#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:44:39 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180313 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/27/7152711.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_7152711
loop_
_publ_author_name
'Huang, Chuhui'
'Kothandaraman, Prasath'
'Koh, Bing Qin'
'Chan, Philip Wai Hong'
_publ_section_title
;
 Study of substrate dependence on the chemoselectivity of the
 gold-catalysed cycloisomerisation of aryl substituted 1,7-enynes.
;
_journal_issue                   45
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9067
_journal_page_last               9078
_journal_paper_doi               10.1039/c2ob26458g
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C20 H20 F N O2 S'
_chemical_formula_sum            'C20 H20 F N O2 S'
_chemical_formula_weight         357.43
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 124.4450(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.8723(11)
_cell_length_b                   8.1821(3)
_cell_length_c                   17.9935(7)
_cell_measurement_reflns_used    6454
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      29.48
_cell_measurement_theta_min      2.74
_cell_volume                     3505.4(2)
_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      103(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            22939
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_correction_T_min  0.9596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         5069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0434
_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)+(0.0773P)²+1.2931P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1434
_reflns_number_gt                3915
_reflns_number_total             5069
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob26458g.txt
_cod_data_source_block           chan150
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7152711
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.33081(6) 0.11834(19) 0.59431(10) 0.0246(3) Uani 1 1 d .
C2 C 0.33415(8) 0.0806(2) 0.67301(11) 0.0335(4) Uani 1 1 d .
H2 H 0.3043 0.0223 0.6689 0.040 Uiso 1 1 calc R
C3 C 0.38034(8) 0.1269(3) 0.75696(11) 0.0359(4) Uani 1 1 d .
H3 H 0.3828 0.0985 0.8103 0.043 Uiso 1 1 calc R
C4 C 0.42242(8) 0.2147(2) 0.76140(11) 0.0323(4) Uani 1 1 d .
C5 C 0.42061(8) 0.2567(3) 0.68622(13) 0.0431(5) Uani 1 1 d .
H5 H 0.4501 0.3181 0.6908 0.052 Uiso 1 1 calc R
C6 C 0.37440(8) 0.2070(3) 0.60289(12) 0.0378(4) Uani 1 1 d .
H6 H 0.3727 0.2347 0.5501 0.045 Uiso 1 1 calc R
C7 C 0.13603(6) -0.01533(17) 0.09191(9) 0.0184(3) Uani 1 1 d .
C8 C 0.16216(6) 0.13692(18) 0.11485(10) 0.0207(3) Uani 1 1 d .
H8 H 0.2001 0.1480 0.1650 0.025 Uiso 1 1 calc R
C9 C 0.13202(7) 0.27258(18) 0.06337(11) 0.0241(3) Uani 1 1 d .
H9 H 0.1497 0.3766 0.0789 0.029 Uiso 1 1 calc R
C10 C 0.07623(7) 0.25907(19) -0.01071(10) 0.0242(3) Uani 1 1 d .
C11 C 0.05142(6) 0.10413(19) -0.03310(10) 0.0237(3) Uani 1 1 d .
H11 H 0.0138 0.0924 -0.0840 0.028 Uiso 1 1 calc R
C12 C 0.08051(6) -0.03249(18) 0.01724(10) 0.0219(3) Uani 1 1 d .
H12 H 0.0630 -0.1368 0.0013 0.026 Uiso 1 1 calc R
C13 C 0.04378(8) 0.4072(2) -0.06496(13) 0.0386(5) Uani 1 1 d .
H13A H 0.0431 0.4115 -0.1200 0.058 Uiso 1 1 calc R
H13B H 0.0619 0.5060 -0.0292 0.058 Uiso 1 1 calc R
H13C H 0.0052 0.4006 -0.0810 0.058 Uiso 1 1 calc R
C14 C 0.10365(6) -0.1588(2) 0.21678(11) 0.0272(4) Uani 1 1 d .
H14A H 0.0798 -0.2315 0.1645 0.033 Uiso 1 1 calc R
H14B H 0.0900 -0.0453 0.1981 0.033 Uiso 1 1 calc R
C15 C 0.09934(7) -0.2080(2) 0.29416(12) 0.0337(4) Uani 1 1 d .
H15A H 0.0642 -0.1631 0.2834 0.040 Uiso 1 1 calc R
H15B H 0.0975 -0.3286 0.2960 0.040 Uiso 1 1 calc R
C16 C 0.14807(7) -0.1478(3) 0.38275(12) 0.0339(4) Uani 1 1 d .
H16 H 0.1466 -0.1612 0.4338 0.041 Uiso 1 1 calc R
C17 C 0.19381(6) -0.0763(2) 0.39552(10) 0.0245(3) Uani 1 1 d .
C18 C 0.20009(6) -0.05466(19) 0.31853(10) 0.0220(3) Uani 1 1 d .
H18A H 0.1903 0.0588 0.2957 0.026 Uiso 1 1 calc R
H18B H 0.2396 -0.0747 0.3398 0.026 Uiso 1 1 calc R
C19 C 0.23878(6) -0.0186(2) 0.48420(10) 0.0273(4) Uani 1 1 d .
H19 H 0.2356 -0.0428 0.5328 0.033 Uiso 1 1 calc R
C20 C 0.28410(7) 0.06493(19) 0.50411(10) 0.0244(3) Uani 1 1 d .
H20 H 0.2865 0.0928 0.4551 0.029 Uiso 1 1 calc R
F1 F 0.46770(5) 0.26218(15) 0.84396(7) 0.0427(3) Uani 1 1 d .
N1 N 0.16278(5) -0.17045(15) 0.24530(8) 0.0197(3) Uani 1 1 d .
O1 O 0.22994(4) -0.17230(14) 0.20135(7) 0.0247(3) Uani 1 1 d .
O2 O 0.14087(5) -0.32868(13) 0.11197(8) 0.0262(3) Uani 1 1 d .
S1 S 0.170868(14) -0.18500(4) 0.16234(2) 0.01885(12) 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'
O O 0.0106 0.0060 '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'
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
C6 C1 C2 117.74(15)
C6 C1 C20 119.12(16)
C2 C1 C20 123.12(16)
C3 C2 C1 121.03(18)
C3 C2 H2 119.5
C1 C2 H2 119.5
C4 C3 C2 118.67(17)
C4 C3 H3 120.7
C2 C3 H3 120.7
F1 C4 C5 118.77(18)
F1 C4 C3 118.82(17)
C5 C4 C3 122.41(16)
C4 C5 C6 118.0(2)
C4 C5 H5 121.0
C6 C5 H5 121.0
C1 C6 C5 122.11(18)
C1 C6 H6 118.9
C5 C6 H6 118.9
C8 C7 C12 120.58(13)
C8 C7 S1 119.90(11)
C12 C7 S1 119.32(11)
C9 C8 C7 119.11(13)
C9 C8 H8 120.4
C7 C8 H8 120.4
C8 C9 C10 121.41(14)
C8 C9 H9 119.3
C10 C9 H9 119.3
C9 C10 C11 118.20(14)
C9 C10 C13 120.90(15)
C11 C10 C13 120.91(14)
C12 C11 C10 121.41(13)
C12 C11 H11 119.3
C10 C11 H11 119.3
C11 C12 C7 119.28(13)
C11 C12 H12 120.4
C7 C12 H12 120.4
C10 C13 H13A 109.5
C10 C13 H13B 109.5
H13A C13 H13B 109.5
C10 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
N1 C14 C15 109.92(13)
N1 C14 H14A 109.7
C15 C14 H14A 109.7
N1 C14 H14B 109.7
C15 C14 H14B 109.7
H14A C14 H14B 108.2
C16 C15 C14 112.02(15)
C16 C15 H15A 109.2
C14 C15 H15A 109.2
C16 C15 H15B 109.2
C14 C15 H15B 109.2
H15A C15 H15B 107.9
C17 C16 C15 124.71(16)
C17 C16 H16 117.6
C15 C16 H16 117.6
C16 C17 C19 120.79(15)
C16 C17 C18 120.89(14)
C19 C17 C18 118.33(14)
N1 C18 C17 109.77(13)
N1 C18 H18A 109.7
C17 C18 H18A 109.7
N1 C18 H18B 109.7
C17 C18 H18B 109.7
H18A C18 H18B 108.2
C20 C19 C17 126.38(16)
C20 C19 H19 116.8
C17 C19 H19 116.8
C19 C20 C1 126.60(16)
C19 C20 H20 116.7
C1 C20 H20 116.7
C18 N1 C14 112.53(12)
C18 N1 S1 116.75(10)
C14 N1 S1 114.75(10)
O1 S1 O2 119.56(7)
O1 S1 N1 106.93(7)
O2 S1 N1 106.74(7)
O1 S1 C7 109.39(7)
O2 S1 C7 107.20(7)
N1 S1 C7 106.27(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.384(3)
C1 C2 1.398(2)
C1 C20 1.472(2)
C2 C3 1.387(2)
C2 H2 0.9500
C3 C4 1.374(3)
C3 H3 0.9500
C4 F1 1.3675(19)
C4 C5 1.368(3)
C5 C6 1.390(3)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.393(2)
C7 C12 1.3992(19)
C7 S1 1.7616(14)
C8 C9 1.391(2)
C8 H8 0.9500
C9 C10 1.398(2)
C9 H9 0.9500
C10 C11 1.399(2)
C10 C13 1.505(2)
C11 C12 1.384(2)
C11 H11 0.9500
C12 H12 0.9500
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 N1 1.4818(19)
C14 C15 1.521(3)
C14 H14A 0.9900
C14 H14B 0.9900
C15 C16 1.492(2)
C15 H15A 0.9900
C15 H15B 0.9900
C16 C17 1.341(2)
C16 H16 0.9500
C17 C19 1.453(2)
C17 C18 1.506(2)
C18 N1 1.4795(18)
C18 H18A 0.9900
C18 H18B 0.9900
C19 C20 1.333(2)
C19 H19 0.9500
C20 H20 0.9500
N1 S1 1.6406(14)
O1 S1 1.4347(11)
O2 S1 1.4373(11)
