#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:21:29 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180179 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/75/7107535.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_7107535
loop_
_publ_author_name
'Jiangling Peng'
'Lanying Liu'
'Ziwei Hu'
'Jinbo Huang'
'Qiang Zhu'
_publ_section_title
;
 Direct carboxamidation of indoles by palladium-catalyzed C-H activation
 and isocyanide insertion
;
_journal_name_full               Chem.Commun.
_journal_page_first              3772
_journal_paper_doi               10.1039/c2cc30351e
_journal_volume                  48
_journal_year                    2012
_chemical_formula_moiety         'C14 H18 N2 O'
_chemical_formula_sum            'C14 H18 N2 O'
_chemical_formula_weight         230.30
_chemical_name_systematic
;
?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-01-13
_audit_creation_method
;
Olex2 1.1
(compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.3714(4)
_cell_length_b                   10.1800(3)
_cell_length_c                   20.7350(6)
_cell_measurement_temperature    293(2)
_cell_volume                     2611.38(14)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13008
_diffrn_reflns_theta_full        66.58
_diffrn_reflns_theta_max         66.58
_diffrn_reflns_theta_min         4.26
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.588
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.00105(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0421
_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)+(0.0578P)²+0.2394P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1224
_reflns_number_gt                1709
_reflns_number_total             2299
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc30351e.txt
_cod_data_source_block           d
_cod_original_cell_volume        2611.39(13)
_cod_database_code               7107535
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 '-x, y+1/2, -z+1/2'
4 'x+1/2, -y+1/2, -z'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 'x, -y-1/2, z-1/2'
8 '-x-1/2, y-1/2, z'
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
O1 O 0.31974(10) 0.16614(11) 0.32243(6) 0.0591(4) Uani 1 1 d .
N1 N 0.31881(11) 0.46659(13) 0.48645(6) 0.0535(4) Uani 1 1 d .
N2 N 0.21978(12) 0.34732(13) 0.29849(7) 0.0537(4) Uani 1 1 d .
H02 H 0.2088 0.4379 0.3108 0.078(6) Uiso 1 1 d R
C1 C 0.45724(16) 0.3468(2) 0.55215(9) 0.0646(5) Uani 1 1 d .
H1A H 0.4523 0.4006 0.5883 0.077 Uiso 1 1 calc R
C2 C 0.52625(18) 0.2422(2) 0.55038(11) 0.0761(6) Uani 1 1 d .
H2A H 0.5693 0.2241 0.5861 0.091 Uiso 1 1 calc R
C3 C 0.53345(17) 0.1616(2) 0.49590(10) 0.0728(6) Uani 1 1 d .
H3A H 0.5816 0.0915 0.4962 0.087 Uiso 1 1 calc R
C4 C 0.47139(15) 0.18333(18) 0.44196(9) 0.0585(5) Uani 1 1 d .
H4A H 0.4772 0.1290 0.4061 0.070 Uiso 1 1 calc R
C5 C 0.32139(13) 0.34112(15) 0.39717(7) 0.0461(4) Uani 1 1 d .
C6 C 0.27624(13) 0.44864(16) 0.42656(8) 0.0505(4) Uani 1 1 d .
H6A H 0.2237 0.5020 0.4081 0.061 Uiso 1 1 calc R
C7 C 0.39462(13) 0.36953(16) 0.49742(8) 0.0512(4) Uani 1 1 d .
C8 C 0.39925(13) 0.28904(16) 0.44232(8) 0.0475(4) Uani 1 1 d .
C9 C 0.28656(18) 0.5652(2) 0.53315(10) 0.0719(6) Uani 1 1 d .
H9A H 0.2350 0.6237 0.5138 0.108 Uiso 1 1 calc R
H9B H 0.3489 0.6142 0.5467 0.108 Uiso 1 1 calc R
H9C H 0.2544 0.5231 0.5699 0.108 Uiso 1 1 calc R
C10 C 0.28856(13) 0.27858(16) 0.33626(7) 0.0469(4) Uani 1 1 d .
C11 C 0.16741(16) 0.29802(17) 0.23939(8) 0.0579(5) Uani 1 1 d .
C12 C 0.1035(2) 0.1733(2) 0.25390(12) 0.0882(7) Uani 1 1 d .
H12A H 0.0537 0.1899 0.2885 0.132 Uiso 1 1 calc R
H12B H 0.1523 0.1045 0.2662 0.132 Uiso 1 1 calc R
H12C H 0.0641 0.1471 0.2161 0.132 Uiso 1 1 calc R
C13 C 0.2527(2) 0.2728(3) 0.18806(10) 0.0897(7) Uani 1 1 d .
H13A H 0.2875 0.3540 0.1770 0.135 Uiso 1 1 calc R
H13B H 0.2190 0.2364 0.1504 0.135 Uiso 1 1 calc R
H13C H 0.3055 0.2122 0.2044 0.135 Uiso 1 1 calc R
C14 C 0.0904(2) 0.4049(2) 0.21719(11) 0.0835(7) Uani 1 1 d .
H14A H 0.1301 0.4846 0.2099 0.125 Uiso 1 1 calc R
H14B H 0.0366 0.4196 0.2498 0.125 Uiso 1 1 calc R
H14C H 0.0559 0.3781 0.1779 0.125 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 N1 C7 108.48(13)
C6 N1 C9 126.53(15)
C7 N1 C9 124.89(15)
C10 N2 H02 115.4
C10 N2 C11 125.59(14)
C11 N2 H02 118.9
C2 C1 H1A 121.5
C2 C1 C7 117.08(18)
C7 C1 H1A 121.5
C1 C2 H2A 119.4
C1 C2 C3 121.25(18)
C3 C2 H2A 119.4
C2 C3 H3A 119.1
C4 C3 C2 121.83(18)
C4 C3 H3A 119.1
C3 C4 H4A 120.8
C3 C4 C8 118.41(17)
C8 C4 H4A 120.8
C6 C5 C8 106.06(14)
C6 C5 C10 127.89(15)
C8 C5 C10 125.57(14)
N1 C6 C5 110.78(14)
N1 C6 H6A 124.6
C5 C6 H6A 124.6
N1 C7 C1 129.08(16)
N1 C7 C8 108.09(14)
C1 C7 C8 122.83(16)
C4 C8 C5 134.82(16)
C4 C8 C7 118.59(15)
C7 C8 C5 106.59(14)
N1 C9 H9A 109.5
N1 C9 H9B 109.5
N1 C9 H9C 109.5
H9A C9 H9B 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
O1 C10 N2 122.62(15)
O1 C10 C5 120.76(14)
N2 C10 C5 116.55(14)
N2 C11 C12 110.31(15)
N2 C11 C13 109.52(17)
N2 C11 C14 106.50(14)
C13 C11 C12 110.95(19)
C14 C11 C12 109.33(19)
C14 C11 C13 110.13(17)
C11 C12 H12A 109.5
C11 C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12B 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C11 C13 H13A 109.5
C11 C13 H13B 109.5
C11 C13 H13C 109.5
H13A C13 H13B 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C11 C14 H14A 109.5
C11 C14 H14B 109.5
C11 C14 H14C 109.5
H14A C14 H14B 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C10 1.2415(19)
N1 C6 1.361(2)
N1 C7 1.381(2)
N1 C9 1.451(2)
N2 H02 0.9665
N2 C10 1.352(2)
N2 C11 1.474(2)
C1 H1A 0.9300
C1 C2 1.366(3)
C1 C7 1.393(2)
C2 H2A 0.9300
C2 C3 1.399(3)
C3 H3A 0.9300
C3 C4 1.375(3)
C4 H4A 0.9300
C4 C8 1.398(2)
C5 C6 1.372(2)
C5 C8 1.444(2)
C5 C10 1.472(2)
C6 H6A 0.9300
C7 C8 1.407(2)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C11 C12 1.525(3)
C11 C13 1.521(3)
C11 C14 1.517(3)
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H02 O1 0.97 2.36 3.3195(18) 170.5 8_665
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 C7 C8 C4 179.69(14)
N1 C7 C8 C5 -0.57(17)
C1 C2 C3 C4 -0.4(3)
C1 C7 C8 C4 -1.4(2)
C1 C7 C8 C5 178.39(16)
C2 C1 C7 N1 179.57(18)
C2 C1 C7 C8 0.9(3)
C2 C3 C4 C8 -0.1(3)
C3 C4 C8 C5 -178.69(18)
C3 C4 C8 C7 1.0(2)
C6 N1 C7 C1 -178.70(17)
C6 N1 C7 C8 0.16(18)
C6 C5 C8 C4 -179.57(18)
C6 C5 C8 C7 0.75(17)
C6 C5 C10 O1 -163.67(16)
C6 C5 C10 N2 13.4(2)
C7 N1 C6 C5 0.33(18)
C7 C1 C2 C3 0.0(3)
C8 C5 C6 N1 -0.68(18)
C8 C5 C10 O1 7.2(2)
C8 C5 C10 N2 -175.69(14)
C9 N1 C6 C5 -176.17(17)
C9 N1 C7 C1 -2.1(3)
C9 N1 C7 C8 176.74(17)
C10 N2 C11 C12 56.5(2)
C10 N2 C11 C13 -65.9(2)
C10 N2 C11 C14 175.05(18)
C10 C5 C6 N1 171.61(15)
C10 C5 C8 C4 7.9(3)
C10 C5 C8 C7 -171.77(14)
C11 N2 C10 O1 4.1(3)
C11 N2 C10 C5 -172.91(15)
