#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/17/4031722.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_4031722
loop_
_publ_author_name
'Kumar, Sonu'
'Cruz-Hernández, Carlos'
'Pal, Shilpi'
'Saunthwal, Rakesh K.'
'Patel, Monika'
'Tiwari, Rakesh K.'
'Juaristi, Eusebio'
'Verma, Akhilesh K.'
_publ_section_title
;
 Tandem Approach to Benzothieno- and Benzofuropyridines from o-Alkynyl
 Aldehydes via Silver-Catalyzed 6-endo-dig Ring Closure.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.5b01647
_journal_year                    2015
_chemical_formula_moiety         'C18 H13 N S'
_chemical_formula_sum            'C18 H13 N S'
_chemical_formula_weight         275.35
_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                 108.70(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.661(3)
_cell_length_b                   8.1860(12)
_cell_length_c                   12.112(2)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.95
_cell_volume                     1376.9(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur Sapphire3'
_diffrn_measurement_method       'ω 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  0.0784
_diffrn_reflns_av_sigmaI/netI    0.0731
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9741
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.89
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.9589
_exptl_absorpt_correction_T_min  0.9485
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2426
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0669
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0831P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1522
_refine_ls_wR_factor_ref         0.1757
_reflns_number_gt                1583
_reflns_number_total             2426
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01647_si_001.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        1376.8(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4031722
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 0.4088(2) 0.4056(3) 0.3401(3) 0.0457(8) Uani 1 1 d .
C2 C 0.3107(2) 0.3997(4) 0.3210(3) 0.0569(10) Uani 1 1 d .
H2 H 0.2691 0.4668 0.2653 0.068 Uiso 1 1 calc R
C3 C 0.2755(3) 0.2941(4) 0.3849(3) 0.0629(10) Uani 1 1 d .
H3 H 0.2095 0.2889 0.3720 0.075 Uiso 1 1 calc R
C4 C 0.3375(2) 0.1941(4) 0.4693(3) 0.0578(10) Uani 1 1 d .
H4 H 0.3126 0.1233 0.5124 0.069 Uiso 1 1 calc R
C5 C 0.4358(2) 0.1995(4) 0.4894(3) 0.0501(9) Uani 1 1 d .
H5 H 0.4770 0.1325 0.5455 0.060 Uiso 1 1 calc R
C6 C 0.4727(2) 0.3069(3) 0.4242(3) 0.0421(8) Uani 1 1 d .
C7 C 0.5723(2) 0.3339(3) 0.4306(3) 0.0408(8) Uani 1 1 d .
C8 C 0.6567(2) 0.2624(3) 0.4999(3) 0.0428(8) Uani 1 1 d .
H8 H 0.6550 0.1851 0.5555 0.051 Uiso 1 1 calc R
C9 C 0.7438(2) 0.3060(3) 0.4867(3) 0.0444(8) Uani 1 1 d .
C10 C 0.6684(3) 0.4871(4) 0.3386(3) 0.0538(9) Uani 1 1 d .
H10 H 0.6720 0.5629 0.2830 0.065 Uiso 1 1 calc R
C11 C 0.5784(2) 0.4506(3) 0.3489(3) 0.0437(8) Uani 1 1 d .
C12 C 0.8376(2) 0.2333(3) 0.5582(3) 0.0463(8) Uani 1 1 d .
C13 C 0.8467(3) 0.1442(4) 0.6590(3) 0.0575(10) Uani 1 1 d .
H13 H 0.7938 0.1326 0.6849 0.069 Uiso 1 1 calc R
C14 C 0.9333(3) 0.0729(4) 0.7209(4) 0.0646(11) Uani 1 1 d .
H14 H 0.9379 0.0116 0.7871 0.078 Uiso 1 1 calc R
C15 C 1.0133(3) 0.0921(4) 0.6851(4) 0.0630(10) Uani 1 1 d .
H15 H 1.0713 0.0430 0.7271 0.076 Uiso 1 1 calc R
C16 C 1.0074(2) 0.1848(4) 0.5866(3) 0.0547(9) Uani 1 1 d .
C17 C 0.9190(2) 0.2536(4) 0.5239(3) 0.0511(9) Uani 1 1 d .
H17 H 0.9142 0.3147 0.4575 0.061 Uiso 1 1 calc R
C18 C 1.0935(2) 0.2114(5) 0.5463(4) 0.0741(12) Uani 1 1 d .
H18A H 1.0752 0.2777 0.4773 0.111 Uiso 1 1 calc R
H18B H 1.1168 0.1079 0.5294 0.111 Uiso 1 1 calc R
H18C H 1.1434 0.2656 0.6065 0.111 Uiso 1 1 calc R
N1 N 0.7490(2) 0.4170(3) 0.4056(3) 0.0550(8) Uani 1 1 d .
S1 S 0.46746(7) 0.53175(10) 0.26793(9) 0.0573(4) 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'
S S 0.1246 0.1234 '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 C1 C6 121.3(3)
C2 C1 S1 126.1(3)
C6 C1 S1 112.5(2)
C3 C2 C1 119.3(3)
C3 C2 H2 120.4
C1 C2 H2 120.4
C2 C3 C4 120.7(3)
C2 C3 H3 119.7
C4 C3 H3 119.7
C5 C4 C3 120.5(3)
C5 C4 H4 119.7
C3 C4 H4 119.7
C4 C5 C6 119.3(3)
C4 C5 H5 120.3
C6 C5 H5 120.3
C1 C6 C5 118.8(3)
C1 C6 C7 112.2(3)
C5 C6 C7 128.9(3)
C8 C7 C11 118.1(3)
C8 C7 C6 131.0(3)
C11 C7 C6 110.9(3)
C7 C8 C9 120.0(3)
C7 C8 H8 120.0
C9 C8 H8 120.0
N1 C9 C8 121.7(3)
N1 C9 C12 115.5(3)
C8 C9 C12 122.8(3)
N1 C10 C11 122.3(3)
N1 C10 H10 118.9
C11 C10 H10 118.9
C10 C11 C7 119.1(3)
C10 C11 S1 127.4(3)
C7 C11 S1 113.5(2)
C13 C12 C17 118.4(3)
C13 C12 C9 121.9(3)
C17 C12 C9 119.8(3)
C14 C13 C12 120.7(3)
C14 C13 H13 119.7
C12 C13 H13 119.7
C13 C14 C15 120.4(4)
C13 C14 H14 119.8
C15 C14 H14 119.8
C14 C15 C16 120.3(3)
C14 C15 H15 119.9
C16 C15 H15 119.9
C15 C16 C17 118.6(3)
C15 C16 C18 121.8(3)
C17 C16 C18 119.6(3)
C12 C17 C16 121.6(3)
C12 C17 H17 119.2
C16 C17 H17 119.2
C16 C18 H18A 109.5
C16 C18 H18B 109.5
H18A C18 H18B 109.5
C16 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C10 N1 C9 118.9(3)
C11 S1 C1 90.78(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.383(4)
C1 C6 1.399(4)
C1 S1 1.747(3)
C2 C3 1.366(5)
C2 H2 0.9300
C3 C4 1.395(5)
C3 H3 0.9300
C4 C5 1.383(4)
C4 H4 0.9300
C5 C6 1.401(4)
C5 H5 0.9300
C6 C7 1.453(4)
C7 C8 1.383(4)
C7 C11 1.399(4)
C8 C9 1.383(4)
C8 H8 0.9300
C9 N1 1.358(4)
C9 C12 1.495(4)
C10 N1 1.331(4)
C10 C11 1.396(4)
C10 H10 0.9300
C11 S1 1.740(3)
C12 C13 1.391(4)
C12 C17 1.393(4)
C13 C14 1.380(5)
C13 H13 0.9300
C14 C15 1.384(5)
C14 H14 0.9300
C15 C16 1.393(5)
C15 H15 0.9300
C16 C17 1.395(4)
C16 C18 1.508(4)
C17 H17 0.9300
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
C6 C1 C2 C3 -0.6(5)
S1 C1 C2 C3 -179.9(3)
C1 C2 C3 C4 0.6(5)
C2 C3 C4 C5 -0.3(5)
C3 C4 C5 C6 0.2(5)
C2 C1 C6 C5 0.4(5)
S1 C1 C6 C5 179.8(2)
C2 C1 C6 C7 -179.4(3)
S1 C1 C6 C7 0.0(3)
C4 C5 C6 C1 -0.2(5)
C4 C5 C6 C7 179.6(3)
C1 C6 C7 C8 -179.5(3)
C5 C6 C7 C8 0.7(5)
C1 C6 C7 C11 -1.0(3)
C5 C6 C7 C11 179.2(3)
C11 C7 C8 C9 -0.6(4)
C6 C7 C8 C9 177.8(3)
C7 C8 C9 N1 -0.8(5)
C7 C8 C9 C12 -179.7(3)
N1 C10 C11 C7 -1.5(5)
N1 C10 C11 S1 -179.9(2)
C8 C7 C11 C10 1.6(4)
C6 C7 C11 C10 -177.1(3)
C8 C7 C11 S1 -179.7(2)
C6 C7 C11 S1 1.6(3)
N1 C9 C12 C13 166.8(3)
C8 C9 C12 C13 -14.2(5)
N1 C9 C12 C17 -13.5(4)
C8 C9 C12 C17 165.6(3)
C17 C12 C13 C14 -2.3(5)
C9 C12 C13 C14 177.4(3)
C12 C13 C14 C15 1.5(5)
C13 C14 C15 C16 0.5(6)
C14 C15 C16 C17 -1.6(5)
C14 C15 C16 C18 178.7(3)
C13 C12 C17 C16 1.2(5)
C9 C12 C17 C16 -178.5(3)
C15 C16 C17 C12 0.7(5)
C18 C16 C17 C12 -179.6(3)
C11 C10 N1 C9 0.1(5)
C8 C9 N1 C10 1.0(5)
C12 C9 N1 C10 -180.0(3)
C10 C11 S1 C1 177.2(3)
C7 C11 S1 C1 -1.4(2)
C2 C1 S1 C11 -179.9(3)
C6 C1 S1 C11 0.8(2)
