#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/81/7108147.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_7108147
loop_
_publ_author_name
'Yu-Ting Lee'
'Yeong-Jiunn Jang'
'Siang-en Syu'
'Shu-Chi Chou'
'Chia-Jui Lee'
'Wenwei Lin'
_publ_section_title
;
 Preparation of functional benzofurans and indoles via chemoselective
 intramolecular Wittig reactions
;
_journal_name_full               Chem.Commun.
_journal_page_first              8135
_journal_paper_doi               10.1039/c2cc33972b
_journal_volume                  48
_journal_year                    2012
_chemical_formula_moiety         'C29 H18 Cl N O4 S'
_chemical_formula_sum            'C29 H18 Cl N O4 S'
_chemical_formula_weight         511.95
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                78.4510(10)
_cell_angle_beta                 87.408(2)
_cell_angle_gamma                78.835(2)
_cell_formula_units_Z            2
_cell_length_a                   8.1399(2)
_cell_length_b                   12.4092(3)
_cell_length_c                   12.5776(4)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1221.15(6)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10643
_diffrn_reflns_theta_full        25.39
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  0.9463
_exptl_absorpt_correction_T_min  0.9234
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4442
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0663P)²+0.2010P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1199
_reflns_number_gt                3691
_reflns_number_total             4442
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc33972b.txt
_cod_data_source_block           a13651
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value ' multi-scan' changed to
'multi-scan' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               7108147
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
C1 C -0.2357(2) 0.67391(15) 0.07903(15) 0.0357(4) Uani 1 1 d .
C2 C -0.3144(3) 0.75578(17) 0.13307(18) 0.0425(5) Uani 1 1 d .
H2 H -0.4315 0.7834 0.1260 0.051 Uiso 1 1 calc R
C3 C -0.2190(2) 0.79673(16) 0.19784(16) 0.0378(4) Uani 1 1 d .
H3 H -0.2707 0.8529 0.2364 0.045 Uiso 1 1 calc R
C4 C -0.0485(2) 0.75656(14) 0.20698(14) 0.0279(4) Uani 1 1 d .
C5 C 0.0278(2) 0.67563(15) 0.14947(15) 0.0338(4) Uani 1 1 d .
H5 H 0.1454 0.6494 0.1542 0.041 Uiso 1 1 calc R
C6 C -0.0670(3) 0.63320(16) 0.08549(15) 0.0371(4) Uani 1 1 d .
H6 H -0.0162 0.5769 0.0467 0.045 Uiso 1 1 calc R
C7 C 0.0452(2) 0.79792(14) 0.28427(14) 0.0281(4) Uani 1 1 d .
C8 C 0.3126(2) 0.79604(15) 0.34771(14) 0.0293(4) Uani 1 1 d .
C9 C 0.3734(2) 0.90064(15) 0.30387(15) 0.0330(4) Uani 1 1 d .
C10 C 0.3344(3) 0.95845(17) 0.19977(18) 0.0461(5) Uani 1 1 d .
H10 H 0.2669 0.9305 0.1560 0.055 Uiso 1 1 calc R
C11 C 0.3920(3) 1.0567(2) 0.1578(2) 0.0627(7) Uani 1 1 d .
H11 H 0.3640 1.0953 0.0859 0.075 Uiso 1 1 calc R
C12 C 0.4897(3) 1.09842(19) 0.2204(2) 0.0626(7) Uani 1 1 d .
H12 H 0.5285 1.1660 0.1921 0.075 Uiso 1 1 calc R
C13 C 0.5301(3) 1.0418(2) 0.3232(2) 0.0604(7) Uani 1 1 d .
H13 H 0.5983 1.0701 0.3662 0.072 Uiso 1 1 calc R
C14 C 0.4733(3) 0.94377(18) 0.36585(18) 0.0470(5) Uani 1 1 d .
H14 H 0.5024 0.9056 0.4377 0.056 Uiso 1 1 calc R
C15 C 0.3417(2) 0.73062(15) 0.44499(14) 0.0306(4) Uani 1 1 d .
H15 H 0.4105 0.7536 0.4919 0.037 Uiso 1 1 calc R
C16 C 0.2797(2) 0.62685(14) 0.48828(14) 0.0287(4) Uani 1 1 d .
C17 C 0.2117(2) 0.60751(14) 0.59034(14) 0.0302(4) Uani 1 1 d .
C18 C 0.1752(2) 0.68309(15) 0.66817(14) 0.0298(4) Uani 1 1 d .
C19 C 0.1010(2) 0.79510(15) 0.63530(15) 0.0348(4) Uani 1 1 d .
H19 H 0.0727 0.8234 0.5612 0.042 Uiso 1 1 calc R
C20 C 0.0678(3) 0.86590(16) 0.70872(16) 0.0398(5) Uani 1 1 d .
H20 H 0.0168 0.9422 0.6855 0.048 Uiso 1 1 calc R
C21 C 0.1098(2) 0.82423(17) 0.81644(16) 0.0377(5) Uani 1 1 d .
C22 C 0.1820(2) 0.71336(17) 0.85180(15) 0.0377(5) Uani 1 1 d .
H22 H 0.2096 0.6855 0.9261 0.045 Uiso 1 1 calc R
C23 C 0.2137(2) 0.64347(16) 0.77771(15) 0.0348(4) Uani 1 1 d .
H23 H 0.2627 0.5669 0.8017 0.042 Uiso 1 1 calc R
C24 C 0.2344(2) 0.44188(15) 0.50320(15) 0.0330(4) Uani 1 1 d .
C25 C 0.2951(2) 0.53117(15) 0.43623(14) 0.0293(4) Uani 1 1 d .
C26 C 0.3616(2) 0.51618(16) 0.33469(16) 0.0359(4) Uani 1 1 d .
H26 H 0.4090 0.5733 0.2893 0.043 Uiso 1 1 calc R
C27 C 0.3575(3) 0.41718(18) 0.30108(17) 0.0430(5) Uani 1 1 d .
H27 H 0.4011 0.4073 0.2316 0.052 Uiso 1 1 calc R
C28 C 0.2908(3) 0.33167(17) 0.36707(18) 0.0443(5) Uani 1 1 d .
H28 H 0.2870 0.2653 0.3413 0.053 Uiso 1 1 calc R
C29 C 0.2306(2) 0.34209(16) 0.46865(18) 0.0403(5) Uani 1 1 d .
H29 H 0.1875 0.2831 0.5144 0.048 Uiso 1 1 calc R
N1 N -0.3374(3) 0.62637(16) 0.01259(15) 0.0505(5) Uani 1 1 d .
O1 O -0.2699(2) 0.54989(16) -0.03030(14) 0.0668(5) Uani 1 1 d .
O2 O -0.4853(3) 0.66590(19) 0.0038(2) 0.0995(8) Uani 1 1 d .
O3 O -0.01812(16) 0.85253(11) 0.34896(11) 0.0385(3) Uani 1 1 d .
O4 O 0.21294(15) 0.76462(10) 0.27429(9) 0.0296(3) Uani 1 1 d .
S1 S 0.16393(6) 0.47446(4) 0.62685(4) 0.03629(16) Uani 1 1 d .
Cl1 Cl 0.07699(8) 0.91348(5) 0.90931(5) 0.0589(2) Uani 1 1 d .
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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 C1 C2 122.73(18)
C6 C1 N1 118.46(18)
C2 C1 N1 118.80(18)
C1 C2 C3 118.26(19)
C1 C2 H2 120.9
C3 C2 H2 120.9
C2 C3 C4 120.43(18)
C2 C3 H3 119.8
C4 C3 H3 119.8
C3 C4 C5 119.91(17)
C3 C4 C7 117.82(16)
C5 C4 C7 122.17(16)
C6 C5 C4 120.05(18)
C6 C5 H5 120.0
C4 C5 H5 120.0
C1 C6 C5 118.59(18)
C1 C6 H6 120.7
C5 C6 H6 120.7
O3 C7 O4 123.53(16)
O3 C7 C4 124.76(16)
O4 C7 C4 111.70(14)
C15 C8 O4 118.48(15)
C15 C8 C9 127.82(17)
O4 C8 C9 113.70(15)
C10 C9 C14 117.96(18)
C10 C9 C8 120.90(18)
C14 C9 C8 121.14(17)
C9 C10 C11 121.2(2)
C9 C10 H10 119.4
C11 C10 H10 119.4
C12 C11 C10 120.1(2)
C12 C11 H11 120.0
C10 C11 H11 120.0
C13 C12 C11 119.4(2)
C13 C12 H12 120.3
C11 C12 H12 120.3
C12 C13 C14 121.0(2)
C12 C13 H13 119.5
C14 C13 H13 119.5
C13 C14 C9 120.4(2)
C13 C14 H14 119.8
C9 C14 H14 119.8
C8 C15 C16 127.46(16)
C8 C15 H15 116.3
C16 C15 H15 116.3
C17 C16 C25 112.30(16)
C17 C16 C15 121.44(16)
C25 C16 C15 126.05(15)
C16 C17 C18 128.81(16)
C16 C17 S1 112.64(14)
C18 C17 S1 118.55(13)
C19 C18 C23 118.29(17)
C19 C18 C17 121.31(16)
C23 C18 C17 120.40(16)
C20 C19 C18 121.06(18)
C20 C19 H19 119.5
C18 C19 H19 119.5
C21 C20 C19 119.14(18)
C21 C20 H20 120.4
C19 C20 H20 120.4
C22 C21 C20 121.22(18)
C22 C21 Cl1 118.90(15)
C20 C21 Cl1 119.85(16)
C21 C22 C23 119.03(18)
C21 C22 H22 120.5
C23 C22 H22 120.5
C22 C23 C18 121.26(18)
C22 C23 H23 119.4
C18 C23 H23 119.4
C29 C24 C25 121.99(18)
C29 C24 S1 126.40(16)
C25 C24 S1 111.60(14)
C26 C25 C24 118.36(17)
C26 C25 C16 129.94(17)
C24 C25 C16 111.68(16)
C27 C26 C25 119.25(19)
C27 C26 H26 120.4
C25 C26 H26 120.4
C26 C27 C28 121.31(19)
C26 C27 H27 119.3
C28 C27 H27 119.3
C29 C28 C27 120.82(19)
C29 C28 H28 119.6
C27 C28 H28 119.6
C28 C29 C24 118.17(19)
C28 C29 H29 120.9
C24 C29 H29 120.9
O2 N1 O1 123.05(19)
O2 N1 C1 118.0(2)
O1 N1 C1 118.96(19)
C7 O4 C8 115.85(13)
C24 S1 C17 91.78(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.369(3)
C1 C2 1.375(3)
C1 N1 1.477(2)
C2 C3 1.379(3)
C2 H2 0.9500
C3 C4 1.382(3)
C3 H3 0.9500
C4 C5 1.388(2)
C4 C7 1.486(2)
C5 C6 1.379(3)
C5 H5 0.9500
C6 H6 0.9500
C7 O3 1.198(2)
C7 O4 1.355(2)
C8 C15 1.329(3)
C8 O4 1.413(2)
C8 C9 1.473(2)
C9 C10 1.380(3)
C9 C14 1.396(3)
C10 C11 1.388(3)
C10 H10 0.9500
C11 C12 1.377(4)
C11 H11 0.9500
C12 C13 1.364(4)
C12 H12 0.9500
C13 C14 1.384(3)
C13 H13 0.9500
C14 H14 0.9500
C15 C16 1.468(2)
C15 H15 0.9500
C16 C17 1.370(2)
C16 C25 1.449(2)
C17 C18 1.469(3)
C17 S1 1.7369(17)
C18 C19 1.391(3)
C18 C23 1.395(3)
C19 C20 1.381(3)
C19 H19 0.9500
C20 C21 1.383(3)
C20 H20 0.9500
C21 C22 1.379(3)
C21 Cl1 1.7428(19)
C22 C23 1.379(3)
C22 H22 0.9500
C23 H23 0.9500
C24 C29 1.398(3)
C24 C25 1.408(3)
C24 S1 1.7300(19)
C25 C26 1.397(3)
C26 C27 1.383(3)
C26 H26 0.9500
C27 C28 1.393(3)
C27 H27 0.9500
C28 C29 1.369(3)
C28 H28 0.9500
C29 H29 0.9500
N1 O2 1.210(3)
N1 O1 1.212(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139182679
