4,5-Dimethyl-1,2-bis­(quinoline-2-carboxamido)benzene

The mol­ecule of the title compound [systematic name: N,N′-(4,5-dimethyl-o-phenyl­ene)bis­(quinoline-2-carboxamide), H₂Me₂bpq], C₂₈H₂₂N₄O₂, is twisted, with a dihedral angle of 54.48 (3)° between the two quinoline ring systems. Weak C—H...O hydrogen-bonding inter­actions generate a two-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 170 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.076
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         42 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.

N,N'-(4,5-dimethyl-o-phenylene)bis(quinoline-2-carboxamide)

Crystal data

C28H22N4O2	Z = 2
Mr = 446.50	F(000) = 468
Triclinic, P1	Dx = 1.346 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7346 (10) Å	Cell parameters from 975 reflections
b = 11.9127 (17) Å	θ = 2.8–24.1°
c = 13.0732 (18) Å	µ = 0.09 mm^−1
α = 105.682 (2)°	T = 170 K
β = 92.228 (3)°	Block, pale yellow
γ = 106.699 (2)°	0.25 × 0.15 × 0.10 mm
V = 1101.9 (3) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	1789 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
Graphite monochromator	θmax = 26.0°, θmin = 1.9°
φ and ω scans	h = −9→8
6147 measured reflections	k = −14→14
4222 independent reflections	l = −16→10

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.076	H-atom parameters constrained
S = 0.96	w = [exp(5(sinθ/λ)^2)]/[σ^2(Fo^2) + (0.0127P)^2] where P = 0.33333Fo^2 + 0.66667Fc^2
4222 reflections	(Δ/σ)max = 0.001
309 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.14 e Å^−3

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.

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.

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

	x	y	z	Uiso*/Ueq
N1	0.2182 (2)	0.72034 (14)	0.68496 (13)	0.0312 (4)
N2	0.2439 (2)	0.52259 (14)	0.54550 (13)	0.0337 (4)
H2	0.2468	0.5411	0.6156	0.040*
N3	0.2951 (2)	0.38106 (15)	0.67372 (12)	0.0343 (4)
H3	0.3691	0.4538	0.7099	0.041*
N4	0.3069 (2)	0.49454 (15)	0.88242 (13)	0.0309 (4)
O1	0.1944 (2)	0.59574 (13)	0.40656 (11)	0.0495 (4)
O2	0.0755 (2)	0.21272 (13)	0.68724 (11)	0.0430 (4)
C1	0.2044 (3)	0.82109 (18)	0.76088 (16)	0.0305 (5)
C2	0.2374 (3)	0.82960 (19)	0.86964 (16)	0.0366 (5)
H2A	0.2669	0.7652	0.8887	0.044*
C3	0.2276 (3)	0.92896 (19)	0.94816 (17)	0.0424 (6)
H3A	0.2517	0.9337	1.0213	0.051*
C4	0.1818 (3)	1.02458 (19)	0.92114 (18)	0.0430 (6)
H4	0.1742	1.0934	0.9759	0.052*
C5	0.1483 (3)	1.01803 (18)	0.81599 (17)	0.0386 (6)
H5	0.1166	1.0826	0.7986	0.046*
C6	0.1598 (3)	0.91782 (18)	0.73282 (16)	0.0315 (5)
C7	0.1322 (3)	0.90805 (18)	0.62356 (17)	0.0360 (5)
H7	0.1023	0.9709	0.6020	0.043*
C8	0.1484 (3)	0.80823 (18)	0.54855 (17)	0.0354 (5)
H8	0.1311	0.8006	0.4743	0.043*
C9	0.1917 (3)	0.71626 (18)	0.58393 (16)	0.0306 (5)
C10	0.2099 (3)	0.60600 (19)	0.50195 (17)	0.0342 (5)
C11	0.2755 (3)	0.41046 (18)	0.49642 (16)	0.0306 (5)
C12	0.2809 (3)	0.36765 (18)	0.38655 (15)	0.0345 (5)
H12	0.2672	0.4168	0.3423	0.041*
C13	0.3057 (3)	0.25501 (19)	0.34060 (16)	0.0345 (5)
C14	0.3291 (3)	0.18231 (19)	0.40461 (17)	0.0360 (5)
C15	0.3281 (3)	0.22709 (18)	0.51489 (16)	0.0353 (5)
H15	0.3461	0.1795	0.5597	0.042*
C16	0.3014 (3)	0.33907 (18)	0.56061 (16)	0.0320 (5)
C17	0.1826 (3)	0.3159 (2)	0.72812 (17)	0.0337 (5)
C18	0.1950 (3)	0.38115 (19)	0.84568 (16)	0.0299 (5)
C19	0.0861 (3)	0.31723 (19)	0.90839 (17)	0.0347 (5)
H19	0.0060	0.2364	0.8771	0.042*
C20	0.0985 (3)	0.37428 (19)	1.01515 (17)	0.0367 (5)
H20	0.0288	0.3326	1.0596	0.044*
C21	0.2143 (3)	0.49460 (19)	1.05908 (16)	0.0320 (5)
C22	0.2282 (3)	0.5614 (2)	1.16813 (16)	0.0380 (5)
H22	0.1617	0.5230	1.2156	0.046*
C23	0.3358 (3)	0.6803 (2)	1.20583 (17)	0.0426 (6)
H23	0.3425	0.7245	1.2790	0.051*
C24	0.4371 (3)	0.7377 (2)	1.13679 (17)	0.0416 (6)
H24	0.5112	0.8208	1.1637	0.050*
C25	0.4302 (3)	0.67545 (19)	1.03118 (17)	0.0364 (5)
H25	0.5019	0.7147	0.9859	0.044*
C26	0.3167 (3)	0.55302 (18)	0.98962 (15)	0.0306 (5)
C27	0.3071 (3)	0.2132 (2)	0.22023 (16)	0.0462 (6)
H27A	0.2974	0.2782	0.1899	0.069*
H27B	0.2038	0.1391	0.1883	0.069*
H27C	0.4208	0.1951	0.2048	0.069*
C28	0.3500 (3)	0.05664 (19)	0.35778 (18)	0.0479 (6)
H28A	0.2369	0.0013	0.3133	0.072*
H28B	0.3765	0.0243	0.4159	0.072*
H28C	0.4502	0.0630	0.3138	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0312 (10)	0.0355 (10)	0.0272 (10)	0.0102 (8)	0.0077 (8)	0.0095 (9)
N2	0.0450 (11)	0.0347 (10)	0.0210 (9)	0.0122 (9)	0.0068 (9)	0.0072 (8)
N3	0.0424 (11)	0.0321 (10)	0.0245 (10)	0.0081 (9)	0.0028 (9)	0.0060 (8)
N4	0.0341 (10)	0.0376 (11)	0.0240 (10)	0.0153 (9)	0.0048 (8)	0.0092 (8)
O1	0.0780 (12)	0.0467 (10)	0.0254 (9)	0.0218 (9)	0.0069 (9)	0.0106 (8)
O2	0.0543 (10)	0.0367 (9)	0.0347 (9)	0.0095 (8)	0.0038 (8)	0.0104 (8)
C1	0.0273 (12)	0.0338 (13)	0.0299 (12)	0.0074 (10)	0.0074 (10)	0.0101 (11)
C2	0.0402 (13)	0.0409 (13)	0.0327 (13)	0.0139 (11)	0.0101 (11)	0.0152 (11)
C3	0.0480 (15)	0.0481 (15)	0.0289 (13)	0.0126 (12)	0.0107 (11)	0.0094 (11)
C4	0.0459 (14)	0.0355 (14)	0.0404 (14)	0.0084 (11)	0.0108 (12)	0.0035 (11)
C5	0.0392 (14)	0.0303 (12)	0.0472 (15)	0.0103 (10)	0.0109 (12)	0.0128 (11)
C6	0.0272 (12)	0.0317 (12)	0.0350 (13)	0.0072 (10)	0.0040 (10)	0.0107 (11)
C7	0.0349 (13)	0.0363 (13)	0.0413 (14)	0.0115 (10)	0.0068 (11)	0.0179 (11)
C8	0.0348 (13)	0.0402 (14)	0.0326 (13)	0.0076 (11)	0.0036 (11)	0.0171 (11)
C9	0.0285 (12)	0.0333 (12)	0.0301 (13)	0.0081 (10)	0.0063 (10)	0.0105 (11)
C10	0.0356 (13)	0.0379 (13)	0.0279 (13)	0.0078 (11)	0.0049 (11)	0.0113 (11)
C11	0.0287 (12)	0.0300 (12)	0.0286 (12)	0.0061 (10)	0.0040 (10)	0.0047 (10)
C12	0.0345 (13)	0.0403 (13)	0.0268 (12)	0.0085 (10)	0.0063 (10)	0.0099 (11)
C13	0.0266 (12)	0.0407 (14)	0.0292 (12)	0.0071 (10)	0.0051 (10)	0.0024 (11)
C14	0.0293 (12)	0.0339 (13)	0.0384 (14)	0.0088 (10)	0.0058 (10)	0.0009 (11)
C15	0.0345 (13)	0.0377 (13)	0.0336 (13)	0.0127 (10)	0.0036 (11)	0.0087 (11)
C16	0.0303 (12)	0.0349 (13)	0.0272 (12)	0.0084 (10)	0.0043 (10)	0.0050 (10)
C17	0.0393 (14)	0.0366 (13)	0.0319 (13)	0.0176 (11)	0.0036 (11)	0.0147 (11)
C18	0.0333 (13)	0.0342 (12)	0.0281 (12)	0.0167 (10)	0.0035 (10)	0.0122 (10)
C19	0.0375 (13)	0.0317 (12)	0.0403 (14)	0.0133 (10)	0.0078 (11)	0.0165 (11)
C20	0.0426 (14)	0.0403 (14)	0.0352 (13)	0.0168 (11)	0.0127 (11)	0.0189 (11)
C21	0.0326 (13)	0.0430 (14)	0.0302 (12)	0.0188 (11)	0.0094 (10)	0.0181 (11)
C22	0.0418 (14)	0.0525 (15)	0.0270 (12)	0.0203 (12)	0.0086 (11)	0.0166 (12)
C23	0.0466 (15)	0.0573 (16)	0.0241 (12)	0.0206 (13)	0.0044 (11)	0.0075 (12)
C24	0.0384 (14)	0.0472 (15)	0.0342 (13)	0.0110 (11)	−0.0013 (11)	0.0073 (12)
C25	0.0336 (13)	0.0420 (14)	0.0344 (13)	0.0097 (11)	0.0041 (11)	0.0144 (11)
C26	0.0328 (13)	0.0368 (13)	0.0275 (12)	0.0155 (10)	0.0034 (10)	0.0129 (11)
C27	0.0446 (14)	0.0552 (16)	0.0301 (13)	0.0125 (12)	0.0086 (12)	0.0011 (12)
C28	0.0462 (14)	0.0423 (14)	0.0489 (15)	0.0144 (12)	0.0098 (13)	0.0019 (12)

Geometric parameters (Å, º)

N1—C9	1.314 (2)	C12—C13	1.385 (3)
N1—C1	1.369 (2)	C12—H12	0.9500
N2—C10	1.351 (2)	C13—C14	1.398 (3)
N2—C11	1.411 (2)	C13—C27	1.518 (3)
N2—H2	0.8800	C14—C15	1.397 (3)
N3—C17	1.350 (2)	C14—C28	1.515 (3)
N3—C16	1.435 (2)	C15—C16	1.384 (3)
N3—H3	0.8800	C15—H15	0.9500
N4—C18	1.323 (2)	C17—C18	1.508 (3)
N4—C26	1.374 (2)	C18—C19	1.409 (3)
O1—C10	1.217 (2)	C19—C20	1.363 (3)
O2—C17	1.228 (2)	C19—H19	0.9500
C1—C2	1.406 (3)	C20—C21	1.402 (3)
C1—C6	1.424 (2)	C20—H20	0.9500
C2—C3	1.364 (3)	C21—C22	1.415 (3)
C2—H2A	0.9500	C21—C26	1.420 (2)
C3—C4	1.410 (3)	C22—C23	1.362 (3)
C3—H3A	0.9500	C22—H22	0.9500
C4—C5	1.366 (3)	C23—C24	1.406 (3)
C4—H4	0.9500	C23—H23	0.9500
C5—C6	1.408 (3)	C24—C25	1.370 (3)
C5—H5	0.9500	C24—H24	0.9500
C6—C7	1.404 (3)	C25—C26	1.411 (3)
C7—C8	1.362 (3)	C25—H25	0.9500
C7—H7	0.9500	C27—H27A	0.9800
C8—C9	1.414 (2)	C27—H27B	0.9800
C8—H8	0.9500	C27—H27C	0.9800
C9—C10	1.500 (3)	C28—H28A	0.9800
C11—C16	1.392 (2)	C28—H28B	0.9800
C11—C12	1.395 (3)	C28—H28C	0.9800
C9—N1—C1	117.61 (17)	C13—C14—C28	122.14 (19)
C10—N2—C11	130.22 (17)	C16—C15—C14	121.7 (2)
C10—N2—H2	114.9	C16—C15—H15	119.2
C11—N2—H2	114.9	C14—C15—H15	119.2
C17—N3—C16	124.08 (18)	C15—C16—C11	120.04 (19)
C17—N3—H3	118.0	C15—C16—N3	120.52 (18)
C16—N3—H3	118.0	C11—C16—N3	119.42 (17)
C18—N4—C26	117.04 (17)	O2—C17—N3	124.2 (2)
N1—C1—C2	118.83 (18)	O2—C17—C18	121.3 (2)
N1—C1—C6	121.95 (18)	N3—C17—C18	114.51 (19)
C2—C1—C6	119.22 (19)	N4—C18—C19	124.7 (2)
C3—C2—C1	121.0 (2)	N4—C18—C17	117.61 (18)
C3—C2—H2A	119.5	C19—C18—C17	117.72 (19)
C1—C2—H2A	119.5	C20—C19—C18	118.3 (2)
C2—C3—C4	120.2 (2)	C20—C19—H19	120.8
C2—C3—H3A	119.9	C18—C19—H19	120.8
C4—C3—H3A	119.9	C19—C20—C21	119.8 (2)
C5—C4—C3	119.9 (2)	C19—C20—H20	120.1
C5—C4—H4	120.1	C21—C20—H20	120.1
C3—C4—H4	120.1	C20—C21—C22	122.96 (19)
C4—C5—C6	121.53 (19)	C20—C21—C26	118.11 (19)
C4—C5—H5	119.2	C22—C21—C26	118.9 (2)
C6—C5—H5	119.2	C23—C22—C21	120.8 (2)
C7—C6—C5	123.95 (19)	C23—C22—H22	119.6
C7—C6—C1	117.83 (19)	C21—C22—H22	119.6
C5—C6—C1	118.22 (18)	C22—C23—C24	120.2 (2)
C8—C7—C6	119.86 (19)	C22—C23—H23	119.9
C8—C7—H7	120.1	C24—C23—H23	119.9
C6—C7—H7	120.1	C25—C24—C23	120.9 (2)
C7—C8—C9	118.32 (19)	C25—C24—H24	119.5
C7—C8—H8	120.8	C23—C24—H24	119.5
C9—C8—H8	120.8	C24—C25—C26	120.0 (2)
N1—C9—C8	124.42 (19)	C24—C25—H25	120.0
N1—C9—C10	116.86 (18)	C26—C25—H25	120.0
C8—C9—C10	118.73 (18)	N4—C26—C25	118.73 (18)
O1—C10—N2	125.1 (2)	N4—C26—C21	122.01 (19)
O1—C10—C9	121.83 (19)	C25—C26—C21	119.25 (19)
N2—C10—C9	113.05 (17)	C13—C27—H27A	109.5
C16—C11—C12	118.56 (18)	C13—C27—H27B	109.5
C16—C11—N2	118.44 (17)	H27A—C27—H27B	109.5
C12—C11—N2	123.00 (18)	C13—C27—H27C	109.5
C13—C12—C11	121.41 (19)	H27A—C27—H27C	109.5
C13—C12—H12	119.3	H27B—C27—H27C	109.5
C11—C12—H12	119.3	C14—C28—H28A	109.5
C12—C13—C14	120.16 (19)	C14—C28—H28B	109.5
C12—C13—C27	118.63 (19)	H28A—C28—H28B	109.5
C14—C13—C27	121.21 (19)	C14—C28—H28C	109.5
C15—C14—C13	118.12 (19)	H28A—C28—H28C	109.5
C15—C14—C28	119.71 (19)	H28B—C28—H28C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1	0.88	2.16	2.625 (2)	112
N3—H3···N4	0.88	2.28	2.682 (2)	108
C12—H12···O1	0.95	2.31	2.928 (2)	122
C22—H22···O1^i	0.95	2.39	3.064 (2)	128
C5—H5···O2^ii	0.95	2.47	3.364 (2)	157
C8—H8···O2^iii	0.95	2.54	3.389 (2)	149

Symmetry codes: (i) x, y, z+1; (ii) x, y+1, z; (iii) −x, −y+1, −z+1.