An ortho­rhom­bic modification of 4,4'-diamino­benzophenone

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.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3	Prism, orange
Z = 4	0.40 × 0.30 × 0.08 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: difference Fourier map
wR(F^2) = 0.088	All H-atom parameters refined
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0594P)^2 + 0.165P] where P = (Fo^2 + 2Fc^2)/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 (Ų)

	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 (Ų)

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

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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n1···O1^i	0.86 (1)	2.08 (1)	2.917 (2)	165 (2)
N1—H1n2···O1^ii	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.