1-(2-Bromo-1-methyl-1H-indol-3-ylcarbon­yl)pyrrolidine

In the title compound, C₁₄H₁₅BrN₂O, the pyrrolidine ring adopts a twist conformation. The amide group is twisted out of π-conjugation with the pyrrole double bond due to steric hindrance by the Br atom.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.016 Å
• R factor = 0.074
• wR factor = 0.277
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT026_ALERT_3_A Ratio Observed / Unique Reflections too Low ....         29 Perc.

Author Response: ...Data was collected on an old Rigaku AFC6S diffractometer.

Alert level B
PLAT341_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         16

Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.277
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.93
PLAT084_ALERT_2_C High R2 Value ..................................       0.28
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)        3000 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.21 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    Br1    -   C2      ..       6.83 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C13
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C2

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.932
            Tmax scaled      0.534 Tmin scaled      0.342
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           27.50
           From the CIF: _reflns_number_total               2850
           From the CIF: _diffrn_reflns_limit_ max hkl    8.   10.   13.
           From the CIF: _diffrn_reflns_limit_ min hkl   -9.    0.  -13.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl    9.   12.   13.
           Calculated minimum hkl   -9.  -12.  -13.

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994)'; cell refinement: MSC/AFC Diffractometer Control Software; data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

1-(2-Bromo-1-methylindol-3-ylcarbonyl)pyrrolidine

Crystal data

C14H15BrN2O	Z = 2
Mr = 307.19	F(000) = 312
Triclinic, P1	Dx = 1.564 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 7.327 (2) Å	Cell parameters from 20 reflections
b = 9.387 (3) Å	θ = 6.2–12.3°
c = 10.412 (4) Å	µ = 3.14 mm^−1
α = 96.14 (3)°	T = 296 K
β = 100.94 (3)°	Prism, colorless
γ = 109.32 (3)°	0.40 × 0.30 × 0.20 mm
V = 652.3 (4) Å^3

Data collection

Rigaku AFC-6S diffractometer	833 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 27.5°, θmin = 2.3°
ω/2θ scans	h = −9→8
Absorption correction: ψ scan (North et al., 1968)	k = 0→10
Tmin = 0.367, Tmax = 0.572	l = −13→13
2850 measured reflections	3 standard reflections every 150 reflections
2850 independent reflections	intensity decay: none

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.277	All H-atom parameters refined
S = 1.07	w = 1/[σ^2(Fo^2) + (0.1102P)^2] where P = (Fo^2 + 2Fc^2)/3
2850 reflections	(Δ/σ)max = 0.001
164 parameters	Δρmax = 0.62 e Å^−3
18 restraints	Δρmin = −0.46 e Å^−3

Special details

Experimental. ¹H-NMR (300 MHz, CDCl₃) δ 7.54 (d, 1H, J = 8.1 Hz), 7.29 (d, 1H, J = 8.3 Hz), 7.23 (td, 1H, J' = 7.6 Hz, J" = 1.0 Hz), 7.15 (td, 1H, J' = 7.6 Hz, J" = 1.2 Hz), 3.76 (s, 3H), 3.74 (t, 2H, J = 6.6 Hz), 3.41 (t, 2H, J = 6.6 Hz), 2.00 (m, 2H), 1.87 (m, 2H); ¹³C-NMR (CDCl₃) δ 164.7, 136.2, 125.1, 122.5, 121.0, 120.8, 119.7, 119.4, 109.6, 48.3, 45.8, 31.5, 30.2, 25.9, 24.6; IR ν(KBr)/cm^-1 3456, 2922, 2856, 1733, 1622, 1528, 1461, 1417, 1333, 750 cm^-1; λ_max/nm 286, 290, 298 nm; m/z 308 (M⁺), 262, 236, 192 (100%), 158, 129; HRMS: Calc. m/z 306.0368, Found m/z 306.0367.

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
Br1	0.2327 (2)	−0.01076 (18)	−0.04977 (16)	0.0798 (7)
O1	0.3536 (11)	0.0197 (8)	0.2872 (7)	0.044 (2)
N1	0.2401 (11)	0.2864 (9)	−0.0049 (7)	0.029 (2)
N2	0.6651 (11)	0.1944 (8)	0.3359 (8)	0.029 (2)
C2	0.2971 (13)	0.1805 (10)	0.0494 (9)	0.026 (2)
C3	0.4047 (14)	0.2299 (11)	0.1788 (9)	0.030 (2)
C4	0.4173 (13)	0.3891 (10)	0.2060 (10)	0.024 (2)
C5	0.4961 (14)	0.5020 (11)	0.3221 (10)	0.034 (3)
H1	0.5641	0.4832	0.3995	0.041*
C6	0.4717 (16)	0.6383 (12)	0.3199 (13)	0.047 (3)
H2	0.5253	0.7142	0.3959	0.056*
C7	0.3692 (18)	0.6660 (13)	0.2070 (15)	0.059 (4)
H3	0.3504	0.7594	0.2097	0.070*
C8	0.2962 (16)	0.5658 (15)	0.0949 (14)	0.054 (3)
H4	0.2339	0.5910	0.0189	0.065*
C9	0.3132 (14)	0.4164 (12)	0.0904 (11)	0.035 (3)
C10	0.1237 (16)	0.2700 (14)	−0.1407 (10)	0.046 (3)
H5	0.2123	0.2982	−0.1984	0.055*
H6	0.0475	0.3358	−0.1406	0.055*
H7	0.0352	0.1653	−0.1717	0.055*
C11	0.4698 (13)	0.1377 (11)	0.2699 (9)	0.025 (2)
C12	0.7412 (15)	0.1134 (12)	0.4303 (11)	0.046 (3)
H8	0.7297	0.0129	0.3870	0.055*
H9	0.6712	0.1012	0.5010	0.055*
C13	0.9584 (17)	0.2172 (16)	0.4836 (15)	0.078 (4)
H10	0.9739	0.2896	0.5623	0.093*
H11	1.0408	0.1570	0.5064	0.093*
C14	1.0141 (15)	0.2979 (15)	0.3760 (13)	0.059 (4)
H12	1.0587	0.2380	0.3157	0.070*
H13	1.1196	0.3970	0.4114	0.070*
C15	0.8266 (14)	0.3168 (11)	0.3063 (10)	0.036 (3)
H14	0.8247	0.4167	0.3397	0.043*
H15	0.8154	0.3064	0.2112	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0709 (11)	0.0725 (11)	0.0752 (11)	0.0192 (8)	−0.0015 (7)	−0.0176 (8)
O1	0.042 (4)	0.032 (4)	0.042 (5)	−0.002 (4)	−0.004 (4)	0.018 (3)
N1	0.026 (5)	0.034 (5)	0.023 (5)	0.008 (4)	0.002 (4)	0.004 (4)
N2	0.022 (4)	0.024 (5)	0.035 (5)	0.001 (4)	0.000 (4)	0.015 (4)
C2	0.022 (5)	0.024 (6)	0.031 (6)	0.012 (4)	0.007 (4)	−0.007 (5)
C3	0.030 (6)	0.031 (6)	0.019 (5)	0.003 (5)	0.003 (4)	−0.005 (4)
C4	0.017 (5)	0.019 (5)	0.039 (6)	0.005 (4)	0.016 (5)	0.007 (4)
C5	0.027 (6)	0.032 (7)	0.037 (6)	0.004 (5)	0.011 (5)	0.001 (5)
C6	0.037 (7)	0.028 (7)	0.069 (8)	0.003 (5)	0.021 (6)	−0.001 (6)
C7	0.049 (7)	0.019 (6)	0.104 (10)	0.009 (5)	0.021 (7)	−0.001 (7)
C8	0.033 (6)	0.065 (8)	0.082 (9)	0.026 (6)	0.016 (6)	0.050 (7)
C9	0.023 (6)	0.044 (7)	0.046 (7)	0.012 (5)	0.016 (5)	0.019 (6)
C10	0.041 (7)	0.069 (8)	0.037 (7)	0.029 (6)	0.008 (5)	0.022 (6)
C11	0.022 (5)	0.027 (6)	0.022 (5)	0.010 (5)	−0.007 (4)	0.000 (4)
C12	0.037 (6)	0.036 (6)	0.053 (7)	0.003 (5)	−0.003 (6)	0.017 (6)
C13	0.041 (8)	0.076 (10)	0.090 (11)	0.009 (7)	−0.025 (8)	0.025 (9)
C14	0.025 (7)	0.069 (9)	0.070 (9)	0.007 (6)	−0.003 (6)	0.020 (7)
C15	0.036 (6)	0.038 (6)	0.030 (6)	0.008 (5)	0.009 (5)	0.005 (5)

Geometric parameters (Å, º)

Br1—C2	1.836 (8)	C7—H3	0.93
O1—C11	1.209 (11)	C8—C9	1.446 (16)
N1—C2	1.337 (12)	C8—H4	0.93
N1—C9	1.366 (12)	C10—H5	0.96
N1—C10	1.469 (12)	C10—H6	0.96
N2—C11	1.359 (11)	C10—H7	0.96
N2—C12	1.445 (13)	C12—C13	1.521 (15)
N2—C15	1.459 (12)	C12—H8	0.97
C2—C3	1.369 (12)	C12—H9	0.97
C3—C4	1.460 (13)	C13—C14	1.465 (17)
C3—C11	1.467 (14)	C13—H10	0.97
C4—C9	1.394 (14)	C13—H11	0.97
C4—C5	1.406 (13)	C14—C15	1.502 (14)
C5—C6	1.351 (14)	C14—H12	0.97
C5—H1	0.93	C14—H13	0.97
C6—C7	1.368 (17)	C15—H14	0.97
C6—H2	0.93	C15—H15	0.97
C7—C8	1.314 (17)
C2—N1—C9	106.7 (8)	H5—C10—H6	109.5
C2—N1—C10	127.6 (8)	N1—C10—H7	109.5
C9—N1—C10	125.7 (9)	H5—C10—H7	109.5
C11—N2—C12	120.3 (8)	H6—C10—H7	109.5
C11—N2—C15	127.4 (8)	O1—C11—N2	122.3 (9)
C12—N2—C15	111.3 (8)	O1—C11—C3	121.2 (8)
N1—C2—C3	114.2 (8)	N2—C11—C3	116.5 (9)
N1—C2—Br1	120.0 (7)	N2—C12—C13	103.2 (9)
C3—C2—Br1	125.8 (8)	N2—C12—H8	111.1
C2—C3—C4	102.9 (8)	C13—C12—H8	111.1
C2—C3—C11	127.4 (9)	N2—C12—H9	111.1
C4—C3—C11	129.4 (8)	C13—C12—H9	111.1
C9—C4—C5	120.6 (9)	H8—C12—H9	109.1
C9—C4—C3	106.8 (8)	C14—C13—C12	105.7 (10)
C5—C4—C3	132.4 (9)	C14—C13—H10	110.6
C6—C5—C4	119.1 (11)	C12—C13—H10	110.6
C6—C5—H1	120.5	C14—C13—H11	110.6
C4—C5—H1	120.5	C12—C13—H11	110.6
C5—C6—C7	120.8 (11)	H10—C13—H11	108.7
C5—C6—H2	119.6	C13—C14—C15	104.5 (9)
C7—C6—H2	119.6	C13—C14—H12	110.9
C8—C7—C6	122.6 (11)	C15—C14—H12	110.9
C8—C7—H3	118.7	C13—C14—H13	110.9
C6—C7—H3	118.7	C15—C14—H13	110.9
C7—C8—C9	119.7 (11)	H12—C14—H13	108.9
C7—C8—H4	120.2	N2—C15—C14	105.0 (9)
C9—C8—H4	120.2	N2—C15—H14	110.7
N1—C9—C4	109.4 (9)	C14—C15—H14	110.7
N1—C9—C8	133.4 (11)	N2—C15—H15	110.7
C4—C9—C8	117.2 (10)	C14—C15—H15	110.7
N1—C10—H5	109.5	H14—C15—H15	108.8
N1—C10—H6	109.5