N,N'-Bis(4-pyrid­yl)naphthalene-3,4:7,8-dicarboximide dimethyl­formamide disolvate

In the title compound, C₂₄H₁₂N₄O₄·2C₃H₇NO, the naphthalene imide, which is an organic pigment utilized for H₂ gas sensors, has inversion symmetry. The pyridyl rings are twisted, in the same direction, out of the plane of the naphthalene imide skeleton by 69.5 (2)°.

Key indicators

• Single-crystal X-ray study
• T = 93 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.097
• wR factor = 0.309
• Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.93

Author Response: A two-dimensionaldetector (IP) was used in combination with Cu radiation.

Alert level B
DIFMX01_ALERT_2_B  The maximum difference density is > 0.1*ZMAX*1.00
            _refine_diff_density_max given =      1.050
            Test value =      0.800
PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............       1.05 e/A   3
PLAT413_ALERT_2_B Short Inter XH3 .. XHn     H13    ..  H15C    ..       1.98 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  O3     ..  C4      ..       2.80 Ang.

Alert level C
DIFMN02_ALERT_2_C  The minimum difference density is < -0.1*ZMAX*0.75
            _refine_diff_density_min given =     -0.730
            Test value =     -0.600
DIFMN03_ALERT_1_C  The minimum difference density is < -0.1*ZMAX*0.75
            The relevant atom site should be identified.
DIFMX02_ALERT_1_C  The minimum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           68.24
           From the CIF: _diffrn_reflns_theta_full          68.24
           From the CIF: _reflns_number_total               2241
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         2410
           Completeness (_total/calc)             92.99%
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.309
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.93
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT084_ALERT_2_C High R2 Value ..................................       0.31
PLAT098_ALERT_2_C Minimum (Negative) Residual Density ............      -0.73 e/A   3
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        C13
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N3
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H11    ..  H15A    ..       2.13 Ang.

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

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

---

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure.

(I)

Crystal data

C24H12N4O4·2C3H7NO	F(000) = 592.00
Mr = 566.57	Dx = 1.432 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 8845 reflections
a = 5.3890 (8) Å	θ = 3.6–68.1°
b = 12.2012 (17) Å	µ = 0.85 mm^−1
c = 19.998 (3) Å	T = 93 K
β = 91.764 (10)°	Needle, gold
V = 1314.3 (3) Å^3	0.50 × 0.10 × 0.05 mm
Z = 2

Data collection

Rigaku R-AXIS RAPID diffractometer	1357 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.048
48 frames, δ ω = 15° scans	θmax = 68.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −5→5
Tmin = 0.625, Tmax = 0.958	k = −14→14
12221 measured reflections	l = −23→23
2241 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.097	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.309	(Δ/σ)max < 0.001
S = 1.11	Δρmax = 1.05 e Å^−3
2241 reflections	Δρmin = −0.73 e Å^−3
187 parameters

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using reflections with F² > 2.0 σ(F²). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
O1	0.8901 (5)	0.4101 (2)	0.32327 (14)	0.0348 (8)
O2	0.2194 (5)	0.2211 (2)	0.40543 (13)	0.0372 (8)
O3	0.3096 (12)	0.8096 (6)	0.5022 (4)	0.145 (2)
N1	0.5484 (6)	0.3191 (2)	0.36374 (16)	0.0290 (9)
N2	0.5910 (7)	0.1097 (3)	0.1952 (2)	0.0419 (11)
N3	0.2190 (16)	0.9075 (4)	0.4086 (3)	0.106 (2)
C1	0.5104 (8)	0.4627 (3)	0.47284 (19)	0.0269 (10)
C2	0.7067 (7)	0.4776 (3)	0.42396 (19)	0.0261 (10)
C3	0.7295 (8)	0.4028 (3)	0.3666 (2)	0.0277 (10)
C4	0.3577 (8)	0.3006 (3)	0.4109 (2)	0.0298 (10)
C5	0.3383 (8)	0.3776 (3)	0.4673 (2)	0.0276 (10)
C6	0.1485 (8)	0.3652 (3)	0.5156 (2)	0.0289 (10)
C7	0.8745 (7)	0.5610 (3)	0.4311 (2)	0.0274 (10)
C8	0.5640 (8)	0.2468 (3)	0.3062 (2)	0.0301 (11)
C9	0.7571 (9)	0.1726 (4)	0.2988 (2)	0.0380 (12)
C10	0.7602 (9)	0.1067 (4)	0.2427 (2)	0.0429 (13)
C11	0.4106 (9)	0.1811 (4)	0.2036 (2)	0.0397 (12)
C12	0.3832 (8)	0.2526 (3)	0.2583 (2)	0.0348 (11)
C13	0.335 (2)	0.8703 (13)	0.4547 (5)	0.191 (4)
C14	0.2989 (16)	0.9523 (6)	0.3489 (3)	0.091 (2)
C15	−0.040 (2)	0.8639 (13)	0.3950 (5)	0.191 (4)
H6	0.0357	0.3056	0.5113	0.035*
H7	1.0047	0.5689	0.4004	0.033*
H9	0.8860	0.1673	0.3322	0.046*
H11	0.2857	0.1847	0.1691	0.048*
H10	0.8935	0.0564	0.2387	0.052*
H12	0.2467	0.3015	0.2612	0.042*
H13	0.5013	0.8962	0.4542	0.230*
H14A	0.4800	0.9601	0.3510	0.137*
H14B	0.2224	1.0244	0.3419	0.137*
H14C	0.2506	0.9039	0.3116	0.137*
H15A	−0.0330	0.7844	0.3883	0.287*
H15B	−0.1117	0.8988	0.3547	0.287*
H15C	−0.1436	0.8803	0.4332	0.287*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.030 (2)	0.0408 (19)	0.0335 (17)	−0.0023 (14)	0.0031 (13)	−0.0024 (14)
O2	0.040 (2)	0.0406 (19)	0.0309 (17)	−0.0119 (15)	−0.0049 (14)	−0.0049 (14)
O3	0.107 (5)	0.135 (5)	0.190 (7)	−0.002 (4)	−0.039 (5)	0.000 (5)
N1	0.029 (2)	0.033 (2)	0.0250 (19)	−0.0042 (16)	−0.0043 (15)	−0.0021 (15)
N2	0.036 (2)	0.051 (2)	0.038 (2)	−0.0011 (19)	−0.0018 (18)	−0.0133 (19)
N3	0.161 (8)	0.053 (3)	0.104 (5)	−0.008 (4)	0.003 (5)	0.033 (3)
C1	0.025 (2)	0.034 (2)	0.022 (2)	0.0057 (18)	−0.0077 (17)	0.0031 (17)
C2	0.023 (2)	0.033 (2)	0.022 (2)	0.0005 (17)	−0.0062 (16)	0.0053 (17)
C3	0.021 (2)	0.036 (2)	0.026 (2)	0.0027 (19)	−0.0060 (17)	0.0007 (18)
C4	0.024 (2)	0.042 (2)	0.024 (2)	−0.0016 (19)	−0.0077 (17)	−0.0002 (18)
C5	0.023 (2)	0.032 (2)	0.027 (2)	−0.0020 (18)	−0.0102 (18)	0.0027 (18)
C6	0.028 (2)	0.032 (2)	0.026 (2)	−0.0011 (18)	−0.0099 (18)	0.0061 (17)
C7	0.024 (2)	0.036 (2)	0.022 (2)	−0.0016 (19)	−0.0059 (17)	0.0037 (18)
C8	0.029 (2)	0.036 (2)	0.025 (2)	−0.0043 (19)	0.0022 (17)	−0.0075 (18)
C9	0.033 (2)	0.046 (2)	0.034 (2)	0.002 (2)	−0.009 (2)	−0.007 (2)
C10	0.037 (3)	0.053 (3)	0.039 (2)	0.009 (2)	−0.003 (2)	−0.013 (2)
C11	0.037 (3)	0.050 (3)	0.031 (2)	−0.002 (2)	−0.010 (2)	−0.009 (2)
C12	0.029 (2)	0.044 (2)	0.031 (2)	−0.000 (2)	−0.0073 (19)	−0.0042 (19)
C13	0.141 (7)	0.273 (11)	0.157 (7)	−0.066 (6)	−0.046 (5)	0.155 (7)
C14	0.122 (6)	0.066 (4)	0.087 (5)	0.016 (4)	0.006 (5)	−0.007 (4)
C15	0.141 (7)	0.273 (11)	0.157 (7)	−0.066 (6)	−0.046 (5)	0.155 (7)

Geometric parameters (Å, º)

O1—C3	1.246 (5)	C8—C12	1.346 (6)
O2—C4	1.226 (5)	C9—C10	1.381 (6)
N1—C3	1.412 (5)	C9—H9	0.950
N1—C4	1.434 (5)	C10—H10	0.950
N1—C8	1.455 (5)	C11—C12	1.411 (6)
N2—C10	1.297 (6)	C11—H11	0.950
N2—C11	1.320 (6)	C12—H12	0.950
C1—C1^i	1.424 (5)	C13—H13	0.950
C2—C1	1.474 (5)	C13—O3	1.216 (15)
C2—C3	1.475 (5)	C13—N3	1.188 (14)
C2—C7	1.365 (5)	C14—H14A	0.980
C5—C1	1.395 (6)	C14—H14B	0.980
C5—C4	1.474 (6)	C14—H14C	0.980
C5—C6	1.436 (6)	C14—N3	1.394 (10)
C6—H6	0.950	C15—H15A	0.980
C7—C6^i	1.405 (5)	C15—H15B	0.980
C7—H7	0.950	C15—H15C	0.980
C8—C9	1.391 (6)	C15—N3	1.511 (14)
C4···O3^i	2.802 (8)	H13···H15C^ii	1.981
C8—N1—C3	114.4 (3)	N1—C8—C12	118.2 (3)
C8—N1—C4	119.0 (3)	C9—C8—C12	119.1 (4)
C3—N1—C4	126.6 (3)	C8—C9—C10	119.5 (4)
C10—N2—C11	115.4 (4)	C8—C9—H9	120.2
C13—N3—C14	130.2 (10)	C10—C9—H9	120.2
C13—N3—C15	117.8 (9)	N2—C10—C9	123.6 (4)
C14—N3—C15	107.0 (7)	N2—C10—H10	118.2
C2—C1—C5	121.9 (3)	C9—C10—H10	118.2
C2—C1—C1^i	120.1 (3)	N2—C11—C12	127.0 (4)
C5—C1—C1^i	117.9 (3)	N2—C11—H11	116.5
C7—C2—C1	120.6 (3)	C12—C11—H11	116.5
C7—C2—C3	118.1 (3)	C8—C12—C11	115.3 (4)
C1—C2—C3	121.2 (3)	C8—C12—H12	122.3
O1—C3—N1	121.2 (3)	C11—C12—H12	122.3
O1—C3—C2	125.0 (3)	O3—C13—N3	140.3 (12)
N1—C3—C2	113.9 (3)	H13—C13—O3	109.8
O2—C4—N1	120.7 (3)	H13—C13—N3	109.9
O2—C4—C5	121.0 (3)	H14A—C14—H14B	109.5
N1—C4—C5	118.2 (3)	H14A—C14—H14C	109.5
C1—C5—C4	118.2 (3)	H14A—C14—N3	109.5
C1—C5—C6	120.7 (3)	H14B—C14—H14C	109.5
C4—C5—C6	121.1 (3)	H14B—C14—N3	109.5
C5—C6—C7^i	121.6 (3)	H14C—C14—N3	109.5
C5—C6—H6	119.2	H15A—C15—H15B	109.5
C7^i—C6—H6	119.2	H15A—C15—H15C	109.5
C2—C7—H7	120.6	H15A—C15—N3	109.5
C2—C7—C6^i	118.9 (3)	H15B—C15—H15C	109.5
H7—C7—C6^i	120.6	H15B—C15—N3	109.5
N1—C8—C9	122.7 (3)	H15C—C15—N3	109.5

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