Dimethyl 2-amino-biphenyl-4,4'-di-carboxyl-ate.

The title compound, C16H15NO4, exhibits two near-planar aromatic ester groups with a maximum aryl-ester torsion angle of 1.9 (2)°. The dihedral angle between the benzene rings is 44.7 (1)°. In the crystal, N-H⋯O hydrogen bonding is observed along with C-H⋯O contacts, forming chanins along [101]. No π-π inter-actions were noted between the benzene rings.

Related literature

For the synthesis of the title compound, see: Olkhovik et al. (2008 ▶). For the crystal structures of the parent dimethyl-4,4′-di­carboxyl­ate and its structurally characterized amino derivatives, see: Ritzerfeld et al. (2009 ▶); Nyburg et al. (1988 ▶). For metal-organic framework structures with this and related linkers, see: Deshpande et al. (2010 ▶); Lun et al. (2011 ▶); Gupta et al. (2012 ▶); Sudik et al. (2005 ▶).

Experimental

Crystal data

C16H15NO4

M = 285.29

Monoclinic,

a = 12.955 (3) Å

b = 7.3460 (16) Å

c = 14.422 (3) Å

β = 103.263 (10)°

V = 1336.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 90 K

0.28 × 0.12 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.972, T max = 0.994

9113 measured reflections

2463 independent reflections

1785 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.124

S = 1.01

2463 reflections

198 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813010775/ff2103sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813010775/ff2103Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813010775/ff2103Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H15NO4	F(000) = 600
Mr = 285.29	Dx = 1.418 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2401 reflections
a = 12.955 (3) Å	θ = 2.9–24.9°
b = 7.3460 (16) Å	µ = 0.10 mm−1
c = 14.422 (3) Å	T = 90 K
β = 103.263 (10)°	Plate, colourless
V = 1336.0 (5) Å3	0.28 × 0.12 × 0.06 mm
Z = 4

Bruker APEXII CCD diffractometer	2463 independent reflections
Radiation source: fine-focus sealed tube	1785 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 25.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −15→15
Tmin = 0.972, Tmax = 0.994	k = −8→8
9113 measured reflections	l = −17→17

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0609P)2 + 0.6328P] where P = (Fo2 + 2Fc2)/3
2463 reflections	(Δ/σ)max < 0.001
198 parameters	Δρmax = 0.27 e Å−3
2 restraints	Δρmin = −0.35 e Å−3

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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	0.06313 (12)	0.5135 (2)	−0.10419 (10)	0.0276 (4)
O2	−0.00179 (13)	0.7915 (2)	−0.09219 (11)	0.0351 (4)
O3	0.71122 (11)	0.6353 (2)	0.53463 (9)	0.0237 (4)
O4	0.61240 (12)	0.7629 (2)	0.62568 (10)	0.0280 (4)
N1	0.22094 (16)	1.0226 (3)	0.21975 (14)	0.0321 (5)
H1NB	0.1839 (17)	1.109 (2)	0.1855 (15)	0.038*
H1NA	0.2785 (12)	1.051 (3)	0.2629 (13)	0.038*
C1	−0.00925 (17)	0.4946 (3)	−0.19589 (14)	0.0277 (5)
H1C	−0.0122	0.3668	−0.2157	0.042*
H1B	0.0153	0.5695	−0.2428	0.042*
H1A	−0.0801	0.5349	−0.1915	0.042*
C2	0.06020 (17)	0.6717 (3)	−0.05967 (15)	0.0215 (5)
C3	0.14017 (16)	0.6815 (3)	0.03194 (14)	0.0201 (5)
C4	0.14580 (16)	0.8404 (3)	0.08492 (14)	0.0205 (5)
H4A	0.0976	0.9367	0.0624	0.025*
C5	0.22104 (16)	0.8614 (3)	0.17076 (14)	0.0190 (5)
C6	0.29167 (16)	0.7167 (3)	0.20412 (14)	0.0181 (5)
C7	0.28276 (16)	0.5577 (3)	0.14953 (14)	0.0206 (5)
H7A	0.3294	0.4592	0.1719	0.025*
C8	0.20895 (17)	0.5381 (3)	0.06445 (14)	0.0212 (5)
H8A	0.2052	0.4286	0.0287	0.025*
C9	0.37584 (16)	0.7249 (3)	0.29319 (14)	0.0188 (5)
C10	0.35757 (16)	0.7869 (3)	0.37973 (14)	0.0198 (5)
H10A	0.2899	0.8339	0.3819	0.024*
C11	0.43708 (17)	0.7805 (3)	0.46212 (14)	0.0209 (5)
H11A	0.4235	0.8229	0.5204	0.025*
C12	0.53657 (16)	0.7127 (3)	0.46029 (14)	0.0188 (5)
C13	0.55552 (17)	0.6511 (3)	0.37448 (14)	0.0211 (5)
H13A	0.6233	0.6040	0.3725	0.025*
C14	0.47657 (16)	0.6582 (3)	0.29247 (14)	0.0215 (5)
H14A	0.4909	0.6170	0.2342	0.026*
C15	0.62115 (16)	0.7076 (3)	0.54930 (15)	0.0198 (5)
C16	0.79774 (17)	0.6225 (3)	0.61760 (15)	0.0258 (5)
H16A	0.8590	0.5660	0.5999	0.039*
H16B	0.7760	0.5480	0.6662	0.039*
H16C	0.8170	0.7446	0.6431	0.039*

	U11	U22	U33	U12	U13	U23
O1	0.0266 (9)	0.0302 (9)	0.0209 (8)	0.0058 (7)	−0.0052 (7)	−0.0085 (7)
O2	0.0427 (10)	0.0261 (9)	0.0284 (9)	0.0092 (8)	−0.0087 (8)	−0.0008 (7)
O3	0.0201 (8)	0.0284 (8)	0.0188 (8)	0.0022 (7)	−0.0030 (6)	−0.0014 (6)
O4	0.0283 (9)	0.0359 (9)	0.0183 (8)	0.0000 (7)	0.0019 (7)	−0.0053 (7)
N1	0.0321 (12)	0.0302 (11)	0.0304 (12)	0.0010 (9)	−0.0001 (9)	−0.0020 (9)
C1	0.0267 (12)	0.0343 (13)	0.0168 (11)	0.0013 (10)	−0.0059 (9)	−0.0066 (9)
C2	0.0238 (11)	0.0199 (11)	0.0203 (11)	0.0008 (9)	0.0038 (9)	0.0003 (9)
C3	0.0204 (11)	0.0224 (11)	0.0171 (11)	−0.0025 (9)	0.0033 (9)	−0.0003 (9)
C4	0.0203 (11)	0.0193 (10)	0.0213 (11)	0.0015 (9)	0.0035 (9)	0.0018 (9)
C5	0.0204 (11)	0.0201 (11)	0.0175 (10)	−0.0030 (9)	0.0062 (9)	−0.0013 (9)
C6	0.0166 (10)	0.0229 (11)	0.0155 (10)	−0.0017 (9)	0.0052 (9)	0.0000 (8)
C7	0.0196 (11)	0.0210 (11)	0.0205 (11)	0.0022 (9)	0.0032 (9)	0.0002 (9)
C8	0.0234 (11)	0.0201 (11)	0.0197 (11)	0.0001 (9)	0.0037 (9)	−0.0026 (9)
C9	0.0209 (11)	0.0168 (10)	0.0176 (10)	−0.0035 (9)	0.0019 (9)	−0.0006 (8)
C10	0.0191 (11)	0.0207 (11)	0.0191 (11)	−0.0001 (9)	0.0036 (9)	−0.0021 (9)
C11	0.0251 (12)	0.0202 (11)	0.0177 (11)	0.0001 (9)	0.0055 (9)	−0.0028 (8)
C12	0.0205 (11)	0.0163 (10)	0.0181 (11)	−0.0032 (9)	0.0014 (9)	0.0014 (8)
C13	0.0187 (11)	0.0243 (12)	0.0202 (11)	0.0001 (9)	0.0044 (9)	−0.0008 (9)
C14	0.0218 (11)	0.0274 (12)	0.0162 (10)	−0.0021 (9)	0.0060 (9)	−0.0048 (9)
C15	0.0227 (12)	0.0151 (10)	0.0204 (11)	−0.0042 (9)	0.0023 (9)	0.0021 (9)
C16	0.0220 (12)	0.0291 (12)	0.0216 (11)	0.0012 (10)	−0.0047 (9)	0.0014 (10)

O1—C2	1.332 (2)	C6—C9	1.483 (3)
O1—C1	1.442 (2)	C7—C8	1.379 (3)
O2—C2	1.211 (2)	C7—H7A	0.9500
O3—C15	1.342 (2)	C8—H8A	0.9500
O3—C16	1.443 (2)	C9—C14	1.396 (3)
O4—C15	1.204 (2)	C9—C10	1.399 (3)
N1—C5	1.379 (3)	C10—C11	1.383 (3)
N1—H1NB	0.877 (5)	C10—H10A	0.9500
N1—H1NA	0.879 (5)	C11—C12	1.388 (3)
C1—H1C	0.9800	C11—H11A	0.9500
C1—H1B	0.9800	C12—C13	1.391 (3)
C1—H1A	0.9800	C12—C15	1.485 (3)
C2—C3	1.482 (3)	C13—C14	1.376 (3)
C3—C4	1.388 (3)	C13—H13A	0.9500
C3—C8	1.390 (3)	C14—H14A	0.9500
C4—C5	1.397 (3)	C16—H16A	0.9800
C4—H4A	0.9500	C16—H16B	0.9800
C5—C6	1.413 (3)	C16—H16C	0.9800
C6—C7	1.399 (3)
C2—O1—C1	116.20 (16)	C7—C8—H8A	120.6
C15—O3—C16	115.67 (16)	C3—C8—H8A	120.6
C5—N1—H1NB	113.4 (17)	C14—C9—C10	118.07 (19)
C5—N1—H1NA	117.6 (17)	C14—C9—C6	118.81 (18)
H1NB—N1—H1NA	120 (2)	C10—C9—C6	123.01 (19)
O1—C1—H1C	109.5	C11—C10—C9	120.68 (19)
O1—C1—H1B	109.5	C11—C10—H10A	119.7
H1C—C1—H1B	109.5	C9—C10—H10A	119.7
O1—C1—H1A	109.5	C10—C11—C12	120.51 (18)
H1C—C1—H1A	109.5	C10—C11—H11A	119.7
H1B—C1—H1A	109.5	C12—C11—H11A	119.7
O2—C2—O1	122.46 (19)	C11—C12—C13	119.20 (19)
O2—C2—C3	125.17 (19)	C11—C12—C15	119.80 (18)
O1—C2—C3	112.37 (17)	C13—C12—C15	121.00 (19)
C4—C3—C8	120.21 (18)	C14—C13—C12	120.3 (2)
C4—C3—C2	117.99 (18)	C14—C13—H13A	119.9
C8—C3—C2	121.80 (18)	C12—C13—H13A	119.9
C3—C4—C5	121.22 (19)	C13—C14—C9	121.25 (18)
C3—C4—H4A	119.4	C13—C14—H14A	119.4
C5—C4—H4A	119.4	C9—C14—H14A	119.4
N1—C5—C4	117.78 (19)	O4—C15—O3	123.07 (19)
N1—C5—C6	123.24 (18)	O4—C15—C12	125.2 (2)
C4—C5—C6	118.97 (18)	O3—C15—C12	111.68 (17)
C7—C6—C5	118.25 (18)	O3—C16—H16A	109.5
C7—C6—C9	118.09 (18)	O3—C16—H16B	109.5
C5—C6—C9	123.65 (18)	H16A—C16—H16B	109.5
C8—C7—C6	122.60 (19)	O3—C16—H16C	109.5
C8—C7—H7A	118.7	H16A—C16—H16C	109.5
C6—C7—H7A	118.7	H16B—C16—H16C	109.5
C7—C8—C3	118.75 (19)
C1—O1—C2—O2	2.4 (3)	C5—C6—C9—C14	−136.4 (2)
C1—O1—C2—C3	−177.63 (17)	C7—C6—C9—C10	−133.4 (2)
O2—C2—C3—C4	−0.5 (3)	C5—C6—C9—C10	47.5 (3)
O1—C2—C3—C4	179.46 (17)	C14—C9—C10—C11	−0.5 (3)
O2—C2—C3—C8	−179.8 (2)	C6—C9—C10—C11	175.68 (19)
O1—C2—C3—C8	0.2 (3)	C9—C10—C11—C12	0.1 (3)
C8—C3—C4—C5	1.0 (3)	C10—C11—C12—C13	0.0 (3)
C2—C3—C4—C5	−178.30 (18)	C10—C11—C12—C15	179.73 (18)
C3—C4—C5—N1	−179.38 (19)	C11—C12—C13—C14	0.3 (3)
C3—C4—C5—C6	−0.6 (3)	C15—C12—C13—C14	−179.44 (18)
N1—C5—C6—C7	178.43 (19)	C12—C13—C14—C9	−0.7 (3)
C4—C5—C6—C7	−0.2 (3)	C10—C9—C14—C13	0.8 (3)
N1—C5—C6—C9	−2.5 (3)	C6—C9—C14—C13	−175.55 (18)
C4—C5—C6—C9	178.85 (18)	C16—O3—C15—O4	1.7 (3)
C5—C6—C7—C8	0.8 (3)	C16—O3—C15—C12	−179.20 (16)
C9—C6—C7—C8	−178.35 (19)	C11—C12—C15—O4	−2.0 (3)
C6—C7—C8—C3	−0.5 (3)	C13—C12—C15—O4	177.7 (2)
C4—C3—C8—C7	−0.4 (3)	C11—C12—C15—O3	178.96 (18)
C2—C3—C8—C7	178.82 (19)	C13—C12—C15—O3	−1.3 (3)
C7—C6—C9—C14	42.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1NB···O2i	0.88 (1)	2.54 (2)	3.304 (3)	146 (2)
N1—H1NA···O4ii	0.88 (1)	2.33 (1)	3.147 (2)	155 (2)
C4—H4A···O2i	0.95	2.44	3.301 (3)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1NB⋯O2i	0.88 (1)	2.54 (2)	3.304 (3)	146 (2)
N1—H1NA⋯O4ii	0.88 (1)	2.33 (1)	3.147 (2)	155 (2)
C4—H4A⋯O2i	0.95	2.44	3.301 (3)	150

Symmetry codes: (i) ; (ii) .