#------------------------------------------------------------------------------
#$Date: 2016-11-06 04:07:23 +0200 (Sun, 06 Nov 2016) $
#$Revision: 187983 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/39/1543963.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_1543963
loop_
_publ_author_name
'Hagui, Wided'
'Besbes, Néji'
'Srasra, Ezzeddine'
'Roisnel, Thierry'
'Soulé, Jean-François'
'Doucet, Henri'
_publ_section_title
;
 Short Synthesis of Sulfur Analogues of Polyaromatic Hydrocarbons through
 Three Palladium-Catalyzed C-H Bond Arylations.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4182
_journal_page_last               4185
_journal_paper_doi               10.1021/acs.orglett.6b01735
_journal_volume                  18
_journal_year                    2016
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H11 N S'
_chemical_formula_sum            'C18 H11 N S'
_chemical_formula_weight         273.34
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 98.536(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9955(12)
_cell_length_b                   14.118(2)
_cell_length_c                   12.822(2)
_cell_measurement_reflns_used    2515
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.01
_cell_measurement_theta_min      2.89
_cell_measurement_wavelength     0.71073
_cell_volume                     1252.3(3)
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2014)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1050
_diffrn_reflns_av_unetI/netI     0.0984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10490
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.472
_diffrn_reflns_theta_min         2.944
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2856
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.1092
_refine_ls_R_factor_gt           0.0610
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0424P)²+1.6517P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1372
_reflns_number_gt                1900
_reflns_number_total             2856
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b01735_si_001.cif
_cod_data_source_block           WH_P4_26b
_cod_depositor_comments          'Adding full bibliography for 1543963.cif.'
_cod_original_cell_volume        1252.3(4)
_cod_database_code               1543963
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N1 N 0.3809(4) 0.19411(17) 0.5327(2) 0.0285(7) Uani 1 1 d . .
C2 C 0.3378(5) 0.2683(2) 0.5011(2) 0.0199(7) Uani 1 1 d . .
C3 C 0.2781(4) 0.35652(19) 0.4484(2) 0.0163(6) Uani 1 1 d . .
C4 C 0.2295(4) 0.3467(2) 0.3411(2) 0.0183(6) Uani 1 1 d . .
H4 H 0.2368 0.2859 0.3101 0.022 Uiso 1 1 calc R U
C5 C 0.1702(5) 0.4233(2) 0.2775(2) 0.0205(7) Uani 1 1 d . .
H5 H 0.1386 0.4160 0.2032 0.025 Uiso 1 1 calc R U
C6 C 0.1579(4) 0.5102(2) 0.3236(2) 0.0180(6) Uani 1 1 d . .
H6 H 0.1146 0.5632 0.2807 0.022 Uiso 1 1 calc R U
C7 C 0.2077(4) 0.52271(19) 0.4328(2) 0.0143(6) Uani 1 1 d . .
C8 C 0.2693(4) 0.44551(19) 0.5000(2) 0.0130(6) Uani 1 1 d . .
C9 C 0.3179(4) 0.46191(19) 0.6132(2) 0.0138(6) Uani 1 1 d . .
C10 C 0.3775(4) 0.3899(2) 0.6871(2) 0.0185(6) Uani 1 1 d . .
H10 H 0.3867 0.3268 0.6626 0.022 Uiso 1 1 calc R U
C11 C 0.4225(5) 0.4074(2) 0.7925(2) 0.0212(7) Uani 1 1 d . .
H11 H 0.4601 0.3567 0.8399 0.025 Uiso 1 1 calc R U
C12 C 0.4136(5) 0.4988(2) 0.8309(2) 0.0213(7) Uani 1 1 d . .
H12 H 0.4473 0.5111 0.9042 0.026 Uiso 1 1 calc R U
C13 C 0.3561(4) 0.5710(2) 0.7624(2) 0.0192(7) Uani 1 1 d . .
H13 H 0.3505 0.6336 0.7889 0.023 Uiso 1 1 calc R U
C14 C 0.3053(4) 0.55463(19) 0.6544(2) 0.0147(6) Uani 1 1 d . .
C15 C 0.2415(4) 0.63135(19) 0.5845(2) 0.0140(6) Uani 1 1 d . .
C16 C 0.1951(4) 0.61413(19) 0.4789(2) 0.0142(6) Uani 1 1 d . .
C17 C 0.2146(4) 0.72891(18) 0.6105(2) 0.0160(6) Uani 1 1 d . .
H17 H 0.2402 0.7532 0.6803 0.019 Uiso 1 1 calc R U
C18 C 0.1490(4) 0.7826(2) 0.5254(2) 0.0178(6) Uani 1 1 d . .
C19 C 0.1021(5) 0.8859(2) 0.5221(2) 0.0242(7) Uani 1 1 d . .
H19A H 0.1557 0.9152 0.5893 0.036 Uiso 1 1 calc R U
H19B H -0.0385 0.8943 0.5099 0.036 Uiso 1 1 calc R U
H19C H 0.1584 0.9159 0.4648 0.036 Uiso 1 1 calc R U
S1 S 0.11738(11) 0.71646(5) 0.41059(5) 0.0183(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'
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
N1 C2 C3 172.9(3)
C4 C3 C8 122.1(3)
C4 C3 C2 113.0(2)
C8 C3 C2 124.8(2)
C3 C4 C5 121.3(3)
C3 C4 H4 119.3
C5 C4 H4 119.3
C6 C5 C4 118.6(3)
C6 C5 H5 120.7
C4 C5 H5 120.7
C5 C6 C7 121.4(3)
C5 C6 H6 119.3
C7 C6 H6 119.3
C6 C7 C8 121.3(3)
C6 C7 C16 120.4(2)
C8 C7 C16 118.4(2)
C7 C8 C3 115.2(2)
C7 C8 C9 119.2(2)
C3 C8 C9 125.5(2)
C10 C9 C14 116.3(2)
C10 C9 C8 123.8(2)
C14 C9 C8 119.9(2)
C11 C10 C9 122.5(3)
C11 C10 H10 118.8
C9 C10 H10 118.8
C10 C11 C12 120.3(3)
C10 C11 H11 119.9
C12 C11 H11 119.9
C13 C12 C11 119.4(3)
C13 C12 H12 120.3
C11 C12 H12 120.3
C12 C13 C14 121.4(3)
C12 C13 H13 119.3
C14 C13 H13 119.3
C13 C14 C9 120.1(3)
C13 C14 C15 120.3(3)
C9 C14 C15 119.6(2)
C16 C15 C14 119.4(2)
C16 C15 C17 112.3(2)
C14 C15 C17 128.2(2)
C15 C16 C7 123.5(2)
C15 C16 S1 111.3(2)
C7 C16 S1 125.3(2)
C18 C17 C15 113.1(2)
C18 C17 H17 123.5
C15 C17 H17 123.5
C17 C18 C19 128.2(3)
C17 C18 S1 111.7(2)
C19 C18 S1 120.2(2)
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C18 S1 C16 91.65(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.147(4)
C2 C3 1.448(4)
C3 C4 1.375(4)
C3 C8 1.425(4)
C4 C5 1.382(4)
C4 H4 0.9500
C5 C6 1.370(4)
C5 H5 0.9500
C6 C7 1.402(4)
C6 H6 0.9500
C7 C8 1.416(4)
C7 C16 1.428(4)
C8 C9 1.459(4)
C9 C10 1.410(4)
C9 C14 1.419(4)
C10 C11 1.364(4)
C10 H10 0.9500
C11 C12 1.385(4)
C11 H11 0.9500
C12 C13 1.366(4)
C12 H12 0.9500
C13 C14 1.397(4)
C13 H13 0.9500
C14 C15 1.434(4)
C15 C16 1.367(4)
C15 C17 1.436(4)
C16 S1 1.735(3)
C17 C18 1.351(4)
C17 H17 0.9500
C18 C19 1.494(4)
C18 S1 1.730(3)
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
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
C8 C3 C4 C5 0.3(5)
C2 C3 C4 C5 -179.6(3)
C3 C4 C5 C6 -0.9(5)
C4 C5 C6 C7 1.3(5)
C5 C6 C7 C8 -1.2(4)
C5 C6 C7 C16 179.5(3)
C6 C7 C8 C3 0.6(4)
C16 C7 C8 C3 179.9(3)
C6 C7 C8 C9 -179.4(3)
C16 C7 C8 C9 -0.2(4)
C4 C3 C8 C7 -0.2(4)
C2 C3 C8 C7 179.7(3)
C4 C3 C8 C9 179.9(3)
C2 C3 C8 C9 -0.3(5)
C7 C8 C9 C10 178.9(3)
C3 C8 C9 C10 -1.1(5)
C7 C8 C9 C14 -0.8(4)
C3 C8 C9 C14 179.2(3)
C14 C9 C10 C11 -0.5(4)
C8 C9 C10 C11 179.8(3)
C9 C10 C11 C12 -1.0(5)
C10 C11 C12 C13 1.2(5)
C11 C12 C13 C14 0.2(5)
C12 C13 C14 C9 -1.7(5)
C12 C13 C14 C15 178.7(3)
C10 C9 C14 C13 1.8(4)
C8 C9 C14 C13 -178.5(3)
C10 C9 C14 C15 -178.6(3)
C8 C9 C14 C15 1.1(4)
C13 C14 C15 C16 179.1(3)
C9 C14 C15 C16 -0.5(4)
C13 C14 C15 C17 -2.0(5)
C9 C14 C15 C17 178.4(3)
C14 C15 C16 C7 -0.4(4)
C17 C15 C16 C7 -179.5(3)
C14 C15 C16 S1 178.8(2)
C17 C15 C16 S1 -0.3(3)
C6 C7 C16 C15 -179.9(3)
C8 C7 C16 C15 0.8(4)
C6 C7 C16 S1 1.0(4)
C8 C7 C16 S1 -178.3(2)
C16 C15 C17 C18 0.1(4)
C14 C15 C17 C18 -178.8(3)
C15 C17 C18 C19 179.1(3)
C15 C17 C18 S1 0.1(3)
C17 C18 S1 C16 -0.2(2)
C19 C18 S1 C16 -179.3(3)
C15 C16 S1 C18 0.3(2)
C7 C16 S1 C18 179.5(3)
