#------------------------------------------------------------------------------
#$Date: 2016-03-21 05:35:49 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178486 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/07/4030752.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_4030752
loop_
_publ_author_name
'Parella, Ramarao'
'Babu, Srinivasarao Arulananda'
_publ_section_title
;
 Regio- and Stereoselective Pd-Catalyzed Direct Arylation of Unactivated
 sp(3) C(3)-H Bonds of Tetrahydrofuran and 1,4-Benzodioxane Systems.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2339
_journal_page_last               2355
_journal_paper_doi               10.1021/acs.joc.5b00025
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C22 H16 N2 O3 S'
_chemical_formula_sum            'C22 H16 N2 O3 S'
_chemical_formula_weight         388.43
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-10-01T20:34:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 99.083(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.196(2)
_cell_length_b                   8.3712(14)
_cell_length_c                   16.808(3)
_cell_measurement_reflns_used    5013
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.56
_cell_measurement_theta_min      2.45
_cell_volume                     1833.4(5)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21545
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         1.828
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0679 before and 0.0582 after correction.
        The Ratio of minimum to maximum transmission is 0.9222.
        The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       block
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.17
_refine_diff_density_min         -0.93
_refine_diff_density_rms         0.09
_refine_ls_extinction_coef       0.008(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3353
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0813
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1814P)²+1.5432P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2587
_refine_ls_wR_factor_ref         0.2827
_reflns_number_gt                2546
_reflns_number_total             3353
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo5b00025_si_004.cif
_cod_data_source_block           sci225_pr2036b2_0m
_cod_original_cell_volume        1833.5(5)
_cod_database_code               4030752
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_calc_flag
H1A H 0.994(3) 0.917(5) 0.389(3) 0.052(12) Uiso 1 d
C1 C 1.2449(3) 1.2498(5) 0.1388(3) 0.0603(11) Uani 1 d
H1 H 1.2886 1.2966 0.1072 0.072 Uiso 1 calc
C2 C 1.1437(3) 1.2201(5) 0.1074(3) 0.0544(10) Uani 1 d
H2 H 1.1193 1.2458 0.054 0.065 Uiso 1 calc
C3 C 1.0781(3) 1.1520(4) 0.1548(2) 0.0450(9) Uani 1 d
C4 C 0.9237(3) 1.0167(4) 0.1654(2) 0.0421(8) Uani 1 d
H4 H 0.85 1.0308 0.1471 0.05 Uiso 1 calc
C5 C 0.9465(3) 1.0639(4) 0.2537(2) 0.0449(9) Uani 1 d
H5 H 0.9298 1.1775 0.2574 0.054 Uiso 1 calc
C6 C 0.8816(3) 0.9715(5) 0.3052(2) 0.0455(9) Uani 1 d
C7 C 0.8923(3) 0.8201(4) 0.4322(2) 0.0442(9) Uani 1 d
C8 C 0.9653(3) 0.7541(4) 0.4948(2) 0.0433(8) Uani 1 d
C9 C 0.9311(3) 0.6616(5) 0.5565(2) 0.0511(10) Uani 1 d
C10 C 1.0079(4) 0.5961(5) 0.6151(2) 0.0611(11) Uani 1 d
H10 H 0.9893 0.533 0.656 0.073 Uiso 1 calc
C11 C 1.1062(4) 0.6234(6) 0.6127(3) 0.0651(12) Uani 1 d
H11 H 1.1567 0.5816 0.652 0.078 Uiso 1 calc
C12 C 1.1155(3) 1.1139(4) 0.2349(2) 0.0439(8) Uani 1 d
C13 C 1.2164(3) 1.1421(5) 0.2658(3) 0.0541(10) Uani 1 d
H13 H 1.2415 1.1159 0.319 0.065 Uiso 1 calc
C14 C 1.2806(3) 1.2093(5) 0.2179(3) 0.0616(11) Uani 1 d
H14 H 1.349 1.2277 0.2392 0.074 Uiso 1 calc
C15 C 0.7888(3) 0.7941(5) 0.4326(3) 0.0556(10) Uani 1 d
H15 H 0.7406 0.8366 0.3918 0.067 Uiso 1 calc
C16 C 0.7564(3) 0.7047(6) 0.4938(3) 0.0647(12) Uani 1 d
H16 H 0.6866 0.6883 0.4931 0.078 Uiso 1 calc
C17 C 0.8247(3) 0.6408(6) 0.5545(3) 0.0608(11) Uani 1 d
H17 H 0.801 0.5829 0.5951 0.073 Uiso 1 calc
C18 C 1.1329(3) 0.7162(6) 0.5499(3) 0.0614(11) Uani 1 d
H18 H 1.2023 0.7335 0.5489 0.074 Uiso 1 calc
C19 C 0.9508(3) 0.8466(4) 0.1487(2) 0.0435(9) Uani 1 d
C20 C 0.9586(4) 0.5591(5) 0.1393(3) 0.0753(14) Uani 1 d
H20 H 0.9493 0.4494 0.1433 0.09 Uiso 1 calc
C21 C 1.0257(4) 0.6229(7) 0.0973(3) 0.0774(15) Uani 1 d
H21 H 1.0668 0.5599 0.0699 0.093 Uiso 1 calc
C22 C 1.0316(2) 0.7978(3) 0.09645(17) 0.0288(7) Uani 1 d
H22 H 1.0735 0.8629 0.0708 0.035 Uiso 1 calc
N1 N 0.9325(2) 0.9077(4) 0.37318(19) 0.0464(8) Uani 1 d
N2 N 1.0666(2) 0.7808(4) 0.49213(19) 0.0502(8) Uani 1 d
O1 O 0.97751(19) 1.1248(3) 0.12067(16) 0.0506(7) Uani 1 d
O2 O 1.05317(18) 1.0449(3) 0.28406(15) 0.0484(7) Uani 1 d
O3 O 0.7898(2) 0.9638(4) 0.28262(17) 0.0652(9) Uani 1 d
S1 S 0.89366(12) 0.68934(16) 0.18352(10) 0.0863(6) Uani 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 0 '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 0.006 '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 H1 120.4
C2 C1 C14 119.2(4)
C14 C1 H1 120.4
C1 C2 H2 119.7
C1 C2 C3 120.6(4)
C3 C2 H2 119.7
C2 C3 C12 119.3(4)
O1 C3 C2 118.4(3)
O1 C3 C12 122.3(3)
C5 C4 H4 108
C19 C4 H4 108
C19 C4 C5 114.3(3)
O1 C4 H4 108
O1 C4 C5 108.0(3)
O1 C4 C19 110.3(3)
C4 C5 H5 107.7
C4 C5 C6 112.4(3)
C6 C5 H5 107.7
O2 C5 C4 110.6(3)
O2 C5 H5 107.7
O2 C5 C6 110.5(3)
N1 C6 C5 115.9(3)
O3 C6 C5 118.2(3)
O3 C6 N1 125.9(4)
C15 C7 C8 119.2(4)
C15 C7 N1 124.7(4)
N1 C7 C8 116.1(3)
C7 C8 C9 119.7(3)
N2 C8 C7 117.7(3)
N2 C8 C9 122.6(4)
C10 C9 C8 116.5(4)
C10 C9 C17 124.9(4)
C17 C9 C8 118.6(4)
C9 C10 H10 119.6
C11 C10 C9 120.8(4)
C11 C10 H10 119.6
C10 C11 H11 120.6
C10 C11 C18 118.9(4)
C18 C11 H11 120.6
C13 C12 C3 120.0(4)
C13 C12 O2 118.6(3)
O2 C12 C3 121.3(3)
C12 C13 H13 120
C12 C13 C14 119.9(4)
C14 C13 H13 120
C1 C14 H14 119.5
C13 C14 C1 121.0(4)
C13 C14 H14 119.5
C7 C15 H15 119.8
C7 C15 C16 120.5(4)
C16 C15 H15 119.8
C15 C16 H16 119.3
C17 C16 C15 121.4(4)
C17 C16 H16 119.3
C9 C17 H17 119.7
C16 C17 C9 120.5(4)
C16 C17 H17 119.7
C11 C18 H18 117.7
N2 C18 C11 124.5(4)
N2 C18 H18 117.7
C4 C19 C22 124.3(3)
C4 C19 S1 123.2(3)
C22 C19 S1 112.5(2)
C21 C20 H20 122.8
C21 C20 S1 114.5(4)
S1 C20 H20 122.8
C20 C21 H21 121.7
C20 C21 C22 116.6(4)
C22 C21 H21 121.7
C19 C22 H22 128.8
C21 C22 C19 102.5(3)
C21 C22 H22 128.8
C6 N1 H1A 125(3)
C6 N1 C7 128.1(3)
C7 N1 H1A 107(3)
C18 N2 C8 116.7(4)
C3 O1 C4 114.2(3)
C12 O2 C5 112.7(3)
C20 S1 C19 93.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 H1 0.93
C1 C2 1.379(6)
C1 C14 1.381(7)
C2 H2 0.93
C2 C3 1.389(6)
C3 C12 1.396(5)
C3 O1 1.379(4)
C4 H4 0.98
C4 C5 1.518(5)
C4 C19 1.505(5)
C4 O1 1.435(4)
C5 H5 0.98
C5 C6 1.522(5)
C5 O2 1.429(4)
C6 N1 1.340(5)
C6 O3 1.213(4)
C7 C8 1.422(5)
C7 C15 1.384(5)
C7 N1 1.403(5)
C8 C9 1.422(5)
C8 N2 1.363(5)
C9 C10 1.407(6)
C9 C17 1.411(6)
C10 H10 0.93
C10 C11 1.324(6)
C11 H11 0.93
C11 C18 1.399(7)
C12 C13 1.372(5)
C12 O2 1.381(4)
C13 H13 0.93
C13 C14 1.377(6)
C14 H14 0.93
C15 H15 0.93
C15 C16 1.392(6)
C16 H16 0.93
C16 C17 1.360(7)
C17 H17 0.93
C18 H18 0.93
C18 N2 1.316(5)
C19 C22 1.540(4)
C19 S1 1.668(4)
C20 H20 0.93
C20 C21 1.329(8)
C20 S1 1.636(5)
C21 H21 0.93
C21 C22 1.466(6)
C22 H22 0.93
N1 H1A 0.82(4)
