Vallesiachotamine

Vencato, I.; Silva, F.M. da; Oliveira, C.M.A. de; Kato, L.; Tanaka, C.M.A.; Silva, C.C. da; Sabino, J.R.

doi:10.1107/S1600536805041553

Vallesiachotamine

I. Vencato, F. M. da Silva, C. M. A. de Oliveira, L. Kato, C. M. A. Tanaka, C. C. da Silva and J. R. Sabino

The title compound, C₂₁H₂₂N₂O₃, (2S,12βS)-methyl 2-[(1E)-1-formyl-1-propenyl]-1,2,6,7,12,12b-hexahydroindolo[2,3-α]quinolizine-3-carboxylic acid, exhibits a rare vallesiachotamane skeleton. Intermolecular hydrogen bonding results in the formation of a chain.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805041553/tk6293sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805041553/tk6293Isup2.hkl Contains datablock I

CCDC reference: 298704

checkCIF report

Key indicators

Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.007 Å
R factor = 0.046
wR factor = 0.180
Data-to-parameter ratio = 7.4

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.90

Author Response: The intensities measurements were extended to theta(max)= 68.00 degrees but 200 reflections could not be measured due to scintillator-collimator collision predicted. The total reflections measured was 1844, but 19 were rejected after data reduction and refinement.


Alert level C
REFLT03_ALERT_1_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           67.90
           From the CIF: _diffrn_reflns_theta_full          67.90
           From the CIF: _reflns_number_total               1825
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         1955
           Completeness (_total/calc)             93.35%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.93
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.39
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.03 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.74 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

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           67.90
           From the CIF: _reflns_number_total               1825
           Count of symmetry unique reflns         1955
           Completeness (_total/calc)             93.35%
           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
   6 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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


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.

Author Response: In the present paper several Institutions are involved, and three different groups with graduation students of Chemisty, Crystallography and Biology. All the cited persons have contributed to the present paper, as described below:

  Extract obtention                                C.M.A.T.
  Isolation,                                       L.K.
  Spectrocopic analysis                            C.M.A.O., C.C.S.
  Biological activity                              F.M.S.
  Data collection                                  I.V.
  Solution, refinement, drawings                   J.R.S.
  Preparation of first CIF                         I.V.
  Improvements of the draft of submission          I.V., J.R.S., C.M.A.T.
  Submission and dealing with referees and proofs  I.V.



   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 top

Data collection: CAD-4-PC (Enraf–Nonius, 1993); cell refinement: CAD-4-PC; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(2S,12βS)-methyl 2-[(1E)-1-formyl-1-propenyl]-1,2,6,7,12,12b-hexahydroindolo[2,3-α]quinolizine- 3-carboxylic acid top

Crystal data top

C₂₁H₂₂N₂O₃	D_x = 1.262 Mg m⁻³
M_r = 350.41	Melting point = 250–251 K
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 7.194 (1) Å	θ = 15.1–30.9°
b = 9.859 (1) Å	µ = 0.69 mm⁻¹
c = 25.995 (6) Å	T = 297 K
V = 1843.7 (5) Å³	Block, brown
Z = 4	0.18 × 0.15 × 0.08 mm
F(000) = 744

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.023
Radiation source: fine-focus sealed tube	θ_max = 67.9°, θ_min = 3.4°
Graphite monochromator	h = 0→8
non–profiled ω/2θ scans	k = 0→11
1844 measured reflections	l = −1→31
1825 independent reflections	2 standard reflections every 120 min
1411 reflections with I > 2σ(I)	intensity decay: < 1%

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.046	w = 1/[σ²(F_o²) + (0.1038P)² + 0.2785P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.180	(Δ/σ)_max = 0.001
S = 1.23	Δρ_max = 0.34 e Å⁻³
1825 reflections	Δρ_min = −0.32 e Å⁻³
247 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0035 (9)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.0690 (6)	0.1755 (4)	0.07480 (16)	0.0610 (11)
O2	0.1367 (7)	0.4961 (6)	0.20929 (15)	0.0875 (17)
O3	−0.1581 (7)	0.4249 (6)	0.21388 (15)	0.0765 (14)
N1	−0.1308 (5)	0.5153 (4)	−0.06429 (15)	0.0407 (10)
H1	−0.235 (8)	0.454 (5)	−0.060 (2)	0.049*
C2	0.0080 (6)	0.5230 (5)	−0.02828 (18)	0.0378 (11)
C3	0.0060 (6)	0.4463 (5)	0.02088 (19)	0.0385 (11)
H3	0.047 (7)	0.339 (6)	0.0168 (18)	0.046*
N4	0.1463 (5)	0.5083 (5)	0.05499 (16)	0.0468 (11)
C5	0.3252 (6)	0.5401 (6)	0.0305 (2)	0.0546 (15)
H5A	0.3760	0.4583	0.0153	0.065*
H5B	0.4118	0.5715	0.0565	0.065*
C6	0.3048 (7)	0.6477 (6)	−0.0106 (2)	0.0558 (15)
H6A	0.2885	0.7360	0.0053	0.067*
H6B	0.4160	0.6506	−0.0317	0.067*
C7	0.1389 (6)	0.6148 (5)	−0.04349 (18)	0.0402 (11)
C8	0.0824 (7)	0.6653 (5)	−0.09289 (18)	0.0439 (12)
C9	0.1593 (9)	0.7551 (6)	−0.1287 (2)	0.0554 (15)
H9	0.2719	0.7982	−0.1222	0.066*
C10	0.0650 (10)	0.7779 (6)	−0.1735 (2)	0.0667 (18)
H10	0.1146	0.8380	−0.1974	0.080*
C11	−0.1040 (9)	0.7138 (7)	−0.1846 (2)	0.0659 (17)
H11	−0.1653	0.7327	−0.2153	0.079*
C12	−0.1787 (8)	0.6243 (6)	−0.1508 (2)	0.0550 (14)
H12	−0.2890	0.5795	−0.1584	0.066*
C13	−0.0872 (7)	0.6009 (5)	−0.10443 (19)	0.0450 (12)
C14	−0.1836 (6)	0.4477 (5)	0.04733 (17)	0.0387 (11)
H14A	−0.2675	0.3909	0.0276	0.046*
H14B	−0.2318	0.5395	0.0461	0.046*
C15	−0.1882 (6)	0.3996 (5)	0.10365 (18)	0.0404 (11)
H15	−0.2961	0.4441	0.1193	0.049*
C16	−0.0193 (7)	0.4539 (5)	0.13216 (19)	0.0446 (12)
C17	0.1298 (7)	0.5030 (6)	0.10590 (19)	0.0450 (12)
H17	0.229 (8)	0.548 (5)	0.123 (2)	0.054*
C18	−0.5303 (8)	0.2660 (8)	0.1573 (3)	0.0698 (18)
H18A	−0.4988	0.3583	0.1651	0.105*
H18B	−0.5684	0.2204	0.1882	0.105*
H18C	−0.6302	0.2644	0.1328	0.105*
C19	−0.3656 (7)	0.1960 (6)	0.1352 (2)	0.0505 (13)
H19	−0.3660	0.1020	0.1381	0.061*
C20	−0.2169 (7)	0.2490 (5)	0.11177 (18)	0.0403 (11)
C21	−0.0774 (7)	0.1514 (6)	0.0970 (2)	0.0493 (13)
H21	−0.1010	0.0612	0.1052	0.059*
C22	−0.0239 (8)	0.4563 (6)	0.1873 (2)	0.0540 (14)
C23	0.1407 (13)	0.5064 (11)	0.2635 (2)	0.115 (4)
H23A	0.0669	0.5825	0.2741	0.172*
H23B	0.2666	0.5189	0.2748	0.172*
H23C	0.0913	0.4249	0.2783	0.172*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.053 (2)	0.055 (2)	0.075 (2)	0.022 (2)	0.009 (2)	0.003 (2)
O2	0.080 (3)	0.135 (5)	0.047 (2)	−0.036 (4)	−0.010 (2)	−0.001 (3)
O3	0.073 (3)	0.106 (4)	0.050 (2)	−0.013 (3)	0.009 (2)	0.004 (2)
N1	0.0333 (19)	0.047 (2)	0.041 (2)	−0.004 (2)	−0.0015 (17)	0.003 (2)
C2	0.033 (2)	0.036 (2)	0.045 (2)	0.001 (2)	−0.003 (2)	−0.001 (2)
C3	0.029 (2)	0.044 (3)	0.042 (2)	−0.001 (2)	−0.005 (2)	−0.005 (2)
N4	0.0278 (18)	0.063 (3)	0.049 (2)	−0.002 (2)	−0.0071 (17)	−0.004 (2)
C5	0.026 (2)	0.085 (4)	0.053 (3)	−0.004 (3)	−0.004 (2)	−0.008 (3)
C6	0.037 (3)	0.072 (4)	0.057 (3)	−0.017 (3)	−0.002 (2)	−0.008 (3)
C7	0.036 (2)	0.043 (3)	0.042 (2)	−0.009 (2)	0.002 (2)	−0.010 (2)
C8	0.043 (3)	0.040 (3)	0.049 (3)	−0.004 (2)	0.000 (2)	−0.007 (2)
C9	0.064 (4)	0.047 (3)	0.055 (3)	−0.013 (3)	0.008 (3)	−0.001 (3)
C10	0.089 (5)	0.056 (4)	0.055 (3)	−0.006 (4)	0.009 (4)	0.001 (3)
C11	0.082 (4)	0.066 (4)	0.049 (3)	−0.001 (4)	−0.009 (3)	0.006 (3)
C12	0.056 (3)	0.059 (3)	0.050 (3)	−0.005 (3)	−0.009 (3)	−0.008 (3)
C13	0.040 (2)	0.046 (3)	0.049 (3)	0.002 (2)	−0.001 (2)	−0.002 (3)
C14	0.028 (2)	0.044 (3)	0.045 (2)	0.000 (2)	−0.0036 (19)	−0.003 (2)
C15	0.029 (2)	0.047 (3)	0.045 (2)	0.005 (2)	0.002 (2)	−0.002 (2)
C16	0.043 (3)	0.045 (3)	0.045 (3)	−0.001 (3)	−0.007 (2)	0.003 (3)
C17	0.038 (2)	0.055 (3)	0.042 (2)	−0.001 (3)	−0.008 (2)	−0.004 (3)
C18	0.044 (3)	0.087 (5)	0.078 (4)	−0.004 (3)	0.012 (3)	0.009 (4)
C19	0.043 (3)	0.059 (3)	0.049 (3)	−0.004 (3)	−0.008 (2)	0.006 (3)
C20	0.038 (2)	0.041 (3)	0.042 (2)	0.002 (2)	−0.008 (2)	−0.005 (2)
C21	0.047 (3)	0.047 (3)	0.054 (3)	0.005 (3)	−0.008 (3)	0.002 (3)
C22	0.057 (3)	0.051 (3)	0.055 (3)	−0.005 (3)	−0.004 (3)	0.007 (3)
C23	0.137 (8)	0.160 (9)	0.047 (3)	−0.047 (8)	−0.024 (4)	0.006 (5)

Geometric parameters (Å, º) top

O1—C21	1.225 (6)	C10—H10	0.9300
O2—C22	1.347 (7)	C11—C12	1.356 (8)
O2—C23	1.412 (7)	C11—H11	0.9300
O3—C22	1.228 (7)	C12—C13	1.392 (7)
N1—C2	1.370 (6)	C12—H12	0.9300
N1—C13	1.379 (6)	C14—C15	1.539 (7)
N1—H1	0.97 (5)	C14—H14A	0.9700
C2—C7	1.365 (6)	C14—H14B	0.9700
C2—C3	1.485 (7)	C15—C16	1.520 (7)
N4—C3	1.476 (6)	C15—C20	1.514 (7)
C3—H3	1.11 (5)	C15—H15	0.9800
N4—C5	1.469 (6)	C16—C17	1.360 (7)
N4—C17	1.330 (6)	C16—C22	1.433 (8)
C3—C14	1.527 (6)	C17—H17	0.95 (6)
C5—C6	1.514 (8)	C18—C19	1.487 (8)
C5—H5A	0.9700	C18—H18A	0.9600
C5—H5B	0.9700	C18—H18B	0.9600
C6—C7	1.503 (6)	C18—H18C	0.9600
C6—H6A	0.9700	C19—C20	1.337 (7)
C6—H6B	0.9700	C19—H19	0.9300
C7—C8	1.436 (7)	C20—C21	1.442 (7)
C8—C9	1.399 (7)	C21—H21	0.9300
C8—C13	1.407 (7)	C23—H23A	0.9600
C9—C10	1.366 (8)	C23—H23B	0.9600
C9—H9	0.9300	C23—H23C	0.9600
C10—C11	1.400 (8)

C22—O2—C23	117.5 (6)	N1—C13—C12	130.5 (5)
C2—N1—C13	108.5 (4)	N1—C13—C8	108.2 (4)
C2—N1—H1	122 (3)	C12—C13—C8	121.3 (5)
C13—N1—H1	130 (3)	C3—C14—C15	116.4 (4)
C7—C2—N1	110.0 (4)	C3—C14—H14A	108.2
C7—C2—C3	126.4 (4)	C15—C14—H14A	108.2
N1—C2—C3	123.5 (4)	C3—C14—H14B	108.2
N4—C3—C2	107.4 (4)	C15—C14—H14B	108.2
C2—C3—C14	113.0 (4)	H14A—C14—H14B	107.3
N4—C3—H3	106 (3)	C14—C15—C16	109.8 (4)
C2—C3—H3	114 (3)	C14—C15—C20	115.9 (4)
C14—C3—H3	107 (3)	C16—C15—C20	112.7 (4)
C3—N4—C5	115.3 (4)	C14—C15—H15	105.9
C3—N4—C17	121.4 (4)	C16—C15—H15	105.9
C5—N4—C17	121.1 (4)	C20—C15—H15	105.9
N4—C3—C14	109.7 (4)	C15—C16—C17	120.7 (4)
N4—C5—C6	111.7 (4)	C15—C16—C22	118.3 (5)
N4—C5—H5A	109.3	C17—C16—C22	120.9 (5)
C6—C5—H5A	109.3	N4—C17—C16	125.7 (5)
N4—C5—H5B	109.3	N4—C17—H17	112 (3)
C6—C5—H5B	109.3	C16—C17—H17	122 (3)
H5A—C5—H5B	107.9	C19—C18—H18A	109.5
C7—C6—C5	109.1 (4)	C19—C18—H18B	109.5
C7—C6—H6A	109.9	H18A—C18—H18B	109.5
C5—C6—H6A	109.9	C19—C18—H18C	109.5
C7—C6—H6B	109.9	H18A—C18—H18C	109.5
C5—C6—H6B	109.9	H18B—C18—H18C	109.5
H6A—C6—H6B	108.3	C20—C19—C18	129.2 (6)
C2—C7—C8	107.1 (4)	C20—C19—H19	115.4
C2—C7—C6	121.7 (4)	C18—C19—H19	115.4
C8—C7—C6	131.2 (5)	C19—C20—C21	114.7 (5)
C9—C8—C13	119.1 (5)	C19—C20—C15	123.8 (5)
C9—C8—C7	134.6 (5)	C21—C20—C15	121.5 (5)
C13—C8—C7	106.3 (4)	O1—C21—C20	126.5 (5)
C10—C9—C8	118.3 (6)	O1—C21—H21	116.7
C10—C9—H9	120.8	C20—C21—H21	116.7
C8—C9—H9	120.8	O3—C22—O2	120.5 (5)
C9—C10—C11	122.2 (6)	O3—C22—C16	125.3 (5)
C9—C10—H10	118.9	O2—C22—C16	114.2 (5)
C11—C10—H10	118.9	O2—C23—H23A	109.5
C12—C11—C10	120.3 (6)	O2—C23—H23B	109.5
C12—C11—H11	119.9	H23A—C23—H23B	109.5
C10—C11—H11	119.9	O2—C23—H23C	109.5
C11—C12—C13	118.8 (6)	H23A—C23—H23C	109.5
C11—C12—H12	120.6	H23B—C23—H23C	109.5
C13—C12—H12	120.6

C13—N1—C2—C7	1.6 (6)	C11—C12—C13—C8	−1.7 (8)
C13—N1—C2—C3	178.7 (4)	C9—C8—C13—N1	178.2 (5)
C7—C2—C3—N4	12.2 (7)	C7—C8—C13—N1	−0.3 (5)
N1—C2—C3—N4	−164.4 (4)	C9—C8—C13—C12	0.4 (7)
C7—C2—C3—C14	133.3 (5)	C7—C8—C13—C12	−178.2 (5)
N1—C2—C3—C14	−43.3 (6)	N4—C3—C14—C15	−46.7 (6)
C2—C3—N4—C17	152.3 (5)	C2—C3—C14—C15	−166.5 (4)
C14—C3—N4—C17	29.1 (7)	C3—C14—C15—C20	−88.7 (5)
C2—C3—N4—C5	−44.3 (6)	C3—C14—C15—C16	40.5 (6)
C14—C3—N4—C5	−167.5 (5)	C20—C15—C16—C17	114.5 (6)
C17—N4—C5—C6	−131.9 (5)	C14—C15—C16—C17	−16.4 (7)
C3—N4—C5—C6	64.7 (6)	C20—C15—C16—C22	−67.5 (6)
N4—C5—C6—C7	−45.4 (6)	C14—C15—C16—C22	161.6 (5)
N1—C2—C7—C8	−1.8 (6)	C5—N4—C17—C16	−168.9 (6)
C3—C2—C7—C8	−178.8 (5)	C3—N4—C17—C16	−6.4 (9)
N1—C2—C7—C6	178.0 (4)	C22—C16—C17—N4	−178.4 (6)
C3—C2—C7—C6	1.0 (8)	C15—C16—C17—N4	−0.5 (9)
C5—C6—C7—C2	15.3 (7)	C18—C19—C20—C21	177.2 (5)
C5—C6—C7—C8	−164.9 (5)	C18—C19—C20—C15	0.6 (8)
C2—C7—C8—C9	−176.9 (6)	C16—C15—C20—C19	116.3 (5)
C6—C7—C8—C9	3.3 (10)	C14—C15—C20—C19	−115.9 (5)
C2—C7—C8—C13	1.3 (5)	C16—C15—C20—C21	−60.0 (6)
C6—C7—C8—C13	−178.5 (5)	C14—C15—C20—C21	67.7 (6)
C13—C8—C9—C10	0.7 (8)	C19—C20—C21—O1	179.2 (5)
C7—C8—C9—C10	178.8 (6)	C15—C20—C21—O1	−4.1 (8)
C8—C9—C10—C11	−0.5 (9)	C23—O2—C22—O3	−3.0 (10)
C9—C10—C11—C12	−0.8 (9)	C23—O2—C22—C16	177.4 (7)
C10—C11—C12—C13	1.9 (9)	C17—C16—C22—O3	173.6 (6)
C2—N1—C13—C12	176.8 (5)	C15—C16—C22—O3	−4.4 (9)
C2—N1—C13—C8	−0.8 (5)	C17—C16—C22—O2	−6.9 (9)
C11—C12—C13—N1	−179.0 (6)	C15—C16—C22—O2	175.1 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.97 (5)	1.94 (6)	2.877 (5)	163 (5)
C3—H3···O1	1.11 (5)	2.21 (5)	3.049 (6)	131 (3)

Symmetry code: (i) x−1/2, −y+1/2, −z.

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