#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/60/4026003.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_4026003
loop_
_publ_author_name
'Ying-Xiu Li'
'Ke-Gong Ji'
'Hai-Xi Wang'
'Shaukat Ali'
'Yong-Min Liang'
_publ_section_title
;
 Iodine-Induced Regioselective C-C and C-N Bonds Formation of N-Protected
 Indoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              744
_journal_page_last               747
_journal_paper_doi               10.1021/jo1023014
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C13 H18 N2 O'
_chemical_formula_weight         218.29
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.73(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.30(2)
_cell_length_b                   17.24(4)
_cell_length_c                   8.57(2)
_cell_measurement_reflns_used    1592
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.63
_cell_measurement_theta_min      2.36
_cell_volume                     1222(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6414
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9783
_exptl_absorpt_correction_T_min  0.9739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.015(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   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0751P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1442
_reflns_number_gt                1478
_reflns_number_total             2259
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1023014_si_004.cif
_cod_data_source_block           p21c
_cod_database_code               4026003
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 -0.0584(2) 0.61956(9) 0.7834(2) 0.0432(5) Uani 1 1 d .
C2 C -0.0871(2) 0.60221(11) 0.9380(2) 0.0556(6) Uani 1 1 d .
H2 H -0.0091 0.5780 1.0052 0.067 Uiso 1 1 calc R
C3 C -0.2370(3) 0.62260(12) 0.9873(3) 0.0628(6) Uani 1 1 d .
H3 H -0.2591 0.6122 1.0898 0.075 Uiso 1 1 calc R
C4 C -0.3551(3) 0.65842(12) 0.8860(3) 0.0641(6) Uani 1 1 d .
H4 H -0.4549 0.6704 0.9218 0.077 Uiso 1 1 calc R
C5 C -0.3261(2) 0.67646(12) 0.7331(3) 0.0627(6) Uani 1 1 d .
H5 H -0.4052 0.7007 0.6671 0.075 Uiso 1 1 calc R
C6 C -0.1745(2) 0.65748(10) 0.6789(2) 0.0480(5) Uani 1 1 d .
C7 C -0.1032(2) 0.66737(11) 0.5335(2) 0.0531(5) Uani 1 1 d .
H7 H -0.1515 0.6905 0.4434 0.064 Uiso 1 1 calc R
C8 C 0.0501(2) 0.63634(10) 0.5518(2) 0.0432(5) Uani 1 1 d .
C9 C 0.1584(3) 0.69168(11) 0.3226(2) 0.0588(6) Uani 1 1 d .
H9A H 0.1429 0.7430 0.3654 0.071 Uiso 1 1 calc R
H9B H 0.0647 0.6792 0.2519 0.071 Uiso 1 1 calc R
C10 C 0.3092(3) 0.69060(13) 0.2348(3) 0.0725(7) Uani 1 1 d .
H10A H 0.2985 0.7286 0.1512 0.087 Uiso 1 1 calc R
H10B H 0.4016 0.7050 0.3056 0.087 Uiso 1 1 calc R
C11 C 0.3529(3) 0.55876(13) 0.2917(3) 0.0726(7) Uani 1 1 d .
H11A H 0.4469 0.5710 0.3623 0.087 Uiso 1 1 calc R
H11B H 0.3700 0.5081 0.2467 0.087 Uiso 1 1 calc R
C12 C 0.2047(3) 0.55601(11) 0.3833(2) 0.0580(6) Uani 1 1 d .
H12A H 0.1113 0.5406 0.3149 0.070 Uiso 1 1 calc R
H12B H 0.2204 0.5181 0.4668 0.070 Uiso 1 1 calc R
C13 C 0.2325(2) 0.57456(14) 0.7734(2) 0.0683(6) Uani 1 1 d .
H13A H 0.2464 0.5879 0.8824 0.102 Uiso 1 1 calc R
H13B H 0.3207 0.5953 0.7207 0.102 Uiso 1 1 calc R
H13C H 0.2303 0.5191 0.7624 0.102 Uiso 1 1 calc R
N1 N 0.08022(17) 0.60713(8) 0.70422(17) 0.0438(4) Uani 1 1 d .
N2 N 0.17633(18) 0.63395(8) 0.45071(17) 0.0452(4) Uani 1 1 d .
O1 O 0.33693(19) 0.61532(10) 0.16946(18) 0.0783(5) 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 0.0000 0.0000 '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 0.0060 '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
C2 C1 N1 129.63(19)
C2 C1 C6 122.4(2)
N1 C1 C6 107.9(2)
C3 C2 C1 117.4(2)
C3 C2 H2 121.3
C1 C2 H2 121.3
C2 C3 C4 121.4(2)
C2 C3 H3 119.3
C4 C3 H3 119.3
C5 C4 C3 121.2(2)
C5 C4 H4 119.4
C3 C4 H4 119.4
C4 C5 C6 119.1(2)
C4 C5 H5 120.4
C6 C5 H5 120.4
C5 C6 C1 118.4(2)
C5 C6 C7 134.43(19)
C1 C6 C7 107.2(2)
C8 C7 C6 107.38(19)
C8 C7 H7 126.3
C6 C7 H7 126.3
C7 C8 N1 109.73(16)
C7 C8 N2 131.7(2)
N1 C8 N2 118.4(2)
N2 C9 C10 108.91(19)
N2 C9 H9A 109.9
C10 C9 H9A 109.9
N2 C9 H9B 109.9
C10 C9 H9B 109.9
H9A C9 H9B 108.3
O1 C10 C9 111.73(18)
O1 C10 H10A 109.3
C9 C10 H10A 109.3
O1 C10 H10B 109.3
C9 C10 H10B 109.3
H10A C10 H10B 107.9
O1 C11 C12 111.8(2)
O1 C11 H11A 109.3
C12 C11 H11A 109.3
O1 C11 H11B 109.3
C12 C11 H11B 109.3
H11A C11 H11B 107.9
N2 C12 C11 109.53(17)
N2 C12 H12A 109.8
C11 C12 H12A 109.8
N2 C12 H12B 109.8
C11 C12 H12B 109.8
H12A C12 H12B 108.2
N1 C13 H13A 109.5
N1 C13 H13B 109.5
H13A C13 H13B 109.5
N1 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C1 N1 C8 107.80(19)
C1 N1 C13 125.4(2)
C8 N1 C13 126.64(16)
C8 N2 C9 113.63(18)
C8 N2 C12 114.38(15)
C9 N2 C12 109.2(2)
C11 O1 C10 109.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.398(4)
C1 N1 1.400(3)
C1 C6 1.420(3)
C2 C3 1.392(4)
C2 H2 0.9300
C3 C4 1.398(4)
C3 H3 0.9300
C4 C5 1.387(4)
C4 H4 0.9300
C5 C6 1.415(4)
C5 H5 0.9300
C6 C7 1.433(4)
C7 C8 1.377(4)
C7 H7 0.9300
C8 N1 1.403(4)
C8 N2 1.414(3)
C9 N2 1.481(4)
C9 C10 1.512(4)
C9 H9A 0.9700
C9 H9B 0.9700
C10 O1 1.439(4)
C10 H10A 0.9700
C10 H10B 0.9700
C11 O1 1.430(4)
C11 C12 1.514(4)
C11 H11A 0.9700
C11 H11B 0.9700
C12 N2 1.489(4)
C12 H12A 0.9700
C12 H12B 0.9700
C13 N1 1.463(4)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
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
N1 C1 C2 C3 178.76(17)
C6 C1 C2 C3 0.9(3)
C1 C2 C3 C4 0.6(3)
C2 C3 C4 C5 -1.3(3)
C3 C4 C5 C6 0.6(3)
C4 C5 C6 C1 0.8(3)
C4 C5 C6 C7 -179.5(2)
C2 C1 C6 C5 -1.6(3)
N1 C1 C6 C5 -179.88(16)
C2 C1 C6 C7 178.63(16)
N1 C1 C6 C7 0.4(2)
C5 C6 C7 C8 -179.8(2)
C1 C6 C7 C8 -0.1(2)
C6 C7 C8 N1 -0.3(2)
C6 C7 C8 N2 -176.00(18)
N2 C9 C10 O1 59.5(3)
O1 C11 C12 N2 -58.0(3)
C2 C1 N1 C8 -178.63(17)
C6 C1 N1 C8 -0.53(19)
C2 C1 N1 C13 -2.7(3)
C6 C1 N1 C13 175.41(17)
C7 C8 N1 C1 0.50(19)
N2 C8 N1 C1 176.89(14)
C7 C8 N1 C13 -175.38(18)
N2 C8 N1 C13 1.0(3)
C7 C8 N2 C9 18.7(3)
N1 C8 N2 C9 -156.77(16)
C7 C8 N2 C12 -107.6(2)
N1 C8 N2 C12 76.9(2)
C10 C9 N2 C8 173.07(16)
C10 C9 N2 C12 -57.9(2)
C11 C12 N2 C8 -174.02(17)
C11 C12 N2 C9 57.4(2)
C12 C11 O1 C10 58.1(2)
C9 C10 O1 C11 -59.0(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659336
