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Analysis of neutron and high-resolution X-ray diffraction data on form (III) of carbamazepine at 100 K using the atoms in molecules (AIM) topological approach afforded excellent agreement between the experimental results and theoretical densities from the optimized gas-phase structure and from multipole modelling of static theoretical structure factors. The charge density analysis provides experimental confirmation of the partially localized π-bonding suggested by the conventional structural formula, but the evidence for any significant C—N π bonding is not strong. Hirshfeld atom refinement (HAR) gives H atom positional and anisotropic displacement parameters that agree very well with the neutron parameters. X-ray and neutron diffraction data on the dihydrate of carbemazepine strongly indicate a disordered orthorhombic crystal structure in the space group Cmca, rather than a monoclinic crystal structure in space group P21/c. This disorder in the dihydrate structure has implications for both experimental and theoretical studies of polymorphism.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520615019538/bi5051sup1.cif
Contains datablocks global, dihydrate_mono_NEUTRON, dihydrate_mono_XRAY, dihydrate_ortho_NEUTRON, dihydrate_ortho_XRAY, formIII_NEUTRON, formIII_XRAY_shelx, formIII_XRAY_xd

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520615019538/bi5051dihydrate_mono_NEUTRONsup2.hkl
Contains datablock dihydrate_mono_NEUTRON

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520615019538/bi5051dihydrate_mono_XRAYsup3.hkl
Contains datablock dihydrate_mono_XRAY

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520615019538/bi5051dihydrate_ortho_NEUTRONsup4.hkl
Contains datablock dihydrate_orth_NEUTRON

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520615019538/bi5051dihydrate_ortho_XRAYsup5.hkl
Contains datablock dihydrate_orth_XRAY

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520615019538/bi5051formIII_NEUTRONsup6.hkl
Contains datablock formIII_NEUTRON

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520615019538/bi5051formIII_XRAY_shelxsup7.hkl
Contains datablock formIII_XRAY_shelx

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520615019538/bi5051formIII_XRAY_xdsup8.hkl
Contains datablock formIII_XRAY_xd

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Portable Document Format (PDF) file https://doi.org/10.1107/S2052520615019538/bi5051sup9.pdf
Supporting figures and tables

CCDC references: 1027345; 1027346; 1027347; 1027348; 1027349; 1027350; 1027351

Computing details top

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.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
(dihydrate_mono_NEUTRON) top
Crystal data top
C15H12N2O·2(H2O)F(000) = 576
Mr = 272.3Dx = 1.319 Mg m3
Monoclinic, P21/cNeutrons radiation, λ = 0.42 Å
Hall symbol: -P 2ybcCell parameters from 0 reflections
a = 10.116 (3) Åθ = 0–0°
b = 28.856 (8) ŵ = 0 mm1
c = 4.8378 (16) ÅT = 100 K
β = 103.908 (18)°Prism, colourless
V = 1370.7 (7) Å35 × 2 × 2 mm
Z = 4
Data collection top
SXD beamline
diffractometer
5423 reflections with I > 2σ(I)
Radiation source: ISIS neutron spallation sourceθmax = 83.9°, θmin = 7.9°
time of flight Laue diffraction scansh = 2723
5423 measured reflectionsk = 11156
5423 independent reflectionsl = 95
Refinement top
Refinement on F2Secondary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065All 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 reflectionsΔρmax = 1.46 e Å3
365 parametersΔρmin = 1.34 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraintsExtinction coefficient: 0.00099 (8)
Primary atom site location: structure-invariant direct methods
Crystal data top
C15H12N2O·2(H2O)V = 1370.7 (7) Å3
Mr = 272.3Z = 4
Monoclinic, P21/cNeutrons radiation, λ = 0.42 Å
a = 10.116 (3) ŵ = 0 mm1
b = 28.856 (8) ÅT = 100 K
c = 4.8378 (16) Å5 × 2 × 2 mm
β = 103.908 (18)°
Data collection top
SXD beamline
diffractometer
5423 independent reflections
5423 measured reflections5423 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0650 restraints
wR(F2) = 0.172All H-atom parameters refined
S = 1.10 w = 1/[σ2(Fo2) + (0.1101P)2 + 28.884P]
where P = (Fo2 + 2Fc2)/3
5423 reflectionsΔρmax = 1.46 e Å3
365 parametersΔρmin = 1.34 e Å3
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.3839 (9)0.0478 (4)0.512 (3)0.008 (2)*0.499 (13)
N10.6161 (7)0.0476 (3)0.642 (2)0.0111 (17)*0.499 (13)
N1A0.3850 (6)0.0459 (2)0.567 (2)0.0103 (16)*0.501 (13)
O1A0.6155 (10)0.0452 (4)0.692 (3)0.008 (2)*0.501 (13)
N20.4999 (2)0.11070 (6)0.7688 (7)0.0116 (6)
C10.5002 (3)0.06669 (9)0.6577 (10)0.0115 (8)
C20.3758 (3)0.13426 (9)0.7720 (9)0.0108 (8)
C30.2902 (3)0.11659 (10)0.9343 (10)0.0127 (8)
C40.1684 (3)0.13903 (10)0.9355 (10)0.0144 (8)
C50.1325 (3)0.17927 (11)0.7734 (10)0.0135 (8)
C60.2185 (3)0.19686 (10)0.6139 (10)0.0128 (8)
C70.3427 (3)0.17510 (10)0.6111 (9)0.0106 (8)
C80.4314 (3)0.19592 (10)0.4464 (10)0.0120 (8)
C90.5689 (3)0.19592 (10)0.5138 (10)0.0118 (8)
C100.6573 (3)0.17511 (10)0.7703 (9)0.0103 (7)
C110.7817 (3)0.19683 (10)0.8949 (10)0.0123 (8)
C120.8677 (3)0.17926 (11)1.1422 (10)0.0135 (8)
C130.8315 (3)0.13889 (11)1.2674 (10)0.0141 (8)
C140.7098 (3)0.11667 (10)1.1446 (10)0.0130 (8)
C150.6238 (3)0.13426 (9)0.8958 (9)0.0096 (8)
H30.3207 (8)0.0855 (2)1.060 (2)0.030 (2)
H40.1030 (7)0.1250 (3)1.063 (2)0.031 (2)
H50.0364 (7)0.1966 (3)0.774 (2)0.032 (2)
H60.1911 (7)0.2284 (2)0.489 (2)0.029 (2)
H80.3798 (7)0.2162 (3)0.261 (2)0.0275 (19)
H90.6202 (7)0.2161 (3)0.380 (2)0.028 (2)
H110.8089 (7)0.2283 (2)0.800 (2)0.029 (2)
H120.9631 (6)0.1965 (3)1.236 (2)0.030 (2)
H130.8978 (7)0.1251 (3)1.459 (2)0.029 (2)
H140.6796 (7)0.0853 (2)1.241 (2)0.032 (2)
H1A0.7070 (12)0.0614 (5)0.743 (5)0.031 (5)0.499 (13)
H1B0.6136 (13)0.0129 (5)0.582 (4)0.024 (4)0.499 (13)
H1C0.2946 (12)0.0608 (5)0.539 (5)0.031 (5)0.501 (13)
H1D0.3874 (13)0.0132 (5)0.469 (4)0.025 (4)0.501 (13)
O20.0847 (6)0.04801 (17)0.3483 (16)0.0294 (14)
H2A0.0336 (11)0.0526 (3)0.493 (3)0.042 (3)
H2B0.1945 (14)0.0529 (6)0.447 (5)0.033 (5)0.499 (13)
H2C0.0792 (14)0.0162 (5)0.314 (5)0.028 (4)0.501 (13)
O30.9173 (6)0.04807 (17)0.7636 (17)0.0291 (13)
H3A0.9693 (14)0.0527 (4)0.959 (3)0.051 (3)
H3B0.9173 (15)0.0158 (5)0.726 (5)0.031 (5)0.499 (13)
H3C0.8077 (17)0.0536 (6)0.754 (5)0.035 (5)0.501 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0105 (6)0.0052 (7)0.0190 (18)0.0002 (6)0.0035 (8)0.0014 (9)
C10.0116 (9)0.0056 (9)0.018 (3)0.0005 (8)0.0038 (12)0.0009 (12)
C20.0104 (10)0.0053 (10)0.017 (2)0.0000 (8)0.0050 (11)0.0004 (13)
C30.0143 (11)0.0086 (11)0.017 (3)0.0008 (8)0.0064 (13)0.0006 (14)
C40.0123 (10)0.0128 (12)0.020 (3)0.0015 (9)0.0072 (12)0.0005 (15)
C50.0104 (10)0.0137 (12)0.018 (3)0.0009 (8)0.0053 (12)0.0007 (14)
C60.0096 (10)0.0100 (11)0.019 (3)0.0021 (8)0.0040 (12)0.0028 (14)
C70.0092 (10)0.0076 (10)0.015 (2)0.0005 (8)0.0038 (11)0.0007 (12)
C80.0090 (9)0.0103 (11)0.016 (3)0.0007 (8)0.0024 (12)0.0018 (14)
C90.0105 (10)0.0094 (11)0.016 (3)0.0007 (8)0.0036 (12)0.0003 (14)
C100.0105 (10)0.0077 (10)0.014 (2)0.0009 (8)0.0045 (11)0.0006 (12)
C110.0090 (10)0.0111 (11)0.017 (3)0.0014 (8)0.0040 (12)0.0010 (14)
C120.0092 (10)0.0128 (12)0.017 (3)0.0009 (8)0.0006 (12)0.0012 (14)
C130.0141 (11)0.0114 (12)0.016 (3)0.0013 (9)0.0013 (12)0.0013 (14)
C140.0135 (11)0.0086 (11)0.016 (3)0.0008 (8)0.0014 (12)0.0016 (13)
C150.0095 (9)0.0059 (10)0.013 (3)0.0001 (7)0.0021 (11)0.0007 (12)
H30.034 (3)0.019 (3)0.038 (7)0.002 (2)0.011 (4)0.010 (4)
H40.030 (3)0.031 (3)0.038 (7)0.003 (3)0.020 (4)0.001 (4)
H50.020 (3)0.030 (3)0.048 (7)0.006 (2)0.012 (3)0.003 (4)
H60.022 (3)0.021 (3)0.041 (7)0.006 (2)0.005 (3)0.007 (3)
H80.024 (3)0.031 (3)0.023 (6)0.004 (2)0.002 (3)0.013 (4)
H90.024 (3)0.032 (3)0.030 (6)0.002 (2)0.010 (3)0.013 (4)
H110.026 (3)0.020 (3)0.040 (7)0.007 (2)0.008 (3)0.010 (3)
H120.019 (3)0.033 (4)0.035 (7)0.007 (2)0.001 (3)0.001 (4)
H130.030 (3)0.032 (4)0.018 (6)0.004 (3)0.005 (3)0.005 (4)
H140.032 (3)0.017 (3)0.042 (8)0.006 (2)0.000 (4)0.007 (4)
H1A0.014 (5)0.026 (7)0.048 (15)0.003 (4)0.002 (6)0.012 (8)
H1B0.022 (5)0.017 (6)0.033 (13)0.002 (4)0.007 (6)0.002 (6)
H1C0.019 (5)0.016 (6)0.055 (16)0.001 (4)0.005 (6)0.007 (7)
H1D0.025 (5)0.010 (5)0.039 (13)0.003 (4)0.007 (6)0.000 (6)
O20.048 (3)0.0182 (19)0.026 (5)0.0051 (18)0.017 (3)0.003 (2)
H2A0.064 (6)0.032 (4)0.035 (9)0.002 (4)0.023 (6)0.005 (5)
H2B0.025 (6)0.025 (7)0.045 (15)0.002 (4)0.001 (7)0.004 (8)
H2C0.027 (6)0.016 (6)0.037 (14)0.003 (4)0.003 (7)0.001 (7)
O30.055 (3)0.0158 (19)0.015 (4)0.0077 (19)0.005 (3)0.002 (2)
H3A0.091 (9)0.035 (5)0.023 (10)0.005 (5)0.006 (7)0.001 (6)
H3B0.031 (6)0.021 (7)0.040 (15)0.006 (5)0.006 (7)0.007 (8)
H3C0.040 (8)0.027 (7)0.039 (16)0.002 (6)0.011 (8)0.005 (8)
Geometric parameters (Å, º) top
O1—C11.334 (11)C7—C81.464 (5)
N1—H1A1.014 (15)C8—H81.091 (10)
N1—H1B1.041 (17)C8—C91.351 (4)
N1—C11.314 (7)C9—H91.090 (8)
N1A—H1C0.990 (14)C9—C101.472 (6)
N1A—H1D1.058 (17)C10—C151.404 (4)
N1A—C11.291 (7)C10—C111.405 (4)
O1A—C11.295 (10)C11—H111.083 (8)
N2—C11.379 (3)C11—C121.394 (6)
N2—C151.429 (4)C12—H121.083 (7)
N2—C21.431 (3)C12—C131.401 (5)
C2—C31.398 (5)C13—H131.080 (10)
C2—C71.408 (4)C13—C141.389 (5)
C3—H31.085 (9)C14—H141.093 (9)
C3—C41.394 (4)C14—C151.400 (5)
C4—H41.084 (8)O2—H2C0.931 (15)
C4—C51.399 (5)O2—H2A0.975 (14)
C5—H51.094 (7)O2—H2B1.108 (16)
C5—C61.389 (5)O3—H3B0.950 (16)
C6—H61.091 (9)O3—H3A0.974 (19)
C6—C71.408 (4)O3—H3C1.110 (17)
H1A—N1—H1B118.1 (13)C2—C7—C8123.3 (2)
H1A—N1—C1121.7 (11)C6—C7—C8119.2 (3)
H1B—N1—C1117.3 (9)H8—C8—C9117.3 (5)
H1C—N1A—H1D116.4 (14)H8—C8—C7115.6 (5)
H1C—N1A—C1125.0 (11)C9—C8—C7126.8 (4)
H1D—N1A—C1116.8 (9)H9—C9—C8117.8 (5)
C1—N2—C15121.4 (2)H9—C9—C10116.1 (5)
C1—N2—C2121.8 (2)C8—C9—C10125.8 (3)
C15—N2—C2116.8 (2)C15—C10—C11118.2 (3)
N1A—C1—O1A122.1 (6)C15—C10—C9123.1 (3)
N1—C1—O1118.9 (6)C11—C10—C9118.7 (3)
N1A—C1—N2118.3 (4)H11—C11—C12120.0 (6)
O1A—C1—N2118.5 (6)H11—C11—C10118.9 (6)
N1—C1—N2119.7 (4)C12—C11—C10121.0 (3)
O1—C1—N2119.8 (5)H12—C12—C11120.0 (6)
C3—C2—C7121.3 (2)H12—C12—C13120.0 (6)
C3—C2—N2119.7 (3)C11—C12—C13119.9 (3)
C7—C2—N2119.0 (3)H13—C13—C14120.1 (5)
H3—C3—C4120.9 (5)H13—C13—C12120.2 (5)
H3—C3—C2119.0 (5)C14—C13—C12119.7 (4)
C4—C3—C2120.0 (3)H14—C14—C13120.6 (6)
H4—C4—C3119.3 (6)H14—C14—C15119.1 (6)
H4—C4—C5121.1 (5)C13—C14—C15120.3 (3)
C3—C4—C5119.6 (3)C14—C15—C10120.8 (3)
H5—C5—C6120.6 (6)C14—C15—N2119.8 (3)
H5—C5—C4119.3 (6)C10—C15—N2119.4 (3)
C6—C5—C4120.1 (2)H2C—O2—H2A104.1 (14)
H6—C6—C5120.2 (5)H2A—O2—H2B108.8 (15)
H6—C6—C7118.4 (5)H3B—O3—H3A107.1 (16)
C5—C6—C7121.4 (3)H3A—O3—H3C108.7 (16)
C2—C7—C6117.5 (3)
H1C—N1A—C1—O1A179 (2)C3—C2—C7—C8177.6 (4)
H1D—N1A—C1—O1A16.4 (18)N2—C2—C7—C82.2 (6)
H1C—N1A—C1—N1167.5 (19)H6—C6—C7—C2179.6 (7)
H1D—N1A—C1—N13.3 (17)C5—C6—C7—C21.2 (6)
H1C—N1A—C1—O190 (4)H6—C6—C7—C81.1 (8)
H1D—N1A—C1—O175 (4)C5—C6—C7—C8178.1 (4)
H1C—N1A—C1—N211 (2)C2—C7—C8—H8152.4 (7)
H1D—N1A—C1—N2175.5 (13)C6—C7—C8—H828.3 (7)
H1A—N1—C1—N1A169.3 (17)C2—C7—C8—C933.7 (6)
H1B—N1—C1—N1A9.0 (18)C6—C7—C8—C9145.5 (4)
H1A—N1—C1—O1A75 (4)H8—C8—C9—H90.0 (10)
H1B—N1—C1—O1A85 (4)C7—C8—C9—H9173.7 (7)
H1A—N1—C1—O1177.6 (17)H8—C8—C9—C10173.1 (7)
H1B—N1—C1—O122.0 (18)C7—C8—C9—C100.6 (6)
H1A—N1—C1—N211.9 (18)H9—C9—C10—C15151.8 (6)
H1B—N1—C1—N2172.2 (14)C8—C9—C10—C1534.9 (5)
C15—N2—C1—N1A174.5 (5)H9—C9—C10—C1127.6 (7)
C2—N2—C1—N1A3.2 (7)C8—C9—C10—C11145.6 (4)
C15—N2—C1—O1A5.9 (9)C15—C10—C11—H11179.7 (6)
C2—N2—C1—O1A171.8 (8)C9—C10—C11—H110.2 (7)
C15—N2—C1—N16.7 (7)C15—C10—C11—C122.2 (5)
C2—N2—C1—N1175.6 (6)C9—C10—C11—C12178.3 (3)
C15—N2—C1—O1172.3 (8)H11—C11—C12—H121.8 (10)
C2—N2—C1—O110.0 (9)C10—C11—C12—H12179.9 (7)
C1—N2—C2—C364.5 (5)H11—C11—C12—C13179.2 (7)
C15—N2—C2—C3113.3 (4)C10—C11—C12—C131.1 (5)
C1—N2—C2—C7115.7 (4)H12—C12—C13—H131.0 (10)
C15—N2—C2—C766.5 (5)C11—C12—C13—H13180.0 (7)
C7—C2—C3—H3178.4 (7)H12—C12—C13—C14179.2 (7)
N2—C2—C3—H31.3 (8)C11—C12—C13—C140.2 (6)
C7—C2—C3—C41.0 (6)H13—C13—C14—H140.4 (10)
N2—C2—C3—C4179.2 (4)C12—C13—C14—H14179.4 (7)
H3—C3—C4—H40.4 (11)H13—C13—C14—C15179.8 (7)
C2—C3—C4—H4179.8 (7)C12—C13—C14—C150.4 (6)
H3—C3—C4—C5179.5 (7)H14—C14—C15—C10178.3 (7)
C2—C3—C4—C50.0 (6)C13—C14—C15—C101.5 (5)
H4—C4—C5—H50.6 (11)H14—C14—C15—N21.2 (8)
C3—C4—C5—H5179.6 (7)C13—C14—C15—N2179.0 (3)
H4—C4—C5—C6179.4 (7)C11—C10—C15—C142.4 (5)
C3—C4—C5—C60.4 (6)C9—C10—C15—C14178.2 (3)
H5—C5—C6—H60.6 (11)C11—C10—C15—N2178.2 (3)
C4—C5—C6—H6179.4 (7)C9—C10—C15—N21.3 (5)
H5—C5—C6—C7179.8 (7)C1—N2—C15—C1464.6 (5)
C4—C5—C6—C70.2 (6)C2—N2—C15—C14113.1 (4)
C3—C2—C7—C61.6 (6)C1—N2—C15—C10115.9 (4)
N2—C2—C7—C6178.6 (3)C2—N2—C15—C1066.3 (4)
(dihydrate_mono_XRAY) top
Crystal data top
C15H12N2O·2(H2O)F(000) = 576
Mr = 272.3Dx = 1.311 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1597 reflections
a = 10.144 (4) Åθ = 2.8–25.2°
b = 28.891 (11) ŵ = 0.09 mm1
c = 4.847 (2) ÅT = 100 K
β = 103.763 (12)°Prism, colourless
V = 1379.7 (10) Å30.4 × 0.29 × 0.18 mm
Z = 4
Data collection top
Bruker APEX-II
diffractometer
2433 independent reflections
Radiation source: sealed x-ray tube1534 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.068
φ or ω oscillation scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan
SADABS2012/1 - Bruker AXS area detector scaling and absorption correction
h = 1212
Tmin = 0.648, Tmax = 0.745k = 3434
13851 measured reflectionsl = 66
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: mixed
wR(F2) = 0.082H 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 parametersΔρmax = 0.18 e Å3
10 restraintsΔρmin = 0.18 e Å3
0 constraints
Crystal data top
C15H12N2O·2(H2O)V = 1379.7 (10) Å3
Mr = 272.3Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.144 (4) ŵ = 0.09 mm1
b = 28.891 (11) ÅT = 100 K
c = 4.847 (2) Å0.4 × 0.29 × 0.18 mm
β = 103.763 (12)°
Data collection top
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 = 0.745Rint = 0.068
13851 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04410 restraints
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 0.18 e Å3
2433 reflectionsΔρmin = 0.18 e Å3
214 parameters
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.3864 (5)0.04784 (17)0.5278 (9)0.0142 (12)*0.5
N1A0.3827 (7)0.0458 (2)0.5714 (12)0.0184 (16)*0.5
N10.6164 (7)0.0483 (2)0.6358 (11)0.0184 (16)*0.5
O1A0.6147 (5)0.04588 (17)0.6820 (9)0.0142 (12)*0.5
N20.50028 (19)0.11071 (5)0.7684 (3)0.0167 (4)
C10.5000 (2)0.06664 (6)0.6571 (4)0.0172 (5)
C20.3756 (2)0.13429 (7)0.7725 (4)0.0165 (5)
C30.2904 (2)0.11688 (7)0.9343 (4)0.0192 (5)
H30.31530.08971.04430.023*
C40.1692 (2)0.13919 (7)0.9357 (4)0.0202 (5)
H40.1110.12721.04580.024*
C50.1335 (2)0.17915 (7)0.7745 (4)0.0191 (5)
H50.05060.19440.77390.023*
C60.2187 (2)0.19659 (7)0.6156 (4)0.0187 (5)
H60.19280.22380.50610.022*
C70.3423 (2)0.17523 (6)0.6117 (4)0.0153 (5)
C80.4321 (2)0.19605 (7)0.4476 (4)0.0177 (5)
H80.38920.21110.27550.021*
C90.5683 (2)0.19592 (7)0.5157 (4)0.0178 (5)
H90.61170.21080.38630.021*
C100.6575 (2)0.17523 (7)0.7691 (4)0.0164 (5)
C110.7816 (2)0.19654 (7)0.8968 (4)0.0192 (5)
H110.80780.22370.81270.023*
C120.8666 (2)0.17921 (7)1.1413 (4)0.0184 (5)
H120.94920.19471.22410.022*
C130.8315 (2)0.13912 (7)1.2666 (4)0.0202 (5)
H130.890.1271.43390.024*
C140.7098 (2)0.11696 (7)1.1437 (4)0.0188 (5)
H140.68460.08981.2290.023*
C150.6246 (2)0.13438 (7)0.8966 (4)0.0161 (5)
H1A0.6980 (16)0.0567 (12)0.744 (7)0.020 (6)*0.5
H1B0.613 (4)0.0179 (4)0.595 (7)0.020 (6)*0.5
H1C0.3025 (17)0.0606 (10)0.539 (8)0.020 (6)*0.5
H1D0.392 (4)0.0186 (5)0.487 (7)0.020 (6)*0.5
O20.0834 (2)0.04804 (6)0.3458 (3)0.0365 (5)
H2A0.037 (2)0.0527 (9)0.480 (4)0.067 (10)*
H2B0.1718 (17)0.054 (2)0.424 (13)0.12 (3)*0.5
H2C0.094 (7)0.0173 (3)0.330 (13)0.09 (2)*0.5
O30.9176 (2)0.04805 (6)0.7630 (3)0.0374 (5)
H3A0.961 (3)0.0507 (9)0.9472 (18)0.068 (9)*
H3B0.917 (6)0.0175 (3)0.726 (10)0.044 (15)*0.5
H3C0.8300 (17)0.055 (2)0.751 (13)0.10 (3)*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0173 (11)0.0108 (8)0.0222 (9)0.0004 (8)0.0050 (8)0.0021 (7)
C10.0226 (14)0.0143 (10)0.0147 (10)0.0018 (11)0.0046 (10)0.0030 (8)
C20.0171 (14)0.0151 (11)0.0159 (10)0.0004 (10)0.0014 (9)0.0036 (8)
C30.0254 (15)0.0138 (11)0.0172 (10)0.0028 (11)0.0029 (10)0.0009 (8)
C40.0237 (15)0.0190 (11)0.0191 (11)0.0033 (11)0.0075 (10)0.0050 (9)
C50.0168 (14)0.0206 (12)0.0190 (11)0.0012 (10)0.0023 (10)0.0048 (9)
C60.0205 (14)0.0161 (11)0.0176 (10)0.0021 (10)0.0008 (10)0.0003 (8)
C70.0179 (13)0.0133 (10)0.0131 (10)0.0009 (10)0.0007 (9)0.0027 (8)
C80.0247 (16)0.0149 (11)0.0134 (10)0.0011 (10)0.0040 (10)0.0009 (8)
C90.0242 (16)0.0136 (11)0.0167 (10)0.0023 (10)0.0070 (10)0.0018 (8)
C100.0188 (14)0.0153 (11)0.0160 (10)0.0021 (10)0.0061 (9)0.0027 (8)
C110.0243 (15)0.0149 (11)0.0209 (11)0.0020 (10)0.0103 (10)0.0033 (9)
C120.0165 (14)0.0181 (11)0.0202 (11)0.0002 (10)0.0034 (10)0.0052 (9)
C130.0245 (15)0.0183 (11)0.0167 (10)0.0042 (11)0.0030 (10)0.0021 (8)
C140.0237 (15)0.0140 (11)0.0192 (11)0.0006 (10)0.0059 (10)0.0014 (8)
C150.0174 (14)0.0137 (10)0.0183 (10)0.0013 (10)0.0061 (10)0.0042 (8)
O20.0595 (16)0.0239 (10)0.0306 (9)0.0041 (10)0.0198 (10)0.0038 (8)
O30.0615 (16)0.0253 (10)0.0241 (9)0.0071 (10)0.0078 (9)0.0002 (8)
Geometric parameters (Å, º) top
O1—C11.292 (6)C7—C81.473 (3)
N1A—C11.310 (7)C8—C91.342 (3)
N1A—H1C0.9000 (11)C8—H80.95
N1A—H1D0.9000 (11)C9—C101.468 (3)
N1—C11.321 (7)C9—H90.95
N1—H1A0.9000 (11)C10—C111.406 (3)
N1—H1B0.9001 (11)C10—C151.409 (3)
O1A—C11.290 (5)C11—C121.383 (3)
N2—C11.382 (2)C11—H110.95
N2—C151.439 (3)C12—C131.393 (3)
N2—C21.441 (3)C12—H120.95
C2—C31.392 (3)C13—C141.393 (3)
C2—C71.412 (3)C13—H130.95
C3—C41.390 (3)C14—C151.394 (3)
C3—H30.95C14—H140.95
C4—C51.393 (3)O2—H2A0.9000 (11)
C4—H40.95O2—H2B0.9000 (11)
C5—C61.382 (3)O2—H2C0.9000 (11)
C5—H50.95O3—H3A0.9000 (11)
C6—C71.401 (3)O3—H3B0.9000 (11)
C6—H60.95O3—H3C0.9000 (11)
C1—N1A—H1C123 (2)C6—C7—C8119.86 (17)
C1—N1A—H1D111 (3)C2—C7—C8122.83 (19)
H1C—N1A—H1D122 (4)C9—C8—C7126.79 (19)
C1—N1—H1A124 (2)C9—C8—H8116.6
C1—N1—H1B115 (3)C7—C8—H8116.6
H1A—N1—H1B112 (4)C8—C9—C10126.90 (19)
C1—N2—C15121.78 (18)C8—C9—H9116.6
C1—N2—C2121.35 (18)C10—C9—H9116.6
C15—N2—C2116.81 (14)C11—C10—C15117.05 (19)
O1A—C1—N1A123.1 (4)C11—C10—C9119.93 (18)
O1—C1—N1120.3 (4)C15—C10—C9123.0 (2)
O1A—C1—N2118.3 (3)C12—C11—C10121.97 (19)
O1—C1—N2119.7 (3)C12—C11—H11119
N1A—C1—N2117.8 (3)C10—C11—H11119
N1—C1—N2118.7 (3)C11—C12—C13120.2 (2)
C3—C2—C7120.96 (19)C11—C12—H12119.9
C3—C2—N2120.09 (17)C13—C12—H12119.9
C7—C2—N2118.95 (17)C12—C13—C14119.3 (2)
C4—C3—C2120.25 (19)C12—C13—H13120.4
C4—C3—H3119.9C14—C13—H13120.4
C2—C3—H3119.9C13—C14—C15120.46 (19)
C3—C4—C5119.59 (19)C13—C14—H14119.8
C3—C4—H4120.2C15—C14—H14119.8
C5—C4—H4120.2C14—C15—C10121.1 (2)
C6—C5—C4120.1 (2)C14—C15—N2120.00 (17)
C6—C5—H5120C10—C15—N2118.92 (18)
C4—C5—H5120H2A—O2—H2B108 (5)
C5—C6—C7121.79 (18)H2A—O2—H2C107 (4)
C5—C6—H6119.1H3A—O3—H3B105 (4)
C7—C6—H6119.1H3A—O3—H3C107 (4)
C6—C7—C2117.30 (18)
C15—N2—C1—O1A3.1 (3)N2—C2—C7—C82.4 (3)
C2—N2—C1—O1A174.1 (2)C6—C7—C8—C9145.4 (2)
C15—N2—C1—O1175.6 (2)C2—C7—C8—C933.6 (3)
C2—N2—C1—O17.2 (3)C7—C8—C9—C100.3 (4)
C15—N2—C1—N1A173.0 (3)C8—C9—C10—C11145.2 (2)
C2—N2—C1—N1A4.2 (4)C8—C9—C10—C1534.2 (3)
C15—N2—C1—N18.7 (4)C15—C10—C11—C121.8 (3)
C2—N2—C1—N1174.1 (3)C9—C10—C11—C12177.71 (18)
C1—N2—C2—C364.5 (2)C10—C11—C12—C131.0 (3)
C15—N2—C2—C3112.8 (2)C11—C12—C13—C140.4 (3)
C1—N2—C2—C7115.9 (2)C12—C13—C14—C150.7 (3)
C15—N2—C2—C766.8 (2)C13—C14—C15—C101.6 (3)
C7—C2—C3—C41.3 (3)C13—C14—C15—N2178.80 (16)
N2—C2—C3—C4179.10 (19)C11—C10—C15—C142.0 (3)
C2—C3—C4—C50.2 (3)C9—C10—C15—C14177.40 (18)
C3—C4—C5—C60.3 (3)C11—C10—C15—N2178.31 (16)
C4—C5—C6—C70.3 (3)C9—C10—C15—N22.2 (3)
C5—C6—C7—C21.4 (3)C1—N2—C15—C1464.5 (2)
C5—C6—C7—C8177.71 (19)C2—N2—C15—C14112.9 (2)
C3—C2—C7—C61.8 (3)C1—N2—C15—C10115.9 (2)
N2—C2—C7—C6178.53 (18)C2—N2—C15—C1066.8 (2)
C3—C2—C7—C8177.20 (19)
(dihydrate_ortho_NEUTRON) top
Crystal data top
C15H12N2O·2(H2O)F(000) = 1152
Mr = 272.3Dx = 1.319 Mg m3
Orthorhombic, CmcaCell parameters from 0 reflections
Hall symbol: -C 2bc 2θ = 0–0°
a = 19.638 (6) ŵ = 0 mm1
b = 4.8378 (16) ÅT = 100 K
c = 28.856 (8) ÅPrism, colourless
V = 2741.5 (14) Å38 × 2 × 2 mm
Z = 8
Data collection top
SXD beamline
diffractometer
5374 reflections with I > 2σ(I)
Radiation source: ISIS neutron spallation sourceθmax = 84.0°, θmin = 9.5°
time of flight Laue diffraction scansh = 5340
5374 measured reflectionsk = 95
5374 independent reflectionsl = 56111
Refinement top
Refinement on F2Secondary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065All 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 reflectionsΔρmax = 1.60 e Å3
188 parametersΔρmin = 1.51 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraintsExtinction coefficient: 0.00025 (3)
Primary atom site location: structure-invariant direct methods
Crystal data top
C15H12N2O·2(H2O)V = 2741.5 (14) Å3
Mr = 272.3Z = 8
Orthorhombic, Cmcaµ = 0 mm1
a = 19.638 (6) ÅT = 100 K
b = 4.8378 (16) Å8 × 2 × 2 mm
c = 28.856 (8) Å
Data collection top
SXD beamline
diffractometer
5374 independent reflections
5374 measured reflections5374 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0650 restraints
wR(F2) = 0.171All H-atom parameters refined
S = 1.07 w = 1/[σ2(Fo2) + (0.1195P)2 + 83.2386P]
where P = (Fo2 + 2Fc2)/3
5374 reflectionsΔρmax = 1.60 e Å3
188 parametersΔρmin = 1.51 e Å3
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.0576 (4)0.136 (2)0.5453 (3)0.0088 (19)*0.5
O20.2082 (2)0.0550 (12)0.54803 (13)0.0295 (10)
N10.0580 (2)0.0835 (15)0.54742 (19)0.0105 (13)*0.5
N200.2690 (7)0.61070 (7)0.0115 (6)
C100.1573 (10)0.56669 (10)0.0115 (8)
C20.06199 (9)0.3341 (7)0.63426 (7)0.0100 (6)
C30.10488 (10)0.5393 (7)0.61662 (8)0.0128 (6)
C40.16578 (10)0.6015 (8)0.63896 (8)0.0139 (6)
C50.18376 (10)0.4577 (7)0.67927 (8)0.0134 (6)
C60.14081 (10)0.2542 (8)0.69683 (8)0.0123 (6)
C70.07862 (9)0.1908 (7)0.67511 (7)0.0101 (6)
C80.03442 (10)0.0202 (7)0.69593 (7)0.0118 (6)
H1A0.1032 (4)0.141 (4)0.5610 (4)0.031 (4)0.5
H1B0.0565 (4)0.025 (3)0.5131 (3)0.024 (3)0.5
H2A0.2337 (5)0.225 (2)0.5526 (3)0.046 (2)
H2B0.2097 (5)0.022 (4)0.5160 (3)0.029 (3)0.5
H2C0.1533 (6)0.100 (4)0.5533 (4)0.034 (4)0.5
H30.0898 (3)0.6498 (18)0.58540 (19)0.0313 (17)
H40.1987 (3)0.7603 (18)0.6251 (2)0.0304 (16)
H50.2317 (2)0.5049 (18)0.6966 (2)0.0307 (16)
H60.1544 (2)0.1444 (18)0.72831 (18)0.0285 (17)
H80.0601 (2)0.1798 (17)0.7161 (2)0.0281 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.051 (2)0.021 (3)0.0171 (14)0.0067 (19)0.0066 (13)0.0029 (18)
N20.0103 (7)0.0188 (19)0.0053 (8)000.0014 (10)
C10.0113 (10)0.017 (3)0.0056 (10)000.0008 (14)
C20.0098 (7)0.0146 (18)0.0056 (7)0.0010 (8)0.0001 (5)0.0000 (9)
C30.0138 (8)0.016 (2)0.0085 (8)0.0025 (9)0.0009 (6)0.0011 (10)
C40.0129 (8)0.0166 (19)0.0122 (9)0.0032 (9)0.0015 (6)0.0009 (11)
C50.0097 (7)0.017 (2)0.0133 (9)0.0021 (8)0.0009 (6)0.0010 (11)
C60.0090 (7)0.0173 (19)0.0106 (8)0.0004 (8)0.0016 (5)0.0014 (11)
C70.0095 (7)0.0130 (18)0.0077 (7)0.0002 (8)0.0007 (6)0.0008 (9)
C80.0097 (7)0.0161 (19)0.0098 (8)0.0003 (9)0.0001 (6)0.0008 (11)
H1A0.017 (4)0.056 (12)0.021 (5)0.000 (5)0.002 (3)0.010 (6)
H1B0.023 (4)0.037 (10)0.013 (3)0.001 (4)0.000 (3)0.002 (5)
H2A0.076 (5)0.028 (6)0.034 (3)0.013 (5)0.003 (3)0.004 (4)
H2B0.030 (4)0.039 (11)0.018 (4)0.001 (5)0.001 (3)0.001 (6)
H2C0.032 (5)0.044 (12)0.027 (5)0.004 (6)0.002 (4)0.005 (6)
H30.033 (2)0.043 (6)0.018 (2)0.006 (3)0.0042 (16)0.010 (3)
H40.030 (2)0.029 (5)0.032 (3)0.012 (3)0.0033 (18)0.003 (3)
H50.0193 (19)0.041 (5)0.032 (2)0.005 (2)0.0064 (17)0.001 (3)
H60.0240 (19)0.041 (5)0.021 (2)0.000 (2)0.0071 (15)0.010 (3)
H80.024 (2)0.028 (5)0.032 (3)0.006 (2)0.0031 (18)0.012 (3)
Geometric parameters (Å, º) top
O1—C11.292 (8)C2—C71.406 (3)
O2—H2B0.939 (11)C3—H31.089 (7)
O2—H2A0.973 (13)C3—C41.392 (3)
O2—H2C1.109 (12)C4—H41.081 (7)
N1—H1A1.009 (11)C4—C51.400 (4)
N1—H1B1.031 (11)C5—H51.089 (5)
N1—C11.316 (5)C5—C61.392 (4)
N2—C11.380 (4)C6—H61.086 (6)
N2—C2i1.429 (2)C6—C71.407 (3)
N2—C21.429 (2)C7—C81.468 (4)
C1—O1i1.292 (8)C8—H81.091 (7)
C1—N1i1.316 (6)C8—C8i1.352 (4)
C2—C31.398 (4)
H2B—O2—H2A105.2 (11)H3—C3—C2119.1 (4)
H2A—O2—H2C108.4 (12)C4—C3—C2120.2 (2)
H1A—N1—H1B118.2 (9)H4—C4—C3119.7 (4)
H1A—N1—C1121.5 (8)H4—C4—C5120.7 (4)
H1B—N1—C1117.2 (7)C3—C4—C5119.6 (3)
C1—N2—C2i121.59 (12)H5—C5—C6120.3 (5)
C1—N2—C2121.59 (12)H5—C5—C4119.6 (5)
C2i—N2—C2116.8 (2)C6—C5—C4120.1 (2)
O1—C1—O1i122.2 (8)H6—C6—C5120.1 (4)
N1i—C1—N1119.7 (6)H6—C6—C7118.7 (4)
O1—C1—N2118.0 (4)C5—C6—C7121.2 (2)
O1i—C1—N2118.0 (4)C2—C7—C6117.9 (2)
N1i—C1—N2119.7 (3)C2—C7—C8123.27 (18)
N1—C1—N2119.7 (3)C6—C7—C8118.8 (2)
C3—C2—C7121.03 (19)H8—C8—C8i117.5 (3)
C3—C2—N2119.8 (2)H8—C8—C7115.9 (4)
C7—C2—N2119.2 (2)C8i—C8—C7126.23 (13)
H3—C3—C4120.8 (4)
H1A—N1—C1—O1165.6 (14)H3—C3—C4—H40.4 (8)
H1B—N1—C1—O15.8 (14)C2—C3—C4—H4179.9 (5)
H1A—N1—C1—O1i73 (3)H3—C3—C4—C5179.5 (5)
H1B—N1—C1—O1i87 (3)C2—C3—C4—C50.1 (4)
H1A—N1—C1—N1i178.6 (11)H4—C4—C5—H50.6 (8)
H1B—N1—C1—N1i18.8 (15)C3—C4—C5—H5179.4 (5)
H1A—N1—C1—N212.5 (15)H4—C4—C5—C6179.8 (5)
H1B—N1—C1—N2172.3 (11)C3—C4—C5—C60.1 (5)
C2i—N2—C1—O1171.5 (6)H5—C5—C6—H61.3 (8)
C2—N2—C1—O16.3 (8)C4—C5—C6—H6179.2 (5)
C2i—N2—C1—O1i6.3 (8)H5—C5—C6—C7179.8 (5)
C2—N2—C1—O1i171.5 (6)C4—C5—C6—C70.7 (5)
C2i—N2—C1—N1i175.6 (5)C3—C2—C7—C62.0 (4)
C2—N2—C1—N1i6.6 (6)N2—C2—C7—C6178.3 (3)
C2i—N2—C1—N16.6 (7)C3—C2—C7—C8178.0 (3)
C2—N2—C1—N1175.6 (5)N2—C2—C7—C81.6 (4)
C1—N2—C2—C364.6 (4)H6—C6—C7—C2179.7 (5)
C2i—N2—C2—C3113.3 (3)C5—C6—C7—C21.8 (4)
C1—N2—C2—C7115.7 (4)H6—C6—C7—C80.3 (6)
C2i—N2—C2—C766.4 (5)C5—C6—C7—C8178.2 (3)
C7—C2—C3—H3178.4 (5)C2—C7—C8—H8152.0 (5)
N2—C2—C3—H31.2 (6)C6—C7—C8—H827.9 (6)
C7—C2—C3—C41.2 (4)C2—C7—C8—C8i34.4 (3)
N2—C2—C3—C4179.1 (3)C6—C7—C8—C8i145.62 (19)
Symmetry code: (i) x, y, z.
(dihydrate_ortho_XRAY) top
Crystal data top
C15H12N2O·2(H2O)F(000) = 1152
Mr = 272.3Dx = 1.311 Mg m3
Orthorhombic, CmcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2Cell parameters from 1597 reflections
a = 19.705 (8) Åθ = 2.8–25.2°
b = 4.847 (2) ŵ = 0.09 mm1
c = 28.891 (11) ÅT = 100 K
V = 2759.4 (19) Å3Prism, colourless
Z = 80.4 × 0.29 × 0.18 mm
Data collection top
Bruker APEX-II
diffractometer
1258 independent reflections
Radiation source: sealed x-ray tube903 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.069
φ or ω oscillation scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan
SADABS2012/1 - Bruker AXS area detector scaling and absorption correction
h = 2323
Tmin = 0.648, Tmax = 0.745k = 55
11763 measured reflectionsl = 3434
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: mixed
wR(F2) = 0.074Only 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 parametersΔρmax = 0.19 e Å3
4 restraintsΔρmin = 0.16 e Å3
0 constraints
Crystal data top
C15H12N2O·2(H2O)V = 2759.4 (19) Å3
Mr = 272.3Z = 8
Orthorhombic, CmcaMo Kα radiation
a = 19.705 (8) ŵ = 0.09 mm1
b = 4.847 (2) ÅT = 100 K
c = 28.891 (11) Å0.4 × 0.29 × 0.18 mm
Data collection top
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 = 0.745Rint = 0.069
11763 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0394 restraints
wR(F2) = 0.074Only H-atom displacement parameters refined
S = 1.01Δρmax = 0.19 e Å3
1258 reflectionsΔρmin = 0.16 e Å3
119 parameters
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.4417 (3)0.6295 (10)0.45437 (18)0.0161 (18)*0.5
O10.5572 (2)0.5843 (8)0.45207 (14)0.0154 (14)*0.5
N20.50.7683 (4)0.38929 (6)0.0165 (5)
C10.50.6571 (4)0.43337 (7)0.0167 (6)
C20.43777 (9)0.8345 (3)0.36565 (5)0.0163 (4)
C30.39516 (9)1.0389 (3)0.38309 (5)0.0188 (4)
H30.40771.13660.41030.024 (5)*
C40.33435 (9)1.1009 (3)0.36086 (5)0.0201 (4)
H40.30511.23930.37290.028 (5)*
C50.31674 (9)0.9580 (3)0.32082 (5)0.0188 (4)
H50.27540.99940.30540.019 (4)*
C60.35930 (9)0.7561 (3)0.30343 (5)0.0187 (4)
H60.34630.65920.27630.018 (4)*
C70.42117 (9)0.6904 (3)0.32478 (5)0.0157 (4)
C80.46594 (8)0.4815 (3)0.30404 (5)0.0178 (4)
H80.44440.33060.28910.022 (5)*
H1A0.4005 (9)0.641 (7)0.4406 (9)0.019 (7)*0.5
H1B0.4447 (15)0.543 (6)0.4821 (6)0.019 (7)*0.5
O20.29152 (9)0.5540 (3)0.45193 (4)0.0369 (4)
H2A0.2699 (11)0.708 (3)0.4486 (7)0.063 (8)*
H2B0.294 (2)0.528 (9)0.4815 (5)0.054 (15)*0.5
H2C0.343 (3)0.590 (13)0.445 (2)0.12 (2)*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0169 (13)0.0219 (10)0.0107 (9)000.0019 (8)
C10.0212 (16)0.0148 (12)0.0142 (12)000.0020 (9)
C20.0177 (10)0.0173 (8)0.0140 (8)0.0027 (7)0.0009 (7)0.0040 (6)
C30.0239 (11)0.0184 (8)0.0141 (8)0.0017 (8)0.0018 (8)0.0013 (7)
C40.0241 (11)0.0177 (8)0.0184 (9)0.0024 (8)0.0035 (8)0.0039 (7)
C50.0164 (10)0.0210 (9)0.0191 (8)0.0004 (8)0.0009 (8)0.0055 (7)
C60.0223 (11)0.0187 (8)0.0153 (8)0.0046 (8)0.0018 (8)0.0018 (7)
C70.0185 (10)0.0145 (8)0.0142 (8)0.0025 (7)0.0020 (7)0.0029 (6)
C80.0245 (9)0.0146 (8)0.0143 (8)0.0017 (7)0.0019 (7)0.0003 (7)
O20.0609 (12)0.0256 (8)0.0241 (7)0.0067 (8)0.0056 (7)0.0027 (6)
Geometric parameters (Å, º) top
N1—C11.305 (6)C4—C51.392 (2)
N1—H1A0.907 (15)C4—H40.95
N1—H1B0.907 (15)C5—C61.383 (2)
O1—C11.299 (5)C5—H50.95
N2—C11.383 (3)C6—C71.403 (2)
N2—C2i1.4398 (19)C6—H60.95
N2—C21.4398 (19)C7—C81.471 (2)
C1—O1i1.299 (5)C8—C8i1.342 (3)
C1—N1i1.305 (6)C8—H80.95
C2—C31.393 (2)O2—H2A0.866 (14)
C2—C71.410 (2)O2—H2B0.866 (14)
C3—C41.392 (2)O2—H2C1.06 (6)
C3—H30.95
C1—N1—H1A125.3 (19)C5—C4—C3119.37 (16)
C1—N1—H1B114 (2)C5—C4—H4120.3
H1A—N1—H1B118 (3)C3—C4—H4120.3
C1—N2—C2i121.58 (9)C6—C5—C4120.18 (16)
C1—N2—C2121.58 (9)C6—C5—H5119.9
C2i—N2—C2116.78 (17)C4—C5—H5119.9
O1i—C1—O1120.4 (4)C5—C6—C7121.84 (15)
N1i—C1—N1123.2 (5)C5—C6—H6119.1
O1i—C1—N2119.3 (2)C7—C6—H6119.1
O1—C1—N2119.3 (2)C6—C7—C2117.22 (15)
N1i—C1—N2117.9 (3)C6—C7—C8119.89 (14)
N1—C1—N2117.9 (3)C2—C7—C8122.88 (15)
C3—C2—C7121.00 (16)C8i—C8—C7126.86 (9)
C3—C2—N2120.03 (15)C8i—C8—H8116.6
C7—C2—N2118.97 (15)C7—C8—H8116.6
C4—C3—C2120.36 (15)H2A—O2—H2B105 (3)
C4—C3—H3119.8H2A—O2—H2C108 (4)
C2—C3—H3119.8H2B—O2—H2C99 (4)
C2i—N2—C1—O1i175.6 (3)N2—C2—C3—C4178.90 (15)
C2—N2—C1—O1i7.2 (4)C2—C3—C4—C50.5 (2)
C2i—N2—C1—O17.2 (4)C3—C4—C5—C60.2 (2)
C2—N2—C1—O1175.6 (3)C4—C5—C6—C70.7 (2)
C2i—N2—C1—N1i4.2 (4)C5—C6—C7—C21.5 (2)
C2—N2—C1—N1i173.0 (3)C5—C6—C7—C8177.69 (14)
C2i—N2—C1—N1173.0 (3)C3—C2—C7—C61.9 (2)
C2—N2—C1—N14.2 (4)N2—C2—C7—C6178.42 (14)
C1—N2—C2—C364.5 (2)C3—C2—C7—C8177.33 (14)
C2i—N2—C2—C3112.90 (18)N2—C2—C7—C82.4 (2)
C1—N2—C2—C7115.8 (2)C6—C7—C8—C8i145.28 (11)
C2i—N2—C2—C766.8 (2)C2—C7—C8—C8i33.90 (18)
C7—C2—C3—C41.4 (2)
Symmetry code: (i) x+1, y, z.
(formIII_NEUTRON) top
Crystal data top
C15H12N2OV = 1141.9 (4) Å3
Mr = 236.27Z = 4
Monoclinic, P21/nDx = 1.374 Mg m3
Hall symbol: -P 2ynCell parameters from 1100 reflections
a = 7.4980 (15) ŵ = 0 mm1
b = 11.058 (2) ÅT = 100 K
c = 13.789 (3) ÅPrism, colourless
β = 92.838 (16)°8 × 2 × 2 mm
Data collection top
SXD beamline
diffractometer
8450 reflections with I > 2σ(I)
Radiation source: ISIS neutron spallation sourceθmax = 82.8°, θmin = 8.3°
time of flight Laue diffraction scansh = 2015
8450 measured reflectionsk = 3621
8450 independent reflectionsl = 2636
Refinement top
Refinement on F2Secondary atom site location: iterative
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.068All 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 reflectionsΔρmax = 1.85 e Å3
276 parametersΔρmin = 2.03 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraintsExtinction coefficient: 0.0080 (3)
Primary atom site location: iterative
Crystal data top
C15H12N2Oβ = 92.838 (16)°
Mr = 236.27V = 1141.9 (4) Å3
Monoclinic, P21/nZ = 4
a = 7.4980 (15) ŵ = 0 mm1
b = 11.058 (2) ÅT = 100 K
c = 13.789 (3) Å8 × 2 × 2 mm
Data collection top
SXD beamline
diffractometer
8450 independent reflections
8450 measured reflections8450 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0680 restraints
wR(F2) = 0.164All H-atom parameters refined
S = 1.07 w = 1/[σ2(Fo2) + (0.0888P)2 + 26.222P]
where P = (Fo2 + 2Fc2)/3
8450 reflectionsΔρmax = 1.85 e Å3
276 parametersΔρmin = 2.03 e Å3
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.0097 (3)0.3755 (2)0.40624 (18)0.0115 (4)
N10.1809 (2)0.39937 (15)0.53878 (12)0.0138 (3)
N20.2057 (2)0.23188 (13)0.43811 (10)0.0093 (3)
C10.1181 (3)0.33848 (19)0.45839 (14)0.0082 (3)
C20.1692 (3)0.16951 (18)0.34828 (14)0.0084 (3)
C30.0066 (3)0.1093 (2)0.33104 (15)0.0112 (4)
C40.0302 (3)0.0492 (2)0.24343 (16)0.0126 (4)
C50.0970 (3)0.0478 (2)0.17257 (16)0.0127 (4)
C60.2588 (3)0.1071 (2)0.18992 (15)0.0118 (4)
C70.2992 (3)0.16792 (19)0.27819 (14)0.0089 (3)
C80.4740 (3)0.2262 (2)0.29228 (16)0.0113 (4)
C90.5729 (3)0.2409 (2)0.37621 (16)0.0114 (4)
C100.5266 (3)0.19754 (19)0.47228 (15)0.0093 (3)
C110.6645 (3)0.1620 (2)0.53951 (16)0.0124 (4)
C120.6275 (3)0.1157 (2)0.62999 (16)0.0127 (4)
C130.4507 (3)0.1032 (2)0.65611 (16)0.0135 (4)
C140.3119 (3)0.1377 (2)0.59078 (16)0.0121 (4)
C150.3496 (3)0.18671 (18)0.50054 (14)0.0089 (3)
H1A0.2865 (8)0.3693 (5)0.5788 (4)0.0298 (13)
H1B0.1204 (8)0.4789 (5)0.5562 (4)0.0231 (10)
H30.0919 (8)0.1102 (6)0.3865 (4)0.0290 (11)
H40.1574 (8)0.0035 (6)0.2307 (5)0.0306 (12)
H50.0702 (9)0.0007 (6)0.1044 (4)0.0311 (13)
H60.3582 (9)0.1057 (6)0.1350 (4)0.0292 (12)
H80.5356 (9)0.2532 (6)0.2253 (4)0.0308 (13)
H90.7058 (8)0.2797 (5)0.3726 (4)0.0277 (11)
H110.8028 (7)0.1726 (6)0.5203 (5)0.0306 (12)
H120.7363 (8)0.0901 (6)0.6815 (4)0.0304 (13)
H130.4248 (9)0.0692 (6)0.7282 (4)0.0321 (13)
H140.1730 (8)0.1299 (6)0.6092 (4)0.0286 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0106 (9)0.0095 (9)0.0139 (9)0.0040 (7)0.0045 (8)0.0032 (7)
N10.0141 (7)0.0128 (7)0.0140 (6)0.0055 (5)0.0042 (5)0.0065 (5)
N20.0091 (6)0.0097 (6)0.0089 (5)0.0040 (4)0.0008 (5)0.0024 (4)
C10.0078 (7)0.0081 (8)0.0087 (7)0.0019 (6)0.0003 (6)0.0016 (5)
C20.0095 (8)0.0077 (8)0.0079 (7)0.0018 (6)0.0002 (6)0.0010 (6)
C30.0094 (8)0.0128 (9)0.0114 (8)0.0014 (6)0.0001 (7)0.0021 (6)
C40.0121 (9)0.0140 (9)0.0115 (8)0.0001 (7)0.0017 (7)0.0028 (6)
C50.0147 (10)0.0125 (9)0.0107 (8)0.0011 (7)0.0014 (7)0.0030 (6)
C60.0154 (10)0.0111 (9)0.0090 (7)0.0012 (7)0.0008 (7)0.0012 (6)
C70.0097 (8)0.0091 (8)0.0079 (7)0.0013 (6)0.0016 (6)0.0002 (6)
C80.0105 (8)0.0113 (9)0.0121 (8)0.0006 (6)0.0014 (7)0.0017 (6)
C90.0087 (8)0.0119 (9)0.0137 (9)0.0007 (6)0.0011 (7)0.0014 (6)
C100.0092 (8)0.0085 (8)0.0102 (8)0.0022 (6)0.0007 (7)0.0003 (6)
C110.0101 (8)0.0125 (9)0.0141 (8)0.0028 (7)0.0029 (7)0.0010 (7)
C120.0136 (9)0.0113 (9)0.0127 (8)0.0029 (7)0.0045 (7)0.0010 (6)
C130.0169 (10)0.0130 (9)0.0102 (8)0.0022 (7)0.0017 (7)0.0012 (6)
C140.0136 (9)0.0129 (9)0.0099 (8)0.0022 (7)0.0002 (7)0.0009 (6)
C150.0092 (8)0.0096 (8)0.0078 (7)0.0028 (6)0.0001 (6)0.0005 (5)
H1A0.027 (3)0.032 (3)0.028 (2)0.011 (2)0.012 (2)0.0088 (19)
H1B0.025 (2)0.018 (2)0.026 (2)0.0079 (16)0.0015 (19)0.0067 (16)
H30.024 (3)0.038 (3)0.026 (2)0.001 (2)0.007 (2)0.007 (2)
H40.022 (3)0.037 (3)0.032 (3)0.010 (2)0.001 (2)0.005 (2)
H50.038 (3)0.033 (3)0.022 (2)0.004 (2)0.003 (2)0.0105 (19)
H60.029 (3)0.038 (3)0.021 (2)0.002 (2)0.010 (2)0.008 (2)
H80.031 (3)0.041 (3)0.020 (2)0.010 (2)0.005 (2)0.004 (2)
H90.020 (2)0.031 (3)0.032 (3)0.0084 (19)0.000 (2)0.006 (2)
H110.015 (2)0.043 (3)0.034 (3)0.002 (2)0.000 (2)0.003 (2)
H120.029 (3)0.030 (3)0.030 (3)0.005 (2)0.013 (2)0.0048 (19)
H130.036 (3)0.041 (3)0.019 (2)0.003 (2)0.000 (2)0.011 (2)
H140.022 (2)0.037 (3)0.027 (2)0.001 (2)0.003 (2)0.004 (2)
Geometric parameters (Å, º) top
O1—C11.239 (3)C6—C71.410 (3)
N1—H1A1.000 (5)C7—C81.465 (3)
N1—H1B1.024 (5)C8—H81.094 (7)
N1—C11.361 (2)C8—C91.353 (3)
N2—C11.385 (3)C9—H91.088 (6)
N2—C21.432 (2)C9—C101.467 (3)
N2—C151.436 (2)C10—C151.407 (3)
C2—C31.399 (3)C10—C111.410 (2)
C2—C71.406 (3)C11—H111.089 (7)
C3—H31.089 (7)C11—C121.389 (4)
C3—C41.394 (3)C12—H121.092 (5)
C4—H41.086 (6)C12—C131.397 (4)
C4—C51.399 (4)C13—H131.089 (6)
C5—H51.092 (5)C13—C141.396 (3)
C5—C61.389 (3)C14—H141.088 (7)
C6—H61.088 (7)C14—C151.399 (3)
H1A—N1—H1B120.3 (4)C6—C7—C8118.5 (2)
H1A—N1—C1121.2 (4)H8—C8—C9116.9 (4)
H1B—N1—C1118.5 (3)H8—C8—C7114.9 (3)
C1—N2—C2120.81 (13)C9—C8—C7128.0 (2)
C1—N2—C15121.66 (14)H9—C9—C8118.2 (4)
C2—N2—C15117.18 (15)H9—C9—C10115.4 (3)
O1—C1—N1122.4 (2)C8—C9—C10126.1 (2)
O1—C1—N2121.66 (19)C15—C10—C11117.7 (2)
N1—C1—N2115.92 (15)C15—C10—C9123.14 (17)
C3—C2—C7120.33 (18)C11—C10—C9119.1 (2)
C3—C2—N2120.3 (2)H11—C11—C12119.6 (4)
C7—C2—N2119.41 (17)H11—C11—C10119.1 (4)
H3—C3—C4120.1 (4)C12—C11—C10121.4 (2)
H3—C3—C2119.4 (3)H12—C12—C11120.2 (5)
C4—C3—C2120.5 (2)H12—C12—C13119.6 (5)
H4—C4—C3119.7 (4)C11—C12—C13120.15 (17)
H4—C4—C5120.4 (4)H13—C13—C14121.5 (4)
C3—C4—C5119.9 (2)H13—C13—C12118.9 (4)
H5—C5—C6120.1 (4)C14—C13—C12119.6 (2)
H5—C5—C4120.3 (4)H14—C14—C13121.3 (4)
C6—C5—C4119.60 (19)H14—C14—C15118.4 (3)
H6—C6—C5119.7 (4)C13—C14—C15120.2 (2)
H6—C6—C7118.8 (4)C14—C15—C10120.94 (17)
C5—C6—C7121.5 (2)C14—C15—N2119.3 (2)
C2—C7—C6118.18 (19)C10—C15—N2119.70 (18)
C2—C7—C8123.33 (18)
H1A—N1—C1—O1178.1 (6)C2—C7—C8—C932.0 (3)
H1B—N1—C1—O10.5 (6)C6—C7—C8—C9148.0 (2)
H1A—N1—C1—N21.9 (6)H8—C8—C9—H90.9 (7)
H1B—N1—C1—N2179.6 (5)C7—C8—C9—H9174.8 (4)
C2—N2—C1—O19.3 (4)H8—C8—C9—C10172.0 (5)
C15—N2—C1—O1177.7 (3)C7—C8—C9—C101.9 (4)
C2—N2—C1—N1170.7 (2)H9—C9—C10—C15155.9 (4)
C15—N2—C1—N12.3 (3)C8—C9—C10—C1531.0 (3)
C1—N2—C2—C371.4 (3)H9—C9—C10—C1125.6 (5)
C15—N2—C2—C3115.3 (2)C8—C9—C10—C11147.5 (2)
C1—N2—C2—C7109.5 (2)C15—C10—C11—H11177.8 (5)
C15—N2—C2—C763.8 (2)C9—C10—C11—H113.6 (5)
C7—C2—C3—H3179.1 (4)C15—C10—C11—C121.2 (3)
N2—C2—C3—H30.0 (5)C9—C10—C11—C12177.4 (2)
C7—C2—C3—C41.4 (3)H11—C11—C12—H120.0 (7)
N2—C2—C3—C4179.52 (19)C10—C11—C12—H12179.0 (4)
H3—C3—C4—H40.1 (7)H11—C11—C12—C13179.1 (5)
C2—C3—C4—H4179.5 (4)C10—C11—C12—C130.1 (3)
H3—C3—C4—C5179.7 (4)H12—C12—C13—H130.9 (7)
C2—C3—C4—C50.7 (3)C11—C12—C13—H13178.2 (5)
H4—C4—C5—H51.1 (7)H12—C12—C13—C14179.0 (4)
C3—C4—C5—H5178.7 (4)C11—C12—C13—C140.1 (3)
H4—C4—C5—C6179.8 (5)H13—C13—C14—H141.3 (7)
C3—C4—C5—C60.4 (3)C12—C13—C14—H14179.4 (5)
H5—C5—C6—H60.5 (7)H13—C13—C14—C15176.8 (5)
C4—C5—C6—H6179.7 (4)C12—C13—C14—C151.3 (3)
H5—C5—C6—C7178.4 (4)H14—C14—C15—C10179.2 (4)
C4—C5—C6—C70.7 (3)C13—C14—C15—C102.7 (3)
C3—C2—C7—C61.7 (3)H14—C14—C15—N23.9 (5)
N2—C2—C7—C6179.23 (17)C13—C14—C15—N2174.3 (2)
C3—C2—C7—C8178.32 (19)C11—C10—C15—C142.5 (3)
N2—C2—C7—C80.8 (3)C9—C10—C15—C14175.9 (2)
H6—C6—C7—C2179.7 (4)C11—C10—C15—N2174.38 (19)
C5—C6—C7—C21.4 (3)C9—C10—C15—N27.1 (3)
H6—C6—C7—C80.3 (5)C1—N2—C15—C1472.3 (3)
C5—C6—C7—C8178.6 (2)C2—N2—C15—C14114.4 (2)
C2—C7—C8—H8154.0 (5)C1—N2—C15—C10104.7 (2)
C6—C7—C8—H826.0 (5)C2—N2—C15—C1068.6 (2)
(formIII_XRAY_shelx) top
Crystal data top
C15H12N2OF(000) = 496
Mr = 236.27Dx = 1.382 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9544 reflections
a = 7.4893 (4) Åθ = 6.5–57.5°
b = 11.0323 (5) ŵ = 0.09 mm1
c = 13.7640 (6) ÅT = 100 K
β = 92.953 (2)°Prism, colourless
V = 1135.73 (9) Å30.56 × 0.35 × 0.13 mm
Z = 4
Data collection top
Bruker APEX-II
diffractometer
16012 independent reflections
Radiation source: sealed x-ray tube12833 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.06
φ or ω oscillation scansθmax = 58.0°, θmin = 2.4°
Absorption correction: multi-scan
SADABS2008/1 - Bruker AXS area detector scaling and absorption correction
h = 1217
Tmin = 0.695, Tmax = 0.751k = 2625
245434 measured reflectionsl = 3232
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: mixed
wR(F2) = 0.130Only 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 parametersΔρmax = 0.73 e Å3
0 restraintsΔρmin = 0.32 e Å3
0 constraints
Crystal data top
C15H12N2OV = 1135.73 (9) Å3
Mr = 236.27Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.4893 (4) ŵ = 0.09 mm1
b = 11.0323 (5) ÅT = 100 K
c = 13.7640 (6) Å0.56 × 0.35 × 0.13 mm
β = 92.953 (2)°
Data collection top
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 = 0.751Rint = 0.06
245434 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.130Only H-atom displacement parameters refined
S = 1.04Δρmax = 0.73 e Å3
16012 reflectionsΔρmin = 0.32 e Å3
181 parameters
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.50994 (3)0.37543 (2)1.09386 (2)0.01311 (3)
N10.31930 (4)0.39948 (2)0.96130 (2)0.01521 (4)
N20.29416 (3)0.23184 (2)1.06195 (2)0.01104 (3)
C10.38163 (3)0.33847 (2)1.04159 (2)0.00998 (3)
C20.33099 (3)0.16932 (2)1.15184 (2)0.01019 (3)
C30.49366 (4)0.10930 (3)1.16891 (2)0.01276 (4)
H30.57970.10961.12060.025 (2)*
C40.53020 (4)0.04897 (3)1.25661 (2)0.01434 (4)
H40.64140.00881.26820.030 (2)*
C50.40330 (4)0.04762 (3)1.32748 (2)0.01424 (4)
H50.42780.00641.38730.024 (2)*
C60.24127 (4)0.10677 (3)1.31015 (2)0.01303 (4)
H60.15580.10611.35880.023 (2)*
C70.20087 (3)0.16776 (2)1.22187 (2)0.01073 (3)
C80.02601 (4)0.22606 (3)1.20782 (2)0.01312 (4)
H80.02410.25741.26470.037 (3)*
C90.07282 (4)0.24071 (3)1.12371 (2)0.01324 (4)
H90.18270.28311.12730.032 (3)*
C100.02683 (3)0.19751 (2)1.02774 (2)0.01141 (3)
C110.16462 (4)0.16194 (3)0.96038 (2)0.01386 (4)
H110.28550.16970.97730.026 (2)*
C120.12771 (4)0.11581 (3)0.86979 (2)0.01492 (4)
H120.2230.09270.82540.022 (2)*
C130.04913 (5)0.10330 (3)0.84371 (2)0.01537 (4)
H130.07460.07140.78180.032 (2)*
C140.18778 (4)0.13799 (3)0.90915 (2)0.01356 (4)
H140.30840.12840.89230.022 (2)*
C150.15026 (3)0.18689 (2)0.99958 (2)0.01074 (3)
H1A0.2310 (14)0.3697 (10)0.9264 (8)0.026 (2)*
H1B0.3720 (13)0.4664 (9)0.9467 (7)0.023 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.01207 (6)0.01238 (6)0.01457 (7)0.00388 (5)0.00244 (5)0.00225 (5)
N10.01620 (8)0.01360 (8)0.01532 (8)0.00518 (6)0.00420 (6)0.00575 (6)
N20.01183 (6)0.01111 (6)0.01006 (6)0.00397 (5)0.00071 (5)0.00239 (5)
C10.00967 (6)0.00948 (6)0.01080 (7)0.00157 (5)0.00068 (5)0.00134 (5)
C20.01098 (7)0.00992 (7)0.00967 (6)0.00190 (5)0.00066 (5)0.00120 (5)
C30.01136 (7)0.01443 (8)0.01253 (8)0.00054 (6)0.00095 (6)0.00216 (6)
C40.01407 (8)0.01499 (9)0.01377 (8)0.00041 (7)0.00096 (6)0.00247 (7)
C50.01771 (9)0.01362 (8)0.01126 (8)0.00096 (7)0.00050 (6)0.00236 (6)
C60.01626 (9)0.01295 (8)0.01002 (7)0.00141 (6)0.00196 (6)0.00089 (6)
C70.01241 (7)0.01023 (7)0.00965 (7)0.00110 (5)0.00146 (5)0.00002 (5)
C80.01362 (8)0.01356 (8)0.01234 (8)0.00073 (6)0.00210 (6)0.00165 (6)
C90.01210 (8)0.01306 (8)0.01460 (8)0.00043 (6)0.00090 (6)0.00092 (6)
C100.01127 (7)0.01071 (7)0.01215 (7)0.00170 (5)0.00043 (5)0.00052 (5)
C110.01249 (8)0.01392 (8)0.01486 (9)0.00262 (6)0.00230 (6)0.00115 (7)
C120.01719 (9)0.01271 (8)0.01433 (9)0.00306 (7)0.00421 (7)0.00031 (7)
C130.01934 (10)0.01455 (9)0.01200 (8)0.00217 (7)0.00144 (7)0.00143 (7)
C140.01523 (8)0.01437 (9)0.01110 (7)0.00213 (7)0.00091 (6)0.00066 (6)
C150.01150 (7)0.01046 (7)0.01019 (7)0.00267 (5)0.00014 (5)0.00070 (5)
Geometric parameters (Å, º) top
O1—C11.2394 (3)C6—H60.95
N1—C11.3561 (3)C7—C81.4628 (4)
N1—H1A0.862 (10)C8—C91.3513 (4)
N1—H1B0.865 (10)C8—H80.95
N2—C11.3822 (3)C9—C101.4621 (4)
N2—C21.4308 (3)C9—H90.95
N2—C151.4314 (3)C10—C151.4057 (4)
C2—C31.3959 (4)C10—C111.4071 (4)
C2—C71.4057 (4)C11—C121.3876 (5)
C3—C41.3931 (4)C11—H110.95
C3—H30.95C12—C131.3968 (5)
C4—C51.3966 (4)C12—H120.95
C4—H40.95C13—C141.3928 (4)
C5—C61.3876 (4)C13—H130.95
C5—H50.95C14—C151.3983 (4)
C6—C71.4081 (4)C14—H140.95
C1—N1—H1A119.1 (7)C6—C7—C8118.38 (2)
C1—N1—H1B118.1 (6)C9—C8—C7127.81 (3)
H1A—N1—H1B122.8 (10)C9—C8—H8116.1
C1—N2—C2120.88 (2)C7—C8—H8116.1
C1—N2—C15121.56 (2)C8—C9—C10126.22 (3)
C2—N2—C15117.21 (2)C8—C9—H9116.9
O1—C1—N1122.27 (2)C10—C9—H9116.9
O1—C1—N2121.58 (2)C15—C10—C11117.74 (3)
N1—C1—N2116.15 (2)C15—C10—C9123.08 (2)
C3—C2—C7120.57 (2)C11—C10—C9119.17 (2)
C3—C2—N2120.13 (2)C12—C11—C10121.40 (3)
C7—C2—N2119.29 (2)C12—C11—H11119.3
C4—C3—C2120.22 (3)C10—C11—H11119.3
C4—C3—H3119.9C11—C12—C13120.17 (3)
C2—C3—H3119.9C11—C12—H12119.9
C3—C4—C5119.99 (3)C13—C12—H12119.9
C3—C4—H4120C14—C13—C12119.46 (3)
C5—C4—H4120C14—C13—H13120.3
C6—C5—C4119.70 (3)C12—C13—H13120.3
C6—C5—H5120.1C13—C14—C15120.29 (3)
C4—C5—H5120.1C13—C14—H14119.9
C5—C6—C7121.35 (3)C15—C14—H14119.9
C5—C6—H6119.3C14—C15—C10120.89 (2)
C7—C6—H6119.3C14—C15—N2119.20 (2)
C2—C7—C6118.15 (2)C10—C15—N2119.85 (2)
C2—C7—C8123.47 (2)
C2—N2—C1—O19.38 (4)C6—C7—C8—C9147.91 (3)
C15—N2—C1—O1177.64 (3)C7—C8—C9—C101.85 (5)
C2—N2—C1—N1170.85 (3)C8—C9—C10—C1531.03 (4)
C15—N2—C1—N12.12 (4)C8—C9—C10—C11147.47 (3)
C1—N2—C2—C371.26 (3)C15—C10—C11—C121.15 (4)
C15—N2—C2—C3115.47 (3)C9—C10—C11—C12177.43 (3)
C1—N2—C2—C7109.58 (3)C10—C11—C12—C130.24 (5)
C15—N2—C2—C763.69 (3)C11—C12—C13—C140.29 (5)
C7—C2—C3—C41.23 (4)C12—C13—C14—C151.09 (5)
N2—C2—C3—C4179.62 (2)C13—C14—C15—C102.55 (4)
C2—C3—C4—C50.50 (5)C13—C14—C15—N2174.45 (3)
C3—C4—C5—C60.14 (5)C11—C10—C15—C142.54 (4)
C4—C5—C6—C70.51 (4)C9—C10—C15—C14175.99 (3)
C3—C2—C7—C61.55 (4)C11—C10—C15—N2174.44 (2)
N2—C2—C7—C6179.29 (2)C9—C10—C15—N27.03 (4)
C3—C2—C7—C8178.42 (3)C1—N2—C15—C1472.27 (4)
N2—C2—C7—C80.73 (4)C2—N2—C15—C14114.51 (3)
C5—C6—C7—C21.20 (4)C1—N2—C15—C10104.76 (3)
C5—C6—C7—C8178.78 (3)C2—N2—C15—C1068.46 (3)
C2—C7—C8—C932.07 (4)
(formIII_XRAY_xd) top
Crystal data top
C15H12N2OF(000) = 496
Mr = 236.27Dx = 1.382 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.4893 (4) ÅCell parameters from 9544 reflections
b = 11.0323 (5) Åθ = 6.5–57.5°
c = 13.7640 (6) ŵ = 0.09 mm1
β = 92.953 (2)°T = 100 K
V = 1135.73 (9) Å3Prism, colourless
Z = 40.56 × 0.35 × 0.13 mm
Data collection top
Bruker APEX-II
diffractometer
16012 independent reflections
Radiation source: sealed x-ray tube12833 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.06
φ or ω oscillation scansθmax = 58.0°, θmin = 2.4°
Absorption correction: multi-scan
SADABS2008/1 - Bruker AXS area detector scaling and absorption correction
h = 1217
Tmin = 0.695, Tmax = 0.751k = 2625
245434 measured reflectionsl = 3232
Refinement top
Refinement on FPrimary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.024Hydrogen site location: mixed
wR(F2) = 0.028 w1 = 1/[s2(Fo)]
S = 1.42(Δ/σ)max < 0.001
13153 reflectionsΔρmax = 0.25 e Å3
510 parametersΔρmin = 0.21 e Å3
0 restraints
Crystal data top
C15H12N2OV = 1135.73 (9) Å3
Mr = 236.27Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.4893 (4) ŵ = 0.09 mm1
b = 11.0323 (5) ÅT = 100 K
c = 13.7640 (6) Å0.56 × 0.35 × 0.13 mm
β = 92.953 (2)°
Data collection top
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 = 0.751Rint = 0.06
245434 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.024510 parameters
wR(F2) = 0.0280 restraints
S = 1.42Δρmax = 0.25 e Å3
13153 reflectionsΔρmin = 0.21 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/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)0.2829290.3651510.5792380.03
H(1B)0.1177520.4778520.5557930.023
H(3)0.0887360.1127480.3882110.03
H(4)0.15430.0004280.2292630.03
H(5)0.0688610.0016790.1051950.031
H(6)0.3573780.1036470.1343950.029
H(9)0.7066040.2781630.3739740.028
H(11)0.8031490.1775020.5230690.031
H(12)0.7352140.090370.6825720.031
H(13)0.4239560.066970.7270640.031
H(14)0.1875360.1277140.6065890.028
H(8)0.5237220.2554470.2223240.031
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
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)0.0299220.0309960.0282780.0089360.0120080.006465
H(1B)0.0252180.0196340.0252370.0064510.0001880.006538
H(3)0.0234280.0408890.026150.0017510.0071190.007378
H(4)0.0252180.032960.0320330.0092230.0013940.005679
H(5)0.0351010.0336360.0230350.0030760.0016770.009982
H(6)0.0266250.0395280.02140.0022350.0117130.007305
H(9)0.019290.0339830.031530.0071590.0018760.003701
H(11)0.0189520.0418930.0320420.0032180.0009830.003199
H(12)0.0292460.0316540.0302510.0043230.0126380.004633
H(13)0.0327540.0387790.0211450.0017840.000460.010041
H(14)0.0235190.0341390.0264520.0029440.0042510.00509
H(8)0.0315390.039290.022040.0107940.0047710.003135
Geometric parameters (Å, º) top
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 formulaC15H12N2O·2(H2O)C15H12N2O·2(H2O)C15H12N2O·2(H2O)C15H12N2O·2(H2O)
Mr272.3272.3272.3272.3
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/cOrthorhombic, CmcaOrthorhombic, Cmca
Temperature (K)100100100100
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), 9090, 103.763 (12), 9090, 90, 9090, 90, 90
V3)1370.7 (7)1379.7 (10)2741.5 (14)2759.4 (19)
Z4488
Radiation typeNeutrons, λ = 0.42 ÅMo Kα?, λ = 0.4-7.97 ÅMo Kα
µ (mm1)00.0900.09
Crystal size (mm)5 × 2 × 20.4 × 0.29 × 0.188 × 2 × 20.4 × 0.29 × 0.18
Data collection
DiffractometerSXD beamlineBruker APEX-IISXD beamlineBruker APEX-II
Absorption correctionMulti-scan
SADABS2012/1 - Bruker AXS area detector scaling and absorption correction
Multi-scan
SADABS2012/1 - Bruker AXS area detector scaling and absorption correction
Tmin, Tmax0.648, 0.7450.648, 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)max1)2.3670.5950.595
Distance from specimen to detector (mm)h = 5340, k = 95, l = 56111
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 reflections5423243353741258
No. of parameters365214188119
No. of restraints01004
H-atom treatmentAll H-atom parameters refinedH atoms treated by a mixture of independent and constrained refinementAll H-atom parameters refinedOnly 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 Å3)1.46, 1.340.18, 0.181.60, 1.510.19, 0.16


(formIII_NEUTRON)(formIII_XRAY_shelx)(formIII_XRAY_xd)
Crystal data
Chemical formulaC15H12N2OC15H12N2OC15H12N2O
Mr236.27236.27236.27
Crystal system, space groupMonoclinic, P21/nMonoclinic, P21/nMonoclinic, P21/n
Temperature (K)100100100
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), 9090, 92.953 (2), 9090, 92.953 (2), 90
V3)1141.9 (4)1135.73 (9)1135.73 (9)
Z444
Radiation type?, λ = 0.42 ÅMo KαMo Kα
µ (mm1)00.090.09
Crystal size (mm)8 × 2 × 20.56 × 0.35 × 0.130.56 × 0.35 × 0.13
Data collection
DiffractometerSXD beamlineBruker APEX-IIBruker APEX-II
Absorption correctionMulti-scan
SADABS2008/1 - Bruker AXS area detector scaling and absorption correction
Multi-scan
SADABS2008/1 - Bruker AXS area detector scaling and absorption correction
Tmin, Tmax0.695, 0.7510.695, 0.751
No. of measured, independent and
observed [I > 2σ(I)] reflections
8450, 8450, 8450 245434, 16012, 12833 245434, 16012, 12833
Rint?0.060.06
(sin θ/λ)max1)2.3621.1931.193
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 reflections84501601213153
No. of parameters276181510
No. of restraints000
H-atom treatmentAll H-atom parameters refinedOnly 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 Å3)1.85, 2.030.73, 0.320.25, 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).

Selected geometric parameters (Å, º) for (formIII_XRAY_xd) top
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)
 

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