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organic compounds
The molecule of the title compound, C13H12N2O, uses one of its amine groups to hydrogen bond to two other molecules, affording a layer motif in the crystal structure.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806012281/bt2048sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806012281/bt2048Isup2.hkl |
CCDC reference: 608373
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.002 Å
- R factor = 0.032
- wR factor = 0.088
- Data-to-parameter ratio = 7.6
checkCIF/PLATON results
No syntax errors found
Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.702 1.000 Tmin(prime) and Tmax expected: 0.966 0.993 RR(prime) = 0.722 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.72
Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.62 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2N1 ... ? PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2N2 ... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 1470 Count of symmetry unique reflns 1482 Completeness (_total/calc) 99.19% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: CrystalClear (Rigaku/MSC, 2000); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXL97.
4,4'-Diaminobenzophenone top
Crystal data top
C13H12N2O | F(000) = 448 |
Mr = 212.25 | Dx = 1.301 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3128 reflections |
a = 5.4982 (5) Å | θ = 3.0–27.5° |
b = 8.1110 (7) Å | µ = 0.08 mm−1 |
c = 24.306 (2) Å | T = 291 K |
V = 1084.0 (2) Å3 | Prism, orange |
Z = 4 | 0.40 × 0.30 × 0.08 mm |
Data collection top
Rigaku Mercury CCD area-detector diffractometer | 1470 independent reflections |
Radiation source: fine-focus sealed tube | 1416 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (CRYSTALCLEAR; Rigaku/MSC, 2000) | h = −7→6 |
Tmin = 0.702, Tmax = 1.000 | k = −10→8 |
8288 measured reflections | l = −31→31 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.088 | All H-atom parameters refined |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0594P)2 + 0.165P] where P = (Fo2 + 2Fc2)/3 |
1470 reflections | (Δ/σ)max = 0.001 |
193 parameters | Δρmax = 0.20 e Å−3 |
12 restraints | Δρmin = −0.13 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 1.1386 (3) | 0.3386 (1) | 0.07294 (5) | 0.0376 (3) | |
N1 | 1.4721 (3) | 1.0738 (2) | 0.04297 (6) | 0.0339 (3) | |
N2 | 0.4913 (3) | 0.3221 (2) | 0.28911 (6) | 0.0347 (3) | |
C1 | 1.4247 (3) | 0.6280 (2) | 0.06495 (6) | 0.0275 (3) | |
C2 | 1.5148 (3) | 0.7786 (2) | 0.04898 (6) | 0.0277 (3) | |
C3 | 1.3868 (3) | 0.9245 (2) | 0.06073 (6) | 0.0268 (3) | |
C4 | 1.1718 (3) | 0.9135 (2) | 0.09238 (6) | 0.0264 (3) | |
C5 | 1.0882 (3) | 0.7618 (2) | 0.10947 (6) | 0.0253 (3) | |
C6 | 1.2087 (3) | 0.6163 (2) | 0.09558 (6) | 0.0249 (3) | |
C7 | 1.1028 (3) | 0.4519 (2) | 0.10606 (6) | 0.0272 (3) | |
C8 | 0.9440 (3) | 0.4236 (2) | 0.15437 (6) | 0.0263 (3) | |
C9 | 0.9868 (3) | 0.4976 (2) | 0.20551 (6) | 0.0260 (3) | |
C10 | 0.8423 (3) | 0.4614 (2) | 0.25053 (6) | 0.0270 (3) | |
C11 | 0.6433 (3) | 0.3535 (2) | 0.24539 (6) | 0.0272 (3) | |
C12 | 0.6009 (3) | 0.2802 (2) | 0.19383 (7) | 0.0318 (4) | |
C13 | 0.7501 (3) | 0.3124 (2) | 0.14987 (7) | 0.0309 (4) | |
H1n1 | 1.384 (3) | 1.160 (2) | 0.0464 (8) | 0.036 (6)* | |
H1n2 | 1.563 (3) | 1.079 (3) | 0.0144 (6) | 0.040 (6)* | |
H2n1 | 0.550 (5) | 0.345 (3) | 0.3208 (6) | 0.049 (6)* | |
H2n2 | 0.396 (4) | 0.240 (2) | 0.2849 (9) | 0.046 (6)* | |
H1 | 1.505 (4) | 0.528 (2) | 0.0558 (8) | 0.035 (5)* | |
H2 | 1.664 (2) | 0.788 (2) | 0.0291 (7) | 0.034 (5)* | |
H4 | 1.086 (3) | 1.013 (2) | 0.0993 (7) | 0.028 (5)* | |
H5 | 0.940 (2) | 0.757 (3) | 0.1298 (7) | 0.033 (5)* | |
H9 | 1.120 (3) | 0.572 (2) | 0.2089 (7) | 0.022 (4)* | |
H10 | 0.876 (3) | 0.515 (2) | 0.2849 (5) | 0.028 (5)* | |
H12 | 0.469 (3) | 0.206 (2) | 0.1894 (8) | 0.038 (5)* | |
H13 | 0.737 (4) | 0.258 (2) | 0.1150 (5) | 0.031 (5)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0531 (8) | 0.0281 (5) | 0.0316 (6) | 0.0006 (6) | 0.0034 (6) | −0.0051 (4) |
N1 | 0.0415 (9) | 0.0288 (7) | 0.0314 (7) | −0.0050 (7) | 0.0050 (6) | −0.0014 (6) |
N2 | 0.0316 (8) | 0.0418 (8) | 0.0308 (7) | −0.0065 (7) | −0.0003 (6) | 0.0035 (6) |
C1 | 0.0291 (8) | 0.0291 (7) | 0.0244 (6) | 0.0046 (7) | −0.0002 (7) | −0.0010 (6) |
C2 | 0.0251 (7) | 0.0352 (8) | 0.0229 (6) | −0.0008 (7) | 0.0011 (6) | −0.0004 (6) |
C3 | 0.0313 (8) | 0.0290 (7) | 0.0200 (6) | −0.0050 (7) | −0.0027 (6) | −0.0019 (5) |
C4 | 0.0301 (8) | 0.0250 (7) | 0.0241 (6) | 0.0023 (7) | 0.0008 (6) | −0.0020 (6) |
C5 | 0.0242 (8) | 0.0291 (7) | 0.0225 (6) | 0.0015 (7) | 0.0001 (6) | 0.0004 (6) |
C6 | 0.0266 (7) | 0.0269 (7) | 0.0211 (6) | 0.0012 (7) | −0.0022 (6) | 0.0004 (5) |
C7 | 0.0325 (8) | 0.0257 (7) | 0.0234 (6) | 0.0020 (7) | −0.0035 (6) | 0.0001 (5) |
C8 | 0.0304 (8) | 0.0226 (6) | 0.0260 (7) | 0.0007 (7) | −0.0009 (6) | 0.0017 (5) |
C9 | 0.0271 (7) | 0.0217 (7) | 0.0292 (7) | −0.0006 (7) | −0.0036 (6) | 0.0014 (5) |
C10 | 0.0295 (8) | 0.0267 (7) | 0.0249 (6) | 0.0016 (6) | −0.0042 (6) | 0.0000 (5) |
C11 | 0.0269 (8) | 0.0260 (7) | 0.0288 (7) | 0.0035 (6) | −0.0029 (7) | 0.0047 (6) |
C12 | 0.0316 (8) | 0.0288 (8) | 0.0351 (8) | −0.0071 (7) | −0.0052 (7) | 0.0026 (6) |
C13 | 0.0385 (9) | 0.0266 (7) | 0.0276 (7) | −0.0031 (7) | −0.0068 (7) | −0.0006 (6) |
Geometric parameters (Å, º) top
O1—C7 | 1.237 (2) | C10—C11 | 1.407 (2) |
N1—C3 | 1.369 (2) | C11—C12 | 1.406 (2) |
N2—C11 | 1.376 (2) | C12—C13 | 1.372 (2) |
C1—C2 | 1.374 (2) | N1—H1n1 | 0.86 (1) |
C1—C6 | 1.405 (2) | N1—H1n2 | 0.86 (1) |
C2—C3 | 1.406 (2) | N2—H2n1 | 0.85 (1) |
C3—C4 | 1.413 (2) | N2—H2n2 | 0.85 (1) |
C4—C5 | 1.378 (2) | C1—H1 | 0.95 (1) |
C4—H4 | 0.948 (9) | C2—H2 | 0.96 (1) |
C5—C6 | 1.394 (2) | C5—H5 | 0.95 (1) |
C6—C7 | 1.477 (2) | C9—H9 | 0.95 (1) |
C7—C8 | 1.481 (2) | C10—H10 | 0.96 (1) |
C8—C9 | 1.400 (2) | C12—H12 | 0.95 (1) |
C8—C13 | 1.401 (2) | C13—H13 | 0.96 (1) |
C9—C10 | 1.384 (2) | ||
C2—C1—C6 | 121.0 (2) | C3—N1—H1n1 | 120 (1) |
C1—C2—C3 | 120.7 (1) | C3—N1—H1n2 | 120 (1) |
N1—C3—C2 | 120.6 (1) | H1n1—N1—H1n2 | 112 (2) |
N1—C3—C4 | 121.0 (2) | C11—N2—H2n1 | 115 (2) |
C2—C3—C4 | 118.5 (1) | C11—N2—H2n2 | 115 (2) |
C5—C4—C3 | 120.0 (1) | H2n1—N2—H2n2 | 121 (2) |
C4—C5—C6 | 121.6 (1) | C2—C1—H1 | 122 (1) |
C5—C6—C1 | 118.2 (1) | C6—C1—H1 | 117 (1) |
C5—C6—C7 | 122.3 (1) | C1—C2—H2 | 122 (1) |
C1—C6—C7 | 119.0 (1) | C3—C2—H2 | 118 (1) |
O1—C7—C6 | 119.7 (1) | C5—C4—H4 | 123 (1) |
O1—C7—C8 | 119.6 (2) | C3—C4—H4 | 117 (1) |
C6—C7—C8 | 120.6 (1) | C4—C5—H5 | 118 (1) |
C9—C8—C13 | 118.2 (1) | C6—C5—H5 | 120 (1) |
C9—C8—C7 | 122.6 (2) | C10—C9—H9 | 121 (1) |
C13—C8—C7 | 119.1 (1) | C8—C9—H9 | 118 (1) |
C10—C9—C8 | 121.0 (1) | C9—C10—H10 | 119 (1) |
C9—C10—C11 | 120.6 (1) | C11—C10—H10 | 121 (1) |
N2—C11—C12 | 120.6 (2) | C13—C12—H12 | 119 (1) |
N2—C11—C10 | 121.3 (1) | C11—C12—H12 | 120 (1) |
C12—C11—C10 | 118.1 (2) | C12—C13—H13 | 124 (1) |
C13—C12—C11 | 121.0 (2) | C8—C13—H13 | 115 (1) |
C12—C13—C8 | 121.1 (1) | ||
C6—C1—C2—C3 | −3.0 (2) | O1—C7—C8—C9 | 145.4 (2) |
C1—C2—C3—N1 | −177.5 (2) | C6—C7—C8—C9 | −37.7 (2) |
C1—C2—C3—C4 | 4.0 (2) | O1—C7—C8—C13 | −31.4 (2) |
N1—C3—C4—C5 | 179.5 (1) | C6—C7—C8—C13 | 145.5 (2) |
C2—C3—C4—C5 | −2.1 (2) | C13—C8—C9—C10 | 0.4 (2) |
C3—C4—C5—C6 | −1.0 (2) | C7—C8—C9—C10 | −176.5 (2) |
C4—C5—C6—C1 | 2.2 (2) | C8—C9—C10—C11 | −2.3 (2) |
C4—C5—C6—C7 | −170.4 (2) | C9—C10—C11—N2 | −177.0 (2) |
C2—C1—C6—C5 | −0.1 (2) | C9—C10—C11—C12 | 1.9 (2) |
C2—C1—C6—C7 | 172.6 (1) | N2—C11—C12—C13 | 179.3 (2) |
C5—C6—C7—O1 | 144.4 (2) | C10—C11—C12—C13 | 0.4 (2) |
C1—C6—C7—O1 | −28.1 (2) | C11—C12—C13—C8 | −2.3 (3) |
C5—C6—C7—C8 | −32.6 (2) | C9—C8—C13—C12 | 2.0 (2) |
C1—C6—C7—C8 | 154.9 (2) | C7—C8—C13—C12 | 178.9 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n1···O1i | 0.86 (1) | 2.08 (1) | 2.917 (2) | 165 (2) |
N1—H1n2···O1ii | 0.86 (1) | 2.27 (1) | 3.047 (2) | 152 (2) |
Symmetry codes: (i) x, y+1, z; (ii) x+1/2, −y+3/2, −z. |
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