#------------------------------------------------------------------------------
#$Date: 2019-11-25 15:11:18 +0200 (Mon, 25 Nov 2019) $
#$Revision: 241166 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/08/4130801.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_4130801
loop_
_publ_author_name
'Li, Yuanyuan'
'Qiu, Dachuan'
'Gu, Rongrong'
'Wang, Junli'
'Shi, Jiarong'
'Li, Yang'
_publ_section_title
;
 Aryne 1,2,3-Trifunctionalization with Aryl Allyl Sulfoxides.
;
_journal_issue                   34
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10814
_journal_page_last               10817
_journal_paper_doi               10.1021/jacs.6b06981
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C18 H18 O3 S'
_chemical_formula_sum            'C18 H18 O3 S'
_chemical_formula_weight         314.38
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                76.812(9)
_cell_angle_beta                 81.978(7)
_cell_angle_gamma                82.825(7)
_cell_formula_units_Z            2
_cell_length_a                   6.1119(3)
_cell_length_b                   10.4100(11)
_cell_length_c                   13.6296(15)
_cell_measurement_reflns_used    2628
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.13
_cell_measurement_theta_min      3.38
_cell_volume                     832.15(14)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega 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  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0462
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6110
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_min         3.38
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3759
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0554
_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)+(0.0615P)²+0.2660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1576
_reflns_number_gt                2628
_reflns_number_total             3759
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja6b06981_si_002.cif
_cod_data_source_block           yy-5-110
_cod_original_cell_volume        832.15(13)
_cod_database_code               4130801
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.21567(11) 0.79007(7) 0.67932(5) 0.0592(2) Uani 1 1 d .
O1 O 0.4615(3) 0.70489(15) 0.84850(11) 0.0468(4) Uani 1 1 d .
C5 C 0.5049(4) 0.6150(2) 0.78476(16) 0.0416(5) Uani 1 1 d .
C6 C 0.3932(4) 0.6403(2) 0.69899(16) 0.0409(5) Uani 1 1 d .
O3 O 0.6779(4) 0.9883(2) 0.88270(16) 0.0740(6) Uani 1 1 d .
O2 O 0.4098(3) 0.87260(18) 0.97216(14) 0.0662(5) Uani 1 1 d .
C12 C 0.1179(4) 0.7965(2) 0.56190(19) 0.0476(5) Uani 1 1 d .
C7 C 0.4249(4) 0.5494(2) 0.63702(17) 0.0462(5) Uani 1 1 d .
H7A H 0.3508 0.5650 0.5797 0.055 Uiso 1 1 calc R
C8 C 0.5669(4) 0.4356(2) 0.66080(19) 0.0551(6) Uani 1 1 d .
H8A H 0.5904 0.3753 0.6186 0.066 Uiso 1 1 calc R
C4 C 0.6445(4) 0.4995(2) 0.81084(18) 0.0521(6) Uani 1 1 d .
C11 C 0.5520(4) 0.8912(2) 0.90148(17) 0.0471(5) Uani 1 1 d .
C14 C 0.1172(4) 0.8914(2) 0.3847(2) 0.0542(6) Uani 1 1 d .
H14A H 0.1823 0.9438 0.3259 0.065 Uiso 1 1 calc R
C15 C -0.0699(4) 0.8324(2) 0.38031(19) 0.0518(6) Uani 1 1 d .
C10 C 0.6084(4) 0.8048(2) 0.82605(18) 0.0505(6) Uani 1 1 d .
H10A H 0.5957 0.8574 0.7581 0.061 Uiso 1 1 calc R
H10B H 0.7601 0.7648 0.8288 0.061 Uiso 1 1 calc R
C13 C 0.2109(4) 0.8750(2) 0.4737(2) 0.0533(6) Uani 1 1 d .
H13A H 0.3365 0.9167 0.4744 0.064 Uiso 1 1 calc R
C17 C -0.0659(4) 0.7336(3) 0.5580(2) 0.0604(7) Uani 1 1 d .
H17A H -0.1288 0.6791 0.6164 0.072 Uiso 1 1 calc R
C9 C 0.6735(5) 0.4109(3) 0.7463(2) 0.0611(7) Uani 1 1 d .
H9A H 0.7672 0.3333 0.7615 0.073 Uiso 1 1 calc R
C16 C -0.1564(4) 0.7510(3) 0.4684(2) 0.0634(7) Uani 1 1 d .
H16A H -0.2790 0.7070 0.4671 0.076 Uiso 1 1 calc R
C18 C -0.1772(5) 0.8555(3) 0.2845(2) 0.0746(8) Uani 1 1 d .
H18A H -0.0950 0.9143 0.2314 0.112 Uiso 1 1 calc R
H18B H -0.3268 0.8946 0.2955 0.112 Uiso 1 1 calc R
H18C H -0.1782 0.7726 0.2651 0.112 Uiso 1 1 calc R
C3 C 0.7568(5) 0.4674(3) 0.9071(2) 0.0694(8) Uani 1 1 d .
H3A H 0.7409 0.5460 0.9353 0.083 Uiso 1 1 calc R
H3B H 0.6813 0.3995 0.9562 0.083 Uiso 1 1 calc R
C2 C 0.9884(6) 0.4224(4) 0.8921(3) 0.0900(11) Uani 1 1 d .
H2A H 1.0766 0.4823 0.8478 0.108 Uiso 1 1 calc R
C1 C 1.0910(6) 0.3108(4) 0.9315(3) 0.1051(14) Uani 1 1 d .
H1A H 1.0128 0.2464 0.9765 0.158 Uiso 1 1 calc R
H1B H 1.2433 0.2947 0.9150 0.158 Uiso 1 1 calc R
H3 H 0.652(6) 1.028(4) 0.929(3) 0.114(14) Uiso 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'
O O 0.0106 0.0060 '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
C12 S1 C6 103.77(10)
C5 O1 C10 114.00(17)
C4 C5 C6 121.64(19)
C4 C5 O1 120.2(2)
C6 C5 O1 118.04(19)
C7 C6 C5 119.3(2)
C7 C6 S1 125.13(17)
C5 C6 S1 115.59(16)
C17 C12 C13 118.7(2)
C17 C12 S1 120.6(2)
C13 C12 S1 120.43(19)
C8 C7 C6 119.7(2)
C9 C8 C7 120.4(2)
C5 C4 C9 117.4(2)
C5 C4 C3 122.0(2)
C9 C4 C3 120.5(2)
O2 C11 O3 123.8(2)
O2 C11 C10 124.2(2)
O3 C11 C10 112.0(2)
C15 C14 C13 122.1(2)
C14 C15 C16 117.2(2)
C14 C15 C18 121.8(3)
C16 C15 C18 121.0(2)
O1 C10 C11 109.16(19)
C14 C13 C12 119.9(2)
C16 C17 C12 120.4(2)
C8 C9 C4 121.5(2)
C17 C16 C15 121.7(2)
C2 C3 C4 113.7(2)
C1 C2 C3 129.1(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C12 1.769(2)
S1 C6 1.774(2)
O1 C5 1.395(2)
O1 C10 1.411(3)
C5 C4 1.390(3)
C5 C6 1.393(3)
C6 C7 1.385(3)
O3 C11 1.304(3)
O2 C11 1.202(3)
C12 C17 1.382(3)
C12 C13 1.383(4)
C7 C8 1.382(3)
C8 C9 1.371(3)
C4 C9 1.394(3)
C4 C3 1.516(3)
C11 C10 1.494(3)
C14 C15 1.378(3)
C14 C13 1.379(3)
C15 C16 1.382(4)
C15 C18 1.500(4)
C17 C16 1.376(4)
C3 C2 1.436(5)
C2 C1 1.288(5)
