Electron density, disorder and polymorphism: high-resolution diffraction studies of the highly polymorphic neuralgic drug carbamazepine

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.

Computing details

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

(dihydrate_mono_NEUTRON)

Crystal data

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) Å^3	5 × 2 × 2 mm
Z = 4

Data collection

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

Refinement on F^2	Secondary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.065	All H-atom parameters refined
wR(F^2) = 0.172	w = 1/[σ^2(Fo^2) + (0.1101P)^2 + 28.884P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.00099 (8)
Primary atom site location: structure-invariant direct methods

Special details

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 (Ų)

	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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

(dihydrate_mono_XRAY)

Crystal data

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) Å^3	0.4 × 0.29 × 0.18 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: mixed
wR(F^2) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0242P)^2] where P = (Fo^2 + 2Fc^2)/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

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

(dihydrate_ortho_NEUTRON)

Crystal data

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) Å^3	8 × 2 × 2 mm
Z = 8

Data collection

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

Refinement on F^2	Secondary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.065	All H-atom parameters refined
wR(F^2) = 0.171	w = 1/[σ^2(Fo^2) + (0.1195P)^2 + 83.2386P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.00025 (3)
Primary atom site location: structure-invariant direct methods

Special details

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 (Ų)

	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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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—C2^i	1.429 (2)	C6—C7	1.407 (3)
N2—C2	1.429 (2)	C7—C8	1.468 (4)
C1—O1^i	1.292 (8)	C8—H8	1.091 (7)
C1—N1^i	1.316 (6)	C8—C8^i	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—C2^i	121.59 (12)	H5—C5—C6	120.3 (5)
C1—N2—C2	121.59 (12)	H5—C5—C4	119.6 (5)
C2^i—N2—C2	116.8 (2)	C6—C5—C4	120.1 (2)
O1—C1—O1^i	122.2 (8)	H6—C6—C5	120.1 (4)
N1^i—C1—N1	119.7 (6)	H6—C6—C7	118.7 (4)
O1—C1—N2	118.0 (4)	C5—C6—C7	121.2 (2)
O1^i—C1—N2	118.0 (4)	C2—C7—C6	117.9 (2)
N1^i—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—C8^i	117.5 (3)
C3—C2—N2	119.8 (2)	H8—C8—C7	115.9 (4)
C7—C2—N2	119.2 (2)	C8^i—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—O1^i	73 (3)	H3—C3—C4—C5	−179.5 (5)
H1B—N1—C1—O1^i	−87 (3)	C2—C3—C4—C5	0.1 (4)
H1A—N1—C1—N1^i	178.6 (11)	H4—C4—C5—H5	0.6 (8)
H1B—N1—C1—N1^i	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)
C2^i—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)
C2^i—N2—C1—O1^i	−6.3 (8)	H5—C5—C6—C7	−179.8 (5)
C2—N2—C1—O1^i	171.5 (6)	C4—C5—C6—C7	0.7 (5)
C2^i—N2—C1—N1^i	175.6 (5)	C3—C2—C7—C6	2.0 (4)
C2—N2—C1—N1^i	−6.6 (6)	N2—C2—C7—C6	−178.3 (3)
C2^i—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)
C2^i—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)
C2^i—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—C8^i	34.4 (3)
N2—C2—C3—C4	179.1 (3)	C6—C7—C8—C8^i	−145.62 (19)

Symmetry code: (i) −x, y, z.

(dihydrate_ortho_XRAY)

Crystal data

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) Å^3	Prism, colourless
Z = 8	0.4 × 0.29 × 0.18 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: mixed
wR(F^2) = 0.074	Only H-atom displacement parameters refined
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0257P)^2 + 0.5684P] where P = (Fo^2 + 2Fc^2)/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

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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—C2^i	1.4398 (19)	C6—H6	0.95
N2—C2	1.4398 (19)	C7—C8	1.471 (2)
C1—O1^i	1.299 (5)	C8—C8^i	1.342 (3)
C1—N1^i	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—C2^i	121.58 (9)	C6—C5—C4	120.18 (16)
C1—N2—C2	121.58 (9)	C6—C5—H5	119.9
C2^i—N2—C2	116.78 (17)	C4—C5—H5	119.9
O1^i—C1—O1	120.4 (4)	C5—C6—C7	121.84 (15)
N1^i—C1—N1	123.2 (5)	C5—C6—H6	119.1
O1^i—C1—N2	119.3 (2)	C7—C6—H6	119.1
O1—C1—N2	119.3 (2)	C6—C7—C2	117.22 (15)
N1^i—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)	C8^i—C8—C7	126.86 (9)
C3—C2—N2	120.03 (15)	C8^i—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)
C2^i—N2—C1—O1^i	−175.6 (3)	N2—C2—C3—C4	−178.90 (15)
C2—N2—C1—O1^i	7.2 (4)	C2—C3—C4—C5	−0.5 (2)
C2^i—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)
C2^i—N2—C1—N1^i	4.2 (4)	C5—C6—C7—C2	1.5 (2)
C2—N2—C1—N1^i	−173.0 (3)	C5—C6—C7—C8	−177.69 (14)
C2^i—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)
C2^i—N2—C2—C3	−112.90 (18)	N2—C2—C7—C8	−2.4 (2)
C1—N2—C2—C7	−115.8 (2)	C6—C7—C8—C8^i	145.28 (11)
C2^i—N2—C2—C7	66.8 (2)	C2—C7—C8—C8^i	−33.90 (18)
C7—C2—C3—C4	1.4 (2)

Symmetry code: (i) −x+1, y, z.

(formIII_NEUTRON)

Crystal data

C15H12N2O	V = 1141.9 (4) Å^3
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

Data collection

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

Refinement on F^2	Secondary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.068	All H-atom parameters refined
wR(F^2) = 0.164	w = 1/[σ^2(Fo^2) + (0.0888P)^2 + 26.222P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.0080 (3)
Primary atom site location: iterative

Special details

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 (Ų)

	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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

(formIII_XRAY_shelx)

Crystal data

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) Å^3	0.56 × 0.35 × 0.13 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: mixed
wR(F^2) = 0.130	Only H-atom displacement parameters refined
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0804P)^2 + 0.0415P] where P = (Fo^2 + 2Fc^2)/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

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

(formIII_XRAY_xd)

Crystal data

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) Å^3	Prism, colourless
Z = 4	0.56 × 0.35 × 0.13 mm

Data collection

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

Refinement on F	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.024	Hydrogen site location: mixed
wR(F^2) = 0.028	w1 = 1/[s^2(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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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

Geometric parameters (Å, º)

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)