#------------------------------------------------------------------------------
#$Date: 2015-07-15 16:10:46 +0300 (Wed, 15 Jul 2015) $
#$Revision: 152082 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/75/7117508.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_7117508
loop_
_publ_author_name
'R. N. Prasad Tulichala'
'K. C. Kumara Swamy'
_publ_section_title
;
 Palladium-catalysed decarboxylative nitrile insertion via C-H activation
 or self-coupling of indole-2-carboxylic acids: a new route to
 indolocarbolines and triindoles
;
_journal_name_full               Chem.Commun.
_journal_page_first              12008
_journal_paper_doi               10.1039/C5cc03160e
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C20 H17 N3 O0'
_chemical_formula_weight         299.37
_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
_audit_update_record
;
2014-10-16 deposited with the CCDC.
2015-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.328(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.0546(9)
_cell_length_b                   5.5978(2)
_cell_length_c                   16.1901(6)
_cell_measurement_reflns_used    1415
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      71.4776
_cell_measurement_theta_min      2.6842
_cell_volume                     1490.66(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4593
_diffrn_reflns_theta_full        71.62
_diffrn_reflns_theta_max         71.62
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0583
_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)+(0.0833P)²+0.2273P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1492
_refine_ls_wR_factor_ref         0.1897
_reflns_number_gt                1816
_reflns_number_total             2844
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc03160e2-1.cif
_cod_data_source_block           Compound-9
_cod_database_code               7117508
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N 0.25910(14) 0.3572(4) 0.17562(13) 0.0495(6) Uani 1 1 d . . .
N2 N 0.28093(14) -0.0025(5) 0.40642(13) 0.0533(6) Uani 1 1 d . . .
C1 C 0.13753(17) -0.1114(5) 0.20187(15) 0.0450(6) Uani 1 1 d . . .
N1 N 0.17358(15) -0.2624(4) 0.33752(13) 0.0508(6) Uani 1 1 d . . .
C6 C 0.12145(17) -0.2903(5) 0.25706(16) 0.0495(7) Uani 1 1 d . . .
C10 C 0.31473(17) 0.3039(5) 0.31791(16) 0.0497(7) Uani 1 1 d . . .
C8 C 0.20455(16) 0.0299(5) 0.25323(15) 0.0454(6) Uani 1 1 d . . .
C13 C 0.31968(17) 0.5290(5) 0.20168(17) 0.0504(7) Uani 1 1 d . . .
C2 C 0.08820(18) -0.1058(5) 0.11842(16) 0.0544(7) Uani 1 1 d . . .
H9 H 0.0959 0.0119 0.0808 0.065 Uiso 1 1 calc R . .
C7 C 0.22351(17) -0.0689(5) 0.33648(15) 0.0477(7) Uani 1 1 d . . .
C12 C 0.35488(17) 0.5050(5) 0.28988(17) 0.0506(7) Uani 1 1 d . . .
C9 C 0.25459(17) 0.2224(5) 0.24512(15) 0.0455(6) Uani 1 1 d . . .
C20 C 0.2123(2) 0.3253(6) 0.08776(16) 0.0659(9) Uani 1 1 d . . .
H13A H 0.1582 0.3850 0.0810 0.099 Uiso 1 1 calc R . .
H13B H 0.2099 0.1585 0.0735 0.099 Uiso 1 1 calc R . .
H13C H 0.2377 0.4111 0.0505 0.099 Uiso 1 1 calc R . .
C11 C 0.32617(18) 0.1859(6) 0.39645(16) 0.0543(7) Uani 1 1 d . . .
C5 C 0.06142(18) -0.4606(6) 0.23003(18) 0.0579(8) Uani 1 1 d . . .
H15 H 0.0528 -0.5778 0.2674 0.069 Uiso 1 1 calc R . .
C18 C 0.1757(2) -0.4087(6) 0.41194(17) 0.0636(9) Uani 1 1 d . . .
H16A H 0.1308 -0.3673 0.4345 0.095 Uiso 1 1 calc R . .
H16B H 0.2258 -0.3816 0.4548 0.095 Uiso 1 1 calc R . .
H16C H 0.1718 -0.5742 0.3958 0.095 Uiso 1 1 calc R . .
C4 C 0.01482(19) -0.4527(6) 0.14671(19) 0.0618(8) Uani 1 1 d . . .
H17 H -0.0256 -0.5664 0.1271 0.074 Uiso 1 1 calc R . .
C3 C 0.0279(2) -0.2746(6) 0.09133(18) 0.0637(9) Uani 1 1 d . . .
H18 H -0.0046 -0.2698 0.0353 0.076 Uiso 1 1 calc R . .
C16 C 0.4393(2) 0.8412(6) 0.2806(2) 0.0686(9) Uani 1 1 d . . .
H19 H 0.4797 0.9490 0.3068 0.082 Uiso 1 1 calc R . .
C17 C 0.41597(19) 0.6659(6) 0.3295(2) 0.0617(8) Uani 1 1 d . . .
H20 H 0.4406 0.6552 0.3879 0.074 Uiso 1 1 calc R . .
C19 C 0.3923(2) 0.2602(7) 0.47382(18) 0.0781(11) Uani 1 1 d . . .
H21A H 0.3830 0.4217 0.4888 0.117 Uiso 1 1 calc R . .
H21B H 0.4440 0.2501 0.4610 0.117 Uiso 1 1 calc R . .
H21C H 0.3920 0.1563 0.5209 0.117 Uiso 1 1 calc R . .
C14 C 0.34312(19) 0.7053(6) 0.1525(2) 0.0615(8) Uani 1 1 d . . .
H22 H 0.3189 0.7187 0.0941 0.074 Uiso 1 1 calc R . .
C15 C 0.4036(2) 0.8589(6) 0.1939(2) 0.0674(9) Uani 1 1 d . . .
H23 H 0.4209 0.9778 0.1627 0.081 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C9 N3 C13 109.2(2) . .
C9 N3 C20 127.0(2) . .
C13 N3 C20 123.8(2) . .
C7 N2 C11 115.6(2) . .
C2 C1 C6 117.4(3) . .
C2 C1 C8 136.4(3) . .
C6 C1 C8 106.1(2) . .
C6 N1 C7 108.9(2) . .
C6 N1 C18 126.1(3) . .
C7 N1 C18 125.0(2) . .
N1 C6 C5 128.0(3) . .
N1 C6 C1 109.4(2) . .
C5 C6 C1 122.6(2) . .
C11 C10 C9 120.0(3) . .
C11 C10 C12 133.3(3) . .
C9 C10 C12 106.7(2) . .
C9 C8 C7 113.5(2) . .
C9 C8 C1 140.3(2) . .
C7 C8 C1 106.2(2) . .
C14 C13 N3 128.2(3) . .
C14 C13 C12 122.7(3) . .
N3 C13 C12 109.0(2) . .
C3 C2 C1 120.1(3) . .
C3 C2 H9 119.9 . .
C1 C2 H9 119.9 . .
N2 C7 N1 121.5(2) . .
N2 C7 C8 129.0(3) . .
N1 C7 C8 109.4(2) . .
C17 C12 C13 118.2(3) . .
C17 C12 C10 135.4(3) . .
C13 C12 C10 106.4(2) . .
N3 C9 C8 131.8(2) . .
N3 C9 C10 108.6(2) . .
C8 C9 C10 119.6(2) . .
N3 C20 H13A 109.5 . .
N3 C20 H13B 109.5 . .
H13A C20 H13B 109.5 . .
N3 C20 H13C 109.5 . .
H13A C20 H13C 109.5 . .
H13B C20 H13C 109.5 . .
N2 C11 C10 122.2(3) . .
N2 C11 C19 116.4(3) . .
C10 C11 C19 121.3(3) . .
C4 C5 C6 118.5(3) . .
C4 C5 H15 120.8 . .
C6 C5 H15 120.8 . .
N1 C18 H16A 109.5 . .
N1 C18 H16B 109.5 . .
H16A C18 H16B 109.5 . .
N1 C18 H16C 109.5 . .
H16A C18 H16C 109.5 . .
H16B C18 H16C 109.5 . .
C5 C4 C3 120.3(3) . .
C5 C4 H17 119.9 . .
C3 C4 H17 119.9 . .
C2 C3 C4 121.1(3) . .
C2 C3 H18 119.5 . .
C4 C3 H18 119.5 . .
C15 C16 C17 121.2(3) . .
C15 C16 H19 119.4 . .
C17 C16 H19 119.4 . .
C16 C17 C12 119.1(3) . .
C16 C17 H20 120.4 . .
C12 C17 H20 120.4 . .
C11 C19 H21A 109.5 . .
C11 C19 H21B 109.5 . .
H21A C19 H21B 109.5 . .
C11 C19 H21C 109.5 . .
H21A C19 H21C 109.5 . .
H21B C19 H21C 109.5 . .
C15 C14 C13 117.2(3) . .
C15 C14 H22 121.4 . .
C13 C14 H22 121.4 . .
C14 C15 C16 121.6(3) . .
C14 C15 H23 119.2 . .
C16 C15 H23 119.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N3 C9 1.374(3) .
N3 C13 1.393(3) .
N3 C20 1.446(3) .
N2 C7 1.339(3) .
N2 C11 1.341(4) .
C1 C2 1.391(3) .
C1 C6 1.416(4) .
C1 C8 1.456(4) .
N1 C6 1.378(3) .
N1 C7 1.381(4) .
N1 C18 1.450(3) .
C6 C5 1.382(4) .
C10 C11 1.400(4) .
C10 C9 1.418(3) .
C10 C12 1.452(4) .
C8 C9 1.402(4) .
C8 C7 1.413(3) .
C13 C14 1.391(4) .
C13 C12 1.401(4) .
C2 C3 1.381(4) .
C2 H9 0.9300 .
C12 C17 1.398(4) .
C20 H13A 0.9600 .
C20 H13B 0.9600 .
C20 H13C 0.9600 .
C11 C19 1.506(4) .
C5 C4 1.374(4) .
C5 H15 0.9300 .
C18 H16A 0.9600 .
C18 H16B 0.9600 .
C18 H16C 0.9600 .
C4 C3 1.397(4) .
C4 H17 0.9300 .
C3 H18 0.9300 .
C16 C15 1.378(4) .
C16 C17 1.383(5) .
C16 H19 0.9300 .
C17 H20 0.9300 .
C19 H21A 0.9600 .
C19 H21B 0.9600 .
C19 H21C 0.9600 .
C14 C15 1.373(4) .
C14 H22 0.9300 .
C15 H23 0.9300 .
