#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:30:38 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178785 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/39/4103942.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4103942
loop_
_publ_author_name
'José Barluenga'
'Eva Tudela'
'Alfredo Ballesteros'
'Miguel Tomás'
_publ_section_title
;
 Asymmetric C2-C3 Cyclopentannulation of the Indole Ring
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2096
_journal_page_last               2097
_journal_paper_doi               10.1021/ja809919t
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H24 I N O'
_chemical_formula_sum            'C14 H24 I N O'
_chemical_formula_weight         349.24
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.28670(10)
_cell_length_b                   10.3536(2)
_cell_length_c                   19.1306(3)
_cell_measurement_reflns_used    7360
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.5406
_cell_measurement_theta_min      4.2649
_cell_volume                     1443.28(4)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_molecular_graphics    'PLATON (Spek, 2006)'
_computing_publication_material  'SHELXL-97(Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-92 (Altomare, 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.2640
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type
;
 Oxford Diffraction Xcalibur Nova
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Nova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6255
_diffrn_reflns_theta_full        70.00
_diffrn_reflns_theta_max         73.86
_diffrn_reflns_theta_min         4.62
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    17.308
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.851
_refine_diff_density_min         -1.482
_refine_diff_density_rms         0.194
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.010(12)
_refine_ls_extinction_coef       0.0028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2773
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0768P)²+3.8182P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1130
_reflns_number_gt                2753
_reflns_number_total             2773
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja809919t_si_003.cif
_cod_data_source_block           (-)-8
_cod_database_code               4103942
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I1 I 1.32600(5) 0.78470(3) 0.684265(18) 0.02082(17) Uani 1 1 d .
O1 O 0.6080(6) 0.8858(4) 0.9413(2) 0.0238(9) Uani 1 1 d .
C4 C 1.0483(8) 0.9946(6) 0.9041(3) 0.0174(11) Uani 1 1 d .
H4 H 1.0018 1.0414 0.8632 0.021 Uiso 1 1 calc R
C2 C 0.7599(8) 0.9068(6) 0.9167(3) 0.0162(11) Uani 1 1 d .
C1 C 0.8478(8) 0.8384(5) 0.8530(3) 0.0161(11) Uani 1 1 d .
N1 N 0.8089(7) 0.6931(4) 0.8450(2) 0.0153(9) Uani 1 1 d .
C6 C 1.1617(9) 0.7727(6) 0.9081(3) 0.0242(12) Uani 1 1 d .
H6B H 1.2922 0.7882 0.9024 0.029 Uiso 1 1 calc R
H6A H 1.1315 0.7866 0.9569 0.029 Uiso 1 1 calc R
C5 C 1.0553(8) 0.8695(6) 0.8633(3) 0.0170(11) Uani 1 1 d .
H5 H 1.1159 0.8824 0.8181 0.020 Uiso 1 1 calc R
C7 C 1.1204(9) 0.6332(6) 0.8892(3) 0.0245(13) Uani 1 1 d .
H7A H 1.1581 0.6158 0.8415 0.029 Uiso 1 1 calc R
H7B H 1.1869 0.5753 0.9200 0.029 Uiso 1 1 calc R
C8 C 0.9163(9) 0.6121(6) 0.8968(3) 0.0208(12) Uani 1 1 d .
H8B H 0.8790 0.6345 0.9440 0.025 Uiso 1 1 calc R
H8A H 0.8884 0.5215 0.8894 0.025 Uiso 1 1 calc R
C12 C 1.2108(8) 1.0767(6) 0.9069(3) 0.0209(12) Uani 1 1 d .
H12 H 1.3170 1.0466 0.8801 0.025 Uiso 1 1 calc R
C11 C 0.7746(9) 0.9100(6) 0.7889(3) 0.0229(13) Uani 1 1 d .
H11B H 0.8246 0.8719 0.7473 0.034 Uiso 1 1 calc R
H11C H 0.8101 0.9992 0.7913 0.034 Uiso 1 1 calc R
H11A H 0.6432 0.9039 0.7878 0.034 Uiso 1 1 calc R
C3 C 0.8863(8) 1.0091(6) 0.9376(3) 0.0204(12) Uani 1 1 d .
H3A H 0.8338 1.0927 0.9263 0.025 Uiso 1 1 calc R
H3B H 0.9058 1.0057 0.9877 0.025 Uiso 1 1 calc R
C10 C 0.8557(8) 0.6474(6) 0.7721(3) 0.0198(12) Uani 1 1 d .
H10A H 0.7888 0.6977 0.7385 0.030 Uiso 1 1 calc R
H10B H 0.8230 0.5580 0.7673 0.030 Uiso 1 1 calc R
H10C H 0.9850 0.6575 0.7641 0.030 Uiso 1 1 calc R
C14 C 1.2545(11) 1.1527(8) 0.9735(3) 0.0315(15) Uani 1 1 d .
H14A H 1.1716 1.1433 1.0128 0.038 Uiso 1 1 calc R
H14B H 1.3826 1.1635 0.9860 0.038 Uiso 1 1 calc R
C9 C 0.6088(8) 0.6587(6) 0.8559(3) 0.0210(12) Uani 1 1 d .
H9B H 0.5711 0.6855 0.9017 0.031 Uiso 1 1 calc R
H9C H 0.5934 0.5669 0.8515 0.031 Uiso 1 1 calc R
H9A H 0.5352 0.7017 0.8214 0.031 Uiso 1 1 calc R
C13 C 1.1862(9) 1.2229(6) 0.9111(3) 0.0269(13) Uani 1 1 d .
H13B H 1.2728 1.2765 0.8858 0.032 Uiso 1 1 calc R
H13A H 1.0619 1.2562 0.9126 0.032 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 C4 C12 128.8(6)
C3 C4 C5 111.7(5)
C12 C4 C5 119.4(5)
C3 C4 H4 91.3
C12 C4 H4 91.3
C5 C4 H4 91.3
O1 C2 C3 126.4(5)
O1 C2 C1 126.6(5)
C3 C2 C1 106.7(5)
C11 C1 N1 109.3(5)
C11 C1 C2 105.4(5)
N1 C1 C2 116.7(5)
C11 C1 C5 109.9(5)
N1 C1 C5 113.1(5)
C2 C1 C5 102.0(4)
C10 N1 C9 105.7(4)
C10 N1 C8 108.3(4)
C9 N1 C8 106.0(4)
C10 N1 C1 110.9(4)
C9 N1 C1 113.2(5)
C8 N1 C1 112.4(4)
C7 C6 C5 112.9(5)
C7 C6 H6B 109.0
C5 C6 H6B 109.0
C7 C6 H6A 109.0
C5 C6 H6A 109.0
H6B C6 H6A 107.8
C4 C5 C6 106.9(5)
C4 C5 C1 102.1(4)
C6 C5 C1 115.3(5)
C4 C5 H5 110.7
C6 C5 H5 110.7
C1 C5 H5 110.7
C8 C7 C6 108.0(5)
C8 C7 H7A 110.1
C6 C7 H7A 110.1
C8 C7 H7B 110.1
C6 C7 H7B 110.1
H7A C7 H7B 108.4
C7 C8 N1 111.4(5)
C7 C8 H8B 109.4
N1 C8 H8B 109.4
C7 C8 H8A 109.4
N1 C8 H8A 109.4
H8B C8 H8A 108.0
C4 C12 C13 119.0(5)
C4 C12 C14 120.0(5)
C13 C12 C14 58.0(5)
C4 C12 H12 115.9
C13 C12 H12 115.9
C14 C12 H12 115.9
C1 C11 H11B 109.5
C1 C11 H11C 109.5
H11B C11 H11C 109.5
C1 C11 H11A 109.5
H11B C11 H11A 109.5
H11C C11 H11A 109.5
C4 C3 C2 109.8(5)
C4 C3 H3A 109.7
C2 C3 H3A 109.7
C4 C3 H3B 109.7
C2 C3 H3B 109.7
H3A C3 H3B 108.2
N1 C10 H10A 109.5
N1 C10 H10B 109.5
H10A C10 H10B 109.5
N1 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C13 C14 C12 60.9(4)
C13 C14 H14A 117.7
C12 C14 H14A 117.7
C13 C14 H14B 117.7
C12 C14 H14B 117.7
H14A C14 H14B 114.8
N1 C9 H9B 109.5
N1 C9 H9C 109.5
H9B C9 H9C 109.5
N1 C9 H9A 109.5
H9B C9 H9A 109.5
H9C C9 H9A 109.5
C14 C13 C12 61.1(4)
C14 C13 H13B 117.7
C12 C13 H13B 117.7
C14 C13 H13A 117.7
C12 C13 H13A 117.7
H13B C13 H13A 114.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.223(7)
C4 C3 1.352(8)
C4 C12 1.459(8)
C4 C5 1.513(8)
C4 H4 0.9800
C2 C3 1.460(8)
C2 C1 1.547(7)
C1 C11 1.528(8)
C1 N1 1.539(7)
C1 C5 1.559(8)
N1 C10 1.512(7)
N1 C9 1.515(8)
N1 C8 1.516(7)
C6 C7 1.519(9)
C6 C5 1.530(8)
C6 H6B 0.9700
C6 H6A 0.9700
C5 H5 0.9800
C7 C8 1.511(9)
C7 H7A 0.9700
C7 H7B 0.9700
C8 H8B 0.9700
C8 H8A 0.9700
C12 C13 1.526(9)
C12 C14 1.530(8)
C12 H12 0.9800
C11 H11B 0.9600
C11 H11C 0.9600
C11 H11A 0.9600
C3 H3A 0.9700
C3 H3B 0.9700
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C14 C13 1.483(10)
C14 H14A 0.9700
C14 H14B 0.9700
C9 H9B 0.9600
C9 H9C 0.9600
C9 H9A 0.9600
C13 H13B 0.9700
C13 H13A 0.9700
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 C2 C1 C11 84.2(7)
C3 C2 C1 C11 -90.8(5)
O1 C2 C1 N1 -37.3(8)
C3 C2 C1 N1 147.8(5)
O1 C2 C1 C5 -161.1(6)
C3 C2 C1 C5 24.0(6)
C11 C1 N1 C10 44.7(7)
C2 C1 N1 C10 164.1(5)
C5 C1 N1 C10 -78.1(6)
C11 C1 N1 C9 -73.9(6)
C2 C1 N1 C9 45.5(6)
C5 C1 N1 C9 163.3(5)
C11 C1 N1 C8 166.0(5)
C2 C1 N1 C8 -74.6(6)
C5 C1 N1 C8 43.3(6)
C3 C4 C5 C6 -99.2(6)
C12 C4 C5 C6 76.6(6)
C3 C4 C5 C1 22.2(6)
C12 C4 C5 C1 -162.0(5)
C7 C6 C5 C4 158.0(5)
C7 C6 C5 C1 45.3(7)
C11 C1 C5 C4 84.7(5)
N1 C1 C5 C4 -152.9(4)
C2 C1 C5 C4 -26.7(5)
C11 C1 C5 C6 -159.8(5)
N1 C1 C5 C6 -37.4(6)
C2 C1 C5 C6 88.7(5)
C5 C6 C7 C8 -57.5(7)
C6 C7 C8 N1 64.5(6)
C10 N1 C8 C7 64.5(6)
C9 N1 C8 C7 177.5(5)
C1 N1 C8 C7 -58.4(7)
C3 C4 C12 C13 -37.5(9)
C5 C4 C12 C13 147.5(6)
C3 C4 C12 C14 30.2(10)
C5 C4 C12 C14 -144.8(6)
C12 C4 C3 C2 177.5(6)
C5 C4 C3 C2 -7.2(7)
O1 C2 C3 C4 173.7(6)
C1 C2 C3 C4 -11.4(7)
C4 C12 C14 C13 -107.4(7)
C4 C12 C13 C14 109.1(6)
