#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:00:49 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180327 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/41/7154176.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_7154176
loop_
_publ_author_name
'Wang, Yong'
'Li, Ming'
'Wen, Lirong'
'Jing, Peng'
'Su, Xiang'
'Chen, Chao'
_publ_section_title
;
 Exploiting the narrow gap of rearrangement between the substituents in
 the vicinal disubstitution reactions of diaryliodonium salts with
 pyridine N-sulfonamidates.
;
_journal_issue                   3
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              751
_journal_page_last               763
_journal_paper_doi               10.1039/c4ob01744g
_journal_volume                  13
_journal_year                    2015
_chemical_formula_sum            'C19 H19 F6 N2 O2 P S'
_chemical_formula_weight         484.40
_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                 94.34(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.338(3)
_cell_length_b                   10.040(2)
_cell_length_c                   14.189(3)
_cell_measurement_reflns_used    5992
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.33
_cell_volume                     2178.7(8)
_computing_cell_refinement       'Siemens SMART & SAINT'
_computing_data_collection       'Siemens SMART'
_computing_data_reduction        'Siemens XPREP'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_structure_solution    'Siemens SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16984
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.33
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_T_max  .9282
_exptl_absorpt_correction_T_min  .8729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          .48
_exptl_crystal_size_mid          .43
_exptl_crystal_size_min          .26
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4971
_refine_ls_number_restraints     216
_refine_ls_restrained_S_all      1.410
_refine_ls_R_factor_gt           0.0776
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0849P)²+2.0400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2007
_refine_ls_wR_factor_ref         0.2033
_reflns_number_gt                4725
_reflns_number_total             4971
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob01744g2.cif
_cod_data_source_block           p-1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 7154174--7154176.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7154176
#BEGIN Tags that were not found in dictionaries:
_refine_ls_r_factor_ref          0.0811
#END Tags that were not found in dictionaries
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.34666(5) -0.30494(10) 0.92980(7) 0.0455(3) Uani 1 1 d . . .
O1 O 0.37441(16) -0.1864(3) 0.9791(2) 0.0551(7) Uani 1 1 d . . .
O2 O 0.40893(17) -0.4006(3) 0.9033(2) 0.0662(9) Uani 1 1 d . . .
N1 N 0.29317(18) -0.2563(3) 0.82988(19) 0.0415(7) Uani 1 1 d . . .
H1A H 0.3069 -0.2849 0.7758 0.050 Uiso 1 1 d R . .
N2 N 0.32573(18) 0.0233(3) 0.8309(2) 0.0443(7) Uani 1 1 d . . .
C1 C 0.2681(2) -0.3843(3) 0.9936(2) 0.0389(7) Uani 1 1 d . . .
C2 C 0.2466(3) -0.5162(4) 0.9746(3) 0.0491(9) Uani 1 1 d . . .
H2A H 0.2795 -0.5673 0.9335 0.059 Uiso 1 1 calc R . .
C3 C 0.1771(3) -0.5721(4) 1.0162(3) 0.0512(9) Uani 1 1 d . . .
H3A H 0.1628 -0.6628 1.0040 0.061 Uiso 1 1 calc R . .
C4 C 0.1274(2) -0.4991(4) 1.0755(2) 0.0438(8) Uani 1 1 d . . .
C5 C 0.1511(2) -0.3689(4) 1.0953(2) 0.0407(7) Uani 1 1 d . . .
H5A H 0.1190 -0.3190 1.1378 0.049 Uiso 1 1 calc R . .
C6 C 0.2207(2) -0.3090(3) 1.0548(2) 0.0394(7) Uani 1 1 d . . .
H6A H 0.2358 -0.2189 1.0683 0.047 Uiso 1 1 calc R . .
C7 C 0.0491(3) -0.5611(5) 1.1164(3) 0.0607(11) Uani 1 1 d . . .
H7A H 0.0164 -0.4922 1.1476 0.091 Uiso 1 1 calc R . .
H7B H 0.0688 -0.6294 1.1626 0.091 Uiso 1 1 calc R . .
H7C H 0.0114 -0.6019 1.0656 0.091 Uiso 1 1 calc R . .
C8 C 0.22296(19) -0.1640(3) 0.8383(2) 0.0357(7) Uani 1 1 d . . .
C9 C 0.1375(2) -0.2069(4) 0.8456(2) 0.0387(7) Uani 1 1 d . . .
H9A H 0.1243 -0.2993 0.8423 0.046 Uiso 1 1 calc R . .
C10 C 0.0717(2) -0.1158(4) 0.8574(2) 0.0413(8) Uani 1 1 d . . .
H10A H 0.0136 -0.1469 0.8611 0.050 Uiso 1 1 calc R . .
C11 C 0.0884(2) 0.0203(4) 0.8642(2) 0.0421(8) Uani 1 1 d . . .
C12 C 0.1733(2) 0.0632(4) 0.8553(2) 0.0410(7) Uani 1 1 d . . .
H12A H 0.1864 0.1557 0.8582 0.049 Uiso 1 1 calc R . .
C13 C 0.23901(19) -0.0275(3) 0.8421(2) 0.0361(7) Uani 1 1 d . . .
C14 C 0.0171(3) 0.1184(4) 0.8791(3) 0.0567(10) Uani 1 1 d . . .
H14A H -0.0391 0.0821 0.8534 0.085 Uiso 1 1 calc R . .
H14B H 0.0290 0.2020 0.8468 0.085 Uiso 1 1 calc R . .
H14C H 0.0147 0.1353 0.9469 0.085 Uiso 1 1 calc R . .
C15 C 0.3685(3) 0.0875(5) 0.9037(3) 0.0620(12) Uani 1 1 d . . .
H15A H 0.3417 0.1006 0.9612 0.074 Uiso 1 1 calc R . .
C16 C 0.4517(3) 0.1339(6) 0.8933(5) 0.092(2) Uani 1 1 d . . .
H16A H 0.4830 0.1796 0.9438 0.111 Uiso 1 1 calc R . .
C17 C 0.4895(3) 0.1137(7) 0.8094(6) 0.106(2) Uani 1 1 d . . .
H17A H 0.5474 0.1437 0.8025 0.127 Uiso 1 1 calc R . .
C18 C 0.4440(3) 0.0507(6) 0.7362(5) 0.0934(19) Uani 1 1 d . . .
H18A H 0.4694 0.0386 0.6778 0.112 Uiso 1 1 calc R . .
C19 C 0.3607(3) 0.0047(5) 0.7474(3) 0.0625(11) Uani 1 1 d . . .
H19A H 0.3284 -0.0396 0.6970 0.075 Uiso 1 1 calc R . .
F1 F 0.1917(3) -0.9624(6) 0.0855(3) 0.099(3) Uani 0.474(6) 1 d PD A 1
F3 F 0.2882(3) -0.8414(5) 0.2710(3) 0.093(3) Uani 0.474(6) 1 d PDU A 1
F2 F 0.1874(3) -0.9997(5) 0.2405(3) 0.094(3) Uani 0.474(6) 1 d PD A 1
F5 F 0.2926(3) -0.8044(6) 0.1160(4) 0.096(3) Uani 0.474(6) 1 d PD A 1
F4 F 0.1652(3) -0.7943(5) 0.1826(4) 0.106(3) Uani 0.474(6) 1 d PD A 1
F6 F 0.3147(3) -1.0097(5) 0.1739(4) 0.122(4) Uani 0.474(6) 1 d PD A 1
F1' F 0.1593(3) -0.8874(4) 0.1011(3) 0.081(2) Uani 0.526(6) 1 d PD A 2
F3' F 0.3079(3) -0.9197(6) 0.2661(3) 0.115(3) Uani 0.526(6) 1 d PD A 2
F2' F 0.2122(4) -1.0569(4) 0.1898(3) 0.090(2) Uani 0.526(6) 1 d PD A 2
F5' F 0.2549(3) -0.7500(4) 0.1775(4) 0.105(3) Uani 0.526(6) 1 d PDU A 2
F4' F 0.1651(3) -0.8731(5) 0.2585(3) 0.099(3) Uani 0.526(6) 1 d PD A 2
F6' F 0.3020(3) -0.9339(6) 0.1087(3) 0.138(4) Uani 0.526(6) 1 d PDU A 2
P1 P 0.23515(8) -0.90329(10) 0.18024(7) 0.0559(3) Uani 1 1 d 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'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 '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
O2 S1 O1 120.64(18)
O2 S1 N1 105.74(18)
O1 S1 N1 106.45(17)
O2 S1 C1 109.33(19)
O1 S1 C1 108.45(17)
N1 S1 C1 105.12(15)
C8 N1 S1 116.5(2)
C8 N1 H1A 121.8
S1 N1 H1A 121.7
C15 N2 C19 122.5(3)
C15 N2 C13 118.9(3)
C19 N2 C13 118.6(3)
C2 C1 C6 120.7(3)
C2 C1 S1 119.7(3)
C6 C1 S1 119.1(3)
C3 C2 C1 119.1(3)
C3 C2 H2A 120.5
C1 C2 H2A 120.5
C2 C3 C4 121.6(4)
C2 C3 H3A 119.2
C4 C3 H3A 119.2
C5 C4 C3 118.4(3)
C5 C4 C7 121.3(4)
C3 C4 C7 120.4(4)
C4 C5 C6 121.7(3)
C4 C5 H5A 119.1
C6 C5 H5A 119.1
C5 C6 C1 118.4(3)
C5 C6 H6A 120.8
C1 C6 H6A 120.8
C4 C7 H7A 109.5
C4 C7 H7B 109.5
H7A C7 H7B 109.5
C4 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C9 C8 C13 117.8(3)
C9 C8 N1 121.7(3)
C13 C8 N1 120.5(3)
C10 C9 C8 120.4(3)
C10 C9 H9A 119.8
C8 C9 H9A 119.8
C9 C10 C11 121.7(3)
C9 C10 H10A 119.1
C11 C10 H10A 119.1
C12 C11 C10 117.9(3)
C12 C11 C14 120.6(3)
C10 C11 C14 121.5(3)
C13 C12 C11 120.5(3)
C13 C12 H12A 119.7
C11 C12 H12A 119.7
C12 C13 C8 121.7(3)
C12 C13 N2 118.0(3)
C8 C13 N2 120.3(3)
C11 C14 H14A 109.5
C11 C14 H14B 109.5
H14A C14 H14B 109.5
C11 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
N2 C15 C16 118.8(5)
N2 C15 H15A 120.6
C16 C15 H15A 120.6
C15 C16 C17 119.8(5)
C15 C16 H16A 120.1
C17 C16 H16A 120.1
C18 C17 C16 120.1(5)
C18 C17 H17A 119.9
C16 C17 H17A 119.9
C17 C18 C19 119.6(6)
C17 C18 H18A 120.2
C19 C18 H18A 120.2
N2 C19 C18 119.3(5)
N2 C19 H19A 120.4
C18 C19 H19A 120.4
F2 P1 F6' 128.6(3)
F2 P1 F4 94.24(17)
F6' P1 F4 131.6(2)
F2 P1 F1' 96.0(3)
F6' P1 F1' 92.49(15)
F4 P1 F1' 57.3(2)
F2 P1 F5' 137.9(3)
F6' P1 F5' 92.29(16)
F4 P1 F5' 55.8(3)
F1' P1 F5' 90.95(15)
F2 P1 F1 92.82(17)
F6' P1 F1 67.5(3)
F4 P1 F1 92.07(16)
F1' P1 F1 34.8(2)
F5' P1 F1 114.8(2)
F2 P1 F2' 38.1(2)
F6' P1 F2' 91.48(16)
F4 P1 F2' 122.0(2)
F1' P1 F2' 90.15(15)
F5' P1 F2' 176.0(2)
F1 P1 F2' 67.9(2)
F2 P1 F3 91.85(16)
F6' P1 F3 106.7(3)
F4 P1 F3 91.12(17)
F1' P1 F3 147.8(2)
F5' P1 F3 63.3(2)
F1 P1 F3 174.1(2)
F2' P1 F3 114.3(2)
F2 P1 F3' 81.0(3)
F6' P1 F3' 91.21(16)
F4 P1 F3' 120.4(3)
F1' P1 F3' 176.2(2)
F5' P1 F3' 89.70(15)
F1 P1 F3' 147.2(3)
F2' P1 F3' 88.95(14)
F3 P1 F3' 30.7(2)
F2 P1 F6 90.49(16)
F6' P1 F6 44.7(3)
F4 P1 F6 175.2(2)
F1' P1 F6 123.2(2)
F5' P1 F6 119.7(3)
F1 P1 F6 88.63(16)
F2' P1 F6 62.6(3)
F3 P1 F6 87.78(15)
F3' P1 F6 59.4(3)
F2 P1 F4' 50.5(2)
F6' P1 F4' 178.6(2)
F4 P1 F4' 49.8(2)
F1' P1 F4' 88.70(15)
F5' P1 F4' 88.46(15)
F1 P1 F4' 113.2(3)
F2' P1 F4' 87.75(15)
F3 P1 F4' 72.6(3)
F3' P1 F4' 87.60(14)
F6 P1 F4' 133.9(2)
F2 P1 F5 176.4(2)
F6' P1 F5 48.7(2)
F4 P1 F5 89.22(15)
F1' P1 F5 86.6(3)
F5' P1 F5 44.2(2)
F1 P1 F5 87.97(15)
F2' P1 F5 139.7(2)
F3 P1 F5 87.15(16)
F3' P1 F5 96.4(3)
F6 P1 F5 86.03(15)
F4' P1 F5 132.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.425(3)
S1 O1 1.429(3)
S1 N1 1.657(3)
S1 C1 1.753(3)
N1 C8 1.432(4)
N1 H1A 0.8602
N2 C15 1.346(5)
N2 C19 1.349(5)
N2 C13 1.444(4)
C1 C2 1.386(5)
C1 C6 1.395(5)
C2 C3 1.377(5)
C2 H2A 0.9500
C3 C4 1.387(5)
C3 H3A 0.9500
C4 C5 1.380(5)
C4 C7 1.506(5)
C5 C6 1.387(5)
C5 H5A 0.9500
C6 H6A 0.9500
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 C9 1.390(4)
C8 C13 1.393(5)
C9 C10 1.382(5)
C9 H9A 0.9500
C10 C11 1.393(5)
C10 H10A 0.9500
C11 C12 1.386(5)
C11 C14 1.499(5)
C12 C13 1.381(5)
C12 H12A 0.9500
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 C16 1.378(6)
C15 H15A 0.9500
C16 C17 1.378(10)
C16 H16A 0.9500
C17 C18 1.363(10)
C17 H17A 0.9500
C18 C19 1.378(6)
C18 H18A 0.9500
C19 H19A 0.9500
F1 P1 1.571(4)
F3 P1 1.596(4)
F2 P1 1.517(4)
F5 P1 1.648(4)
F4 P1 1.535(4)
F6 P1 1.630(4)
F1' P1 1.563(4)
F3' P1 1.596(4)
F2' P1 1.590(4)
F5' P1 1.569(4)
F4' P1 1.630(4)
F6' P1 1.527(4)
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
O2 S1 N1 C8 176.8(3)
O1 S1 N1 C8 -53.7(3)
C1 S1 N1 C8 61.2(3)
O2 S1 C1 C2 -30.6(3)
O1 S1 C1 C2 -163.9(3)
N1 S1 C1 C2 82.5(3)
O2 S1 C1 C6 157.0(3)
O1 S1 C1 C6 23.7(3)
N1 S1 C1 C6 -89.9(3)
C6 C1 C2 C3 0.7(6)
S1 C1 C2 C3 -171.6(3)
C1 C2 C3 C4 0.9(6)
C2 C3 C4 C5 -2.5(6)
C2 C3 C4 C7 177.2(4)
C3 C4 C5 C6 2.5(5)
C7 C4 C5 C6 -177.1(3)
C4 C5 C6 C1 -1.0(5)
C2 C1 C6 C5 -0.6(5)
S1 C1 C6 C5 171.7(2)
S1 N1 C8 C9 -91.5(3)
S1 N1 C8 C13 86.8(3)
C13 C8 C9 C10 -0.9(5)
N1 C8 C9 C10 177.4(3)
C8 C9 C10 C11 -1.1(5)
C9 C10 C11 C12 2.3(5)
C9 C10 C11 C14 -178.7(3)
C10 C11 C12 C13 -1.4(5)
C14 C11 C12 C13 179.6(3)
C11 C12 C13 C8 -0.7(5)
C11 C12 C13 N2 178.5(3)
C9 C8 C13 C12 1.8(5)
N1 C8 C13 C12 -176.5(3)
C9 C8 C13 N2 -177.3(3)
N1 C8 C13 N2 4.4(4)
C15 N2 C13 C12 64.8(5)
C19 N2 C13 C12 -115.0(4)
C15 N2 C13 C8 -116.0(4)
C19 N2 C13 C8 64.2(5)
C19 N2 C15 C16 -1.3(7)
C13 N2 C15 C16 179.0(4)
N2 C15 C16 C17 -0.1(9)
C15 C16 C17 C18 1.5(10)
C16 C17 C18 C19 -1.5(10)
C15 N2 C19 C18 1.2(7)
C13 N2 C19 C18 -179.0(5)
C17 C18 C19 N2 0.2(9)
