N-(3-Phenyl­prop­yl)guanidinium bromide

N-(3-Phenyl­prop­yl)guanidinium bromide, C₁₀H₁₆N₃⁺·Br⁻, was synthesized by the reaction of 2-ethyl-2-pseudourea hydro­bromide with 3-phenyl-1-propyl­amine. N—H...Br hydrogen bonds stabilize the bromide anions in channels along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.013 Å
• R factor = 0.058
• wR factor = 0.141
• Data-to-parameter ratio = 21.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.88
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.78
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         13

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.25
           From the CIF: _reflns_number_total               2724
           Count of symmetry unique reflns         1489
           Completeness (_total/calc)            182.94%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1235
           Fraction of Friedel pairs measured     0.829
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2003); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

N-(3-Phenylpropyl)guanidinium bromide

Crystal data

C10H16N3^+·Br^−	F(000) = 528
Mr = 258.17	Dx = 1.429 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 5032 reflections
a = 10.5205 (18) Å	θ = 2.7–30.5°
b = 11.784 (2) Å	µ = 3.40 mm^−1
c = 10.3702 (17) Å	T = 100 K
β = 111.056 (3)°	Plate, colorless
V = 1199.8 (3) Å^3	0.33 × 0.23 × 0.02 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer	2724 independent reflections
Radiation source: fine-focus sealed tube	2501 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
ω scans	θmax = 28.3°, θmin = 2.7°
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 2003)	h = −13→14
Tmin = 0.299, Tmax = 0.934	k = −15→15
5112 measured reflections	l = −13→13

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.058	H-atom parameters constrained
wR(F^2) = 0.141	w = 1/[σ^2(Fo^2) + (0.0309P)^2 + 7.8027P] where P = (Fo^2 + 2Fc^2)/3
S = 1.14	(Δ/σ)max < 0.001
2724 reflections	Δρmax = 2.19 e Å^−3
128 parameters	Δρmin = −0.79 e Å^−3
2 restraints	Absolute structure: Flack (1983), 1246 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.09 (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 of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(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
Br1	0.71055 (8)	0.87770 (5)	0.18953 (8)	0.02567 (18)
C1	0.3989 (7)	0.3219 (5)	0.5799 (7)	0.0221 (13)
C2	0.4699 (7)	0.3874 (6)	0.8195 (7)	0.0245 (14)
H2A	0.3862	0.3679	0.8374	0.029*
H2B	0.4638	0.4681	0.7914	0.029*
C3	0.5931 (10)	0.3703 (6)	0.9501 (8)	0.0237 (16)
H3A	0.6761	0.3951	0.9341	0.028*
H3B	0.6031	0.2887	0.9743	0.028*
C4	0.5783 (8)	0.4381 (7)	1.0694 (9)	0.0316 (16)
H4A	0.5726	0.5198	1.0460	0.038*
H4B	0.4921	0.4162	1.0808	0.038*
C5	0.6925 (8)	0.4200 (6)	1.2018 (9)	0.0241 (17)
C6	0.6836 (9)	0.3459 (7)	1.3034 (8)	0.0331 (17)
H6	0.6016	0.3047	1.2869	0.040*
C7	0.7898 (12)	0.3308 (9)	1.4260 (9)	0.040 (2)
H7	0.7808	0.2778	1.4912	0.048*
C8	0.9082 (11)	0.3904 (8)	1.4565 (9)	0.040 (2)
H8	0.9805	0.3811	1.5428	0.048*
C9	0.9203 (9)	0.4651 (8)	1.3575 (9)	0.0374 (18)
H9	1.0024	0.5067	1.3759	0.045*
C10	0.8159 (8)	0.4793 (7)	1.2346 (9)	0.0327 (16)
H10	0.8268	0.5309	1.1690	0.039*
N1	0.2952 (6)	0.3952 (4)	0.5380 (6)	0.0213 (11)
H1A	0.2803	0.4411	0.5979	0.026*
H1B	0.2418	0.3975	0.4504	0.026*
N2	0.4190 (6)	0.2529 (5)	0.4873 (6)	0.0253 (12)
H2C	0.4867	0.2040	0.5134	0.030*
H2D	0.3647	0.2563	0.4002	0.030*
N3	0.4797 (6)	0.3163 (5)	0.7087 (6)	0.0215 (12)
H3	0.5455	0.2656	0.7305	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0275 (3)	0.0243 (3)	0.0219 (3)	−0.0115 (4)	0.0049 (2)	0.0053 (4)
C1	0.019 (3)	0.016 (3)	0.030 (4)	−0.003 (2)	0.007 (3)	0.000 (3)
C2	0.025 (3)	0.023 (3)	0.026 (4)	0.004 (3)	0.009 (3)	0.004 (3)
C3	0.027 (4)	0.022 (4)	0.018 (4)	0.005 (3)	0.003 (3)	0.007 (3)
C4	0.033 (4)	0.032 (4)	0.031 (4)	0.012 (3)	0.012 (4)	−0.003 (3)
C5	0.016 (4)	0.033 (3)	0.019 (4)	0.006 (3)	0.002 (3)	−0.005 (3)
C6	0.041 (4)	0.030 (4)	0.032 (4)	−0.001 (3)	0.018 (4)	−0.005 (3)
C7	0.063 (7)	0.037 (5)	0.020 (4)	0.011 (5)	0.013 (4)	0.001 (4)
C8	0.043 (5)	0.042 (5)	0.026 (5)	0.016 (4)	0.002 (4)	−0.011 (4)
C9	0.031 (4)	0.045 (5)	0.038 (5)	0.005 (4)	0.015 (4)	−0.010 (4)
C10	0.033 (4)	0.034 (4)	0.033 (4)	0.001 (3)	0.014 (4)	−0.004 (3)
N1	0.022 (3)	0.017 (3)	0.020 (3)	0.002 (2)	0.002 (2)	−0.002 (2)
N2	0.027 (3)	0.023 (3)	0.022 (3)	0.005 (2)	0.003 (3)	−0.002 (2)
N3	0.021 (3)	0.015 (3)	0.027 (3)	0.007 (2)	0.006 (2)	−0.001 (2)

Geometric parameters (Å, º)

C1—N3	1.302 (9)	C6—C7	1.369 (13)
C1—N2	1.331 (9)	C6—H6	0.9500
C1—N1	1.335 (9)	C7—C8	1.364 (15)
C2—N3	1.455 (9)	C7—H7	0.9500
C2—C3	1.515 (11)	C8—C9	1.393 (14)
C2—H2A	0.9900	C8—H8	0.9500
C2—H2B	0.9900	C9—C10	1.361 (13)
C3—C4	1.527 (11)	C9—H9	0.9500
C3—H3A	0.9900	C10—H10	0.9500
C3—H3B	0.9900	N1—H1A	0.8800
C4—C5	1.480 (13)	N1—H1B	0.8800
C4—H4A	0.9900	N2—H2C	0.8800
C4—H4B	0.9900	N2—H2D	0.8800
C5—C6	1.398 (11)	N3—H3	0.8800
C5—C10	1.404 (11)
N3—C1—N2	119.6 (6)	C7—C6—C5	121.8 (8)
N3—C1—N1	121.5 (6)	C7—C6—H6	119.1
N2—C1—N1	118.9 (6)	C5—C6—H6	119.1
N3—C2—C3	110.4 (6)	C8—C7—C6	121.4 (9)
N3—C2—H2A	109.6	C8—C7—H7	119.3
C3—C2—H2A	109.6	C6—C7—H7	119.3
N3—C2—H2B	109.6	C7—C8—C9	118.2 (9)
C3—C2—H2B	109.6	C7—C8—H8	120.9
H2A—C2—H2B	108.1	C9—C8—H8	120.9
C2—C3—C4	110.5 (7)	C10—C9—C8	120.7 (9)
C2—C3—H3A	109.5	C10—C9—H9	119.6
C4—C3—H3A	109.5	C8—C9—H9	119.6
C2—C3—H3B	109.5	C9—C10—C5	122.1 (9)
C4—C3—H3B	109.5	C9—C10—H10	119.0
H3A—C3—H3B	108.1	C5—C10—H10	119.0
C5—C4—C3	113.0 (6)	C1—N1—H1A	120.0
C5—C4—H4A	109.0	C1—N1—H1B	120.0
C3—C4—H4A	109.0	H1A—N1—H1B	120.0
C5—C4—H4B	109.0	C1—N2—H2C	120.0
C3—C4—H4B	109.0	C1—N2—H2D	120.0
H4A—C4—H4B	107.8	H2C—N2—H2D	120.0
C6—C5—C10	115.8 (8)	C1—N3—C2	125.1 (6)
C6—C5—C4	122.5 (7)	C1—N3—H3	117.4
C10—C5—C4	121.7 (7)	C2—N3—H3	117.4
N3—C2—C3—C4	−175.9 (6)	C7—C8—C9—C10	0.9 (12)
C2—C3—C4—C5	177.0 (6)	C8—C9—C10—C5	−0.1 (11)
C3—C4—C5—C6	−99.5 (8)	C6—C5—C10—C9	0.2 (10)
C3—C4—C5—C10	82.4 (9)	C4—C5—C10—C9	178.5 (7)
C10—C5—C6—C7	−1.1 (11)	N2—C1—N3—C2	179.3 (6)
C4—C5—C6—C7	−179.4 (7)	N1—C1—N3—C2	−1.0 (10)
C5—C6—C7—C8	2.0 (13)	C3—C2—N3—C1	−171.0 (6)
C6—C7—C8—C9	−1.8 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Br1^i	0.88	2.55	3.382 (5)	158
N1—H1B···Br1^ii	0.88	2.62	3.403 (6)	149
N2—H2C···Br1^iii	0.88	2.59	3.399 (6)	153
N2—H2D···Br1^ii	0.88	2.63	3.412 (6)	149
N3—H3···Br1^iii	0.88	2.56	3.393 (5)	157

Symmetry codes: (i) x−1/2, −y+3/2, z+1/2; (ii) x−1/2, y−1/2, z; (iii) x, −y+1, z+1/2.