#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/77/4117764.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_4117764
loop_
_publ_author_name
'Yanchuan Zhao'
'Bing Gao'
'Jinbo Hu'
_publ_section_title
;
 From Olefination to Alkylation: In-Situ Halogenation of Julia-Kocienski
 Intermediates Leading to Formal Nucleophilic Iodo- and
 Bromodifluoromethylation of Carbonyl Compounds
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5790
_journal_page_last               5793
_journal_paper_doi               10.1021/ja301601b
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C17 H13 N O3 S'
_chemical_formula_weight         311.34
_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                 91.641(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.9468(8)
_cell_length_b                   6.0282(4)
_cell_length_c                   15.2252(8)
_cell_measurement_reflns_used    3132
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      65.57
_cell_measurement_theta_min      5.81
_cell_volume                     1463.01(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13477
_diffrn_reflns_theta_full        65.00
_diffrn_reflns_theta_max         65.00
_diffrn_reflns_theta_min         5.81
_exptl_absorpt_coefficient_mu    2.076
_exptl_absorpt_correction_T_max  0.9795
_exptl_absorpt_correction_T_min  0.6249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.735
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2414
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0821
_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)+(0.1122P)²+3.0074P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2135
_refine_ls_wR_factor_ref         0.2361
_reflns_number_gt                1835
_reflns_number_total             2414
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja301601b_si_004.cif
_cod_data_source_block           cu_dm11521_0ma
_cod_database_code               4117764
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
S1 S 0.85399(8) 0.2756(3) 0.10634(9) 0.0688(5) Uani 1 1 d .
O1 O 0.8519(2) 0.1082(9) 0.1679(3) 0.0905(14) Uani 1 1 d .
O2 O 0.9172(3) 0.4424(9) 0.1142(4) 0.115(2) Uani 1 1 d .
O3 O 0.7640(2) -0.0858(6) 0.0244(3) 0.0834(13) Uani 1 1 d .
N1 N 0.8735(2) 0.1501(7) 0.0072(2) 0.0522(10) Uani 1 1 d .
C1 C 0.8247(3) -0.0320(9) -0.0195(3) 0.0600(12) Uani 1 1 d .
C2 C 0.8502(4) -0.1424(12) -0.0963(4) 0.0840(18) Uani 1 1 d .
H2 H 0.8230 -0.2764 -0.1135 0.101 Uiso 1 1 calc R
C3 C 0.9122(4) -0.0623(13) -0.1459(4) 0.087(2) Uani 1 1 d .
H3 H 0.9269 -0.1378 -0.1980 0.104 Uiso 1 1 calc R
C4 C 0.9542(4) 0.1282(12) -0.1213(4) 0.090(2) Uani 1 1 d .
H4 H 0.9960 0.1873 -0.1578 0.109 Uiso 1 1 calc R
C5 C 0.9358(4) 0.2332(10) -0.0441(4) 0.0833(19) Uani 1 1 d .
H5 H 0.9660 0.3622 -0.0262 0.100 Uiso 1 1 calc R
C6 C 0.7584(3) 0.4066(10) 0.0917(3) 0.0626(13) Uani 1 1 d .
H6 H 0.7562 0.5476 0.0639 0.075 Uiso 1 1 calc R
C7 C 0.6888(3) 0.3165(9) 0.1181(3) 0.0548(12) Uani 1 1 d .
H7 H 0.6924 0.1705 0.1415 0.066 Uiso 1 1 calc R
C8 C 0.6057(3) 0.4218(7) 0.1146(2) 0.0430(10) Uani 1 1 d .
C9 C 0.5412(3) 0.3126(7) 0.1547(2) 0.0413(10) Uani 1 1 d .
H9 H 0.5509 0.1712 0.1806 0.050 Uiso 1 1 calc R
C10 C 0.4593(3) 0.4116(7) 0.1575(2) 0.0409(10) Uani 1 1 d .
C11 C 0.3935(3) 0.3064(8) 0.2008(3) 0.0473(10) Uani 1 1 d .
H11 H 0.4022 0.1648 0.2269 0.057 Uiso 1 1 calc R
C12 C 0.3173(3) 0.4070(9) 0.2053(3) 0.0586(12) Uani 1 1 d .
H12 H 0.2735 0.3356 0.2354 0.070 Uiso 1 1 calc R
C13 C 0.3025(3) 0.6152(9) 0.1661(3) 0.0572(12) Uani 1 1 d .
H13 H 0.2488 0.6826 0.1693 0.069 Uiso 1 1 calc R
C14 C 0.3647(3) 0.7194(8) 0.1237(3) 0.0573(13) Uani 1 1 d .
H14 H 0.3539 0.8590 0.0968 0.069 Uiso 1 1 calc R
C15 C 0.4471(3) 0.6225(7) 0.1187(2) 0.0435(10) Uani 1 1 d .
C16 C 0.5137(3) 0.7269(7) 0.0777(3) 0.0506(11) Uani 1 1 d .
H16 H 0.5049 0.8667 0.0502 0.061 Uiso 1 1 calc R
C17 C 0.5910(3) 0.6317(8) 0.0765(3) 0.0514(11) Uani 1 1 d .
H17 H 0.6357 0.7078 0.0496 0.062 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O1 S1 O2 119.3(3)
O1 S1 N1 106.4(2)
O2 S1 N1 103.8(2)
O1 S1 C6 112.6(2)
O2 S1 C6 108.0(3)
N1 S1 C6 105.6(2)
C5 N1 C1 121.7(5)
C5 N1 S1 119.2(4)
C1 N1 S1 119.1(3)
O3 C1 N1 119.1(5)
O3 C1 C2 124.9(5)
N1 C1 C2 116.0(5)
C3 C2 C1 121.7(6)
C3 C2 H2 119.1
C1 C2 H2 119.1
C2 C3 C4 120.3(6)
C2 C3 H3 119.8
C4 C3 H3 119.8
C5 C4 C3 120.2(5)
C5 C4 H4 119.9
C3 C4 H4 119.9
C4 C5 N1 119.5(6)
C4 C5 H5 120.2
N1 C5 H5 120.2
C7 C6 S1 121.6(5)
C7 C6 H6 119.2
S1 C6 H6 119.2
C6 C7 C8 125.5(5)
C6 C7 H7 117.2
C8 C7 H7 117.2
C9 C8 C17 119.6(4)
C9 C8 C7 117.5(4)
C17 C8 C7 122.9(4)
C8 C9 C10 120.4(4)
C8 C9 H9 119.8
C10 C9 H9 119.8
C11 C10 C15 120.5(4)
C11 C10 C9 121.2(4)
C15 C10 C9 118.3(4)
C12 C11 C10 120.1(4)
C12 C11 H11 119.9
C10 C11 H11 119.9
C11 C12 C13 121.0(5)
C11 C12 H12 119.5
C13 C12 H12 119.5
C14 C13 C12 120.0(5)
C14 C13 H13 120.0
C12 C13 H13 120.0
C13 C14 C15 121.3(4)
C13 C14 H14 119.4
C15 C14 H14 119.4
C16 C15 C10 119.7(4)
C16 C15 C14 123.1(4)
C10 C15 C14 117.2(4)
C17 C16 C15 121.1(4)
C17 C16 H16 119.4
C15 C16 H16 119.4
C16 C17 C8 120.9(4)
C16 C17 H17 119.6
C8 C17 H17 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.379(5)
S1 O2 1.427(5)
S1 N1 1.725(4)
S1 C6 1.725(5)
O3 C1 1.236(6)
N1 C5 1.376(6)
N1 C1 1.399(6)
C1 C2 1.415(8)
C2 C3 1.350(9)
C2 H2 0.9500
C3 C4 1.375(10)
C3 H3 0.9500
C4 C5 1.374(9)
C4 H4 0.9500
C5 H5 0.9500
C6 C7 1.309(7)
C6 H6 0.9500
C7 C8 1.469(7)
C7 H7 0.9500
C8 C9 1.379(6)
C8 C17 1.409(6)
C9 C10 1.438(6)
C9 H9 0.9500
C10 C11 1.406(6)
C10 C15 1.413(6)
C11 C12 1.361(7)
C11 H11 0.9500
C12 C13 1.407(7)
C12 H12 0.9500
C13 C14 1.354(7)
C13 H13 0.9500
C14 C15 1.442(7)
C14 H14 0.9500
C15 C16 1.397(6)
C16 C17 1.361(7)
C16 H16 0.9500
C17 H17 0.9500
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660608
