N,N′-Bis(2-pyridyl­methyl)­pyromellitic di­imide

The title compound, C₂₂H₁₄N₄O₄, exists as a monomeric mol­ecule in which the pyridyl rings are approximately perpendicular to the pyromellitic di­imide portion [dihedral angles 83.7 (1) and 85.3 (1)°]. Adjacent mol­ecules are linked by two C—H...O interactions into a linear chain parallel to the b axis.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.033
• wR factor = 0.091
• Data-to-parameter ratio = 7.6

checkCIF/PLATON results

No syntax errors found





Alert level A
PLAT036_ALERT_1_A No s.u. Given for Flack Parameter ..............          ?

Alert level C
ABSMU01_ALERT_1_C  The ratio of given/expected absorption coefficient lies
               outside the range 0.99 <> 1.01
            Calculated value of mu =     0.102
            Value of mu given      =     0.100
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
            identifier.
            Prism
CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.99
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.61
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?

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           27.00
           From the CIF: _reflns_number_total               2062
           Count of symmetry unique reflns         2083
           Completeness (_total/calc)             98.99%
           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

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

   5 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

N,N'-bis(2-pyridylmethyl)pyromellitic diimide

Crystal data

C22H14N4O4	Dx = 1.428 Mg m^−3
Mr = 398.37	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 861 reflections
a = 11.749 (1) Å	θ = 2.6–26.6°
b = 7.498 (2) Å	µ = 0.10 mm^−1
c = 21.028 (3) Å	T = 298 K
V = 1852.3 (5) Å^3	Colorless, prism
Z = 4	0.30 × 0.24 × 0.15 mm
F(000) = 824

Data collection

Bruker SMART area-detector diffractometer	1610 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Graphite monochromator	θmax = 27.0°, θmin = 1.9°
Detector resolution: 8.33 pixels mm^-1	h = −15→11
φ and ω scans	k = −6→9
8901 measured reflections	l = −26→26
2062 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.091	w = 1/[σ^2(Fo^2) + (0.0512P)^2 + 0.1847P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
2062 reflections	Δρmax = 0.14 e Å^−3
271 parameters	Δρmin = −0.13 e Å^−3
1 restraint	Absolute structure: The calculation of the absolute structure was suppressed by a MERG 4 command in SHELXL-97.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0

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

	x	y	z	Uiso*/Ueq
O1	0.4931 (2)	0.6375 (3)	0.5000 (1)	0.0678 (6)
O2	0.0994 (2)	0.3349 (3)	0.6488 (1)	0.0651 (6)
O3	0.2338 (2)	−0.2267 (3)	0.6144 (1)	0.0664 (6)
O4	0.6336 (2)	0.0769 (3)	0.4717 (1)	0.0583 (5)
N1	0.5885 (2)	0.3759 (3)	0.4800 (1)	0.0461 (5)
N2	0.1429 (2)	0.0358 (3)	0.6392 (1)	0.0487 (6)
N3	0.5550 (2)	0.3876 (3)	0.3525 (1)	0.0531 (6)
N4	0.1874 (2)	0.0255 (4)	0.7665 (1)	0.0642 (7)
C1	0.5009 (3)	0.4773 (4)	0.5046 (1)	0.0477 (6)
C2	0.4218 (2)	0.3496 (3)	0.5364 (1)	0.0412 (6)
C3	0.3233 (2)	0.3835 (4)	0.5704 (1)	0.0451 (6)
C4	0.2678 (2)	0.2326 (3)	0.5924 (1)	0.0409 (6)
C5	0.1605 (2)	0.2181 (4)	0.6301 (1)	0.0471 (7)
C6	0.2287 (3)	−0.0659 (4)	0.6120 (1)	0.0469 (6)
C7	0.3076 (2)	0.0609 (3)	0.5810 (1)	0.0399 (6)
C8	0.4065 (2)	0.0280 (3)	0.5469 (1)	0.0429 (6)
C9	0.4617 (2)	0.1785 (4)	0.5253 (1)	0.0404 (6)
C10	0.5703 (2)	0.1943 (4)	0.4891 (1)	0.0449 (6)
C11	0.6792 (3)	0.4487 (4)	0.4415 (1)	0.0519 (7)
C12	0.6577 (2)	0.4356 (3)	0.3709 (1)	0.0436 (6)
C13	0.7451 (3)	0.4714 (4)	0.3292 (1)	0.0576 (7)
C14	0.7256 (3)	0.4554 (5)	0.2652 (2)	0.0673 (9)
C15	0.6191 (3)	0.4076 (5)	0.2450 (2)	0.0632 (8)
C16	0.5372 (3)	0.3755 (5)	0.2895 (2)	0.0582 (8)
C17	0.0556 (3)	−0.0366 (5)	0.6801 (1)	0.0554 (7)
C18	0.0890 (2)	−0.0462 (4)	0.7497 (1)	0.0464 (6)
C19	0.0156 (3)	−0.1233 (5)	0.7918 (2)	0.0594 (8)
C20	0.0424 (3)	−0.1247 (5)	0.8554 (2)	0.0688 (9)
C21	0.1429 (3)	−0.0503 (5)	0.8740 (2)	0.0684 (9)
C22	0.2123 (3)	0.0203 (5)	0.8290 (2)	0.073 (1)
H3	0.2965	0.4984	0.5778	0.054*
H8	0.4334	−0.0866	0.5392	0.051*
H11a	0.7493	0.3861	0.4515	0.062*
H11b	0.6899	0.5731	0.4527	0.062*
H13	0.8163	0.5057	0.3442	0.069*
H14	0.7835	0.4767	0.2360	0.081*
H15	0.6029	0.3973	0.2019	0.076*
H16	0.4650	0.3434	0.2755	0.070*
H17a	0.0367	−0.1556	0.6654	0.066*
H17b	−0.0122	0.0363	0.6761	0.066*
H19	−0.0519	−0.1744	0.7776	0.071*
H20	−0.0068	−0.1751	0.8850	0.083*
H21	0.1634	−0.0480	0.9167	0.082*
H22	0.2814	0.0681	0.8422	0.087*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.087 (2)	0.047 (1)	0.070 (2)	0.003 (1)	0.021 (1)	0.004 (1)
O2	0.059 (1)	0.074 (2)	0.063 (1)	0.015 (1)	0.017 (1)	−0.006 (1)
O3	0.081 (2)	0.051 (1)	0.068 (1)	−0.004 (1)	0.011 (1)	0.004 (1)
O4	0.052 (1)	0.063 (1)	0.061 (1)	0.013 (1)	0.012 (1)	−0.006 (1)
N1	0.048 (1)	0.052 (1)	0.038 (1)	0.000 (1)	0.004 (1)	0.000 (1)
N2	0.050 (1)	0.060 (1)	0.036 (1)	−0.003 (1)	0.003 (1)	−0.001 (1)
N3	0.042 (1)	0.068 (2)	0.049 (1)	−0.005 (1)	0.003 (1)	−0.009 (1)
N4	0.050 (2)	0.097 (2)	0.045 (2)	−0.017 (1)	−0.002 (1)	0.003 (1)
C1	0.060 (2)	0.047 (2)	0.036 (1)	0.004 (1)	0.002 (1)	−0.001 (1)
C2	0.047 (1)	0.043 (1)	0.033 (1)	0.006 (1)	−0.002 (1)	0.000 (1)
C3	0.055 (2)	0.042 (1)	0.038 (1)	0.010 (1)	0.004 (1)	−0.003 (1)
C4	0.046 (2)	0.047 (1)	0.030 (1)	0.005 (1)	−0.001 (1)	−0.002 (1)
C5	0.049 (2)	0.059 (2)	0.033 (1)	0.004 (1)	0.002 (1)	−0.003 (1)
C6	0.054 (2)	0.052 (2)	0.035 (1)	−0.003 (1)	−0.002 (1)	−0.001 (1)
C7	0.047 (1)	0.045 (1)	0.028 (1)	0.004 (1)	−0.004 (1)	−0.002 (1)
C8	0.050 (2)	0.042 (1)	0.036 (1)	0.006 (1)	−0.002 (1)	−0.002 (1)
C9	0.044 (2)	0.049 (2)	0.029 (1)	0.007 (1)	−0.002 (1)	−0.003 (1)
C10	0.045 (2)	0.053 (2)	0.038 (1)	0.005 (1)	−0.001 (1)	−0.003 (1)
C11	0.047 (2)	0.063 (2)	0.046 (2)	−0.007 (1)	0.001 (1)	−0.002 (1)
C12	0.041 (2)	0.047 (2)	0.042 (1)	−0.003 (1)	0.002 (1)	−0.002 (1)
C13	0.040 (2)	0.081 (2)	0.052 (2)	−0.014 (2)	0.001 (1)	0.007 (2)
C14	0.058 (2)	0.096 (3)	0.048 (2)	−0.008 (2)	0.012 (2)	0.007 (2)
C15	0.067 (2)	0.080 (2)	0.043 (2)	0.000 (2)	−0.004 (2)	−0.004 (2)
C16	0.046 (2)	0.076 (2)	0.052 (2)	−0.004 (2)	−0.004 (1)	−0.015 (1)
C17	0.047 (2)	0.078 (2)	0.041 (2)	−0.011 (1)	0.000 (1)	0.000 (1)
C18	0.044 (2)	0.058 (2)	0.038 (1)	0.000 (1)	0.001 (1)	0.003 (1)
C19	0.050 (2)	0.078 (2)	0.050 (2)	−0.008 (2)	0.002 (1)	0.006 (2)
C20	0.066 (2)	0.093 (2)	0.048 (2)	0.005 (2)	0.014 (2)	0.015 (2)
C21	0.066 (2)	0.097 (3)	0.042 (2)	0.013 (2)	−0.003 (2)	0.002 (2)
C22	0.054 (2)	0.113 (3)	0.051 (2)	−0.008 (2)	−0.012 (2)	0.000 (2)

Geometric parameters (Å, º)

O1—C1	1.208 (3)	C11—C12	1.510 (4)
O2—C5	1.199 (3)	C12—C13	1.378 (4)
O3—C6	1.208 (3)	C13—C14	1.370 (4)
O4—C10	1.209 (3)	C14—C15	1.369 (5)
N1—C1	1.380 (4)	C15—C16	1.363 (5)
N1—C10	1.391 (4)	C17—C18	1.518 (4)
N1—C11	1.446 (4)	C18—C19	1.365 (4)
N2—C5	1.395 (4)	C19—C20	1.373 (5)
N2—C6	1.387 (4)	C20—C21	1.363 (5)
N3—C12	1.317 (4)	C21—C22	1.357 (5)
N3—C16	1.343 (4)	C3—H3	0.93
N2—C17	1.443 (4)	C8—H8	0.93
N4—C18	1.323 (4)	C11—H11a	0.97
N4—C22	1.348 (4)	C11—H11b	0.97
C1—C2	1.492 (4)	C13—H13	0.93
C2—C3	1.384 (4)	C14—H14	0.93
C2—C9	1.385 (4)	C15—H15	0.93
C3—C4	1.386 (4)	C16—H16	0.93
C4—C7	1.390 (3)	C17—H17a	0.97
C4—C5	1.493 (4)	C17—H17b	0.97
C6—C7	1.480 (4)	C19—H19	0.93
C7—C8	1.387 (4)	C20—H20	0.93
C8—C9	1.378 (4)	C21—H21	0.93
C9—C10	1.491 (4)	C22—H22	0.93
C1—N1—C10	111.9 (2)	C16—C15—C14	118.6 (3)
C1—N1—C11	123.5 (2)	N3—C16—C15	123.7 (3)
C10—N1—C11	124.0 (2)	N2—C17—C18	114.1 (2)
C5—N2—C6	112.0 (2)	N4—C18—C19	123.5 (3)
C5—N2—C17	123.8 (2)	N4—C18—C17	117.6 (2)
C6—N2—C17	123.7 (3)	C17—C18—C19	118.9 (3)
C12—N3—C16	116.8 (2)	C18—C19—C20	119.3 (3)
C18—N4—C22	115.9 (3)	C19—C20—C21	118.4 (3)
O1—C1—N1	125.1 (3)	C22—C21—C22	118.7 (3)
O1—C1—C2	128.8 (3)	N4—C22—C21	124.2 (3)
N1—C1—C2	106.2 (2)	C2—C3—H3	122.7
C3—C2—C9	122.7 (2)	C4—C3—H3	122.7
C1—C2—C3	129.3 (2)	C9—C8—H8	122.6
C1—C2—C9	108.0 (2)	C7—C8—H8	122.6
C2—C3—C4	114.6 (2)	N1—C11—H11a	108.8
C3—C4—C5	129.4 (2)	C12—C11—H11a	108.8
C3—C4—C7	122.7 (3)	N1—C11—H11b	108.8
C5—C4—C7	107.9 (2)	C12—C11—H11b	108.8
O2—C5—N2	125.5 (3)	H11a—C11—H11b	107.7
O2—C5—C4	128.8 (3)	C14—C13—H13	120.5
N2—C5—C4	105.7 (2)	C12—C13—H13	120.5
O3—C6—N2	124.6 (3)	C13—C14—H14	120.7
O3—C6—C7	128.9 (3)	C15—C14—H14	120.7
N2—C6—C7	106.5 (2)	C16—C15—H15	120.7
C4—C7—C8	122.3 (2)	C14—C15—H15	120.7
C4—C7—C6	107.9 (2)	N3—C16—H16	118.2
C6—C7—C8	129.7 (2)	C15—C16—H16	118.2
C7—C8—C9	114.8 (2)	N2—C17—H17a	108.7
C8—C9—C2	122.9 (2)	C18—C17—H17a	108.7
C8—C9—C10	129.5 (2)	N2—C17—H17b	108.7
C2—C9—C10	107.5 (2)	C18—C17—H17b	108.7
O4—C10—N1	125.2 (3)	H17a—C17—H17b	107.6
O4—C10—C9	128.5 (3)	C18—C19—H19	120.3
N1—C10—C9	106.2 (2)	C20—C19—H19	120.3
N1—C11—C12	113.8 (2)	C21—C20—H20	120.8
N3—C12—C13	123.2 (3)	C19—C20—H20	120.8
N3—C12—C11	117.5 (2)	C22—C21—H21	120.7
C11—C12—C13	119.3 (3)	C20—C21—H21	120.7
C12—C13—C14	119.0 (3)	N4—C22—H22	117.9
C13—C14—C15	118.7 (3)	C21—C22—H22	117.9
C10—N1—C1—O1	−175.8 (3)	C3—C2—C9—C8	0.3 (4)
C11—N1—C1—O1	−4.2 (5)	C1—C2—C9—C8	−178.4 (2)
C10—N1—C1—C2	3.9 (3)	C3—C2—C9—C10	−178.5 (2)
C11—N1—C1—C2	175.5 (2)	C1—C2—C9—C10	2.8 (3)
O1—C1—C2—C3	−3.1 (5)	C1—N1—C10—O4	179.6 (3)
N1—C1—C2—C3	177.3 (3)	C11—N1—C10—O4	8.1 (4)
O1—C1—C2—C9	175.5 (3)	C1—N1—C10—C9	−2.2 (3)
N1—C1—C2—C9	−4.1 (3)	C11—N1—C10—C9	−173.8 (2)
C9—C2—C3—C4	0.0 (4)	C8—C9—C10—O4	−1.1 (4)
C1—C2—C3—C4	178.4 (3)	C2—C9—C10—O4	177.6 (3)
C2—C3—C4—C7	−0.3 (4)	C8—C9—C10—N1	−179.2 (3)
C2—C3—C4—C5	−179.8 (2)	C2—C9—C10—N1	−0.5 (3)
C6—N2—C5—O2	−179.9 (3)	C1—N1—C11—C12	−94.3 (3)
C17—N2—C5—O2	−8.6 (4)	C10—N1—C11—C12	76.3 (3)
C6—N2—C5—C4	0.9 (3)	C16—N3—C12—C13	−0.6 (4)
C17—N2—C5—C4	172.1 (2)	C16—N3—C12—C11	−179.6 (3)
C3—C4—C5—O2	0.6 (5)	N1—C11—C12—N3	10.3 (4)
C7—C4—C5—O2	−179.0 (3)	N1—C11—C12—C13	−168.8 (3)
C3—C4—C5—N2	179.8 (3)	N3—C12—C13—C14	−0.5 (5)
C7—C4—C5—N2	0.2 (3)	C11—C12—C13—C14	178.6 (3)
C5—N2—C6—O3	178.6 (3)	C12—C13—C14—C15	1.2 (5)
C17—N2—C6—O3	7.4 (4)	C13—C14—C15—C16	−0.9 (5)
C5—N2—C6—C7	−1.6 (3)	C12—N3—C16—C15	0.9 (5)
C17—N2—C6—C7	−172.9 (2)	C14—C15—C16—N3	−0.2 (5)
C3—C4—C7—C8	0.4 (4)	C6—N2—C17—C18	86.8 (3)
C5—C4—C7—C8	180.0 (2)	C5—N2—C17—C18	−83.5 (3)
C3—C4—C7—C6	179.2 (2)	C22—N4—C18—C19	−0.6 (5)
C5—C4—C7—C6	−1.2 (3)	C22—N4—C18—C17	177.6 (3)
O3—C6—C7—C8	0.2 (5)	N2—C17—C18—N4	5.9 (4)
N2—C6—C7—C8	−179.6 (3)	N2—C17—C18—C19	−175.8 (3)
O3—C6—C7—C4	−178.6 (3)	N4—C18—C19—C20	1.4 (5)
N2—C6—C7—C4	1.7 (3)	C17—C18—C19—C20	−176.8 (3)
C4—C7—C8—C9	−0.1 (4)	C18—C19—C20—C21	−0.8 (5)
C6—C7—C8—C9	−178.6 (2)	C19—C20—C21—C22	−0.6 (5)
C7—C8—C9—C2	−0.3 (4)	C18—N4—C22—C21	−0.9 (6)
C7—C8—C9—C10	178.3 (2)	C20—C21—C22—N4	1.5 (6)