Crystal structure of N-(7-di­bromo­methyl-5-methyl-1,8-naphthyridin-2-yl)benzamide–pyrrolidine-2,5-dione (1/1)

The title crystal is a co-crystal with the 1,8-naphthyridine derivative crystallizing with one mol­ecule of succinimide per formula unit. In the crystal, the two mol­ecules are mutually linked by N—H...O and N—H...N hydrogen bonds. The packing is consolidated by C—H...(O,N) hydrogen bonds and π–π stacking inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.062
• wR factor = 0.148
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.12
            Rint given   0.125
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections (too) Low ..         49 %
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.14 Report
PLAT125_ALERT_4_C No '_symmetry_space_group_name_Hall' Given .....     Please Do !
PLAT234_ALERT_4_C Large Hirshfeld Difference C4     --  C5      ..       0.16 Ang.
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00974 Ang.
PLAT431_ALERT_2_C Short Inter HL..A  Contact Br1    ..  O1      ..       3.09 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     15.478 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      3.542 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min)           6 Note
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density           0 Note

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT020_ALERT_3_G The value of Rint is greater than 0.12 .........      0.125 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C13 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O1     ..  C18     ..       3.02 Ang.
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
  11 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

N-(7-Dibromomethyl-5-methyl-1,8-naphthyridin-2-yl)benzamide–pyrrolidine-2,5-dione (1/1)

Crystal data

C17H13Br2N3O·C4H5NO2	F(000) = 1064
Mr = 534.21	Dx = 1.687 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.6931 (19) Å	Cell parameters from 4129 reflections
b = 15.699 (3) Å	θ = 3.1–26.0°
c = 14.614 (3) Å	µ = 3.89 mm^−1
β = 108.99 (3)°	T = 293 K
V = 2103.0 (7) Å^3	Block, white
Z = 4	0.30 × 0.28 × 0.26 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	4129 independent reflections
Radiation source: fine-focus sealed tube	2010 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.125
ω scans	θmax = 26.0°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR ; Higashi, 1995)	h = −11→11
Tmin = 0.389, Tmax = 0.432	k = −19→19
16558 measured reflections	l = −18→18

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.148	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0633P)^2] where P = (Fo^2 + 2Fc^2)/3
4129 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 1.35 e Å^−3
0 restraints	Δρmin = −0.43 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br1	0.58390 (8)	0.09771 (5)	0.60551 (6)	0.0662 (3)
Br2	0.59853 (8)	0.16358 (6)	0.40343 (6)	0.0707 (3)
O2	0.2878 (5)	0.5578 (3)	0.5158 (3)	0.0569 (13)
N2	0.1482 (5)	0.3823 (3)	0.4170 (4)	0.0384 (13)
N3	0.3233 (5)	0.2797 (3)	0.4629 (4)	0.0412 (13)
C10	−0.0753 (6)	0.2634 (4)	0.3453 (5)	0.0472 (17)
H10A	−0.1506	0.2244	0.3211	0.057*
C16	0.1779 (6)	0.2982 (4)	0.4218 (4)	0.0372 (15)
O3	0.6209 (5)	0.3572 (3)	0.6728 (4)	0.0670 (14)
C11	0.0696 (6)	0.2340 (4)	0.3875 (4)	0.0386 (15)
O1	−0.2418 (5)	0.5110 (3)	0.2818 (4)	0.0572 (13)
C8	0.0100 (6)	0.4067 (4)	0.3782 (5)	0.0408 (15)
N1	−0.0060 (5)	0.4946 (3)	0.3799 (4)	0.0431 (14)
H1A	0.0691	0.5224	0.4148	0.052*
C18	0.3969 (7)	0.5289 (4)	0.5745 (5)	0.0466 (17)
C6	−0.1117 (7)	0.6382 (4)	0.3444 (4)	0.0403 (16)
N4	0.4396 (5)	0.4441 (3)	0.5798 (4)	0.0440 (13)
H4A	0.3908	0.4057	0.5406	0.053*
C5	−0.2391 (7)	0.6855 (4)	0.3129 (5)	0.0472 (17)
H5A	−0.3286	0.6584	0.2872	0.057*
C12	0.1146 (6)	0.1482 (4)	0.3980 (5)	0.0438 (17)
C3	−0.1020 (9)	0.8141 (5)	0.3572 (6)	0.065 (2)
H3B	−0.1000	0.8733	0.3614	0.078*
C7	−0.1274 (7)	0.5432 (4)	0.3325 (5)	0.0443 (17)
C21	0.5664 (7)	0.4271 (5)	0.6533 (5)	0.0477 (17)
C15	0.3601 (6)	0.1989 (4)	0.4687 (4)	0.0397 (15)
C1	0.0213 (7)	0.6805 (4)	0.3830 (5)	0.0543 (19)
H1B	0.1075	0.6494	0.4053	0.065*
C4	−0.2326 (8)	0.7719 (5)	0.3199 (5)	0.063 (2)
H4B	−0.3187	0.8031	0.2989	0.075*
C19	0.5070 (6)	0.5760 (4)	0.6530 (5)	0.0468 (17)
H19A	0.4625	0.6011	0.6971	0.056*
H19B	0.5513	0.6209	0.6264	0.056*
C14	0.2609 (7)	0.1317 (4)	0.4380 (5)	0.0463 (17)
H14A	0.2943	0.0758	0.4447	0.056*
C2	0.0253 (8)	0.7682 (5)	0.3881 (6)	0.071 (2)
H2B	0.1143	0.7963	0.4125	0.085*
C17	0.5246 (6)	0.1862 (4)	0.5102 (5)	0.0476 (18)
H17A	0.5680	0.2398	0.5408	0.057*
C9	−0.1054 (7)	0.3486 (4)	0.3399 (5)	0.0470 (17)
H9A	−0.2005	0.3680	0.3116	0.056*
C20	0.6209 (7)	0.5095 (4)	0.7050 (5)	0.0555 (19)
H20A	0.7159	0.5240	0.7006	0.067*
H20B	0.6286	0.5056	0.7727	0.067*
C13	0.0061 (7)	0.0758 (5)	0.3690 (6)	0.070 (2)
H13A	0.0573	0.0224	0.3811	0.105*
H13B	−0.0487	0.0803	0.3014	0.105*
H13C	−0.0592	0.0786	0.4062	0.105*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0729 (5)	0.0613 (5)	0.0558 (5)	0.0189 (4)	0.0090 (4)	0.0111 (4)
Br2	0.0474 (4)	0.1006 (7)	0.0659 (6)	0.0050 (4)	0.0208 (4)	0.0021 (5)
O2	0.051 (3)	0.054 (3)	0.055 (3)	0.000 (2)	0.002 (3)	−0.002 (2)
N2	0.037 (3)	0.030 (3)	0.046 (3)	0.000 (2)	0.010 (3)	−0.001 (2)
N3	0.035 (3)	0.036 (3)	0.048 (4)	0.000 (3)	0.008 (3)	−0.001 (3)
C10	0.039 (4)	0.046 (4)	0.053 (5)	−0.010 (3)	0.009 (3)	−0.004 (3)
C16	0.035 (3)	0.038 (4)	0.040 (4)	0.001 (3)	0.014 (3)	−0.002 (3)
O3	0.068 (3)	0.054 (3)	0.069 (4)	0.009 (3)	0.009 (3)	0.006 (3)
C11	0.037 (3)	0.034 (4)	0.041 (4)	−0.001 (3)	0.008 (3)	−0.005 (3)
O1	0.042 (3)	0.053 (3)	0.063 (3)	0.009 (2)	−0.001 (3)	0.003 (3)
C8	0.039 (4)	0.039 (4)	0.043 (4)	0.006 (3)	0.011 (3)	0.004 (3)
N1	0.032 (3)	0.038 (3)	0.052 (4)	0.003 (2)	0.004 (3)	0.000 (3)
C18	0.041 (4)	0.050 (5)	0.051 (5)	−0.004 (4)	0.017 (4)	−0.003 (4)
C6	0.044 (4)	0.041 (4)	0.037 (4)	0.009 (3)	0.014 (3)	0.002 (3)
N4	0.047 (3)	0.038 (3)	0.045 (4)	−0.008 (3)	0.013 (3)	−0.006 (3)
C5	0.041 (4)	0.041 (4)	0.057 (5)	0.005 (3)	0.012 (3)	0.017 (3)
C12	0.044 (4)	0.042 (4)	0.050 (4)	−0.006 (3)	0.022 (3)	−0.007 (3)
C3	0.077 (5)	0.042 (5)	0.064 (5)	0.006 (4)	0.007 (4)	0.004 (4)
C7	0.037 (4)	0.049 (4)	0.044 (5)	0.005 (3)	0.008 (3)	0.008 (3)
C21	0.047 (4)	0.052 (5)	0.042 (4)	0.003 (4)	0.012 (4)	0.002 (4)
C15	0.042 (3)	0.041 (4)	0.035 (4)	0.004 (3)	0.009 (3)	−0.001 (3)
C1	0.046 (4)	0.044 (4)	0.063 (5)	0.006 (4)	0.004 (4)	0.007 (4)
C4	0.054 (5)	0.066 (6)	0.062 (6)	0.027 (4)	0.011 (4)	0.018 (4)
C19	0.042 (4)	0.046 (4)	0.051 (5)	−0.004 (3)	0.015 (3)	−0.005 (3)
C14	0.050 (4)	0.029 (4)	0.063 (5)	−0.002 (3)	0.023 (4)	−0.006 (3)
C2	0.062 (5)	0.050 (5)	0.078 (6)	0.001 (4)	−0.006 (4)	0.000 (4)
C17	0.043 (3)	0.036 (4)	0.052 (5)	0.006 (3)	0.001 (3)	0.000 (3)
C9	0.037 (3)	0.046 (5)	0.056 (5)	−0.002 (3)	0.012 (3)	−0.001 (4)
C20	0.046 (4)	0.062 (5)	0.051 (5)	−0.005 (4)	0.006 (4)	−0.007 (4)
C13	0.056 (5)	0.059 (5)	0.093 (7)	−0.009 (4)	0.023 (5)	−0.013 (4)

Geometric parameters (Å, º)

Br1—C17	1.918 (6)	C5—C4	1.359 (9)
Br2—C17	1.950 (7)	C5—H5A	0.9300
O2—C18	1.213 (7)	C12—C14	1.372 (8)
N2—C8	1.330 (7)	C12—C13	1.513 (9)
N2—C16	1.348 (7)	C3—C2	1.373 (10)
N3—C15	1.312 (7)	C3—C4	1.375 (10)
N3—C16	1.372 (7)	C3—H3B	0.9300
C10—C9	1.366 (8)	C21—C20	1.505 (9)
C10—C11	1.415 (8)	C15—C14	1.399 (8)
C10—H10A	0.9300	C15—C17	1.524 (8)
C16—C11	1.424 (8)	C1—C2	1.379 (9)
O3—C21	1.211 (7)	C1—H1B	0.9300
C11—C12	1.408 (8)	C4—H4B	0.9300
O1—C7	1.225 (7)	C19—C20	1.529 (8)
C8—N1	1.390 (7)	C19—H19A	0.9700
C8—C9	1.410 (8)	C19—H19B	0.9700
N1—C7	1.383 (7)	C14—H14A	0.9300
N1—H1A	0.8600	C2—H2B	0.9300
C18—N4	1.389 (8)	C17—H17A	0.9800
C18—C19	1.485 (9)	C9—H9A	0.9300
C6—C5	1.385 (8)	C20—H20A	0.9700
C6—C1	1.396 (9)	C20—H20B	0.9700
C6—C7	1.505 (8)	C13—H13A	0.9600
N4—C21	1.370 (8)	C13—H13B	0.9600
N4—H4A	0.8600	C13—H13C	0.9600
C8—N2—C16	118.2 (5)	N3—C15—C17	112.3 (5)
C15—N3—C16	116.9 (5)	C14—C15—C17	123.4 (6)
C9—C10—C11	120.5 (6)	C2—C1—C6	120.1 (6)
C9—C10—H10A	119.8	C2—C1—H1B	119.9
C11—C10—H10A	119.8	C6—C1—H1B	119.9
N2—C16—N3	113.7 (5)	C5—C4—C3	121.7 (7)
N2—C16—C11	123.7 (5)	C5—C4—H4B	119.2
N3—C16—C11	122.6 (5)	C3—C4—H4B	119.2
C12—C11—C10	125.9 (6)	C18—C19—C20	105.4 (5)
C12—C11—C16	118.2 (5)	C18—C19—H19A	110.7
C10—C11—C16	115.9 (5)	C20—C19—H19A	110.7
N2—C8—N1	112.4 (5)	C18—C19—H19B	110.7
N2—C8—C9	122.8 (6)	C20—C19—H19B	110.7
N1—C8—C9	124.8 (5)	H19A—C19—H19B	108.8
C7—N1—C8	128.3 (5)	C12—C14—C15	120.1 (6)
C7—N1—H1A	115.8	C12—C14—H14A	119.9
C8—N1—H1A	115.8	C15—C14—H14A	119.9
O2—C18—N4	125.0 (6)	C3—C2—C1	120.1 (7)
O2—C18—C19	127.0 (6)	C3—C2—H2B	120.0
N4—C18—C19	107.9 (6)	C1—C2—H2B	120.0
C5—C6—C1	119.1 (6)	C15—C17—Br1	114.3 (5)
C5—C6—C7	116.6 (6)	C15—C17—Br2	108.3 (4)
C1—C6—C7	124.3 (6)	Br1—C17—Br2	110.3 (3)
C21—N4—C18	113.9 (6)	C15—C17—H17A	107.9
C21—N4—H4A	123.0	Br1—C17—H17A	107.9
C18—N4—H4A	123.0	Br2—C17—H17A	107.9
C4—C5—C6	119.7 (6)	C10—C9—C8	118.9 (6)
C4—C5—H5A	120.1	C10—C9—H9A	120.5
C6—C5—H5A	120.1	C8—C9—H9A	120.5
C14—C12—C11	117.9 (6)	C21—C20—C19	105.0 (5)
C14—C12—C13	120.4 (6)	C21—C20—H20A	110.8
C11—C12—C13	121.7 (6)	C19—C20—H20A	110.8
C2—C3—C4	119.3 (7)	C21—C20—H20B	110.8
C2—C3—H3B	120.3	C19—C20—H20B	110.8
C4—C3—H3B	120.3	H20A—C20—H20B	108.8
O1—C7—N1	122.0 (6)	C12—C13—H13A	109.5
O1—C7—C6	121.1 (6)	C12—C13—H13B	109.5
N1—C7—C6	116.8 (6)	H13A—C13—H13B	109.5
O3—C21—N4	124.9 (6)	C12—C13—H13C	109.5
O3—C21—C20	127.3 (7)	H13A—C13—H13C	109.5
N4—C21—C20	107.8 (6)	H13B—C13—H13C	109.5
N3—C15—C14	124.4 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.86	2.22	3.060 (7)	164
N4—H4A···N2	0.86	2.48	3.195 (7)	141
N4—H4A···N3	0.86	2.27	3.098 (7)	162
C1—H1B···O2	0.93	2.43	3.299 (8)	156
C9—H9A···O1	0.93	2.30	2.870 (8)	119
C17—H17A···O3	0.98	2.60	3.504 (8)	154
C19—H19B···N3^i	0.97	2.58	3.538 (8)	170

Symmetry code: (i) −x+1, −y+1, −z+1.