#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:50:43 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178408 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/29/4022929.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_4022929
loop_
_publ_author_name
'Karl B. Lindsay'
'Francesc Ferrando'
'Kasper L. Christensen'
'Jacob Overgaard'
'Tomàs Roca'
'M.-Lluïsa Bennasar'
'Troels Skrydstrup'
_publ_contact_author             'Overgaard, Jacob'
_publ_contact_author_email       jacobo@chem.au.dk
_publ_section_title
;
 SmI₂-Promoted Radical Addition Reactions with
 N-(2-Indolylacyl)oxazolidinones: Synthesis of Bisindole Compounds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4181
_journal_page_last               4188
_journal_paper_doi               10.1021/jo070273d
_journal_volume                  72
_journal_year                    2007
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C32 H22 N2 O2'
_chemical_formula_sum            'C32 H22 N2 O2'
_chemical_formula_weight         466.52
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2006-09-11T11:07:21-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 102.619(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.702(4)
_cell_length_b                   15.520(5)
_cell_length_c                   6.3747(18)
_cell_measurement_reflns_used    2571
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.37
_cell_measurement_theta_min      2.62
_cell_measurement_wavelength     0.71073
_cell_volume                     1129.8(6)
_computing_cell_refinement       'Saint+ (Bruker-Nonius, 2006)'
_computing_data_collection       'Apex2 (Bruker-Nonius, 2006)'
_computing_data_reduction        'Saint+ (Bruker-Nonius, 2006)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker X8 APEX-II diffractometer'
_diffrn_measurement_method       'φ-scans and ω-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1016
_diffrn_reflns_av_unetI/netI     0.0892
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            22161
_diffrn_reflns_theta_full        29.5
_diffrn_reflns_theta_max         30.61
_diffrn_reflns_theta_min         3.53
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.07
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3356
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1225
_refine_ls_R_factor_gt           0.0635
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0723P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1528
_reflns_number_gt                2016
_reflns_number_total             3356
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070273dsi20070208_060052.cif
_cod_data_source_block           test
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4022929
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 0.40438(16) 0.57269(11) 0.3330(3) 0.0179(4) Uani 1 1 d .
C2 C 0.46015(16) 0.54487(11) 0.1653(3) 0.0184(4) Uani 1 1 d .
C3 C 0.15772(17) 0.35944(11) 0.1214(3) 0.0190(4) Uani 1 1 d .
C4 C 0.40635(17) 0.64850(12) 0.4552(3) 0.0203(4) Uani 1 1 d .
H4 H 0.4553 0.6955 0.4374 0.024 Uiso 1 1 calc R
C5 C 0.33318(15) 0.50315(11) 0.3697(3) 0.0179(4) Uani 1 1 d .
C6 C 0.54237(16) 0.59010(11) 0.0622(3) 0.0181(4) Uani 1 1 d .
C7 C 0.42247(15) 0.46094(11) 0.1110(3) 0.0172(4) Uani 1 1 d .
C8 C 0.26338(17) 0.58308(12) 0.6338(3) 0.0239(4) Uani 1 1 d .
H8 H 0.2153 0.5884 0.7353 0.029 Uiso 1 1 calc R
C9 C -0.04534(18) 0.31784(12) 0.0839(3) 0.0260(5) Uani 1 1 d .
H9 H -0.1034 0.2864 0.135 0.031 Uiso 1 1 calc R
C10 C 0.33506(18) 0.65266(12) 0.6022(3) 0.0238(4) Uani 1 1 d .
H10 H 0.3345 0.7038 0.6838 0.029 Uiso 1 1 calc R
C11 C 0.26175(16) 0.50731(12) 0.5200(3) 0.0213(4) Uani 1 1 d .
H11 H 0.2143 0.46 0.5423 0.026 Uiso 1 1 calc R
C12 C -0.07646(18) 0.36715(12) -0.0998(3) 0.0256(5) Uani 1 1 d .
H12 H -0.1559 0.3698 -0.1756 0.031 Uiso 1 1 calc R
C13 C 0.00894(18) 0.41293(13) -0.1730(3) 0.0287(5) Uani 1 1 d .
H13 H -0.0124 0.4474 -0.2987 0.034 Uiso 1 1 calc R
C14 C 0.28517(16) 0.35244(11) 0.2362(3) 0.0200(4) Uani 1 1 d .
H14A H 0.29 0.3337 0.3863 0.024 Uiso 1 1 calc R
H14B H 0.3241 0.3082 0.1643 0.024 Uiso 1 1 calc R
C15 C 0.07147(17) 0.31408(12) 0.1950(3) 0.0228(4) Uani 1 1 d .
H15 H 0.0923 0.2803 0.3218 0.027 Uiso 1 1 calc R
C16 C 0.12514(17) 0.40878(12) -0.0643(3) 0.0238(4) Uani 1 1 d .
H16 H 0.183 0.4399 -0.117 0.029 Uiso 1 1 calc R
N1 N 0.34698(13) 0.43532(9) 0.2366(2) 0.0177(3) Uani 1 1 d .
O1 O 0.58034(12) 0.66300(8) 0.1156(2) 0.0249(3) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
_geom_angle_site_symmetry_3
C4 C1 C5 119.01(18) .
C4 C1 C2 135.09(17) .
C5 C1 C2 105.90(15) .
C7 C2 C1 107.17(16) .
C7 C2 C6 122.81(17) .
C1 C2 C6 130.02(16) .
C16 C3 C15 118.72(18) .
C16 C3 C14 120.56(17) .
C15 C3 C14 120.69(17) .
C10 C4 C1 118.26(18) .
C10 C4 H4 120.9 .
C1 C4 H4 120.9 .
N1 C5 C11 128.33(17) .
N1 C5 C1 109.10(16) .
C11 C5 C1 122.57(17) .
O1 C6 C2 123.32(17) .
O1 C6 C7 123.41(17) 3_665
C2 C6 C7 113.26(15) 3_665
N1 C7 C2 109.54(16) .
N1 C7 C6 126.54(16) 3_665
C2 C7 C6 123.89(16) 3_665
C11 C8 C10 121.24(19) .
C11 C8 H8 119.4 .
C10 C8 H8 119.4 .
C12 C9 C15 120.07(19) .
C12 C9 H9 120 .
C15 C9 H9 120 .
C4 C10 C8 121.76(18) .
C4 C10 H10 119.1 .
C8 C10 H10 119.1 .
C8 C11 C5 117.13(18) .
C8 C11 H11 121.4 .
C5 C11 H11 121.4 .
C9 C12 C13 119.58(19) .
C9 C12 H12 120.2 .
C13 C12 H12 120.2 .
C16 C13 C12 120.53(19) .
C16 C13 H13 119.7 .
C12 C13 H13 119.7 .
N1 C14 C3 111.64(14) .
N1 C14 H14A 109.3 .
C3 C14 H14A 109.3 .
N1 C14 H14B 109.3 .
C3 C14 H14B 109.3 .
H14A C14 H14B 108 .
C3 C15 C9 120.61(18) .
C3 C15 H15 119.7 .
C9 C15 H15 119.7 .
C13 C16 C3 120.49(19) .
C13 C16 H16 119.8 .
C3 C16 H16 119.8 .
C7 N1 C5 108.25(14) .
C7 N1 C14 128.95(15) .
C5 N1 C14 122.78(15) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C4 1.408(3) .
C1 C5 1.414(2) .
C1 C2 1.435(3) .
C2 C7 1.394(2) .
C2 C6 1.458(3) .
C3 C16 1.391(3) .
C3 C15 1.393(3) .
C3 C14 1.515(3) .
C4 C10 1.385(3) .
C4 H4 0.95 .
C5 N1 1.384(2) .
C5 C11 1.403(3) .
C6 O1 1.236(2) .
C6 C7 1.488(3) 3_665
C7 N1 1.374(2) .
C7 C6 1.488(3) 3_665
C8 C11 1.380(3) .
C8 C10 1.408(3) .
C8 H8 0.95 .
C9 C12 1.380(3) .
C9 C15 1.397(3) .
C9 H9 0.95 .
C10 H10 0.95 .
C11 H11 0.95 .
C12 C13 1.388(3) .
C12 H12 0.95 .
C13 C16 1.386(3) .
C13 H13 0.95 .
C14 N1 1.475(2) .
C14 H14A 0.99 .
C14 H14B 0.99 .
C15 H15 0.95 .
C16 H16 0.95 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C4 C1 C2 C7 179.4(2) . .
C5 C1 C2 C7 -0.9(2) . .
C4 C1 C2 C6 0.0(3) . .
C5 C1 C2 C6 179.74(18) . .
C5 C1 C4 C10 -2.1(3) . .
C2 C1 C4 C10 177.61(19) . .
C4 C1 C5 N1 -178.57(16) . .
C2 C1 C5 N1 1.67(19) . .
C4 C1 C5 C11 1.6(3) . .
C2 C1 C5 C11 -178.12(16) . .
C7 C2 C6 O1 -176.67(17) . .
C1 C2 C6 O1 2.7(3) . .
C7 C2 C6 C7 2.3(3) . 3_665
C1 C2 C6 C7 -178.37(17) . 3_665
C1 C2 C7 N1 -0.3(2) . .
C6 C2 C7 N1 179.20(16) . .
C1 C2 C7 C6 177.99(16) . 3_665
C6 C2 C7 C6 -2.6(3) . 3_665
C1 C4 C10 C8 1.1(3) . .
C11 C8 C10 C4 0.4(3) . .
C10 C8 C11 C5 -0.9(3) . .
N1 C5 C11 C8 -179.89(17) . .
C1 C5 C11 C8 -0.1(3) . .
C15 C9 C12 C13 -0.1(3) . .
C9 C12 C13 C16 0.6(3) . .
C16 C3 C14 N1 38.9(2) . .
C15 C3 C14 N1 -143.51(17) . .
C16 C3 C15 C9 0.2(3) . .
C14 C3 C15 C9 -177.37(17) . .
C12 C9 C15 C3 -0.4(3) . .
C12 C13 C16 C3 -0.8(3) . .
C15 C3 C16 C13 0.3(3) . .
C14 C3 C16 C13 177.93(18) . .
C2 C7 N1 C5 1.3(2) . .
C6 C7 N1 C5 -176.88(16) 3_665 .
C2 C7 N1 C14 179.76(16) . .
C6 C7 N1 C14 1.6(3) 3_665 .
C11 C5 N1 C7 177.91(18) . .
C1 C5 N1 C7 -1.87(19) . .
C11 C5 N1 C14 -0.7(3) . .
C1 C5 N1 C14 179.57(15) . .
C3 C14 N1 C7 -102.5(2) . .
C3 C14 N1 C5 75.7(2) . .
