#------------------------------------------------------------------------------
#$Date: 2018-01-06 04:34:25 +0200 (Sat, 06 Jan 2018) $
#$Revision: 204889 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/78/1547827.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_1547827
loop_
_publ_author_name
'Gharpure, Santosh J.'
'Anuradha, Dandela'
_publ_section_title
;
 Synthesis of Benzo[1,4]heterocycles using Palladium Catalyzed Heck
 Reaction to Vinylogous Carbonates/Carbamates: Unexpected Formation of
 Indoles via Carbopalladation Intercepted by Nucleopalladation.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              6136
_journal_page_last               6139
_journal_paper_doi               10.1021/acs.orglett.7b03016
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C24 H27 N O5 S'
_chemical_formula_sum            'C24 H27 N O5 S'
_chemical_formula_weight         441.54
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                98.386(7)
_cell_angle_beta                 96.739(6)
_cell_angle_gamma                109.699(6)
_cell_formula_units_Z            2
_cell_length_a                   9.304(5)
_cell_length_b                   10.764(6)
_cell_length_c                   11.843(6)
_cell_measurement_reflns_used    2416
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.10
_cell_measurement_theta_min      3.10
_cell_volume                     1086.9(10)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b28'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b28'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9678
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             468.00
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.410
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3812
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0548P)²+0.2150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1207
_reflns_number_gt                3030
_reflns_number_total             3812
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            sjg-anu-6.cif
_cod_data_source_block           SJG-ANU-07-09
_cod_depositor_comments
'Adding full bibliography for 1547825--1547834.cif.'
_cod_database_code               1547827
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-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
S1 S -0.02154(7) 0.26540(6) 0.12124(5) 0.01743(18) Uani 1.0 2 d .
O1 O -0.06144(19) 0.15489(16) 0.02536(13) 0.0234(4) Uani 1.0 2 d .
O2 O -0.07973(18) 0.37150(15) 0.11333(13) 0.0219(4) Uani 1.0 2 d .
O3 O 0.32347(19) 0.31675(15) 0.36148(13) 0.0208(4) Uani 1.0 2 d .
O4 O 0.2503(2) 0.27744(16) 0.57888(14) 0.0263(5) Uani 1.0 2 d .
O5 O 0.2500(2) 0.46767(15) 0.68769(13) 0.0241(4) Uani 1.0 2 d .
N1 N 0.1678(3) 0.33501(18) 0.14819(15) 0.0165(5) Uani 1.0 2 d .
C1 C -0.2348(4) 0.0260(3) 0.5314(2) 0.0282(7) Uani 1.0 2 d .
C2 C -0.1762(3) 0.0870(3) 0.43136(19) 0.0201(6) Uani 1.0 2 d .
C3 C -0.1607(3) 0.0064(3) 0.3335(2) 0.0232(6) Uani 1.0 2 d .
C4 C -0.1108(3) 0.0611(3) 0.2400(2) 0.0207(6) Uani 1.0 2 d .
C5 C -0.0771(3) 0.1973(3) 0.24288(19) 0.0162(5) Uani 1.0 2 d .
C6 C -0.0908(3) 0.2796(3) 0.3391(2) 0.0181(6) Uani 1.0 2 d .
C7 C -0.1382(3) 0.2238(3) 0.4333(2) 0.0193(6) Uani 1.0 2 d .
C8 C 0.2566(3) 0.2440(3) 0.15205(19) 0.0180(6) Uani 1.0 2 d .
C9 C 0.3850(3) 0.2939(3) 0.25754(18) 0.0175(6) Uani 1.0 2 d .
C10 C 0.4617(3) 0.1920(3) 0.2685(2) 0.0225(6) Uani 1.0 2 d .
C11 C 0.5289(3) 0.1654(3) 0.1596(2) 0.0252(6) Uani 1.0 2 d .
C12 C 0.4056(3) 0.1226(3) 0.0505(2) 0.0248(6) Uani 1.0 2 d .
C13 C 0.3243(3) 0.2232(3) 0.0429(2) 0.0219(6) Uani 1.0 2 d .
C14 C 0.2447(3) 0.4770(3) 0.19023(19) 0.0171(5) Uani 1.0 2 d .
C15 C 0.2457(3) 0.5636(3) 0.1141(2) 0.0201(6) Uani 1.0 2 d .
C16 C 0.3204(3) 0.7016(3) 0.1525(2) 0.0250(6) Uani 1.0 2 d .
C17 C 0.3986(3) 0.7510(3) 0.2660(2) 0.0249(6) Uani 1.0 2 d .
C18 C 0.3972(3) 0.6654(3) 0.3424(2) 0.0214(6) Uani 1.0 2 d .
C19 C 0.3193(3) 0.5269(3) 0.3065(2) 0.0177(5) Uani 1.0 2 d .
C20 C 0.3072(3) 0.4368(3) 0.39151(19) 0.0176(6) Uani 1.0 2 d .
C21 C 0.2767(3) 0.4723(3) 0.49755(19) 0.0184(6) Uani 1.0 2 d .
C22 C 0.2579(3) 0.3926(3) 0.58720(19) 0.0162(5) Uani 1.0 2 d .
C23 C 0.2324(3) 0.4004(3) 0.78608(19) 0.0248(6) Uani 1.0 2 d .
C24 C 0.0653(3) 0.3158(3) 0.7814(3) 0.0297(7) Uani 1.0 2 d .
H1A H -0.2309 0.0975 0.5946 0.0338 Uiso 1.0 2 calc R
H1B H -0.1696 -0.0223 0.5589 0.0338 Uiso 1.0 2 calc R
H1C H -0.3421 -0.0369 0.5058 0.0338 Uiso 1.0 2 calc R
H3 H -0.1846 -0.0871 0.3310 0.0278 Uiso 1.0 2 calc R
H4 H -0.0997 0.0056 0.1741 0.0248 Uiso 1.0 2 calc R
H6 H -0.0680 0.3728 0.3408 0.0218 Uiso 1.0 2 calc R
H7 H -0.1448 0.2804 0.5004 0.0232 Uiso 1.0 2 calc R
H8 H 0.1833 0.1542 0.1593 0.0217 Uiso 1.0 2 calc R
H9 H 0.4644 0.3803 0.2494 0.0210 Uiso 1.0 2 calc R
H10A H 0.3848 0.1069 0.2792 0.0270 Uiso 1.0 2 calc R
H10B H 0.5458 0.2263 0.3374 0.0270 Uiso 1.0 2 calc R
H11A H 0.6145 0.2481 0.1544 0.0302 Uiso 1.0 2 calc R
H11B H 0.5722 0.0937 0.1652 0.0302 Uiso 1.0 2 calc R
H12A H 0.4548 0.1144 -0.0186 0.0298 Uiso 1.0 2 calc R
H12B H 0.3279 0.0331 0.0504 0.0298 Uiso 1.0 2 calc R
H13A H 0.2403 0.1894 -0.0259 0.0263 Uiso 1.0 2 calc R
H13B H 0.3993 0.3102 0.0340 0.0263 Uiso 1.0 2 calc R
H15 H 0.1951 0.5286 0.0356 0.0241 Uiso 1.0 2 calc R
H16 H 0.3180 0.7615 0.1015 0.0300 Uiso 1.0 2 calc R
H17 H 0.4537 0.8449 0.2916 0.0298 Uiso 1.0 2 calc R
H18 H 0.4500 0.7012 0.4202 0.0257 Uiso 1.0 2 calc R
H21 H 0.2666 0.5576 0.5151 0.0221 Uiso 1.0 2 calc R
H23A H 0.2707 0.4685 0.8591 0.0298 Uiso 1.0 2 calc R
H23B H 0.2955 0.3425 0.7855 0.0298 Uiso 1.0 2 calc R
H24A H 0.0540 0.2816 0.8534 0.0357 Uiso 1.0 2 calc R
H24B H 0.0319 0.2400 0.7154 0.0357 Uiso 1.0 2 calc R
H24C H 0.0010 0.3707 0.7724 0.0357 Uiso 1.0 2 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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(1992, 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_publ_flag
O1 S1 O2 120.17(11) yes
O1 S1 N1 106.86(11) yes
O1 S1 C5 107.25(11) yes
O2 S1 N1 106.73(11) yes
O2 S1 C5 108.29(12) yes
N1 S1 C5 106.86(11) yes
C9 O3 C20 117.71(19) yes
C22 O5 C23 115.7(2) yes
S1 N1 C8 117.25(14) yes
S1 N1 C14 121.39(19) yes
C8 N1 C14 120.09(19) yes
C1 C2 C3 120.5(3) yes
C1 C2 C7 121.2(3) yes
C3 C2 C7 118.3(3) yes
C2 C3 C4 120.8(3) yes
C3 C4 C5 119.8(3) yes
S1 C5 C4 119.69(19) yes
S1 C5 C6 119.71(19) yes
C4 C5 C6 120.6(3) yes
C5 C6 C7 119.1(3) yes
C2 C7 C6 121.4(3) yes
N1 C8 C9 111.18(19) yes
N1 C8 C13 113.2(2) yes
C9 C8 C13 109.6(2) yes
O3 C9 C8 110.4(2) yes
O3 C9 C10 108.6(2) yes
C8 C9 C10 110.65(19) yes
C9 C10 C11 110.0(3) yes
C10 C11 C12 111.4(3) yes
C11 C12 C13 111.7(2) yes
C8 C13 C12 110.1(3) yes
N1 C14 C15 118.93(19) yes
N1 C14 C19 120.2(3) yes
C15 C14 C19 120.9(2) yes
C14 C15 C16 120.0(2) yes
C15 C16 C17 119.4(3) yes
C16 C17 C18 120.8(2) yes
C17 C18 C19 120.7(2) yes
C14 C19 C18 118.1(3) yes
C14 C19 C20 121.41(19) yes
C18 C19 C20 120.3(2) yes
O3 C20 C19 119.7(2) yes
O3 C20 C21 119.7(3) yes
C19 C20 C21 120.5(3) yes
C20 C21 C22 126.1(3) yes
O4 C22 O5 122.8(3) yes
O4 C22 C21 127.5(3) yes
O5 C22 C21 109.7(2) yes
O5 C23 C24 110.9(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 1.4323(17) yes
S1 O2 1.429(2) yes
S1 N1 1.636(3) yes
S1 C5 1.763(3) yes
O3 C9 1.441(3) yes
O3 C20 1.352(4) yes
O4 C22 1.206(4) yes
O5 C22 1.362(3) yes
O5 C23 1.456(3) yes
N1 C8 1.481(4) yes
N1 C14 1.433(3) yes
C1 C2 1.506(4) yes
C2 C3 1.395(4) yes
C2 C7 1.391(4) yes
C3 C4 1.383(4) yes
C4 C5 1.386(4) yes
C5 C6 1.384(4) yes
C6 C7 1.389(4) yes
C8 C9 1.516(3) yes
C8 C13 1.523(4) yes
C9 C10 1.509(5) yes
C10 C11 1.529(4) yes
C11 C12 1.523(4) yes
C12 C13 1.522(5) yes
C14 C15 1.387(4) yes
C14 C19 1.405(3) yes
C15 C16 1.388(4) yes
C16 C17 1.385(4) yes
C17 C18 1.380(4) yes
C18 C19 1.394(3) yes
C19 C20 1.485(4) yes
C20 C21 1.349(4) yes
C21 C22 1.450(4) yes
C23 C24 1.503(4) yes
