Ab initio structure determination of nanocrystals of organic pharmaceutical compounds by electron diffraction at room temperature using a Timepix quantum area direct electron detector. Corrigendum

van Genderen, E.; Clabbers, M.T.B.; Das, P.P.; Stewart, A.; Nederlof, I.; Barentsen, K.C.; Portillo, Q.; Pannu, N.S.; Nicolopoulos, S.; Gruene, T.; Abrahams, J.P.

doi:10.1107/S2053273318014079

addenda and errata

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ISSN: 2053-2733

Volume 74| Part 6| November 2018| Page 709

https://doi.org/10.1107/S2053273318014079

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Ab initio structure determination of nanocrystals of organic pharmaceutical compounds by electron diffraction at room temperature using a Timepix quantum area direct electron detector. Corrigendum

E. van Genderen,^a,^b M. T. B. Clabbers,^a,^b P. P. Das,^c A. Stewart,^d I. Nederlof,^a,^e K. C. Barentsen,^a Q. Portillo,^c,^f N. S. Pannu,^a S. Nicolopoulos,^c T. Gruene ^g ^* and J. P. Abrahams ^a,^b,^g ^*

^aBiophysical Structural Chemistry, Leiden University, Einsteinweg 55, 2333 CC Leiden, The Netherlands, ^bCenter for Cellular Imaging and NanoAnalytics (C-CINA), Biozentrum, University of Basel, CH-4058 Basel, Switzerland, ^cNanomegas SPRL, Boulevard Edmond Machtens 79, B 1080, Brussels, Belgium, ^dDepartment of Physics and Energy, Materials and Surface Science Institute (MSSI), University of Limerick, Limerick, Ireland, ^eAmsterdam Scientific Instruments, Postbus 41882, 1009 DB Amsterdam, The Netherlands, ^fCentres Científics i Tecnològics de la Universitat de Barcelona, University of Barcelona, Carrer de Lluís Solé i Sabaris, 1-3, Barcelona, Spain, and ^gBiology and Chemistry, Laboratory of Biomolecular Research, Paul Scherrer Institute (PSI), 5232 Villigen, Switzerland
^*Correspondence e-mail: tim.gruene@psi.ch, jp.abrahams@unibas.ch

(Received 10 August 2018; accepted 10 August 2018; online 30 October 2018)

Corrections are made to Table 1 in the article by van Genderen et al. [Acta Cryst. (2016 ), A72, 236–242].

Keywords: electron nanocrystallography; Timepix quantum area detector; carbamazepine; nicotinic acid; electron diffraction structure determination.

CCDC references: 1438802; 1438803; 1438804; 1438805; 1438806

Supporting information

CCDC references: 1438802; 1438803; 1438804; 1438805; 1438806

Crystal structure: contains datablocks global, carbamazepine_single, carbamazepine_5x-merged, nicotinic_acid_single, nicotinic_acid_2x-merged. DOI: https://doi.org/10.1107/S2053273318014079/td9026sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S2053273318014079/td9026sup2.pdf

Computing details top

For all structures, program(s) used to solve structure: SHELXT 2014/5 (Sheldrick, 2014); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2016).

(carbamazepine_single) top

Crystal data top

C₁₅H₁₂N₂O	Z = 4
M_r = 236.27	F(000) = 201
Monoclinic, P2₁/n	D_x = 1.326 Mg m⁻³
a = 7.578 (12) Å	Monochromatic beam radiation, λ = 0.02508 Å
b = 11.176 (2) Å	µ = 0.000 mm⁻¹
c = 13.991 (13) Å	T = 293 K
β = 93.08 (6)°	Irregular flat disc, unknown
V = 1183 (2) Å³	0.001 × 0.001 × 0.000 mm

Data collection top

Single axis tomography holder diffractometer	1071 independent reflections
Radiation source: tansmission electron microscope	754 reflections with I > 2σ(I)
Detector resolution: 18.1818 pixels mm^-1	R_int = 0.084
rotation method with profile fitting scans	θ_max = 0.9°, θ_min = 0.1°
Absorption correction: empirical (using intensity measurements)	h = −7→7
	k = −13→13
2202 measured reflections	l = −16→16

Refinement top

Refinement on F²	144 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.248	H-atom parameters constrained
wR(F²) = 0.548	w = 1/[σ²(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
S = 2.01	(Δ/σ)_max = 1.591
1071 reflections	Δρ_max = 0.28 e Å⁻³
163 parameters	Δρ_min = −0.28 e Å⁻³

Special details top

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

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

	x	y	z	U_iso*/U_eq
C1	0.342 (4)	0.6883 (10)	0.5012 (13)	0.029 (4)
O1	−0.007 (4)	0.8770 (11)	0.4079 (14)	0.041 (5)
N1	0.213 (3)	0.7341 (10)	0.4376 (12)	0.034 (4)
C2	0.306 (4)	0.6393 (14)	0.5910 (15)	0.044 (6)
H2	0.189457	0.632165	0.608599	0.053*
N2	0.178 (3)	0.9006 (11)	0.5395 (14)	0.035 (6)
H2A	0.129669	0.966585	0.555673	0.042*
H2B	0.265882	0.872039	0.573906	0.042*
C3	0.447 (4)	0.6011 (13)	0.6543 (16)	0.042 (6)
H3	0.424737	0.567220	0.713123	0.050*
C4	0.609 (4)	0.6143 (11)	0.6287 (15)	0.043 (6)
H4	0.700706	0.591288	0.671391	0.052*
C5	0.651 (4)	0.6626 (12)	0.5381 (15)	0.038 (5)
H5	0.768671	0.670354	0.523095	0.045*
C7	0.561 (4)	0.7459 (13)	0.3750 (16)	0.042 (6)
H7	0.662485	0.791906	0.371497	0.051*
C6	0.523 (4)	0.6965 (10)	0.4753 (14)	0.033 (4)
C8	0.469 (4)	0.7310 (11)	0.2965 (16)	0.036 (5)
H8	0.515557	0.763042	0.241906	0.043*
C9	0.306 (4)	0.6719 (11)	0.2834 (14)	0.035 (5)
C10	0.259 (4)	0.6119 (12)	0.1916 (15)	0.046 (6)
H10	0.339450	0.612458	0.143784	0.055*
C11	0.095 (5)	0.5538 (13)	0.1744 (15)	0.049 (6)
H11	0.065789	0.515917	0.116534	0.058*
C12	−0.014 (4)	0.5562 (13)	0.2450 (14)	0.048 (6)
H12	−0.117137	0.512050	0.233599	0.058*
C13	−0.001 (4)	0.6139 (13)	0.3344 (15)	0.043 (6)
H13	−0.090276	0.614416	0.377562	0.052*
C14	0.175 (3)	0.6750 (10)	0.3517 (13)	0.028 (4)
C15	0.117 (4)	0.8414 (11)	0.4599 (15)	0.030 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.061 (10)	0.003 (5)	0.023 (7)	0.007 (6)	0.013 (6)	−0.004 (5)
O1	0.061 (15)	0.023 (6)	0.040 (10)	0.017 (6)	0.011 (9)	−0.016 (6)
N1	0.069 (11)	0.009 (5)	0.025 (7)	0.018 (5)	0.013 (7)	−0.005 (4)
C2	0.073 (17)	0.030 (8)	0.032 (10)	0.000 (9)	0.013 (10)	0.016 (7)
N2	0.054 (17)	0.017 (6)	0.035 (9)	0.016 (6)	0.021 (9)	−0.011 (5)
C3	0.079 (17)	0.019 (7)	0.028 (10)	−0.002 (8)	0.005 (10)	0.002 (7)
C4	0.078 (16)	0.008 (6)	0.044 (10)	0.012 (7)	0.013 (10)	0.004 (6)
C5	0.065 (12)	0.015 (7)	0.035 (9)	0.007 (7)	0.014 (8)	−0.004 (6)
C7	0.075 (16)	0.021 (7)	0.032 (8)	−0.009 (8)	0.022 (8)	0.003 (6)
C6	0.062 (10)	0.002 (5)	0.038 (9)	0.009 (6)	0.021 (8)	0.004 (6)
C8	0.070 (14)	0.011 (6)	0.030 (8)	−0.002 (6)	0.026 (8)	0.003 (6)
C9	0.067 (13)	0.008 (6)	0.032 (8)	0.004 (6)	0.026 (8)	−0.011 (5)
C10	0.091 (17)	0.019 (7)	0.031 (9)	0.008 (7)	0.019 (9)	−0.015 (6)
C11	0.090 (18)	0.025 (7)	0.032 (11)	0.008 (7)	0.018 (10)	−0.024 (7)
C12	0.092 (18)	0.016 (7)	0.039 (10)	0.007 (8)	0.022 (10)	−0.020 (6)
C13	0.065 (14)	0.029 (7)	0.038 (9)	0.005 (7)	0.027 (9)	−0.024 (7)
C14	0.063 (13)	0.005 (5)	0.018 (7)	0.015 (5)	0.018 (6)	0.004 (4)
C15	0.050 (14)	0.003 (5)	0.038 (10)	0.004 (5)	0.021 (9)	−0.005 (5)

Geometric parameters (Å, º) top

C1—N1	1.39 (3)	C5—H5	0.9300
C1—C2	1.41 (2)	C7—C8	1.28 (4)
C1—C6	1.44 (3)	C7—C6	1.55 (2)
O1—C15	1.22 (4)	C7—H7	0.9300
N1—C14	1.39 (3)	C8—C9	1.40 (4)
N1—C15	1.45 (2)	C8—H8	0.9300
C2—C3	1.42 (4)	C9—C14	1.41 (2)
C2—H2	0.9300	C9—C10	1.48 (3)
N2—C15	1.36 (3)	C10—C11	1.41 (5)
N2—H2A	0.8600	C10—H10	0.9300
N2—H2B	0.8600	C11—C12	1.32 (3)
C3—C4	1.30 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.41 (3)
C4—C5	1.43 (2)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.51 (4)
C5—C6	1.33 (4)	C13—H13	0.9300

N1—C1—C2	123 (2)	C1—C6—C7	118 (2)
N1—C1—C6	117.7 (16)	C7—C8—C9	127.4 (17)
C2—C1—C6	119 (2)	C7—C8—H8	116.3
C1—N1—C14	119.0 (13)	C9—C8—H8	116.3
C1—N1—C15	121.0 (18)	C8—C9—C14	123.0 (19)
C14—N1—C15	120 (2)	C8—C9—C10	119.9 (18)
C1—C2—C3	120 (3)	C14—C9—C10	117 (2)
C1—C2—H2	120.2	C11—C10—C9	121.9 (19)
C3—C2—H2	120.2	C11—C10—H10	119.0
C15—N2—H2A	120.0	C9—C10—H10	119.0
C15—N2—H2B	120.0	C12—C11—C10	116 (2)
H2A—N2—H2B	120.0	C12—C11—H11	121.8
C4—C3—C2	119 (2)	C10—C11—H11	121.8
C4—C3—H3	120.5	C11—C12—C13	131 (3)
C2—C3—H3	120.5	C11—C12—H12	114.5
C3—C4—C5	123 (3)	C13—C12—H12	114.5
C3—C4—H4	118.5	C12—C13—C14	111.7 (18)
C5—C4—H4	118.5	C12—C13—H13	124.2
C6—C5—C4	120 (3)	C14—C13—H13	124.2
C6—C5—H5	120.0	N1—C14—C9	119 (2)
C4—C5—H5	120.0	N1—C14—C13	119.5 (15)
C8—C7—C6	128 (2)	C9—C14—C13	121.9 (18)
C8—C7—H7	116.1	O1—C15—N2	123.3 (15)
C6—C7—H7	116.1	O1—C15—N1	121 (2)
C5—C6—C1	119.2 (17)	N2—C15—N1	115 (2)
C5—C6—C7	122 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.86	2.06	2.915 (18)	178

Symmetry code: (i) −x, −y+2, −z+1.

(carbamazepine_5x-merged) top

Crystal data top

C₁₅H₁₂N₂O	Z = 4
M_r = 236.27	F(000) = 201
Monoclinic, P2₁/n	D_x = 1.327 Mg m⁻³
a = 7.576 (12) Å	Monochromatic beam radiation, λ = 0.02508 Å
b = 11.188 (2) Å	µ = 0.000 mm⁻¹
c = 13.967 (13) Å	T = 293 K
β = 87.03 (6)°	Not applicable, data merged from 5 xtals, unknown
V = 1182 (2) Å³

Data collection top

Single axis tomography holder diffractometer	1880 independent reflections
Radiation source: tansmission electron microscope	1157 reflections with I > 2σ(I)
Detector resolution: 18.1818 pixels mm^-1	R_int = 0.448
rotation method with profile fitting scans	θ_max = 0.9°, θ_min = 0.1°
Absorption correction: empirical (using intensity measurements)	h = −9→9
	k = 0→13
6780 measured reflections	l = 0→15

Refinement top

Refinement on F²	144 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.396	H-atom parameters constrained
wR(F²) = 0.699	w = 1/[σ²(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
S = 2.44	(Δ/σ)_max = 0.874
1880 reflections	Δρ_max = 0.36 e Å⁻³
163 parameters	Δρ_min = −0.41 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
C1	0.349 (2)	0.6897 (13)	0.4992 (13)	0.022 (3)
N1	0.207 (2)	0.7358 (10)	0.5597 (12)	0.022 (3)
O1	−0.009 (2)	0.8762 (12)	0.5913 (12)	0.034 (4)
N2	0.179 (3)	0.9013 (13)	0.4585 (14)	0.045 (6)
H2A	0.126962	0.965549	0.441031	0.053*
H2B	0.268123	0.873984	0.424903	0.053*
C2	0.305 (3)	0.6408 (16)	0.4092 (15)	0.037 (4)
H2	0.188721	0.634499	0.392024	0.044*
C3	0.446 (3)	0.6025 (18)	0.3478 (18)	0.046 (5)
H3	0.422124	0.566799	0.289784	0.055*
C4	0.616 (3)	0.6161 (13)	0.3704 (15)	0.033 (4)
H4	0.708500	0.597996	0.326221	0.040*
C5	0.651 (3)	0.6586 (17)	0.4630 (16)	0.040 (5)
H5	0.766129	0.657955	0.482393	0.048*
C6	0.520 (2)	0.7005 (14)	0.5245 (14)	0.025 (3)
C7	0.573 (2)	0.7410 (14)	0.6169 (14)	0.029 (4)
H7	0.682472	0.778779	0.618833	0.035*
C8	0.475 (2)	0.7281 (15)	0.7029 (15)	0.025 (4)
H8	0.527554	0.756611	0.757124	0.030*
C9	0.300 (2)	0.6755 (15)	0.7189 (14)	0.024 (3)
C10	0.258 (3)	0.6148 (14)	0.8050 (15)	0.031 (4)
H10	0.341591	0.616130	0.851673	0.037*
C11	0.108 (3)	0.5553 (16)	0.8249 (14)	0.034 (4)
H11	0.086172	0.514661	0.882388	0.040*
C12	−0.012 (3)	0.5583 (17)	0.7542 (14)	0.035 (4)
H12	−0.118058	0.517882	0.767124	0.042*
C13	0.007 (2)	0.6136 (14)	0.6682 (13)	0.021 (4)
H13	−0.081621	0.612753	0.624281	0.025*
C14	0.175 (2)	0.6747 (13)	0.6492 (13)	0.020 (3)
C15	0.116 (2)	0.8397 (12)	0.5432 (13)	0.024 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.020 (6)	0.014 (7)	0.031 (8)	0.010 (5)	0.012 (5)	0.006 (5)
N1	0.023 (6)	0.001 (5)	0.040 (7)	0.003 (4)	0.016 (5)	0.006 (4)
O1	0.031 (8)	0.029 (7)	0.041 (10)	0.021 (5)	0.028 (7)	0.013 (5)
N2	0.054 (12)	0.015 (7)	0.059 (12)	0.021 (7)	0.048 (9)	0.021 (6)
C2	0.034 (9)	0.042 (11)	0.032 (9)	0.007 (7)	0.013 (7)	−0.001 (6)
C3	0.046 (9)	0.046 (11)	0.043 (12)	0.002 (7)	0.025 (7)	−0.010 (8)
C4	0.042 (8)	0.012 (8)	0.042 (9)	0.011 (6)	0.029 (8)	0.008 (6)
C5	0.032 (8)	0.044 (11)	0.040 (10)	0.015 (7)	0.030 (7)	0.002 (7)
C6	0.020 (6)	0.023 (8)	0.031 (8)	0.017 (5)	0.013 (5)	0.005 (5)
C7	0.020 (8)	0.034 (9)	0.030 (8)	0.006 (6)	0.014 (5)	0.008 (5)
C8	0.004 (6)	0.040 (9)	0.029 (8)	0.003 (5)	0.007 (6)	−0.001 (6)
C9	0.010 (6)	0.033 (8)	0.029 (8)	0.003 (5)	0.008 (5)	0.002 (6)
C10	0.034 (9)	0.024 (8)	0.032 (9)	0.007 (6)	0.011 (6)	0.005 (6)
C11	0.039 (9)	0.045 (10)	0.016 (10)	−0.001 (7)	0.014 (7)	0.008 (7)
C12	0.031 (9)	0.058 (11)	0.013 (9)	0.000 (7)	0.021 (6)	0.003 (6)
C13	0.010 (7)	0.041 (9)	0.010 (9)	−0.008 (6)	0.010 (6)	0.000 (6)
C14	0.005 (6)	0.018 (7)	0.036 (8)	−0.001 (5)	0.007 (5)	0.010 (5)
C15	0.029 (8)	0.000 (6)	0.040 (10)	0.005 (5)	0.027 (7)	0.007 (5)

Geometric parameters (Å, º) top

C1—C6	1.37 (2)	C5—H5	0.9300
C1—N1	1.43 (2)	C6—C7	1.44 (3)
C1—C2	1.43 (3)	C7—C8	1.39 (3)
N1—C15	1.379 (19)	C7—H7	0.9300
N1—C14	1.43 (2)	C8—C9	1.46 (2)
O1—C15	1.20 (2)	C8—H8	0.9300
N2—C15	1.43 (2)	C9—C14	1.39 (3)
N2—H2A	0.8600	C9—C10	1.40 (3)
N2—H2B	0.8600	C10—C11	1.34 (3)
C2—C3	1.40 (3)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.38 (3)
C3—C4	1.35 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.35 (3)
C4—C5	1.41 (3)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.46 (2)
C5—C6	1.36 (2)	C13—H13	0.9300

C6—C1—N1	120.6 (16)	C6—C7—H7	117.3
C6—C1—C2	121.9 (17)	C7—C8—C9	128.1 (18)
N1—C1—C2	117.2 (17)	C7—C8—H8	115.9
C15—N1—C1	125.1 (13)	C9—C8—H8	115.9
C15—N1—C14	119.0 (13)	C14—C9—C10	117.7 (17)
C1—N1—C14	115.5 (12)	C14—C9—C8	122.8 (16)
C15—N2—H2A	120.0	C10—C9—C8	119.3 (17)
C15—N2—H2B	120.0	C11—C10—C9	125 (2)
H2A—N2—H2B	120.0	C11—C10—H10	117.6
C3—C2—C1	117 (2)	C9—C10—H10	117.6
C3—C2—H2	121.6	C10—C11—C12	115.3 (19)
C1—C2—H2	121.6	C10—C11—H11	122.4
C4—C3—C2	122 (2)	C12—C11—H11	122.4
C4—C3—H3	119.1	C13—C12—C11	127 (2)
C2—C3—H3	119.1	C13—C12—H12	116.4
C3—C4—C5	118.3 (19)	C11—C12—H12	116.4
C3—C4—H4	120.9	C12—C13—C14	115.2 (18)
C5—C4—H4	120.9	C12—C13—H13	122.4
C6—C5—C4	122 (2)	C14—C13—H13	122.4
C6—C5—H5	118.9	C9—C14—N1	121.1 (15)
C4—C5—H5	118.9	C9—C14—C13	119.7 (16)
C5—C6—C1	118.3 (19)	N1—C14—C13	119.1 (15)
C5—C6—C7	116.4 (18)	O1—C15—N1	125.5 (14)
C1—C6—C7	124.9 (16)	O1—C15—N2	121.2 (14)
C8—C7—C6	125.3 (18)	N1—C15—N2	113.3 (14)
C8—C7—H7	117.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.86	2.04	2.90 (2)	176

Symmetry code: (i) −x, −y+2, −z+1.

(nicotinic_acid_single) top

Crystal data top

C₆H₅NO₂	Z = 4
M_r = 123.11	F(000) = 95
Monoclinic, P2₁/c	D_x = 1.426 Mg m⁻³
a = 7.303 (11) Å	Monochromatic beam radiation, λ = 0.02508 Å
b = 11.693 (2) Å	µ = 0.000 mm⁻¹
c = 7.33 (3) Å	T = 293 K
β = 113.68 (14)°	Flat rectangular, with irregular borders, unknown
V = 573 (2) Å³	0.002 × 0.001 × 0.000 mm

Data collection top

Single axis tomography holder diffractometer	503 independent reflections
Radiation source: tansmission electron microscope	302 reflections with I > 2σ(I)
Detector resolution: 18.1818 pixels mm^-1	R_int = 0.071
rotation method with profile fitting scans	θ_max = 1.0°, θ_min = 0.1°
Absorption correction: empirical (using intensity measurements)	h = −5→5
	k = −15→15
953 measured reflections	l = −8→8

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.294	H-atom parameters constrained
wR(F²) = 0.611	w = 1/[σ²(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
S = 2.13	(Δ/σ)_max < 0.001
503 reflections	Δρ_max = 0.19 e Å⁻³
38 parameters	Δρ_min = −0.24 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
N1	0.751 (4)	0.8887 (9)	0.7043 (18)	0.030 (3)*
C1	0.842 (4)	0.7918 (9)	0.7152 (19)	0.032 (4)*
H1	0.977539	0.795918	0.742835	0.038*
O1	0.801 (5)	0.4845 (12)	0.693 (2)	0.054 (4)*
C2	0.759 (5)	0.6823 (10)	0.690 (2)	0.032 (4)*
O2	1.068 (4)	0.5888 (10)	0.743 (2)	0.044 (4)*
H2	1.126657	0.527502	0.777526	0.065*
C3	0.539 (5)	0.6779 (11)	0.652 (2)	0.031 (4)*
H3	0.471218	0.609220	0.639807	0.037*
C4	0.452 (6)	0.7759 (13)	0.636 (3)	0.053 (5)*
H4	0.316186	0.778021	0.606882	0.064*
C5	0.558 (5)	0.8794 (12)	0.663 (2)	0.039 (4)*
H5	0.486131	0.946780	0.650925	0.047*
C6	0.874 (5)	0.5751 (10)	0.7066 (19)	0.026 (3)*

Geometric parameters (Å, º) top

N1—C1	1.30 (3)	O2—C6	1.34 (4)
N1—C5	1.32 (5)	O2—H2	0.8200
C1—C2	1.39 (2)	C3—C4	1.29 (3)
C1—H1	0.9300	C3—H3	0.9300
O1—C6	1.17 (3)	C4—C5	1.40 (3)
C2—C6	1.49 (3)	C4—H4	0.9300
C2—C3	1.52 (5)	C5—H5	0.9300

C1—N1—C5	114.5 (16)	C2—C3—H3	122.2
N1—C1—C2	128 (3)	C3—C4—C5	122 (3)
N1—C1—H1	116.2	C3—C4—H4	119.0
C2—C1—H1	116.2	C5—C4—H4	119.0
C1—C2—C6	124 (3)	N1—C5—C4	125 (2)
C1—C2—C3	115.1 (19)	N1—C5—H5	117.4
C6—C2—C3	120.5 (15)	C4—C5—H5	117.4
C6—O2—H2	109.5	O1—C6—O2	122 (2)
C4—C3—C2	116 (2)	O1—C6—C2	122 (3)
C4—C3—H3	122.2	O2—C6—C2	115.5 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1ⁱ	0.82	1.83	2.64 (2)	167

Symmetry code: (i) −x+2, y−1/2, −z+3/2.

(nicotinic_acid_2x-merged) top

Crystal data top

C₆H₅NO₂	Z = 4
M_r = 123.11	F(000) = 95
Monoclinic, P2₁/c	D_x = 1.406 Mg m⁻³
a = 7.41 (3) Å	Monochromatic beam radiation, λ = 0.02508 Å
b = 11.692 (2) Å	µ = 0.000 mm⁻¹
c = 7.377 (11) Å	T = 293 K
β = 114.45 (14)°	N/a, data merged from 2 crystals, n/a, data merged from 2 crystals
V = 581 (2) Å³

Data collection top

Single axis tomography holder diffractometer	552 independent reflections
Radiation source: tansmission electron microscope	303 reflections with I > 2σ(I)
Detector resolution: 18.1818 pixels mm^-1	R_int = 0.270
rotation method with profile fitting scans	θ_max = 1.0°, θ_min = 0.1°
Absorption correction: empirical (using intensity measurements)	h = 0→5
	k = −15→0
1337 measured reflections	l = −8→8

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.321	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.648	w = 1/[σ²(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
S = 2.08	(Δ/σ)_max < 0.001
552 reflections	Δρ_max = 0.22 e Å⁻³
39 parameters	Δρ_min = −0.31 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq
C6	0.633 (4)	0.5757 (10)	0.2902 (18)	0.020 (3)*
C1	0.661 (4)	0.7921 (10)	0.2828 (18)	0.025 (4)*
H1	0.528724	0.795951	0.261756	0.031*
O1	0.435 (5)	0.5882 (11)	0.253 (2)	0.039 (4)*
HO	0.379022	0.526141	0.221678	0.026 (15)*
N1	0.761 (4)	0.8903 (10)	0.2927 (19)	0.029 (4)*
O2	0.699 (6)	0.4865 (15)	0.305 (3)	0.059 (5)*
C2	0.753 (5)	0.6830 (11)	0.303 (2)	0.030 (4)*
C5	0.958 (5)	0.8780 (13)	0.331 (2)	0.034 (4)*
H5	1.035013	0.940481	0.329449	0.040*
C4	1.031 (6)	0.7765 (14)	0.368 (3)	0.046 (5)*
H2	1.169154	0.777592	0.427338	0.056*
C3	0.965 (5)	0.6777 (12)	0.346 (2)	0.029 (4)*
H3	1.037913	0.611383	0.355341	0.034*

Geometric parameters (Å, º) top

C6—O2	1.14 (3)	N1—C5	1.38 (5)
C6—O1	1.38 (4)	C2—C3	1.47 (5)
C6—C2	1.52 (3)	C5—C4	1.29 (3)
C1—N1	1.35 (3)	C5—H5	0.9300
C1—C2	1.42 (3)	C4—C3	1.24 (3)
C1—H1	0.9300	C4—H2	0.9300
O1—HO	0.8200	C3—H3	0.9300

O2—C6—O1	120 (2)	C3—C2—C6	121.6 (15)
O2—C6—C2	122 (3)	C4—C5—N1	117 (3)
O1—C6—C2	117.9 (16)	C4—C5—H5	121.4
N1—C1—C2	122 (3)	N1—C5—H5	121.4
N1—C1—H1	118.9	C3—C4—C5	136 (4)
C2—C1—H1	118.9	C3—C4—H2	111.8
C6—O1—HO	109.5	C5—C4—H2	111.8
C1—N1—C5	115.6 (17)	C4—C3—C2	108 (3)
C1—C2—C3	119 (2)	C4—C3—H3	125.8
C1—C2—C6	120 (3)	C2—C3—H3	125.8

Acknowledgements

The authors are grateful to Professor Ton Spek, Utrecht University, The Netherlands, for alerting them to this error.

References

Genderen, E. van, Clabbers, M. T. B., Das, P. P., Stewart, A., Nederlof, I., Barentsen, K. C., Portillo, Q., Pannu, N. S., Nicolopoulos, S., Gruene, T. & Abrahams, J. P. (2016). Acta Cryst. A72, 236–242. Web of Science CSD CrossRef IUCr Journals Google Scholar
Luebben, J. & Gruene, T. (2015). Proc. Natl Acad. Sci. USA, 112, 8999–9003. Web of Science CrossRef CAS PubMed Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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Volume 74| Part 6| November 2018| Page 709

https://doi.org/10.1107/S2053273318014079

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addenda and errata\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ab initio structure determination of nanocrystals of organic pharmaceutical compounds by electron diffraction at room temperature using a Timepix quantum area direct electron detector. Corrigendum

Supporting information

Acknowledgements

References

addenda and errata