#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:36:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180189 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/85/7108548.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_7108548
loop_
_publ_author_name
'Qi Xing'
'Lijun Shi'
'Rui Lang'
'Chungu Xia'
'Fuwei Li'
_publ_section_title
;
 Palladium-catalyzed mono- and double-carbonylation of indoles with amines
 controllably leading to amides and alpha-ketoamides
;
_journal_name_full               Chem.Commun.
_journal_page_first              11023
_journal_paper_doi               10.1039/c2cc36341k
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C18 H15 N2 O2'
_chemical_formula_weight         291.32
_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                 97.577(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.604(3)
_cell_length_b                   17.584(7)
_cell_length_c                   10.173(4)
_cell_measurement_reflns_used    2303
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.21
_cell_measurement_theta_min      2.32
_cell_volume                     1525.7(10)
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7216
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9867
_exptl_absorpt_correction_T_min  0.9809
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0569
_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/[\s^2^(Fo^2^)+(0.0734P)^2^+0.0791P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1587
_reflns_number_gt                1700
_reflns_number_total             2810
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc36341k.txt
_cod_data_source_block           p21ca
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7108548
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 0.3872(3) 0.56231(13) 0.8437(2) 0.0466(6) Uani 1 1 d .
C2 C 0.3009(3) 0.50281(14) 0.8986(2) 0.0461(6) Uani 1 1 d .
C3 C 0.2452(3) 0.43096(14) 0.8566(3) 0.0571(7) Uani 1 1 d .
H3 H 0.2636 0.4118 0.7748 0.069 Uiso 1 1 calc R
C4 C 0.1629(3) 0.38918(16) 0.9380(3) 0.0645(8) Uani 1 1 d .
H4 H 0.1261 0.3412 0.9105 0.077 Uiso 1 1 calc R
C5 C 0.1328(3) 0.41661(17) 1.0607(3) 0.0646(8) Uani 1 1 d .
H5 H 0.0776 0.3866 1.1139 0.077 Uiso 1 1 calc R
C6 C 0.1835(3) 0.48737(16) 1.1041(3) 0.0590(7) Uani 1 1 d .
H6 H 0.1624 0.5065 1.1851 0.071 Uiso 1 1 calc R
C7 C 0.2673(3) 0.52890(14) 1.0220(2) 0.0494(6) Uani 1 1 d .
C8 C 0.4018(3) 0.62068(14) 0.9357(2) 0.0537(7) Uani 1 1 d .
H8 H 0.4530 0.6665 0.9259 0.064 Uiso 1 1 calc R
C9 C 0.4512(3) 0.55896(14) 0.7208(3) 0.0497(6) Uani 1 1 d .
C10 C 0.5302(3) 0.62970(15) 0.6692(3) 0.0517(7) Uani 1 1 d .
C11 C 0.6515(3) 0.67834(15) 0.4834(3) 0.0595(7) Uani 1 1 d .
H11A H 0.6335 0.7263 0.5261 0.071 Uiso 1 1 calc R
H11B H 0.5993 0.6810 0.3930 0.071 Uiso 1 1 calc R
C12 C 0.8246(3) 0.66962(15) 0.4797(2) 0.0540(7) Uani 1 1 d .
C13 C 0.8962(3) 0.71537(16) 0.3953(3) 0.0684(8) Uani 1 1 d .
H13 H 0.8360 0.7492 0.3396 0.082 Uiso 1 1 calc R
C14 C 1.0556(4) 0.7117(2) 0.3923(4) 0.0953(11) Uani 1 1 d .
H14 H 1.1028 0.7437 0.3364 0.114 Uiso 1 1 calc R
C15 C 1.1433(4) 0.6615(3) 0.4708(4) 0.1306(17) Uani 1 1 d .
H15 H 1.2508 0.6585 0.4687 0.157 Uiso 1 1 calc R
C16 C 1.0729(5) 0.6152(4) 0.5535(4) 0.162(2) Uani 1 1 d .
H16 H 1.1332 0.5805 0.6072 0.195 Uiso 1 1 calc R
C17 C 0.9141(4) 0.6193(2) 0.5582(3) 0.1033(13) Uani 1 1 d .
H17 H 0.8679 0.5876 0.6151 0.124 Uiso 1 1 calc R
C18 C 0.3240(4) 0.64783(17) 1.1597(3) 0.0818(10) Uani 1 1 d .
H18A H 0.3813 0.6942 1.1527 0.123 Uiso 1 1 calc R
H18B H 0.3693 0.6202 1.2366 0.123 Uiso 1 1 calc R
H18C H 0.2166 0.6596 1.1674 0.123 Uiso 1 1 calc R
N1 N 0.3312(2) 0.60158(12) 1.0413(2) 0.0558(6) Uani 1 1 d .
N2 N 0.5798(2) 0.61818(12) 0.5517(2) 0.0556(6) Uani 1 1 d .
O1 O 0.4432(2) 0.50143(10) 0.65099(17) 0.0664(6) Uani 1 1 d .
O2 O 0.5411(2) 0.69032(10) 0.72980(18) 0.0748(6) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0471(14) 0.0495(15) 0.0427(14) -0.0025(12) 0.0036(11) 0.0060(11)
C2 0.0466(13) 0.0477(15) 0.0425(14) 0.0012(12) 0.0009(10) 0.0060(12)
C3 0.0661(17) 0.0562(17) 0.0488(15) -0.0034(13) 0.0067(13) 0.0001(14)
C4 0.0753(19) 0.0555(17) 0.0626(19) 0.0026(15) 0.0091(15) -0.0075(14)
C5 0.0660(18) 0.0649(19) 0.0637(19) 0.0153(15) 0.0122(14) 0.0015(15)
C6 0.0627(16) 0.0665(19) 0.0485(15) 0.0035(14) 0.0101(13) 0.0102(14)
C7 0.0490(14) 0.0507(16) 0.0471(15) 0.0013(12) 0.0012(11) 0.0098(12)
C8 0.0561(15) 0.0534(16) 0.0512(16) 0.0004(13) 0.0060(12) 0.0001(13)
C9 0.0495(14) 0.0474(15) 0.0512(16) -0.0026(13) 0.0026(12) 0.0011(12)
C10 0.0515(15) 0.0495(16) 0.0524(16) 0.0010(13) 0.0002(12) 0.0011(12)
C11 0.0597(16) 0.0612(17) 0.0581(16) 0.0076(14) 0.0101(13) 0.0022(13)
C12 0.0528(15) 0.0664(18) 0.0429(14) -0.0099(13) 0.0065(12) -0.0026(13)
C13 0.0696(19) 0.0647(18) 0.075(2) -0.0108(16) 0.0232(15) -0.0058(15)
C14 0.077(2) 0.123(3) 0.092(3) -0.025(2) 0.033(2) -0.021(2)
C15 0.050(2) 0.247(6) 0.095(3) -0.004(3) 0.012(2) 0.008(3)
C16 0.074(3) 0.306(7) 0.104(3) 0.068(4) 0.000(2) 0.047(4)
C17 0.059(2) 0.172(4) 0.078(2) 0.040(2) 0.0072(17) 0.025(2)
C18 0.118(3) 0.073(2) 0.0574(18) -0.0233(16) 0.0219(17) -0.0012(18)
N1 0.0649(14) 0.0542(14) 0.0484(13) -0.0072(11) 0.0079(11) 0.0048(11)
N2 0.0591(13) 0.0594(14) 0.0504(13) 0.0036(11) 0.0157(10) -0.0015(10)
O1 0.0899(14) 0.0553(11) 0.0575(11) -0.0137(10) 0.0233(10) -0.0093(10)
O2 0.1099(17) 0.0517(12) 0.0662(13) -0.0125(10) 0.0237(11) -0.0118(11)
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 C1 C9 127.6(2)
C8 C1 C2 106.4(2)
C9 C1 C2 125.9(2)
C3 C2 C7 117.8(2)
C3 C2 C1 135.4(2)
C7 C2 C1 106.7(2)
C4 C3 C2 118.9(2)
C4 C3 H3 120.6
C2 C3 H3 120.6
C3 C4 C5 121.8(3)
C3 C4 H4 119.1
C5 C4 H4 119.1
C6 C5 C4 120.9(3)
C6 C5 H5 119.6
C4 C5 H5 119.6
C5 C6 C7 117.0(3)
C5 C6 H6 121.5
C7 C6 H6 121.5
C6 C7 N1 128.8(2)
C6 C7 C2 123.6(2)
N1 C7 C2 107.6(2)
N1 C8 C1 110.2(2)
N1 C8 H8 124.9
C1 C8 H8 124.9
O1 C9 C1 122.5(2)
O1 C9 C10 117.4(2)
C1 C9 C10 120.1(2)
O2 C10 N2 124.6(2)
O2 C10 C9 122.5(2)
N2 C10 C9 112.9(2)
N2 C11 C12 115.1(2)
N2 C11 H11A 108.5
C12 C11 H11A 108.5
N2 C11 H11B 108.5
C12 C11 H11B 108.5
H11A C11 H11B 107.5
C17 C12 C13 118.6(3)
C17 C12 C11 122.5(3)
C13 C12 C11 118.8(2)
C12 C13 C14 121.0(3)
C12 C13 H13 119.5
C14 C13 H13 119.5
C15 C14 C13 119.8(4)
C15 C14 H14 120.1
C13 C14 H14 120.1
C14 C15 C16 119.7(4)
C14 C15 H15 120.2
C16 C15 H15 120.2
C15 C16 C17 120.8(4)
C15 C16 H16 119.6
C17 C16 H16 119.6
C12 C17 C16 120.2(4)
C12 C17 H17 119.9
C16 C17 H17 119.9
N1 C18 H18A 109.5
N1 C18 H18B 109.5
H18A C18 H18B 109.5
N1 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C8 N1 C7 109.1(2)
C8 N1 C18 126.3(2)
C7 N1 C18 124.6(2)
C10 N2 C11 121.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C8 1.383(3)
C1 C9 1.433(3)
C1 C2 1.438(3)
C2 C3 1.398(3)
C2 C7 1.402(3)
C3 C4 1.372(3)
C3 H3 0.9300
C4 C5 1.394(4)
C4 H4 0.9300
C5 C6 1.372(4)
C5 H5 0.9300
C6 C7 1.381(4)
C6 H6 0.9300
C7 N1 1.395(3)
C8 N1 1.345(3)
C8 H8 0.9300
C9 O1 1.233(3)
C9 C10 1.542(3)
C10 O2 1.229(3)
C10 N2 1.337(3)
C11 N2 1.448(3)
C11 C12 1.502(3)
C11 H11A 0.9700
C11 H11B 0.9700
C12 C17 1.361(4)
C12 C13 1.380(4)
C13 C14 1.378(4)
C13 H13 0.9300
C14 C15 1.351(5)
C14 H14 0.9300
C15 C16 1.369(6)
C15 H15 0.9300
C16 C17 1.375(5)
C16 H16 0.9300
C17 H17 0.9300
C18 N1 1.461(3)
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 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
C8 C1 C2 C3 178.6(3)
C9 C1 C2 C3 -4.3(4)
C8 C1 C2 C7 0.2(2)
C9 C1 C2 C7 177.3(2)
C7 C2 C3 C4 -0.9(3)
C1 C2 C3 C4 -179.2(2)
C2 C3 C4 C5 0.4(4)
C3 C4 C5 C6 0.7(4)
C4 C5 C6 C7 -1.1(4)
C5 C6 C7 N1 179.7(2)
C5 C6 C7 C2 0.6(3)
C3 C2 C7 C6 0.5(3)
C1 C2 C7 C6 179.2(2)
C3 C2 C7 N1 -178.8(2)
C1 C2 C7 N1 -0.1(2)
C9 C1 C8 N1 -177.3(2)
C2 C1 C8 N1 -0.2(3)
C8 C1 C9 O1 173.4(2)
C2 C1 C9 O1 -3.1(4)
C8 C1 C9 C10 -8.2(4)
C2 C1 C9 C10 175.2(2)
O1 C9 C10 O2 178.4(2)
C1 C9 C10 O2 0.0(3)
O1 C9 C10 N2 0.3(3)
C1 C9 C10 N2 -178.2(2)
N2 C11 C12 C17 -14.0(4)
N2 C11 C12 C13 167.3(2)
C17 C12 C13 C14 -1.5(4)
C11 C12 C13 C14 177.3(3)
C12 C13 C14 C15 1.5(5)
C13 C14 C15 C16 -0.5(7)
C14 C15 C16 C17 -0.3(8)
C13 C12 C17 C16 0.6(5)
C11 C12 C17 C16 -178.1(4)
C15 C16 C17 C12 0.3(8)
C1 C8 N1 C7 0.1(3)
C1 C8 N1 C18 178.9(2)
C6 C7 N1 C8 -179.2(2)
C2 C7 N1 C8 0.0(3)
C6 C7 N1 C18 1.9(4)
C2 C7 N1 C18 -178.8(2)
O2 C10 N2 C11 -0.6(4)
C9 C10 N2 C11 177.5(2)
C12 C11 N2 C10 108.9(3)