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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616003491/fm3033sup1.cif
Contains datablocks d13188, d1597, d1596, d1599, d1598, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616003491/fm3033d13188sup2.hkl
Contains datablock d13188

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616003491/fm3033d1597sup3.hkl
Contains datablock d1597

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616003491/fm3033d1596sup4.hkl
Contains datablock d1596

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616003491/fm3033d1599sup5.hkl
Contains datablock d1599

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616003491/fm3033d1598sup6.hkl
Contains datablock d1598

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229616003491/fm3033sup7.pdf
Displacement ellipsoid plots for Crystal 2 at 90, 123, 147 and 295 K

CCDC references: 1414468; 1414467; 1414466; 1414465; 1052234

Computing details top

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 top
Crystal data top
C24H12BClN6Dx = 1.560 Mg m3
Mr = 430.66Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PnmaCell parameters from 8009 reflections
a = 12.0347 (18) Åθ = 2.6–27.5°
b = 14.806 (2) ŵ = 0.24 mm1
c = 10.2883 (17) ÅT = 147 K
V = 1833.2 (5) Å3Block, purple
Z = 40.36 × 0.19 × 0.18 mm
F(000) = 880
Data collection top
Bruker Kappa APEX DUO CCD
diffractometer
1997 reflections with I > 2σ(I)
Radiation source: sealed tube with Bruker Triumph monochromatorRint = 0.026
φ and ω scansθmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
h = 1515
Tmin = 0.682, Tmax = 0.746k = 1918
15856 measured reflectionsl = 139
2189 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: difference Fourier map
wR(F2) = 0.084All H-atom parameters refined
S = 1.06 w = 1/[σ2(Fo2) + (0.0425P)2 + 1.0469P]
where P = (Fo2 + 2Fc2)/3
2189 reflections(Δ/σ)max < 0.001
175 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.33 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cl10.18666 (3)0.25001.23892 (4)0.01566 (12)
N10.00602 (11)0.25000.90628 (14)0.0137 (3)
N20.16170 (8)0.32919 (6)0.99213 (10)0.0126 (2)
N30.33415 (8)0.40651 (7)0.97337 (10)0.0146 (2)
N40.32883 (11)0.25001.02311 (14)0.0134 (3)
C10.06074 (9)0.32724 (8)0.93079 (11)0.0131 (2)
C20.04561 (10)0.41771 (8)0.87890 (12)0.0134 (2)
C30.04140 (10)0.45721 (8)0.80988 (12)0.0159 (2)
H30.1077 (13)0.4251 (11)0.7895 (15)0.020 (4)*
C40.02902 (11)0.54566 (9)0.76895 (12)0.0181 (3)
H40.0891 (14)0.5722 (12)0.7206 (16)0.024 (4)*
C50.06884 (10)0.59402 (9)0.79406 (13)0.0181 (3)
H50.0743 (13)0.6569 (12)0.7650 (15)0.023 (4)*
C60.15803 (10)0.55468 (8)0.85781 (12)0.0162 (2)
H60.2258 (13)0.5885 (11)0.8743 (15)0.021 (4)*
C70.14593 (10)0.46614 (8)0.90108 (12)0.0138 (2)
C80.22259 (10)0.40493 (8)0.96551 (11)0.0134 (2)
C90.38567 (10)0.32727 (8)0.99394 (11)0.0144 (2)
C100.49861 (10)0.29813 (8)0.96487 (11)0.0154 (3)
C110.59457 (10)0.34633 (9)0.93370 (12)0.0193 (3)
H110.5940 (13)0.4132 (11)0.9329 (15)0.020 (4)*
C120.68940 (10)0.29737 (10)0.90464 (14)0.0232 (3)
H120.7583 (14)0.3285 (11)0.8847 (17)0.030 (4)*
B10.20973 (15)0.25001.05833 (18)0.0126 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0216 (2)0.0128 (2)0.0126 (2)0.0000.00084 (15)0.000
N10.0140 (6)0.0126 (7)0.0145 (7)0.0000.0018 (5)0.000
N20.0135 (4)0.0112 (5)0.0131 (5)0.0001 (4)0.0001 (4)0.0000 (4)
N30.0155 (5)0.0141 (5)0.0143 (5)0.0011 (4)0.0007 (4)0.0002 (4)
N40.0141 (7)0.0124 (7)0.0137 (7)0.0000.0007 (5)0.000
C10.0126 (5)0.0143 (6)0.0123 (6)0.0012 (4)0.0019 (4)0.0001 (4)
C20.0158 (5)0.0120 (5)0.0125 (5)0.0011 (4)0.0030 (4)0.0013 (4)
C30.0154 (5)0.0168 (6)0.0154 (6)0.0016 (4)0.0000 (4)0.0005 (5)
C40.0196 (6)0.0183 (6)0.0163 (6)0.0056 (5)0.0000 (5)0.0019 (5)
C50.0234 (6)0.0140 (6)0.0168 (6)0.0022 (5)0.0037 (5)0.0030 (5)
C60.0183 (5)0.0139 (6)0.0163 (6)0.0003 (4)0.0028 (4)0.0007 (5)
C70.0151 (5)0.0140 (5)0.0123 (5)0.0014 (4)0.0014 (4)0.0002 (4)
C80.0168 (5)0.0119 (5)0.0117 (5)0.0010 (4)0.0006 (4)0.0005 (4)
C90.0144 (5)0.0157 (6)0.0131 (6)0.0027 (4)0.0013 (4)0.0001 (4)
C100.0139 (5)0.0193 (6)0.0131 (6)0.0006 (4)0.0025 (4)0.0003 (5)
C110.0171 (6)0.0226 (6)0.0182 (6)0.0034 (5)0.0028 (5)0.0027 (5)
C120.0148 (6)0.0315 (8)0.0234 (7)0.0038 (5)0.0005 (5)0.0031 (6)
B10.0148 (8)0.0109 (8)0.0122 (9)0.0000.0002 (7)0.000
Geometric parameters (Å, º) top
Cl1—B11.879 (2)C4—C51.4023 (18)
N1—C11.3435 (14)C4—H40.962 (17)
N1—C1i1.3436 (14)C5—C61.3861 (17)
N2—C81.3673 (15)C5—H50.980 (17)
N2—C11.3694 (15)C6—C71.3921 (17)
N2—B11.4739 (15)C6—H60.971 (16)
N3—C91.3437 (15)C7—C81.4532 (16)
N3—C81.3451 (15)C9—C101.4570 (16)
N4—C91.3663 (14)C10—C111.3950 (17)
N4—C9i1.3663 (14)C10—C10i1.425 (2)
N4—B11.478 (2)C11—C121.3847 (19)
C1—C21.4535 (16)C11—H110.991 (16)
C2—C31.3939 (17)C12—C12i1.403 (3)
C2—C71.4225 (16)C12—H120.970 (17)
C3—C41.3836 (18)B1—N2i1.4739 (15)
C3—H30.952 (16)
C1—N1—C1i116.68 (14)C7—C6—H6121.1 (9)
C8—N2—C1113.61 (10)C6—C7—C2120.80 (11)
C8—N2—B1122.33 (11)C6—C7—C8131.81 (11)
C1—N2—B1122.96 (11)C2—C7—C8107.32 (10)
C9—N3—C8117.05 (10)N3—C8—N2122.49 (11)
C9—N4—C9i113.72 (14)N3—C8—C7130.56 (11)
C9—N4—B1122.63 (7)N2—C8—C7105.22 (10)
C9i—N4—B1122.63 (7)N3—C9—N4122.32 (11)
N1—C1—N2122.64 (11)N3—C9—C10131.04 (11)
N1—C1—C2130.85 (11)N4—C9—C10105.32 (11)
N2—C1—C2105.13 (10)C11—C10—C10i120.77 (8)
C3—C2—C7120.52 (11)C11—C10—C9131.92 (12)
C3—C2—C1131.91 (11)C10i—C10—C9107.22 (7)
C7—C2—C1107.41 (10)C12—C11—C10117.66 (12)
C4—C3—C2118.11 (11)C12—C11—H11121.8 (9)
C4—C3—H3119.7 (10)C10—C11—H11120.5 (9)
C2—C3—H3122.2 (10)C11—C12—C12i121.57 (8)
C3—C4—C5121.18 (12)C11—C12—H12120.1 (10)
C3—C4—H4117.6 (10)C12i—C12—H12118.3 (10)
C5—C4—H4121.2 (10)N2i—B1—N2105.39 (14)
C6—C5—C4121.53 (12)N2i—B1—N4105.48 (10)
C6—C5—H5119.4 (9)N2—B1—N4105.48 (10)
C4—C5—H5119.1 (9)N2i—B1—Cl1113.52 (9)
C5—C6—C7117.78 (11)N2—B1—Cl1113.52 (9)
C5—C6—H6121.1 (9)N4—B1—Cl1112.68 (12)
C1i—N1—C1—N27.7 (2)C2—C7—C8—N3157.86 (12)
C1i—N1—C1—C2156.78 (9)C6—C7—C8—N2175.97 (12)
C8—N2—C1—N1156.43 (12)C2—C7—C8—N27.04 (13)
B1—N2—C1—N111.83 (19)C8—N3—C9—N48.59 (18)
C8—N2—C1—C211.48 (13)C8—N3—C9—C10156.27 (12)
B1—N2—C1—C2179.73 (12)C9i—N4—C9—N3157.04 (9)
N1—C1—C2—C315.0 (2)B1—N4—C9—N311.6 (2)
N2—C1—C2—C3178.44 (12)C9i—N4—C9—C1011.17 (18)
N1—C1—C2—C7160.27 (13)B1—N4—C9—C10179.86 (13)
N2—C1—C2—C76.24 (13)N3—C9—C10—C1116.0 (2)
C7—C2—C3—C42.76 (18)N4—C9—C10—C11177.23 (13)
C1—C2—C3—C4177.56 (12)N3—C9—C10—C10i160.40 (11)
C2—C3—C4—C51.03 (18)N4—C9—C10—C10i6.37 (10)
C3—C4—C5—C61.7 (2)C10i—C10—C11—C120.81 (15)
C4—C5—C6—C72.49 (19)C9—C10—C11—C12176.81 (12)
C5—C6—C7—C20.73 (18)C10—C11—C12—C12i0.82 (15)
C5—C6—C7—C8177.38 (12)C8—N2—B1—N2i140.44 (10)
C3—C2—C7—C61.92 (18)C1—N2—B1—N2i26.8 (2)
C1—C2—C7—C6177.87 (11)C8—N2—B1—N429.12 (16)
C3—C2—C7—C8175.47 (11)C1—N2—B1—N4138.12 (11)
C1—C2—C7—C80.48 (13)C8—N2—B1—Cl194.73 (14)
C9—N3—C8—N27.61 (17)C1—N2—B1—Cl198.03 (12)
C9—N3—C8—C7155.05 (12)C9—N4—B1—N2i139.47 (12)
C1—N2—C8—N3154.65 (11)C9i—N4—B1—N2i28.22 (19)
B1—N2—C8—N313.69 (18)C9—N4—B1—N228.22 (19)
C1—N2—C8—C711.79 (13)C9i—N4—B1—N2139.47 (12)
B1—N2—C8—C7179.88 (12)C9—N4—B1—Cl196.16 (13)
C6—C7—C8—N319.1 (2)C9i—N4—B1—Cl196.15 (13)
Symmetry code: (i) x, y+1/2, z.
(d1597) Chlorido(subphthalocyaninato)boron top
Crystal data top
C24H12BClN6Dx = 1.569 Mg m3
Mr = 430.66Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PnmaCell parameters from 6209 reflections
a = 12.0156 (13) Åθ = 2.6–27.5°
b = 14.8099 (16) ŵ = 0.24 mm1
c = 10.2420 (11) ÅT = 90 K
V = 1822.6 (3) Å3Plate, purple
Z = 40.19 × 0.15 × 0.08 mm
F(000) = 880
Data collection top
Bruker Kappa APEX DUO CCD
diffractometer
1729 reflections with I > 2σ(I)
Radiation source: sealed tube with Bruker Triumph monochromatorRint = 0.048
φ and ω scansθmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
h = 1515
Tmin = 0.690, Tmax = 0.746k = 1919
20761 measured reflectionsl = 1313
2181 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032All H-atom parameters refined
wR(F2) = 0.082 w = 1/[σ2(Fo2) + (0.0334P)2 + 1.3736P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
2181 reflectionsΔρmax = 0.35 e Å3
175 parametersΔρmin = 0.39 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cl10.18696 (4)0.25001.24001 (5)0.01312 (13)
N10.00591 (14)0.25000.90613 (17)0.0115 (4)
N20.16160 (10)0.32930 (8)0.99236 (12)0.0110 (3)
N30.33435 (10)0.40677 (8)0.97351 (12)0.0125 (3)
N40.32907 (14)0.25001.02322 (17)0.0114 (4)
C10.06065 (12)0.32737 (10)0.93082 (14)0.0116 (3)
C20.04546 (12)0.41791 (10)0.87875 (14)0.0118 (3)
C30.04158 (13)0.45752 (10)0.80944 (15)0.0133 (3)
H30.1082 (14)0.4255 (11)0.7872 (16)0.012 (4)*
C40.02901 (13)0.54624 (10)0.76855 (15)0.0150 (3)
H40.0896 (14)0.5742 (12)0.7188 (17)0.016 (4)*
C50.06867 (13)0.59463 (10)0.79417 (15)0.0145 (3)
H50.0742 (13)0.6583 (12)0.7653 (17)0.015 (4)*
C60.15773 (13)0.55512 (10)0.85793 (15)0.0135 (3)
H60.2265 (14)0.5894 (11)0.8734 (16)0.016 (4)*
C70.14593 (12)0.46648 (10)0.90117 (14)0.0118 (3)
C80.22265 (12)0.40514 (10)0.96550 (14)0.0117 (3)
C90.38594 (12)0.32726 (10)0.99383 (14)0.0125 (3)
C100.49889 (12)0.29834 (10)0.96477 (14)0.0127 (3)
C110.59494 (13)0.34631 (11)0.93346 (15)0.0154 (3)
H110.5950 (14)0.4128 (12)0.9342 (16)0.014 (4)*
C120.68997 (13)0.29744 (11)0.90427 (16)0.0179 (3)
H120.7590 (15)0.3300 (12)0.8838 (18)0.022 (5)*
B10.2098 (2)0.25001.0583 (2)0.0119 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0171 (2)0.0110 (2)0.0112 (2)0.0000.0007 (2)0.000
N10.0127 (9)0.0107 (9)0.0112 (9)0.0000.0018 (7)0.000
N20.0116 (6)0.0095 (6)0.0118 (6)0.0002 (5)0.0001 (5)0.0002 (5)
N30.0137 (6)0.0126 (6)0.0114 (6)0.0001 (5)0.0008 (5)0.0002 (5)
N40.0133 (9)0.0103 (8)0.0104 (9)0.0000.0009 (7)0.000
C10.0120 (7)0.0136 (7)0.0092 (7)0.0009 (6)0.0018 (6)0.0003 (6)
C20.0145 (7)0.0103 (7)0.0108 (7)0.0007 (6)0.0029 (6)0.0011 (5)
C30.0132 (7)0.0148 (7)0.0119 (7)0.0004 (6)0.0006 (6)0.0024 (6)
C40.0171 (7)0.0152 (7)0.0126 (7)0.0049 (6)0.0001 (6)0.0006 (6)
C50.0194 (8)0.0117 (7)0.0124 (7)0.0011 (6)0.0027 (6)0.0009 (6)
C60.0151 (7)0.0123 (7)0.0129 (7)0.0004 (6)0.0018 (6)0.0009 (6)
C70.0130 (7)0.0123 (7)0.0102 (7)0.0004 (6)0.0018 (6)0.0012 (5)
C80.0148 (7)0.0109 (7)0.0094 (7)0.0017 (6)0.0012 (6)0.0004 (5)
C90.0132 (7)0.0137 (7)0.0106 (7)0.0019 (6)0.0008 (6)0.0003 (6)
C100.0139 (7)0.0149 (7)0.0092 (7)0.0006 (6)0.0025 (6)0.0006 (6)
C110.0161 (7)0.0172 (8)0.0129 (8)0.0017 (6)0.0019 (6)0.0015 (6)
C120.0141 (7)0.0238 (8)0.0158 (8)0.0036 (7)0.0002 (6)0.0021 (7)
B10.0138 (11)0.0112 (11)0.0107 (11)0.0000.0009 (9)0.000
Geometric parameters (Å, º) top
Cl1—B11.881 (2)C4—C51.400 (2)
N1—C11.3452 (17)C4—H40.980 (17)
N1—C1i1.3452 (17)C5—C61.383 (2)
N2—C11.3674 (18)C5—H50.991 (17)
N2—C81.3693 (18)C6—C71.393 (2)
N2—B11.4734 (19)C6—H60.983 (17)
N3—C81.3449 (19)C7—C81.452 (2)
N3—C91.3468 (19)C9—C101.454 (2)
N4—C9i1.3663 (17)C10—C111.393 (2)
N4—C91.3663 (17)C10—C10i1.432 (3)
N4—B11.478 (3)C11—C121.385 (2)
C1—C21.454 (2)C11—H110.985 (17)
C2—C31.394 (2)C12—C12i1.405 (3)
C2—C71.424 (2)C12—H120.982 (18)
C3—C41.387 (2)B1—N2i1.4734 (19)
C3—H30.958 (17)
C1—N1—C1i116.82 (17)C7—C6—H6121.4 (10)
C1—N2—C8113.56 (12)C6—C7—C2120.75 (14)
C1—N2—B1122.91 (13)C6—C7—C8132.01 (14)
C8—N2—B1122.37 (13)C2—C7—C8107.17 (12)
C8—N3—C9116.93 (12)N3—C8—N2122.48 (13)
C9i—N4—C9113.75 (17)N3—C8—C7130.53 (13)
C9i—N4—B1122.59 (9)N2—C8—C7105.32 (12)
C9—N4—B1122.59 (9)N3—C9—N4122.42 (13)
N1—C1—N2122.57 (13)N3—C9—C10130.96 (14)
N1—C1—C2130.92 (14)N4—C9—C10105.38 (13)
N2—C1—C2105.13 (12)C11—C10—C10i120.67 (9)
C3—C2—C7120.38 (13)C11—C10—C9132.10 (14)
C3—C2—C1131.99 (14)C10i—C10—C9107.13 (8)
C7—C2—C1107.47 (12)C12—C11—C10117.80 (15)
C4—C3—C2118.09 (14)C12—C11—H11121.6 (10)
C4—C3—H3119.2 (10)C10—C11—H11120.6 (10)
C2—C3—H3122.7 (10)C11—C12—C12i121.52 (9)
C3—C4—C5121.30 (14)C11—C12—H12119.1 (10)
C3—C4—H4118.4 (10)C12i—C12—H12119.4 (10)
C5—C4—H4120.3 (10)N2i—B1—N2105.71 (17)
C6—C5—C4121.36 (14)N2i—B1—N4105.63 (13)
C6—C5—H5119.5 (10)N2—B1—N4105.63 (13)
C4—C5—H5119.2 (10)N2i—B1—Cl1113.35 (11)
C5—C6—C7118.03 (14)N2—B1—Cl1113.35 (11)
C5—C6—H6120.5 (10)N4—B1—Cl1112.47 (15)
C1i—N1—C1—N27.6 (3)C2—C7—C8—N3157.97 (15)
C1i—N1—C1—C2156.84 (11)C6—C7—C8—N2175.83 (15)
C8—N2—C1—N1156.35 (15)C2—C7—C8—N27.24 (16)
B1—N2—C1—N111.6 (2)C8—N3—C9—N48.9 (2)
C8—N2—C1—C211.56 (16)C8—N3—C9—C10156.38 (15)
B1—N2—C1—C2179.52 (15)C9i—N4—C9—N3157.21 (10)
N1—C1—C2—C315.1 (3)B1—N4—C9—N311.3 (3)
N2—C1—C2—C3178.46 (15)C9i—N4—C9—C1011.3 (2)
N1—C1—C2—C7160.28 (16)B1—N4—C9—C10179.78 (17)
N2—C1—C2—C76.20 (15)N3—C9—C10—C1115.6 (3)
C7—C2—C3—C42.8 (2)N4—C9—C10—C11177.23 (16)
C1—C2—C3—C4177.62 (15)N3—C9—C10—C10i160.71 (14)
C2—C3—C4—C50.9 (2)N4—C9—C10—C10i6.44 (13)
C3—C4—C5—C61.9 (2)C10i—C10—C11—C120.83 (17)
C4—C5—C6—C72.7 (2)C9—C10—C11—C12176.75 (15)
C5—C6—C7—C20.7 (2)C10—C11—C12—C12i0.83 (17)
C5—C6—C7—C8177.32 (15)C1—N2—B1—N2i26.4 (2)
C3—C2—C7—C62.0 (2)C8—N2—B1—N2i140.47 (12)
C1—C2—C7—C6177.99 (13)C1—N2—B1—N4138.11 (14)
C3—C2—C7—C8175.34 (13)C8—N2—B1—N428.8 (2)
C1—C2—C7—C80.65 (16)C1—N2—B1—Cl198.31 (15)
C9—N3—C8—N27.9 (2)C8—N2—B1—Cl194.78 (17)
C9—N3—C8—C7155.12 (15)C9i—N4—B1—N2i27.9 (2)
C1—N2—C8—N3154.72 (14)C9—N4—B1—N2i139.59 (15)
B1—N2—C8—N313.3 (2)C9i—N4—B1—N2139.59 (15)
C1—N2—C8—C711.98 (16)C9—N4—B1—N227.9 (2)
B1—N2—C8—C7179.98 (14)C9i—N4—B1—Cl196.27 (16)
C6—C7—C8—N319.0 (3)C9—N4—B1—Cl196.27 (16)
Symmetry code: (i) x, y+1/2, z.
(d1596) Chlorido(subphthalocyaninato)boron top
Crystal data top
C24H12BClN6Dx = 1.575 Mg m3
Mr = 430.66Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PnmaCell parameters from 1240 reflections
a = 11.9993 (15) Åθ = 2.6–24.7°
b = 14.7761 (14) ŵ = 0.24 mm1
c = 10.2420 (13) ÅT = 123 K
V = 1815.9 (4) Å3Plate, purple
Z = 40.19 × 0.15 × 0.08 mm
F(000) = 880
Data collection top
Bruker Kappa APEX DUO CCD
diffractometer
1541 reflections with I > 2σ(I)
Radiation source: sealed tube with Bruker Triumph monochromatorRint = 0.064
φ and ω scansθmax = 27.6°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
h = 1515
Tmin = 0.675, Tmax = 0.746k = 1519
8774 measured reflectionsl = 1311
2170 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043All H-atom parameters refined
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.0369P)2 + 0.9339P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
2170 reflectionsΔρmax = 0.29 e Å3
175 parametersΔρmin = 0.34 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cl10.18681 (6)0.25001.23941 (6)0.01548 (18)
N10.0061 (2)0.25000.9062 (2)0.0131 (5)
N20.16158 (14)0.32929 (10)0.99219 (15)0.0123 (4)
N30.33393 (14)0.40664 (11)0.97365 (15)0.0142 (4)
N40.3289 (2)0.25001.0232 (2)0.0126 (5)
C10.06092 (17)0.32731 (13)0.93092 (18)0.0127 (4)
C20.04554 (17)0.41774 (12)0.87894 (19)0.0131 (4)
C30.04120 (19)0.45758 (14)0.80987 (19)0.0153 (4)
H30.108 (2)0.4248 (15)0.788 (2)0.020 (6)*
C40.02895 (19)0.54590 (14)0.7688 (2)0.0175 (4)
H40.0860 (18)0.5730 (14)0.721 (2)0.012 (5)*
C50.06896 (19)0.59408 (14)0.79404 (19)0.0177 (5)
H50.0743 (17)0.6584 (14)0.762 (2)0.013 (5)*
C60.15775 (18)0.55508 (13)0.8577 (2)0.0154 (4)
H60.2282 (18)0.5884 (13)0.8727 (19)0.010 (5)*
C70.14569 (17)0.46619 (13)0.90106 (19)0.0138 (4)
C80.22313 (18)0.40489 (12)0.96549 (18)0.0136 (4)
C90.38622 (18)0.32716 (13)0.99407 (18)0.0142 (4)
C100.49856 (17)0.29825 (14)0.96479 (18)0.0146 (4)
C110.59480 (18)0.34613 (15)0.9336 (2)0.0180 (5)
H110.5941 (17)0.4108 (14)0.933 (2)0.010 (5)*
C120.68951 (19)0.29737 (15)0.9044 (2)0.0214 (5)
H120.757 (2)0.3302 (15)0.884 (2)0.027 (6)*
B10.2098 (3)0.25001.0584 (3)0.0130 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0205 (4)0.0140 (3)0.0119 (3)0.0000.0007 (3)0.000
N10.0149 (13)0.0127 (12)0.0118 (11)0.0000.0019 (10)0.000
N20.0133 (9)0.0109 (8)0.0127 (8)0.0006 (7)0.0002 (7)0.0002 (6)
N30.0137 (9)0.0158 (9)0.0131 (8)0.0002 (7)0.0002 (7)0.0004 (6)
N40.0152 (14)0.0116 (11)0.0110 (11)0.0000.0007 (9)0.000
C10.0123 (10)0.0151 (10)0.0108 (9)0.0003 (8)0.0017 (8)0.0001 (7)
C20.0146 (10)0.0128 (9)0.0118 (9)0.0015 (8)0.0025 (8)0.0008 (7)
C30.0152 (11)0.0171 (10)0.0135 (10)0.0008 (9)0.0011 (8)0.0019 (8)
C40.0200 (11)0.0183 (10)0.0142 (10)0.0053 (9)0.0001 (9)0.0012 (8)
C50.0244 (12)0.0142 (10)0.0145 (10)0.0018 (9)0.0032 (8)0.0009 (8)
C60.0172 (11)0.0154 (10)0.0136 (10)0.0010 (8)0.0026 (8)0.0011 (8)
C70.0156 (11)0.0147 (10)0.0109 (9)0.0014 (8)0.0018 (8)0.0017 (7)
C80.0168 (11)0.0126 (10)0.0114 (9)0.0007 (8)0.0002 (8)0.0004 (7)
C90.0158 (11)0.0159 (10)0.0108 (9)0.0032 (9)0.0014 (8)0.0002 (7)
C100.0139 (11)0.0198 (10)0.0102 (9)0.0003 (8)0.0018 (8)0.0007 (8)
C110.0173 (12)0.0204 (12)0.0162 (10)0.0008 (9)0.0028 (8)0.0017 (9)
C120.0148 (11)0.0295 (11)0.0198 (11)0.0043 (10)0.0004 (9)0.0034 (9)
B10.0148 (18)0.0154 (16)0.0088 (14)0.0000.0002 (12)0.000
Geometric parameters (Å, º) top
Cl1—B11.874 (3)C4—C51.398 (3)
N1—C11.342 (2)C4—H40.93 (2)
N1—C1i1.342 (2)C5—C61.376 (3)
N2—C11.361 (3)C5—H51.01 (2)
N2—C81.367 (2)C6—C71.394 (3)
N2—B11.472 (2)C6—H60.99 (2)
N3—C81.332 (3)C7—C81.456 (3)
N3—C91.348 (3)C9—C101.446 (3)
N4—C9i1.364 (2)C10—C111.391 (3)
N4—C91.365 (2)C10—C10i1.426 (4)
N4—B11.474 (4)C11—C121.379 (3)
C1—C21.450 (3)C11—H110.956 (19)
C2—C31.389 (3)C12—C12i1.400 (4)
C2—C71.417 (3)C12—H120.97 (3)
C3—C41.379 (3)B1—N2i1.472 (2)
C3—H30.96 (2)
C1—N1—C1i116.6 (2)C7—C6—H6120.5 (11)
C1—N2—C8113.87 (16)C6—C7—C2120.87 (19)
C1—N2—B1122.97 (17)C6—C7—C8131.63 (19)
C8—N2—B1122.01 (18)C2—C7—C8107.43 (16)
C8—N3—C9117.21 (16)N3—C8—N2122.85 (17)
C9i—N4—C9113.4 (2)N3—C8—C7130.79 (18)
C9i—N4—B1122.82 (12)N2—C8—C7104.74 (17)
C9—N4—B1122.82 (12)N3—C9—N4121.84 (19)
N1—C1—N2122.69 (17)N3—C9—C10131.25 (18)
N1—C1—C2130.73 (19)N4—C9—C10105.56 (17)
N2—C1—C2105.21 (16)C11—C10—C10i120.56 (12)
C3—C2—C7120.18 (18)C11—C10—C9132.17 (19)
C3—C2—C1132.27 (19)C10i—C10—C9107.19 (11)
C7—C2—C1107.39 (17)C12—C11—C10117.9 (2)
C4—C3—C2118.4 (2)C12—C11—H11121.8 (13)
C4—C3—H3119.6 (13)C10—C11—H11120.2 (13)
C2—C3—H3121.9 (13)C11—C12—C12i121.51 (13)
C3—C4—C5121.0 (2)C11—C12—H12118.5 (14)
C3—C4—H4119.3 (13)C12i—C12—H12120.0 (13)
C5—C4—H4119.7 (13)N2i—B1—N2105.4 (2)
C6—C5—C4121.69 (19)N2i—B1—N4105.58 (17)
C6—C5—H5120.1 (12)N2—B1—N4105.58 (17)
C4—C5—H5118.2 (12)N2i—B1—Cl1113.44 (15)
C5—C6—C7117.7 (2)N2—B1—Cl1113.44 (15)
C5—C6—H6121.8 (11)N4—B1—Cl1112.6 (2)
C1i—N1—C1—N27.6 (4)C2—C7—C8—N3158.1 (2)
C1i—N1—C1—C2156.93 (15)C6—C7—C8—N2175.9 (2)
C8—N2—C1—N1156.18 (19)C2—C7—C8—N27.3 (2)
B1—N2—C1—N111.8 (3)C8—N3—C9—N48.9 (3)
C8—N2—C1—C211.7 (2)C8—N3—C9—C10155.9 (2)
B1—N2—C1—C2179.67 (19)C9i—N4—C9—N3157.30 (13)
N1—C1—C2—C315.0 (4)B1—N4—C9—N311.6 (3)
N2—C1—C2—C3178.4 (2)C9i—N4—C9—C1010.9 (3)
N1—C1—C2—C7160.3 (2)B1—N4—C9—C10179.7 (2)
N2—C1—C2—C76.3 (2)N3—C9—C10—C1116.2 (4)
C7—C2—C3—C42.7 (3)N4—C9—C10—C11177.2 (2)
C1—C2—C3—C4177.5 (2)N3—C9—C10—C10i160.37 (18)
C2—C3—C4—C51.0 (3)N4—C9—C10—C10i6.22 (16)
C3—C4—C5—C61.6 (3)C10i—C10—C11—C120.7 (2)
C4—C5—C6—C72.3 (3)C9—C10—C11—C12176.9 (2)
C5—C6—C7—C20.6 (3)C10—C11—C12—C12i0.7 (2)
C5—C6—C7—C8177.1 (2)C1—N2—B1—N2i26.6 (3)
C3—C2—C7—C61.9 (3)C8—N2—B1—N2i140.37 (16)
C1—C2—C7—C6177.91 (17)C1—N2—B1—N4138.09 (19)
C3—C2—C7—C8175.33 (17)C8—N2—B1—N428.9 (3)
C1—C2—C7—C80.6 (2)C1—N2—B1—Cl198.1 (2)
C9—N3—C8—N28.0 (3)C8—N2—B1—Cl194.9 (2)
C9—N3—C8—C7155.12 (19)C9i—N4—B1—N2i28.2 (3)
C1—N2—C8—N3154.79 (18)C9—N4—B1—N2i139.60 (19)
B1—N2—C8—N313.3 (3)C9i—N4—B1—N2139.60 (19)
C1—N2—C8—C712.1 (2)C9—N4—B1—N228.2 (3)
B1—N2—C8—C7179.85 (18)C9i—N4—B1—Cl196.1 (2)
C6—C7—C8—N318.7 (4)C9—N4—B1—Cl196.1 (2)
Symmetry code: (i) x, y+1/2, z.
(d1599) Chlorido(subphthalocyaninato)boron top
Crystal data top
C24H12BClN6Dx = 1.567 Mg m3
Mr = 430.66Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PnmaCell parameters from 1648 reflections
a = 12.0187 (10) Åθ = 2.6–23.7°
b = 14.7980 (13) ŵ = 0.24 mm1
c = 10.2632 (8) ÅT = 147 K
V = 1825.3 (3) Å3Plate, purple
Z = 40.19 × 0.15 × 0.08 mm
F(000) = 880
Data collection top
Bruker Kappa APEX DUO CCD
diffractometer
1597 reflections with I > 2σ(I)
Radiation source: sealed tube with Bruker Triupmh monochromatorRint = 0.071
φ and ω scansθmax = 27.8°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
h = 1515
Tmin = 0.688, Tmax = 0.746k = 1911
12814 measured reflectionsl = 913
2221 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041All H-atom parameters refined
wR(F2) = 0.094 w = 1/[σ2(Fo2) + (0.039P)2 + 0.7856P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
2221 reflectionsΔρmax = 0.31 e Å3
175 parametersΔρmin = 0.33 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cl10.18681 (6)0.25001.23911 (6)0.01767 (17)
N10.00598 (18)0.25000.9064 (2)0.0151 (5)
N20.16156 (12)0.32914 (10)0.99203 (14)0.0139 (3)
N30.33402 (13)0.40656 (10)0.97343 (14)0.0160 (4)
N40.32865 (18)0.25001.0230 (2)0.0149 (5)
C10.06075 (15)0.32725 (12)0.93072 (17)0.0143 (4)
C20.04551 (16)0.41777 (12)0.87880 (17)0.0151 (4)
C30.04118 (17)0.45752 (13)0.80993 (18)0.0172 (4)
H30.1075 (18)0.4246 (15)0.790 (2)0.028 (6)*
C40.02883 (17)0.54576 (13)0.76890 (19)0.0201 (4)
H40.0895 (16)0.5741 (14)0.7194 (19)0.020 (5)*
C50.06880 (17)0.59423 (13)0.79411 (18)0.0192 (4)
H50.0742 (16)0.6565 (14)0.7637 (19)0.023 (6)*
C60.15755 (17)0.55470 (12)0.85764 (18)0.0175 (4)
H60.2264 (17)0.5884 (14)0.8721 (18)0.021 (5)*
C70.14595 (15)0.46615 (12)0.90102 (17)0.0152 (4)
C80.22282 (16)0.40503 (12)0.96534 (17)0.0150 (4)
C90.38608 (16)0.32725 (12)0.99403 (17)0.0155 (4)
C100.49859 (16)0.29816 (12)0.96481 (17)0.0164 (4)
C110.59463 (17)0.34607 (14)0.93374 (19)0.0198 (4)
H110.5935 (17)0.4113 (14)0.932 (2)0.022 (6)*
C120.68945 (18)0.29722 (14)0.90441 (19)0.0243 (5)
H120.7574 (19)0.3323 (15)0.881 (2)0.033 (6)*
B10.2096 (3)0.25001.0580 (3)0.0145 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0241 (4)0.0145 (3)0.0144 (3)0.0000.0008 (3)0.000
N10.0162 (12)0.0137 (11)0.0154 (11)0.0000.0019 (9)0.000
N20.0142 (8)0.0123 (7)0.0153 (7)0.0009 (6)0.0003 (6)0.0001 (6)
N30.0159 (9)0.0167 (8)0.0155 (8)0.0012 (6)0.0017 (6)0.0004 (6)
N40.0173 (13)0.0129 (10)0.0145 (11)0.0000.0010 (9)0.000
C10.0130 (9)0.0170 (9)0.0130 (8)0.0010 (7)0.0021 (7)0.0001 (7)
C20.0185 (10)0.0134 (8)0.0135 (9)0.0011 (8)0.0039 (8)0.0010 (7)
C30.0176 (11)0.0171 (9)0.0170 (10)0.0014 (8)0.0005 (8)0.0016 (7)
C40.0224 (11)0.0208 (10)0.0171 (10)0.0067 (8)0.0004 (9)0.0016 (8)
C50.0274 (11)0.0134 (9)0.0167 (9)0.0021 (8)0.0030 (8)0.0024 (7)
C60.0202 (11)0.0144 (9)0.0179 (10)0.0010 (8)0.0032 (8)0.0001 (7)
C70.0169 (10)0.0150 (9)0.0136 (9)0.0011 (8)0.0025 (8)0.0005 (7)
C80.0186 (10)0.0121 (9)0.0144 (9)0.0017 (7)0.0011 (7)0.0010 (7)
C90.0177 (10)0.0164 (9)0.0125 (9)0.0038 (8)0.0006 (7)0.0013 (7)
C100.0167 (10)0.0190 (10)0.0136 (9)0.0005 (7)0.0029 (8)0.0005 (7)
C110.0195 (11)0.0217 (10)0.0183 (10)0.0024 (8)0.0020 (8)0.0015 (8)
C120.0177 (11)0.0323 (11)0.0231 (10)0.0047 (9)0.0001 (9)0.0031 (9)
B10.0158 (16)0.0121 (13)0.0154 (14)0.0000.0010 (12)0.000
Geometric parameters (Å, º) top
Cl1—B11.879 (3)C4—C51.399 (3)
N1—C11.342 (2)C4—H40.98 (2)
N1—C1i1.342 (2)C5—C61.380 (3)
N2—C11.366 (2)C5—H50.97 (2)
N2—C81.371 (2)C6—C71.391 (3)
N2—B11.471 (2)C6—H60.98 (2)
N3—C81.339 (2)C7—C81.452 (3)
N3—C91.347 (2)C9—C101.451 (3)
N4—C91.368 (2)C10—C111.392 (3)
N4—C9i1.368 (2)C10—C10i1.425 (4)
N4—B11.475 (4)C11—C121.383 (3)
C1—C21.453 (2)C11—H110.97 (2)
C2—C31.390 (3)C12—C12i1.398 (4)
C2—C71.422 (3)C12—H121.00 (2)
C3—C41.380 (3)B1—N2i1.471 (2)
C3—H30.95 (2)
C1—N1—C1i116.7 (2)C7—C6—H6121.1 (12)
C1—N2—C8113.66 (15)C6—C7—C2120.54 (17)
C1—N2—B1122.96 (16)C6—C7—C8131.97 (18)
C8—N2—B1122.25 (17)C2—C7—C8107.43 (15)
C8—N3—C9117.30 (16)N3—C8—N2122.51 (16)
C9—N4—C9i113.3 (2)N3—C8—C7130.75 (17)
C9—N4—B1122.84 (12)N2—C8—C7105.05 (16)
C9i—N4—B1122.84 (12)N3—C9—N4121.87 (18)
N1—C1—N2122.56 (17)N3—C9—C10131.25 (17)
N1—C1—C2130.91 (17)N4—C9—C10105.51 (17)
N2—C1—C2105.18 (15)C11—C10—C10i120.63 (11)
C3—C2—C7120.33 (17)C11—C10—C9132.02 (18)
C3—C2—C1132.16 (18)C10i—C10—C9107.27 (10)
C7—C2—C1107.36 (16)C12—C11—C10117.85 (19)
C4—C3—C2118.37 (19)C12—C11—H11122.0 (13)
C4—C3—H3120.5 (13)C10—C11—H11120.1 (12)
C2—C3—H3121.1 (13)C11—C12—C12i121.52 (12)
C3—C4—C5121.25 (19)C11—C12—H12117.0 (13)
C3—C4—H4118.8 (12)C12i—C12—H12121.4 (13)
C5—C4—H4119.9 (12)N2—B1—N2i105.6 (2)
C6—C5—C4121.21 (18)N2—B1—N4105.60 (16)
C6—C5—H5120.0 (12)N2i—B1—N4105.60 (16)
C4—C5—H5118.7 (12)N2—B1—Cl1113.46 (14)
C5—C6—C7118.22 (18)N2i—B1—Cl1113.46 (14)
C5—C6—H6120.7 (12)N4—B1—Cl1112.45 (19)
C1i—N1—C1—N27.9 (3)C2—C7—C8—N3158.00 (18)
C1i—N1—C1—C2156.76 (14)C6—C7—C8—N2175.92 (19)
C8—N2—C1—N1156.51 (18)C2—C7—C8—N27.09 (19)
B1—N2—C1—N111.6 (3)C8—N3—C9—N48.6 (3)
C8—N2—C1—C211.56 (19)C8—N3—C9—C10155.95 (18)
B1—N2—C1—C2179.65 (18)C9i—N4—C9—N3157.27 (13)
N1—C1—C2—C314.9 (3)B1—N4—C9—N311.7 (3)
N2—C1—C2—C3178.41 (19)C9i—N4—C9—C1010.7 (3)
N1—C1—C2—C7160.4 (2)B1—N4—C9—C10179.7 (2)
N2—C1—C2—C76.28 (19)N3—C9—C10—C1116.3 (3)
C7—C2—C3—C42.7 (3)N4—C9—C10—C11177.3 (2)
C1—C2—C3—C4177.47 (19)N3—C9—C10—C10i160.27 (17)
C2—C3—C4—C50.8 (3)N4—C9—C10—C10i6.15 (15)
C3—C4—C5—C61.9 (3)C10i—C10—C11—C120.6 (2)
C4—C5—C6—C72.6 (3)C9—C10—C11—C12176.85 (19)
C5—C6—C7—C20.7 (3)C10—C11—C12—C12i0.6 (2)
C5—C6—C7—C8177.37 (19)C1—N2—B1—N2i26.6 (3)
C3—C2—C7—C61.9 (3)C8—N2—B1—N2i140.46 (15)
C1—C2—C7—C6177.92 (16)C1—N2—B1—N4138.19 (17)
C3—C2—C7—C8175.46 (16)C8—N2—B1—N428.9 (2)
C1—C2—C7—C80.5 (2)C1—N2—B1—Cl198.21 (18)
C9—N3—C8—N27.8 (3)C8—N2—B1—Cl194.7 (2)
C9—N3—C8—C7155.11 (18)C9—N4—B1—N228.2 (3)
C1—N2—C8—N3154.76 (17)C9i—N4—B1—N2139.72 (18)
B1—N2—C8—N313.4 (3)C9—N4—B1—N2i139.72 (18)
C1—N2—C8—C711.87 (19)C9i—N4—B1—N2i28.2 (3)
B1—N2—C8—C7179.94 (17)C9—N4—B1—Cl196.04 (19)
C6—C7—C8—N319.0 (3)C9i—N4—B1—Cl196.04 (19)
Symmetry code: (i) x, y+1/2, z.
(d1598) Chlorido(subphthalocyaninato)boron top
Crystal data top
C24H12BClN6Dx = 1.535 Mg m3
Mr = 430.66Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PnmaCell parameters from 1837 reflections
a = 12.0634 (9) Åθ = 2.7–25.5°
b = 14.8634 (11) ŵ = 0.23 mm1
c = 10.3901 (6) ÅT = 295 K
V = 1863.0 (2) Å3Plate, purple
Z = 40.19 × 0.15 × 0.08 mm
F(000) = 880
Data collection top
Bruker Kappa APEX DUO CCD
diffractometer
1581 reflections with I > 2σ(I)
Radiation source: sealed tube with Bruker Triumph monochromatorRint = 0.044
φ and ω scansθmax = 27.4°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
h = 1515
Tmin = 0.701, Tmax = 0.746k = 1911
9199 measured reflectionsl = 139
2187 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040All H-atom parameters refined
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.0407P)2 + 0.780P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2187 reflectionsΔρmax = 0.29 e Å3
175 parametersΔρmin = 0.30 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cl10.18599 (6)0.25001.23566 (6)0.03204 (19)
N10.00654 (18)0.25000.9068 (2)0.0266 (5)
N20.16161 (12)0.32896 (9)0.99164 (13)0.0243 (3)
N30.33338 (13)0.40592 (10)0.97310 (14)0.0277 (4)
N40.32808 (18)0.25001.02278 (19)0.0258 (5)
C10.06145 (15)0.32705 (11)0.93108 (16)0.0243 (4)
C20.04625 (15)0.41714 (11)0.87931 (16)0.0258 (4)
C30.04012 (17)0.45645 (13)0.81101 (18)0.0304 (4)
H30.1058 (18)0.4256 (14)0.7903 (19)0.040 (6)*
C40.02736 (19)0.54419 (13)0.77054 (19)0.0357 (5)
H40.0852 (17)0.5707 (14)0.7220 (19)0.037 (6)*
C50.06958 (19)0.59198 (13)0.79456 (18)0.0355 (5)
H50.0746 (16)0.6531 (14)0.7627 (18)0.035 (5)*
C60.15801 (18)0.55337 (12)0.85740 (18)0.0312 (4)
H60.2274 (17)0.5853 (14)0.8719 (18)0.039 (6)*
C70.14604 (15)0.46508 (11)0.90122 (16)0.0266 (4)
C80.22269 (16)0.40434 (11)0.96479 (16)0.0255 (4)
C90.38514 (16)0.32698 (12)0.99401 (16)0.0269 (4)
C100.49755 (16)0.29793 (12)0.96533 (16)0.0291 (4)
C110.59319 (18)0.34546 (15)0.93420 (19)0.0378 (5)
H110.5916 (17)0.4106 (14)0.9360 (19)0.039 (6)*
C120.68726 (19)0.29691 (16)0.9058 (2)0.0466 (6)
H120.755 (2)0.3298 (16)0.885 (2)0.069 (8)*
B10.2098 (3)0.25001.0569 (3)0.0245 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0444 (4)0.0256 (3)0.0261 (3)0.0000.0019 (3)0.000
N10.0262 (13)0.0244 (11)0.0290 (12)0.0000.0017 (9)0.000
N20.0252 (9)0.0204 (7)0.0273 (7)0.0010 (6)0.0003 (6)0.0005 (6)
N30.0279 (10)0.0249 (8)0.0303 (8)0.0027 (6)0.0023 (6)0.0000 (6)
N40.0263 (13)0.0240 (10)0.0270 (11)0.0000.0008 (9)0.000
C10.0239 (10)0.0241 (8)0.0249 (9)0.0010 (7)0.0030 (7)0.0001 (7)
C20.0298 (11)0.0230 (8)0.0245 (9)0.0026 (8)0.0041 (7)0.0007 (7)
C30.0282 (11)0.0317 (10)0.0312 (10)0.0042 (8)0.0001 (8)0.0006 (8)
C40.0384 (12)0.0343 (10)0.0345 (11)0.0104 (9)0.0017 (9)0.0074 (8)
C50.0461 (13)0.0254 (9)0.0351 (11)0.0037 (9)0.0053 (9)0.0084 (8)
C60.0361 (12)0.0244 (9)0.0330 (10)0.0006 (8)0.0050 (8)0.0035 (7)
C70.0302 (11)0.0234 (9)0.0263 (9)0.0015 (8)0.0036 (8)0.0004 (7)
C80.0283 (11)0.0215 (8)0.0267 (9)0.0027 (7)0.0002 (7)0.0002 (7)
C90.0260 (11)0.0269 (9)0.0279 (9)0.0043 (8)0.0030 (7)0.0010 (7)
C100.0237 (10)0.0368 (10)0.0267 (9)0.0020 (8)0.0045 (8)0.0014 (8)
C110.0312 (12)0.0425 (12)0.0397 (11)0.0054 (9)0.0042 (9)0.0044 (9)
C120.0271 (12)0.0602 (14)0.0524 (13)0.0064 (11)0.0023 (10)0.0054 (11)
B10.0259 (17)0.0218 (13)0.0260 (14)0.0000.0003 (12)0.000
Geometric parameters (Å, º) top
Cl1—B11.880 (3)C4—C51.391 (3)
N1—C1i1.347 (2)C4—H40.95 (2)
N1—C11.347 (2)C5—C61.376 (3)
N2—C11.363 (2)C5—H50.97 (2)
N2—C81.370 (2)C6—C71.397 (2)
N2—B11.474 (2)C6—H60.97 (2)
N3—C81.338 (2)C7—C81.451 (2)
N3—C91.347 (2)C9—C101.454 (3)
N4—C9i1.368 (2)C10—C111.391 (3)
N4—C91.368 (2)C10—C10i1.425 (4)
N4—B11.471 (4)C11—C121.377 (3)
C1—C21.455 (2)C11—H110.97 (2)
C2—C31.389 (3)C12—C12i1.395 (5)
C2—C71.417 (2)C12—H120.97 (3)
C3—C41.379 (3)B1—N2i1.474 (2)
C3—H30.94 (2)
C1i—N1—C1116.5 (2)C7—C6—H6119.8 (12)
C1—N2—C8113.58 (14)C6—C7—C2120.53 (17)
C1—N2—B1123.03 (16)C6—C7—C8131.84 (18)
C8—N2—B1122.20 (17)C2—C7—C8107.55 (15)
C8—N3—C9117.24 (15)N3—C8—N2122.54 (16)
C9i—N4—C9113.5 (2)N3—C8—C7130.86 (16)
C9i—N4—B1122.74 (11)N2—C8—C7105.00 (15)
C9—N4—B1122.74 (11)N3—C9—N4122.04 (17)
N1—C1—N2122.70 (16)N3—C9—C10131.15 (17)
N1—C1—C2130.66 (17)N4—C9—C10105.41 (16)
N2—C1—C2105.27 (15)C11—C10—C10i120.52 (12)
C3—C2—C7120.50 (16)C11—C10—C9132.10 (18)
C3—C2—C1132.10 (18)C10i—C10—C9107.28 (10)
C7—C2—C1107.24 (15)C12—C11—C10117.9 (2)
C4—C3—C2118.02 (19)C12—C11—H11123.0 (13)
C4—C3—H3119.1 (13)C10—C11—H11119.1 (13)
C2—C3—H3122.9 (13)C11—C12—C12i121.60 (14)
C3—C4—C5121.48 (19)C11—C12—H12118.2 (15)
C3—C4—H4118.2 (13)C12i—C12—H12120.2 (15)
C5—C4—H4120.2 (12)N4—B1—N2105.77 (15)
C6—C5—C4121.59 (18)N4—B1—N2i105.77 (15)
C6—C5—H5120.3 (12)N2—B1—N2i105.5 (2)
C4—C5—H5118.1 (12)N4—B1—Cl1112.70 (19)
C5—C6—C7117.80 (19)N2—B1—Cl1113.21 (13)
C5—C6—H6122.4 (12)N2i—B1—Cl1113.21 (13)
C1i—N1—C1—N27.9 (3)C2—C7—C8—N3158.17 (18)
C1i—N1—C1—C2156.64 (13)C6—C7—C8—N2176.21 (18)
C8—N2—C1—N1156.25 (17)C2—C7—C8—N27.31 (18)
B1—N2—C1—N111.4 (3)C8—N3—C9—N48.5 (3)
C8—N2—C1—C211.68 (19)C8—N3—C9—C10155.86 (18)
B1—N2—C1—C2179.38 (17)C9i—N4—C9—N3156.90 (12)
N1—C1—C2—C315.0 (3)B1—N4—C9—N311.7 (3)
N2—C1—C2—C3178.42 (18)C9i—N4—C9—C1011.0 (3)
N1—C1—C2—C7160.32 (19)B1—N4—C9—C10179.61 (19)
N2—C1—C2—C76.26 (18)N3—C9—C10—C1116.2 (3)
C7—C2—C3—C42.7 (3)N4—C9—C10—C11177.5 (2)
C1—C2—C3—C4177.54 (18)N3—C9—C10—C10i160.04 (16)
C2—C3—C4—C51.3 (3)N4—C9—C10—C10i6.27 (15)
C3—C4—C5—C61.4 (3)C10i—C10—C11—C121.0 (2)
C4—C5—C6—C72.4 (3)C9—C10—C11—C12176.82 (19)
C5—C6—C7—C20.9 (3)C10—C11—C12—C12i1.0 (2)
C5—C6—C7—C8177.05 (18)C9i—N4—B1—N2139.60 (17)
C3—C2—C7—C61.7 (3)C9—N4—B1—N228.0 (3)
C1—C2—C7—C6177.63 (16)C9i—N4—B1—N2i28.0 (3)
C3—C2—C7—C8175.29 (16)C9—N4—B1—N2i139.60 (17)
C1—C2—C7—C80.67 (19)C9i—N4—B1—Cl196.20 (19)
C9—N3—C8—N27.9 (2)C9—N4—B1—Cl196.20 (19)
C9—N3—C8—C7155.38 (17)C1—N2—B1—N4138.19 (17)
C1—N2—C8—N3154.92 (16)C8—N2—B1—N428.5 (2)
B1—N2—C8—N312.9 (3)C1—N2—B1—N2i26.4 (3)
C1—N2—C8—C712.07 (19)C8—N2—B1—N2i140.27 (15)
B1—N2—C8—C7179.89 (16)C1—N2—B1—Cl197.93 (18)
C6—C7—C8—N318.3 (3)C8—N2—B1—Cl195.4 (2)
Symmetry code: (i) x, y+1/2, z.
Diffraction experimental details from previously published structures of Cl-BsubPc, (I) top
Kietaibl (1974)Solntsev et al. (2012)
Temperature (K)~295 (room temperature)123
a, b, c (Å)12.123 (5), 14.824 (7), 10.378 (4)12.1224 (2), 14.8449 (10), 10.3283 (1)
V3)1865.0 (14)1858.64 (13)
Molar density (kmol m-3)3.5616 (27)3.5737 (2)
Selected molecular and intermolecular metrics for Cl-BsubPc, (I), at different temperatures top
90 Ka (Crystal 2)123 Ka (Crystal 2)123 Kb147 Ka (Crystal 1)147 Ka (Crystal 2)295 Ka (Crystal 2)295 Kc
Molecular metrics
B—Cl (Å)1.881 (2)1.874 (3)1.890 (6)1.879 (2)1.879 (3)1.880 (3)1.863 (7)
Bowl depth (Å)2.450 (2)2.450 (3)2.454 (6)2.4587 (19)2.451 (3)2.457 (3)2.472 (9)
Convex–convex
Cg(I)···Cg(J) (Å)3.5988 (10)3.5989 (13)3.629 (2)3.6127 (9)3.6065 (11)3.6495 (11)3.6545 (17)
Concave–concave
Cg(K)···Cg(L) (Å)4.1282 (10)4.1291 (13)4.178 (2)4.1494 (10)4.1368 (12)4.1959 (12)4.2043 (17)
Halogen–π
Cl···Cg(L) (Å)3.5167 (9)3.5218 (11)3.567 (2)3.5404 (9)3.5316 (10)3.6012 (10)3.5986 (17)
B—Cl···Cg(L) (°)169.99 (8)170.09 (12)169.7 (2)170.18 (6)170.02 (12)170.58 (12)170.0 (5)
Notes: (a) data from this work [centroid definitions: Cg(I) = Cg(1) = N2/C1/C2/C7/C8; Cg(J) = Cg(6) = C2–C7; Cg(K) = Cg(3) = B1/N2/C1/N1/C1a/N2a; Cg(L) = Cg(7) = C10–C12/C12a–C10a; atoms labelled according to Fig. 3]; (b) data from Solntsev et al. (2012) [centroid definitions: Cg(I) = N1/C1–C4; Cg(J) = C2/C3/C8–C5; Cg(K) = B1/N1a/C4a/N4a/C9a/N2; Cg(L) = C10–C12/C12a–C10a]; (c) data from Kietaibl (1974) [centroid definitions: Cg(I) = N2/C1/C5/C10/C11; Cg(J) = C5–C10; Cg(K) = B1/N2/C1/N1/C1a/N2a; Cg(L) = C2–C4/C4a–C2a].
 

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