Download citation
Download citation
link to html
We obtained two conformational polymorphs of 2,5-di­chloro-3,6-bis­(di­benzyl­amino)-p-hydro­quinone, C34H30Cl2N2O2. Both polymorphs have an inversion centre at the centre of the hydro­quinone ring (Z′ = 1 \over 2), and there are no significant differences between their bond lengths and angles. The most significant structural difference in the mol­ecular conformations was found in the rotation of the phenyl rings of the two crystallographically independent benzyl groups. The crystal structures of the polymorphs were distinguishable with respect to the arrangement of the hydro­quinone rings and the packing motif of the phenyl rings that form part of the benzyl groups. The phenyl groups of one polymorph are arranged in a face-to-edge motif between adjacent mol­ecules, with inter­molecular C—H...π inter­actions, whereas the phenyl rings in the other polymorph form a lamellar stacking pattern with no significant inter­molecular inter­actions. We suggest that this partial conformational difference in the mol­ecular structures leads to the significant structural differences observed in their mol­ecular arrangements.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618003595/ky3138sup1.cif
Contains datablocks global, 20130730_colorless_block, 20130722_palered_block

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618003595/ky313820130730_colorless_blocksup2.hkl
Contains datablock 20130730_colorless_block

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618003595/ky313820130722_palered_blocksup3.hkl
Contains datablock 20130722_palered_block

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618003595/ky313820130730_colorless_blocksup4.cml
Supplementary material

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229618003595/ky3138sup5.pdf
DSC profile and PXRD patterns

CCDC references: 1826861; 1826860

Computing details top

For both structures, data collection: RAPID-AUTO (Rigaku, 2000); cell refinement: RAPID-AUTO (Rigaku, 2000); data reduction: RAPID-AUTO (Rigaku, 2000); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: CrystalStructure (Rigaku, 2017) and Mercury (Macrae et al., 2008); software used to prepare material for publication: CrystalStructure (Rigaku, 2017).

2,5-Bis(dibenzylamino)-3,6-dichlorobenzene-1,4-diol (20130730_colorless_block) top
Crystal data top
C34H30Cl2N2O2F(000) = 596.00
Mr = 569.53Dx = 1.319 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54187 Å
a = 9.67404 (18) ÅCell parameters from 10981 reflections
b = 10.9707 (2) Åθ = 3.3–68.2°
c = 13.5552 (3) ŵ = 2.30 mm1
β = 94.7380 (7)°T = 296 K
V = 1433.72 (5) Å3Block, colorless
Z = 20.40 × 0.33 × 0.23 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2101 reflections with F2 > 2.0σ(F2)
Detector resolution: 10.000 pixels mm-1Rint = 0.070
ω scansθmax = 66.5°, θmin = 5.2°
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)
h = 1111
Tmin = 0.492, Tmax = 0.589k = 1312
12895 measured reflectionsl = 1616
2527 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0573P)2 + 0.3915P]
where P = (Fo2 + 2Fc2)/3
2527 reflections(Δ/σ)max < 0.001
181 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.32 e Å3
Primary atom site location: structure-invariant direct methods
Special details top

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 was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 sigma(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.23763 (5)0.60878 (5)0.58672 (5)0.0671 (2)
O10.50864 (15)0.25956 (12)0.44492 (11)0.0578 (4)
H10.43300.22800.45100.069*
N10.27948 (15)0.33329 (14)0.52062 (11)0.0471 (4)
C10.38157 (19)0.54615 (17)0.53814 (14)0.0472 (5)
C20.50464 (19)0.37915 (16)0.47231 (14)0.0456 (4)
C30.38501 (18)0.42424 (17)0.51024 (14)0.0443 (4)
C40.2697 (2)0.2951 (2)0.62473 (15)0.0563 (5)
H4A0.21690.35530.65820.068*
H4B0.36210.29160.65840.068*
C50.2012 (2)0.17238 (19)0.63111 (14)0.0511 (5)
C60.2621 (3)0.0708 (2)0.5945 (2)0.0787 (8)
H60.34390.07940.56360.094*
C70.2052 (4)0.0436 (3)0.6023 (2)0.0935 (9)
H70.24870.11090.57690.112*
C80.0857 (3)0.0581 (3)0.6468 (2)0.0825 (8)
H80.04660.13510.65150.099*
C90.0231 (3)0.0415 (3)0.6847 (2)0.0894 (9)
H90.05860.03200.71550.107*
C100.0815 (3)0.1569 (2)0.6773 (2)0.0747 (7)
H100.03890.22390.70380.090*
C110.14278 (19)0.3557 (2)0.46778 (15)0.0534 (5)
H11A0.10280.42810.49500.064*
H11B0.08230.28760.47940.064*
C120.14744 (19)0.37228 (19)0.35847 (15)0.0513 (5)
C130.1040 (3)0.4804 (2)0.31389 (18)0.0696 (6)
H130.07710.54460.35280.084*
C140.1000 (3)0.4945 (3)0.2136 (2)0.0937 (9)
H140.06980.56780.18480.112*
C150.1400 (3)0.4016 (4)0.1557 (2)0.0994 (11)
H150.13760.41190.08750.119*
C160.1842 (3)0.2922 (3)0.1976 (2)0.0884 (9)
H160.21150.22880.15800.106*
C170.1872 (2)0.2781 (2)0.29918 (18)0.0653 (6)
H170.21640.20450.32790.078*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0469 (3)0.0551 (4)0.1018 (5)0.0003 (2)0.0209 (3)0.0140 (3)
O10.0512 (8)0.0380 (7)0.0852 (10)0.0062 (6)0.0105 (7)0.0088 (7)
N10.0411 (8)0.0449 (9)0.0552 (9)0.0097 (7)0.0031 (7)0.0023 (7)
C10.0386 (9)0.0423 (11)0.0608 (11)0.0005 (8)0.0050 (8)0.0005 (8)
C20.0429 (10)0.0369 (10)0.0566 (11)0.0014 (7)0.0023 (8)0.0035 (8)
C30.0383 (9)0.0405 (10)0.0539 (10)0.0044 (7)0.0020 (8)0.0012 (8)
C40.0623 (13)0.0525 (12)0.0539 (11)0.0106 (10)0.0034 (9)0.0018 (9)
C50.0507 (11)0.0511 (12)0.0513 (11)0.0068 (9)0.0040 (8)0.0062 (9)
C60.0799 (17)0.0577 (15)0.104 (2)0.0041 (12)0.0393 (15)0.0087 (13)
C70.121 (2)0.0533 (16)0.112 (2)0.0106 (15)0.0447 (19)0.0034 (14)
C80.0879 (19)0.0638 (17)0.0942 (19)0.0256 (15)0.0020 (15)0.0164 (14)
C90.0590 (15)0.094 (2)0.117 (2)0.0174 (14)0.0193 (14)0.0338 (18)
C100.0664 (15)0.0677 (16)0.0934 (18)0.0009 (12)0.0275 (13)0.0113 (13)
C110.0388 (10)0.0586 (12)0.0628 (12)0.0069 (9)0.0028 (9)0.0030 (9)
C120.0378 (10)0.0537 (12)0.0616 (12)0.0105 (8)0.0010 (8)0.0042 (9)
C130.0696 (15)0.0632 (15)0.0751 (15)0.0053 (12)0.0002 (12)0.0099 (12)
C140.097 (2)0.095 (2)0.087 (2)0.0101 (18)0.0032 (16)0.0305 (18)
C150.086 (2)0.147 (3)0.0642 (17)0.020 (2)0.0021 (15)0.0167 (19)
C160.0723 (17)0.118 (3)0.0746 (17)0.0085 (17)0.0060 (13)0.0263 (17)
C170.0573 (13)0.0657 (15)0.0722 (15)0.0038 (11)0.0006 (11)0.0074 (12)
Geometric parameters (Å, º) top
Cl1—C11.7309 (19)C8—C91.369 (4)
O1—C21.365 (2)C8—H80.9300
O1—H10.8200C9—C101.393 (4)
N1—C31.443 (2)C9—H90.9300
N1—C111.472 (2)C10—H100.9300
N1—C41.482 (2)C11—C121.497 (3)
C1—C2i1.389 (3)C11—H11A0.9700
C1—C31.391 (3)C11—H11B0.9700
C2—C1i1.389 (3)C12—C131.381 (3)
C2—C31.395 (3)C12—C171.383 (3)
C4—C51.507 (3)C13—C141.365 (4)
C4—H4A0.9700C13—H130.9300
C4—H4B0.9700C14—C151.363 (5)
C5—C101.372 (3)C14—H140.9300
C5—C61.372 (3)C15—C161.380 (5)
C6—C71.378 (4)C15—H150.9300
C6—H60.9300C16—C171.384 (4)
C7—C81.356 (4)C16—H160.9300
C7—H70.9300C17—H170.9300
C2—O1—H1109.5C8—C9—C10120.2 (3)
C3—N1—C11116.86 (15)C8—C9—H9119.9
C3—N1—C4112.92 (14)C10—C9—H9119.9
C11—N1—C4112.65 (15)C5—C10—C9120.5 (3)
C2i—C1—C3120.17 (17)C5—C10—H10119.7
C2i—C1—Cl1118.29 (15)C9—C10—H10119.7
C3—C1—Cl1121.55 (14)N1—C11—C12113.74 (16)
O1—C2—C1i119.93 (17)N1—C11—H11A108.8
O1—C2—C3118.95 (17)C12—C11—H11A108.8
C1i—C2—C3121.12 (17)N1—C11—H11B108.8
C1—C3—C2118.71 (17)C12—C11—H11B108.8
C1—C3—N1127.26 (17)H11A—C11—H11B107.7
C2—C3—N1113.95 (16)C13—C12—C17118.5 (2)
N1—C4—C5111.72 (16)C13—C12—C11120.3 (2)
N1—C4—H4A109.3C17—C12—C11121.1 (2)
C5—C4—H4A109.3C14—C13—C12121.1 (3)
N1—C4—H4B109.3C14—C13—H13119.5
C5—C4—H4B109.3C12—C13—H13119.5
H4A—C4—H4B107.9C15—C14—C13120.2 (3)
C10—C5—C6117.9 (2)C15—C14—H14119.9
C10—C5—C4122.0 (2)C13—C14—H14119.9
C6—C5—C4120.0 (2)C14—C15—C16120.4 (3)
C5—C6—C7121.7 (2)C14—C15—H15119.8
C5—C6—H6119.2C16—C15—H15119.8
C7—C6—H6119.2C15—C16—C17119.2 (3)
C8—C7—C6120.1 (3)C15—C16—H16120.4
C8—C7—H7119.9C17—C16—H16120.4
C6—C7—H7119.9C12—C17—C16120.7 (3)
C7—C8—C9119.5 (3)C12—C17—H17119.7
C7—C8—H8120.3C16—C17—H17119.7
C9—C8—H8120.3
C2i—C1—C3—C20.3 (3)C5—C6—C7—C80.2 (5)
Cl1—C1—C3—C2179.49 (14)C6—C7—C8—C90.7 (5)
C2i—C1—C3—N1176.67 (17)C7—C8—C9—C100.2 (5)
Cl1—C1—C3—N13.1 (3)C6—C5—C10—C91.1 (4)
O1—C2—C3—C1179.93 (17)C4—C5—C10—C9177.9 (2)
C1i—C2—C3—C10.3 (3)C8—C9—C10—C50.7 (4)
O1—C2—C3—N13.1 (3)C3—N1—C11—C1257.2 (2)
C1i—C2—C3—N1177.14 (17)C4—N1—C11—C12169.59 (17)
C11—N1—C3—C161.2 (3)N1—C11—C12—C13118.9 (2)
C4—N1—C3—C171.9 (2)N1—C11—C12—C1764.9 (3)
C11—N1—C3—C2122.31 (19)C17—C12—C13—C140.1 (3)
C4—N1—C3—C2104.6 (2)C11—C12—C13—C14176.1 (2)
C3—N1—C4—C5158.83 (17)C12—C13—C14—C150.5 (4)
C11—N1—C4—C566.1 (2)C13—C14—C15—C160.4 (5)
N1—C4—C5—C10120.2 (2)C14—C15—C16—C170.0 (5)
N1—C4—C5—C663.1 (3)C13—C12—C17—C160.3 (3)
C10—C5—C6—C70.7 (4)C11—C12—C17—C16176.5 (2)
C4—C5—C6—C7177.6 (3)C15—C16—C17—C120.3 (4)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.822.162.645 (2)118
2,5-Bis(dibenzylamino)-3,6-dichlorobenzene-1,4-diol (20130722_palered_block) top
Crystal data top
C34H30Cl2N2O2Dx = 1.366 Mg m3
Mr = 569.53Cu Kα radiation, λ = 1.54187 Å
Orthorhombic, PbcaCell parameters from 17342 reflections
a = 13.2054 (2) Åθ = 3.4–68.2°
b = 12.4456 (2) ŵ = 2.39 mm1
c = 16.8489 (3) ÅT = 296 K
V = 2769.09 (9) Å3Block, pale red
Z = 40.40 × 0.30 × 0.28 mm
F(000) = 1192.00
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1976 reflections with F2 > 2.0σ(F2)
Detector resolution: 10.000 pixels mm-1Rint = 0.039
ω scansθmax = 66.5°, θmin = 5.3°
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)
h = 1515
Tmin = 0.413, Tmax = 0.507k = 1414
23298 measured reflectionsl = 2020
2442 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0633P)2 + 0.3919P]
where P = (Fo2 + 2Fc2)/3
2442 reflections(Δ/σ)max < 0.001
181 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.20 e Å3
Primary atom site location: structure-invariant direct methods
Special details top

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 was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 sigma(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.66299 (4)0.47433 (4)0.63253 (3)0.0591 (2)
O10.54700 (11)0.30198 (9)0.56222 (9)0.0591 (4)
H10.51690.25480.53780.071*
N10.59086 (11)0.69385 (10)0.55443 (9)0.0442 (4)
C10.57303 (13)0.49107 (13)0.55909 (11)0.0436 (4)
C20.52341 (13)0.40005 (13)0.53069 (11)0.0426 (4)
C30.54977 (13)0.59272 (13)0.52829 (11)0.0404 (4)
C40.55436 (16)0.72490 (15)0.63403 (12)0.0534 (5)
H4A0.59350.68630.67360.064*
H4B0.48430.70250.63940.064*
C50.56120 (13)0.84400 (14)0.65136 (11)0.0463 (4)
C60.56417 (15)0.87817 (16)0.72920 (12)0.0559 (5)
H60.56550.82770.76990.067*
C70.56520 (17)0.98641 (18)0.74745 (14)0.0663 (6)
H70.56711.00820.80020.080*
C80.56340 (16)1.06209 (17)0.68797 (15)0.0662 (6)
H80.56331.13490.70040.079*
C90.56174 (16)1.02952 (15)0.61040 (15)0.0601 (6)
H90.56181.08030.56990.072*
C100.56001 (15)0.92137 (15)0.59207 (13)0.0543 (5)
H100.55800.90010.53920.065*
C110.70119 (14)0.70866 (14)0.54321 (12)0.0515 (5)
H11A0.73690.65080.56980.062*
H11B0.72170.77570.56770.062*
C120.73094 (14)0.71014 (13)0.45730 (12)0.0497 (5)
C130.71914 (18)0.80139 (16)0.41111 (15)0.0698 (7)
H130.69070.86260.43350.084*
C140.7485 (2)0.80329 (19)0.33315 (16)0.0790 (7)
H140.73990.86560.30340.095*
C150.79067 (18)0.71382 (19)0.29857 (14)0.0718 (7)
H150.81060.71520.24570.086*
C160.80286 (17)0.62302 (19)0.34285 (15)0.0689 (6)
H160.83160.56220.32000.083*
C170.77298 (16)0.62081 (16)0.42091 (14)0.0609 (6)
H170.78120.55790.45000.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0653 (4)0.0469 (3)0.0651 (4)0.0030 (2)0.0185 (2)0.0012 (2)
O10.0731 (9)0.0293 (6)0.0748 (10)0.0011 (6)0.0143 (7)0.0051 (6)
N10.0484 (9)0.0320 (7)0.0523 (9)0.0043 (6)0.0044 (7)0.0072 (6)
C10.0475 (10)0.0361 (9)0.0472 (11)0.0015 (7)0.0018 (8)0.0018 (8)
C20.0497 (10)0.0293 (8)0.0488 (11)0.0029 (7)0.0014 (8)0.0015 (7)
C30.0448 (9)0.0303 (8)0.0461 (10)0.0006 (7)0.0037 (8)0.0030 (7)
C40.0672 (13)0.0384 (10)0.0546 (12)0.0027 (9)0.0083 (9)0.0064 (8)
C50.0478 (10)0.0376 (10)0.0534 (11)0.0008 (8)0.0010 (8)0.0071 (8)
C60.0621 (12)0.0518 (11)0.0537 (12)0.0002 (9)0.0009 (9)0.0068 (9)
C70.0749 (14)0.0604 (13)0.0637 (16)0.0002 (11)0.0003 (11)0.0239 (11)
C80.0678 (14)0.0420 (11)0.0888 (17)0.0004 (10)0.0005 (12)0.0189 (12)
C90.0671 (14)0.0389 (11)0.0744 (16)0.0021 (9)0.0025 (11)0.0023 (10)
C100.0635 (13)0.0431 (11)0.0564 (12)0.0002 (9)0.0032 (10)0.0061 (9)
C110.0492 (11)0.0435 (10)0.0619 (13)0.0062 (8)0.0030 (9)0.0064 (9)
C120.0455 (11)0.0384 (9)0.0651 (13)0.0057 (7)0.0057 (9)0.0060 (9)
C130.0837 (16)0.0427 (11)0.0831 (17)0.0026 (10)0.0273 (13)0.0010 (10)
C140.0929 (18)0.0616 (14)0.0824 (17)0.0039 (12)0.0206 (15)0.0147 (13)
C150.0717 (15)0.0784 (17)0.0653 (15)0.0159 (12)0.0136 (12)0.0100 (13)
C160.0688 (14)0.0613 (14)0.0768 (17)0.0043 (11)0.0125 (12)0.0224 (12)
C170.0637 (13)0.0453 (11)0.0738 (15)0.0015 (9)0.0048 (11)0.0072 (10)
Geometric parameters (Å, º) top
Cl1—C11.7280 (19)C8—C91.368 (3)
O1—C21.367 (2)C8—H80.9300
O1—H10.8200C9—C101.381 (3)
N1—C31.440 (2)C9—H90.9300
N1—C41.477 (2)C10—H100.9300
N1—C111.481 (2)C11—C121.500 (3)
C1—C21.393 (2)C11—H11A0.9700
C1—C31.402 (2)C11—H11B0.9700
C2—C3i1.389 (3)C12—C131.385 (3)
C3—C2i1.389 (3)C12—C171.386 (3)
C4—C51.514 (2)C13—C141.370 (3)
C4—H4A0.9700C13—H130.9300
C4—H4B0.9700C14—C151.374 (3)
C5—C61.379 (3)C14—H140.9300
C5—C101.388 (3)C15—C161.364 (3)
C6—C71.382 (3)C15—H150.9300
C6—H60.9300C16—C171.373 (3)
C7—C81.376 (3)C16—H160.9300
C7—H70.9300C17—H170.9300
C2—O1—H1109.5C8—C9—C10120.2 (2)
C3—N1—C4112.56 (14)C8—C9—H9119.9
C3—N1—C11116.14 (13)C10—C9—H9119.9
C4—N1—C11113.86 (15)C9—C10—C5121.00 (19)
C2—C1—C3120.24 (17)C9—C10—H10119.5
C2—C1—Cl1118.11 (13)C5—C10—H10119.5
C3—C1—Cl1121.65 (13)N1—C11—C12112.48 (16)
O1—C2—C3i119.62 (15)N1—C11—H11A109.1
O1—C2—C1119.03 (16)C12—C11—H11A109.1
C3i—C2—C1121.35 (15)N1—C11—H11B109.1
C2i—C3—C1118.41 (15)C12—C11—H11B109.1
C2i—C3—N1115.12 (14)H11A—C11—H11B107.8
C1—C3—N1126.39 (16)C13—C12—C17117.0 (2)
N1—C4—C5114.33 (15)C13—C12—C11121.51 (17)
N1—C4—H4A108.7C17—C12—C11121.47 (17)
C5—C4—H4A108.7C14—C13—C12121.4 (2)
N1—C4—H4B108.7C14—C13—H13119.3
C5—C4—H4B108.7C12—C13—H13119.3
H4A—C4—H4B107.6C13—C14—C15120.5 (2)
C6—C5—C10118.10 (18)C13—C14—H14119.8
C6—C5—C4119.15 (17)C15—C14—H14119.8
C10—C5—C4122.69 (17)C16—C15—C14119.2 (2)
C5—C6—C7120.8 (2)C16—C15—H15120.4
C5—C6—H6119.6C14—C15—H15120.4
C7—C6—H6119.6C15—C16—C17120.4 (2)
C8—C7—C6120.3 (2)C15—C16—H16119.8
C8—C7—H7119.8C17—C16—H16119.8
C6—C7—H7119.8C16—C17—C12121.5 (2)
C9—C8—C7119.6 (2)C16—C17—H17119.2
C9—C8—H8120.2C12—C17—H17119.2
C7—C8—H8120.2
C3—C1—C2—O1179.49 (16)C5—C6—C7—C80.1 (3)
Cl1—C1—C2—O10.5 (2)C6—C7—C8—C90.7 (3)
C3—C1—C2—C3i0.0 (3)C7—C8—C9—C101.2 (3)
Cl1—C1—C2—C3i179.99 (14)C8—C9—C10—C50.8 (3)
C2—C1—C3—C2i0.0 (3)C6—C5—C10—C90.0 (3)
Cl1—C1—C3—C2i179.99 (14)C4—C5—C10—C9177.01 (19)
C2—C1—C3—N1176.65 (16)C3—N1—C11—C1264.7 (2)
Cl1—C1—C3—N13.4 (3)C4—N1—C11—C12162.09 (15)
C4—N1—C3—C2i106.89 (19)N1—C11—C12—C1380.0 (2)
C11—N1—C3—C2i119.33 (17)N1—C11—C12—C17101.1 (2)
C4—N1—C3—C169.8 (2)C17—C12—C13—C140.5 (3)
C11—N1—C3—C163.9 (2)C11—C12—C13—C14178.5 (2)
C3—N1—C4—C5157.91 (16)C12—C13—C14—C150.1 (4)
C11—N1—C4—C567.2 (2)C13—C14—C15—C160.0 (4)
N1—C4—C5—C6157.34 (17)C14—C15—C16—C170.3 (4)
N1—C4—C5—C1025.7 (3)C15—C16—C17—C120.8 (3)
C10—C5—C6—C70.4 (3)C13—C12—C17—C160.8 (3)
C4—C5—C6—C7176.68 (19)C11—C12—C17—C16178.1 (2)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1i0.822.202.680 (2)117
Symmetry code: (i) x+1, y+1, z+1.
Selected bond lengths (Å) for (1a) and (1b) top
Parameter(1a)(1b)
O1—C21.365 (2)1.367 (2)
C2—C31.395 (3)1.389 (3)
C1—C31.391 (3)1.402 (2)
C1—C21.389 (3)1.393 (2)
C3—N11.443 (2)1.440 (2)
C1—Cl11.7309 (19)1.7280 (19)
Parameters (°) for important angles and the dihedral angles in (1a) and (1b)
HQ, Ph1 are Ph2 are the planes of the central C1–C3/C1i–C3i arene, the C5–C10 phenyl ring and the C12–C17 phenyl ring, respectively [symmetry code: (i) -x+1, -y+1, -z+1]. [OK?]
top
Parameter(1a)(1b)
C3—N1—C11116.86 (15)116.14 (13)
C3—N1—C4112.92 (14)112.56 (14)
N1—C4—C5111.72 (16)114.33 (15)
N1—C11—C12113.74 (16)112.48 (16)
HQ—Ph111.9 (2)43.6 (2)
HQ—Ph274.0 (2)65.4 (2)
Ph1—Ph262.12 (13)25.63 (10)
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds