Crystal structure of 2-cyano-1-methyl­pyridinium perchlorate

Nguyen, V.D.; McCormick, C.A.; Mague, J.T.; Koplitz, L.V.

doi:10.1107/S2056989015019155

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 11| November 2015| Pages o852-o853

https://doi.org/10.1107/S2056989015019155

Open

access

Crystal structure of 2-cyano-1-methylpyridinium perchlorate

Vu D. Nguyen,^a Cameron A. McCormick,^a Joel T. Mague ^b ^* and Lynn V. Koplitz ^a

^aDepartment of Chemistry, Loyola University, New Orleans, LA 70118, USA, and ^bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: joelt@tulane.edu

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 9 October 2015; accepted 10 October 2015; online 17 October 2015)

The asymmetric unit of the title salt, C₇H₇N₂⁺·ClO₄⁻, comprises two independent formula units. The solid-state structure comprises corrugated layers of cations and of anions, approximately parallel to (010). The supramolecular layers are stabilized and connected by C—H⋯O hydrogen bonding to consolidate a three-dimensional architecture. A close pyridinium–perchlorate N⋯O contact [2.867 (5) Å] is noted. The crystal was refined as an inversion twin.

Keywords: crystal structure; salt; pyridinium; perchlorate; hydrogen bonding.

CCDC reference: 1430590

1. Related literature

For structures of other salts of the 2-cyano-1-methylpyridinium cation, see: Koplitz et al. (2012 ); Kammer et al. (2013 ); Vaccaro et al. (2015 ). For structures of salts of the isomeric 2-cyanoanilinium cation, see: Zhang (2009 ); Cui & Chen (2010 ).

2. Experimental

2.1. Crystal data

C₇H₇N₂⁺·ClO₄⁻
M_r = 218.60
Monoclinic, P 2₁
a = 8.0112 (12) Å
b = 7.7011 (12) Å
c = 14.742 (2) Å
β = 90.982 (2)°
V = 909.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 150 K
0.19 × 0.14 × 0.13 mm

2.2. Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009 ) T_min = 0.93, T_max = 0.95
22843 measured reflections
22843 independent reflections
20913 reflections with I > 2σ(I)
R_int = 0.051

2.3. Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.109
S = 1.00
22843 reflections
256 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.34 e Å⁻³
Absolute structure: Flack x determined using 1908 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter: 0.04 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O1ⁱ	0.98	2.53	3.441 (5)	154
C1—H1C⋯O3	0.98	2.52	3.164 (5)	123
C3—H3⋯O5ⁱⁱ	0.95	2.54	3.326 (5)	140
C5—H5⋯O8ⁱⁱⁱ	0.95	2.66	3.262 (6)	122
C6—H6⋯O1ⁱ	0.95	2.55	3.415 (6)	152
C6—H6⋯O4ⁱ	0.95	2.65	3.534 (6)	155
C8—H8A⋯O1^iv	0.98	2.55	3.294 (6)	132
C8—H8B⋯O7^v	0.98	2.57	3.538 (6)	169
C8—H8C⋯O6	0.98	2.51	3.425 (5)	156
C10—H10⋯O2^vi	0.95	2.51	3.367 (5)	150
C12—H12⋯O2^vii	0.95	2.52	3.347 (5)	145
C13—H13⋯O6	0.95	2.35	3.247 (6)	156
Symmetry codes: (i) x-1, y, z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+2]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+2]$ ; (iv) x, y+1, z; (v) x+1, y, z; (vi) $[-x+2, y+{\script{1\over 2}}, -z+1]$ ; (vii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2014 ); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT and CELL_NOW (Sheldrick, 2008a ); program(s) used to solve structure: SHELXT (Sheldrick, 2015a ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b ); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b ).

Supporting information

CCDC reference: 1430590

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015019155/tk5395sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015019155/tk5395Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015019155/tk5395Isup3.cml

checkCIF report

Comment top

The asymmetric unit comprises two independent formula units. A portion of the C—H···O hydrogen bonding network which aids the packing of the several ions is shown in Fig. 1 with a fuller depiction appearing in Figs 2 and 3. The solid state structure consists of corrugated layers of cations and anions formed by C—H···O hydrogen bonding between them and approximately parallel to (010). These layers are held to one another by additional C—H···O interactions. The overall structure is essentially the same as found for the tetrafluoroborate salt (Vaccaro et al., 2015).

Related literature top

For structures of other salts of the 2-cyano-1-methylpyridinium cation, see: Koplitz et al. (2012); Kammer et al. (2013); Vaccaro et al. (2015). For structures of salts of the isomeric 2-cyanoanilinium cation, see: Zhang (2009); Cui & Chen (2010).

Experimental top

2-Cyano-1-methylpyridinium iodide (0.42 g, 1.70 mmol; m.p. 146–150°) was dissolved in a solution of silver perchlorate previously prepared by reacting Ag₂O (0.20 g, 0.86 mmol) with 1M aqueous HClO₄ (1.8 ml) in 8.0 ml of H₂O. After stirring, the precipitated AgI was removed by vacuum filtration. The filtrate was slowly evaporated to dryness in a freezer at about -5° over several months to form crystals suitable for single-crystal X-ray diffraction.

Structure description top

For structures of other salts of the 2-cyano-1-methylpyridinium cation, see: Koplitz et al. (2012); Kammer et al. (2013); Vaccaro et al. (2015). For structures of salts of the isomeric 2-cyanoanilinium cation, see: Zhang (2009); Cui & Chen (2010).

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014) and CELL_NOW (Sheldrick, 2008a); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).

Figures top

	Fig. 1. Perspective view of the asymmetric unit with 50% probability ellipsoids. C—H···O interactions are shown by dotted lines.
	Fig. 2. Packing viewed down the a axis showing an edge view of two corrugated layers and the C—H···O interaction (dotted line) holding them together.
	Fig. 3. Packing viewed down the b axis providing a plan view of the corrugated sheets with C—H···O interactions shown as dotted lines.

2-Cyano-1-methylpyridinium perchlorate top

Crystal data top

C₇H₇N₂⁺·ClO₄⁻	F(000) = 448
M_r = 218.60	D_x = 1.597 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 8.0112 (12) Å	Cell parameters from 9987 reflections
b = 7.7011 (12) Å	θ = 2.5–29.2°
c = 14.742 (2) Å	µ = 0.41 mm⁻¹
β = 90.982 (2)°	T = 150 K
V = 909.4 (2) Å³	Block, colourless
Z = 4	0.19 × 0.14 × 0.13 mm

Data collection top

Bruker SMART APEX CCD diffractometer	22843 independent reflections
Radiation source: fine-focus sealed tube	20913 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
Detector resolution: 8.3660 pixels mm^-1	θ_max = 29.2°, θ_min = 2.5°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009)	k = −10→10
T_min = 0.93, T_max = 0.95	l = −20→20
22843 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0531P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
22843 reflections	Δρ_max = 0.30 e Å⁻³
256 parameters	Δρ_min = −0.34 e Å⁻³
1 restraint	Absolute structure: Flack x determined using 1908 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (3)

Crystal data top

C₇H₇N₂⁺·ClO₄⁻	V = 909.4 (2) Å³
M_r = 218.60	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 8.0112 (12) Å	µ = 0.41 mm⁻¹
b = 7.7011 (12) Å	T = 150 K
c = 14.742 (2) Å	0.19 × 0.14 × 0.13 mm
β = 90.982 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	22843 independent reflections
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009)	20913 reflections with I > 2σ(I)
T_min = 0.93, T_max = 0.95	R_int = 0.051
22843 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.109	Δρ_max = 0.30 e Å⁻³
S = 1.00	Δρ_min = −0.34 e Å⁻³
22843 reflections	Absolute structure: Flack x determined using 1908 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
256 parameters	Absolute structure parameter: 0.04 (3)
1 restraint

Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, collected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = -30.00 and 210.00°. The scan time was 15 sec/frame. Analysis of 3152 reflections having I/σ(I) > 13 and chosen from the full data set with CELL_NOW (Sheldrick, 2008a) showed the crystal to belong to the monoclinic system and to be twinned by a 180° rotation about c*. The raw data were processed using the multi-component version of SAINT under control of the two-component orientation file generated by CELL_NOW.

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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.98 Å). All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. Refined as a 2-component twin.

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

	x	y	z	U_iso*/U_eq
N1	0.2547 (4)	0.1723 (5)	0.8742 (2)	0.0186 (7)
N2	0.6652 (5)	0.0531 (8)	0.8975 (3)	0.0424 (14)
C1	0.3149 (5)	0.1871 (7)	0.7797 (3)	0.0268 (10)
H1A	0.2255	0.2339	0.7406	0.040*
H1B	0.3474	0.0721	0.7577	0.040*
H1C	0.4115	0.2651	0.7785	0.040*
C2	0.3617 (5)	0.1208 (6)	0.9418 (3)	0.0204 (10)
C3	0.3089 (5)	0.1017 (7)	1.0292 (3)	0.0262 (11)
H3	0.3845	0.0658	1.0759	0.031*
C4	0.1425 (5)	0.1359 (7)	1.0482 (3)	0.0261 (11)
H4	0.1033	0.1237	1.1083	0.031*
C5	0.0358 (5)	0.1874 (7)	0.9798 (3)	0.0265 (11)
H5	−0.0780	0.2106	0.9921	0.032*
C6	0.0947 (5)	0.2053 (7)	0.8927 (3)	0.0237 (10)
H6	0.0208	0.2414	0.8453	0.028*
C7	0.5316 (5)	0.0839 (8)	0.9162 (3)	0.0266 (11)
Cl1	0.77813 (11)	0.34996 (12)	0.68489 (7)	0.0185 (2)
O1	0.9290 (4)	0.2488 (5)	0.6789 (3)	0.0300 (8)
O2	0.7857 (4)	0.4925 (4)	0.6214 (2)	0.0263 (7)
O3	0.6375 (4)	0.2420 (5)	0.6622 (3)	0.0295 (9)
O4	0.7628 (4)	0.4142 (5)	0.7754 (2)	0.0370 (9)
N3	0.7638 (4)	0.8780 (5)	0.6208 (3)	0.0167 (8)
N4	1.1905 (4)	0.9228 (7)	0.6055 (3)	0.0374 (12)
C8	0.8152 (5)	0.8446 (7)	0.7165 (3)	0.0214 (9)
H8A	0.8523	0.9534	0.7448	0.032*
H8B	0.9070	0.7604	0.7181	0.032*
H8C	0.7203	0.7979	0.7497	0.032*
C9	0.8788 (4)	0.9197 (6)	0.5573 (3)	0.0187 (9)
C10	0.8332 (5)	0.9575 (7)	0.4697 (3)	0.0232 (10)
H10	0.9152	0.9855	0.4263	0.028*
C11	0.6647 (5)	0.9542 (7)	0.4452 (3)	0.0254 (10)
H11	0.6295	0.9816	0.3850	0.030*
C12	0.5499 (5)	0.9103 (7)	0.5099 (4)	0.0253 (11)
H12	0.4345	0.9046	0.4942	0.030*
C13	0.6021 (4)	0.8747 (6)	0.5969 (3)	0.0214 (10)
H13	0.5216	0.8472	0.6413	0.026*
C14	1.0526 (5)	0.9217 (7)	0.5867 (4)	0.0259 (11)
Cl2	0.26845 (11)	0.66595 (14)	0.81449 (7)	0.0213 (2)
O5	0.3040 (4)	0.5521 (5)	0.8898 (2)	0.0329 (9)
O6	0.4209 (4)	0.7202 (7)	0.7750 (3)	0.0629 (16)
O7	0.1683 (5)	0.5742 (6)	0.7490 (3)	0.0436 (10)
O8	0.1756 (4)	0.8134 (5)	0.8449 (3)	0.0405 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0224 (14)	0.0147 (18)	0.0187 (19)	−0.0010 (15)	0.0002 (13)	0.0016 (17)
N2	0.0285 (19)	0.069 (4)	0.030 (3)	0.009 (2)	−0.0004 (17)	−0.009 (3)
C1	0.034 (2)	0.026 (3)	0.020 (2)	0.004 (2)	0.0063 (17)	0.004 (2)
C2	0.0181 (16)	0.018 (3)	0.025 (3)	−0.0009 (15)	−0.0016 (15)	−0.003 (2)
C3	0.026 (2)	0.030 (3)	0.023 (3)	0.0038 (19)	−0.0050 (17)	−0.001 (2)
C4	0.0295 (19)	0.028 (3)	0.021 (2)	−0.0039 (18)	0.0058 (16)	−0.001 (2)
C5	0.0207 (18)	0.027 (3)	0.032 (3)	0.0011 (19)	0.0009 (16)	0.000 (2)
C6	0.0229 (18)	0.023 (3)	0.025 (3)	0.0020 (17)	−0.0027 (16)	−0.001 (2)
C7	0.026 (2)	0.035 (3)	0.019 (3)	0.003 (2)	−0.0029 (17)	−0.004 (2)
Cl1	0.0208 (4)	0.0165 (5)	0.0182 (5)	0.0004 (4)	−0.0004 (3)	−0.0003 (4)
O1	0.0220 (14)	0.0215 (19)	0.046 (2)	0.0039 (12)	−0.0011 (14)	0.0018 (18)
O2	0.0350 (15)	0.0197 (18)	0.0240 (18)	−0.0006 (13)	−0.0028 (13)	0.0059 (15)
O3	0.0232 (14)	0.026 (2)	0.040 (2)	−0.0055 (13)	−0.0023 (13)	0.0019 (17)
O4	0.056 (2)	0.035 (2)	0.0192 (17)	0.0011 (18)	0.0047 (16)	−0.0051 (16)
N3	0.0189 (14)	0.0122 (19)	0.019 (2)	0.0020 (13)	0.0013 (13)	−0.0005 (15)
N4	0.0229 (17)	0.061 (4)	0.028 (2)	0.0016 (19)	0.0012 (16)	0.003 (2)
C8	0.0263 (17)	0.022 (2)	0.016 (2)	−0.0008 (19)	−0.0004 (15)	0.001 (2)
C9	0.0162 (16)	0.016 (2)	0.024 (2)	0.0016 (15)	0.0018 (15)	0.000 (2)
C10	0.0225 (18)	0.027 (3)	0.020 (2)	−0.0014 (17)	0.0054 (16)	−0.001 (2)
C11	0.0272 (19)	0.031 (3)	0.017 (2)	0.0028 (19)	−0.0008 (17)	−0.001 (2)
C12	0.0205 (17)	0.031 (3)	0.025 (3)	−0.0007 (17)	−0.0022 (17)	−0.006 (2)
C13	0.0180 (16)	0.019 (3)	0.027 (3)	−0.0033 (16)	0.0034 (15)	−0.004 (2)
C14	0.0213 (19)	0.033 (3)	0.024 (3)	0.0006 (18)	0.0052 (17)	0.000 (2)
Cl2	0.0207 (4)	0.0245 (6)	0.0188 (5)	−0.0032 (4)	0.0023 (3)	0.0007 (5)
O5	0.0409 (18)	0.032 (2)	0.026 (2)	−0.0075 (16)	−0.0042 (15)	0.0064 (17)
O6	0.0260 (17)	0.092 (4)	0.071 (3)	−0.0020 (19)	0.0140 (17)	0.046 (3)
O7	0.058 (2)	0.030 (2)	0.042 (2)	0.0098 (18)	−0.0241 (18)	−0.011 (2)
O8	0.058 (2)	0.021 (2)	0.043 (2)	0.0024 (17)	0.0123 (18)	−0.0073 (18)

Geometric parameters (Å, º) top

N1—C6	1.338 (5)	N3—C13	1.337 (5)
N1—C2	1.363 (6)	N3—C9	1.363 (5)
N1—C1	1.487 (5)	N3—C8	1.486 (6)
N2—C7	1.135 (6)	N4—C14	1.134 (5)
C1—H1A	0.9800	C8—H8A	0.9800
C1—H1B	0.9800	C8—H8B	0.9800
C1—H1C	0.9800	C8—H8C	0.9800
C2—C3	1.370 (6)	C9—C10	1.368 (6)
C2—C7	1.446 (6)	C9—C14	1.451 (5)
C3—C4	1.392 (6)	C10—C11	1.391 (5)
C3—H3	0.9500	C10—H10	0.9500
C4—C5	1.370 (7)	C11—C12	1.379 (7)
C4—H4	0.9500	C11—H11	0.9500
C5—C6	1.383 (7)	C12—C13	1.370 (7)
C5—H5	0.9500	C12—H12	0.9500
C6—H6	0.9500	C13—H13	0.9500
Cl1—O4	1.430 (3)	Cl2—O6	1.425 (4)
Cl1—O3	1.435 (3)	Cl2—O7	1.431 (4)
Cl1—O1	1.442 (3)	Cl2—O8	1.434 (4)
Cl1—O2	1.444 (3)	Cl2—O5	1.439 (4)

C6—N1—C2	120.0 (4)	C13—N3—C9	119.2 (4)
C6—N1—C1	120.2 (4)	C13—N3—C8	119.9 (4)
C2—N1—C1	119.8 (3)	C9—N3—C8	120.9 (3)
N1—C1—H1A	109.5	N3—C8—H8A	109.5
N1—C1—H1B	109.5	N3—C8—H8B	109.5
H1A—C1—H1B	109.5	H8A—C8—H8B	109.5
N1—C1—H1C	109.5	N3—C8—H8C	109.5
H1A—C1—H1C	109.5	H8A—C8—H8C	109.5
H1B—C1—H1C	109.5	H8B—C8—H8C	109.5
N1—C2—C3	121.2 (4)	N3—C9—C10	121.7 (3)
N1—C2—C7	116.7 (4)	N3—C9—C14	117.0 (4)
C3—C2—C7	122.1 (4)	C10—C9—C14	121.3 (4)
C2—C3—C4	118.8 (4)	C9—C10—C11	119.0 (4)
C2—C3—H3	120.6	C9—C10—H10	120.5
C4—C3—H3	120.6	C11—C10—H10	120.5
C5—C4—C3	119.6 (5)	C12—C11—C10	118.7 (5)
C5—C4—H4	120.2	C12—C11—H11	120.7
C3—C4—H4	120.2	C10—C11—H11	120.7
C4—C5—C6	119.6 (4)	C13—C12—C11	120.0 (4)
C4—C5—H5	120.2	C13—C12—H12	120.0
C6—C5—H5	120.2	C11—C12—H12	120.0
N1—C6—C5	120.8 (4)	N3—C13—C12	121.5 (4)
N1—C6—H6	119.6	N3—C13—H13	119.3
C5—C6—H6	119.6	C12—C13—H13	119.3
N2—C7—C2	178.7 (6)	N4—C14—C9	176.8 (5)
O4—Cl1—O3	109.8 (2)	O6—Cl2—O7	110.1 (3)
O4—Cl1—O1	109.3 (2)	O6—Cl2—O8	110.4 (3)
O3—Cl1—O1	109.2 (2)	O7—Cl2—O8	108.3 (2)
O4—Cl1—O2	110.3 (2)	O6—Cl2—O5	109.5 (2)
O3—Cl1—O2	109.3 (2)	O7—Cl2—O5	108.7 (3)
O1—Cl1—O2	109.0 (2)	O8—Cl2—O5	109.8 (2)

C6—N1—C2—C3	0.0 (7)	C13—N3—C9—C10	−0.3 (7)
C1—N1—C2—C3	−178.3 (5)	C8—N3—C9—C10	−177.4 (5)
C6—N1—C2—C7	178.6 (5)	C13—N3—C9—C14	179.9 (4)
C1—N1—C2—C7	0.3 (7)	C8—N3—C9—C14	2.8 (6)
N1—C2—C3—C4	0.1 (8)	N3—C9—C10—C11	0.4 (8)
C7—C2—C3—C4	−178.5 (5)	C14—C9—C10—C11	−179.8 (5)
C2—C3—C4—C5	0.1 (8)	C9—C10—C11—C12	−1.0 (8)
C3—C4—C5—C6	−0.2 (8)	C10—C11—C12—C13	1.5 (8)
C2—N1—C6—C5	−0.1 (7)	C9—N3—C13—C12	0.8 (7)
C1—N1—C6—C5	178.2 (5)	C8—N3—C13—C12	178.0 (5)
C4—C5—C6—N1	0.3 (8)	C11—C12—C13—N3	−1.4 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1ⁱ	0.98	2.53	3.441 (5)	154
C1—H1C···O3	0.98	2.52	3.164 (5)	123
C3—H3···O5ⁱⁱ	0.95	2.54	3.326 (5)	140
C5—H5···O8ⁱⁱⁱ	0.95	2.66	3.262 (6)	122
C6—H6···O1ⁱ	0.95	2.55	3.415 (6)	152
C6—H6···O4ⁱ	0.95	2.65	3.534 (6)	155
C8—H8A···O1^iv	0.98	2.55	3.294 (6)	132
C8—H8B···O7^v	0.98	2.57	3.538 (6)	169
C8—H8C···O6	0.98	2.51	3.425 (5)	156
C10—H10···O2^vi	0.95	2.51	3.367 (5)	150
C12—H12···O2^vii	0.95	2.52	3.347 (5)	145
C13—H13···O6	0.95	2.35	3.247 (6)	156

Symmetry codes: (i) x−1, y, z; (ii) −x+1, y−1/2, −z+2; (iii) −x, y−1/2, −z+2; (iv) x, y+1, z; (v) x+1, y, z; (vi) −x+2, y+1/2, −z+1; (vii) −x+1, y+1/2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1ⁱ	0.98	2.53	3.441 (5)	154
C1—H1C···O3	0.98	2.52	3.164 (5)	123
C3—H3···O5ⁱⁱ	0.95	2.54	3.326 (5)	140
C5—H5···O8ⁱⁱⁱ	0.95	2.66	3.262 (6)	122
C6—H6···O1ⁱ	0.95	2.55	3.415 (6)	152
C6—H6···O4ⁱ	0.95	2.65	3.534 (6)	155
C8—H8A···O1^iv	0.98	2.55	3.294 (6)	132
C8—H8B···O7^v	0.98	2.57	3.538 (6)	169
C8—H8C···O6	0.98	2.51	3.425 (5)	156
C10—H10···O2^vi	0.95	2.51	3.367 (5)	150
C12—H12···O2^vii	0.95	2.52	3.347 (5)	145
C13—H13···O6	0.95	2.35	3.247 (6)	156

Symmetry codes: (i) x−1, y, z; (ii) −x+1, y−1/2, −z+2; (iii) −x, y−1/2, −z+2; (iv) x, y+1, z; (v) x+1, y, z; (vi) −x+2, y+1/2, −z+1; (vii) −x+1, y+1/2, −z+1.

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

References

Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2014). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconson, USA. Google Scholar
Cui, L.-J. & Chen, X.-Y. (2010). Acta Cryst. E66, o467. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kammer, M. N., Koplitz, L. V. & Mague, J. T. (2013). Acta Cryst. E69, o1281. CSD CrossRef IUCr Journals Google Scholar
Koplitz, L. V., Mague, J. T., Kammer, M. N., McCormick, C. A., Renfro, H. E. & Vumbaco, D. J. (2012). Acta Cryst. E68, o1653. CSD CrossRef IUCr Journals Google Scholar
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008a). CELL_NOW. University of Göttingen, Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2009). TWINABS. University of Göttingen, Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Vaccaro, F. A., Koplitz, L. V. & Mague, J. T. (2015). Acta Cryst. E71, o697–o698. CSD CrossRef IUCr Journals Google Scholar
Zhang, Y. (2009). Acta Cryst. E65, o2373. Web of Science CSD CrossRef IUCr Journals Google Scholar