#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/73/4027393.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_4027393
loop_
_publ_author_name
'R. Rama Suresh'
'K. C. Kumara Swamy'
_publ_section_title
;
 Palladium-Catalyzed Annulation of Allenes with Indole-2-carboxylic Acid
 Derivatives: Synthesis of Indolo[2,3-c]pyrane-1-ones via Ar-I Reactivity
 or C-H Functionalization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6959
_journal_page_last               6969
_journal_paper_doi               10.1021/jo301149s
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C16 H15 N O4'
_chemical_formula_sum            'C16 H15 N O4'
_chemical_formula_weight         285.29
_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                 103.842(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.362(3)
_cell_length_b                   13.883(3)
_cell_length_c                   7.8491(17)
_cell_measurement_temperature    273(2)
_cell_volume                     1413.8(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13301
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_correction_T_min  0.9715
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS, Sheldric (1996)'
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0638P)²+0.4598P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1351
_reflns_number_gt                2096
_reflns_number_total             2484
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301149s_si_002_4.cif
_cod_data_source_block           compd-37
_cod_original_cell_volume        1413.7(6)
_cod_database_code               4027393
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
N1 N 0.59586(13) 0.05972(17) 0.1864(2) 0.0744(6) Uani 1 1 d .
O1 O 0.54095(14) 0.26911(17) 0.1253(3) 0.1147(8) Uani 1 1 d .
O2 O 0.68892(12) 0.28976(11) 0.0529(2) 0.0756(5) Uani 1 1 d .
O3 O 0.97445(12) 0.13990(13) 0.37046(19) 0.0818(5) Uani 1 1 d .
O4 O 1.07364(10) 0.07035(10) 0.21674(17) 0.0618(4) Uani 1 1 d .
C1 C 0.49754(18) 0.0678(3) 0.2370(4) 0.1066(11) Uani 1 1 d .
H1A H 0.4619 0.0072 0.2176 0.160 Uiso 1 1 calc R
H1B H 0.4561 0.1168 0.1676 0.160 Uiso 1 1 calc R
H1C H 0.5102 0.0846 0.3589 0.160 Uiso 1 1 calc R
C2 C 0.65415(19) -0.02267(19) 0.1945(3) 0.0706(6) Uani 1 1 d .
C3 C 0.6305(3) -0.1167(3) 0.2351(3) 0.1058(11) Uani 1 1 d .
H3 H 0.5687 -0.1311 0.2641 0.127 Uiso 1 1 calc R
C4 C 0.7014(4) -0.1863(2) 0.2307(4) 0.1264(14) Uani 1 1 d .
H4 H 0.6878 -0.2494 0.2576 0.152 Uiso 1 1 calc R
C5 C 0.7931(3) -0.16535(18) 0.1870(4) 0.1030(10) Uani 1 1 d .
H5 H 0.8395 -0.2149 0.1841 0.124 Uiso 1 1 calc R
C6 C 0.8176(2) -0.07415(15) 0.1482(3) 0.0718(6) Uani 1 1 d .
H6 H 0.8800 -0.0613 0.1201 0.086 Uiso 1 1 calc R
C7 C 0.74727(15) -0.00025(14) 0.1513(2) 0.0561(5) Uani 1 1 d .
C8 C 0.74425(13) 0.10090(13) 0.1155(2) 0.0489(4) Uani 1 1 d .
C9 C 0.81461(13) 0.16718(13) 0.0666(2) 0.0487(4) Uani 1 1 d .
C10 C 0.78239(16) 0.25718(15) 0.0366(3) 0.0621(5) Uani 1 1 d .
H10 H 0.8264 0.3010 0.0022 0.074 Uiso 1 1 calc R
C11 C 0.61902(17) 0.2318(2) 0.1080(3) 0.0740(7) Uani 1 1 d .
C12 C 0.65110(14) 0.13427(16) 0.1371(2) 0.0581(5) Uani 1 1 d .
C13 C 0.92112(14) 0.13918(14) 0.0556(2) 0.0529(5) Uani 1 1 d .
H13A H 0.9509 0.1912 0.0014 0.064 Uiso 1 1 calc R
H13B H 0.9171 0.0828 -0.0188 0.064 Uiso 1 1 calc R
C14 C 0.99053(14) 0.11744(13) 0.2325(2) 0.0500(4) Uani 1 1 d .
C15 C 1.14977(17) 0.04654(18) 0.3771(3) 0.0726(6) Uani 1 1 d .
H15A H 1.1251 -0.0062 0.4371 0.087 Uiso 1 1 calc R
H15B H 1.1619 0.1018 0.4551 0.087 Uiso 1 1 calc R
C16 C 1.24567(18) 0.0188(2) 0.3299(3) 0.0846(7) Uani 1 1 d .
H16A H 1.2324 -0.0344 0.2495 0.127 Uiso 1 1 calc R
H16B H 1.2961 0.0003 0.4337 0.127 Uiso 1 1 calc R
H16C H 1.2712 0.0724 0.2755 0.127 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
C2 N1 C12 107.55(17)
C2 N1 C1 125.8(2)
C12 N1 C1 126.4(2)
C10 O2 C11 122.73(17)
C14 O4 C15 117.48(15)
N1 C1 H1A 109.5
N1 C1 H1B 109.5
H1A C1 H1B 109.5
N1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 C3 129.1(3)
N1 C2 C7 109.25(19)
C3 C2 C7 121.7(3)
C4 C3 C2 117.4(3)
C4 C3 H3 121.3
C2 C3 H3 121.3
C3 C4 C5 121.5(3)
C3 C4 H4 119.2
C5 C4 H4 119.2
C6 C5 C4 121.8(3)
C6 C5 H5 119.1
C4 C5 H5 119.1
C5 C6 C7 118.8(3)
C5 C6 H6 120.6
C7 C6 H6 120.6
C6 C7 C2 118.8(2)
C6 C7 C8 134.88(18)
C2 C7 C8 106.31(19)
C12 C8 C7 106.85(17)
C12 C8 C9 119.20(18)
C7 C8 C9 133.95(17)
C10 C9 C8 116.60(17)
C10 C9 C13 120.50(17)
C8 C9 C13 122.86(16)
C9 C10 O2 124.24(19)
C9 C10 H10 117.9
O2 C10 H10 117.9
O1 C11 O2 117.1(2)
O1 C11 C12 129.0(3)
O2 C11 C12 113.91(17)
C8 C12 N1 110.03(19)
C8 C12 C11 123.19(19)
N1 C12 C11 126.76(19)
C9 C13 C14 112.54(14)
C9 C13 H13A 109.1
C14 C13 H13A 109.1
C9 C13 H13B 109.1
C14 C13 H13B 109.1
H13A C13 H13B 107.8
O3 C14 O4 123.50(18)
O3 C14 C13 125.40(17)
O4 C14 C13 111.10(15)
O4 C15 C16 108.23(17)
O4 C15 H15A 110.1
C16 C15 H15A 110.1
O4 C15 H15B 110.1
C16 C15 H15B 110.1
H15A C15 H15B 108.4
C15 C16 H16A 109.5
C15 C16 H16B 109.5
H16A C16 H16B 109.5
C15 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.377(3)
N1 C12 1.379(3)
N1 C1 1.465(3)
O1 C11 1.201(2)
O2 C10 1.363(2)
O2 C11 1.378(3)
O3 C14 1.195(2)
O4 C14 1.320(2)
O4 C15 1.455(3)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C3 1.398(4)
C2 C7 1.400(3)
C3 C4 1.359(5)
C3 H3 0.9300
C4 C5 1.380(5)
C4 H4 0.9300
C5 C6 1.360(3)
C5 H5 0.9300
C6 C7 1.395(3)
C6 H6 0.9300
C7 C8 1.431(3)
C8 C12 1.376(3)
C8 C9 1.432(2)
C9 C10 1.324(3)
C9 C13 1.498(2)
C10 H10 0.9300
C11 C12 1.422(3)
C13 C14 1.504(3)
C13 H13A 0.9700
C13 H13B 0.9700
C15 C16 1.468(3)
C15 H15A 0.9700
C15 H15B 0.9700
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659525
