#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/85/1508597.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_1508597
loop_
_publ_author_name
'Liu, Bingxin'
'Hong, Xiaohu'
'Yan, Dong'
'Xu, Shuguang'
'Huang, Xiaomei'
'Xu, Bin'
_publ_section_title
;
 Palladium-catalyzed tandem allenyl and aryl C-N bond formation: efficient
 access to N-functionalized multisubstituted indoles.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4398
_journal_page_last               4401
_journal_paper_doi               10.1021/ol3018775
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C17 H15 N O2'
_chemical_formula_weight         265.30
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                90.000(5)
_cell_angle_beta                 100.261(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            8
_cell_length_a                   12.391(5)
_cell_length_b                   11.044(5)
_cell_length_c                   20.158(5)
_cell_measurement_reflns_used    2350
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.2
_cell_measurement_theta_min      2.2
_cell_volume                     2714.4(18)
_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      295(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6427
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0014(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2379
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0645
_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)+(0.0883P)²+0.3048P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1606
_refine_ls_wR_factor_ref         0.1911
_reflns_number_gt                1535
_reflns_number_total             2379
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3018775_si_002.cif
_cod_data_source_block           hxh-1-110
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1508597
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'
'-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 1.03559(16) -0.1102(2) 0.63807(11) 0.0473(6) Uani 1 1 d .
O22 O 0.90151(16) -0.4331(2) 0.53385(12) 0.0745(7) Uani 1 1 d .
O21 O 1.07923(16) -0.4413(2) 0.57376(11) 0.0690(7) Uani 1 1 d .
H21A H 1.0778 -0.4833 0.5401 0.104 Uiso 1 1 calc R
C7 C 0.8764(2) -0.1462(3) 0.56870(15) 0.0566(8) Uani 1 1 d .
H7 H 0.8148 -0.1856 0.5454 0.068 Uiso 1 1 calc R
C12 C 1.2174(2) -0.2004(3) 0.66432(16) 0.0576(8) Uani 1 1 d .
H12 H 1.2038 -0.2424 0.6237 0.069 Uiso 1 1 calc R
C8 C 0.9590(2) -0.1980(2) 0.61275(14) 0.0481(7) Uani 1 1 d .
C2 C 1.0000(2) 0.0000(2) 0.60844(13) 0.0462(7) Uani 1 1 d .
C1 C 0.9008(2) -0.0207(3) 0.56453(14) 0.0489(7) Uani 1 1 d .
C14 C 1.3374(3) -0.1484(4) 0.76605(19) 0.0725(10) Uani 1 1 d .
H14 H 1.4051 -0.1555 0.7943 0.087 Uiso 1 1 calc R
C22 C 0.9830(2) -0.4067(3) 0.57715(15) 0.0507(7) Uani 1 1 d .
C21 C 0.9692(2) -0.3281(2) 0.63603(14) 0.0544(8) Uani 1 1 d .
H21 H 1.0348 -0.3358 0.6709 0.065 Uiso 1 1 calc R
C15 C 1.2592(2) -0.0748(3) 0.78406(16) 0.0658(9) Uani 1 1 d .
H15 H 1.2738 -0.0320 0.8244 0.079 Uiso 1 1 calc R
C11 C 1.13778(19) -0.1262(3) 0.68237(14) 0.0461(7) Uani 1 1 d .
C3 C 1.0491(2) 0.1125(3) 0.61597(15) 0.0558(8) Uani 1 1 d .
H3 H 1.1151 0.1246 0.6453 0.067 Uiso 1 1 calc R
C16 C 1.1590(2) -0.0641(3) 0.74268(14) 0.0548(8) Uani 1 1 d .
H16 H 1.1052 -0.0149 0.7553 0.066 Uiso 1 1 calc R
C4 C 0.9965(2) 0.2058(3) 0.57849(16) 0.0609(8) Uani 1 1 d .
H4 H 1.0278 0.2826 0.5826 0.073 Uiso 1 1 calc R
C6 C 0.8501(2) 0.0768(3) 0.52702(16) 0.0601(8) Uani 1 1 d .
H6 H 0.7844 0.0655 0.4972 0.072 Uiso 1 1 calc R
C5 C 0.8973(2) 0.1884(3) 0.53438(16) 0.0624(8) Uani 1 1 d .
H5 H 0.8633 0.2535 0.5099 0.075 Uiso 1 1 calc R
C13 C 1.3175(2) -0.2119(3) 0.70696(19) 0.0708(10) Uani 1 1 d .
H13 H 1.3711 -0.2627 0.6954 0.085 Uiso 1 1 calc R
C23 C 0.8701(3) -0.3681(3) 0.66550(19) 0.0788(11) Uani 1 1 d .
H23A H 0.8628 -0.3170 0.7030 0.118 Uiso 1 1 calc R
H23B H 0.8798 -0.4505 0.6805 0.118 Uiso 1 1 calc R
H23C H 0.8052 -0.3619 0.6316 0.118 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 0.0016 '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
C8 N1 C2 108.0(2)
C8 N1 C11 128.1(2)
C2 N1 C11 123.8(2)
C8 C7 C1 107.8(2)
C11 C12 C13 119.6(3)
C7 C8 N1 109.4(2)
C7 C8 C21 128.1(3)
N1 C8 C21 122.4(2)
C3 C2 N1 129.8(2)
C3 C2 C1 122.5(3)
N1 C2 C1 107.7(2)
C6 C1 C2 118.4(3)
C6 C1 C7 134.5(3)
C2 C1 C7 107.1(2)
C15 C14 C13 120.8(3)
O22 C22 O21 123.1(3)
O22 C22 C21 119.7(2)
O21 C22 C21 117.2(3)
C22 C21 C8 108.6(2)
C22 C21 C23 110.7(2)
C8 C21 C23 111.7(3)
C14 C15 C16 119.9(3)
C16 C11 C12 119.6(3)
C16 C11 N1 120.0(2)
C12 C11 N1 120.4(3)
C4 C3 C2 117.3(3)
C15 C16 C11 120.2(3)
C3 C4 C5 121.7(3)
C5 C6 C1 119.7(3)
C6 C5 C4 120.5(3)
C14 C13 C12 119.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C8 1.389(3)
N1 C2 1.392(3)
N1 C11 1.425(3)
O22 C22 1.246(3)
O21 C22 1.266(3)
C7 C8 1.356(4)
C7 C1 1.425(4)
C12 C11 1.380(4)
C12 C13 1.383(4)
C8 C21 1.509(4)
C2 C3 1.380(4)
C2 C1 1.400(4)
C1 C6 1.399(4)
C14 C15 1.362(5)
C14 C13 1.366(5)
C22 C21 1.505(4)
C21 C23 1.521(4)
C15 C16 1.372(4)
C11 C16 1.379(4)
C3 C4 1.372(4)
C4 C5 1.396(4)
C6 C5 1.361(4)
