#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/86/4028631.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_4028631
loop_
_publ_author_name
'Estela Álvarez'
'Patricia García-García'
'Manuel A. Fernández-Rodríguez'
'Roberto Sanz'
_publ_section_title
;
 Regioselective Synthesis of Elusive 4,9-Dihydro-1H-Carbazoles by
 Gold-Catalyzed Cycloisomerization of 3-Allenylmethylindoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9758
_journal_page_last               9771
_journal_paper_doi               10.1021/jo401388b
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C23 H19 N'
_chemical_formula_sum            'C23 H19 N'
_chemical_formula_weight         309.39
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 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                   17.627(4)
_cell_length_b                   16.321(4)
_cell_length_c                   5.5951(12)
_cell_measurement_reflns_used    4331
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.30
_cell_measurement_theta_min      2.31
_cell_volume                     1609.7(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega 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  0.0689
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            14921
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.70
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.7530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (SHELDRICK, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         1578
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0337
_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)+(0.0374P)²+0.4164P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0828
_reflns_number_gt                1498
_reflns_number_total             1578
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401388b_si_002.cif
_cod_data_source_block           datosm
_cod_original_sg_symbol_Hall     'P 2c -2n '
_cod_database_code               4028631
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, 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
N1 N 0.25491(10) -0.02436(10) 0.1116(4) 0.0265(4) Uani 1 1 d .
C1 C 0.28868(12) 0.05151(13) 0.1327(5) 0.0242(5) Uani 1 1 d .
C2 C 0.34375(13) 0.08817(14) -0.0109(5) 0.0308(6) Uani 1 1 d .
H2 H 0.3654 0.0600 -0.1429 0.037 Uiso 1 1 calc R
C3 C 0.36550(13) 0.16690(15) 0.0461(5) 0.0342(6) Uani 1 1 d .
H3 H 0.4024 0.1938 -0.0496 0.041 Uiso 1 1 calc R
C4 C 0.33428(13) 0.20794(15) 0.2420(5) 0.0331(6) Uani 1 1 d .
H4 H 0.3506 0.2621 0.2771 0.040 Uiso 1 1 calc R
C5 C 0.28021(12) 0.17147(13) 0.3855(5) 0.0290(5) Uani 1 1 d .
H5 H 0.2598 0.1999 0.5192 0.035 Uiso 1 1 calc R
C6 C 0.25592(12) 0.09190(13) 0.3308(4) 0.0230(5) Uani 1 1 d .
C7 C 0.20007(12) 0.03697(13) 0.4270(5) 0.0237(5) Uani 1 1 d .
C8 C 0.20074(12) -0.03149(13) 0.2888(4) 0.0242(5) Uani 1 1 d .
C9 C 0.14922(14) -0.10342(13) 0.3144(5) 0.0322(6) Uani 1 1 d .
H9A H 0.1791 -0.1526 0.3569 0.039 Uiso 1 1 calc R
H9B H 0.1232 -0.1141 0.1607 0.039 Uiso 1 1 calc R
C10 C 0.09163(14) -0.08668(14) 0.5054(5) 0.0341(6) Uani 1 1 d .
H10 H 0.0527 -0.1262 0.5281 0.041 Uiso 1 1 calc R
C11 C 0.09080(13) -0.02105(13) 0.6452(5) 0.0336(6) Uani 1 1 d .
H11 H 0.0512 -0.0172 0.7597 0.040 Uiso 1 1 calc R
C12 C 0.14793(12) 0.04829(13) 0.6373(5) 0.0267(5) Uani 1 1 d .
H12 H 0.1793 0.0453 0.7859 0.032 Uiso 1 1 calc R
C13 C 0.10963(11) 0.13184(12) 0.6317(5) 0.0238(5) Uani 1 1 d .
C14 C 0.12485(12) 0.18968(13) 0.8012(4) 0.0267(5) Uani 1 1 d .
H14 H 0.1565 0.1760 0.9328 0.032 Uiso 1 1 calc R
C15 C 0.09416(12) 0.27019(13) 0.7843(4) 0.0258(5) Uani 1 1 d .
C16 C 0.04459(12) 0.28902(13) 0.5930(5) 0.0244(5) Uani 1 1 d .
C17 C 0.02836(12) 0.22767(13) 0.4217(5) 0.0286(5) Uani 1 1 d .
H17 H -0.0052 0.2393 0.2932 0.034 Uiso 1 1 calc R
C18 C 0.06073(12) 0.15178(13) 0.4400(5) 0.0274(5) Uani 1 1 d .
H18 H 0.0502 0.1117 0.3216 0.033 Uiso 1 1 calc R
C19 C 0.11374(14) 0.33277(15) 0.9482(5) 0.0349(6) Uani 1 1 d .
H19 H 0.1463 0.3207 1.0788 0.042 Uiso 1 1 calc R
C20 C 0.08619(14) 0.41039(15) 0.9200(5) 0.0371(6) Uani 1 1 d .
H20 H 0.1010 0.4522 1.0284 0.045 Uiso 1 1 calc R
C21 C 0.03624(14) 0.42885(15) 0.7323(5) 0.0339(6) Uani 1 1 d .
H21 H 0.0168 0.4828 0.7160 0.041 Uiso 1 1 calc R
C22 C 0.01552(13) 0.36992(13) 0.5735(5) 0.0290(6) Uani 1 1 d .
H22 H -0.0188 0.3830 0.4481 0.035 Uiso 1 1 calc R
C23 C 0.27490(13) -0.08656(14) -0.0641(5) 0.0321(6) Uani 1 1 d .
H23A H 0.2632 -0.0663 -0.2248 0.048 Uiso 1 1 calc R
H23B H 0.2458 -0.1366 -0.0329 0.048 Uiso 1 1 calc R
H23C H 0.3292 -0.0986 -0.0528 0.048 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 0.0033 0.0000 '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 0.0000 '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
C1 N1 C8 108.20(19)
C1 N1 C23 125.4(2)
C8 N1 C23 126.37(18)
N1 C1 C2 129.5(2)
N1 C1 C6 108.0(2)
C2 C1 C6 122.4(2)
C3 C2 C1 117.4(2)
C3 C2 H2 121.3
C1 C2 H2 121.3
C2 C3 C4 121.3(2)
C2 C3 H3 119.4
C4 C3 H3 119.4
C5 C4 C3 121.4(2)
C5 C4 H4 119.3
C3 C4 H4 119.3
C4 C5 C6 118.9(2)
C4 C5 H5 120.6
C6 C5 H5 120.6
C5 C6 C1 118.6(2)
C5 C6 C7 134.9(2)
C1 C6 C7 106.43(19)
C8 C7 C6 107.1(2)
C8 C7 C12 123.45(19)
C6 C7 C12 129.4(2)
C7 C8 N1 110.19(18)
C7 C8 C9 126.0(2)
N1 C8 C9 123.8(2)
C8 C9 C10 109.72(19)
C8 C9 H9A 109.7
C10 C9 H9A 109.7
C8 C9 H9B 109.7
C10 C9 H9B 109.7
H9A C9 H9B 108.2
C11 C10 C9 125.1(2)
C11 C10 H10 117.4
C9 C10 H10 117.4
C10 C11 C12 125.3(2)
C10 C11 H11 117.3
C12 C11 H11 117.3
C7 C12 C11 109.7(2)
C7 C12 C13 111.43(19)
C11 C12 C13 112.01(18)
C7 C12 H12 107.8
C11 C12 H12 107.8
C13 C12 H12 107.8
C14 C13 C18 119.19(19)
C14 C13 C12 121.2(2)
C18 C13 C12 119.5(2)
C13 C14 C15 121.1(2)
C13 C14 H14 119.4
C15 C14 H14 119.4
C19 C15 C16 118.9(2)
C19 C15 C14 122.0(2)
C16 C15 C14 119.0(2)
C17 C16 C15 118.9(2)
C17 C16 C22 122.2(2)
C15 C16 C22 118.9(2)
C18 C17 C16 120.4(2)
C18 C17 H17 119.8
C16 C17 H17 119.8
C17 C18 C13 121.3(2)
C17 C18 H18 119.3
C13 C18 H18 119.3
C20 C19 C15 120.5(2)
C20 C19 H19 119.7
C15 C19 H19 119.7
C19 C20 C21 120.6(2)
C19 C20 H20 119.7
C21 C20 H20 119.7
C22 C21 C20 120.4(2)
C22 C21 H21 119.8
C20 C21 H21 119.8
C21 C22 C16 120.7(2)
C21 C22 H22 119.7
C16 C22 H22 119.7
N1 C23 H23A 109.5
N1 C23 H23B 109.5
H23A C23 H23B 109.5
N1 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.379(3)
N1 C8 1.382(3)
N1 C23 1.456(3)
C1 C2 1.395(3)
C1 C6 1.413(3)
C2 C3 1.378(3)
C2 H2 0.9500
C3 C4 1.397(4)
C3 H3 0.9500
C4 C5 1.381(3)
C4 H4 0.9500
C5 C6 1.401(3)
C5 H5 0.9500
C6 C7 1.436(3)
C7 C8 1.359(3)
C7 C12 1.504(3)
C8 C9 1.491(3)
C9 C10 1.499(4)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.326(4)
C10 H10 0.9500
C11 C12 1.516(3)
C11 H11 0.9500
C12 C13 1.522(3)
C12 H12 1.0000
C13 C14 1.365(3)
C13 C18 1.414(3)
C14 C15 1.424(3)
C14 H14 0.9500
C15 C19 1.415(3)
C15 C16 1.416(3)
C16 C17 1.415(3)
C16 C22 1.420(3)
C17 C18 1.368(3)
C17 H17 0.9500
C18 H18 0.9500
C19 C20 1.366(3)
C19 H19 0.9500
C20 C21 1.403(4)
C20 H20 0.9500
C21 C22 1.359(4)
C21 H21 0.9500
C22 H22 0.9500
C23 H23A 0.9800
C23 H23B 0.9800
C23 H23C 0.9800
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
C8 N1 C1 C2 -176.8(2)
C23 N1 C1 C2 4.8(4)
C8 N1 C1 C6 1.2(2)
C23 N1 C1 C6 -177.2(2)
N1 C1 C2 C3 177.4(2)
C6 C1 C2 C3 -0.4(3)
C1 C2 C3 C4 0.8(4)
C2 C3 C4 C5 -0.3(4)
C3 C4 C5 C6 -0.7(4)
C4 C5 C6 C1 1.0(3)
C4 C5 C6 C7 -176.4(3)
N1 C1 C6 C5 -178.7(2)
C2 C1 C6 C5 -0.5(3)
N1 C1 C6 C7 -0.6(2)
C2 C1 C6 C7 177.6(2)
C5 C6 C7 C8 177.4(3)
C1 C6 C7 C8 -0.3(2)
C5 C6 C7 C12 -2.0(4)
C1 C6 C7 C12 -179.7(2)
C6 C7 C8 N1 1.1(2)
C12 C7 C8 N1 -179.4(2)
C6 C7 C8 C9 -176.7(2)
C12 C7 C8 C9 2.8(4)
C1 N1 C8 C7 -1.5(2)
C23 N1 C8 C7 177.0(2)
C1 N1 C8 C9 176.4(2)
C23 N1 C8 C9 -5.2(3)
C7 C8 C9 C10 4.4(3)
N1 C8 C9 C10 -173.1(2)
C8 C9 C10 C11 -5.6(4)
C9 C10 C11 C12 -0.2(4)
C8 C7 C12 C11 -8.2(3)
C6 C7 C12 C11 171.1(2)
C8 C7 C12 C13 -132.8(2)
C6 C7 C12 C13 46.5(3)
C10 C11 C12 C7 7.1(3)
C10 C11 C12 C13 131.4(3)
C7 C12 C13 C14 -113.6(2)
C11 C12 C13 C14 123.0(3)
C7 C12 C13 C18 62.7(3)
C11 C12 C13 C18 -60.7(3)
C18 C13 C14 C15 -1.9(3)
C12 C13 C14 C15 174.4(2)
C13 C14 C15 C19 -175.2(2)
C13 C14 C15 C16 2.6(3)
C19 C15 C16 C17 176.5(2)
C14 C15 C16 C17 -1.3(3)
C19 C15 C16 C22 -0.7(3)
C14 C15 C16 C22 -178.5(2)
C15 C16 C17 C18 -0.6(3)
C22 C16 C17 C18 176.5(2)
C16 C17 C18 C13 1.4(4)
C14 C13 C18 C17 -0.2(3)
C12 C13 C18 C17 -176.5(2)
C16 C15 C19 C20 -1.0(3)
C14 C15 C19 C20 176.8(2)
C15 C19 C20 C21 1.9(4)
C19 C20 C21 C22 -1.0(4)
C20 C21 C22 C16 -0.7(4)
C17 C16 C22 C21 -175.6(2)
C15 C16 C22 C21 1.5(3)
