Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520615019538/bi5051sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520615019538/bi5051dihydrate_mono_NEUTRONsup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520615019538/bi5051dihydrate_mono_XRAYsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520615019538/bi5051dihydrate_ortho_NEUTRONsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520615019538/bi5051dihydrate_ortho_XRAYsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520615019538/bi5051formIII_NEUTRONsup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520615019538/bi5051formIII_XRAY_shelxsup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520615019538/bi5051formIII_XRAY_xdsup8.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520615019538/bi5051sup9.pdf |
CCDC references: 1027345; 1027346; 1027347; 1027348; 1027349; 1027350; 1027351
Data collection: SXD2001, Gutmann (2005) for dihydrate_mono_NEUTRON, dihydrate_ortho_NEUTRON, formIII_NEUTRON; Bruker APEX2 software for dihydrate_mono_XRAY, dihydrate_ortho_XRAY, formIII_XRAY_shelx, formIII_XRAY_xd. Cell refinement: SXD2001, Gutmann (2005) for dihydrate_mono_NEUTRON, dihydrate_ortho_NEUTRON, formIII_NEUTRON; SAINT V8.27B integration software for dihydrate_mono_XRAY, dihydrate_ortho_XRAY; SAINT V7.68A integration software for formIII_XRAY_shelx, formIII_XRAY_xd. Data reduction: SXD2001, Gutmann (2005) for dihydrate_mono_NEUTRON, dihydrate_ortho_NEUTRON, formIII_NEUTRON; SORTAV (Blessing, 1995) for dihydrate_mono_XRAY, dihydrate_ortho_XRAY, formIII_XRAY_shelx, formIII_XRAY_xd. For all compounds, program(s) used to solve structure: SIR92 (Altomare et al., 1994). Program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013) for dihydrate_mono_NEUTRON, dihydrate_mono_XRAY, dihydrate_ortho_NEUTRON, dihydrate_ortho_XRAY, formIII_NEUTRON, formIII_XRAY_shelx; Volkov et al., (2006) for formIII_XRAY_xd. Molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) for dihydrate_mono_NEUTRON, dihydrate_mono_XRAY, dihydrate_ortho_NEUTRON, dihydrate_ortho_XRAY, formIII_NEUTRON, formIII_XRAY_shelx; Volkov et al., (2006) for formIII_XRAY_xd. Software used to prepare material for publication: WinGX publication routines (Farrugia, 2012) for dihydrate_mono_NEUTRON, dihydrate_mono_XRAY, dihydrate_ortho_NEUTRON, dihydrate_ortho_XRAY, formIII_NEUTRON, formIII_XRAY_shelx; Volkov et al., (2006) for formIII_XRAY_xd.
C15H12N2O·2(H2O) | F(000) = 576 |
Mr = 272.3 | Dx = 1.319 Mg m−3 |
Monoclinic, P21/c | Neutrons radiation, λ = 0.42 Å |
Hall symbol: -P 2ybc | Cell parameters from 0 reflections |
a = 10.116 (3) Å | θ = 0–0° |
b = 28.856 (8) Å | µ = 0 mm−1 |
c = 4.8378 (16) Å | T = 100 K |
β = 103.908 (18)° | Prism, colourless |
V = 1370.7 (7) Å3 | 5 × 2 × 2 mm |
Z = 4 |
SXD beamline diffractometer | 5423 reflections with I > 2σ(I) |
Radiation source: ISIS neutron spallation source | θmax = 83.9°, θmin = 7.9° |
time of flight Laue diffraction scans | h = −27→23 |
5423 measured reflections | k = −111→56 |
5423 independent reflections | l = −9→5 |
Refinement on F2 | Secondary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.065 | All H-atom parameters refined |
wR(F2) = 0.172 | w = 1/[σ2(Fo2) + (0.1101P)2 + 28.884P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
5423 reflections | Δρmax = 1.46 e Å−3 |
365 parameters | Δρmin = −1.34 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 constraints | Extinction coefficient: 0.00099 (8) |
Primary atom site location: structure-invariant direct methods |
C15H12N2O·2(H2O) | V = 1370.7 (7) Å3 |
Mr = 272.3 | Z = 4 |
Monoclinic, P21/c | Neutrons radiation, λ = 0.42 Å |
a = 10.116 (3) Å | µ = 0 mm−1 |
b = 28.856 (8) Å | T = 100 K |
c = 4.8378 (16) Å | 5 × 2 × 2 mm |
β = 103.908 (18)° |
SXD beamline diffractometer | 5423 independent reflections |
5423 measured reflections | 5423 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.065 | 0 restraints |
wR(F2) = 0.172 | All H-atom parameters refined |
S = 1.10 | w = 1/[σ2(Fo2) + (0.1101P)2 + 28.884P] where P = (Fo2 + 2Fc2)/3 |
5423 reflections | Δρmax = 1.46 e Å−3 |
365 parameters | Δρmin = −1.34 e Å−3 |
Experimental. For peak integration a local UB matrix refined for each frame, using approximately 30 reflections from each of the 11 detectors. Hence _cell_measurement_reflns_used 330 For final cell dimensions a weighted average of all local cells was calculated. Because of the nature of the experiment, it is not possible to give values of theta_min and theta_max for the cell determination. The same applies for the wavelength used for the experiment. The range of wavelengths used was 0.42–7.97 Angstroms, BUT the bulk of the diffraction information is obtained from wavelengths in the range 0.7–2.5 Angstroms. The data collection procedures on the SXD instrument used for the single-crystal neutron data collection are most recently summarized in following paper: Keen, D. A.; Gutmann, M. J.; Wilson, C·C. (2006). J. Appl. Cryst. 39,714. |
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. The variable wavelength nature of the data collection procedure means that sensible values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max cannot be given. Instead, the following limits are given: _diffrn_reflns_sin(theta)/lambda_min 0.034 _diffrn_reflns_sin(theta)/lambda_max 2.268 _refine_diff_density_max/min is given in Fermi per Angstrom cubed not electrons per angstrom cubed. Another way to consider the _refine_diff_density_ is as a percentage of the scattering density of a given atom: _refine_diff_density_max = 4% of C atom _refine_diff_density_min = −3.8% of C atom |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.3839 (9) | 0.0478 (4) | 0.512 (3) | 0.008 (2)* | 0.499 (13) |
N1 | 0.6161 (7) | 0.0476 (3) | 0.642 (2) | 0.0111 (17)* | 0.499 (13) |
N1A | 0.3850 (6) | 0.0459 (2) | 0.567 (2) | 0.0103 (16)* | 0.501 (13) |
O1A | 0.6155 (10) | 0.0452 (4) | 0.692 (3) | 0.008 (2)* | 0.501 (13) |
N2 | 0.4999 (2) | 0.11070 (6) | 0.7688 (7) | 0.0116 (6) | |
C1 | 0.5002 (3) | 0.06669 (9) | 0.6577 (10) | 0.0115 (8) | |
C2 | 0.3758 (3) | 0.13426 (9) | 0.7720 (9) | 0.0108 (8) | |
C3 | 0.2902 (3) | 0.11659 (10) | 0.9343 (10) | 0.0127 (8) | |
C4 | 0.1684 (3) | 0.13903 (10) | 0.9355 (10) | 0.0144 (8) | |
C5 | 0.1325 (3) | 0.17927 (11) | 0.7734 (10) | 0.0135 (8) | |
C6 | 0.2185 (3) | 0.19686 (10) | 0.6139 (10) | 0.0128 (8) | |
C7 | 0.3427 (3) | 0.17510 (10) | 0.6111 (9) | 0.0106 (8) | |
C8 | 0.4314 (3) | 0.19592 (10) | 0.4464 (10) | 0.0120 (8) | |
C9 | 0.5689 (3) | 0.19592 (10) | 0.5138 (10) | 0.0118 (8) | |
C10 | 0.6573 (3) | 0.17511 (10) | 0.7703 (9) | 0.0103 (7) | |
C11 | 0.7817 (3) | 0.19683 (10) | 0.8949 (10) | 0.0123 (8) | |
C12 | 0.8677 (3) | 0.17926 (11) | 1.1422 (10) | 0.0135 (8) | |
C13 | 0.8315 (3) | 0.13889 (11) | 1.2674 (10) | 0.0141 (8) | |
C14 | 0.7098 (3) | 0.11667 (10) | 1.1446 (10) | 0.0130 (8) | |
C15 | 0.6238 (3) | 0.13426 (9) | 0.8958 (9) | 0.0096 (8) | |
H3 | 0.3207 (8) | 0.0855 (2) | 1.060 (2) | 0.030 (2) | |
H4 | 0.1030 (7) | 0.1250 (3) | 1.063 (2) | 0.031 (2) | |
H5 | 0.0364 (7) | 0.1966 (3) | 0.774 (2) | 0.032 (2) | |
H6 | 0.1911 (7) | 0.2284 (2) | 0.489 (2) | 0.029 (2) | |
H8 | 0.3798 (7) | 0.2162 (3) | 0.261 (2) | 0.0275 (19) | |
H9 | 0.6202 (7) | 0.2161 (3) | 0.380 (2) | 0.028 (2) | |
H11 | 0.8089 (7) | 0.2283 (2) | 0.800 (2) | 0.029 (2) | |
H12 | 0.9631 (6) | 0.1965 (3) | 1.236 (2) | 0.030 (2) | |
H13 | 0.8978 (7) | 0.1251 (3) | 1.459 (2) | 0.029 (2) | |
H14 | 0.6796 (7) | 0.0853 (2) | 1.241 (2) | 0.032 (2) | |
H1A | 0.7070 (12) | 0.0614 (5) | 0.743 (5) | 0.031 (5) | 0.499 (13) |
H1B | 0.6136 (13) | 0.0129 (5) | 0.582 (4) | 0.024 (4) | 0.499 (13) |
H1C | 0.2946 (12) | 0.0608 (5) | 0.539 (5) | 0.031 (5) | 0.501 (13) |
H1D | 0.3874 (13) | 0.0132 (5) | 0.469 (4) | 0.025 (4) | 0.501 (13) |
O2 | 0.0847 (6) | 0.04801 (17) | 0.3483 (16) | 0.0294 (14) | |
H2A | 0.0336 (11) | 0.0526 (3) | 0.493 (3) | 0.042 (3) | |
H2B | 0.1945 (14) | 0.0529 (6) | 0.447 (5) | 0.033 (5) | 0.499 (13) |
H2C | 0.0792 (14) | 0.0162 (5) | 0.314 (5) | 0.028 (4) | 0.501 (13) |
O3 | 0.9173 (6) | 0.04807 (17) | 0.7636 (17) | 0.0291 (13) | |
H3A | 0.9693 (14) | 0.0527 (4) | 0.959 (3) | 0.051 (3) | |
H3B | 0.9173 (15) | 0.0158 (5) | 0.726 (5) | 0.031 (5) | 0.499 (13) |
H3C | 0.8077 (17) | 0.0536 (6) | 0.754 (5) | 0.035 (5) | 0.501 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N2 | 0.0105 (6) | 0.0052 (7) | 0.0190 (18) | −0.0002 (6) | 0.0035 (8) | −0.0014 (9) |
C1 | 0.0116 (9) | 0.0056 (9) | 0.018 (3) | −0.0005 (8) | 0.0038 (12) | −0.0009 (12) |
C2 | 0.0104 (10) | 0.0053 (10) | 0.017 (2) | 0.0000 (8) | 0.0050 (11) | 0.0004 (13) |
C3 | 0.0143 (11) | 0.0086 (11) | 0.017 (3) | −0.0008 (8) | 0.0064 (13) | 0.0006 (14) |
C4 | 0.0123 (10) | 0.0128 (12) | 0.020 (3) | −0.0015 (9) | 0.0072 (12) | −0.0005 (15) |
C5 | 0.0104 (10) | 0.0137 (12) | 0.018 (3) | 0.0009 (8) | 0.0053 (12) | −0.0007 (14) |
C6 | 0.0096 (10) | 0.0100 (11) | 0.019 (3) | 0.0021 (8) | 0.0040 (12) | 0.0028 (14) |
C7 | 0.0092 (10) | 0.0076 (10) | 0.015 (2) | 0.0005 (8) | 0.0038 (11) | 0.0007 (12) |
C8 | 0.0090 (9) | 0.0103 (11) | 0.016 (3) | 0.0007 (8) | 0.0024 (12) | 0.0018 (14) |
C9 | 0.0105 (10) | 0.0094 (11) | 0.016 (3) | 0.0007 (8) | 0.0036 (12) | 0.0003 (14) |
C10 | 0.0105 (10) | 0.0077 (10) | 0.014 (2) | −0.0009 (8) | 0.0045 (11) | 0.0006 (12) |
C11 | 0.0090 (10) | 0.0111 (11) | 0.017 (3) | −0.0014 (8) | 0.0040 (12) | 0.0010 (14) |
C12 | 0.0092 (10) | 0.0128 (12) | 0.017 (3) | −0.0009 (8) | 0.0006 (12) | −0.0012 (14) |
C13 | 0.0141 (11) | 0.0114 (12) | 0.016 (3) | 0.0013 (9) | 0.0013 (12) | −0.0013 (14) |
C14 | 0.0135 (11) | 0.0086 (11) | 0.016 (3) | 0.0008 (8) | 0.0014 (12) | 0.0016 (13) |
C15 | 0.0095 (9) | 0.0059 (10) | 0.013 (3) | 0.0001 (7) | 0.0021 (11) | −0.0007 (12) |
H3 | 0.034 (3) | 0.019 (3) | 0.038 (7) | 0.002 (2) | 0.011 (4) | 0.010 (4) |
H4 | 0.030 (3) | 0.031 (3) | 0.038 (7) | −0.003 (3) | 0.020 (4) | 0.001 (4) |
H5 | 0.020 (3) | 0.030 (3) | 0.048 (7) | 0.006 (2) | 0.012 (3) | 0.003 (4) |
H6 | 0.022 (3) | 0.021 (3) | 0.041 (7) | 0.006 (2) | 0.005 (3) | 0.007 (3) |
H8 | 0.024 (3) | 0.031 (3) | 0.023 (6) | 0.004 (2) | −0.002 (3) | 0.013 (4) |
H9 | 0.024 (3) | 0.032 (3) | 0.030 (6) | −0.002 (2) | 0.010 (3) | 0.013 (4) |
H11 | 0.026 (3) | 0.020 (3) | 0.040 (7) | −0.007 (2) | 0.008 (3) | 0.010 (3) |
H12 | 0.019 (3) | 0.033 (4) | 0.035 (7) | −0.007 (2) | −0.001 (3) | −0.001 (4) |
H13 | 0.030 (3) | 0.032 (4) | 0.018 (6) | 0.004 (3) | −0.005 (3) | 0.005 (4) |
H14 | 0.032 (3) | 0.017 (3) | 0.042 (8) | −0.006 (2) | 0.000 (4) | 0.007 (4) |
H1A | 0.014 (5) | 0.026 (7) | 0.048 (15) | −0.003 (4) | 0.002 (6) | −0.012 (8) |
H1B | 0.022 (5) | 0.017 (6) | 0.033 (13) | 0.002 (4) | 0.007 (6) | 0.002 (6) |
H1C | 0.019 (5) | 0.016 (6) | 0.055 (16) | 0.001 (4) | 0.005 (6) | −0.007 (7) |
H1D | 0.025 (5) | 0.010 (5) | 0.039 (13) | 0.003 (4) | 0.007 (6) | 0.000 (6) |
O2 | 0.048 (3) | 0.0182 (19) | 0.026 (5) | −0.0051 (18) | 0.017 (3) | −0.003 (2) |
H2A | 0.064 (6) | 0.032 (4) | 0.035 (9) | 0.002 (4) | 0.023 (6) | −0.005 (5) |
H2B | 0.025 (6) | 0.025 (7) | 0.045 (15) | −0.002 (4) | −0.001 (7) | −0.004 (8) |
H2C | 0.027 (6) | 0.016 (6) | 0.037 (14) | −0.003 (4) | 0.003 (7) | 0.001 (7) |
O3 | 0.055 (3) | 0.0158 (19) | 0.015 (4) | 0.0077 (19) | 0.005 (3) | −0.002 (2) |
H3A | 0.091 (9) | 0.035 (5) | 0.023 (10) | −0.005 (5) | 0.006 (7) | −0.001 (6) |
H3B | 0.031 (6) | 0.021 (7) | 0.040 (15) | −0.006 (5) | 0.006 (7) | −0.007 (8) |
H3C | 0.040 (8) | 0.027 (7) | 0.039 (16) | 0.002 (6) | 0.011 (8) | −0.005 (8) |
O1—C1 | 1.334 (11) | C7—C8 | 1.464 (5) |
N1—H1A | 1.014 (15) | C8—H8 | 1.091 (10) |
N1—H1B | 1.041 (17) | C8—C9 | 1.351 (4) |
N1—C1 | 1.314 (7) | C9—H9 | 1.090 (8) |
N1A—H1C | 0.990 (14) | C9—C10 | 1.472 (6) |
N1A—H1D | 1.058 (17) | C10—C15 | 1.404 (4) |
N1A—C1 | 1.291 (7) | C10—C11 | 1.405 (4) |
O1A—C1 | 1.295 (10) | C11—H11 | 1.083 (8) |
N2—C1 | 1.379 (3) | C11—C12 | 1.394 (6) |
N2—C15 | 1.429 (4) | C12—H12 | 1.083 (7) |
N2—C2 | 1.431 (3) | C12—C13 | 1.401 (5) |
C2—C3 | 1.398 (5) | C13—H13 | 1.080 (10) |
C2—C7 | 1.408 (4) | C13—C14 | 1.389 (5) |
C3—H3 | 1.085 (9) | C14—H14 | 1.093 (9) |
C3—C4 | 1.394 (4) | C14—C15 | 1.400 (5) |
C4—H4 | 1.084 (8) | O2—H2C | 0.931 (15) |
C4—C5 | 1.399 (5) | O2—H2A | 0.975 (14) |
C5—H5 | 1.094 (7) | O2—H2B | 1.108 (16) |
C5—C6 | 1.389 (5) | O3—H3B | 0.950 (16) |
C6—H6 | 1.091 (9) | O3—H3A | 0.974 (19) |
C6—C7 | 1.408 (4) | O3—H3C | 1.110 (17) |
H1A—N1—H1B | 118.1 (13) | C2—C7—C8 | 123.3 (2) |
H1A—N1—C1 | 121.7 (11) | C6—C7—C8 | 119.2 (3) |
H1B—N1—C1 | 117.3 (9) | H8—C8—C9 | 117.3 (5) |
H1C—N1A—H1D | 116.4 (14) | H8—C8—C7 | 115.6 (5) |
H1C—N1A—C1 | 125.0 (11) | C9—C8—C7 | 126.8 (4) |
H1D—N1A—C1 | 116.8 (9) | H9—C9—C8 | 117.8 (5) |
C1—N2—C15 | 121.4 (2) | H9—C9—C10 | 116.1 (5) |
C1—N2—C2 | 121.8 (2) | C8—C9—C10 | 125.8 (3) |
C15—N2—C2 | 116.8 (2) | C15—C10—C11 | 118.2 (3) |
N1A—C1—O1A | 122.1 (6) | C15—C10—C9 | 123.1 (3) |
N1—C1—O1 | 118.9 (6) | C11—C10—C9 | 118.7 (3) |
N1A—C1—N2 | 118.3 (4) | H11—C11—C12 | 120.0 (6) |
O1A—C1—N2 | 118.5 (6) | H11—C11—C10 | 118.9 (6) |
N1—C1—N2 | 119.7 (4) | C12—C11—C10 | 121.0 (3) |
O1—C1—N2 | 119.8 (5) | H12—C12—C11 | 120.0 (6) |
C3—C2—C7 | 121.3 (2) | H12—C12—C13 | 120.0 (6) |
C3—C2—N2 | 119.7 (3) | C11—C12—C13 | 119.9 (3) |
C7—C2—N2 | 119.0 (3) | H13—C13—C14 | 120.1 (5) |
H3—C3—C4 | 120.9 (5) | H13—C13—C12 | 120.2 (5) |
H3—C3—C2 | 119.0 (5) | C14—C13—C12 | 119.7 (4) |
C4—C3—C2 | 120.0 (3) | H14—C14—C13 | 120.6 (6) |
H4—C4—C3 | 119.3 (6) | H14—C14—C15 | 119.1 (6) |
H4—C4—C5 | 121.1 (5) | C13—C14—C15 | 120.3 (3) |
C3—C4—C5 | 119.6 (3) | C14—C15—C10 | 120.8 (3) |
H5—C5—C6 | 120.6 (6) | C14—C15—N2 | 119.8 (3) |
H5—C5—C4 | 119.3 (6) | C10—C15—N2 | 119.4 (3) |
C6—C5—C4 | 120.1 (2) | H2C—O2—H2A | 104.1 (14) |
H6—C6—C5 | 120.2 (5) | H2A—O2—H2B | 108.8 (15) |
H6—C6—C7 | 118.4 (5) | H3B—O3—H3A | 107.1 (16) |
C5—C6—C7 | 121.4 (3) | H3A—O3—H3C | 108.7 (16) |
C2—C7—C6 | 117.5 (3) | ||
H1C—N1A—C1—O1A | 179 (2) | C3—C2—C7—C8 | 177.6 (4) |
H1D—N1A—C1—O1A | −16.4 (18) | N2—C2—C7—C8 | −2.2 (6) |
H1C—N1A—C1—N1 | −167.5 (19) | H6—C6—C7—C2 | −179.6 (7) |
H1D—N1A—C1—N1 | −3.3 (17) | C5—C6—C7—C2 | 1.2 (6) |
H1C—N1A—C1—O1 | −90 (4) | H6—C6—C7—C8 | 1.1 (8) |
H1D—N1A—C1—O1 | 75 (4) | C5—C6—C7—C8 | −178.1 (4) |
H1C—N1A—C1—N2 | 11 (2) | C2—C7—C8—H8 | 152.4 (7) |
H1D—N1A—C1—N2 | 175.5 (13) | C6—C7—C8—H8 | −28.3 (7) |
H1A—N1—C1—N1A | −169.3 (17) | C2—C7—C8—C9 | −33.7 (6) |
H1B—N1—C1—N1A | −9.0 (18) | C6—C7—C8—C9 | 145.5 (4) |
H1A—N1—C1—O1A | −75 (4) | H8—C8—C9—H9 | 0.0 (10) |
H1B—N1—C1—O1A | 85 (4) | C7—C8—C9—H9 | −173.7 (7) |
H1A—N1—C1—O1 | 177.6 (17) | H8—C8—C9—C10 | 173.1 (7) |
H1B—N1—C1—O1 | −22.0 (18) | C7—C8—C9—C10 | −0.6 (6) |
H1A—N1—C1—N2 | 11.9 (18) | H9—C9—C10—C15 | −151.8 (6) |
H1B—N1—C1—N2 | 172.2 (14) | C8—C9—C10—C15 | 34.9 (5) |
C15—N2—C1—N1A | 174.5 (5) | H9—C9—C10—C11 | 27.6 (7) |
C2—N2—C1—N1A | −3.2 (7) | C8—C9—C10—C11 | −145.6 (4) |
C15—N2—C1—O1A | 5.9 (9) | C15—C10—C11—H11 | 179.7 (6) |
C2—N2—C1—O1A | −171.8 (8) | C9—C10—C11—H11 | 0.2 (7) |
C15—N2—C1—N1 | −6.7 (7) | C15—C10—C11—C12 | −2.2 (5) |
C2—N2—C1—N1 | 175.6 (6) | C9—C10—C11—C12 | 178.3 (3) |
C15—N2—C1—O1 | −172.3 (8) | H11—C11—C12—H12 | −1.8 (10) |
C2—N2—C1—O1 | 10.0 (9) | C10—C11—C12—H12 | −179.9 (7) |
C1—N2—C2—C3 | 64.5 (5) | H11—C11—C12—C13 | 179.2 (7) |
C15—N2—C2—C3 | −113.3 (4) | C10—C11—C12—C13 | 1.1 (5) |
C1—N2—C2—C7 | −115.7 (4) | H12—C12—C13—H13 | 1.0 (10) |
C15—N2—C2—C7 | 66.5 (5) | C11—C12—C13—H13 | 180.0 (7) |
C7—C2—C3—H3 | −178.4 (7) | H12—C12—C13—C14 | −179.2 (7) |
N2—C2—C3—H3 | 1.3 (8) | C11—C12—C13—C14 | −0.2 (6) |
C7—C2—C3—C4 | 1.0 (6) | H13—C13—C14—H14 | 0.4 (10) |
N2—C2—C3—C4 | −179.2 (4) | C12—C13—C14—H14 | −179.4 (7) |
H3—C3—C4—H4 | −0.4 (11) | H13—C13—C14—C15 | −179.8 (7) |
C2—C3—C4—H4 | −179.8 (7) | C12—C13—C14—C15 | 0.4 (6) |
H3—C3—C4—C5 | 179.5 (7) | H14—C14—C15—C10 | 178.3 (7) |
C2—C3—C4—C5 | 0.0 (6) | C13—C14—C15—C10 | −1.5 (5) |
H4—C4—C5—H5 | −0.6 (11) | H14—C14—C15—N2 | −1.2 (8) |
C3—C4—C5—H5 | 179.6 (7) | C13—C14—C15—N2 | 179.0 (3) |
H4—C4—C5—C6 | 179.4 (7) | C11—C10—C15—C14 | 2.4 (5) |
C3—C4—C5—C6 | −0.4 (6) | C9—C10—C15—C14 | −178.2 (3) |
H5—C5—C6—H6 | 0.6 (11) | C11—C10—C15—N2 | −178.2 (3) |
C4—C5—C6—H6 | −179.4 (7) | C9—C10—C15—N2 | 1.3 (5) |
H5—C5—C6—C7 | 179.8 (7) | C1—N2—C15—C14 | −64.6 (5) |
C4—C5—C6—C7 | −0.2 (6) | C2—N2—C15—C14 | 113.1 (4) |
C3—C2—C7—C6 | −1.6 (6) | C1—N2—C15—C10 | 115.9 (4) |
N2—C2—C7—C6 | 178.6 (3) | C2—N2—C15—C10 | −66.3 (4) |
C15H12N2O·2(H2O) | F(000) = 576 |
Mr = 272.3 | Dx = 1.311 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1597 reflections |
a = 10.144 (4) Å | θ = 2.8–25.2° |
b = 28.891 (11) Å | µ = 0.09 mm−1 |
c = 4.847 (2) Å | T = 100 K |
β = 103.763 (12)° | Prism, colourless |
V = 1379.7 (10) Å3 | 0.4 × 0.29 × 0.18 mm |
Z = 4 |
Bruker APEX-II diffractometer | 2433 independent reflections |
Radiation source: sealed x-ray tube | 1534 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.068 |
φ or ω oscillation scans | θmax = 25.0°, θmin = 1.4° |
Absorption correction: multi-scan SADABS2012/1 - Bruker AXS area detector scaling and absorption correction | h = −12→12 |
Tmin = 0.648, Tmax = 0.745 | k = −34→34 |
13851 measured reflections | l = −6→6 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: structure-invariant direct methods |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: mixed |
wR(F2) = 0.082 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0242P)2] where P = (Fo2 + 2Fc2)/3 |
2433 reflections | (Δ/σ)max < 0.001 |
214 parameters | Δρmax = 0.18 e Å−3 |
10 restraints | Δρmin = −0.18 e Å−3 |
0 constraints |
C15H12N2O·2(H2O) | V = 1379.7 (10) Å3 |
Mr = 272.3 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.144 (4) Å | µ = 0.09 mm−1 |
b = 28.891 (11) Å | T = 100 K |
c = 4.847 (2) Å | 0.4 × 0.29 × 0.18 mm |
β = 103.763 (12)° |
Bruker APEX-II diffractometer | 2433 independent reflections |
Absorption correction: multi-scan SADABS2012/1 - Bruker AXS area detector scaling and absorption correction | 1534 reflections with I > 2σ(I) |
Tmin = 0.648, Tmax = 0.745 | Rint = 0.068 |
13851 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 10 restraints |
wR(F2) = 0.082 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | Δρmax = 0.18 e Å−3 |
2433 reflections | Δρmin = −0.18 e Å−3 |
214 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.3864 (5) | 0.04784 (17) | 0.5278 (9) | 0.0142 (12)* | 0.5 |
N1A | 0.3827 (7) | 0.0458 (2) | 0.5714 (12) | 0.0184 (16)* | 0.5 |
N1 | 0.6164 (7) | 0.0483 (2) | 0.6358 (11) | 0.0184 (16)* | 0.5 |
O1A | 0.6147 (5) | 0.04588 (17) | 0.6820 (9) | 0.0142 (12)* | 0.5 |
N2 | 0.50028 (19) | 0.11071 (5) | 0.7684 (3) | 0.0167 (4) | |
C1 | 0.5000 (2) | 0.06664 (6) | 0.6571 (4) | 0.0172 (5) | |
C2 | 0.3756 (2) | 0.13429 (7) | 0.7725 (4) | 0.0165 (5) | |
C3 | 0.2904 (2) | 0.11688 (7) | 0.9343 (4) | 0.0192 (5) | |
H3 | 0.3153 | 0.0897 | 1.0443 | 0.023* | |
C4 | 0.1692 (2) | 0.13919 (7) | 0.9357 (4) | 0.0202 (5) | |
H4 | 0.111 | 0.1272 | 1.0458 | 0.024* | |
C5 | 0.1335 (2) | 0.17915 (7) | 0.7745 (4) | 0.0191 (5) | |
H5 | 0.0506 | 0.1944 | 0.7739 | 0.023* | |
C6 | 0.2187 (2) | 0.19659 (7) | 0.6156 (4) | 0.0187 (5) | |
H6 | 0.1928 | 0.2238 | 0.5061 | 0.022* | |
C7 | 0.3423 (2) | 0.17523 (6) | 0.6117 (4) | 0.0153 (5) | |
C8 | 0.4321 (2) | 0.19605 (7) | 0.4476 (4) | 0.0177 (5) | |
H8 | 0.3892 | 0.2111 | 0.2755 | 0.021* | |
C9 | 0.5683 (2) | 0.19592 (7) | 0.5157 (4) | 0.0178 (5) | |
H9 | 0.6117 | 0.2108 | 0.3863 | 0.021* | |
C10 | 0.6575 (2) | 0.17523 (7) | 0.7691 (4) | 0.0164 (5) | |
C11 | 0.7816 (2) | 0.19654 (7) | 0.8968 (4) | 0.0192 (5) | |
H11 | 0.8078 | 0.2237 | 0.8127 | 0.023* | |
C12 | 0.8666 (2) | 0.17921 (7) | 1.1413 (4) | 0.0184 (5) | |
H12 | 0.9492 | 0.1947 | 1.2241 | 0.022* | |
C13 | 0.8315 (2) | 0.13912 (7) | 1.2666 (4) | 0.0202 (5) | |
H13 | 0.89 | 0.127 | 1.4339 | 0.024* | |
C14 | 0.7098 (2) | 0.11696 (7) | 1.1437 (4) | 0.0188 (5) | |
H14 | 0.6846 | 0.0898 | 1.229 | 0.023* | |
C15 | 0.6246 (2) | 0.13438 (7) | 0.8966 (4) | 0.0161 (5) | |
H1A | 0.6980 (16) | 0.0567 (12) | 0.744 (7) | 0.020 (6)* | 0.5 |
H1B | 0.613 (4) | 0.0179 (4) | 0.595 (7) | 0.020 (6)* | 0.5 |
H1C | 0.3025 (17) | 0.0606 (10) | 0.539 (8) | 0.020 (6)* | 0.5 |
H1D | 0.392 (4) | 0.0186 (5) | 0.487 (7) | 0.020 (6)* | 0.5 |
O2 | 0.0834 (2) | 0.04804 (6) | 0.3458 (3) | 0.0365 (5) | |
H2A | 0.037 (2) | 0.0527 (9) | 0.480 (4) | 0.067 (10)* | |
H2B | 0.1718 (17) | 0.054 (2) | 0.424 (13) | 0.12 (3)* | 0.5 |
H2C | 0.094 (7) | 0.0173 (3) | 0.330 (13) | 0.09 (2)* | 0.5 |
O3 | 0.9176 (2) | 0.04805 (6) | 0.7630 (3) | 0.0374 (5) | |
H3A | 0.961 (3) | 0.0507 (9) | 0.9472 (18) | 0.068 (9)* | |
H3B | 0.917 (6) | 0.0175 (3) | 0.726 (10) | 0.044 (15)* | 0.5 |
H3C | 0.8300 (17) | 0.055 (2) | 0.751 (13) | 0.10 (3)* | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
N2 | 0.0173 (11) | 0.0108 (8) | 0.0222 (9) | 0.0004 (8) | 0.0050 (8) | −0.0021 (7) |
C1 | 0.0226 (14) | 0.0143 (10) | 0.0147 (10) | 0.0018 (11) | 0.0046 (10) | 0.0030 (8) |
C2 | 0.0171 (14) | 0.0151 (11) | 0.0159 (10) | −0.0004 (10) | 0.0014 (9) | −0.0036 (8) |
C3 | 0.0254 (15) | 0.0138 (11) | 0.0172 (10) | −0.0028 (11) | 0.0029 (10) | −0.0009 (8) |
C4 | 0.0237 (15) | 0.0190 (11) | 0.0191 (11) | −0.0033 (11) | 0.0075 (10) | −0.0050 (9) |
C5 | 0.0168 (14) | 0.0206 (12) | 0.0190 (11) | 0.0012 (10) | 0.0023 (10) | −0.0048 (9) |
C6 | 0.0205 (14) | 0.0161 (11) | 0.0176 (10) | 0.0021 (10) | 0.0008 (10) | −0.0003 (8) |
C7 | 0.0179 (13) | 0.0133 (10) | 0.0131 (10) | −0.0009 (10) | 0.0007 (9) | −0.0027 (8) |
C8 | 0.0247 (16) | 0.0149 (11) | 0.0134 (10) | 0.0011 (10) | 0.0040 (10) | 0.0009 (8) |
C9 | 0.0242 (16) | 0.0136 (11) | 0.0167 (10) | −0.0023 (10) | 0.0070 (10) | −0.0018 (8) |
C10 | 0.0188 (14) | 0.0153 (11) | 0.0160 (10) | 0.0021 (10) | 0.0061 (9) | −0.0027 (8) |
C11 | 0.0243 (15) | 0.0149 (11) | 0.0209 (11) | −0.0020 (10) | 0.0103 (10) | −0.0033 (9) |
C12 | 0.0165 (14) | 0.0181 (11) | 0.0202 (11) | −0.0002 (10) | 0.0034 (10) | −0.0052 (9) |
C13 | 0.0245 (15) | 0.0183 (11) | 0.0167 (10) | 0.0042 (11) | 0.0030 (10) | −0.0021 (8) |
C14 | 0.0237 (15) | 0.0140 (11) | 0.0192 (11) | 0.0006 (10) | 0.0059 (10) | −0.0014 (8) |
C15 | 0.0174 (14) | 0.0137 (10) | 0.0183 (10) | 0.0013 (10) | 0.0061 (10) | −0.0042 (8) |
O2 | 0.0595 (16) | 0.0239 (10) | 0.0306 (9) | −0.0041 (10) | 0.0198 (10) | −0.0038 (8) |
O3 | 0.0615 (16) | 0.0253 (10) | 0.0241 (9) | 0.0071 (10) | 0.0078 (9) | −0.0002 (8) |
O1—C1 | 1.292 (6) | C7—C8 | 1.473 (3) |
N1A—C1 | 1.310 (7) | C8—C9 | 1.342 (3) |
N1A—H1C | 0.9000 (11) | C8—H8 | 0.95 |
N1A—H1D | 0.9000 (11) | C9—C10 | 1.468 (3) |
N1—C1 | 1.321 (7) | C9—H9 | 0.95 |
N1—H1A | 0.9000 (11) | C10—C11 | 1.406 (3) |
N1—H1B | 0.9001 (11) | C10—C15 | 1.409 (3) |
O1A—C1 | 1.290 (5) | C11—C12 | 1.383 (3) |
N2—C1 | 1.382 (2) | C11—H11 | 0.95 |
N2—C15 | 1.439 (3) | C12—C13 | 1.393 (3) |
N2—C2 | 1.441 (3) | C12—H12 | 0.95 |
C2—C3 | 1.392 (3) | C13—C14 | 1.393 (3) |
C2—C7 | 1.412 (3) | C13—H13 | 0.95 |
C3—C4 | 1.390 (3) | C14—C15 | 1.394 (3) |
C3—H3 | 0.95 | C14—H14 | 0.95 |
C4—C5 | 1.393 (3) | O2—H2A | 0.9000 (11) |
C4—H4 | 0.95 | O2—H2B | 0.9000 (11) |
C5—C6 | 1.382 (3) | O2—H2C | 0.9000 (11) |
C5—H5 | 0.95 | O3—H3A | 0.9000 (11) |
C6—C7 | 1.401 (3) | O3—H3B | 0.9000 (11) |
C6—H6 | 0.95 | O3—H3C | 0.9000 (11) |
C1—N1A—H1C | 123 (2) | C6—C7—C8 | 119.86 (17) |
C1—N1A—H1D | 111 (3) | C2—C7—C8 | 122.83 (19) |
H1C—N1A—H1D | 122 (4) | C9—C8—C7 | 126.79 (19) |
C1—N1—H1A | 124 (2) | C9—C8—H8 | 116.6 |
C1—N1—H1B | 115 (3) | C7—C8—H8 | 116.6 |
H1A—N1—H1B | 112 (4) | C8—C9—C10 | 126.90 (19) |
C1—N2—C15 | 121.78 (18) | C8—C9—H9 | 116.6 |
C1—N2—C2 | 121.35 (18) | C10—C9—H9 | 116.6 |
C15—N2—C2 | 116.81 (14) | C11—C10—C15 | 117.05 (19) |
O1A—C1—N1A | 123.1 (4) | C11—C10—C9 | 119.93 (18) |
O1—C1—N1 | 120.3 (4) | C15—C10—C9 | 123.0 (2) |
O1A—C1—N2 | 118.3 (3) | C12—C11—C10 | 121.97 (19) |
O1—C1—N2 | 119.7 (3) | C12—C11—H11 | 119 |
N1A—C1—N2 | 117.8 (3) | C10—C11—H11 | 119 |
N1—C1—N2 | 118.7 (3) | C11—C12—C13 | 120.2 (2) |
C3—C2—C7 | 120.96 (19) | C11—C12—H12 | 119.9 |
C3—C2—N2 | 120.09 (17) | C13—C12—H12 | 119.9 |
C7—C2—N2 | 118.95 (17) | C12—C13—C14 | 119.3 (2) |
C4—C3—C2 | 120.25 (19) | C12—C13—H13 | 120.4 |
C4—C3—H3 | 119.9 | C14—C13—H13 | 120.4 |
C2—C3—H3 | 119.9 | C13—C14—C15 | 120.46 (19) |
C3—C4—C5 | 119.59 (19) | C13—C14—H14 | 119.8 |
C3—C4—H4 | 120.2 | C15—C14—H14 | 119.8 |
C5—C4—H4 | 120.2 | C14—C15—C10 | 121.1 (2) |
C6—C5—C4 | 120.1 (2) | C14—C15—N2 | 120.00 (17) |
C6—C5—H5 | 120 | C10—C15—N2 | 118.92 (18) |
C4—C5—H5 | 120 | H2A—O2—H2B | 108 (5) |
C5—C6—C7 | 121.79 (18) | H2A—O2—H2C | 107 (4) |
C5—C6—H6 | 119.1 | H3A—O3—H3B | 105 (4) |
C7—C6—H6 | 119.1 | H3A—O3—H3C | 107 (4) |
C6—C7—C2 | 117.30 (18) | ||
C15—N2—C1—O1A | 3.1 (3) | N2—C2—C7—C8 | −2.4 (3) |
C2—N2—C1—O1A | −174.1 (2) | C6—C7—C8—C9 | 145.4 (2) |
C15—N2—C1—O1 | −175.6 (2) | C2—C7—C8—C9 | −33.6 (3) |
C2—N2—C1—O1 | 7.2 (3) | C7—C8—C9—C10 | −0.3 (4) |
C15—N2—C1—N1A | 173.0 (3) | C8—C9—C10—C11 | −145.2 (2) |
C2—N2—C1—N1A | −4.2 (4) | C8—C9—C10—C15 | 34.2 (3) |
C15—N2—C1—N1 | −8.7 (4) | C15—C10—C11—C12 | −1.8 (3) |
C2—N2—C1—N1 | 174.1 (3) | C9—C10—C11—C12 | 177.71 (18) |
C1—N2—C2—C3 | 64.5 (2) | C10—C11—C12—C13 | 1.0 (3) |
C15—N2—C2—C3 | −112.8 (2) | C11—C12—C13—C14 | −0.4 (3) |
C1—N2—C2—C7 | −115.9 (2) | C12—C13—C14—C15 | 0.7 (3) |
C15—N2—C2—C7 | 66.8 (2) | C13—C14—C15—C10 | −1.6 (3) |
C7—C2—C3—C4 | 1.3 (3) | C13—C14—C15—N2 | 178.80 (16) |
N2—C2—C3—C4 | −179.10 (19) | C11—C10—C15—C14 | 2.0 (3) |
C2—C3—C4—C5 | −0.2 (3) | C9—C10—C15—C14 | −177.40 (18) |
C3—C4—C5—C6 | −0.3 (3) | C11—C10—C15—N2 | −178.31 (16) |
C4—C5—C6—C7 | −0.3 (3) | C9—C10—C15—N2 | 2.2 (3) |
C5—C6—C7—C2 | 1.4 (3) | C1—N2—C15—C14 | −64.5 (2) |
C5—C6—C7—C8 | −177.71 (19) | C2—N2—C15—C14 | 112.9 (2) |
C3—C2—C7—C6 | −1.8 (3) | C1—N2—C15—C10 | 115.9 (2) |
N2—C2—C7—C6 | 178.53 (18) | C2—N2—C15—C10 | −66.8 (2) |
C3—C2—C7—C8 | 177.20 (19) |
C15H12N2O·2(H2O) | F(000) = 1152 |
Mr = 272.3 | Dx = 1.319 Mg m−3 |
Orthorhombic, Cmca | Cell parameters from 0 reflections |
Hall symbol: -C 2bc 2 | θ = 0–0° |
a = 19.638 (6) Å | µ = 0 mm−1 |
b = 4.8378 (16) Å | T = 100 K |
c = 28.856 (8) Å | Prism, colourless |
V = 2741.5 (14) Å3 | 8 × 2 × 2 mm |
Z = 8 |
SXD beamline diffractometer | 5374 reflections with I > 2σ(I) |
Radiation source: ISIS neutron spallation source | θmax = 84.0°, θmin = 9.5° |
time of flight Laue diffraction scans | h = −53→40 |
5374 measured reflections | k = −9→5 |
5374 independent reflections | l = −56→111 |
Refinement on F2 | Secondary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.065 | All H-atom parameters refined |
wR(F2) = 0.171 | w = 1/[σ2(Fo2) + (0.1195P)2 + 83.2386P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
5374 reflections | Δρmax = 1.60 e Å−3 |
188 parameters | Δρmin = −1.51 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 constraints | Extinction coefficient: 0.00025 (3) |
Primary atom site location: structure-invariant direct methods |
C15H12N2O·2(H2O) | V = 2741.5 (14) Å3 |
Mr = 272.3 | Z = 8 |
Orthorhombic, Cmca | µ = 0 mm−1 |
a = 19.638 (6) Å | T = 100 K |
b = 4.8378 (16) Å | 8 × 2 × 2 mm |
c = 28.856 (8) Å |
SXD beamline diffractometer | 5374 independent reflections |
5374 measured reflections | 5374 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.065 | 0 restraints |
wR(F2) = 0.171 | All H-atom parameters refined |
S = 1.07 | w = 1/[σ2(Fo2) + (0.1195P)2 + 83.2386P] where P = (Fo2 + 2Fc2)/3 |
5374 reflections | Δρmax = 1.60 e Å−3 |
188 parameters | Δρmin = −1.51 e Å−3 |
Experimental. For peak integration a local UB matrix refined for each frame, using approximately 30 reflections from each of the 11 detectors. Hence _cell_measurement_reflns_used 330 For final cell dimensions a weighted average of all local cells was calculated. Because of the nature of the experiment, it is not possible to give values of theta_min and theta_max for the cell determination. The same applies for the wavelength used for the experiment. The range of wavelengths used was 0.42–7.97 Angstroms, BUT the bulk of the diffraction information is obtained from wavelengths in the range 0.7–2.5 Angstroms. The data collection procedures on the SXD instrument used for the single-crystal neutron data collection are most recently summarized in following paper: Keen, D. A.; Gutmann, M. J.; Wilson, C·C. (2006). J. Appl. Cryst. 39,714. |
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. The variable wavelength nature of the data collection procedure means that sensible values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max cannot be given. Instead, the following limits are given: _diffrn_reflns_sin(theta)/lambda_min 0.034 _diffrn_reflns_sin(theta)/lambda_max 2.268 _refine_diff_density_max/min is given in Fermi per Angstrom cubed not electrons per angstrom cubed. Another way to consider the _refine_diff_density_ is as a percentage of the scattering density of a given atom: _refine_diff_density_max = 4.4% of C atom _refine_diff_density_min = −4.4% of C atom |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | −0.0576 (4) | 0.136 (2) | 0.5453 (3) | 0.0088 (19)* | 0.5 |
O2 | 0.2082 (2) | 0.0550 (12) | 0.54803 (13) | 0.0295 (10) | |
N1 | 0.0580 (2) | 0.0835 (15) | 0.54742 (19) | 0.0105 (13)* | 0.5 |
N2 | 0 | 0.2690 (7) | 0.61070 (7) | 0.0115 (6) | |
C1 | 0 | 0.1573 (10) | 0.56669 (10) | 0.0115 (8) | |
C2 | −0.06199 (9) | 0.3341 (7) | 0.63426 (7) | 0.0100 (6) | |
C3 | −0.10488 (10) | 0.5393 (7) | 0.61662 (8) | 0.0128 (6) | |
C4 | −0.16578 (10) | 0.6015 (8) | 0.63896 (8) | 0.0139 (6) | |
C5 | −0.18376 (10) | 0.4577 (7) | 0.67927 (8) | 0.0134 (6) | |
C6 | −0.14081 (10) | 0.2542 (8) | 0.69683 (8) | 0.0123 (6) | |
C7 | −0.07862 (9) | 0.1908 (7) | 0.67511 (7) | 0.0101 (6) | |
C8 | −0.03442 (10) | −0.0202 (7) | 0.69593 (7) | 0.0118 (6) | |
H1A | 0.1032 (4) | 0.141 (4) | 0.5610 (4) | 0.031 (4) | 0.5 |
H1B | 0.0565 (4) | 0.025 (3) | 0.5131 (3) | 0.024 (3) | 0.5 |
H2A | 0.2337 (5) | 0.225 (2) | 0.5526 (3) | 0.046 (2) | |
H2B | 0.2097 (5) | 0.022 (4) | 0.5160 (3) | 0.029 (3) | 0.5 |
H2C | 0.1533 (6) | 0.100 (4) | 0.5533 (4) | 0.034 (4) | 0.5 |
H3 | −0.0898 (3) | 0.6498 (18) | 0.58540 (19) | 0.0313 (17) | |
H4 | −0.1987 (3) | 0.7603 (18) | 0.6251 (2) | 0.0304 (16) | |
H5 | −0.2317 (2) | 0.5049 (18) | 0.6966 (2) | 0.0307 (16) | |
H6 | −0.1544 (2) | 0.1444 (18) | 0.72831 (18) | 0.0285 (17) | |
H8 | −0.0601 (2) | −0.1798 (17) | 0.7161 (2) | 0.0281 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.051 (2) | 0.021 (3) | 0.0171 (14) | −0.0067 (19) | 0.0066 (13) | −0.0029 (18) |
N2 | 0.0103 (7) | 0.0188 (19) | 0.0053 (8) | 0 | 0 | −0.0014 (10) |
C1 | 0.0113 (10) | 0.017 (3) | 0.0056 (10) | 0 | 0 | −0.0008 (14) |
C2 | 0.0098 (7) | 0.0146 (18) | 0.0056 (7) | 0.0010 (8) | −0.0001 (5) | 0.0000 (9) |
C3 | 0.0138 (8) | 0.016 (2) | 0.0085 (8) | 0.0025 (9) | −0.0009 (6) | 0.0011 (10) |
C4 | 0.0129 (8) | 0.0166 (19) | 0.0122 (9) | 0.0032 (9) | −0.0015 (6) | −0.0009 (11) |
C5 | 0.0097 (7) | 0.017 (2) | 0.0133 (9) | 0.0021 (8) | 0.0009 (6) | −0.0010 (11) |
C6 | 0.0090 (7) | 0.0173 (19) | 0.0106 (8) | −0.0004 (8) | 0.0016 (5) | 0.0014 (11) |
C7 | 0.0095 (7) | 0.0130 (18) | 0.0077 (7) | −0.0002 (8) | 0.0007 (6) | 0.0008 (9) |
C8 | 0.0097 (7) | 0.0161 (19) | 0.0098 (8) | −0.0003 (9) | −0.0001 (6) | 0.0008 (11) |
H1A | 0.017 (4) | 0.056 (12) | 0.021 (5) | 0.000 (5) | −0.002 (3) | −0.010 (6) |
H1B | 0.023 (4) | 0.037 (10) | 0.013 (3) | 0.001 (4) | 0.000 (3) | −0.002 (5) |
H2A | 0.076 (5) | 0.028 (6) | 0.034 (3) | −0.013 (5) | −0.003 (3) | −0.004 (4) |
H2B | 0.030 (4) | 0.039 (11) | 0.018 (4) | 0.001 (5) | −0.001 (3) | −0.001 (6) |
H2C | 0.032 (5) | 0.044 (12) | 0.027 (5) | 0.004 (6) | 0.002 (4) | −0.005 (6) |
H3 | 0.033 (2) | 0.043 (6) | 0.018 (2) | 0.006 (3) | 0.0042 (16) | 0.010 (3) |
H4 | 0.030 (2) | 0.029 (5) | 0.032 (3) | 0.012 (3) | −0.0033 (18) | 0.003 (3) |
H5 | 0.0193 (19) | 0.041 (5) | 0.032 (2) | 0.005 (2) | 0.0064 (17) | 0.001 (3) |
H6 | 0.0240 (19) | 0.041 (5) | 0.021 (2) | 0.000 (2) | 0.0071 (15) | 0.010 (3) |
H8 | 0.024 (2) | 0.028 (5) | 0.032 (3) | −0.006 (2) | 0.0031 (18) | 0.012 (3) |
O1—C1 | 1.292 (8) | C2—C7 | 1.406 (3) |
O2—H2B | 0.939 (11) | C3—H3 | 1.089 (7) |
O2—H2A | 0.973 (13) | C3—C4 | 1.392 (3) |
O2—H2C | 1.109 (12) | C4—H4 | 1.081 (7) |
N1—H1A | 1.009 (11) | C4—C5 | 1.400 (4) |
N1—H1B | 1.031 (11) | C5—H5 | 1.089 (5) |
N1—C1 | 1.316 (5) | C5—C6 | 1.392 (4) |
N2—C1 | 1.380 (4) | C6—H6 | 1.086 (6) |
N2—C2i | 1.429 (2) | C6—C7 | 1.407 (3) |
N2—C2 | 1.429 (2) | C7—C8 | 1.468 (4) |
C1—O1i | 1.292 (8) | C8—H8 | 1.091 (7) |
C1—N1i | 1.316 (6) | C8—C8i | 1.352 (4) |
C2—C3 | 1.398 (4) | ||
H2B—O2—H2A | 105.2 (11) | H3—C3—C2 | 119.1 (4) |
H2A—O2—H2C | 108.4 (12) | C4—C3—C2 | 120.2 (2) |
H1A—N1—H1B | 118.2 (9) | H4—C4—C3 | 119.7 (4) |
H1A—N1—C1 | 121.5 (8) | H4—C4—C5 | 120.7 (4) |
H1B—N1—C1 | 117.2 (7) | C3—C4—C5 | 119.6 (3) |
C1—N2—C2i | 121.59 (12) | H5—C5—C6 | 120.3 (5) |
C1—N2—C2 | 121.59 (12) | H5—C5—C4 | 119.6 (5) |
C2i—N2—C2 | 116.8 (2) | C6—C5—C4 | 120.1 (2) |
O1—C1—O1i | 122.2 (8) | H6—C6—C5 | 120.1 (4) |
N1i—C1—N1 | 119.7 (6) | H6—C6—C7 | 118.7 (4) |
O1—C1—N2 | 118.0 (4) | C5—C6—C7 | 121.2 (2) |
O1i—C1—N2 | 118.0 (4) | C2—C7—C6 | 117.9 (2) |
N1i—C1—N2 | 119.7 (3) | C2—C7—C8 | 123.27 (18) |
N1—C1—N2 | 119.7 (3) | C6—C7—C8 | 118.8 (2) |
C3—C2—C7 | 121.03 (19) | H8—C8—C8i | 117.5 (3) |
C3—C2—N2 | 119.8 (2) | H8—C8—C7 | 115.9 (4) |
C7—C2—N2 | 119.2 (2) | C8i—C8—C7 | 126.23 (13) |
H3—C3—C4 | 120.8 (4) | ||
H1A—N1—C1—O1 | 165.6 (14) | H3—C3—C4—H4 | 0.4 (8) |
H1B—N1—C1—O1 | 5.8 (14) | C2—C3—C4—H4 | −179.9 (5) |
H1A—N1—C1—O1i | 73 (3) | H3—C3—C4—C5 | −179.5 (5) |
H1B—N1—C1—O1i | −87 (3) | C2—C3—C4—C5 | 0.1 (4) |
H1A—N1—C1—N1i | 178.6 (11) | H4—C4—C5—H5 | 0.6 (8) |
H1B—N1—C1—N1i | 18.8 (15) | C3—C4—C5—H5 | −179.4 (5) |
H1A—N1—C1—N2 | −12.5 (15) | H4—C4—C5—C6 | −179.8 (5) |
H1B—N1—C1—N2 | −172.3 (11) | C3—C4—C5—C6 | 0.1 (5) |
C2i—N2—C1—O1 | −171.5 (6) | H5—C5—C6—H6 | −1.3 (8) |
C2—N2—C1—O1 | 6.3 (8) | C4—C5—C6—H6 | 179.2 (5) |
C2i—N2—C1—O1i | −6.3 (8) | H5—C5—C6—C7 | −179.8 (5) |
C2—N2—C1—O1i | 171.5 (6) | C4—C5—C6—C7 | 0.7 (5) |
C2i—N2—C1—N1i | 175.6 (5) | C3—C2—C7—C6 | 2.0 (4) |
C2—N2—C1—N1i | −6.6 (6) | N2—C2—C7—C6 | −178.3 (3) |
C2i—N2—C1—N1 | 6.6 (7) | C3—C2—C7—C8 | −178.0 (3) |
C2—N2—C1—N1 | −175.6 (5) | N2—C2—C7—C8 | 1.6 (4) |
C1—N2—C2—C3 | −64.6 (4) | H6—C6—C7—C2 | 179.7 (5) |
C2i—N2—C2—C3 | 113.3 (3) | C5—C6—C7—C2 | −1.8 (4) |
C1—N2—C2—C7 | 115.7 (4) | H6—C6—C7—C8 | −0.3 (6) |
C2i—N2—C2—C7 | −66.4 (5) | C5—C6—C7—C8 | 178.2 (3) |
C7—C2—C3—H3 | 178.4 (5) | C2—C7—C8—H8 | −152.0 (5) |
N2—C2—C3—H3 | −1.2 (6) | C6—C7—C8—H8 | 27.9 (6) |
C7—C2—C3—C4 | −1.2 (4) | C2—C7—C8—C8i | 34.4 (3) |
N2—C2—C3—C4 | 179.1 (3) | C6—C7—C8—C8i | −145.62 (19) |
Symmetry code: (i) −x, y, z. |
C15H12N2O·2(H2O) | F(000) = 1152 |
Mr = 272.3 | Dx = 1.311 Mg m−3 |
Orthorhombic, Cmca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2bc 2 | Cell parameters from 1597 reflections |
a = 19.705 (8) Å | θ = 2.8–25.2° |
b = 4.847 (2) Å | µ = 0.09 mm−1 |
c = 28.891 (11) Å | T = 100 K |
V = 2759.4 (19) Å3 | Prism, colourless |
Z = 8 | 0.4 × 0.29 × 0.18 mm |
Bruker APEX-II diffractometer | 1258 independent reflections |
Radiation source: sealed x-ray tube | 903 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
φ or ω oscillation scans | θmax = 25.0°, θmin = 1.4° |
Absorption correction: multi-scan SADABS2012/1 - Bruker AXS area detector scaling and absorption correction | h = −23→23 |
Tmin = 0.648, Tmax = 0.745 | k = −5→5 |
11763 measured reflections | l = −34→34 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: structure-invariant direct methods |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: mixed |
wR(F2) = 0.074 | Only H-atom displacement parameters refined |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0257P)2 + 0.5684P] where P = (Fo2 + 2Fc2)/3 |
1258 reflections | (Δ/σ)max < 0.001 |
119 parameters | Δρmax = 0.19 e Å−3 |
4 restraints | Δρmin = −0.16 e Å−3 |
0 constraints |
C15H12N2O·2(H2O) | V = 2759.4 (19) Å3 |
Mr = 272.3 | Z = 8 |
Orthorhombic, Cmca | Mo Kα radiation |
a = 19.705 (8) Å | µ = 0.09 mm−1 |
b = 4.847 (2) Å | T = 100 K |
c = 28.891 (11) Å | 0.4 × 0.29 × 0.18 mm |
Bruker APEX-II diffractometer | 1258 independent reflections |
Absorption correction: multi-scan SADABS2012/1 - Bruker AXS area detector scaling and absorption correction | 903 reflections with I > 2σ(I) |
Tmin = 0.648, Tmax = 0.745 | Rint = 0.069 |
11763 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 4 restraints |
wR(F2) = 0.074 | Only H-atom displacement parameters refined |
S = 1.01 | Δρmax = 0.19 e Å−3 |
1258 reflections | Δρmin = −0.16 e Å−3 |
119 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.4417 (3) | 0.6295 (10) | 0.45437 (18) | 0.0161 (18)* | 0.5 |
O1 | 0.5572 (2) | 0.5843 (8) | 0.45207 (14) | 0.0154 (14)* | 0.5 |
N2 | 0.5 | 0.7683 (4) | 0.38929 (6) | 0.0165 (5) | |
C1 | 0.5 | 0.6571 (4) | 0.43337 (7) | 0.0167 (6) | |
C2 | 0.43777 (9) | 0.8345 (3) | 0.36565 (5) | 0.0163 (4) | |
C3 | 0.39516 (9) | 1.0389 (3) | 0.38309 (5) | 0.0188 (4) | |
H3 | 0.4077 | 1.1366 | 0.4103 | 0.024 (5)* | |
C4 | 0.33435 (9) | 1.1009 (3) | 0.36086 (5) | 0.0201 (4) | |
H4 | 0.3051 | 1.2393 | 0.3729 | 0.028 (5)* | |
C5 | 0.31674 (9) | 0.9580 (3) | 0.32082 (5) | 0.0188 (4) | |
H5 | 0.2754 | 0.9994 | 0.3054 | 0.019 (4)* | |
C6 | 0.35930 (9) | 0.7561 (3) | 0.30343 (5) | 0.0187 (4) | |
H6 | 0.3463 | 0.6592 | 0.2763 | 0.018 (4)* | |
C7 | 0.42117 (9) | 0.6904 (3) | 0.32478 (5) | 0.0157 (4) | |
C8 | 0.46594 (8) | 0.4815 (3) | 0.30404 (5) | 0.0178 (4) | |
H8 | 0.4444 | 0.3306 | 0.2891 | 0.022 (5)* | |
H1A | 0.4005 (9) | 0.641 (7) | 0.4406 (9) | 0.019 (7)* | 0.5 |
H1B | 0.4447 (15) | 0.543 (6) | 0.4821 (6) | 0.019 (7)* | 0.5 |
O2 | 0.29152 (9) | 0.5540 (3) | 0.45193 (4) | 0.0369 (4) | |
H2A | 0.2699 (11) | 0.708 (3) | 0.4486 (7) | 0.063 (8)* | |
H2B | 0.294 (2) | 0.528 (9) | 0.4815 (5) | 0.054 (15)* | 0.5 |
H2C | 0.343 (3) | 0.590 (13) | 0.445 (2) | 0.12 (2)* | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
N2 | 0.0169 (13) | 0.0219 (10) | 0.0107 (9) | 0 | 0 | 0.0019 (8) |
C1 | 0.0212 (16) | 0.0148 (12) | 0.0142 (12) | 0 | 0 | −0.0020 (9) |
C2 | 0.0177 (10) | 0.0173 (8) | 0.0140 (8) | −0.0027 (7) | 0.0009 (7) | 0.0040 (6) |
C3 | 0.0239 (11) | 0.0184 (8) | 0.0141 (8) | −0.0017 (8) | 0.0018 (8) | 0.0013 (7) |
C4 | 0.0241 (11) | 0.0177 (8) | 0.0184 (9) | 0.0024 (8) | 0.0035 (8) | 0.0039 (7) |
C5 | 0.0164 (10) | 0.0210 (9) | 0.0191 (8) | −0.0004 (8) | −0.0009 (8) | 0.0055 (7) |
C6 | 0.0223 (11) | 0.0187 (8) | 0.0153 (8) | −0.0046 (8) | −0.0018 (8) | 0.0018 (7) |
C7 | 0.0185 (10) | 0.0145 (8) | 0.0142 (8) | −0.0025 (7) | 0.0020 (7) | 0.0029 (6) |
C8 | 0.0245 (9) | 0.0146 (8) | 0.0143 (8) | −0.0017 (7) | −0.0019 (7) | 0.0003 (7) |
O2 | 0.0609 (12) | 0.0256 (8) | 0.0241 (7) | 0.0067 (8) | 0.0056 (7) | 0.0027 (6) |
N1—C1 | 1.305 (6) | C4—C5 | 1.392 (2) |
N1—H1A | 0.907 (15) | C4—H4 | 0.95 |
N1—H1B | 0.907 (15) | C5—C6 | 1.383 (2) |
O1—C1 | 1.299 (5) | C5—H5 | 0.95 |
N2—C1 | 1.383 (3) | C6—C7 | 1.403 (2) |
N2—C2i | 1.4398 (19) | C6—H6 | 0.95 |
N2—C2 | 1.4398 (19) | C7—C8 | 1.471 (2) |
C1—O1i | 1.299 (5) | C8—C8i | 1.342 (3) |
C1—N1i | 1.305 (6) | C8—H8 | 0.95 |
C2—C3 | 1.393 (2) | O2—H2A | 0.866 (14) |
C2—C7 | 1.410 (2) | O2—H2B | 0.866 (14) |
C3—C4 | 1.392 (2) | O2—H2C | 1.06 (6) |
C3—H3 | 0.95 | ||
C1—N1—H1A | 125.3 (19) | C5—C4—C3 | 119.37 (16) |
C1—N1—H1B | 114 (2) | C5—C4—H4 | 120.3 |
H1A—N1—H1B | 118 (3) | C3—C4—H4 | 120.3 |
C1—N2—C2i | 121.58 (9) | C6—C5—C4 | 120.18 (16) |
C1—N2—C2 | 121.58 (9) | C6—C5—H5 | 119.9 |
C2i—N2—C2 | 116.78 (17) | C4—C5—H5 | 119.9 |
O1i—C1—O1 | 120.4 (4) | C5—C6—C7 | 121.84 (15) |
N1i—C1—N1 | 123.2 (5) | C5—C6—H6 | 119.1 |
O1i—C1—N2 | 119.3 (2) | C7—C6—H6 | 119.1 |
O1—C1—N2 | 119.3 (2) | C6—C7—C2 | 117.22 (15) |
N1i—C1—N2 | 117.9 (3) | C6—C7—C8 | 119.89 (14) |
N1—C1—N2 | 117.9 (3) | C2—C7—C8 | 122.88 (15) |
C3—C2—C7 | 121.00 (16) | C8i—C8—C7 | 126.86 (9) |
C3—C2—N2 | 120.03 (15) | C8i—C8—H8 | 116.6 |
C7—C2—N2 | 118.97 (15) | C7—C8—H8 | 116.6 |
C4—C3—C2 | 120.36 (15) | H2A—O2—H2B | 105 (3) |
C4—C3—H3 | 119.8 | H2A—O2—H2C | 108 (4) |
C2—C3—H3 | 119.8 | H2B—O2—H2C | 99 (4) |
C2i—N2—C1—O1i | −175.6 (3) | N2—C2—C3—C4 | −178.90 (15) |
C2—N2—C1—O1i | 7.2 (4) | C2—C3—C4—C5 | −0.5 (2) |
C2i—N2—C1—O1 | −7.2 (4) | C3—C4—C5—C6 | 0.2 (2) |
C2—N2—C1—O1 | 175.6 (3) | C4—C5—C6—C7 | −0.7 (2) |
C2i—N2—C1—N1i | 4.2 (4) | C5—C6—C7—C2 | 1.5 (2) |
C2—N2—C1—N1i | −173.0 (3) | C5—C6—C7—C8 | −177.69 (14) |
C2i—N2—C1—N1 | 173.0 (3) | C3—C2—C7—C6 | −1.9 (2) |
C2—N2—C1—N1 | −4.2 (4) | N2—C2—C7—C6 | 178.42 (14) |
C1—N2—C2—C3 | 64.5 (2) | C3—C2—C7—C8 | 177.33 (14) |
C2i—N2—C2—C3 | −112.90 (18) | N2—C2—C7—C8 | −2.4 (2) |
C1—N2—C2—C7 | −115.8 (2) | C6—C7—C8—C8i | 145.28 (11) |
C2i—N2—C2—C7 | 66.8 (2) | C2—C7—C8—C8i | −33.90 (18) |
C7—C2—C3—C4 | 1.4 (2) |
Symmetry code: (i) −x+1, y, z. |
C15H12N2O | V = 1141.9 (4) Å3 |
Mr = 236.27 | Z = 4 |
Monoclinic, P21/n | Dx = 1.374 Mg m−3 |
Hall symbol: -P 2yn | Cell parameters from 1100 reflections |
a = 7.4980 (15) Å | µ = 0 mm−1 |
b = 11.058 (2) Å | T = 100 K |
c = 13.789 (3) Å | Prism, colourless |
β = 92.838 (16)° | 8 × 2 × 2 mm |
SXD beamline diffractometer | 8450 reflections with I > 2σ(I) |
Radiation source: ISIS neutron spallation source | θmax = 82.8°, θmin = 8.3° |
time of flight Laue diffraction scans | h = −20→15 |
8450 measured reflections | k = −36→21 |
8450 independent reflections | l = −26→36 |
Refinement on F2 | Secondary atom site location: iterative |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.068 | All H-atom parameters refined |
wR(F2) = 0.164 | w = 1/[σ2(Fo2) + (0.0888P)2 + 26.222P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
8450 reflections | Δρmax = 1.85 e Å−3 |
276 parameters | Δρmin = −2.03 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 constraints | Extinction coefficient: 0.0080 (3) |
Primary atom site location: iterative |
C15H12N2O | β = 92.838 (16)° |
Mr = 236.27 | V = 1141.9 (4) Å3 |
Monoclinic, P21/n | Z = 4 |
a = 7.4980 (15) Å | µ = 0 mm−1 |
b = 11.058 (2) Å | T = 100 K |
c = 13.789 (3) Å | 8 × 2 × 2 mm |
SXD beamline diffractometer | 8450 independent reflections |
8450 measured reflections | 8450 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.068 | 0 restraints |
wR(F2) = 0.164 | All H-atom parameters refined |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0888P)2 + 26.222P] where P = (Fo2 + 2Fc2)/3 |
8450 reflections | Δρmax = 1.85 e Å−3 |
276 parameters | Δρmin = −2.03 e Å−3 |
Experimental. For peak integration a local UB matrix refined for each frame, using approximately 100 reflections from each of the 11 detectors. Hence _cell_measurement_reflns_used 1100 For final cell dimensions a weighted average of all local cells was calculated. Because of the nature of the experiment, it is not possible to give values of theta_min and theta_max for the cell determination. The same applies for the wavelength used for the experiment. The range of wavelengths used was 0.48–7.0 Angstroms, BUT the bulk of the diffraction information is obtained from wavelengths in the range 0.7–2.5 Angstroms. The data collection procedures on the SXD instrument used for the single-crystal neutron data collection are most recently summarized in the following paper Keen, D. A.; Gutmann, M. J.; Wilson, C. C. (2006) J. Appl. Cryst.,39,714 |
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. The variable wavelength nature of the data collection procedure means that sensible values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max cannot be given. Instead, the following limits are given: _diffrn_reflns_sin(theta)/lambda_min 0.055 _diffrn_reflns_sin(theta)/lambda_max 1.858 _refine_diff_density_max/min is given in Fermi per Angstrom cubed not electrons per angstrom cubed. Another way to consider the _refine_diff_density_ is as a percentage of the scattering density of a given atom: _refine_diff_density_max = 3.6% of C atom _refine_diff_density_min = −3.4% of C atom |
x | y | z | Uiso*/Ueq | ||
O1 | −0.0097 (3) | 0.3755 (2) | 0.40624 (18) | 0.0115 (4) | |
N1 | 0.1809 (2) | 0.39937 (15) | 0.53878 (12) | 0.0138 (3) | |
N2 | 0.2057 (2) | 0.23188 (13) | 0.43811 (10) | 0.0093 (3) | |
C1 | 0.1181 (3) | 0.33848 (19) | 0.45839 (14) | 0.0082 (3) | |
C2 | 0.1692 (3) | 0.16951 (18) | 0.34828 (14) | 0.0084 (3) | |
C3 | 0.0066 (3) | 0.1093 (2) | 0.33104 (15) | 0.0112 (4) | |
C4 | −0.0302 (3) | 0.0492 (2) | 0.24343 (16) | 0.0126 (4) | |
C5 | 0.0970 (3) | 0.0478 (2) | 0.17257 (16) | 0.0127 (4) | |
C6 | 0.2588 (3) | 0.1071 (2) | 0.18992 (15) | 0.0118 (4) | |
C7 | 0.2992 (3) | 0.16792 (19) | 0.27819 (14) | 0.0089 (3) | |
C8 | 0.4740 (3) | 0.2262 (2) | 0.29228 (16) | 0.0113 (4) | |
C9 | 0.5729 (3) | 0.2409 (2) | 0.37621 (16) | 0.0114 (4) | |
C10 | 0.5266 (3) | 0.19754 (19) | 0.47228 (15) | 0.0093 (3) | |
C11 | 0.6645 (3) | 0.1620 (2) | 0.53951 (16) | 0.0124 (4) | |
C12 | 0.6275 (3) | 0.1157 (2) | 0.62999 (16) | 0.0127 (4) | |
C13 | 0.4507 (3) | 0.1032 (2) | 0.65611 (16) | 0.0135 (4) | |
C14 | 0.3119 (3) | 0.1377 (2) | 0.59078 (16) | 0.0121 (4) | |
C15 | 0.3496 (3) | 0.18671 (18) | 0.50054 (14) | 0.0089 (3) | |
H1A | 0.2865 (8) | 0.3693 (5) | 0.5788 (4) | 0.0298 (13) | |
H1B | 0.1204 (8) | 0.4789 (5) | 0.5562 (4) | 0.0231 (10) | |
H3 | −0.0919 (8) | 0.1102 (6) | 0.3865 (4) | 0.0290 (11) | |
H4 | −0.1574 (8) | 0.0035 (6) | 0.2307 (5) | 0.0306 (12) | |
H5 | 0.0702 (9) | −0.0007 (6) | 0.1044 (4) | 0.0311 (13) | |
H6 | 0.3582 (9) | 0.1057 (6) | 0.1350 (4) | 0.0292 (12) | |
H8 | 0.5356 (9) | 0.2532 (6) | 0.2253 (4) | 0.0308 (13) | |
H9 | 0.7058 (8) | 0.2797 (5) | 0.3726 (4) | 0.0277 (11) | |
H11 | 0.8028 (7) | 0.1726 (6) | 0.5203 (5) | 0.0306 (12) | |
H12 | 0.7363 (8) | 0.0901 (6) | 0.6815 (4) | 0.0304 (13) | |
H13 | 0.4248 (9) | 0.0692 (6) | 0.7282 (4) | 0.0321 (13) | |
H14 | 0.1730 (8) | 0.1299 (6) | 0.6092 (4) | 0.0286 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0106 (9) | 0.0095 (9) | 0.0139 (9) | 0.0040 (7) | −0.0045 (8) | −0.0032 (7) |
N1 | 0.0141 (7) | 0.0128 (7) | 0.0140 (6) | 0.0055 (5) | −0.0042 (5) | −0.0065 (5) |
N2 | 0.0091 (6) | 0.0097 (6) | 0.0089 (5) | 0.0040 (4) | −0.0008 (5) | −0.0024 (4) |
C1 | 0.0078 (7) | 0.0081 (8) | 0.0087 (7) | 0.0019 (6) | 0.0003 (6) | −0.0016 (5) |
C2 | 0.0095 (8) | 0.0077 (8) | 0.0079 (7) | 0.0018 (6) | 0.0002 (6) | −0.0010 (6) |
C3 | 0.0094 (8) | 0.0128 (9) | 0.0114 (8) | 0.0014 (6) | −0.0001 (7) | −0.0021 (6) |
C4 | 0.0121 (9) | 0.0140 (9) | 0.0115 (8) | 0.0001 (7) | −0.0017 (7) | −0.0028 (6) |
C5 | 0.0147 (10) | 0.0125 (9) | 0.0107 (8) | 0.0011 (7) | −0.0014 (7) | −0.0030 (6) |
C6 | 0.0154 (10) | 0.0111 (9) | 0.0090 (7) | 0.0012 (7) | 0.0008 (7) | −0.0012 (6) |
C7 | 0.0097 (8) | 0.0091 (8) | 0.0079 (7) | 0.0013 (6) | 0.0016 (6) | 0.0002 (6) |
C8 | 0.0105 (8) | 0.0113 (9) | 0.0121 (8) | −0.0006 (6) | 0.0014 (7) | 0.0017 (6) |
C9 | 0.0087 (8) | 0.0119 (9) | 0.0137 (9) | −0.0007 (6) | 0.0011 (7) | 0.0014 (6) |
C10 | 0.0092 (8) | 0.0085 (8) | 0.0102 (8) | 0.0022 (6) | −0.0007 (7) | −0.0003 (6) |
C11 | 0.0101 (8) | 0.0125 (9) | 0.0141 (8) | 0.0028 (7) | −0.0029 (7) | −0.0010 (7) |
C12 | 0.0136 (9) | 0.0113 (9) | 0.0127 (8) | 0.0029 (7) | −0.0045 (7) | −0.0010 (6) |
C13 | 0.0169 (10) | 0.0130 (9) | 0.0102 (8) | 0.0022 (7) | −0.0017 (7) | 0.0012 (6) |
C14 | 0.0136 (9) | 0.0129 (9) | 0.0099 (8) | 0.0022 (7) | 0.0002 (7) | 0.0009 (6) |
C15 | 0.0092 (8) | 0.0096 (8) | 0.0078 (7) | 0.0028 (6) | −0.0001 (6) | −0.0005 (5) |
H1A | 0.027 (3) | 0.032 (3) | 0.028 (2) | 0.011 (2) | −0.012 (2) | −0.0088 (19) |
H1B | 0.025 (2) | 0.018 (2) | 0.026 (2) | 0.0079 (16) | −0.0015 (19) | −0.0067 (16) |
H3 | 0.024 (3) | 0.038 (3) | 0.026 (2) | −0.001 (2) | 0.007 (2) | −0.007 (2) |
H4 | 0.022 (3) | 0.037 (3) | 0.032 (3) | −0.010 (2) | −0.001 (2) | −0.005 (2) |
H5 | 0.038 (3) | 0.033 (3) | 0.022 (2) | −0.004 (2) | −0.003 (2) | −0.0105 (19) |
H6 | 0.029 (3) | 0.038 (3) | 0.021 (2) | −0.002 (2) | 0.010 (2) | −0.008 (2) |
H8 | 0.031 (3) | 0.041 (3) | 0.020 (2) | −0.010 (2) | 0.005 (2) | 0.004 (2) |
H9 | 0.020 (2) | 0.031 (3) | 0.032 (3) | −0.0084 (19) | 0.000 (2) | 0.006 (2) |
H11 | 0.015 (2) | 0.043 (3) | 0.034 (3) | 0.002 (2) | 0.000 (2) | 0.003 (2) |
H12 | 0.029 (3) | 0.030 (3) | 0.030 (3) | 0.005 (2) | −0.013 (2) | 0.0048 (19) |
H13 | 0.036 (3) | 0.041 (3) | 0.019 (2) | 0.003 (2) | 0.000 (2) | 0.011 (2) |
H14 | 0.022 (2) | 0.037 (3) | 0.027 (2) | 0.001 (2) | 0.003 (2) | 0.004 (2) |
O1—C1 | 1.239 (3) | C6—C7 | 1.410 (3) |
N1—H1A | 1.000 (5) | C7—C8 | 1.465 (3) |
N1—H1B | 1.024 (5) | C8—H8 | 1.094 (7) |
N1—C1 | 1.361 (2) | C8—C9 | 1.353 (3) |
N2—C1 | 1.385 (3) | C9—H9 | 1.088 (6) |
N2—C2 | 1.432 (2) | C9—C10 | 1.467 (3) |
N2—C15 | 1.436 (2) | C10—C15 | 1.407 (3) |
C2—C3 | 1.399 (3) | C10—C11 | 1.410 (2) |
C2—C7 | 1.406 (3) | C11—H11 | 1.089 (7) |
C3—H3 | 1.089 (7) | C11—C12 | 1.389 (4) |
C3—C4 | 1.394 (3) | C12—H12 | 1.092 (5) |
C4—H4 | 1.086 (6) | C12—C13 | 1.397 (4) |
C4—C5 | 1.399 (4) | C13—H13 | 1.089 (6) |
C5—H5 | 1.092 (5) | C13—C14 | 1.396 (3) |
C5—C6 | 1.389 (3) | C14—H14 | 1.088 (7) |
C6—H6 | 1.088 (7) | C14—C15 | 1.399 (3) |
H1A—N1—H1B | 120.3 (4) | C6—C7—C8 | 118.5 (2) |
H1A—N1—C1 | 121.2 (4) | H8—C8—C9 | 116.9 (4) |
H1B—N1—C1 | 118.5 (3) | H8—C8—C7 | 114.9 (3) |
C1—N2—C2 | 120.81 (13) | C9—C8—C7 | 128.0 (2) |
C1—N2—C15 | 121.66 (14) | H9—C9—C8 | 118.2 (4) |
C2—N2—C15 | 117.18 (15) | H9—C9—C10 | 115.4 (3) |
O1—C1—N1 | 122.4 (2) | C8—C9—C10 | 126.1 (2) |
O1—C1—N2 | 121.66 (19) | C15—C10—C11 | 117.7 (2) |
N1—C1—N2 | 115.92 (15) | C15—C10—C9 | 123.14 (17) |
C3—C2—C7 | 120.33 (18) | C11—C10—C9 | 119.1 (2) |
C3—C2—N2 | 120.3 (2) | H11—C11—C12 | 119.6 (4) |
C7—C2—N2 | 119.41 (17) | H11—C11—C10 | 119.1 (4) |
H3—C3—C4 | 120.1 (4) | C12—C11—C10 | 121.4 (2) |
H3—C3—C2 | 119.4 (3) | H12—C12—C11 | 120.2 (5) |
C4—C3—C2 | 120.5 (2) | H12—C12—C13 | 119.6 (5) |
H4—C4—C3 | 119.7 (4) | C11—C12—C13 | 120.15 (17) |
H4—C4—C5 | 120.4 (4) | H13—C13—C14 | 121.5 (4) |
C3—C4—C5 | 119.9 (2) | H13—C13—C12 | 118.9 (4) |
H5—C5—C6 | 120.1 (4) | C14—C13—C12 | 119.6 (2) |
H5—C5—C4 | 120.3 (4) | H14—C14—C13 | 121.3 (4) |
C6—C5—C4 | 119.60 (19) | H14—C14—C15 | 118.4 (3) |
H6—C6—C5 | 119.7 (4) | C13—C14—C15 | 120.2 (2) |
H6—C6—C7 | 118.8 (4) | C14—C15—C10 | 120.94 (17) |
C5—C6—C7 | 121.5 (2) | C14—C15—N2 | 119.3 (2) |
C2—C7—C6 | 118.18 (19) | C10—C15—N2 | 119.70 (18) |
C2—C7—C8 | 123.33 (18) | ||
H1A—N1—C1—O1 | −178.1 (6) | C2—C7—C8—C9 | 32.0 (3) |
H1B—N1—C1—O1 | −0.5 (6) | C6—C7—C8—C9 | −148.0 (2) |
H1A—N1—C1—N2 | 1.9 (6) | H8—C8—C9—H9 | 0.9 (7) |
H1B—N1—C1—N2 | 179.6 (5) | C7—C8—C9—H9 | 174.8 (4) |
C2—N2—C1—O1 | 9.3 (4) | H8—C8—C9—C10 | −172.0 (5) |
C15—N2—C1—O1 | −177.7 (3) | C7—C8—C9—C10 | 1.9 (4) |
C2—N2—C1—N1 | −170.7 (2) | H9—C9—C10—C15 | 155.9 (4) |
C15—N2—C1—N1 | 2.3 (3) | C8—C9—C10—C15 | −31.0 (3) |
C1—N2—C2—C3 | −71.4 (3) | H9—C9—C10—C11 | −25.6 (5) |
C15—N2—C2—C3 | 115.3 (2) | C8—C9—C10—C11 | 147.5 (2) |
C1—N2—C2—C7 | 109.5 (2) | C15—C10—C11—H11 | −177.8 (5) |
C15—N2—C2—C7 | −63.8 (2) | C9—C10—C11—H11 | 3.6 (5) |
C7—C2—C3—H3 | 179.1 (4) | C15—C10—C11—C12 | 1.2 (3) |
N2—C2—C3—H3 | 0.0 (5) | C9—C10—C11—C12 | −177.4 (2) |
C7—C2—C3—C4 | −1.4 (3) | H11—C11—C12—H12 | 0.0 (7) |
N2—C2—C3—C4 | 179.52 (19) | C10—C11—C12—H12 | −179.0 (4) |
H3—C3—C4—H4 | 0.1 (7) | H11—C11—C12—C13 | 179.1 (5) |
C2—C3—C4—H4 | −179.5 (4) | C10—C11—C12—C13 | 0.1 (3) |
H3—C3—C4—C5 | −179.7 (4) | H12—C12—C13—H13 | 0.9 (7) |
C2—C3—C4—C5 | 0.7 (3) | C11—C12—C13—H13 | −178.2 (5) |
H4—C4—C5—H5 | −1.1 (7) | H12—C12—C13—C14 | 179.0 (4) |
C3—C4—C5—H5 | 178.7 (4) | C11—C12—C13—C14 | −0.1 (3) |
H4—C4—C5—C6 | 179.8 (5) | H13—C13—C14—H14 | −1.3 (7) |
C3—C4—C5—C6 | −0.4 (3) | C12—C13—C14—H14 | −179.4 (5) |
H5—C5—C6—H6 | 0.5 (7) | H13—C13—C14—C15 | 176.8 (5) |
C4—C5—C6—H6 | 179.7 (4) | C12—C13—C14—C15 | −1.3 (3) |
H5—C5—C6—C7 | −178.4 (4) | H14—C14—C15—C10 | −179.2 (4) |
C4—C5—C6—C7 | 0.7 (3) | C13—C14—C15—C10 | 2.7 (3) |
C3—C2—C7—C6 | 1.7 (3) | H14—C14—C15—N2 | 3.9 (5) |
N2—C2—C7—C6 | −179.23 (17) | C13—C14—C15—N2 | −174.3 (2) |
C3—C2—C7—C8 | −178.32 (19) | C11—C10—C15—C14 | −2.5 (3) |
N2—C2—C7—C8 | 0.8 (3) | C9—C10—C15—C14 | 175.9 (2) |
H6—C6—C7—C2 | 179.7 (4) | C11—C10—C15—N2 | 174.38 (19) |
C5—C6—C7—C2 | −1.4 (3) | C9—C10—C15—N2 | −7.1 (3) |
H6—C6—C7—C8 | −0.3 (5) | C1—N2—C15—C14 | 72.3 (3) |
C5—C6—C7—C8 | 178.6 (2) | C2—N2—C15—C14 | −114.4 (2) |
C2—C7—C8—H8 | −154.0 (5) | C1—N2—C15—C10 | −104.7 (2) |
C6—C7—C8—H8 | 26.0 (5) | C2—N2—C15—C10 | 68.6 (2) |
C15H12N2O | F(000) = 496 |
Mr = 236.27 | Dx = 1.382 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 9544 reflections |
a = 7.4893 (4) Å | θ = 6.5–57.5° |
b = 11.0323 (5) Å | µ = 0.09 mm−1 |
c = 13.7640 (6) Å | T = 100 K |
β = 92.953 (2)° | Prism, colourless |
V = 1135.73 (9) Å3 | 0.56 × 0.35 × 0.13 mm |
Z = 4 |
Bruker APEX-II diffractometer | 16012 independent reflections |
Radiation source: sealed x-ray tube | 12833 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.06 |
φ or ω oscillation scans | θmax = 58.0°, θmin = 2.4° |
Absorption correction: multi-scan SADABS2008/1 - Bruker AXS area detector scaling and absorption correction | h = −12→17 |
Tmin = 0.695, Tmax = 0.751 | k = −26→25 |
245434 measured reflections | l = −32→32 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: structure-invariant direct methods |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: mixed |
wR(F2) = 0.130 | Only H-atom displacement parameters refined |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0804P)2 + 0.0415P] where P = (Fo2 + 2Fc2)/3 |
16012 reflections | (Δ/σ)max = 0.003 |
181 parameters | Δρmax = 0.73 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
0 constraints |
C15H12N2O | V = 1135.73 (9) Å3 |
Mr = 236.27 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.4893 (4) Å | µ = 0.09 mm−1 |
b = 11.0323 (5) Å | T = 100 K |
c = 13.7640 (6) Å | 0.56 × 0.35 × 0.13 mm |
β = 92.953 (2)° |
Bruker APEX-II diffractometer | 16012 independent reflections |
Absorption correction: multi-scan SADABS2008/1 - Bruker AXS area detector scaling and absorption correction | 12833 reflections with I > 2σ(I) |
Tmin = 0.695, Tmax = 0.751 | Rint = 0.06 |
245434 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.130 | Only H-atom displacement parameters refined |
S = 1.04 | Δρmax = 0.73 e Å−3 |
16012 reflections | Δρmin = −0.32 e Å−3 |
181 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.50994 (3) | 0.37543 (2) | 1.09386 (2) | 0.01311 (3) | |
N1 | 0.31930 (4) | 0.39948 (2) | 0.96130 (2) | 0.01521 (4) | |
N2 | 0.29416 (3) | 0.23184 (2) | 1.06195 (2) | 0.01104 (3) | |
C1 | 0.38163 (3) | 0.33847 (2) | 1.04159 (2) | 0.00998 (3) | |
C2 | 0.33099 (3) | 0.16932 (2) | 1.15184 (2) | 0.01019 (3) | |
C3 | 0.49366 (4) | 0.10930 (3) | 1.16891 (2) | 0.01276 (4) | |
H3 | 0.5797 | 0.1096 | 1.1206 | 0.025 (2)* | |
C4 | 0.53020 (4) | 0.04897 (3) | 1.25661 (2) | 0.01434 (4) | |
H4 | 0.6414 | 0.0088 | 1.2682 | 0.030 (2)* | |
C5 | 0.40330 (4) | 0.04762 (3) | 1.32748 (2) | 0.01424 (4) | |
H5 | 0.4278 | 0.0064 | 1.3873 | 0.024 (2)* | |
C6 | 0.24127 (4) | 0.10677 (3) | 1.31015 (2) | 0.01303 (4) | |
H6 | 0.1558 | 0.1061 | 1.3588 | 0.023 (2)* | |
C7 | 0.20087 (3) | 0.16776 (2) | 1.22187 (2) | 0.01073 (3) | |
C8 | 0.02601 (4) | 0.22606 (3) | 1.20782 (2) | 0.01312 (4) | |
H8 | −0.0241 | 0.2574 | 1.2647 | 0.037 (3)* | |
C9 | −0.07282 (4) | 0.24071 (3) | 1.12371 (2) | 0.01324 (4) | |
H9 | −0.1827 | 0.2831 | 1.1273 | 0.032 (3)* | |
C10 | −0.02683 (3) | 0.19751 (2) | 1.02774 (2) | 0.01141 (3) | |
C11 | −0.16462 (4) | 0.16194 (3) | 0.96038 (2) | 0.01386 (4) | |
H11 | −0.2855 | 0.1697 | 0.9773 | 0.026 (2)* | |
C12 | −0.12771 (4) | 0.11581 (3) | 0.86979 (2) | 0.01492 (4) | |
H12 | −0.223 | 0.0927 | 0.8254 | 0.022 (2)* | |
C13 | 0.04913 (5) | 0.10330 (3) | 0.84371 (2) | 0.01537 (4) | |
H13 | 0.0746 | 0.0714 | 0.7818 | 0.032 (2)* | |
C14 | 0.18778 (4) | 0.13799 (3) | 0.90915 (2) | 0.01356 (4) | |
H14 | 0.3084 | 0.1284 | 0.8923 | 0.022 (2)* | |
C15 | 0.15026 (3) | 0.18689 (2) | 0.99958 (2) | 0.01074 (3) | |
H1A | 0.2310 (14) | 0.3697 (10) | 0.9264 (8) | 0.026 (2)* | |
H1B | 0.3720 (13) | 0.4664 (9) | 0.9467 (7) | 0.023 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.01207 (6) | 0.01238 (6) | 0.01457 (7) | −0.00388 (5) | −0.00244 (5) | 0.00225 (5) |
N1 | 0.01620 (8) | 0.01360 (8) | 0.01532 (8) | −0.00518 (6) | −0.00420 (6) | 0.00575 (6) |
N2 | 0.01183 (6) | 0.01111 (6) | 0.01006 (6) | −0.00397 (5) | −0.00071 (5) | 0.00239 (5) |
C1 | 0.00967 (6) | 0.00948 (6) | 0.01080 (7) | −0.00157 (5) | 0.00068 (5) | 0.00134 (5) |
C2 | 0.01098 (7) | 0.00992 (7) | 0.00967 (6) | −0.00190 (5) | 0.00066 (5) | 0.00120 (5) |
C3 | 0.01136 (7) | 0.01443 (8) | 0.01253 (8) | −0.00054 (6) | 0.00095 (6) | 0.00216 (6) |
C4 | 0.01407 (8) | 0.01499 (9) | 0.01377 (8) | 0.00041 (7) | −0.00096 (6) | 0.00247 (7) |
C5 | 0.01771 (9) | 0.01362 (8) | 0.01126 (8) | −0.00096 (7) | −0.00050 (6) | 0.00236 (6) |
C6 | 0.01626 (9) | 0.01295 (8) | 0.01002 (7) | −0.00141 (6) | 0.00196 (6) | 0.00089 (6) |
C7 | 0.01241 (7) | 0.01023 (7) | 0.00965 (7) | −0.00110 (5) | 0.00146 (5) | −0.00002 (5) |
C8 | 0.01362 (8) | 0.01356 (8) | 0.01234 (8) | 0.00073 (6) | 0.00210 (6) | −0.00165 (6) |
C9 | 0.01210 (8) | 0.01306 (8) | 0.01460 (8) | 0.00043 (6) | 0.00090 (6) | −0.00092 (6) |
C10 | 0.01127 (7) | 0.01071 (7) | 0.01215 (7) | −0.00170 (5) | −0.00043 (5) | 0.00052 (5) |
C11 | 0.01249 (8) | 0.01392 (8) | 0.01486 (9) | −0.00262 (6) | −0.00230 (6) | 0.00115 (7) |
C12 | 0.01719 (9) | 0.01271 (8) | 0.01433 (9) | −0.00306 (7) | −0.00421 (7) | 0.00031 (7) |
C13 | 0.01934 (10) | 0.01455 (9) | 0.01200 (8) | −0.00217 (7) | −0.00144 (7) | −0.00143 (7) |
C14 | 0.01523 (8) | 0.01437 (9) | 0.01110 (7) | −0.00213 (7) | 0.00091 (6) | −0.00066 (6) |
C15 | 0.01150 (7) | 0.01046 (7) | 0.01019 (7) | −0.00267 (5) | −0.00014 (5) | 0.00070 (5) |
O1—C1 | 1.2394 (3) | C6—H6 | 0.95 |
N1—C1 | 1.3561 (3) | C7—C8 | 1.4628 (4) |
N1—H1A | 0.862 (10) | C8—C9 | 1.3513 (4) |
N1—H1B | 0.865 (10) | C8—H8 | 0.95 |
N2—C1 | 1.3822 (3) | C9—C10 | 1.4621 (4) |
N2—C2 | 1.4308 (3) | C9—H9 | 0.95 |
N2—C15 | 1.4314 (3) | C10—C15 | 1.4057 (4) |
C2—C3 | 1.3959 (4) | C10—C11 | 1.4071 (4) |
C2—C7 | 1.4057 (4) | C11—C12 | 1.3876 (5) |
C3—C4 | 1.3931 (4) | C11—H11 | 0.95 |
C3—H3 | 0.95 | C12—C13 | 1.3968 (5) |
C4—C5 | 1.3966 (4) | C12—H12 | 0.95 |
C4—H4 | 0.95 | C13—C14 | 1.3928 (4) |
C5—C6 | 1.3876 (4) | C13—H13 | 0.95 |
C5—H5 | 0.95 | C14—C15 | 1.3983 (4) |
C6—C7 | 1.4081 (4) | C14—H14 | 0.95 |
C1—N1—H1A | 119.1 (7) | C6—C7—C8 | 118.38 (2) |
C1—N1—H1B | 118.1 (6) | C9—C8—C7 | 127.81 (3) |
H1A—N1—H1B | 122.8 (10) | C9—C8—H8 | 116.1 |
C1—N2—C2 | 120.88 (2) | C7—C8—H8 | 116.1 |
C1—N2—C15 | 121.56 (2) | C8—C9—C10 | 126.22 (3) |
C2—N2—C15 | 117.21 (2) | C8—C9—H9 | 116.9 |
O1—C1—N1 | 122.27 (2) | C10—C9—H9 | 116.9 |
O1—C1—N2 | 121.58 (2) | C15—C10—C11 | 117.74 (3) |
N1—C1—N2 | 116.15 (2) | C15—C10—C9 | 123.08 (2) |
C3—C2—C7 | 120.57 (2) | C11—C10—C9 | 119.17 (2) |
C3—C2—N2 | 120.13 (2) | C12—C11—C10 | 121.40 (3) |
C7—C2—N2 | 119.29 (2) | C12—C11—H11 | 119.3 |
C4—C3—C2 | 120.22 (3) | C10—C11—H11 | 119.3 |
C4—C3—H3 | 119.9 | C11—C12—C13 | 120.17 (3) |
C2—C3—H3 | 119.9 | C11—C12—H12 | 119.9 |
C3—C4—C5 | 119.99 (3) | C13—C12—H12 | 119.9 |
C3—C4—H4 | 120 | C14—C13—C12 | 119.46 (3) |
C5—C4—H4 | 120 | C14—C13—H13 | 120.3 |
C6—C5—C4 | 119.70 (3) | C12—C13—H13 | 120.3 |
C6—C5—H5 | 120.1 | C13—C14—C15 | 120.29 (3) |
C4—C5—H5 | 120.1 | C13—C14—H14 | 119.9 |
C5—C6—C7 | 121.35 (3) | C15—C14—H14 | 119.9 |
C5—C6—H6 | 119.3 | C14—C15—C10 | 120.89 (2) |
C7—C6—H6 | 119.3 | C14—C15—N2 | 119.20 (2) |
C2—C7—C6 | 118.15 (2) | C10—C15—N2 | 119.85 (2) |
C2—C7—C8 | 123.47 (2) | ||
C2—N2—C1—O1 | 9.38 (4) | C6—C7—C8—C9 | −147.91 (3) |
C15—N2—C1—O1 | −177.64 (3) | C7—C8—C9—C10 | 1.85 (5) |
C2—N2—C1—N1 | −170.85 (3) | C8—C9—C10—C15 | −31.03 (4) |
C15—N2—C1—N1 | 2.12 (4) | C8—C9—C10—C11 | 147.47 (3) |
C1—N2—C2—C3 | −71.26 (3) | C15—C10—C11—C12 | 1.15 (4) |
C15—N2—C2—C3 | 115.47 (3) | C9—C10—C11—C12 | −177.43 (3) |
C1—N2—C2—C7 | 109.58 (3) | C10—C11—C12—C13 | 0.24 (5) |
C15—N2—C2—C7 | −63.69 (3) | C11—C12—C13—C14 | −0.29 (5) |
C7—C2—C3—C4 | −1.23 (4) | C12—C13—C14—C15 | −1.09 (5) |
N2—C2—C3—C4 | 179.62 (2) | C13—C14—C15—C10 | 2.55 (4) |
C2—C3—C4—C5 | 0.50 (5) | C13—C14—C15—N2 | −174.45 (3) |
C3—C4—C5—C6 | −0.14 (5) | C11—C10—C15—C14 | −2.54 (4) |
C4—C5—C6—C7 | 0.51 (4) | C9—C10—C15—C14 | 175.99 (3) |
C3—C2—C7—C6 | 1.55 (4) | C11—C10—C15—N2 | 174.44 (2) |
N2—C2—C7—C6 | −179.29 (2) | C9—C10—C15—N2 | −7.03 (4) |
C3—C2—C7—C8 | −178.42 (3) | C1—N2—C15—C14 | 72.27 (4) |
N2—C2—C7—C8 | 0.73 (4) | C2—N2—C15—C14 | −114.51 (3) |
C5—C6—C7—C2 | −1.20 (4) | C1—N2—C15—C10 | −104.76 (3) |
C5—C6—C7—C8 | 178.78 (3) | C2—N2—C15—C10 | 68.46 (3) |
C2—C7—C8—C9 | 32.07 (4) |
C15H12N2O | F(000) = 496 |
Mr = 236.27 | Dx = 1.382 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.4893 (4) Å | Cell parameters from 9544 reflections |
b = 11.0323 (5) Å | θ = 6.5–57.5° |
c = 13.7640 (6) Å | µ = 0.09 mm−1 |
β = 92.953 (2)° | T = 100 K |
V = 1135.73 (9) Å3 | Prism, colourless |
Z = 4 | 0.56 × 0.35 × 0.13 mm |
Bruker APEX-II diffractometer | 16012 independent reflections |
Radiation source: sealed x-ray tube | 12833 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.06 |
φ or ω oscillation scans | θmax = 58.0°, θmin = 2.4° |
Absorption correction: multi-scan SADABS2008/1 - Bruker AXS area detector scaling and absorption correction | h = −12→17 |
Tmin = 0.695, Tmax = 0.751 | k = −26→25 |
245434 measured reflections | l = −32→32 |
Refinement on F | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: structure-invariant direct methods |
R[F2 > 2σ(F2)] = 0.024 | Hydrogen site location: mixed |
wR(F2) = 0.028 | w1 = 1/[s2(Fo)] |
S = 1.42 | (Δ/σ)max < 0.001 |
13153 reflections | Δρmax = 0.25 e Å−3 |
510 parameters | Δρmin = −0.21 e Å−3 |
0 restraints |
C15H12N2O | V = 1135.73 (9) Å3 |
Mr = 236.27 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.4893 (4) Å | µ = 0.09 mm−1 |
b = 11.0323 (5) Å | T = 100 K |
c = 13.7640 (6) Å | 0.56 × 0.35 × 0.13 mm |
β = 92.953 (2)° |
Bruker APEX-II diffractometer | 16012 independent reflections |
Absorption correction: multi-scan SADABS2008/1 - Bruker AXS area detector scaling and absorption correction | 12833 reflections with I > 2σ(I) |
Tmin = 0.695, Tmax = 0.751 | Rint = 0.06 |
245434 measured reflections |
R[F2 > 2σ(F2)] = 0.024 | 510 parameters |
wR(F2) = 0.028 | 0 restraints |
S = 1.42 | Δρmax = 0.25 e Å−3 |
13153 reflections | Δρmin = −0.21 e Å−3 |
x | y | z | Uiso*/Ueq | ||
O(1) | −0.00982 (3) | 0.375434 (18) | 0.406139 (15) | 0.013 | |
N(1) | 0.18065 (3) | 0.399447 (18) | 0.538781 (15) | 0.015 | |
N(2) | 0.20584 (2) | 0.231824 (15) | 0.438050 (12) | 0.011 | |
C(1) | 0.11839 (2) | 0.338467 (14) | 0.458384 (12) | 0.009 | |
C(2) | 0.16906 (2) | 0.169362 (15) | 0.348210 (12) | 0.01 | |
C(3) | 0.00633 (2) | 0.109291 (18) | 0.331111 (14) | 0.012 | |
C(4) | −0.03032 (3) | 0.048996 (19) | 0.243423 (15) | 0.014 | |
C(5) | 0.09673 (3) | 0.047560 (18) | 0.172512 (14) | 0.014 | |
C(6) | 0.25886 (3) | 0.106779 (17) | 0.189839 (13) | 0.013 | |
C(7) | 0.29913 (2) | 0.167748 (15) | 0.278124 (12) | 0.01 | |
C(8) | 0.47400 (3) | 0.226057 (18) | 0.292115 (14) | 0.013 | |
C(9) | 0.57278 (2) | 0.240732 (18) | 0.376301 (15) | 0.013 | |
C(10) | 0.52682 (2) | 0.197503 (16) | 0.472258 (13) | 0.011 | |
C(11) | 0.66461 (3) | 0.161959 (18) | 0.539548 (15) | 0.013 | |
C(12) | 0.62777 (3) | 0.115779 (18) | 0.630200 (16) | 0.014 | |
C(13) | 0.45088 (3) | 0.103287 (19) | 0.656277 (15) | 0.015 | |
C(14) | 0.31217 (3) | 0.137963 (18) | 0.590802 (14) | 0.013 | |
C(15) | 0.34973 (2) | 0.186896 (15) | 0.500370 (12) | 0.01 | |
H(1A) | 0.282929 | 0.365151 | 0.579238 | 0.03 | |
H(1B) | 0.117752 | 0.477852 | 0.555793 | 0.023 | |
H(3) | −0.088736 | 0.112748 | 0.388211 | 0.03 | |
H(4) | −0.1543 | 0.000428 | 0.229263 | 0.03 | |
H(5) | 0.068861 | −0.001679 | 0.105195 | 0.031 | |
H(6) | 0.357378 | 0.103647 | 0.134395 | 0.029 | |
H(9) | 0.706604 | 0.278163 | 0.373974 | 0.028 | |
H(11) | 0.803149 | 0.177502 | 0.523069 | 0.031 | |
H(12) | 0.735214 | 0.09037 | 0.682572 | 0.031 | |
H(13) | 0.423956 | 0.06697 | 0.727064 | 0.031 | |
H(14) | 0.187536 | 0.127714 | 0.606589 | 0.028 | |
H(8) | 0.523722 | 0.255447 | 0.222324 | 0.031 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O(1) | 0.01198 (6) | 0.01160 (6) | 0.01428 (6) | 0.00400 (5) | −0.00242 (5) | −0.00257 (5) |
N(1) | 0.01583 (6) | 0.01303 (6) | 0.01493 (6) | 0.00527 (5) | −0.00424 (5) | −0.00576 (5) |
N(2) | 0.01142 (5) | 0.01054 (5) | 0.00965 (5) | 0.00393 (4) | −0.00068 (4) | −0.00236 (4) |
C(1) | 0.00915 (4) | 0.00895 (4) | 0.01018 (5) | 0.00181 (3) | 0.00038 (3) | −0.00145 (4) |
C(2) | 0.01035 (5) | 0.00952 (5) | 0.00923 (5) | 0.00176 (4) | 0.00070 (4) | −0.00127 (4) |
C(3) | 0.01073 (5) | 0.01403 (6) | 0.01200 (5) | 0.00048 (4) | 0.00095 (4) | −0.00232 (5) |
C(4) | 0.01360 (6) | 0.01459 (6) | 0.01309 (6) | −0.00052 (5) | −0.00091 (5) | −0.00267 (5) |
C(5) | 0.01703 (7) | 0.01314 (6) | 0.01070 (5) | 0.00069 (5) | −0.00041 (5) | −0.00249 (5) |
C(6) | 0.01567 (6) | 0.01264 (6) | 0.00936 (5) | 0.00117 (5) | 0.00194 (4) | −0.00111 (4) |
C(7) | 0.01190 (5) | 0.00985 (5) | 0.00906 (5) | 0.00100 (4) | 0.00147 (4) | −0.00014 (4) |
C(8) | 0.01311 (6) | 0.01320 (6) | 0.01169 (6) | −0.00089 (4) | 0.00194 (4) | 0.00173 (5) |
C(9) | 0.01159 (5) | 0.01285 (6) | 0.01377 (6) | −0.00055 (4) | 0.00075 (4) | 0.00098 (5) |
C(10) | 0.01060 (5) | 0.01036 (5) | 0.01158 (5) | 0.00176 (4) | −0.00048 (4) | −0.00040 (4) |
C(11) | 0.01187 (6) | 0.01362 (6) | 0.01411 (6) | 0.00255 (5) | −0.00232 (5) | −0.00085 (5) |
C(12) | 0.01647 (7) | 0.01251 (6) | 0.01368 (6) | 0.00313 (5) | −0.00409 (5) | −0.00012 (5) |
C(13) | 0.01855 (7) | 0.01433 (6) | 0.01145 (6) | 0.00221 (5) | −0.00151 (5) | 0.00164 (5) |
C(14) | 0.01450 (6) | 0.01414 (6) | 0.01053 (5) | 0.00215 (5) | 0.00081 (4) | 0.00084 (5) |
C(15) | 0.01092 (5) | 0.01013 (5) | 0.00957 (5) | 0.00261 (4) | −0.00001 (4) | −0.00053 (4) |
H(1A) | 0.029922 | 0.030996 | 0.028278 | 0.008936 | −0.012008 | −0.006465 |
H(1B) | 0.025218 | 0.019634 | 0.025237 | 0.006451 | −0.000188 | −0.006538 |
H(3) | 0.023428 | 0.040889 | 0.02615 | −0.001751 | 0.007119 | −0.007378 |
H(4) | 0.025218 | 0.03296 | 0.032033 | −0.009223 | −0.001394 | −0.005679 |
H(5) | 0.035101 | 0.033636 | 0.023035 | −0.003076 | −0.001677 | −0.009982 |
H(6) | 0.026625 | 0.039528 | 0.0214 | −0.002235 | 0.011713 | −0.007305 |
H(9) | 0.01929 | 0.033983 | 0.03153 | −0.007159 | 0.001876 | 0.003701 |
H(11) | 0.018952 | 0.041893 | 0.032042 | 0.003218 | −0.000983 | 0.003199 |
H(12) | 0.029246 | 0.031654 | 0.030251 | 0.004323 | −0.012638 | 0.004633 |
H(13) | 0.032754 | 0.038779 | 0.021145 | 0.001784 | 0.00046 | 0.010041 |
H(14) | 0.023519 | 0.034139 | 0.026452 | 0.002944 | 0.004251 | 0.00509 |
H(8) | 0.031539 | 0.03929 | 0.02204 | −0.010794 | 0.004771 | 0.003135 |
O(1)—C(1) | 1.2387 (2) | C(6)—H(6) | 1.0890 (2) |
N(1)—C(1) | 1.3570 (2) | C(7)—C(8) | 1.4629 (3) |
N(1)—H(1A) | 0.9980 (2) | C(8)—C(9) | 1.3520 (3) |
N(1)—H(1B) | 1.0180 (2) | C(8)—H(8) | 1.0970 (2) |
N(2)—C(1) | 1.3821 (2) | C(9)—C(10) | 1.4619 (3) |
N(2)—C(2) | 1.4299 (2) | C(9)—H(9) | 1.0860 (2) |
N(2)—C(15) | 1.4309 (2) | C(10)—C(11) | 1.4064 (2) |
C(2)—C(3) | 1.3965 (2) | C(10)—C(15) | 1.4055 (2) |
C(2)—C(7) | 1.4059 (2) | C(11)—C(12) | 1.3885 (3) |
C(3)—C(4) | 1.3930 (3) | C(11)—H(11) | 1.0870 (2) |
C(3)—H(3) | 1.0880 (2) | C(12)—C(13) | 1.3971 (3) |
C(4)—C(5) | 1.3978 (3) | C(12)—H(12) | 1.0890 (2) |
C(4)—H(4) | 1.0810 (2) | C(13)—C(14) | 1.3933 (3) |
C(5)—C(6) | 1.3887 (3) | C(13)—H(13) | 1.0820 (2) |
C(5)—H(5) | 1.0850 (2) | C(14)—C(15) | 1.3985 (3) |
C(6)—C(7) | 1.4079 (2) | C(14)—H(14) | 0.9758 (2) |
C(1)—N(1)—H(1A) | 119.253 (17) | C(6)—C(7)—C(8) | 118.305 (16) |
C(1)—N(1)—H(1B) | 117.721 (16) | C(7)—C(8)—C(9) | 127.741 (17) |
H(1A)—N(1)—H(1B) | 123.008 (17) | C(7)—C(8)—H(8) | 110.896 (16) |
C(1)—N(2)—C(2) | 120.874 (14) | C(9)—C(8)—H(8) | 121.310 (18) |
C(1)—N(2)—C(15) | 121.571 (15) | C(8)—C(9)—C(10) | 126.254 (17) |
C(2)—N(2)—C(15) | 117.196 (14) | C(8)—C(9)—H(9) | 119.034 (19) |
O(1)—C(1)—N(1) | 122.258 (17) | C(10)—C(9)—H(9) | 114.285 (16) |
O(1)—C(1)—N(2) | 121.597 (16) | C(9)—C(10)—C(11) | 119.145 (17) |
N(1)—C(1)—N(2) | 116.144 (15) | C(9)—C(10)—C(15) | 123.045 (15) |
N(2)—C(2)—C(3) | 120.132 (16) | C(11)—C(10)—C(15) | 117.794 (17) |
N(2)—C(2)—C(7) | 119.343 (15) | C(10)—C(11)—C(12) | 121.402 (19) |
C(3)—C(2)—C(7) | 120.520 (15) | C(10)—C(11)—H(11) | 119.634 (19) |
C(2)—C(3)—C(4) | 120.262 (18) | C(12)—C(11)—H(11) | 118.775 (17) |
C(2)—C(3)—H(3) | 117.355 (16) | C(11)—C(12)—C(13) | 120.132 (17) |
C(4)—C(3)—H(3) | 122.380 (17) | C(11)—C(12)—H(12) | 121.00 (2) |
C(3)—C(4)—C(5) | 119.969 (18) | C(13)—C(12)—H(12) | 118.86 (2) |
C(3)—C(4)—H(4) | 121.47 (2) | C(12)—C(13)—C(14) | 119.475 (19) |
C(5)—C(4)—H(4) | 118.539 (18) | C(12)—C(13)—H(13) | 119.408 (18) |
C(4)—C(5)—C(6) | 119.698 (17) | C(14)—C(13)—H(13) | 121.12 (2) |
C(4)—C(5)—H(5) | 119.606 (19) | C(13)—C(14)—C(15) | 120.279 (19) |
C(6)—C(5)—H(5) | 120.680 (19) | C(13)—C(14)—H(14) | 120.934 (19) |
C(5)—C(6)—C(7) | 121.299 (18) | C(15)—C(14)—H(14) | 118.782 (17) |
C(5)—C(6)—H(6) | 118.864 (17) | N(2)—C(15)—C(10) | 119.891 (16) |
C(7)—C(6)—H(6) | 119.819 (18) | N(2)—C(15)—C(14) | 119.172 (16) |
C(2)—C(7)—C(6) | 118.235 (16) | C(10)—C(15)—C(14) | 120.868 (15) |
C(2)—C(7)—C(8) | 123.460 (16) |
Experimental details
(dihydrate_mono_NEUTRON) | (dihydrate_mono_XRAY) | (dihydrate_ortho_NEUTRON) | (dihydrate_ortho_XRAY) | |
Crystal data | ||||
Chemical formula | C15H12N2O·2(H2O) | C15H12N2O·2(H2O) | C15H12N2O·2(H2O) | C15H12N2O·2(H2O) |
Mr | 272.3 | 272.3 | 272.3 | 272.3 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/c | Orthorhombic, Cmca | Orthorhombic, Cmca |
Temperature (K) | 100 | 100 | 100 | 100 |
a, b, c (Å) | 10.116 (3), 28.856 (8), 4.8378 (16) | 10.144 (4), 28.891 (11), 4.847 (2) | 19.638 (6), 4.8378 (16), 28.856 (8) | 19.705 (8), 4.847 (2), 28.891 (11) |
α, β, γ (°) | 90, 103.908 (18), 90 | 90, 103.763 (12), 90 | 90, 90, 90 | 90, 90, 90 |
V (Å3) | 1370.7 (7) | 1379.7 (10) | 2741.5 (14) | 2759.4 (19) |
Z | 4 | 4 | 8 | 8 |
Radiation type | Neutrons, λ = 0.42 Å | Mo Kα | ?, λ = 0.4-7.97 Å | Mo Kα |
µ (mm−1) | 0 | 0.09 | 0 | 0.09 |
Crystal size (mm) | 5 × 2 × 2 | 0.4 × 0.29 × 0.18 | 8 × 2 × 2 | 0.4 × 0.29 × 0.18 |
Data collection | ||||
Diffractometer | SXD beamline | Bruker APEX-II | SXD beamline | Bruker APEX-II |
Absorption correction | – | Multi-scan SADABS2012/1 - Bruker AXS area detector scaling and absorption correction | – | Multi-scan SADABS2012/1 - Bruker AXS area detector scaling and absorption correction |
Tmin, Tmax | – | 0.648, 0.745 | – | 0.648, 0.745 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5423, 5423, 5423 | 13851, 2433, 1534 | 5374, 5374, 5374 | 11763, 1258, 903 |
Rint | ? | 0.068 | ? | 0.069 |
(sin θ/λ)max (Å−1) | 2.367 | 0.595 | – | 0.595 |
Distance from specimen to detector (mm) | – | – | h = −53→40, k = −9→5, l = −56→111 | – |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.065, 0.172, 1.10 | 0.044, 0.082, 0.99 | 0.065, 0.171, 1.07 | 0.039, 0.074, 1.01 |
No. of reflections | 5423 | 2433 | 5374 | 1258 |
No. of parameters | 365 | 214 | 188 | 119 |
No. of restraints | 0 | 10 | 0 | 4 |
H-atom treatment | All H-atom parameters refined | H atoms treated by a mixture of independent and constrained refinement | All H-atom parameters refined | Only H-atom displacement parameters refined |
w = 1/[σ2(Fo2) + (0.1101P)2 + 28.884P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0242P)2] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.1195P)2 + 83.2386P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0257P)2 + 0.5684P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 1.46, −1.34 | 0.18, −0.18 | 1.60, −1.51 | 0.19, −0.16 |
(formIII_NEUTRON) | (formIII_XRAY_shelx) | (formIII_XRAY_xd) | |
Crystal data | |||
Chemical formula | C15H12N2O | C15H12N2O | C15H12N2O |
Mr | 236.27 | 236.27 | 236.27 |
Crystal system, space group | Monoclinic, P21/n | Monoclinic, P21/n | Monoclinic, P21/n |
Temperature (K) | 100 | 100 | 100 |
a, b, c (Å) | 7.4980 (15), 11.058 (2), 13.789 (3) | 7.4893 (4), 11.0323 (5), 13.7640 (6) | 7.4893 (4), 11.0323 (5), 13.7640 (6) |
α, β, γ (°) | 90, 92.838 (16), 90 | 90, 92.953 (2), 90 | 90, 92.953 (2), 90 |
V (Å3) | 1141.9 (4) | 1135.73 (9) | 1135.73 (9) |
Z | 4 | 4 | 4 |
Radiation type | ?, λ = 0.42 Å | Mo Kα | Mo Kα |
µ (mm−1) | 0 | 0.09 | 0.09 |
Crystal size (mm) | 8 × 2 × 2 | 0.56 × 0.35 × 0.13 | 0.56 × 0.35 × 0.13 |
Data collection | |||
Diffractometer | SXD beamline | Bruker APEX-II | Bruker APEX-II |
Absorption correction | – | Multi-scan SADABS2008/1 - Bruker AXS area detector scaling and absorption correction | Multi-scan SADABS2008/1 - Bruker AXS area detector scaling and absorption correction |
Tmin, Tmax | – | 0.695, 0.751 | 0.695, 0.751 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8450, 8450, 8450 | 245434, 16012, 12833 | 245434, 16012, 12833 |
Rint | ? | 0.06 | 0.06 |
(sin θ/λ)max (Å−1) | 2.362 | 1.193 | 1.193 |
Distance from specimen to detector (mm) | – | – | – |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | 0.068, 0.164, 1.07 | 0.041, 0.130, 1.04 | 0.024, 0.028, 1.42 |
No. of reflections | 8450 | 16012 | 13153 |
No. of parameters | 276 | 181 | 510 |
No. of restraints | 0 | 0 | 0 |
H-atom treatment | All H-atom parameters refined | Only H-atom displacement parameters refined | ? |
w = 1/[σ2(Fo2) + (0.0888P)2 + 26.222P] where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.0804P)2 + 0.0415P] where P = (Fo2 + 2Fc2)/3 | w1 = 1/[s2(Fo)] | |
Δρmax, Δρmin (e Å−3) | 1.85, −2.03 | 0.73, −0.32 | 0.25, −0.21 |
Computer programs: SXD2001, Gutmann (2005), Bruker APEX2 software, SAINT V8.27B integration software, SAINT V7.68A integration software, SORTAV (Blessing, 1995), SIR92 (Altomare et al., 1994), SHELXL2013 (Sheldrick, 2013), Volkov et al., (2006), ORTEP-3 for Windows (Farrugia, 2012), WinGX publication routines (Farrugia, 2012).
O(1)—C(1) | 1.2387 (2) | C(6)—H(6) | 1.0890 (2) |
N(1)—C(1) | 1.3570 (2) | C(7)—C(8) | 1.4629 (3) |
N(1)—H(1A) | 0.9980 (2) | C(8)—C(9) | 1.3520 (3) |
N(1)—H(1B) | 1.0180 (2) | C(8)—H(8) | 1.0970 (2) |
N(2)—C(1) | 1.3821 (2) | C(9)—C(10) | 1.4619 (3) |
N(2)—C(2) | 1.4299 (2) | C(9)—H(9) | 1.0860 (2) |
N(2)—C(15) | 1.4309 (2) | C(10)—C(11) | 1.4064 (2) |
C(2)—C(3) | 1.3965 (2) | C(10)—C(15) | 1.4055 (2) |
C(2)—C(7) | 1.4059 (2) | C(11)—C(12) | 1.3885 (3) |
C(3)—C(4) | 1.3930 (3) | C(11)—H(11) | 1.0870 (2) |
C(3)—H(3) | 1.0880 (2) | C(12)—C(13) | 1.3971 (3) |
C(4)—C(5) | 1.3978 (3) | C(12)—H(12) | 1.0890 (2) |
C(4)—H(4) | 1.0810 (2) | C(13)—C(14) | 1.3933 (3) |
C(5)—C(6) | 1.3887 (3) | C(13)—H(13) | 1.0820 (2) |
C(5)—H(5) | 1.0850 (2) | C(14)—C(15) | 1.3985 (3) |
C(6)—C(7) | 1.4079 (2) | C(14)—H(14) | 0.9758 (2) |
C(1)—N(1)—H(1A) | 119.253 (17) | C(6)—C(7)—C(8) | 118.305 (16) |
C(1)—N(1)—H(1B) | 117.721 (16) | C(7)—C(8)—C(9) | 127.741 (17) |
H(1A)—N(1)—H(1B) | 123.008 (17) | C(7)—C(8)—H(8) | 110.896 (16) |
C(1)—N(2)—C(2) | 120.874 (14) | C(9)—C(8)—H(8) | 121.310 (18) |
C(1)—N(2)—C(15) | 121.571 (15) | C(8)—C(9)—C(10) | 126.254 (17) |
C(2)—N(2)—C(15) | 117.196 (14) | C(8)—C(9)—H(9) | 119.034 (19) |
O(1)—C(1)—N(1) | 122.258 (17) | C(10)—C(9)—H(9) | 114.285 (16) |
O(1)—C(1)—N(2) | 121.597 (16) | C(9)—C(10)—C(11) | 119.145 (17) |
N(1)—C(1)—N(2) | 116.144 (15) | C(9)—C(10)—C(15) | 123.045 (15) |
N(2)—C(2)—C(3) | 120.132 (16) | C(11)—C(10)—C(15) | 117.794 (17) |
N(2)—C(2)—C(7) | 119.343 (15) | C(10)—C(11)—C(12) | 121.402 (19) |
C(3)—C(2)—C(7) | 120.520 (15) | C(10)—C(11)—H(11) | 119.634 (19) |
C(2)—C(3)—C(4) | 120.262 (18) | C(12)—C(11)—H(11) | 118.775 (17) |
C(2)—C(3)—H(3) | 117.355 (16) | C(11)—C(12)—C(13) | 120.132 (17) |
C(4)—C(3)—H(3) | 122.380 (17) | C(11)—C(12)—H(12) | 121.00 (2) |
C(3)—C(4)—C(5) | 119.969 (18) | C(13)—C(12)—H(12) | 118.86 (2) |
C(3)—C(4)—H(4) | 121.47 (2) | C(12)—C(13)—C(14) | 119.475 (19) |
C(5)—C(4)—H(4) | 118.539 (18) | C(12)—C(13)—H(13) | 119.408 (18) |
C(4)—C(5)—C(6) | 119.698 (17) | C(14)—C(13)—H(13) | 121.12 (2) |
C(4)—C(5)—H(5) | 119.606 (19) | C(13)—C(14)—C(15) | 120.279 (19) |
C(6)—C(5)—H(5) | 120.680 (19) | C(13)—C(14)—H(14) | 120.934 (19) |
C(5)—C(6)—C(7) | 121.299 (18) | C(15)—C(14)—H(14) | 118.782 (17) |
C(5)—C(6)—H(6) | 118.864 (17) | N(2)—C(15)—C(10) | 119.891 (16) |
C(7)—C(6)—H(6) | 119.819 (18) | N(2)—C(15)—C(14) | 119.172 (16) |
C(2)—C(7)—C(6) | 118.235 (16) | C(10)—C(15)—C(14) | 120.868 (15) |
C(2)—C(7)—C(8) | 123.460 (16) |