2,5-Bis[(di­methyl­amino)­methyl]-1H-pyrrole

The asymmetric unit contains two independent mol­ecules, C₁₀H₁₉N₃, which are linked into dimers by two N_pyrrole—H...N_amine hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.048
• wR factor = 0.120
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         N6 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.002 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min)           6 Note
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.596         15 Report
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 !
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          70 %

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

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

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Computing details

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); 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: PLATON (Spek, 2009).

2,5-Bis[(dimethylamino)methyl]-1H-pyrrole

Crystal data

C10H19N3	F(000) = 800
Mr = 181.28	Dx = 1.036 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9945 reflections
a = 9.8203 (4) Å	θ = 2.9–28.3°
b = 10.6193 (4) Å	µ = 0.06 mm^−1
c = 22.5202 (9) Å	T = 200 K
β = 98.098 (1)°	Block, colorless
V = 2325.09 (16) Å^3	0.25 × 0.20 × 0.20 mm
Z = 8

Data collection

Bruker APEXII CCD diffractometer	4102 independent reflections
Radiation source: fine-focus sealed tube	3463 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 25.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −11→9
Tmin = 0.984, Tmax = 0.987	k = −12→12
16645 measured reflections	l = −26→26

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.055P)^2 + 0.774P] where P = (Fo^2 + 2Fc^2)/3
4102 reflections	(Δ/σ)max < 0.001
251 parameters	Δρmax = 0.14 e Å^−3
0 restraints	Δρmin = −0.29 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
N1	0.51916 (12)	0.27259 (11)	0.49505 (5)	0.0330 (3)
N2	0.46921 (11)	0.18139 (10)	0.35956 (5)	0.0329 (3)
N3	0.66223 (13)	0.33577 (11)	0.62140 (5)	0.0406 (3)
N4	0.73647 (12)	0.30961 (11)	0.34942 (5)	0.0349 (3)
N5	0.57265 (13)	0.37168 (13)	0.22458 (5)	0.0462 (3)
N6	0.81107 (12)	0.21866 (12)	0.48359 (5)	0.0380 (3)
C1	0.41230 (14)	0.20883 (14)	0.46275 (6)	0.0373 (3)
C2	0.29505 (15)	0.24217 (17)	0.48545 (7)	0.0490 (4)
H2	0.2046	0.2133	0.4716	0.059*
C3	0.33301 (15)	0.32738 (17)	0.53326 (7)	0.0485 (4)
H3	0.2727	0.3657	0.5574	0.058*
C4	0.47210 (14)	0.34452 (14)	0.53839 (6)	0.0372 (3)
C5	0.56728 (15)	0.41779 (14)	0.58293 (6)	0.0396 (3)
H5A	0.6209	0.4771	0.5614	0.047*
H5B	0.5128	0.4679	0.6082	0.047*
C6	0.5889 (2)	0.25212 (16)	0.65700 (8)	0.0590 (5)
H6A	0.6549	0.1973	0.6814	0.088*
H6B	0.5240	0.2005	0.6303	0.088*
H6C	0.5385	0.3022	0.6833	0.088*
C7	0.76343 (19)	0.40912 (16)	0.66004 (7)	0.0552 (4)
H7A	0.7171	0.4591	0.6879	0.083*
H7B	0.8115	0.4655	0.6355	0.083*
H7C	0.8300	0.3523	0.6829	0.083*
C8	0.43384 (16)	0.11967 (14)	0.41380 (6)	0.0393 (3)
H8A	0.5085	0.0605	0.4291	0.047*
H8B	0.3489	0.0697	0.4029	0.047*
C9	0.50189 (17)	0.08705 (14)	0.31653 (7)	0.0451 (4)
H9A	0.4207	0.0348	0.3040	0.068*
H9B	0.5774	0.0338	0.3353	0.068*
H9C	0.5295	0.1293	0.2814	0.068*
C10	0.35561 (16)	0.25880 (15)	0.33159 (7)	0.0439 (4)
H10A	0.3820	0.3005	0.2961	0.066*
H10B	0.3334	0.3225	0.3602	0.066*
H10C	0.2750	0.2055	0.3196	0.066*
C11	0.85627 (14)	0.26252 (15)	0.37998 (6)	0.0404 (4)
C12	0.96231 (16)	0.3169 (2)	0.35660 (8)	0.0666 (6)
H12	1.0575	0.3025	0.3692	0.080*
C13	0.90529 (18)	0.3985 (2)	0.31040 (8)	0.0707 (6)
H13	0.9554	0.4485	0.2860	0.085*
C14	0.76571 (16)	0.39331 (15)	0.30672 (7)	0.0458 (4)
C15	0.65633 (17)	0.45768 (16)	0.26511 (7)	0.0476 (4)
H15A	0.5956	0.5042	0.2890	0.057*
H15B	0.6998	0.5200	0.2410	0.057*
C16	0.6545 (2)	0.3079 (2)	0.18498 (9)	0.0700 (5)
H16A	0.6931	0.3700	0.1599	0.105*
H16B	0.5962	0.2488	0.1594	0.105*
H16C	0.7293	0.2617	0.2089	0.105*
C17	0.46052 (19)	0.4411 (2)	0.18979 (8)	0.0663 (5)
H17A	0.4985	0.5057	0.1657	0.099*
H17B	0.4043	0.4814	0.2171	0.099*
H17C	0.4034	0.3829	0.1632	0.099*
C18	0.85787 (15)	0.16923 (14)	0.42902 (6)	0.0393 (3)
H18A	0.7985	0.0973	0.4142	0.047*
H18B	0.9528	0.1369	0.4395	0.047*
C19	0.8157 (2)	0.11775 (19)	0.52785 (8)	0.0661 (6)
H19A	0.9108	0.0889	0.5385	0.099*
H19B	0.7583	0.0474	0.5109	0.099*
H19C	0.7811	0.1492	0.5638	0.099*
C20	0.89513 (18)	0.3249 (2)	0.50799 (8)	0.0625 (5)
H20A	0.8625	0.3548	0.5447	0.094*
H20B	0.8881	0.3931	0.4784	0.094*
H20C	0.9913	0.2981	0.5173	0.094*
H20	0.6493 (17)	0.2851 (14)	0.3558 (7)	0.043 (4)*
H21	0.6060 (17)	0.2653 (14)	0.4890 (7)	0.041 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0285 (6)	0.0417 (7)	0.0296 (6)	−0.0026 (5)	0.0065 (5)	−0.0023 (5)
N2	0.0341 (6)	0.0344 (6)	0.0313 (6)	−0.0056 (5)	0.0089 (5)	−0.0064 (5)
N3	0.0475 (7)	0.0375 (6)	0.0351 (6)	0.0031 (5)	−0.0001 (5)	−0.0050 (5)
N4	0.0295 (6)	0.0445 (7)	0.0308 (6)	−0.0035 (5)	0.0047 (5)	0.0056 (5)
N5	0.0467 (7)	0.0568 (8)	0.0343 (7)	−0.0057 (6)	0.0025 (5)	0.0107 (6)
N6	0.0340 (6)	0.0474 (7)	0.0332 (6)	0.0068 (5)	0.0077 (5)	0.0083 (5)
C1	0.0342 (7)	0.0474 (8)	0.0307 (7)	−0.0086 (6)	0.0063 (6)	−0.0022 (6)
C2	0.0313 (7)	0.0744 (11)	0.0421 (8)	−0.0096 (7)	0.0081 (6)	−0.0073 (8)
C3	0.0383 (8)	0.0698 (11)	0.0399 (8)	0.0049 (8)	0.0137 (6)	−0.0077 (8)
C4	0.0403 (8)	0.0431 (8)	0.0288 (7)	0.0023 (6)	0.0072 (6)	−0.0020 (6)
C5	0.0484 (8)	0.0382 (8)	0.0316 (7)	0.0022 (6)	0.0038 (6)	−0.0024 (6)
C6	0.0730 (12)	0.0494 (10)	0.0539 (10)	0.0039 (9)	0.0066 (9)	0.0128 (8)
C7	0.0630 (11)	0.0518 (10)	0.0453 (9)	0.0061 (8)	−0.0117 (8)	−0.0119 (8)
C8	0.0445 (8)	0.0400 (8)	0.0342 (7)	−0.0105 (6)	0.0080 (6)	−0.0033 (6)
C9	0.0548 (9)	0.0420 (8)	0.0406 (8)	−0.0034 (7)	0.0141 (7)	−0.0112 (7)
C10	0.0435 (8)	0.0469 (8)	0.0410 (8)	0.0006 (7)	0.0053 (7)	−0.0030 (7)
C11	0.0307 (7)	0.0562 (9)	0.0345 (7)	−0.0002 (6)	0.0057 (6)	0.0080 (7)
C12	0.0313 (8)	0.1101 (16)	0.0584 (11)	−0.0065 (9)	0.0062 (7)	0.0342 (11)
C13	0.0435 (9)	0.1081 (16)	0.0603 (11)	−0.0204 (10)	0.0060 (8)	0.0423 (11)
C14	0.0438 (8)	0.0559 (9)	0.0367 (8)	−0.0095 (7)	0.0025 (6)	0.0136 (7)
C15	0.0535 (9)	0.0504 (9)	0.0375 (8)	−0.0030 (7)	0.0015 (7)	0.0110 (7)
C16	0.0836 (14)	0.0752 (13)	0.0530 (11)	−0.0044 (11)	0.0158 (10)	−0.0043 (10)
C17	0.0569 (10)	0.0914 (14)	0.0467 (10)	−0.0045 (10)	−0.0065 (8)	0.0234 (10)
C18	0.0353 (7)	0.0477 (8)	0.0357 (7)	0.0070 (6)	0.0077 (6)	0.0066 (6)
C19	0.0795 (13)	0.0785 (13)	0.0444 (9)	0.0340 (11)	0.0229 (9)	0.0284 (9)
C20	0.0444 (9)	0.0851 (13)	0.0582 (11)	−0.0051 (9)	0.0077 (8)	−0.0207 (10)

Geometric parameters (Å, º)

N1—C1	1.3689 (17)	C7—H7C	0.9800
N1—C4	1.3700 (17)	C8—H8A	0.9900
N1—H21	0.886 (17)	C8—H8B	0.9900
N2—C10	1.4557 (18)	C9—H9A	0.9800
N2—C9	1.4605 (17)	C9—H9B	0.9800
N2—C8	1.4704 (17)	C9—H9C	0.9800
N3—C7	1.4519 (19)	C10—H10A	0.9800
N3—C6	1.453 (2)	C10—H10B	0.9800
N3—C5	1.4666 (18)	C10—H10C	0.9800
N4—C11	1.3710 (18)	C11—C12	1.360 (2)
N4—C14	1.3693 (18)	C11—C18	1.4820 (19)
N4—H20	0.926 (16)	C12—C13	1.408 (2)
N5—C16	1.450 (2)	C12—H12	0.9500
N5—C15	1.460 (2)	C13—C14	1.363 (2)
N5—C17	1.458 (2)	C13—H13	0.9500
N6—C19	1.4599 (19)	C14—C15	1.489 (2)
N6—C20	1.459 (2)	C15—H15A	0.9900
N6—C18	1.4683 (17)	C15—H15B	0.9900
C1—C2	1.370 (2)	C16—H16A	0.9800
C1—C8	1.4906 (19)	C16—H16B	0.9800
C2—C3	1.416 (2)	C16—H16C	0.9800
C2—H2	0.9500	C17—H17A	0.9800
C3—C4	1.367 (2)	C17—H17B	0.9800
C3—H3	0.9500	C17—H17C	0.9800
C4—C5	1.4903 (19)	C18—H18A	0.9900
C5—H5A	0.9900	C18—H18B	0.9900
C5—H5B	0.9900	C19—H19A	0.9800
C6—H6A	0.9800	C19—H19B	0.9800
C6—H6B	0.9800	C19—H19C	0.9800
C6—H6C	0.9800	C20—H20A	0.9800
C7—H7A	0.9800	C20—H20B	0.9800
C7—H7B	0.9800	C20—H20C	0.9800
C1—N1—C4	110.12 (12)	N2—C9—H9C	109.5
C1—N1—H21	123.9 (10)	H9A—C9—H9C	109.5
C4—N1—H21	126.0 (10)	H9B—C9—H9C	109.5
C10—N2—C9	109.09 (11)	N2—C10—H10A	109.5
C10—N2—C8	110.78 (11)	N2—C10—H10B	109.5
C9—N2—C8	110.19 (11)	H10A—C10—H10B	109.5
C7—N3—C6	110.34 (13)	N2—C10—H10C	109.5
C7—N3—C5	111.10 (12)	H10A—C10—H10C	109.5
C6—N3—C5	111.45 (13)	H10B—C10—H10C	109.5
C11—N4—C14	109.83 (12)	C12—C11—N4	107.49 (13)
C11—N4—H20	124.5 (10)	C12—C11—C18	130.10 (14)
C14—N4—H20	125.6 (10)	N4—C11—C18	122.42 (12)
C16—N5—C15	111.41 (14)	C11—C12—C13	107.51 (14)
C16—N5—C17	110.36 (14)	C11—C12—H12	126.2
C15—N5—C17	109.61 (14)	C13—C12—H12	126.2
C19—N6—C20	110.40 (14)	C14—C13—C12	108.17 (14)
C19—N6—C18	109.01 (12)	C14—C13—H13	125.9
C20—N6—C18	111.38 (12)	C12—C13—H13	125.9
C2—C1—N1	107.18 (13)	C13—C14—N4	106.99 (13)
C2—C1—C8	130.86 (13)	C13—C14—C15	130.55 (14)
N1—C1—C8	121.94 (12)	N4—C14—C15	122.42 (13)
C1—C2—C3	107.69 (13)	N5—C15—C14	113.52 (13)
C1—C2—H2	126.2	N5—C15—H15A	108.9
C3—C2—H2	126.2	C14—C15—H15A	108.9
C4—C3—C2	107.60 (13)	N5—C15—H15B	108.9
C4—C3—H3	126.2	C14—C15—H15B	108.9
C2—C3—H3	126.2	H15A—C15—H15B	107.7
C3—C4—N1	107.40 (13)	N5—C16—H16A	109.5
C3—C4—C5	130.62 (13)	N5—C16—H16B	109.5
N1—C4—C5	121.87 (12)	H16A—C16—H16B	109.5
N3—C5—C4	111.95 (12)	N5—C16—H16C	109.5
N3—C5—H5A	109.2	H16A—C16—H16C	109.5
C4—C5—H5A	109.2	H16B—C16—H16C	109.5
N3—C5—H5B	109.2	N5—C17—H17A	109.5
C4—C5—H5B	109.2	N5—C17—H17B	109.5
H5A—C5—H5B	107.9	H17A—C17—H17B	109.5
N3—C6—H6A	109.5	N5—C17—H17C	109.5
N3—C6—H6B	109.5	H17A—C17—H17C	109.5
H6A—C6—H6B	109.5	H17B—C17—H17C	109.5
N3—C6—H6C	109.5	N6—C18—C11	114.39 (12)
H6A—C6—H6C	109.5	N6—C18—H18A	108.7
H6B—C6—H6C	109.5	C11—C18—H18A	108.7
N3—C7—H7A	109.5	N6—C18—H18B	108.7
N3—C7—H7B	109.5	C11—C18—H18B	108.7
H7A—C7—H7B	109.5	H18A—C18—H18B	107.6
N3—C7—H7C	109.5	N6—C19—H19A	109.5
H7A—C7—H7C	109.5	N6—C19—H19B	109.5
H7B—C7—H7C	109.5	H19A—C19—H19B	109.5
N2—C8—C1	113.95 (11)	N6—C19—H19C	109.5
N2—C8—H8A	108.8	H19A—C19—H19C	109.5
C1—C8—H8A	108.8	H19B—C19—H19C	109.5
N2—C8—H8B	108.8	N6—C20—H20A	109.5
C1—C8—H8B	108.8	N6—C20—H20B	109.5
H8A—C8—H8B	107.7	H20A—C20—H20B	109.5
N2—C9—H9A	109.5	N6—C20—H20C	109.5
N2—C9—H9B	109.5	H20A—C20—H20C	109.5
H9A—C9—H9B	109.5	H20B—C20—H20C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H21···N6	0.886 (17)	2.094 (17)	2.9699 (16)	169.8 (14)
N4—H20···N2	0.926 (16)	2.095 (17)	2.9939 (16)	163.5 (14)