Analysis of structures with saturated hydrogen bonding

Loehlin, J.H.; Okasako, E.L.N.

doi:10.1107/S0108768106045046

Analysis of structures with saturated hydrogen bonding

All simple structures with saturated hydrogen bonding (SHB) are classified into eight categories on the basis of the donor and acceptor numbers on the atoms at each end of the hydrogen bonds. Examples from the literature are included where known, along with seven structures investigated as part of this study (five have SHB). Graph-set descriptions of the hydrogen-bond patterns are given for each of these structures and for some selected literature examples. The structures presented are: piperazine (I), morpholinium chloride (II) and iodide (III) [(II) and (III) are not SHB], three 1:1 cocrystals of diols with 1,4-phenylenediamine (PDA) - PDA·1,8-octane diol (IV), PDA·1,10-decane diol (V), and PDA·1,12-dodecane diol (VI) and 6-amino-1-hexanol (VII). This study discusses some structures that show limitations of the graph-set model, along with possible suggestions to cover these limitations. The cocrystalline PDA·aliphatic diol structures may provide details applicable to the structure of self-assembled monolayers of aliphatic thiol molecules on Au(111) surfaces.

Keywords: saturated hydrogen bonding; graph-set description.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768106045046/gp5014sup1.cif Contains datablocks CRYSTALS, PZ, MORPHI, PDA8DO, PDA10D, PDA12D, AMHXOL, MORFCL
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768106045046/gp5014PZsup2.hkl Contains datablock PZ
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768106045046/gp5014MORFCLsup3.hkl Contains datablock MORFCL
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768106045046/gp5014MORPHIsup4.hkl Contains datablock MORPHI
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768106045046/gp5014PDA8DOsup5.hkl Contains datablock PDA8DO
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768106045046/gp5014PDA10Dsup6.hkl Contains datablock PDA10D
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768106045046/gp5014PDA12Dsup7.hkl Contains datablock PDA12D
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768106045046/gp5014AMHXOLsup8.hkl Contains datablock AMHXOL

CCDC references: 637753; 637754; 637755; 637756; 637757; 637758; 637759

Experimental top

One equivalent of dilute HCl was added to morpholine

Computing details top

Data collection: EXPRESS for PZ; Bruker SMART CCD for MORFCL, PDA8DO, PDA10D, PDA12D; EXPRESS (Enraf-Nonius, 1993) for MORPHI; Siemens XSCANS for AMHXOL. Cell refinement: EXPRESS for PZ; SAINT for MORFCL, PDA8DO, PDA10D, PDA12D; EXPRESS (Enraf-Nonius, 1993) for MORPHI; XSCANS for AMHXOL. Data reduction: Xtal3.7 for PZ; SAINT for MORFCL, PDA8DO, PDA10D, PDA12D; EXPRESS (Enraf-Nonius, 1993) for MORPHI; Siemens SHELXTL for AMHXOL. Program(s) used to solve structure: model ring fit on i, H-bond chain along 21 axis for PZ; SIR92 (Altomare et al., 1994) for MORFCL, MORPHI, PDA8DO, PDA10D, PDA12D; SHELXS 86 (Sheldrick, 1986) for AMHXOL. Program(s) used to refine structure: Xtal CRYLSQ for PZ; CRYSTALS (Watkin et al. 2001) for MORFCL, MORPHI, PDA8DO, PDA10D, PDA12D, AMHXOL. Molecular graphics: Xtal ORTEP for PZ; CAMERON (Watkin et al. 1996) for MORFCL, MORPHI, PDA8DO, PDA10D, PDA12D, AMHXOL. Software used to prepare material for publication: Xtal BONDLA CIFIO for PZ; CRYSTALS (Watkin et al. 2001) for MORFCL, MORPHI, PDA8DO, PDA10D, PDA12D, AMHXOL.

Figures top

(PZ) piperazine top

Crystal data top

C₄H₁₀N₂	F(000) = 96
M_r = 86.14	D_x = 1.114 Mg m⁻³
Monoclinic, P2₁/n	Melting point: not measured K
Hall symbol: -p 2yn	Cu Kα radiation, λ = 1.5418 Å
a = 6.0817 (12) Å	Cell parameters from 25 reflections
b = 5.2501 (4) Å	θ = 36–50°
c = 8.4646 (14) Å	µ = 0.55 mm⁻¹
β = 108.207 (14)°	T = 293 K
V = 256.74 (7) Å³	Prism, colorless
Z = 2	0.60 × 0.35 × 0.25 mm

Data collection top

CAD4 diffractometer	424 reflections with I > 2.00u(I)
Radiation source: xray tube	R_int = 0.02
Graphite monochromator	θ_max = 76.7°, θ_min = 7.9°
ω scan	h = −7→7
Absorption correction: for a cylinder mounted on the ϕ axis psi scans	k = 0→6
T_min = 0.77, T_max = 0.87	l = 0→10
535 measured reflections	3 standard reflections every 120 min
453 independent reflections	intensity decay: 0.2%

Refinement top

Refinement on F²	Method = Prince modified Chebychev polynomial, (Watkin, 1994) W = [weight] * [1-(deltaF/6*sigmaF)^2]2 0.140E + 04 0.222E + 04 0.125E + 04 385.
R[F² > 2σ(F²)] = 0.046	(Δ/σ)_max = 0.000139
wR(F²) = 0.111	Δρ_max = 0.17 e Å⁻³
S = 1.04	Δρ_min = −0.10 e Å⁻³
424 reflections	Extinction correction: Larson 1970 Crystallographic Computing eq 22
33 parameters	Extinction coefficient: 68.7 (48)
H atoms treated by a mixture of independent and constrained refinement

Crystal data top

C₄H₁₀N₂	V = 256.74 (7) Å³
M_r = 86.14	Z = 2
Monoclinic, P2₁/n	Cu Kα radiation
a = 6.0817 (12) Å	µ = 0.55 mm⁻¹
b = 5.2501 (4) Å	T = 293 K
c = 8.4646 (14) Å	0.60 × 0.35 × 0.25 mm
β = 108.207 (14)°

Data collection top

CAD4 diffractometer	424 reflections with I > 2.00u(I)
Absorption correction: for a cylinder mounted on the ϕ axis psi scans	R_int = 0.02
T_min = 0.77, T_max = 0.87	3 standard reflections every 120 min
535 measured reflections	intensity decay: 0.2%
453 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	33 parameters
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.17 e Å⁻³
424 reflections	Δρ_min = −0.10 e Å⁻³

Special details top

Experimental. crystals are very hygroscopic, transferred under dry N2 blanket and sealed in glass capillary

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.3631 (2)	0.1225 (2)	0.35460 (14)	0.0531
C2	0.6083 (3)	0.0807 (4)	0.38357 (18)	0.0585
C3	0.6820 (3)	−0.1576 (3)	0.4868 (2)	0.0543
H21	0.6979 (3)	0.2299 (4)	0.44433 (18)	0.0713*
H22	0.6384 (3)	0.0595 (4)	0.27475 (18)	0.0713*
H31	0.8509 (3)	−0.1887 (3)	0.5074 (2)	0.0645*
H32	0.5914 (3)	−0.3066 (3)	0.4266 (2)	0.0645*
H1	0.319 (4)	0.262 (6)	0.295 (2)	0.082 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0588 (9)	0.0459 (8)	0.0417 (8)	0.0019 (5)	−0.0031 (6)	0.0048 (3)
C2	0.0704 (12)	0.053 (1)	0.058 (1)	−0.0004 (7)	0.0288 (8)	0.0074 (6)
C3	0.0497 (9)	0.047 (1)	0.065 (1)	0.0053 (5)	0.0163 (7)	−0.0003 (6)

Geometric parameters (Å, º) top

N1—C2	1.450 (2)	C2—H21	1.000
N1—C3ⁱ	1.4634 (18)	C2—H22	1.000
N1—H1	0.88 (3)	C3—H31	1.000
C2—C3	1.512 (2)	C3—H32	1.000

C2—N1—C3ⁱ	110.0 (1)	H21—C2—H22	109.467
C2—N1—H1	109.4 (14)	N1ⁱ—C3—C2	108.61 (12)
C3ⁱ—N1—H1	108.1 (13)	N1ⁱ—C3—H31	109.72 (7)
N1—C2—C3	109.05 (13)	C2—C3—H31	109.81 (9)
N1—C2—H21	109.59 (9)	N1ⁱ—C3—H32	109.58 (8)
C3—C2—H21	109.59 (9)	C2—C3—H32	109.64 (9)
N1—C2—H22	109.63 (8)	H31—C3—H32	109.467
C3—C2—H22	109.50 (9)

Symmetry code: (i) −x+1, −y, −z+1.

(MORFCL) Morpholinium Chloride top

Crystal data top

C₄H₁₀ClNO	D_x = 1.355 Mg m⁻³
M_r = 123.58	Melting point: not measured K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.7360 (16) Å	Cell parameters from 1463 reflections
b = 10.618 (3) Å	θ = 2.8–28.3°
c = 10.142 (3) Å	µ = 0.52 mm⁻¹
β = 101.197 (5)°	T = 213 K
V = 605.9 (3) Å³	Plate, colorless
Z = 4	0.12 × 0.10 × 0.08 mm
F(000) = 264.000

Data collection top

Bruker SMART CCD diffractometer	R_int = 0.06
Graphite monochromator	θ_max = 28.3°, θ_min = 2.8°
ω/2θ scans	h = −7→7
4061 measured reflections	k = −14→14
1463 independent reflections	l = −8→13
1152 reflections with I > 3.00u(I)

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.083	Method = Prince modified Chebychev polynomial, (Watkin, 1994) W = [weight] * [1-(deltaF/6*sigmaF)^2]2 26.1 38.6 20.8 4.87
S = 0.96	(Δ/σ)_max = 0.010
1152 reflections	Δρ_max = 0.48 e Å⁻³
70 parameters	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₄H₁₀ClNO	V = 605.9 (3) Å³
M_r = 123.58	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.7360 (16) Å	µ = 0.52 mm⁻¹
b = 10.618 (3) Å	T = 213 K
c = 10.142 (3) Å	0.12 × 0.10 × 0.08 mm
β = 101.197 (5)°

Data collection top

Bruker SMART CCD diffractometer	1152 reflections with I > 3.00u(I)
4061 measured reflections	R_int = 0.06
1463 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	70 parameters
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Δρ_max = 0.48 e Å⁻³
1152 reflections	Δρ_min = −0.25 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.7568 (3)	0.10418 (14)	0.04171 (12)	0.0376
C2	0.8146 (4)	0.20882 (19)	0.13083 (18)	0.0374
C3	0.6726 (3)	0.20495 (16)	0.24100 (17)	0.0314
N4	0.7152 (2)	0.08438 (14)	0.31597 (13)	0.0243
C5	0.6741 (3)	−0.02534 (15)	0.22235 (16)	0.0304
C6	0.8161 (4)	−0.00982 (19)	0.11312 (17)	0.0364
Cl7	0.25380 (7)	0.12399 (5)	0.43960 (4)	0.0339
H21	0.9878 (4)	0.20574 (19)	0.17179 (18)	0.0442*
H22	0.7787 (4)	0.28880 (19)	0.07879 (18)	0.0442*
H31	0.7218 (3)	0.27669 (16)	0.30417 (17)	0.0369*
H32	0.4997 (3)	0.21266 (16)	0.20075 (17)	0.0369*
H51	0.7241 (3)	−0.10453 (15)	0.27343 (16)	0.0358*
H52	0.5012 (3)	−0.03038 (15)	0.18105 (16)	0.0358*
H61	0.9892 (4)	−0.00909 (19)	0.15446 (17)	0.0439*
H62	0.7816 (4)	−0.08216 (19)	0.04916 (17)	0.0439*
H1	0.629 (5)	0.075 (2)	0.377 (2)	0.0459*
H2	0.864 (5)	0.083 (2)	0.364 (2)	0.0402*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0461 (8)	0.0465 (8)	0.0205 (6)	−0.0014 (6)	0.0073 (6)	0.0007 (5)
C2	0.045 (1)	0.036 (1)	0.0307 (9)	−0.0083 (8)	0.0055 (8)	0.0093 (7)
C3	0.0342 (9)	0.0273 (9)	0.0311 (8)	0.0072 (6)	0.0022 (7)	−0.0018 (6)
N4	0.0220 (6)	0.0311 (7)	0.0205 (6)	−0.0021 (5)	0.0054 (5)	0.0006 (5)
C5	0.0366 (9)	0.0246 (9)	0.0290 (8)	−0.0064 (6)	0.0039 (7)	0.0001 (6)
C6	0.042 (1)	0.038 (1)	0.0306 (8)	0.0054 (8)	0.0097 (7)	−0.0078 (7)
Cl7	0.0206 (2)	0.0510 (3)	0.0303 (2)	0.00171 (16)	0.00555 (14)	0.00761 (18)

Geometric parameters (Å, º) top

O1—C2	1.430 (2)	N4—C5	1.492 (2)
O1—C6	1.418 (2)	N4—H1	0.87 (3)
C2—C3	1.505 (3)	N4—H2	0.90 (3)
C2—H21	1.000	C5—C6	1.506 (2)
C2—H22	1.000	C5—H51	1.000
C3—N4	1.485 (2)	C5—H52	1.000
C3—H31	1.000	C6—H61	1.000
C3—H32	1.000	C6—H62	1.000

C2—O1—C6	109.71 (13)	C3—N4—H2	109.9 (16)
O1—C2—C3	110.82 (15)	C5—N4—H2	110.4 (15)
O1—C2—H21	109.08 (11)	H1—N4—H2	103 (2)
C3—C2—H21	109.1 (1)	N4—C5—C6	109.95 (14)
O1—C2—H22	109.12 (9)	N4—C5—H51	109.44 (8)
C3—C2—H22	109.2 (1)	C6—C5—H51	109.3 (1)
H21—C2—H22	109.467	N4—C5—H52	109.26 (9)
C2—C3—N4	110.15 (14)	C6—C5—H52	109.4 (1)
C2—C3—H31	109.2 (1)	H51—C5—H52	109.467
N4—C3—H31	109.32 (8)	O1—C6—C5	111.02 (15)
C2—C3—H32	109.4 (1)	O1—C6—H61	109.1 (1)
N4—C3—H32	109.35 (9)	C5—C6—H61	109.1 (1)
H31—C3—H32	109.467	O1—C6—H62	109.08 (9)
C3—N4—C5	110.93 (12)	C5—C6—H62	109.0 (1)
C3—N4—H1	113.5 (17)	H61—C6—H62	109.467
C5—N4—H1	109.0 (17)

(MORPHI) morpholinium iodide top

Crystal data top

C₄H₁₀INO	D_x = 2.022 Mg m⁻³
M_r = 215.03	Melting point: not measured K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.6521 (3) Å	Cell parameters from 25 reflections
b = 10.4682 (8) Å	θ = 18–22°
c = 10.2590 (4) Å	µ = 4.44 mm⁻¹
β = 98.703 (4)°	T = 294 K
V = 706.17 (7) Å³	Plate, colorless
Z = 4	0.66 × 0.26 × 0.08 mm
F(000) = 408.000

Data collection top

Enraf-Nonius CAD-4 diffractometer	R_int = 0.01
Graphite monochromator	θ_max = 26.3°, θ_min = 2.8°
ω/2θ scans	h = −8→8
Absorption correction: ψ scan Azimutal absorption correction (North et al, 1968)	k = −13→0
T_min = 0.39, T_max = 0.70	l = −12→0
1600 measured reflections	3 standard reflections every 0 reflections
1519 independent reflections	intensity decay: 0.0%
1323 reflections with I > 2.00u(I)

Refinement top

Refinement on F	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.018	Method = Prince modified Chebychev polynomial, (Watkin, 1994) W = [weight] * [1-(deltaF/6*sigmaF)^2]2 0.710 -0.154 0.397 -0.143 0.253E-01
wR(F²) = 0.019	(Δ/σ)_max = 0.002
S = 1.11	Δρ_max = 0.70 e Å⁻³
1323 reflections	Δρ_min = −0.49 e Å⁻³
73 parameters	Extinction correction: Larson 1970 Crystallographic Computing eq 22
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 80.2 (19)

Crystal data top

C₄H₁₀INO	V = 706.17 (7) Å³
M_r = 215.03	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.6521 (3) Å	µ = 4.44 mm⁻¹
b = 10.4682 (8) Å	T = 294 K
c = 10.2590 (4) Å	0.66 × 0.26 × 0.08 mm
β = 98.703 (4)°

Data collection top

Enraf-Nonius CAD-4 diffractometer	1323 reflections with I > 2.00u(I)
Absorption correction: ψ scan Azimutal absorption correction (North et al, 1968)	R_int = 0.01
T_min = 0.39, T_max = 0.70	3 standard reflections every 0 reflections
1600 measured reflections	intensity decay: 0.0%
1519 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.018	73 parameters
wR(F²) = 0.019	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.70 e Å⁻³
1323 reflections	Δρ_min = −0.49 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.7158 (3)	0.0872 (2)	0.7922 (2)	0.0359
C2	0.6806 (4)	0.2107 (2)	0.7220 (3)	0.0449
C3	0.8000 (5)	0.2150 (3)	0.6080 (3)	0.0494
O4	0.7465 (3)	0.11048 (17)	0.52046 (17)	0.0494
C5	0.7959 (5)	−0.0062 (3)	0.5876 (3)	0.0504
C6	0.6772 (4)	−0.0235 (2)	0.7002 (3)	0.0466
I7	0.24388 (2)	0.115476 (16)	0.914979 (17)	0.0436
H21	0.7176 (4)	0.2829 (2)	0.7848 (3)	0.0513*
H22	0.5332 (4)	0.2167 (2)	0.6842 (3)	0.0513*
H31	0.9476 (5)	0.2073 (3)	0.6448 (3)	0.0654*
H32	0.7755 (5)	0.2978 (3)	0.5596 (3)	0.0654*
H51	0.9435 (5)	−0.0041 (3)	0.6254 (3)	0.0594*
H52	0.7694 (5)	−0.0796 (3)	0.5250 (3)	0.0594*
H61	0.7121 (4)	−0.1062 (2)	0.7470 (3)	0.0532*
H62	0.5294 (4)	−0.0229 (2)	0.6627 (3)	0.0532*
H7	0.827 (5)	0.086 (3)	0.832 (3)	0.040 (7)*
H10	0.640 (5)	0.080 (3)	0.851 (3)	0.055 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.034 (1)	0.0457 (11)	0.0286 (9)	−0.0031 (8)	0.0072 (8)	0.0018 (8)
C2	0.0530 (14)	0.0405 (13)	0.0415 (13)	0.0073 (11)	0.0078 (11)	−0.001 (1)
C3	0.0670 (17)	0.0407 (14)	0.0411 (13)	−0.0053 (12)	0.0103 (12)	0.0063 (11)
O4	0.0668 (13)	0.0525 (11)	0.0290 (9)	−0.0003 (8)	0.0077 (8)	0.0007 (7)
C5	0.0673 (17)	0.0453 (14)	0.0407 (13)	0.0036 (12)	0.0145 (12)	−0.0042 (11)
C6	0.0546 (15)	0.0395 (13)	0.0464 (13)	−0.0092 (11)	0.0094 (11)	−0.0015 (11)
I7	0.03072 (11)	0.04955 (13)	0.05061 (13)	0.00162 (6)	0.00685 (7)	0.01399 (7)

Geometric parameters (Å, º) top

N1—C2	1.481 (3)	C3—H31	1.000
N1—C6	1.493 (3)	C3—H32	1.000
N1—H7	0.79 (3)	O4—C5	1.416 (3)
N1—H10	0.84 (3)	C5—C6	1.505 (4)
C2—C3	1.510 (4)	C5—H51	1.000
C2—H21	1.000	C5—H52	1.000
C2—H22	1.000	C6—H61	1.000
C3—O4	1.426 (3)	C6—H62	1.000

C2—N1—C6	111.8 (2)	O4—C3—H32	110.23 (13)
C2—N1—H7	110 (2)	H31—C3—H32	109.467
C6—N1—H7	112 (2)	C3—O4—C5	109.7 (2)
C2—N1—H10	111 (2)	O4—C5—C6	111.5 (2)
C6—N1—H10	109 (2)	O4—C5—H51	108.13 (15)
H7—N1—H10	104 (3)	C6—C5—H51	107.66 (16)
N1—C2—C3	109.8 (2)	O4—C5—H52	110.19 (13)
N1—C2—H21	109.92 (13)	C6—C5—H52	109.78 (15)
C3—C2—H21	111.70 (15)	H51—C5—H52	109.467
N1—C2—H22	108.50 (14)	N1—C6—C5	109.4 (2)
C3—C2—H22	107.33 (16)	N1—C6—H61	111.32 (13)
H21—C2—H22	109.467	C5—C6—H61	111.24 (15)
C2—C3—O4	110.8 (2)	N1—C6—H62	107.63 (14)
C2—C3—H31	107.85 (16)	C5—C6—H62	107.67 (16)
O4—C3—H31	108.30 (15)	H61—C6—H62	109.467
C2—C3—H32	110.18 (14)

(PDA8DO) 1,4-phenylenediamine.1,8-octanediol (1/1) top

Crystal data top

C₆H₈N₂·C₈H₁₈O₂	D_x = 1.131 Mg m⁻³
M_r = 254.37	Melting point: not measured K
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 36.190 (6) Å	Cell parameters from 1776 reflections
b = 5.1258 (8) Å	θ = 1.2–27.9°
c = 8.2222 (13) Å	µ = 0.08 mm⁻¹
β = 101.773 (5)°	T = 293 K
V = 1493.2 (4) Å³	Prism, colorless
Z = 4	0.75 × 0.30 × 0.25 mm
F(000) = 560.000

Data collection top

Bruker CCD diffractometer	R_int = 0.02
Graphite monochromator	θ_max = 27.9°, θ_min = 1.2°
ω/2θ scans	h = −47→44
5234 measured reflections	k = −6→6
1776 independent reflections	l = −7→10
1087 reflections with I > 3.00u(I)

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.038	Method = Prince modified Chebychev polynomial, (Watkin, 1994) W = [weight] * [1-(deltaF/6*sigmaF)^2]2 6.89 9.46 3.19
wR(F²) = 0.094	(Δ/σ)_max = 0.000289
S = 1.03	Δρ_max = 0.24 e Å⁻³
1087 reflections	Δρ_min = −0.27 e Å⁻³
95 parameters	Extinction correction: Larson 1970 Crystallographic Computing eq 22
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 190.0 (78)

Crystal data top

C₆H₈N₂·C₈H₁₈O₂	V = 1493.2 (4) Å³
M_r = 254.37	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 36.190 (6) Å	µ = 0.08 mm⁻¹
b = 5.1258 (8) Å	T = 293 K
c = 8.2222 (13) Å	0.75 × 0.30 × 0.25 mm
β = 101.773 (5)°

Data collection top

Bruker CCD diffractometer	1087 reflections with I > 3.00u(I)
5234 measured reflections	R_int = 0.02
1776 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	95 parameters
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.24 e Å⁻³
1087 reflections	Δρ_min = −0.27 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.32792 (3)	0.2021 (3)	1.00887 (18)	0.0448
C2	0.28841 (4)	0.2226 (3)	1.00136 (15)	0.0346
C3	0.26785 (4)	0.4209 (3)	0.91157 (17)	0.0391
C4	0.22977 (4)	0.4478 (3)	0.91022 (17)	0.0391
O5	0.35756 (3)	0.3484 (3)	0.68578 (16)	0.0546
C6	0.39484 (4)	0.4139 (3)	0.7663 (2)	0.0476
C7	0.41645 (4)	0.1679 (3)	0.8227 (2)	0.0471
C8	0.45699 (4)	0.2208 (3)	0.9096 (2)	0.0482
C9	0.47959 (4)	−0.0260 (3)	0.9577 (2)	0.0488
H31	0.28063 (4)	0.5466 (3)	0.84806 (17)	0.0484*
H41	0.21513 (4)	0.5911 (3)	0.84384 (17)	0.0469*
H61	0.40752 (4)	0.5104 (3)	0.6873 (2)	0.0578*
H62	0.39414 (4)	0.5263 (3)	0.8651 (2)	0.0578*
H71	0.41672 (4)	0.0570 (3)	0.7229 (2)	0.0564*
H72	0.40328 (4)	0.0726 (3)	0.9006 (2)	0.0564*
H81	0.46965 (4)	0.3252 (3)	0.8339 (2)	0.0573*
H82	0.45663 (4)	0.3234 (3)	1.0127 (2)	0.0573*
H91	0.47944 (4)	−0.1304 (3)	0.8549 (2)	0.0581*
H92	0.46723 (4)	−0.1284 (3)	1.0354 (2)	0.0581*
H1	0.3340 (5)	0.230 (4)	0.913 (3)	0.057 (6)*
H2	0.3479 (5)	0.492 (4)	0.629 (3)	0.055 (5)*
H3	0.3376 (5)	0.041 (4)	1.052 (3)	0.059 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0327 (6)	0.0516 (8)	0.0484 (7)	−0.0016 (5)	0.0042 (5)	−0.0038 (6)
C2	0.0333 (6)	0.0354 (7)	0.0331 (6)	−0.0038 (5)	0.0018 (5)	−0.0065 (5)
C3	0.0420 (7)	0.0362 (7)	0.0391 (7)	−0.0054 (5)	0.0083 (5)	0.0022 (5)
C4	0.0422 (7)	0.0356 (6)	0.0370 (6)	0.0023 (6)	0.0023 (5)	0.0036 (5)
O5	0.0348 (6)	0.0534 (7)	0.0681 (7)	0.0012 (5)	−0.0069 (5)	0.0157 (6)
C6	0.0346 (7)	0.0483 (8)	0.0555 (9)	0.0025 (6)	−0.0013 (6)	0.0097 (7)
C7	0.0322 (7)	0.0483 (8)	0.0576 (9)	0.0057 (6)	0.0018 (6)	0.0058 (7)
C8	0.0329 (7)	0.0523 (9)	0.0558 (8)	0.0073 (6)	0.0007 (6)	0.0015 (7)
C9	0.0325 (7)	0.0538 (9)	0.0575 (9)	0.0087 (6)	0.0032 (6)	0.0039 (7)

Geometric parameters (Å, º) top

N1—C2	1.4222 (17)	C6—H61	1.000
N1—H1	0.88 (2)	C6—H62	1.000
N1—H3	0.94 (2)	C7—C8	1.520 (2)
C2—C3	1.3814 (18)	C7—H71	1.000
C2—C4ⁱ	1.386 (2)	C7—H72	1.000
C3—C4	1.3825 (19)	C8—C9	1.514 (2)
C3—H31	1.000	C8—H81	1.000
C4—H41	1.000	C8—H82	1.000
O5—C6	1.4167 (17)	C9—C9ⁱⁱ	1.523 (3)
O5—H2	0.90 (2)	C9—H91	1.000
C6—C7	1.506 (2)	C9—H92	1.000

C2—N1—H1	112.6 (13)	C6—C7—C8	112.72 (14)
C2—N1—H3	112.2 (11)	C6—C7—H71	108.35 (9)
H1—N1—H3	110.1 (17)	C8—C7—H71	108.48 (9)
N1—C2—C3	120.33 (13)	C6—C7—H72	108.71 (9)
N1—C2—C4ⁱ	120.77 (13)	C8—C7—H72	109.07 (9)
C3—C2—C4ⁱ	118.84 (12)	H71—C7—H72	109.467
C2—C3—C4	120.35 (12)	C7—C8—C9	113.07 (13)
C2—C3—H31	119.79 (8)	C7—C8—H81	108.91 (9)
C4—C3—H31	119.86 (8)	C9—C8—H81	108.54 (9)
C2ⁱ—C4—C3	120.81 (13)	C7—C8—H82	108.30 (9)
C2ⁱ—C4—H41	119.58 (8)	C9—C8—H82	108.5 (1)
C3—C4—H41	119.61 (8)	H81—C8—H82	109.467
C6—O5—H2	106.3 (12)	C8—C9—C9ⁱⁱ	113.28 (18)
O5—C6—C7	109.32 (13)	C8—C9—H91	108.5 (1)
O5—C6—H61	109.46 (8)	C9ⁱⁱ—C9—H91	108.46 (13)
C7—C6—H61	109.64 (9)	C8—C9—H92	108.50 (9)
O5—C6—H62	109.67 (9)	C9ⁱⁱ—C9—H92	108.61 (13)
C7—C6—H62	109.27 (9)	H91—C9—H92	109.467
H61—C6—H62	109.467

Symmetry codes: (i) −x+1/2, −y+1/2, −z+2; (ii) −x+1, −y, −z+2.

(PDA10D) 1,4-phenylenediamine.1,10-decanediol (1/1) top

Crystal data top

C₆H₈N₂·C₁₀H₂₂O₂	D_x = 1.155 Mg m⁻³
M_r = 282.43	Melting point: not measured K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.453 (2) Å	Cell parameters from 2017 reflections
b = 5.1589 (6) Å	θ = 1.1–28.3°
c = 8.180 (1) Å	µ = 0.08 mm⁻¹
β = 98.398 (3)°	T = 293 K
V = 812.08 (17) Å³	Prism, colorless
Z = 2	0.35 × 0.30 × 0.05 mm
F(000) = 312.000

Data collection top

Bruker CCD diffractometer	R_int = 0.03
Graphite monochromator	θ_max = 28.3°, θ_min = 1.1°
ω/2θ scans	h = −25→24
5982 measured reflections	k = −6→6
2017 independent reflections	l = −7→10
1051 reflections with I > 3.00u(I)

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.090	Method = Prince modified Chebychev polynomial, (Watkin, 1994) W = [weight] * [1-(deltaF/6*sigmaF)^2]2 94.7 149. 108. 43.5 17.7
S = 0.94	(Δ/σ)_max = 0.007
1051 reflections	Δρ_max = 0.24 e Å⁻³
103 parameters	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₆H₈N₂·C₁₀H₂₂O₂	V = 812.08 (17) Å³
M_r = 282.43	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 19.453 (2) Å	µ = 0.08 mm⁻¹
b = 5.1589 (6) Å	T = 293 K
c = 8.180 (1) Å	0.35 × 0.30 × 0.05 mm
β = 98.398 (3)°

Data collection top

Bruker CCD diffractometer	1051 reflections with I > 3.00u(I)
5982 measured reflections	R_int = 0.03
2017 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	103 parameters
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	Δρ_max = 0.24 e Å⁻³
1051 reflections	Δρ_min = −0.28 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.46909 (8)	0.1762 (3)	0.09427 (19)	0.0259
C2	0.53927 (8)	0.1945 (3)	0.08303 (19)	0.0259
C3	0.57079 (7)	0.0194 (3)	−0.01116 (18)	0.0226
N4	0.64393 (7)	0.0308 (3)	−0.01786 (19)	0.0284
C5	0.01700 (8)	−0.3690 (3)	0.0222 (2)	0.0262
C6	0.09147 (8)	−0.3906 (3)	0.1107 (2)	0.0260
C7	0.12608 (8)	−0.1283 (3)	0.1508 (2)	0.0264
C8	0.20076 (8)	−0.1516 (3)	0.2385 (2)	0.0259
C9	0.23361 (8)	0.1105 (3)	0.2825 (2)	0.0274
O10	0.30307 (6)	0.0721 (2)	0.35958 (16)	0.0337
H1	0.6530 (9)	0.002 (4)	−0.119 (3)	0.034 (5)*
H2	0.661 (1)	0.180 (4)	0.013 (3)	0.043 (6)*
H3	0.318 (1)	0.210 (5)	0.407 (3)	0.045 (6)*
H11	0.44708 (8)	0.3043 (3)	0.16242 (19)	0.0310*
H21	0.56755 (8)	0.3359 (3)	0.14358 (19)	0.0306*
H51	−0.01128 (8)	−0.2748 (3)	0.0959 (2)	0.0308*
H52	0.01742 (8)	−0.2678 (3)	−0.0819 (2)	0.0308*
H61	0.09091 (8)	−0.4875 (3)	0.2164 (2)	0.0306*
H62	0.11946 (8)	−0.4893 (3)	0.0383 (2)	0.0306*
H71	0.09836 (8)	−0.0301 (3)	0.2239 (2)	0.0308*
H72	0.12640 (8)	−0.0308 (3)	0.0453 (2)	0.0308*
H81	0.20077 (8)	−0.2540 (3)	0.3423 (2)	0.0306*
H82	0.22901 (8)	−0.2442 (3)	0.1640 (2)	0.0306*
H91	0.20678 (8)	0.2031 (3)	0.3601 (2)	0.0321*
H92	0.23338 (8)	0.2161 (3)	0.1800 (2)	0.0321*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0261 (8)	0.0241 (8)	0.0271 (8)	0.0032 (6)	0.0025 (6)	−0.0026 (6)
C2	0.0271 (8)	0.0225 (8)	0.0268 (7)	−0.0030 (6)	−0.0006 (6)	−0.0030 (7)
C3	0.0202 (7)	0.0224 (8)	0.0240 (7)	0.0021 (6)	−0.0008 (5)	0.0049 (6)
N4	0.0215 (7)	0.0309 (8)	0.0323 (8)	−0.0002 (6)	0.0024 (5)	0.0012 (7)
C5	0.0201 (8)	0.0251 (8)	0.0316 (8)	−0.0026 (6)	−0.0019 (6)	−0.0022 (7)
C6	0.0205 (7)	0.0255 (8)	0.0306 (8)	−0.0025 (6)	−0.0011 (6)	−0.0019 (6)
C7	0.0217 (8)	0.0256 (8)	0.0299 (8)	−0.0028 (6)	−0.0031 (6)	−0.0017 (7)
C8	0.0195 (7)	0.0252 (8)	0.0316 (8)	−0.0025 (6)	−0.0013 (6)	−0.0015 (7)
C9	0.0194 (7)	0.0264 (9)	0.0344 (8)	−0.0015 (6)	−0.0027 (6)	−0.0034 (7)
O10	0.0228 (6)	0.0273 (7)	0.0470 (7)	−0.0029 (5)	−0.0083 (5)	−0.0074 (6)

Geometric parameters (Å, º) top

C1—C2	1.385 (2)	C6—H61	1.000
C1—C3ⁱ	1.389 (2)	C6—H62	1.000
C1—H11	1.000	C7—C8	1.528 (2)
C2—C3	1.387 (2)	C7—H71	1.000
C2—H21	1.000	C7—H72	1.000
C3—N4	1.4330 (19)	C8—C9	1.516 (2)
N4—H1	0.88 (2)	C8—H81	1.000
N4—H2	0.86 (2)	C8—H82	1.000
C5—C5ⁱⁱ	1.525 (3)	C9—O10	1.4189 (18)
C5—C6	1.526 (2)	C9—H91	1.000
C5—H51	1.000	C9—H92	1.000
C5—H52	1.000	O10—H3	0.84 (2)
C6—C7	1.526 (2)

C2—C1—C3ⁱ	120.18 (14)	C7—C6—H62	108.48 (9)
C2—C1—H11	119.90 (9)	H61—C6—H62	109.466
C3ⁱ—C1—H11	119.92 (9)	C6—C7—C8	113.01 (13)
C1—C2—C3	120.82 (14)	C6—C7—H71	108.57 (9)
C1—C2—H21	119.55 (9)	C8—C7—H71	108.52 (9)
C3—C2—H21	119.63 (9)	C6—C7—H72	108.60 (9)
C1ⁱ—C3—C2	119.00 (13)	C8—C7—H72	108.63 (9)
C1ⁱ—C3—N4	119.88 (14)	H71—C7—H72	109.467
C2—C3—N4	121.07 (14)	C7—C8—C9	112.35 (13)
C3—N4—H1	111.3 (12)	C7—C8—H81	108.81 (9)
C3—N4—H2	112.1 (14)	C9—C8—H81	108.76 (9)
H1—N4—H2	107.5 (19)	C7—C8—H82	108.70 (9)
C5ⁱⁱ—C5—C6	113.39 (17)	C9—C8—H82	108.71 (9)
C5ⁱⁱ—C5—H51	108.47 (12)	H81—C8—H82	109.466
C6—C5—H51	108.49 (9)	C8—C9—O10	108.78 (13)
C5ⁱⁱ—C5—H52	108.50 (12)	C8—C9—H91	109.61 (9)
C6—C5—H52	108.48 (9)	O10—C9—H91	109.66 (9)
H51—C5—H52	109.467	C8—C9—H92	109.66 (9)
C5—C6—C7	113.32 (13)	O10—C9—H92	109.65 (9)
C5—C6—H61	108.50 (9)	H91—C9—H92	109.466
C7—C6—H61	108.52 (9)	C9—O10—H3	109.0 (14)
C5—C6—H62	108.51 (9)

Symmetry codes: (i) −x+1, −y, −z; (ii) −x, −y−1, −z.

(PDA12D) 1,4-phenylenediamine.1,12-dodecanediol (1/1) top

Crystal data top

C₆H₈N₂·C₁₂H₂₆O₂	D_x = 1.098 Mg m⁻³
M_r = 310.48	Melting point: not measured K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 22.2081 (14) Å	Cell parameters from 2260 reflections
b = 5.1843 (9) Å	θ = 0.9–28.3°
c = 8.217 (4) Å	µ = 0.07 mm⁻¹
β = 96.818 (3)°	T = 293 K
V = 939.4 (5) Å³	Prism, colorless
Z = 2	0.26 × 0.18 × 0.08 mm
F(000) = 344.000

Data collection top

Bruker CCD diffractometer	R_int = 0.08
Graphite monochromator	θ_max = 28.3°, θ_min = 0.9°
ω/2θ scans	h = −23→29
6256 measured reflections	k = −6→6
2260 independent reflections	l = −10→10
1143 reflections with I > 3.00u(I)

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.037	Method = Prince modified Chebychev polynomial, (Watkin, 1994) W = [weight] * [1-(deltaF/6*sigmaF)^2]2 5.77 7.86 2.57
wR(F²) = 0.090	(Δ/σ)_max = 0.000293
S = 0.96	Δρ_max = 0.21 e Å⁻³
1143 reflections	Δρ_min = −0.20 e Å⁻³
113 parameters	Extinction correction: Larson 1970 Crystallographic Computing eq 22
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 95.4 (50)

Crystal data top

C₆H₈N₂·C₁₂H₂₆O₂	V = 939.4 (5) Å³
M_r = 310.48	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 22.2081 (14) Å	µ = 0.07 mm⁻¹
b = 5.1843 (9) Å	T = 293 K
c = 8.217 (4) Å	0.26 × 0.18 × 0.08 mm
β = 96.818 (3)°

Data collection top

Bruker CCD diffractometer	1143 reflections with I > 3.00u(I)
6256 measured reflections	R_int = 0.08
2260 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	113 parameters
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Δρ_max = 0.21 e Å⁻³
1143 reflections	Δρ_min = −0.20 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.47169 (7)	0.1707 (3)	0.59489 (19)	0.0388
C2	0.53283 (8)	0.1963 (3)	0.5808 (2)	0.0382
C3	0.56185 (7)	0.0262 (3)	0.48628 (18)	0.0337
N4	0.62553 (7)	0.0445 (4)	0.4768 (2)	0.0446
C5	0.03318 (7)	−0.5196 (4)	0.5336 (2)	0.0494
C6	0.06774 (7)	−0.2692 (4)	0.5697 (2)	0.0487
C7	0.13386 (7)	−0.3091 (4)	0.6380 (2)	0.0465
C8	0.16843 (8)	−0.0573 (4)	0.6752 (2)	0.0456
C9	0.23398 (7)	−0.1002 (4)	0.7485 (2)	0.0448
C10	0.26665 (7)	0.1486 (4)	0.7952 (2)	0.0460
O11	0.32711 (6)	0.0933 (3)	0.86189 (19)	0.0544
H11	0.45155 (7)	0.2950 (3)	0.66415 (19)	0.0455*
H21	0.55641 (8)	0.3397 (3)	0.6396 (2)	0.0445*
H51	0.03487 (7)	−0.6212 (4)	0.6375 (2)	0.0572*
H52	0.05341 (7)	−0.6191 (4)	0.4510 (2)	0.0572*
H61	0.04736 (7)	−0.1690 (4)	0.6516 (2)	0.0560*
H62	0.06637 (7)	−0.1682 (4)	0.4657 (2)	0.0560*
H71	0.13524 (7)	−0.4112 (4)	0.7416 (2)	0.0541*
H72	0.15432 (7)	−0.4082 (4)	0.5558 (2)	0.0541*
H81	0.14731 (8)	0.0446 (4)	0.7547 (2)	0.0536*
H82	0.16832 (8)	0.0424 (4)	0.5709 (2)	0.0536*
H91	0.23425 (7)	−0.2092 (4)	0.8490 (2)	0.0520*
H92	0.25587 (7)	−0.1923 (4)	0.6662 (2)	0.0520*
H101	0.24542 (7)	0.2421 (4)	0.8783 (2)	0.0534*
H102	0.26709 (7)	0.2589 (4)	0.6955 (2)	0.0534*
H1	0.641 (1)	0.193 (5)	0.507 (3)	0.062 (7)*
H2	0.6332 (11)	0.008 (5)	0.380 (4)	0.072 (8)*
H3	0.341 (1)	0.227 (5)	0.909 (3)	0.069 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0410 (9)	0.0352 (8)	0.0405 (8)	0.0053 (7)	0.0055 (7)	−0.0045 (7)
C2	0.0407 (9)	0.0343 (8)	0.0383 (8)	−0.0030 (7)	−0.0011 (6)	−0.0024 (7)
C3	0.0306 (7)	0.0352 (8)	0.0338 (7)	0.0035 (6)	−0.0022 (6)	0.0056 (6)
N4	0.0309 (7)	0.050 (1)	0.052 (1)	0.0012 (7)	0.0021 (6)	0.0024 (8)
C5	0.0324 (8)	0.052 (1)	0.0617 (11)	−0.0120 (8)	−0.0024 (8)	0.0006 (9)
C6	0.0326 (9)	0.0537 (11)	0.0578 (11)	−0.0124 (8)	−0.0029 (7)	−0.0003 (8)
C7	0.0318 (9)	0.0500 (11)	0.056 (1)	−0.0097 (7)	−0.0016 (7)	−0.0043 (9)
C8	0.0328 (8)	0.048 (1)	0.054 (1)	−0.0091 (7)	−0.0024 (7)	−0.0021 (8)
C9	0.0305 (8)	0.046 (1)	0.057 (1)	−0.0049 (7)	−0.0006 (7)	−0.0069 (8)
C10	0.0341 (9)	0.045 (1)	0.056 (1)	−0.0022 (7)	−0.0045 (7)	−0.0099 (9)
O11	0.0342 (7)	0.0531 (9)	0.0717 (9)	−0.0030 (6)	−0.0109 (6)	−0.0154 (7)

Geometric parameters (Å, º) top

C1—C2	1.383 (2)	C6—H62	1.000
C1—C3ⁱ	1.387 (2)	C7—C8	1.527 (2)
C1—H11	1.000	C7—H71	1.000
C2—C3	1.384 (2)	C7—H72	1.000
C2—H21	1.000	C8—C9	1.524 (2)
C3—N4	1.429 (2)	C8—H81	1.000
N4—H1	0.86 (3)	C8—H82	1.000
N4—H2	0.86 (3)	C9—C10	1.507 (2)
C5—C5ⁱⁱ	1.525 (3)	C9—H91	1.000
C5—C6	1.520 (2)	C9—H92	1.000
C5—H51	1.000	C10—O11	1.418 (2)
C5—H52	1.000	C10—H101	1.000
C6—C7	1.523 (2)	C10—H102	1.000
C6—H61	1.000	O11—H3	0.83 (3)

C2—C1—C3ⁱ	120.48 (15)	C6—C7—H71	108.46 (11)
C2—C1—H11	119.7 (1)	C8—C7—H71	108.6 (1)
C3ⁱ—C1—H11	119.80 (9)	C6—C7—H72	108.45 (11)
C1—C2—C3	120.87 (15)	C8—C7—H72	108.4 (1)
C1—C2—H21	119.6 (1)	H71—C7—H72	109.467
C3—C2—H21	119.51 (9)	C7—C8—C9	112.84 (16)
C1ⁱ—C3—C2	118.65 (14)	C7—C8—H81	108.6 (1)
C1ⁱ—C3—N4	120.09 (15)	C9—C8—H81	108.6 (1)
C2—C3—N4	121.21 (15)	C7—C8—H82	108.7 (1)
C3—N4—H1	113.2 (14)	C9—C8—H82	108.6 (1)
C3—N4—H2	110.1 (16)	H81—C8—H82	109.467
H1—N4—H2	111 (2)	C8—C9—C10	112.59 (16)
C5ⁱⁱ—C5—C6	113.6 (2)	C8—C9—H91	108.7 (1)
C5ⁱⁱ—C5—H51	108.42 (15)	C10—C9—H91	108.55 (11)
C6—C5—H51	108.43 (11)	C8—C9—H92	108.7 (1)
C5ⁱⁱ—C5—H52	108.44 (16)	C10—C9—H92	108.8 (1)
C6—C5—H52	108.42 (11)	H91—C9—H92	109.467
H51—C5—H52	109.467	C9—C10—O11	109.32 (16)
C5—C6—C7	113.48 (16)	C9—C10—H101	109.7 (1)
C5—C6—H61	108.47 (11)	O11—C10—H101	109.6 (1)
C7—C6—H61	108.44 (11)	C9—C10—H102	109.40 (11)
C5—C6—H62	108.48 (11)	O11—C10—H102	109.35 (11)
C7—C6—H62	108.45 (11)	H101—C10—H102	109.467
H61—C6—H62	109.467	C10—O11—H3	106.5 (16)
C6—C7—C8	113.42 (16)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y−1, −z+1.

(AMHXOL) 6-amino-1-hexanol top

Crystal data top

C₆H₁₅NO	D_x = 1.046 Mg m⁻³
M_r = 117.19	Melting point: not measured K
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
a = 15.4577 (12) Å	Cell parameters from 3511 reflections
b = 17.5074 (12) Å	θ = 2.6–26.6°
c = 10.9970 (7) Å	µ = 0.07 mm⁻¹
V = 2976.1 (4) Å³	T = 293 K
Z = 16	Prism, colorless
F(000) = 1056.000	0.40 × 0.40 × 0.38 mm

Data collection top

Siemens P4 diffractometer	R_int = 0.08
Graphite monochromator	θ_max = 26.6°, θ_min = 2.6°
ω/2θ scans	h = −19→19
17546 measured reflections	k = −21→21
1323 independent reflections	l = −12→13
560 reflections with I > 2.00u(I)

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.085	Method = Prince modified Chebychev polynomial, (Watkin, 1994) W = [weight] * [1-(deltaF/6*sigmaF)^2]2 80.9 127. 62.7 15.1
wR(F²) = 0.226	(Δ/σ)_max = 0.006
S = 1.07	Δρ_max = 0.39 e Å⁻³
560 reflections	Δρ_min = −0.44 e Å⁻³
56 parameters	Extinction correction: Larson 1970 Crystallographic Computing eq 22
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 242.4 (436)

Crystal data top

C₆H₁₅NO	V = 2976.1 (4) Å³
M_r = 117.19	Z = 16
Orthorhombic, Fdd2	Mo Kα radiation
a = 15.4577 (12) Å	µ = 0.07 mm⁻¹
b = 17.5074 (12) Å	T = 293 K
c = 10.9970 (7) Å	0.40 × 0.40 × 0.38 mm

Data collection top

Siemens P4 diffractometer	560 reflections with I > 2.00u(I)
17546 measured reflections	R_int = 0.08
1323 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.085	56 parameters
wR(F²) = 0.226	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.39 e Å⁻³
560 reflections	Δρ_min = −0.44 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.0717 (4)	0.1382 (3)	1.5377 (5)	0.0619
C2	0.1044 (4)	0.1835 (4)	1.4408 (7)	0.0504 (16)*
C3	0.0713 (4)	0.1545 (4)	1.3188 (6)	0.0467 (14)*
C4	0.1098 (5)	0.1966 (4)	1.2117 (7)	0.0548 (16)*
C5	0.0779 (4)	0.1677 (4)	1.0896 (6)	0.0499 (14)*
C6	0.1248 (5)	0.2006 (4)	0.9809 (6)	0.0508 (15)*
C7	0.0919 (4)	0.1721 (3)	0.8593 (6)	0.0494 (14)*
N8	0.1405 (4)	0.1976 (4)	0.7525 (6)	0.0517
H9	0.0846 (4)	0.2373 (4)	1.4524 (7)	0.0554*
H10	0.1691 (4)	0.1817 (4)	1.4419 (7)	0.0554*
H11	0.0070 (4)	0.1602 (4)	1.3167 (6)	0.0581*
H12	0.0868 (4)	0.0992 (4)	1.3120 (6)	0.0581*
H13	0.0943 (5)	0.2519 (4)	1.2189 (7)	0.0597*
H14	0.1741 (5)	0.1909 (4)	1.2141 (7)	0.0597*
H15	0.0150 (4)	0.1803 (4)	1.0830 (6)	0.0572*
H16	0.0856 (4)	0.1110 (4)	1.0880 (6)	0.0572*
H17	0.1173 (5)	0.2573 (4)	0.9827 (6)	0.0593*
H18	0.1877 (5)	0.1878 (4)	0.9874 (6)	0.0593*
H19	0.0304 (4)	0.1889 (3)	0.8499 (6)	0.0568*
H20	0.0945 (4)	0.1150 (3)	0.8606 (6)	0.0568*
H1	0.135 (5)	0.245 (6)	0.765 (8)	0.07 (2)*
H2	0.202 (8)	0.171 (5)	0.760 (11)	0.09 (3)*
H3	0.093 (7)	0.156 (6)	1.595 (13)	0.09 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.083 (3)	0.077 (3)	0.026 (2)	−0.021 (2)	−0.005 (2)	0.006 (2)
N8	0.072 (4)	0.064 (3)	0.018 (2)	0.003 (3)	0.001 (2)	−0.004 (2)

Geometric parameters (Å, º) top

O1—C2	1.421 (8)	C5—C6	1.513 (9)
O1—H3	0.78 (14)	C5—H15	1.000
C2—C3	1.523 (9)	C5—H16	1.000
C2—H9	1.000	C6—C7	1.515 (9)
C2—H10	1.000	C6—H17	1.000
C3—C4	1.512 (9)	C6—H18	1.000
C3—H11	1.000	C7—N8	1.465 (8)
C3—H12	1.000	C7—H19	1.000
C4—C5	1.517 (9)	C7—H20	1.000
C4—H13	1.000	N8—H1	0.84 (9)
C4—H14	1.000	N8—H2	1.07 (12)

C2—O1—H3	103 (8)	C4—C5—H15	107.9 (3)
O1—C2—C3	110.8 (5)	C6—C5—H15	109.0 (3)
O1—C2—H9	108.7 (3)	C4—C5—H16	107.9 (3)
C3—C2—H9	108.9 (3)	C6—C5—H16	107.8 (3)
O1—C2—H10	109.2 (4)	H15—C5—H16	109.466
C3—C2—H10	109.6 (3)	C5—C6—C7	114.3 (5)
H9—C2—H10	109.468	C5—C6—H17	107.8 (3)
C2—C3—C4	113.1 (5)	C7—C6—H17	107.8 (4)
C2—C3—H11	108.8 (3)	C5—C6—H18	109.0 (3)
C4—C3—H11	108.9 (4)	C7—C6—H18	108.5 (3)
C2—C3—H12	108.0 (3)	H17—C6—H18	109.466
C4—C3—H12	108.6 (3)	C6—C7—N8	115.7 (5)
H11—C3—H12	109.466	C6—C7—H19	108.3 (3)
C3—C4—C5	113.5 (5)	N8—C7—H19	108.4 (4)
C3—C4—H13	108.5 (3)	C6—C7—H20	107.6 (3)
C5—C4—H13	108.3 (3)	N8—C7—H20	107.2 (3)
C3—C4—H14	108.8 (4)	H19—C7—H20	109.466
C5—C4—H14	108.2 (3)	C7—N8—H1	97 (6)
H13—C4—H14	109.468	C7—N8—H2	105 (6)
C4—C5—C6	114.7 (5)	H1—N8—H2	120 (8)

Experimental details

	(PZ)	(MORFCL)	(MORPHI)	(PDA8DO)
Crystal data
Chemical formula	C₄H₁₀N₂	C₄H₁₀ClNO	C₄H₁₀INO	C₆H₈N₂·C₈H₁₈O₂
M_r	86.14	123.58	215.03	254.37
Crystal system, space group	Monoclinic, P2₁/n	Monoclinic, P2₁/c	Monoclinic, P2₁/c	Monoclinic, C2/c
Temperature (K)	293	213	294	293
a, b, c (Å)	6.0817 (12), 5.2501 (4), 8.4646 (14)	5.7360 (16), 10.618 (3), 10.142 (3)	6.6521 (3), 10.4682 (8), 10.2590 (4)	36.190 (6), 5.1258 (8), 8.2222 (13)
α, β, γ (°)	90, 108.207 (14), 90	90, 101.197 (5), 90	90, 98.703 (4), 90	90, 101.773 (5), 90
V (Å³)	256.74 (7)	605.9 (3)	706.17 (7)	1493.2 (4)
Z	2	4	4	4
Radiation type	Cu Kα	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.55	0.52	4.44	0.08
Crystal size (mm)	0.60 × 0.35 × 0.25	0.12 × 0.10 × 0.08	0.66 × 0.26 × 0.08	0.75 × 0.30 × 0.25

Data collection
Diffractometer	CAD4 diffractometer	Bruker SMART CCD diffractometer	Enraf-Nonius CAD-4 diffractometer	Bruker CCD diffractometer
Absorption correction	For a cylinder mounted on the ϕ axis psi scans	–	ψ scan Azimutal absorption correction (North et al, 1968)	–
T_min, T_max	0.77, 0.87	–	0.39, 0.70	–
No. of measured, independent and observed reflections	535, 453, 424 [I > 2.00u(I)]	4061, 1463, 1152 [I > 3.00u(I)]	1600, 1519, 1323 [I > 2.00u(I)]	5234, 1776, 1087 [I > 3.00u(I)]
R_int	0.02	0.06	0.01	0.02
(sin θ/λ)_max (Å⁻¹)	0.631	0.667	0.623	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.111, 1.04	0.036, 0.083, 0.96	0.018, 0.019, 1.11	0.038, 0.094, 1.03
No. of reflections	424	1152	1323	1087
No. of parameters	33	70	73	95
No. of restraints	?	?	?	?
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.10	0.48, −0.25	0.70, −0.49	0.24, −0.27

	(PDA10D)	(PDA12D)	(AMHXOL)
Crystal data
Chemical formula	C₆H₈N₂·C₁₀H₂₂O₂	C₆H₈N₂·C₁₂H₂₆O₂	C₆H₁₅NO
M_r	282.43	310.48	117.19
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, P2₁/c	Orthorhombic, Fdd2
Temperature (K)	293	293	293
a, b, c (Å)	19.453 (2), 5.1589 (6), 8.180 (1)	22.2081 (14), 5.1843 (9), 8.217 (4)	15.4577 (12), 17.5074 (12), 10.9970 (7)
α, β, γ (°)	90, 98.398 (3), 90	90, 96.818 (3), 90	90, 90, 90
V (Å³)	812.08 (17)	939.4 (5)	2976.1 (4)
Z	2	2	16
Radiation type	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.08	0.07	0.07
Crystal size (mm)	0.35 × 0.30 × 0.05	0.26 × 0.18 × 0.08	0.40 × 0.40 × 0.38

Data collection
Diffractometer	Bruker CCD diffractometer	Bruker CCD diffractometer	Siemens P4 diffractometer
Absorption correction	–	–	–
T_min, T_max	–	–	–
No. of measured, independent and observed reflections	5982, 2017, 1051 [I > 3.00u(I)]	6256, 2260, 1143 [I > 3.00u(I)]	17546, 1323, 560 [I > 2.00u(I)]
R_int	0.03	0.08	0.08
(sin θ/λ)_max (Å⁻¹)	0.668	0.666	0.630

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.090, 0.94	0.037, 0.090, 0.96	0.085, 0.226, 1.07
No. of reflections	1051	1143	560
No. of parameters	103	113	56
No. of restraints	?	?	?
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.28	0.21, −0.20	0.39, −0.44

Computer programs: , Bruker SMART CCD, EXPRESS (Enraf-Nonius, 1993), Siemens XSCANS, SAINT, XSCANS, Xtal3.7, Siemens SHELXTL, model ring fit on i, H-bond chain along 21 axis, SIR92 (Altomare et al., 1994), SHELXS 86 (Sheldrick, 1986), Xtal CRYLSQ, CRYSTALS (Watkin et al. 2001), Xtal ORTEP, CAMERON (Watkin et al. 1996), Xtal BONDLA CIFIO.

Selected geometric parameters (Å, º) for (PZ) top

N1—C2	1.450 (2)	C2—C3	1.512 (2)
N1—C3ⁱ	1.4634 (18)

C2—N1—C3ⁱ	110.0 (1)	N1ⁱ—C3—C2	108.61 (12)
N1—C2—C3	109.05 (13)

Symmetry code: (i) −x+1, −y, −z+1.

Selected geometric parameters (Å, º) for (MORFCL) top

O1—C2	1.430 (2)	N4—C5	1.492 (2)
O1—C6	1.418 (2)	N4—H1	0.87 (3)
C2—C3	1.505 (3)	N4—H2	0.90 (3)
C3—N4	1.485 (2)	C5—C6	1.506 (2)

C2—O1—C6	109.71 (13)	C3—N4—H2	109.9 (16)
O1—C2—C3	110.82 (15)	C5—N4—H2	110.4 (15)
C2—C3—N4	110.15 (14)	H1—N4—H2	103 (2)
C3—N4—C5	110.93 (12)	N4—C5—C6	109.95 (14)
C3—N4—H1	113.5 (17)	O1—C6—C5	111.02 (15)
C5—N4—H1	109.0 (17)

Selected geometric parameters (Å, º) for (MORPHI) top

N1—C2	1.481 (3)	C3—O4	1.426 (3)
N1—C6	1.493 (3)	O4—C5	1.416 (3)
C2—C3	1.510 (4)	C5—C6	1.505 (4)

C2—N1—C6	111.8 (2)	C3—O4—C5	109.7 (2)
N1—C2—C3	109.8 (2)	O4—C5—C6	111.5 (2)
C2—C3—O4	110.8 (2)	N1—C6—C5	109.4 (2)

Selected geometric parameters (Å, º) for (PDA8DO) top

N1—C2	1.4222 (17)	C6—C7	1.506 (2)
C2—C3	1.3814 (18)	C7—C8	1.520 (2)
C2—C4ⁱ	1.386 (2)	C8—C9	1.514 (2)
C3—C4	1.3825 (19)	C9—C9ⁱⁱ	1.523 (3)
O5—C6	1.4167 (17)

N1—C2—C3	120.33 (13)	O5—C6—C7	109.32 (13)
N1—C2—C4ⁱ	120.77 (13)	C6—C7—C8	112.72 (14)
C3—C2—C4ⁱ	118.84 (12)	C7—C8—C9	113.07 (13)
C2—C3—C4	120.35 (12)	C8—C9—C9ⁱⁱ	113.28 (18)
C2ⁱ—C4—C3	120.81 (13)

Symmetry codes: (i) −x+1/2, −y+1/2, −z+2; (ii) −x+1, −y, −z+2.

Selected geometric parameters (Å, º) for (PDA10D) top

C1—C2	1.385 (2)	C5—C6	1.526 (2)
C1—C3ⁱ	1.389 (2)	C6—C7	1.526 (2)
C2—C3	1.387 (2)	C7—C8	1.528 (2)
C3—N4	1.4330 (19)	C8—C9	1.516 (2)
C5—C5ⁱⁱ	1.525 (3)	C9—O10	1.4189 (18)

C2—C1—C3ⁱ	120.18 (14)	C5ⁱⁱ—C5—C6	113.39 (17)
C1—C2—C3	120.82 (14)	C5—C6—C7	113.32 (13)
C1ⁱ—C3—C2	119.00 (13)	C6—C7—C8	113.01 (13)
C1ⁱ—C3—N4	119.88 (14)	C7—C8—C9	112.35 (13)
C2—C3—N4	121.07 (14)	C8—C9—O10	108.78 (13)

Symmetry codes: (i) −x+1, −y, −z; (ii) −x, −y−1, −z.

Selected geometric parameters (Å, º) for (PDA12D) top

C1—C2	1.383 (2)	C5—C6	1.520 (2)
C1—C3ⁱ	1.387 (2)	C6—C7	1.523 (2)
C2—C3	1.384 (2)	C7—C8	1.527 (2)
C3—N4	1.429 (2)	C8—C9	1.524 (2)
N4—H1	0.86 (3)	C9—C10	1.507 (2)
N4—H2	0.86 (3)	C10—O11	1.418 (2)
C5—C5ⁱⁱ	1.525 (3)	O11—H3	0.83 (3)

C2—C1—C3ⁱ	120.48 (15)	C5ⁱⁱ—C5—C6	113.6 (2)
C1—C2—C3	120.87 (15)	C5—C6—C7	113.48 (16)
C1ⁱ—C3—C2	118.65 (14)	C6—C7—C8	113.42 (16)
C1ⁱ—C3—N4	120.09 (15)	C7—C8—C9	112.84 (16)
C2—C3—N4	121.21 (15)	C8—C9—C10	112.59 (16)
C3—N4—H1	113.2 (14)	C9—C10—O11	109.32 (16)
C3—N4—H2	110.1 (16)	C10—O11—H3	106.5 (16)
H1—N4—H2	111 (2)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y−1, −z+1.

Selected geometric parameters (Å, º) for (AMHXOL) top

O1—C2	1.421 (8)	C5—C6	1.513 (9)
C2—C3	1.523 (9)	C6—C7	1.515 (9)
C3—C4	1.512 (9)	C7—N8	1.465 (8)
C4—C5	1.517 (9)

O1—C2—C3	110.8 (5)	C4—C5—C6	114.7 (5)
C2—C3—C4	113.1 (5)	C5—C6—C7	114.3 (5)
C3—C4—C5	113.5 (5)	C6—C7—N8	115.7 (5)

Format		BIBTeX
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Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text