N-n-Alkyl N,N-dimethylammonioacetic acid bromides: the first complete series of crystal and molecular structure determinations of an ­amphiphilic compound with alkyl chain lengths n = 1,..., 16

The molecular and crystal structures of 16 N-n-alkyl N,N-dimethylammonioacetic acid bromides with chain lengths between n = 1 and n = 16 have been determined. All compounds from n = 5 to n = 16 form bilayers with interdigitated chains. The even-numbered chains display the chain packing type M₂^II. The chain packing of the odd-numbered chain compounds is less regular. The head groups of all compounds are connected via electrostatic N⁺...Br⁻ interactions, and by OH...Br⁻ hydrogen bonds. The compounds with short chains are packed in different ways. Their molecular conformation depends on the crystal packing.

Computing details

Data collection: CAD4 Operations Manual (Enraf-Nonius, 1977) for beh1, beh5, beh6, beh7; CAD4 Operations (Enraf-Nonius) for beh3; Enraf-Nonius (1977). CAD4 Operations Manual. Enraf-Nonius, Delft, The Netherlands. for beh14, beh16. Cell refinement: CAD4 Operations Manual (Enraf-Nonius, 1977) for beh1, beh3, beh5, beh6, beh7; Enraf-Nonius (1977). CAD4 Operations Manual. Enraf-Nonius, Delft, The Netherlands. for beh14, beh16. Data reduction: MolEN (Fair, 1990) for beh1, beh6, beh7; MolEN (Fair, 1990). for beh3, beh5; Fair, C. K.: MolEN, An interactive intelligent system for crystal structure

analysis. Enraf-Nonius, Delft, The Netherlands, 1990 for beh14, beh16. Program(s) used to solve structure: MolEN (Fair, 1990) for beh1, beh7; SHELXS86 (Sheldrick, 1990) for beh3, beh5, beh6, beh16; Fair, C. K.: MolEN, An interactive intelligent system for crystal structure

analysis. Enraf-Nonius, Delft, The Netherlands, 1990 for beh14. Program(s) used to refine structure: MolEN (Fair, 1990) for beh1, beh7; SHELXL93 (Sheldrick, 1993) for beh3, beh5, beh6, beh16; Fair, C. K.: MolEN, An interactive intelligent system for crystal structure

analysis. Enraf-Nonius, Delft, The Netherlands, 1990 for beh14.

(beh1) N,N-Trimethyl Ammonio Acetic Acid Bromide

Crystal data

C5H12NO2^+·Br^−	F(000) = 400
Mr = 198.07	Dx = 1.594 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 7.613 (1) Å	θ = 8.1–15.8°
b = 9.236 (3) Å	µ = 4.92 mm^−1
c = 11.853 (4) Å	T = 298 K
β = 98.08 (2)°	Equant, colourless
V = 825.1 (4) Å^3	0.45 × 0.23 × 0.15 mm
Z = 4

Data collection

CAD4 diffractometer	1219 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
Graphite monochromator	θmax = 25.0°, θmin = 2.7°
θ/2θ scans	h = 0→9
Absorption correction: part of the refinement model (ΔF) absorption correction using the method of N. Walker and D. Stuart (1983). Acta Cryst A39, 158-166	k = 0→10
Tmin = 0.295, Tmax = 1.000	l = −14→13
1551 measured reflections	2 standard reflections every 30 min
1435 independent reflections	intensity decay: 2.2%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.083	All H-atom parameters refined
S = 0.80	Calculated w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
1435 reflections	(Δ/σ)max = −0.075
125 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.41 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
Br	0.20799 (3)	0.75849 (3)	0.08667 (2)	0.0424 (2)
O1	0.5805 (3)	0.7882 (2)	0.8945 (2)	0.0523 (6)
O2	0.3867 (3)	0.6070 (2)	0.8945 (2)	0.0513 (6)
H2	0.344 (5)	0.657 (4)	0.939 (3)	0.061 (10)*
C31	0.5226 (3)	0.6730 (3)	0.8602 (2)	0.0369 (6)
C32	0.5906 (3)	0.5805 (3)	0.7710 (2)	0.0352 (6)
H32A	0.619 (4)	0.493 (3)	0.803 (2)	0.043 (8)*
H32B	0.504 (4)	0.572 (4)	0.709 (2)	0.047 (8)*
N1	0.7572 (3)	0.6311 (2)	0.7295 (2)	0.0335 (5)
C33	0.7953 (5)	0.5242 (4)	0.6403 (3)	0.0520 (8)
H33A	0.900 (4)	0.555 (4)	0.615 (3)	0.058 (9)*
H33B	0.691 (4)	0.530 (4)	0.581 (2)	0.053 (9)*
H33C	0.797 (4)	0.442 (5)	0.673 (3)	0.065 (12)*
C34	0.7349 (5)	0.7776 (4)	0.6755 (3)	0.0427 (7)*
H34A	0.844 (4)	0.795 (3)	0.645 (2)	0.030 (7)*
H34B	0.729 (3)	0.838 (3)	0.729 (3)	0.030 (7)*
H34C	0.637 (5)	0.775 (3)	0.628 (3)	0.058 (10)*
C1	0.9098 (4)	0.6328 (4)	0.8239 (3)	0.0478 (8)
H1A	1.007 (5)	0.660 (4)	0.794 (3)	0.055 (9)*
H1B	0.925 (5)	0.550 (5)	0.863 (3)	0.075 (12)*
H1C	0.885 (4)	0.696 (4)	0.881 (3)	0.057 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br	0.0416 (3)	0.0438 (3)	0.0422 (3)	0.00378 (11)	0.0070 (2)	0.00334 (11)
O1	0.0631 (14)	0.0412 (12)	0.0543 (13)	−0.0073 (11)	0.0142 (11)	−0.0149 (11)
O2	0.0558 (12)	0.0480 (13)	0.0540 (13)	−0.0083 (10)	0.0210 (11)	−0.0084 (10)
C31	0.0413 (14)	0.0324 (15)	0.0357 (14)	0.0030 (12)	0.0007 (11)	0.0021 (12)
C32	0.0361 (14)	0.0279 (14)	0.0402 (15)	−0.0027 (11)	0.0004 (12)	−0.0004 (12)
N1	0.0349 (11)	0.0276 (12)	0.0366 (11)	−0.0008 (9)	−0.0001 (9)	−0.0016 (9)
C33	0.057 (2)	0.043 (2)	0.060 (2)	−0.0078 (15)	0.021 (2)	−0.015 (2)
C1	0.037 (2)	0.053 (2)	0.049 (2)	−0.0033 (14)	−0.0051 (14)	0.004 (2)

Geometric parameters (Å, º)

O1—C31	1.200 (4)	C33—H33A	0.93 (3)
O2—C31	1.314 (3)	C33—H33B	0.99 (3)
O2—H2	0.80 (4)	C33—H33C	0.85 (4)
C31—C32	1.507 (4)	C34—H34A	0.97 (3)
C32—N1	1.498 (3)	C34—H34B	0.85 (3)
C32—H32A	0.90 (3)	C34—H34C	0.87 (4)
C32—H32B	0.92 (3)	C1—H1A	0.90 (3)
N1—C1	1.496 (4)	C1—H1B	0.89 (4)
N1—C34	1.496 (4)	C1—H1C	0.93 (4)
N1—C33	1.504 (4)
C31—O2—H2	110 (3)	N1—C33—H33B	104.3 (18)
O1—C31—O2	125.0 (3)	H33A—C33—H33B	113 (3)
O1—C31—C32	126.5 (2)	N1—C33—H33C	105 (2)
O2—C31—C32	108.5 (2)	H33A—C33—H33C	117 (3)
N1—C32—C31	116.4 (2)	H33B—C33—H33C	109 (3)
N1—C32—H32A	104.5 (17)	N1—C34—H34A	105.0 (17)
C31—C32—H32A	107.4 (17)	N1—C34—H34B	106.9 (18)
N1—C32—H32B	108.3 (17)	H34A—C34—H34B	108 (3)
C31—C32—H32B	108.9 (18)	N1—C34—H34C	107 (2)
H32A—C32—H32B	111 (3)	H34A—C34—H34C	118 (3)
C1—N1—C32	111.2 (2)	H34B—C34—H34C	112 (3)
C1—N1—C34	109.9 (2)	N1—C1—H1A	108 (2)
C32—N1—C34	111.8 (2)	N1—C1—H1B	114 (2)
C1—N1—C33	109.0 (3)	H1A—C1—H1B	113 (3)
C32—N1—C33	106.4 (2)	N1—C1—H1C	110 (2)
C34—N1—C33	108.4 (2)	H1A—C1—H1C	112 (3)
N1—C33—H33A	107 (2)	H1B—C1—H1C	100 (3)
O1—C31—C32—N1	6.2 (4)	C31—C32—N1—C34	−60.7 (3)
O2—C31—C32—N1	−174.2 (2)	C31—C32—N1—C33	−178.8 (3)
C31—C32—N1—C1	62.6 (3)

(beh3) N-n-Propyl N,N-Dimethyl Ammonio Acetic Acid Bromide

Crystal data

C7H16NO2^+·Br^−	F(000) = 464
Mr = 226.12	Dx = 1.433 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 6.793 (3) Å	θ = 10–15°
b = 13.85 (1) Å	µ = 3.88 mm^−1
c = 11.420 (5) Å	T = 223 K
β = 102.71 (4)°	Equant, colourless
V = 1048.1 (10) Å^3	0.38 × 0.22 × 0.20 mm
Z = 4

Data collection

CAD4 diffractometer	1090 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.043
Graphite monochromator	θmax = 22.0°, θmin = 2.4°
θ/2θ scans	h = 0→7
Absorption correction: part of the refinement model (ΔF) absorption correction using the method of N. Walker and D. Stuart (1983). Acta Cryst A39, 158-166	k = −1→14
Tmin = 0.285, Tmax = 1.000	l = −12→11
1533 measured reflections	2 standard reflections every 30 min
1288 independent reflections	intensity decay: 3%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	All H-atom parameters refined
S = 0.88	Calculated w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
1288 reflections	(Δ/σ)max = 0.006
165 parameters	Δρmax = 0.66 e Å^−3
0 restraints	Δρmin = −0.42 e Å^−3

Special details

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

Refinement. Refinement on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating R_factor_gt etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Br	0.24162 (7)	0.22588 (4)	0.63472 (5)	0.0455 (3)
O1	0.2053 (5)	−0.0585 (2)	0.3364 (4)	0.0526 (10)
O2	−0.1040 (5)	−0.0108 (3)	0.3493 (3)	0.0466 (10)
H2	−0.129 (7)	−0.067 (4)	0.349 (4)	0.024 (13)*
N1	0.3145 (5)	0.1403 (3)	0.3030 (3)	0.0317 (9)
C31	0.0824 (7)	0.0030 (4)	0.3388 (4)	0.0347 (11)
C32	0.1177 (7)	0.1100 (4)	0.3309 (5)	0.0341 (11)
H32A	0.116 (6)	0.134 (3)	0.400 (4)	0.025 (13)*
H32B	0.011 (7)	0.137 (4)	0.267 (5)	0.050 (15)*
C33	0.3116 (10)	0.2481 (4)	0.2977 (6)	0.0449 (13)
H33A	0.431 (8)	0.269 (3)	0.270 (4)	0.040 (14)*
H33B	0.295 (7)	0.268 (4)	0.381 (5)	0.039 (14)*
H33C	0.189 (8)	0.273 (3)	0.250 (4)	0.027 (12)*
C34	0.4905 (8)	0.1106 (5)	0.4011 (5)	0.0410 (12)
H34A	0.500 (7)	0.045 (4)	0.405 (4)	0.043 (15)*
H34B	0.460 (7)	0.134 (3)	0.476 (4)	0.033 (12)*
H34C	0.611 (8)	0.143 (4)	0.383 (4)	0.041 (13)*
C1	0.3490 (8)	0.0987 (4)	0.1857 (4)	0.0411 (12)
H1A	0.492 (8)	0.113 (4)	0.177 (4)	0.055 (15)*
H1B	0.360 (6)	0.030 (3)	0.198 (4)	0.021 (11)*
C2	0.1964 (12)	0.1247 (6)	0.0759 (6)	0.074 (2)
H2A	0.206 (12)	0.219 (6)	0.077 (8)	0.12 (3)*
H2B	0.066 (10)	0.106 (5)	0.082 (6)	0.08 (2)*
C3	0.2509 (16)	0.0806 (8)	−0.0342 (7)	0.088 (3)
H3A	0.159 (10)	0.099 (5)	−0.114 (7)	0.08 (2)*
H3B	0.254 (9)	0.014 (5)	−0.026 (6)	0.07 (2)*
H3C	0.375 (12)	0.108 (7)	−0.047 (8)	0.13 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br	0.0442 (4)	0.0473 (4)	0.0464 (4)	−0.0143 (2)	0.0130 (3)	−0.0139 (2)
O1	0.045 (2)	0.031 (2)	0.083 (3)	0.007 (2)	0.015 (2)	0.002 (2)
O2	0.038 (2)	0.036 (2)	0.066 (3)	−0.007 (2)	0.014 (2)	−0.001 (2)
N1	0.033 (2)	0.028 (2)	0.032 (2)	0.001 (2)	0.002 (2)	0.001 (2)
C31	0.040 (3)	0.037 (3)	0.024 (3)	−0.003 (2)	0.000 (2)	−0.004 (2)
C32	0.037 (3)	0.036 (3)	0.028 (3)	0.003 (2)	0.004 (2)	0.002 (2)
C33	0.048 (4)	0.038 (3)	0.049 (4)	−0.003 (3)	0.012 (3)	0.003 (3)
C34	0.027 (3)	0.049 (4)	0.040 (3)	0.006 (3)	−0.006 (2)	0.002 (3)
C1	0.048 (3)	0.041 (3)	0.034 (3)	0.012 (2)	0.009 (2)	0.002 (2)
C2	0.070 (5)	0.109 (6)	0.037 (4)	0.033 (4)	−0.002 (3)	−0.007 (4)
C3	0.116 (7)	0.107 (8)	0.037 (4)	0.038 (6)	0.008 (4)	−0.004 (4)

Geometric parameters (Å, º)

O1—C31	1.197 (6)	C34—H34A	0.91 (5)
O2—C31	1.311 (6)	C34—H34B	0.98 (5)
O2—H2	0.80 (5)	C34—H34C	0.99 (5)
N1—C33	1.494 (7)	C1—C2	1.485 (9)
N1—C32	1.501 (6)	C1—H1A	1.02 (5)
N1—C34	1.505 (6)	C1—H1B	0.97 (4)
N1—C1	1.523 (6)	C2—C3	1.515 (10)
C31—C32	1.508 (7)	C2—H2A	1.31 (8)
C32—H32A	0.86 (5)	C2—H2B	0.94 (6)
C32—H32B	0.98 (5)	C3—H3A	1.02 (7)
C33—H33A	0.98 (5)	C3—H3B	0.93 (7)
C33—H33B	1.02 (5)	C3—H3C	0.96 (8)
C33—H33C	0.95 (5)
C31—O2—H2	111 (3)	N1—C34—H34B	106 (3)
C33—N1—C32	106.5 (4)	H34A—C34—H34B	109 (4)
C33—N1—C34	107.8 (4)	N1—C34—H34C	106 (3)
C32—N1—C34	111.4 (4)	H34A—C34—H34C	114 (4)
C33—N1—C1	110.2 (4)	H34B—C34—H34C	112 (4)
C32—N1—C1	113.4 (4)	C2—C1—N1	116.0 (4)
C34—N1—C1	107.5 (4)	C2—C1—H1A	112 (3)
O1—C31—O2	126.3 (4)	N1—C1—H1A	111 (3)
O1—C31—C32	125.2 (4)	C2—C1—H1B	112 (3)
O2—C31—C32	108.5 (4)	N1—C1—H1B	106 (2)
N1—C32—C31	116.6 (4)	H1A—C1—H1B	99 (4)
N1—C32—H32A	106 (3)	C1—C2—C3	110.5 (6)
C31—C32—H32A	107 (3)	C1—C2—H2A	102 (4)
N1—C32—H32B	106 (3)	C3—C2—H2A	113 (4)
C31—C32—H32B	109 (3)	C1—C2—H2B	112 (4)
H32A—C32—H32B	112 (4)	C3—C2—H2B	111 (4)
N1—C33—H33A	108 (3)	H2A—C2—H2B	109 (6)
N1—C33—H33B	104 (3)	C2—C3—H3A	115 (4)
H33A—C33—H33B	120 (4)	C2—C3—H3B	108 (4)
N1—C33—H33C	113 (3)	H3A—C3—H3B	110 (6)
H33A—C33—H33C	113 (4)	C2—C3—H3C	111 (6)
H33B—C33—H33C	100 (4)	H3A—C3—H3C	99 (7)
N1—C34—H34A	110 (3)	H3B—C3—H3C	114 (7)
C33—N1—C32—C31	178.9 (4)	C33—N1—C1—C2	−59.5 (7)
C34—N1—C32—C31	−63.8 (5)	C32—N1—C1—C2	59.7 (7)
C1—N1—C32—C31	57.6 (5)	C34—N1—C1—C2	−176.7 (6)
O1—C31—C32—N1	7.7 (7)	N1—C1—C2—C3	178.8 (7)
O2—C31—C32—N1	−172.6 (4)

(beh5) N-n-Pentyl N,N-Dimethyl Ammonio Acetic Acid Bromide

Crystal data

C9H20NO2^+·Br^−	Z = 2
Mr = 254.17	F(000) = 264
Triclinic, P1	Dx = 1.358 Mg m^−3
a = 6.771 (3) Å	Mo Kα radiation, λ = 0.71069 Å
b = 7.599 (2) Å	Cell parameters from 24 reflections
c = 12.273 (5) Å	θ = 11–17°
α = 94.17 (3)°	µ = 3.28 mm^−1
β = 92.04 (3)°	T = 298 K
γ = 98.83 (3)°	Plate, colourless
V = 621.6 (4) Å^3	0.66 × 0.14 × 0.06 mm

Data collection

CAD4 diffractometer	331 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.050
Graphite monochromator	θmax = 20.0°, θmin = 1.7°
θ/2θ scans	h = 0→2
Absorption correction: part of the refinement model (ΔF) absorption correction using the method of N. Walker and D. Stuart (1983). Acta Cryst A39, 158-166	k = −7→7
Tmin = 0.056, Tmax = 1.000	l = −11→11
672 measured reflections	3 standard reflections every 30 min
536 independent reflections	intensity decay: 70%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.095	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.224	Position relative to binding partner calculated and kept fixed during refinement, isotropic displacement parameter constrained to binding partner
S = 1.53	Calculated w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
536 reflections	(Δ/σ)max = 0.022
73 parameters	Δρmax = 0.54 e Å^−3
9 restraints	Δρmin = −0.43 e Å^−3

Special details

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

Refinement. Refinement on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Br	−0.2330 (9)	−0.2951 (4)	−0.1755 (3)	0.102 (5)
O1	0.470 (5)	0.101 (3)	−0.230 (2)	0.107 (19)
O2	0.389 (5)	−0.121 (2)	−0.1181 (16)	0.106 (17)
C31	0.356 (11)	0.029 (5)	−0.162 (4)	0.122 (15)*
C32	0.172 (7)	0.077 (3)	−0.116 (3)	0.085 (10)*
H32A	0.199 (7)	0.111 (3)	−0.038 (3)	0.128*
H32B	0.071 (7)	−0.029 (3)	−0.122 (3)	0.128*
C33	−0.085 (8)	0.263 (4)	−0.100 (3)	0.103 (13)*
H33A	−0.034 (8)	0.302 (4)	−0.027 (3)	0.154*
H33B	−0.178 (8)	0.154 (4)	−0.100 (3)	0.154*
H33C	−0.150 (8)	0.353 (4)	−0.130 (3)	0.154*
C34	0.250 (8)	0.401 (4)	−0.152 (3)	0.122 (12)*
H34A	0.360 (8)	0.383 (4)	−0.197 (3)	0.183*
H34B	0.297 (8)	0.420 (4)	−0.077 (3)	0.183*
H34C	0.196 (8)	0.504 (4)	−0.173 (3)	0.183*
N1	0.082 (7)	0.230 (3)	−0.168 (2)	0.08 (2)
C1	0.032 (7)	0.168 (4)	−0.287 (3)	0.122 (12)*
H1A	0.156 (7)	0.164 (4)	−0.324 (3)	0.183*
H1B	−0.041 (7)	0.048 (4)	−0.292 (3)	0.183*
C2	−0.087 (7)	0.281 (4)	−0.347 (3)	0.162 (16)*
H2A	−0.213 (7)	0.285 (4)	−0.312 (3)	0.243*
H2B	−0.014 (7)	0.402 (4)	−0.344 (3)	0.243*
C3	−0.126 (6)	0.209 (4)	−0.462 (3)	0.151 (15)*
H3A	0.001 (6)	0.196 (4)	−0.494 (3)	0.226*
H3B	−0.205 (6)	0.091 (4)	−0.464 (3)	0.226*
C4	−0.230 (8)	0.323 (6)	−0.527 (3)	0.21 (2)*
H4A	−0.214 (8)	0.442 (6)	−0.489 (3)	0.319*
H4B	−0.167 (8)	0.335 (6)	−0.596 (3)	0.319*
C5	−0.441 (8)	0.258 (7)	−0.547 (5)	0.31 (4)*
H5A	−0.500 (8)	0.340 (7)	−0.589 (5)	0.468*
H5B	−0.505 (8)	0.248 (7)	−0.479 (5)	0.468*
H5C	−0.458 (8)	0.143 (7)	−0.587 (5)	0.468*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br	0.094 (13)	0.092 (2)	0.119 (3)	0.011 (3)	−0.012 (4)	0.011 (2)
O1	0.06 (6)	0.133 (15)	0.14 (2)	0.04 (2)	0.04 (3)	0.026 (16)
O2	0.11 (6)	0.102 (11)	0.119 (18)	0.043 (19)	0.02 (2)	0.027 (12)
N1	0.07 (7)	0.083 (13)	0.08 (2)	−0.01 (2)	0.01 (3)	−0.004 (13)

Geometric parameters (Å, º)

O1—C31	1.25 (6)	C1—C2	1.48 (3)
O2—C31	1.34 (4)	C1—H1A	0.97
C31—C32	1.47 (7)	C1—H1B	0.97
C32—N1	1.56 (4)	C2—C3	1.47 (3)
C32—H32A	0.97	C2—H2A	0.97
C32—H32B	0.97	C2—H2B	0.97
C33—N1	1.46 (5)	C3—C4	1.46 (3)
C33—H33A	0.96	C3—H3A	0.97
C33—H33B	0.96	C3—H3B	0.97
C33—H33C	0.96	C4—C5	1.44 (3)
C34—N1	1.59 (5)	C4—H4A	0.97
C34—H34A	0.96	C4—H4B	0.97
C34—H34B	0.96	C5—H5A	0.96
C34—H34C	0.96	C5—H5B	0.96
N1—C1	1.52 (4)	C5—H5C	0.96
O1—C31—O2	121 (6)	N1—C1—H1A	109 (2)
O1—C31—C32	132 (4)	C2—C1—H1B	109 (2)
O2—C31—C32	107 (5)	N1—C1—H1B	108.5 (16)
C31—C32—N1	117 (3)	H1A—C1—H1B	107.5
C31—C32—H32A	108 (3)	C3—C2—C1	110 (3)
N1—C32—H32A	108.1 (16)	C3—C2—H2A	110 (3)
C31—C32—H32B	108 (2)	C1—C2—H2A	110 (3)
N1—C32—H32B	108 (2)	C3—C2—H2B	110 (2)
H32A—C32—H32B	107.3	C1—C2—H2B	110 (2)
N1—C33—H33A	110 (2)	H2A—C2—H2B	108.1
N1—C33—H33B	109.5 (18)	C4—C3—C2	113 (3)
H33A—C33—H33B	109.5	C4—C3—H3A	109 (2)
N1—C33—H33C	109.5 (15)	C2—C3—H3A	109 (3)
H33A—C33—H33C	109.5	C4—C3—H3B	109 (2)
H33B—C33—H33C	109.5	C2—C3—H3B	109 (2)
N1—C34—H34A	110 (2)	H3A—C3—H3B	107.8
N1—C34—H34B	109.5 (15)	C5—C4—C3	114 (3)
H34A—C34—H34B	109.5	C5—C4—H4A	109 (3)
N1—C34—H34C	109.5 (19)	C3—C4—H4A	108.8 (19)
H34A—C34—H34C	109.5	C5—C4—H4B	109 (3)
H34B—C34—H34C	109.5	C3—C4—H4B	109 (2)
C33—N1—C1	117 (4)	H4A—C4—H4B	107.6
C33—N1—C32	105 (3)	C4—C5—H5A	110 (3)
C1—N1—C32	107 (2)	C4—C5—H5B	109 (3)
C33—N1—C34	108 (3)	H5A—C5—H5B	109.5
C1—N1—C34	112 (3)	C4—C5—H5C	110 (3)
C32—N1—C34	106 (3)	H5A—C5—H5C	109.5
C2—C1—N1	115 (3)	H5B—C5—H5C	109.47 (7)
C2—C1—H1A	109 (3)
O1—C31—C32—N1	8 (8)	C32—N1—C1—C2	170 (4)
O2—C31—C32—N1	−170 (3)	C34—N1—C1—C2	−74 (5)
C31—C32—N1—C33	−174 (4)	N1—C1—C2—C3	180 (4)
C31—C32—N1—C1	61 (5)	C1—C2—C3—C4	−176 (4)
C31—C32—N1—C34	−59 (4)	C2—C3—C4—C5	−103 (6)
C33—N1—C1—C2	52 (4)

(beh6) N-n-Hexyl N,N-Dimethyl Ammonio Acetic Acid Bromide

Crystal data

C10H22NO2^+·Br^−	Z = 2
Mr = 268.20	F(000) = 280
Triclinic, P1	Dx = 1.311 Mg m^−3
a = 6.739 (6) Å	Cu Kα radiation, λ = 1.54178 Å
b = 7.525 (2) Å	Cell parameters from 25 reflections
c = 13.67 (2) Å	θ = 15–21°
α = 85.61 (6)°	µ = 3.97 mm^−1
β = 86.18 (9)°	T = 298 K
γ = 79.81 (4)°	Plate, colourless
V = 679.3 (12) Å^3	0.40 × 0.15 × 0.07 mm

Data collection

CAD4 diffractometer	1297 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.191
Graphite monochromator	θmax = 54.2°, θmin = 3.3°
θ/2θ scans	h = 0→7
1422 measured reflections	k = −7→7
1299 independent reflections	l = −13→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.387	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.702	Position relative to binding partner calculated and kept fixed during refinement, isotropic displacement parameter constrained to binding partner
S = 7.80	Calculated w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
1299 reflections	(Δ/σ)max = −3.086
57 parameters	Δρmax = 11.81 e Å^−3
12 restraints	Δρmin = −11.98 e Å^−3

Special details

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

Refinement. Refinement on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Br	0.7138 (8)	0.2022 (7)	0.1557 (4)	0.000 (2)*
O1	1.008 (6)	0.609 (6)	0.215 (3)	0.018 (11)*
O2	1.095 (8)	0.383 (6)	0.108 (4)	0.035 (13)*
N1	1.372 (6)	0.727 (5)	0.156 (3)	0.012 (12)*
C31	1.120 (6)	0.539 (6)	0.152 (3)	0.000 (12)*
C32	1.297 (7)	0.600 (7)	0.093 (3)	0.007 (13)*
C33	1.557 (6)	0.761 (7)	0.096 (4)	0.000 (11)*
C34	1.218 (8)	0.895 (7)	0.135 (5)	0.022 (16)*
C1	1.427 (9)	0.663 (7)	0.259 (3)	0.019 (16)*
C2	1.543 (9)	0.781 (7)	0.310 (4)	0.019 (16)*
C3	1.601 (10)	0.682 (8)	0.408 (4)	0.028 (18)*
C4	1.727 (12)	0.793 (10)	0.459 (5)	0.04 (2)*
C5	1.765 (16)	0.719 (13)	0.564 (5)	0.06 (3)*
C6	1.88 (2)	0.857 (18)	0.602 (11)	0.11 (5)*

Geometric parameters (Å, º)

O1—C31	1.19 (4)	C31—C32	1.52 (2)
O2—C31	1.40 (4)	C1—C2	1.52 (2)
N1—C32	1.50 (2)	C2—C3	1.53 (2)
N1—C1	1.50 (2)	C3—C4	1.52 (2)
N1—C33	1.50 (2)	C4—C5	1.52 (2)
N1—C34	1.51 (2)	C5—C6	1.52 (2)
C32—N1—C1	119 (4)	O2—C31—C32	104 (3)
C32—N1—C33	100 (3)	N1—C32—C31	106 (3)
C1—N1—C33	109 (4)	N1—C1—C2	116 (4)
C32—N1—C34	100 (4)	C1—C2—C3	107 (4)
C1—N1—C34	121 (4)	C4—C3—C2	109 (5)
C33—N1—C34	104 (4)	C5—C4—C3	112 (6)
O1—C31—O2	124 (4)	C6—C5—C4	103 (8)
O1—C31—C32	131 (4)
C1—N1—C32—C31	55 (6)	C33—N1—C1—C2	53 (6)
C33—N1—C32—C31	174 (4)	C34—N1—C1—C2	−69 (7)
C34—N1—C32—C31	−79 (5)	N1—C1—C2—C3	−174 (5)
O1—C31—C32—N1	25 (8)	C1—C2—C3—C4	177 (6)
O2—C31—C32—N1	−162 (4)	C2—C3—C4—C5	171 (7)
C32—N1—C1—C2	167 (5)	C3—C4—C5—C6	−176 (9)

(beh7) N-n-Heptyl N,N-Dimethyl Ammonio Acetic Acid Bromide

Crystal data

C11H24NO2^+·Br^−	Z = 2
Mr = 282.23	F(000) = 296
Triclinic, P1	Dx = 1.305 Mg m^−3
a = 6.872 (2) Å	Mo Kα radiation, λ = 0.71069 Å
b = 7.519 (1) Å	Cell parameters from 25 reflections
c = 14.107 (1) Å	θ = 10–15°
α = 85.59 (1)°	µ = 2.85 mm^−1
β = 87.20 (2)°	T = 296 K
γ = 81.44 (2)°	Plate, colourless
V = 718.2 (2) Å^3	0.35 × 0.24 × 0.05 mm

Data collection

CAD4 diffractometer	θmax = 25°
Radiation source: fine-focus sealed tube	h = 0→8
Graphite monochromator	k = −8→8
θ/2θ scans	l = −16→16
1874 independent reflections	2 standard reflections
1558 reflections with I > 2σ(I)	intensity decay: 19%

Refinement

Refinement on F	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.069	Position relative to binding partner calculated and kept fixed during refinement, isotropic displacement parameter constrained to binding partner
S = 0.97	X
0 restraints

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

	x	y	z	Uiso*/Ueq
Br1	−1.7934 (1)	−0.7946 (1)	−0.84966 (6)	0.0689 (3)
O1	−1.4910 (7)	−0.3989 (7)	−0.7987 (4)	0.082 (1)
O2	−1.4111 (8)	−0.6213 (7)	−0.8969 (4)	0.079 (1)
N1	−1.1174 (8)	−0.2699 (7)	−0.8546 (4)	0.057 (1)
C1	−1.077 (1)	−0.331 (1)	−0.7488 (5)	0.067 (3)
C2	−0.953 (1)	−0.221 (1)	−0.7007 (5)	0.070 (3)
C3	−0.943 (1)	−0.287 (1)	−0.5952 (6)	0.080 (3)
C4	−0.796 (1)	−0.203 (1)	−0.5418 (7)	0.087 (3)
C5	−0.796 (1)	−0.264 (1)	−0.4355 (7)	0.098 (4)
C6	−0.644 (2)	−0.185 (2)	−0.3779 (8)	0.117 (4)
C7	−0.441 (2)	−0.273 (2)	−0.405 (1)	0.149 (5)
C31	−1.384 (1)	−0.4734 (9)	−0.8567 (6)	0.062 (3)
C32	−1.195 (1)	−0.4170 (9)	−0.8990 (5)	0.056 (1)
C33	−0.927 (1)	−0.246 (1)	−0.9076 (6)	0.068 (3)
C34	−1.257 (1)	−0.097 (1)	−0.8648 (7)	0.080 (3)
H11	−1.20 (1)	−0.33 (1)	−0.714 (6)	0.13 (4)
H12	−1.011 (9)	−0.451 (8)	−0.746 (4)	0.06 (1)
H21	−0.82 (1)	−0.232 (9)	−0.730 (5)	0.09 (3)
H22	−1.01 (1)	−0.097 (9)	−0.707 (5)	0.08 (3)
H31	−1.07 (1)	−0.26 (1)	−0.565 (6)	0.13 (4)
H32	−0.91 (1)	−0.415 (9)	−0.591 (5)	0.09 (3)
H41	−0.67 (1)	−0.24 (1)	−0.569 (5)	0.10 (3)
H42	−0.83 (1)	−0.076 (9)	−0.548 (5)	0.09 (3)
H51	−0.93 (2)	−0.23 (2)	−0.408 (9)	0.22 (5)
H52	−0.77 (1)	−0.39 (1)	−0.429 (6)	0.13 (3)
H61	−0.66 (1)	−0.06 (1)	−0.393 (7)	0.14 (4)
H62	−0.67 (1)	−0.21 (1)	−0.312 (6)	0.14 (4)
H71	−0.34 (2)	−0.23 (2)	−0.37 (1)	0.24 (6)
H72	−0.41 (3)	−0.26 (3)	−0.47 (1)	0.4 (1)
H73	−0.43 (3)	−0.41 (2)	−0.39 (1)	0.33 (9)
H321	−1.216 (9)	−0.378 (8)	−0.964 (4)	0.06 (3)
H322	−1.096 (9)	−0.520 (9)	−0.895 (5)	0.08 (3)
H331	−0.95 (1)	−0.21 (1)	−0.972 (5)	0.09 (3)
H332	−0.84 (1)	−0.357 (9)	−0.905 (5)	0.08 (3)
H333	−0.87 (1)	−0.16 (1)	−0.879 (6)	0.11 (3)
H341	−1.28 (1)	−0.06 (1)	−0.930 (5)	0.10 (3)
H342	−1.20 (2)	−0.00 (1)	−0.836 (8)	0.22 (5)
H343	−1.38 (1)	−0.11 (1)	−0.833 (7)	0.14 (4)
H2	−0.49 (1)	−0.70 (1)	−0.875 (6)	0.13 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0637 (4)	0.0577 (4)	0.0847 (5)	−0.0089 (3)	−0.0049 (4)	0.0015 (4)
O1	0.057 (3)	0.087 (3)	0.103 (4)	−0.007 (3)	0.024 (3)	−0.029 (3)
O2	0.069 (3)	0.077 (3)	0.093 (4)	−0.022 (2)	0.014 (3)	−0.019 (3)
N1	0.050 (3)	0.054 (3)	0.065 (3)	−0.001 (2)	0.011 (3)	−0.011 (3)
C1	0.072 (4)	0.064 (4)	0.062 (4)	−0.006 (4)	0.008 (4)	−0.008 (4)
C2	0.072 (4)	0.071 (4)	0.064 (4)	−0.006 (4)	0.008 (4)	−0.012 (4)
C3	0.078 (5)	0.083 (5)	0.077 (5)	−0.005 (4)	−0.001 (4)	−0.011 (4)
C4	0.088 (6)	0.083 (5)	0.090 (6)	−0.011 (5)	0.004 (5)	−0.007 (5)
C5	0.102 (6)	0.110 (7)	0.081 (6)	−0.007 (6)	−0.013 (5)	−0.021 (5)
C6	0.127 (8)	0.105 (7)	0.115 (8)	−0.002 (7)	−0.002 (7)	−0.014 (6)
C7	0.13 (1)	0.18 (1)	0.14 (1)	0.002 (9)	−0.009 (8)	−0.022 (9)
C31	0.050 (3)	0.056 (4)	0.078 (5)	−0.001 (3)	−0.002 (3)	−0.004 (4)
C32	0.049 (3)	0.051 (3)	0.067 (4)	0.002 (3)	0.003 (3)	−0.011 (3)
C34	0.084 (5)	0.049 (4)	0.098 (6)	0.015 (4)	0.003 (5)	−0.002 (4)
C33	0.058 (4)	0.077 (4)	0.074 (5)	−0.018 (3)	0.018 (4)	−0.011 (4)

Geometric parameters (Å, º)

O1—C31	1.190 (9)	C5—C6	1.57 (2)
O2—C31	1.33 (1)	C5—H51	1.0 (1)
N1—C1	1.554 (9)	C5—H52	0.95 (8)
N1—C32	1.488 (9)	C6—C7	1.49 (2)
N1—C34	1.499 (9)	C6—H61	0.95 (9)
N1—C33	1.502 (9)	C6—H62	0.95 (9)
C1—C2	1.50 (1)	C7—H71	0.9 (1)
C1—H11	0.96 (9)	C7—H72	1.0 (2)
C1—H12	0.94 (6)	C7—H73	1.0 (2)
C2—C3	1.54 (1)	C31—C32	1.51 (1)
C2—H21	0.96 (7)	C32—H321	0.95 (6)
C2—H22	0.95 (7)	C32—H322	0.95 (6)
C3—C4	1.53 (1)	C33—H331	0.94 (7)
C3—H31	0.95 (8)	C33—H332	0.95 (6)
C3—H32	0.95 (7)	C33—H333	0.95 (9)
C4—C5	1.53 (1)	C34—H341	0.94 (8)
C4—H41	0.94 (7)	C34—H342	1.0 (1)
C4—H42	0.95 (7)	C34—H343	1.0 (1)
C1—N1—C32	108.5 (5)	H51—C5—H52	108 (9)
C1—N1—C34	112.2 (6)	C5—C6—C7	109 (1)
C1—N1—C33	109.7 (5)	C5—C6—H61	108 (6)
C4—C3—H32	109 (4)	C5—C6—H62	109 (6)
H31—C3—H32	109 (7)	C7—C6—H61	111 (5)
C32—N1—C34	111.0 (5)	C7—C6—H62	111 (6)
C32—N1—C33	106.2 (5)	H61—C6—H62	110 (8)
C34—N1—C33	109.0 (5)	C6—C7—H71	111 (1)
N1—C1—C2	115.0 (6)	C6—C7—H72	113 (9)
N1—C1—H11	109 (5)	C6—C7—H73	111 (11)
N1—C1—H12	109 (4)	H71—C7—H72	109.25
C2—C1—H11	108 (6)	H71—C7—H73	107 (13)
C2—C1—H12	107 (4)	H72—C7—H73	103.25
H11—C1—H12	109 (6)	O1—C31—O2	125.8 (7)
C1—C2—C3	108.4 (7)	O1—C31—C32	126.7 (7)
C1—C2—H21	110 (5)	O2—C31—C32	107.5 (6)
C1—C2—H22	109 (4)	N1—C32—C31	117.3 (6)
C3—C2—H21	110 (4)	N1—C32—H321	107 (4)
C3—C2—H22	110 (4)	N1—C32—H322	107 (4)
H21—C2—H22	109 (6)	C31—C32—H321	108 (4)
C2—C3—C4	113.1 (7)	C31—C32—H322	108 (4)
C2—C3—H31	109 (5)	H321—C32—H322	109 (5)
C2—C3—H32	108 (4)	N1—C33—H331	110 (4)
C4—C3—H31	108 (6)	N1—C33—H332	110 (5)
C3—C4—C5	112.4 (8)	N1—C33—H333	109 (4)
C3—C4—H41	108 (5)	H331—C33—H332	109 (6)
C3—C4—H42	109 (4)	H331—C33—H333	110 (6)
C5—C4—H41	109 (4)	H332—C33—H333	109 (7)
C5—C4—H42	108 (4)	N1—C34—H341	110 (7)
H41—C4—H42	110 (6)	N1—C34—H342	109 (4)
C4—C5—C6	114.3 (9)	N1—C34—H343	110 (5)
C4—C5—H51	109 (7)	H341—C34—H342	110 (7)
C4—C5—H52	109 (5)	H341—C34—H343	110 (8)
C6—C5—H51	109 (8)	H342—C34—H343	109 (9)
C6—C5—H52	108 (5)
C32—N1—C1—C2	165.4 (6)	C1—C2—C3—C4	171.5 (7)
C34—N1—C1—C2	−71.5 (8)	C2—C3—C4—C5	177.2 (7)
C33—N1—C1—C2	49.9 (8)	C3—C4—C5—C6	178.8 (8)
C1—N1—C32—C31	60.2 (7)	C4—C5—C6—C7	−71.7 (12)
C34—N1—C32—C31	−63.6 (8)	O1—C31—C32—N1	9.7 (11)
C33—N1—C32—C31	178.0 (6)	O2—C31—C32—N1	−171.0 (6)
N1—C1—C2—C3	174.7 (6)

(beh14) N-n-Tetradecyl N,N-Dimethyl Ammonio Acetic Acid Bromide

Crystal data

C18H38NO2^+·Br^−	Z = 2
Mr = 380.41	F(000) = 408
Triclinic, P1	Dx = 1.190 Mg m^−3
a = 6.778 (4) Å	Mo Kα radiation, λ = 0.71069 Å
b = 7.484 (1) Å	Cell parameters from 25 reflections
c = 21.348 (5) Å	θ = 12.7–18.8°
α = 87.34 (2)°	µ = 1.92 mm^−1
β = 86.96 (3)°	T = 298 K
γ = 79.04 (3)°	Plate, colourless
V = 1061.0 (5) Å^3	0.78 × 0.70 × 0.26 mm

Data collection

CAD4 diffractometer	3345 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.013
Graphite monochromator	θmax = 25.0°, θmin = 1.9°
θ/2θ scans	h = −8→8
Absorption correction: part of the refinement model (ΔF) absorption correction using the method of N. Walker and D. Stuart (1983). Acta Cryst A39, 158-166	k = −8→8
Tmin = 0.123, Tmax = 1.000	l = 0→25
3816 measured reflections	2 standard reflections every 50 min
3706 independent reflections	intensity decay: 5.8%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.101	Positional parameters refined, isotropic displacement parameter constrained to binding partner, exception: isotropic displacement parameter of H2 refined without constrainedaints
S = 0.97	Calculated w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
3705 reflections	(Δ/σ)max = 0.002
314 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.43 e Å^−3

Special details

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

Refinement. Refinement on F² for ALL reflections except for 1 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R

are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating R_factor_gt etc. and is not relevant to the choice of reflections for refinement. R-factors based

on F² are statistically about twice as large as those based on F, and R-

factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Br	0.22069 (3)	0.20898 (3)	0.099800 (12)	0.05183 (14)
O1	0.5159 (3)	0.6035 (3)	0.13844 (12)	0.0694 (6)
O2	0.5964 (4)	0.3865 (3)	0.06816 (12)	0.0653 (6)
H2	0.506 (6)	0.362 (5)	0.0774 (19)	0.074 (12)*
C31	0.6223 (4)	0.5317 (3)	0.09655 (13)	0.0463 (5)
C32	0.8064 (4)	0.5914 (3)	0.06615 (13)	0.0428 (5)
H32A	0.922 (5)	0.485 (5)	0.0638 (16)	0.064*
H32B	0.777 (5)	0.632 (4)	0.0257 (17)	0.064*
C33	1.0687 (4)	0.7669 (4)	0.05772 (14)	0.0508 (6)
H33A	1.116 (6)	0.875 (5)	0.0697 (18)	0.076*
H33B	1.021 (6)	0.786 (5)	0.0146 (18)	0.076*
H33C	1.178 (6)	0.650 (6)	0.0574 (19)	0.076*
C34	0.7317 (5)	0.9166 (4)	0.0942 (2)	0.0605 (7)
H34A	0.803 (6)	1.012 (6)	0.108 (2)	0.091*
H34B	0.630 (7)	0.893 (6)	0.126 (2)	0.091*
H34C	0.681 (6)	0.940 (6)	0.053 (2)	0.091*
N1	0.8822 (3)	0.7403 (2)	0.09673 (9)	0.0399 (4)
C1	0.9384 (4)	0.6793 (3)	0.16364 (12)	0.0460 (5)
H1A	0.801 (5)	0.663 (4)	0.1902 (16)	0.069*
H1B	1.005 (5)	0.563 (5)	0.1616 (17)	0.069*
C2	1.0551 (5)	0.7983 (4)	0.19573 (13)	0.0519 (6)
H2A	0.981 (5)	0.924 (5)	0.1921 (18)	0.078*
H2B	1.172 (6)	0.808 (5)	0.1760 (19)	0.078*
C3	1.1102 (5)	0.7170 (5)	0.26046 (14)	0.0582 (7)
H3A	1.146 (6)	0.587 (6)	0.2617 (19)	0.087*
H3B	0.990 (7)	0.727 (6)	0.289 (2)	0.087*
C4	1.2680 (5)	0.8031 (5)	0.28924 (15)	0.0612 (7)
H4A	1.392 (7)	0.791 (6)	0.258 (2)	0.092*
H4B	1.220 (7)	0.920 (6)	0.296 (2)	0.092*
C5	1.3262 (5)	0.7230 (5)	0.35395 (14)	0.0627 (7)
H5A	1.366 (6)	0.589 (6)	0.353 (2)	0.094*
H5B	1.223 (7)	0.750 (6)	0.378 (2)	0.094*
C6	1.4969 (5)	0.7968 (5)	0.3803 (2)	0.0645 (7)
H6A	1.465 (7)	0.934 (6)	0.385 (2)	0.097*
H6B	1.624 (7)	0.768 (6)	0.353 (2)	0.097*
C7	1.5562 (5)	0.7169 (5)	0.44505 (15)	0.0645 (8)
H7A	1.446 (7)	0.747 (6)	0.474 (2)	0.097*
H7B	1.584 (6)	0.581 (6)	0.445 (2)	0.097*
C8	1.7291 (5)	0.7871 (5)	0.47081 (15)	0.0637 (7)
H8A	1.700 (6)	0.922 (6)	0.470 (2)	0.096*
H8B	1.850 (7)	0.754 (6)	0.443 (2)	0.096*
C9	1.7872 (5)	0.7093 (5)	0.53600 (14)	0.0628 (7)
H9A	1.676 (7)	0.756 (6)	0.559 (2)	0.094*
H9B	1.824 (6)	0.563 (6)	0.5384 (19)	0.094*
C10	1.9601 (5)	0.7794 (5)	0.5619 (2)	0.0643 (8)
H10A	2.072 (7)	0.762 (6)	0.538 (2)	0.096*
H10B	1.935 (6)	0.909 (6)	0.563 (2)	0.096*
C11	2.0160 (5)	0.7042 (5)	0.62733 (14)	0.0628 (7)
H11A	1.891 (7)	0.737 (6)	0.657 (2)	0.094*
H11B	2.057 (6)	0.560 (6)	0.6306 (19)	0.094*
C12	2.1876 (5)	0.7762 (5)	0.65333 (15)	0.0643 (7)
H12A	2.163 (7)	0.902 (7)	0.653 (2)	0.096*
H12B	2.313 (7)	0.744 (6)	0.627 (2)	0.096*
C13	2.2417 (7)	0.7068 (6)	0.7190 (2)	0.0770 (9)
H13A	2.123 (8)	0.730 (6)	0.754 (3)	0.115*
H13B	2.274 (8)	0.584 (7)	0.719 (2)	0.115*
C14	2.4139 (8)	0.7808 (8)	0.7437 (2)	0.0936 (13)
H14A	2.470 (9)	0.716 (9)	0.773 (3)	0.140*
H14B	2.382 (10)	0.919 (10)	0.747 (3)	0.140*
H14C	2.524 (10)	0.753 (9)	0.714 (3)	0.140*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br	0.0509 (2)	0.0478 (2)	0.0569 (2)	−0.00967 (11)	−0.00460 (12)	0.00039 (12)
O1	0.0543 (11)	0.0822 (14)	0.0728 (15)	−0.0176 (10)	0.0234 (11)	−0.0268 (12)
O2	0.0595 (12)	0.0699 (13)	0.072 (2)	−0.0259 (10)	0.0172 (11)	−0.0238 (11)
C31	0.0407 (12)	0.0501 (12)	0.0472 (15)	−0.0052 (10)	0.0003 (11)	−0.0072 (11)
C32	0.0455 (12)	0.0439 (12)	0.0383 (13)	−0.0069 (10)	0.0031 (10)	−0.0075 (10)
C33	0.0552 (15)	0.061 (2)	0.0386 (14)	−0.0191 (12)	0.0070 (12)	−0.0051 (11)
C34	0.064 (2)	0.0452 (13)	0.066 (2)	0.0075 (12)	−0.005 (2)	−0.0074 (13)
N1	0.0438 (10)	0.0400 (9)	0.0339 (11)	−0.0035 (8)	0.0052 (8)	−0.0059 (8)
C1	0.0558 (14)	0.0486 (12)	0.0327 (13)	−0.0080 (11)	0.0030 (11)	−0.0048 (10)
C2	0.061 (2)	0.0577 (15)	0.0381 (14)	−0.0126 (12)	−0.0005 (12)	−0.0054 (11)
C3	0.069 (2)	0.071 (2)	0.0374 (15)	−0.0211 (14)	0.0019 (13)	−0.0045 (13)
C4	0.067 (2)	0.075 (2)	0.044 (2)	−0.0198 (15)	−0.0033 (14)	−0.0060 (14)
C5	0.067 (2)	0.084 (2)	0.039 (2)	−0.020 (2)	0.0024 (13)	−0.0075 (14)
C6	0.070 (2)	0.081 (2)	0.047 (2)	−0.025 (2)	−0.0023 (14)	−0.0058 (14)
C7	0.069 (2)	0.090 (2)	0.038 (2)	−0.024 (2)	0.0010 (14)	−0.0077 (14)
C8	0.066 (2)	0.086 (2)	0.042 (2)	−0.023 (2)	−0.0004 (14)	−0.0037 (14)
C9	0.067 (2)	0.085 (2)	0.039 (2)	−0.021 (2)	0.0015 (13)	−0.0057 (14)
C10	0.068 (2)	0.085 (2)	0.043 (2)	−0.024 (2)	0.0017 (14)	−0.0018 (15)
C11	0.071 (2)	0.081 (2)	0.040 (2)	−0.022 (2)	0.0018 (14)	−0.0048 (14)
C12	0.069 (2)	0.083 (2)	0.044 (2)	−0.021 (2)	−0.0001 (14)	−0.0026 (14)
C13	0.091 (2)	0.094 (2)	0.049 (2)	−0.027 (2)	−0.009 (2)	0.003 (2)
C14	0.102 (3)	0.120 (4)	0.064 (3)	−0.030 (3)	−0.026 (2)	−0.002 (2)

Geometric parameters (Å, º)

O1—C31	1.199 (3)	C5—H5A	0.99 (4)
O2—C31	1.313 (3)	C5—H5B	0.84 (5)
O2—H2	0.69 (4)	C6—C7	1.523 (4)
C31—C32	1.509 (4)	C6—H6A	1.02 (4)
C32—N1	1.501 (3)	C6—H6B	1.01 (5)
C32—H32A	1.01 (4)	C7—C8	1.510 (4)
C32—H32B	0.92 (4)	C7—H7A	0.95 (5)
C33—N1	1.516 (3)	C7—H7B	1.00 (4)
C33—H33A	0.97 (4)	C8—C9	1.525 (4)
C33—H33B	0.99 (4)	C8—H8A	0.99 (4)
C33—H33C	1.03 (4)	C8—H8B	0.99 (5)
C34—N1	1.507 (3)	C9—C10	1.511 (4)
C34—H34A	1.00 (4)	C9—H9A	0.89 (5)
C34—H34B	0.97 (5)	C9—H9B	1.08 (4)
C34—H34C	0.96 (4)	C10—C11	1.522 (4)
N1—C1	1.525 (3)	C10—H10A	0.88 (5)
C1—C2	1.507 (4)	C10—H10B	0.95 (4)
C1—H1A	1.09 (4)	C11—C12	1.512 (4)
C1—H1B	0.90 (4)	C11—H11A	1.03 (5)
C2—C3	1.519 (4)	C11—H11B	1.06 (4)
C2—H2A	0.98 (4)	C12—C13	1.512 (4)
C2—H2B	0.89 (4)	C12—H12A	0.92 (5)
C3—C4	1.518 (4)	C12—H12B	0.99 (5)
C3—H3A	0.95 (4)	C13—C14	1.511 (6)
C3—H3B	0.98 (4)	C13—H13A	1.06 (5)
C4—C5	1.521 (4)	C13—H13B	0.90 (5)
C4—H4A	1.04 (4)	C14—H14A	0.83 (7)
C4—H4B	0.89 (4)	C14—H14B	1.02 (7)
C5—C6	1.517 (4)	C14—H14C	0.94 (6)
C31—O2—H2	111 (4)	C4—C5—H5B	106 (3)
O1—C31—O2	125.5 (2)	H5A—C5—H5B	110 (4)
O1—C31—C32	126.9 (2)	C5—C6—C7	114.0 (3)
O2—C31—C32	107.6 (2)	C5—C6—H6A	113 (3)
N1—C32—C31	117.0 (2)	C7—C6—H6A	106 (3)
N1—C32—H32A	106.5 (18)	C5—C6—H6B	111 (2)
C31—C32—H32A	110.2 (19)	C7—C6—H6B	105 (3)
N1—C32—H32B	107.2 (19)	H6A—C6—H6B	107 (3)
C31—C32—H32B	108 (2)	C8—C7—C6	114.1 (3)
H32A—C32—H32B	108 (3)	C8—C7—H7A	106 (3)
N1—C33—H33A	111 (2)	C6—C7—H7A	110 (3)
N1—C33—H33B	104 (2)	C8—C7—H7B	111 (2)
H33A—C33—H33B	109 (3)	C6—C7—H7B	110 (3)
N1—C33—H33C	112 (2)	H7A—C7—H7B	105 (3)
H33A—C33—H33C	114 (3)	C7—C8—C9	114.3 (3)
H33B—C33—H33C	106 (3)	C7—C8—H8A	110 (3)
N1—C34—H34A	106 (2)	C9—C8—H8A	111 (3)
N1—C34—H34B	102 (3)	C7—C8—H8B	109 (3)
H34A—C34—H34B	110 (4)	C9—C8—H8B	107 (3)
N1—C34—H34C	110 (3)	H8A—C8—H8B	105 (3)
H34A—C34—H34C	114 (3)	C10—C9—C8	114.4 (3)
H34B—C34—H34C	113 (4)	C10—C9—H9A	107 (3)
C32—N1—C34	111.3 (2)	C8—C9—H9A	101 (3)
C32—N1—C33	105.3 (2)	C10—C9—H9B	108 (2)
C34—N1—C33	108.2 (2)	C8—C9—H9B	113 (2)
C32—N1—C1	109.6 (2)	H9A—C9—H9B	114 (4)
C34—N1—C1	112.4 (2)	C9—C10—C11	114.4 (3)
C33—N1—C1	109.8 (2)	C9—C10—H10A	115 (3)
C2—C1—N1	115.4 (2)	C11—C10—H10A	107 (3)
C2—C1—H1A	112.3 (17)	C9—C10—H10B	112 (3)
N1—C1—H1A	107.8 (18)	C11—C10—H10B	107 (3)
C2—C1—H1B	113 (2)	H10A—C10—H10B	100 (4)
N1—C1—H1B	106 (2)	C12—C11—C10	114.3 (3)
H1A—C1—H1B	102 (3)	C12—C11—H11A	108 (2)
C1—C2—C3	110.0 (2)	C10—C11—H11A	108 (2)
C1—C2—H2A	108 (2)	C12—C11—H11B	106 (2)
C3—C2—H2A	119 (2)	C10—C11—H11B	114 (2)
C1—C2—H2B	114 (3)	H11A—C11—H11B	106 (3)
C3—C2—H2B	105 (3)	C11—C12—C13	115.0 (3)
H2A—C2—H2B	102 (3)	C11—C12—H12A	111 (3)
C4—C3—C2	112.8 (3)	C13—C12—H12A	109 (3)
C4—C3—H3A	112 (2)	C11—C12—H12B	112 (3)
C2—C3—H3A	113 (2)	C13—C12—H12B	106 (3)
C4—C3—H3B	110 (2)	H12A—C12—H12B	104 (4)
C2—C3—H3B	111 (2)	C14—C13—C12	113.8 (3)
H3A—C3—H3B	97 (3)	C14—C13—H13A	107 (3)
C3—C4—C5	113.7 (3)	C12—C13—H13A	116 (3)
C3—C4—H4A	108 (2)	C14—C13—H13B	109 (3)
C5—C4—H4A	111 (2)	C12—C13—H13B	109 (3)
C3—C4—H4B	110 (3)	H13A—C13—H13B	102 (4)
C5—C4—H4B	104 (3)	C13—C14—H14A	113 (5)
H4A—C4—H4B	110 (4)	C13—C14—H14B	113 (4)
C6—C5—C4	113.7 (3)	H14A—C14—H14B	120 (6)
C6—C5—H5A	108 (2)	C13—C14—H14C	107 (4)
C4—C5—H5A	110 (2)	H14A—C14—H14C	95 (5)
C6—C5—H5B	109 (3)	H14B—C14—H14C	107 (5)
O1—C31—C32—N1	9.0 (4)	C2—C3—C4—C5	−179.7 (3)
O2—C31—C32—N1	−171.9 (2)	C3—C4—C5—C6	174.8 (3)
C31—C32—N1—C34	−64.7 (3)	C4—C5—C6—C7	−179.9 (3)
C31—C32—N1—C33	178.3 (2)	C5—C6—C7—C8	178.7 (3)
C31—C32—N1—C1	60.3 (3)	C6—C7—C8—C9	179.2 (3)
C32—N1—C1—C2	168.2 (2)	C7—C8—C9—C10	−180.0 (3)
C34—N1—C1—C2	−67.4 (3)	C8—C9—C10—C11	179.1 (3)
C33—N1—C1—C2	53.1 (3)	C9—C10—C11—C12	−179.4 (3)
N1—C1—C2—C3	−177.1 (2)	C10—C11—C12—C13	178.5 (3)
C1—C2—C3—C4	166.4 (3)	C11—C12—C13—C14	179.9 (4)

(beh16) N-n-Hexadecyl N,N-Dimethyl Ammonio Acetic Acid Bromide

Crystal data

C20H42NO2^+·Br^−	Z = 2
Mr = 408.46	F(000) = 440
Triclinic, P1	Dx = 1.179 Mg m^−3
a = 6.762 (3) Å	Mo Kα radiation, λ = 0.71069 Å
b = 7.466 (2) Å	Cell parameters from 25 reflections
c = 23.40 (2) Å	θ = 13–16°
α = 86.90 (5)°	µ = 1.80 mm^−1
β = 83.14 (5)°	T = 298 K
γ = 78.87 (3)°	Plate, colourless
V = 1150.3 (11) Å^3	0.38 × 0.16 × 0.05 mm

Data collection

CAD4 diffractometer	1849 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
Graphite monochromator	θmax = 20.0°, θmin = 1.8°
θ/2θ scans	h = −6→6
Absorption correction: part of the refinement model (ΔF) absorption correction using the method of N. Walker and D. Stuart (1983). Acta Cryst A39, 158-166	k = −7→7
Tmin = 0.269, Tmax = 1.000	l = 0→22
2368 measured reflections	2 standard reflections every 30 min
2145 independent reflections	intensity decay: 2.3%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	Position relative to binding partner calculated and kept fixed during refinement, isotropic displacement parameter constrained to binding partner. exception: all parameters of H2 refined without constrainedaints
S = 0.89	Calculated w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
2144 reflections	(Δ/σ)max = 0.013
221 parameters	Δρmax = 0.42 e Å^−3
0 restraints	Δρmin = −0.39 e Å^−3

Special details

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

Refinement. Refinement on F² for ALL reflections except for 1 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating R_factor_gt etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Br	0.19972 (7)	0.20940 (6)	0.09149 (2)	0.0554 (3)
O1	0.4865 (6)	0.6048 (5)	0.1267 (2)	0.0708 (10)
O2	0.5812 (6)	0.3865 (5)	0.0621 (2)	0.0672 (10)
H2	0.470 (13)	0.341 (12)	0.079 (3)	0.17 (4)*
C31	0.6001 (7)	0.5320 (7)	0.0887 (2)	0.0487 (13)
C32	0.7919 (6)	0.5918 (6)	0.0607 (2)	0.0440 (12)
H32A	0.9007 (6)	0.4858 (6)	0.0592 (2)	0.057*
H32B	0.7716 (6)	0.6313 (6)	0.0213 (2)	0.057*
C33	1.0550 (7)	0.7675 (7)	0.0528 (2)	0.0513 (13)
H33A	1.1534 (7)	0.6561 (7)	0.0535 (2)	0.067*
H33B	1.1068 (7)	0.8634 (7)	0.0683 (2)	0.067*
H33C	1.0280 (7)	0.7997 (7)	0.0139 (2)	0.067*
C34	0.7109 (8)	0.9162 (6)	0.0870 (2)	0.0622 (14)
H34A	0.7592 (8)	1.0092 (6)	0.1051 (2)	0.081*
H34B	0.5833 (8)	0.8988 (6)	0.1071 (2)	0.081*
H34C	0.6934 (8)	0.9529 (6)	0.0477 (2)	0.081*
N1	0.8615 (5)	0.7411 (5)	0.0887 (2)	0.0412 (9)
C1	0.9035 (7)	0.6800 (6)	0.1497 (2)	0.0477 (12)
H1A	0.7752 (7)	0.6738 (6)	0.1725 (2)	0.062*
H1B	0.9840 (7)	0.5575 (6)	0.1488 (2)	0.062*
C2	1.0117 (7)	0.7994 (7)	0.1798 (2)	0.0528 (13)
H2A	0.9289 (7)	0.9205 (7)	0.1835 (2)	0.069*
H2B	1.1386 (7)	0.8105 (7)	0.1570 (2)	0.069*
C3	1.0537 (8)	0.7190 (7)	0.2387 (2)	0.0611 (14)
H3A	1.1060 (8)	0.5890 (7)	0.2357 (2)	0.079*
H3B	0.9274 (8)	0.7345 (7)	0.2640 (2)	0.079*
C4	1.2039 (8)	0.8058 (7)	0.2652 (2)	0.0612 (14)
H4A	1.1509 (8)	0.9357 (7)	0.2682 (2)	0.080*
H4B	1.3294 (8)	0.7910 (7)	0.2396 (2)	0.080*
C5	1.2501 (8)	0.7275 (7)	0.3241 (2)	0.0617 (14)
H5A	1.1269 (8)	0.7533 (7)	0.3505 (2)	0.080*
H5B	1.2892 (8)	0.5959 (7)	0.3219 (2)	0.080*
C6	1.4149 (8)	0.7989 (8)	0.3489 (2)	0.0651 (15)
H6A	1.3761 (8)	0.9306 (8)	0.3508 (2)	0.085*
H6B	1.5383 (8)	0.7723 (8)	0.3226 (2)	0.085*
C7	1.4605 (8)	0.7217 (8)	0.4081 (2)	0.068 (2)
H7A	1.3380 (8)	0.7504 (8)	0.4346 (2)	0.089*
H7B	1.4970 (8)	0.5898 (8)	0.4063 (2)	0.089*
C8	1.6278 (8)	0.7916 (8)	0.4316 (2)	0.0659 (15)
H8A	1.5915 (8)	0.9236 (8)	0.4333 (2)	0.086*
H8B	1.7506 (8)	0.7625 (8)	0.4052 (2)	0.086*
C9	1.6718 (8)	0.7142 (8)	0.4909 (2)	0.0655 (15)
H9A	1.5493 (8)	0.7440 (8)	0.5174 (2)	0.085*
H9B	1.7071 (8)	0.5822 (8)	0.4893 (2)	0.085*
C10	1.8401 (8)	0.7831 (7)	0.5143 (2)	0.0650 (15)
H10A	1.8050 (8)	0.9152 (7)	0.5157 (2)	0.085*
H10B	1.9626 (8)	0.7528 (7)	0.4878 (2)	0.085*
C11	1.8846 (8)	0.7068 (8)	0.5737 (2)	0.0659 (15)
H11A	1.7615 (8)	0.7359 (8)	0.6000 (2)	0.086*
H11B	1.9208 (8)	0.5748 (8)	0.5721 (2)	0.086*
C12	2.0521 (8)	0.7765 (8)	0.5979 (2)	0.0662 (15)
H12A	2.0166 (8)	0.9086 (8)	0.5991 (2)	0.086*
H12B	2.1756 (8)	0.7462 (8)	0.5718 (2)	0.086*
C13	2.0942 (8)	0.7014 (8)	0.6575 (2)	0.067 (2)
H13A	1.9707 (8)	0.7313 (8)	0.6836 (2)	0.087*
H13B	2.1306 (8)	0.5693 (8)	0.6563 (2)	0.087*
C14	2.2612 (8)	0.7729 (8)	0.6812 (2)	0.068 (2)
H14A	2.2264 (8)	0.9051 (8)	0.6813 (2)	0.089*
H14B	2.3853 (8)	0.7401 (8)	0.6556 (2)	0.089*
C15	2.3015 (10)	0.7027 (9)	0.7416 (2)	0.081 (2)
H15A	2.1776 (10)	0.7348 (9)	0.7674 (2)	0.105*
H15B	2.3380 (10)	0.5705 (9)	0.7417 (2)	0.105*
C16	2.4677 (10)	0.7772 (10)	0.7644 (3)	0.097 (2)
H16A	2.4855 (10)	0.7276 (10)	0.8026 (3)	0.127*
H16B	2.4315 (10)	0.9079 (10)	0.7655 (3)	0.127*
H16C	2.5920 (10)	0.7434 (10)	0.7398 (3)	0.127*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br	0.0546 (4)	0.0517 (4)	0.0604 (4)	−0.0109 (2)	−0.0078 (3)	0.0001 (3)
O1	0.056 (2)	0.082 (3)	0.072 (3)	−0.018 (2)	0.020 (2)	−0.031 (2)
O2	0.064 (2)	0.068 (3)	0.072 (3)	−0.022 (2)	0.007 (2)	−0.025 (2)
C31	0.043 (3)	0.052 (3)	0.047 (3)	0.000 (3)	−0.001 (3)	−0.005 (3)
C32	0.049 (3)	0.043 (3)	0.037 (3)	−0.002 (2)	0.001 (2)	−0.010 (2)
C33	0.052 (3)	0.061 (3)	0.040 (3)	−0.017 (2)	0.006 (2)	−0.006 (2)
C34	0.067 (3)	0.045 (3)	0.070 (4)	0.003 (3)	−0.009 (3)	−0.009 (3)
N1	0.044 (2)	0.039 (2)	0.037 (2)	−0.002 (2)	0.002 (2)	−0.011 (2)
C1	0.059 (3)	0.049 (3)	0.034 (3)	−0.008 (2)	−0.002 (2)	−0.005 (2)
C2	0.058 (3)	0.061 (3)	0.038 (3)	−0.009 (2)	−0.001 (3)	−0.009 (3)
C3	0.070 (3)	0.076 (3)	0.040 (3)	−0.020 (3)	−0.003 (3)	−0.010 (3)
C4	0.062 (3)	0.075 (4)	0.046 (4)	−0.014 (3)	−0.001 (3)	−0.011 (3)
C5	0.068 (3)	0.085 (4)	0.034 (3)	−0.021 (3)	0.002 (3)	−0.013 (3)
C6	0.066 (3)	0.086 (4)	0.044 (4)	−0.017 (3)	−0.004 (3)	−0.006 (3)
C7	0.071 (4)	0.093 (4)	0.041 (3)	−0.022 (3)	0.003 (3)	−0.009 (3)
C8	0.067 (3)	0.083 (4)	0.049 (4)	−0.019 (3)	0.001 (3)	−0.011 (3)
C9	0.068 (3)	0.091 (4)	0.040 (3)	−0.024 (3)	−0.002 (3)	−0.007 (3)
C10	0.072 (4)	0.085 (4)	0.041 (3)	−0.024 (3)	0.000 (3)	−0.009 (3)
C11	0.069 (3)	0.084 (4)	0.047 (4)	−0.022 (3)	0.004 (3)	−0.016 (3)
C12	0.073 (4)	0.086 (4)	0.042 (3)	−0.023 (3)	−0.003 (3)	−0.006 (3)
C13	0.075 (4)	0.084 (4)	0.046 (4)	−0.025 (3)	−0.002 (3)	−0.007 (3)
C14	0.077 (4)	0.089 (4)	0.041 (4)	−0.022 (3)	−0.002 (3)	−0.004 (3)
C15	0.096 (4)	0.099 (4)	0.052 (4)	−0.031 (4)	−0.005 (3)	−0.004 (3)
C16	0.110 (5)	0.123 (5)	0.067 (4)	−0.033 (4)	−0.022 (4)	0.000 (4)

Geometric parameters (Å, º)

O1—C31	1.185 (6)	C6—H6A	0.97
O2—C31	1.315 (6)	C6—H6B	0.97
O2—H2	0.92 (9)	C7—C8	1.505 (7)
C31—C32	1.516 (7)	C7—H7A	0.97
C32—N1	1.499 (5)	C7—H7B	0.97
C32—H32A	0.97	C8—C9	1.514 (7)
C32—H32B	0.97	C8—H8A	0.97
C33—N1	1.508 (6)	C8—H8B	0.97
C33—H33A	0.96	C9—C10	1.505 (7)
C33—H33B	0.96	C9—H9A	0.97
C33—H33C	0.96	C9—H9B	0.97
C34—N1	1.496 (6)	C10—C11	1.515 (7)
C34—H34A	0.96	C10—H10A	0.97
C34—H34B	0.96	C10—H10B	0.97
C34—H34C	0.96	C11—C12	1.512 (7)
N1—C1	1.518 (6)	C11—H11A	0.97
C1—C2	1.505 (6)	C11—H11B	0.97
C1—H1A	0.97	C12—C13	1.513 (7)
C1—H1B	0.97	C12—H12A	0.97
C2—C3	1.510 (7)	C12—H12B	0.97
C2—H2A	0.97	C13—C14	1.511 (7)
C2—H2B	0.97	C13—H13A	0.97
C3—C4	1.511 (7)	C13—H13B	0.97
C3—H3A	0.97	C14—C15	1.518 (7)
C3—H3B	0.97	C14—H14A	0.97
C4—C5	1.512 (7)	C14—H14B	0.97
C4—H4A	0.97	C15—C16	1.508 (8)
C4—H4B	0.97	C15—H15A	0.97
C5—C6	1.509 (7)	C15—H15B	0.97
C5—H5A	0.97	C16—H16A	0.96
C5—H5B	0.97	C16—H16B	0.96
C6—C7	1.514 (7)	C16—H16C	0.96
C31—O2—H2	111 (5)	C7—C6—H6B	108.5 (3)
O1—C31—O2	126.4 (5)	H6A—C6—H6B	107.5
O1—C31—C32	126.3 (5)	C8—C7—C6	114.6 (5)
O2—C31—C32	107.2 (5)	C8—C7—H7A	108.6 (3)
N1—C32—C31	117.3 (4)	C6—C7—H7A	108.6 (3)
N1—C32—H32A	108.0 (2)	C8—C7—H7B	108.6 (3)
C31—C32—H32A	108.0 (2)	C6—C7—H7B	108.6 (3)
N1—C32—H32B	108.0 (2)	H7A—C7—H7B	107.6
C31—C32—H32B	108.0 (3)	C7—C8—C9	114.2 (5)
H32A—C32—H32B	107.2	C7—C8—H8A	108.7 (3)
N1—C33—H33A	109.5 (2)	C9—C8—H8A	108.7 (3)
N1—C33—H33B	109.5 (2)	C7—C8—H8B	108.7 (3)
H33A—C33—H33B	109.5	C9—C8—H8B	108.7 (3)
N1—C33—H33C	109.5 (2)	H8A—C8—H8B	107.6
H33A—C33—H33C	109.5	C10—C9—C8	114.2 (4)
H33B—C33—H33C	109.5	C10—C9—H9A	108.7 (3)
N1—C34—H34A	109.5 (2)	C8—C9—H9A	108.7 (3)
N1—C34—H34B	109.5 (2)	C10—C9—H9B	108.7 (3)
H34A—C34—H34B	109.5	C8—C9—H9B	108.7 (3)
N1—C34—H34C	109.5 (3)	H9A—C9—H9B	107.6
H34A—C34—H34C	109.5	C9—C10—C11	114.5 (4)
H34B—C34—H34C	109.5	C9—C10—H10A	108.6 (3)
C34—N1—C32	111.2 (3)	C11—C10—H10A	108.6 (3)
C34—N1—C33	108.5 (4)	C9—C10—H10B	108.6 (3)
C32—N1—C33	105.3 (3)	C11—C10—H10B	108.6 (3)
C34—N1—C1	112.1 (3)	H10A—C10—H10B	107.6
C32—N1—C1	109.3 (3)	C12—C11—C10	115.0 (5)
C33—N1—C1	110.2 (3)	C12—C11—H11A	108.5 (3)
C2—C1—N1	115.7 (4)	C10—C11—H11A	108.5 (3)
C2—C1—H1A	108.4 (3)	C12—C11—H11B	108.5 (3)
N1—C1—H1A	108.4 (2)	C10—C11—H11B	108.5 (3)
C2—C1—H1B	108.4 (3)	H11A—C11—H11B	107.5
N1—C1—H1B	108.4 (2)	C11—C12—C13	114.7 (5)
H1A—C1—H1B	107.4	C11—C12—H12A	108.6 (3)
C1—C2—C3	110.5 (4)	C13—C12—H12A	108.6 (3)
C1—C2—H2A	109.6 (3)	C11—C12—H12B	108.6 (3)
C3—C2—H2A	109.6 (3)	C13—C12—H12B	108.6 (3)
C1—C2—H2B	109.6 (3)	H12A—C12—H12B	107.6
C3—C2—H2B	109.6 (3)	C14—C13—C12	114.1 (4)
H2A—C2—H2B	108.1	C14—C13—H13A	108.7 (3)
C2—C3—C4	112.9 (4)	C12—C13—H13A	108.7 (3)
C2—C3—H3A	109.0 (3)	C14—C13—H13B	108.7 (3)
C4—C3—H3A	109.0 (3)	C12—C13—H13B	108.7 (3)
C2—C3—H3B	109.0 (3)	H13A—C13—H13B	107.6
C4—C3—H3B	109.0 (3)	C13—C14—C15	114.8 (5)
H3A—C3—H3B	107.8	C13—C14—H14A	108.6 (3)
C3—C4—C5	114.2 (4)	C15—C14—H14A	108.6 (3)
C3—C4—H4A	108.7 (3)	C13—C14—H14B	108.6 (3)
C5—C4—H4A	108.7 (3)	C15—C14—H14B	108.6 (3)
C3—C4—H4B	108.7 (3)	H14A—C14—H14B	107.6
C5—C4—H4B	108.7 (3)	C16—C15—C14	113.7 (5)
H4A—C4—H4B	107.6	C16—C15—H15A	108.8 (4)
C6—C5—C4	115.1 (4)	C14—C15—H15A	108.8 (3)
C6—C5—H5A	108.5 (3)	C16—C15—H15B	108.8 (4)
C4—C5—H5A	108.5 (3)	C14—C15—H15B	108.8 (3)
C6—C5—H5B	108.5 (3)	H15A—C15—H15B	107.7
C4—C5—H5B	108.5 (3)	C15—C16—H16A	109.5 (3)
H5A—C5—H5B	107.5	C15—C16—H16B	109.5 (4)
C5—C6—C7	115.2 (4)	H16A—C16—H16B	109.5
C5—C6—H6A	108.5 (3)	C15—C16—H16C	109.5 (4)
C7—C6—H6A	108.5 (3)	H16A—C16—H16C	109.5
C5—C6—H6B	108.5 (3)	H16B—C16—H16C	109.5
O1—C31—C32—N1	9.1 (7)	C3—C4—C5—C6	174.2 (5)
O2—C31—C32—N1	−172.1 (4)	C4—C5—C6—C7	179.6 (5)
C31—C32—N1—C34	−64.0 (5)	C5—C6—C7—C8	178.9 (5)
C31—C32—N1—C33	178.6 (4)	C6—C7—C8—C9	179.8 (5)
C31—C32—N1—C1	60.3 (5)	C7—C8—C9—C10	179.6 (5)
C34—N1—C1—C2	−67.3 (5)	C8—C9—C10—C11	179.8 (5)
C32—N1—C1—C2	168.9 (4)	C9—C10—C11—C12	−179.4 (5)
C33—N1—C1—C2	53.6 (5)	C10—C11—C12—C13	179.4 (5)
N1—C1—C2—C3	−177.1 (4)	C11—C12—C13—C14	−179.7 (5)
C1—C2—C3—C4	166.3 (4)	C12—C13—C14—C15	178.4 (5)
C2—C3—C4—C5	−179.7 (4)	C13—C14—C15—C16	−179.6 (5)