0.04625 (15)	0.41714 (11)	0.87931 (16)	0.0258 (4)
C3	−0.04012 (17)	0.45645 (13)	0.81101 (18)	0.0304 (4)
H3	−0.1058 (18)	0.4256 (14)	0.7903 (19)	0.040 (6)*
C4	−0.02736 (19)	0.54419 (13)	0.77054 (19)	0.0357 (5)
H4	−0.0852 (17)	0.5707 (14)	0.7220 (19)	0.037 (6)*
C5	0.06958 (19)	0.59198 (13)	0.79456 (18)	0.0355 (5)
H5	0.0746 (16)	0.6531 (14)	0.7627 (18)	0.035 (5)*
C6	0.15801 (18)	0.55337 (12)	0.85740 (18)	0.0312 (4)
H6	0.2274 (17)	0.5853 (14)	0.8719 (18)	0.039 (6)*
C7	0.14604 (15)	0.46508 (11)	0.90122 (16)	0.0266 (4)
C8	0.22269 (16)	0.40434 (11)	0.96479 (16)	0.0255 (4)
C9	0.38514 (16)	0.32698 (12)	0.99401 (16)	0.0269 (4)
C10	0.49755 (16)	0.29793 (12)	0.96533 (16)	0.0291 (4)
C11	0.59319 (18)	0.34546 (15)	0.93420 (19)	0.0378 (5)
H11	0.5916 (17)	0.4106 (14)	0.9360 (19)	0.039 (6)*
C12	0.68726 (19)	0.29691 (16)	0.9058 (2)	0.0466 (6)
H12	0.755 (2)	0.3298 (16)	0.885 (2)	0.069 (8)*
B1	0.2098 (3)	0.2500	1.0569 (3)	0.0245 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0444 (4)	0.0256 (3)	0.0261 (3)	0.000	0.0019 (3)	0.000
N1	0.0262 (13)	0.0244 (11)	0.0290 (12)	0.000	0.0017 (9)	0.000
N2	0.0252 (9)	0.0204 (7)	0.0273 (7)	−0.0010 (6)	0.0003 (6)	0.0005 (6)
N3	0.0279 (10)	0.0249 (8)	0.0303 (8)	−0.0027 (6)	−0.0023 (6)	0.0000 (6)
N4	0.0263 (13)	0.0240 (10)	0.0270 (11)	0.000	−0.0008 (9)	0.000
C1	0.0239 (10)	0.0241 (8)	0.0249 (9)	0.0010 (7)	0.0030 (7)	−0.0001 (7)
C2	0.0298 (11)	0.0230 (8)	0.0245 (9)	0.0026 (8)	0.0041 (7)	−0.0007 (7)
C3	0.0282 (11)	0.0317 (10)	0.0312 (10)	0.0042 (8)	0.0001 (8)	−0.0006 (8)
C4	0.0384 (12)	0.0343 (10)	0.0345 (11)	0.0104 (9)	−0.0017 (9)	0.0074 (8)
C5	0.0461 (13)	0.0254 (9)	0.0351 (11)	0.0037 (9)	0.0053 (9)	0.0084 (8)
C6	0.0361 (12)	0.0244 (9)	0.0330 (10)	−0.0006 (8)	0.0050 (8)	0.0035 (7)
C7	0.0302 (11)	0.0234 (9)	0.0263 (9)	0.0015 (8)	0.0036 (8)	−0.0004 (7)
C8	0.0283 (11)	0.0215 (8)	0.0267 (9)	−0.0027 (7)	−0.0002 (7)	0.0002 (7)
C9	0.0260 (11)	0.0269 (9)	0.0279 (9)	−0.0043 (8)	−0.0030 (7)	0.0010 (7)
C10	0.0237 (10)	0.0368 (10)	0.0267 (9)	−0.0020 (8)	−0.0045 (8)	0.0014 (8)
C11	0.0312 (12)	0.0425 (12)	0.0397 (11)	−0.0054 (9)	−0.0042 (9)	0.0044 (9)
C12	0.0271 (12)	0.0602 (14)	0.0524 (13)	−0.0064 (11)	0.0023 (10)	0.0054 (11)
B1	0.0259 (17)	0.0218 (13)	0.0260 (14)	0.000	0.0003 (12)	0.000

Geometric parameters (Å, º)

Cl1—B1	1.880 (3)	C4—C5	1.391 (3)
N1—C1^i	1.347 (2)	C4—H4	0.95 (2)
N1—C1	1.347 (2)	C5—C6	1.376 (3)
N2—C1	1.363 (2)	C5—H5	0.97 (2)
N2—C8	1.370 (2)	C6—C7	1.397 (2)
N2—B1	1.474 (2)	C6—H6	0.97 (2)
N3—C8	1.338 (2)	C7—C8	1.451 (2)
N3—C9	1.347 (2)	C9—C10	1.454 (3)
N4—C9^i	1.368 (2)	C10—C11	1.391 (3)
N4—C9	1.368 (2)	C10—C10^i	1.425 (4)
N4—B1	1.471 (4)	C11—C12	1.377 (3)
C1—C2	1.455 (2)	C11—H11	0.97 (2)
C2—C3	1.389 (3)	C12—C12^i	1.395 (5)
C2—C7	1.417 (2)	C12—H12	0.97 (3)
C3—C4	1.379 (3)	B1—N2^i	1.474 (2)
C3—H3	0.94 (2)
C1^i—N1—C1	116.5 (2)	C7—C6—H6	119.8 (12)
C1—N2—C8	113.58 (14)	C6—C7—C2	120.53 (17)
C1—N2—B1	123.03 (16)	C6—C7—C8	131.84 (18)
C8—N2—B1	122.20 (17)	C2—C7—C8	107.55 (15)
C8—N3—C9	117.24 (15)	N3—C8—N2	122.54 (16)
C9^i—N4—C9	113.5 (2)	N3—C8—C7	130.86 (16)
C9^i—N4—B1	122.74 (11)	N2—C8—C7	105.00 (15)
C9—N4—B1	122.74 (11)	N3—C9—N4	122.04 (17)
N1—C1—N2	122.70 (16)	N3—C9—C10	131.15 (17)
N1—C1—C2	130.66 (17)	N4—C9—C10	105.41 (16)
N2—C1—C2	105.27 (15)	C11—C10—C10^i	120.52 (12)
C3—C2—C7	120.50 (16)	C11—C10—C9	132.10 (18)
C3—C2—C1	132.10 (18)	C10^i—C10—C9	107.28 (10)
C7—C2—C1	107.24 (15)	C12—C11—C10	117.9 (2)
C4—C3—C2	118.02 (19)	C12—C11—H11	123.0 (13)
C4—C3—H3	119.1 (13)	C10—C11—H11	119.1 (13)
C2—C3—H3	122.9 (13)	C11—C12—C12^i	121.60 (14)
C3—C4—C5	121.48 (19)	C11—C12—H12	118.2 (15)
C3—C4—H4	118.2 (13)	C12^i—C12—H12	120.2 (15)
C5—C4—H4	120.2 (12)	N4—B1—N2	105.77 (15)
C6—C5—C4	121.59 (18)	N4—B1—N2^i	105.77 (15)
C6—C5—H5	120.3 (12)	N2—B1—N2^i	105.5 (2)
C4—C5—H5	118.1 (12)	N4—B1—Cl1	112.70 (19)
C5—C6—C7	117.80 (19)	N2—B1—Cl1	113.21 (13)
C5—C6—H6	122.4 (12)	N2^i—B1—Cl1	113.21 (13)
C1^i—N1—C1—N2	−7.9 (3)	C2—C7—C8—N3	158.17 (18)
C1^i—N1—C1—C2	156.64 (13)	C6—C7—C8—N2	176.21 (18)
C8—N2—C1—N1	156.25 (17)	C2—C7—C8—N2	−7.31 (18)
B1—N2—C1—N1	−11.4 (3)	C8—N3—C9—N4	−8.5 (3)
C8—N2—C1—C2	−11.68 (19)	C8—N3—C9—C10	155.86 (18)
B1—N2—C1—C2	−179.38 (17)	C9^i—N4—C9—N3	156.90 (12)
N1—C1—C2—C3	15.0 (3)	B1—N4—C9—N3	−11.7 (3)
N2—C1—C2—C3	−178.42 (18)	C9^i—N4—C9—C10	−11.0 (3)
N1—C1—C2—C7	−160.32 (19)	B1—N4—C9—C10	−179.61 (19)
N2—C1—C2—C7	6.26 (18)	N3—C9—C10—C11	16.2 (3)
C7—C2—C3—C4	−2.7 (3)	N4—C9—C10—C11	−177.5 (2)
C1—C2—C3—C4	−177.54 (18)	N3—C9—C10—C10^i	−160.04 (16)
C2—C3—C4—C5	1.3 (3)	N4—C9—C10—C10^i	6.27 (15)
C3—C4—C5—C6	1.4 (3)	C10^i—C10—C11—C12	−1.0 (2)
C4—C5—C6—C7	−2.4 (3)	C9—C10—C11—C12	−176.82 (19)
C5—C6—C7—C2	0.9 (3)	C10—C11—C12—C12^i	1.0 (2)
C5—C6—C7—C8	177.05 (18)	C9^i—N4—B1—N2	−139.60 (17)
C3—C2—C7—C6	1.7 (3)	C9—N4—B1—N2	28.0 (3)
C1—C2—C7—C6	177.63 (16)	C9^i—N4—B1—N2^i	−28.0 (3)
C3—C2—C7—C8	−175.29 (16)	C9—N4—B1—N2^i	139.60 (17)
C1—C2—C7—C8	0.67 (19)	C9^i—N4—B1—Cl1	96.20 (19)
C9—N3—C8—N2	7.9 (2)	C9—N4—B1—Cl1	−96.20 (19)
C9—N3—C8—C7	−155.38 (17)	C1—N2—B1—N4	138.19 (17)
C1—N2—C8—N3	−154.92 (16)	C8—N2—B1—N4	−28.5 (2)
B1—N2—C8—N3	12.9 (3)	C1—N2—B1—N2^i	26.4 (3)
C1—N2—C8—C7	12.07 (19)	C8—N2—B1—N2^i	−140.27 (15)
B1—N2—C8—C7	179.89 (16)	C1—N2—B1—Cl1	−97.93 (18)
C6—C7—C8—N3	−18.3 (3)	C8—N2—B1—Cl1	95.4 (2)

Symmetry code: (i) x, −y+1/2, z.