#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:24:29 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178468 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/89/4028996.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_4028996
loop_
_publ_author_name
'Zhu, Gangguo'
'Kong, Wei'
'Feng, Hui'
'Qian, Zhaosheng'
_publ_section_title
;
 Synthesis of (Z)-1-Thio- and (Z)-2-Thio-1-alkenyl Boronates via
 Copper-Catalyzed Regiodivergent Hydroboration of Thioacetylenes: An
 Experimental and Theoretical Study.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1786
_journal_page_last               1795
_journal_paper_doi               10.1021/jo4028402
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C16 H23 B O2 S'
_chemical_formula_weight         290.21
_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                 117.107(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.3504(16)
_cell_length_b                   6.1246(7)
_cell_length_c                   17.8836(17)
_cell_measurement_temperature    296(2)
_cell_volume                     1691.6(3)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_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  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13822
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.32
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3861
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0498
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1464
_refine_ls_wR_factor_ref         0.1828
_reflns_number_gt                2168
_reflns_number_total             3861
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4028402_si_002.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4028996
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 0.07354(4) 0.93997(13) 0.37207(4) 0.0668(3) Uani 1 1 d .
O2 O 0.20637(9) 0.5857(3) 0.23244(10) 0.0616(5) Uani 1 1 d .
O1 O 0.33653(10) 0.7551(3) 0.30444(9) 0.0588(4) Uani 1 1 d .
C15 C 0.21621(13) 0.8656(4) 0.34377(12) 0.0488(5) Uani 1 1 d .
C14 C 0.26985(13) 1.0281(4) 0.40827(12) 0.0479(5) Uani 1 1 d .
C13 C 0.35608(14) 0.9813(5) 0.46505(13) 0.0574(6) Uani 1 1 d .
H13A H 0.3800 0.8479 0.4618 0.069 Uiso 1 1 calc R
C12 C 0.23788(15) 1.2315(4) 0.41415(13) 0.0555(6) Uani 1 1 d .
H12A H 0.1814 1.2683 0.3762 0.067 Uiso 1 1 calc R
C11 C 0.13361(14) 0.8224(4) 0.32637(13) 0.0541(6) Uani 1 1 d .
H11A H 0.1053 0.7177 0.2852 0.065 Uiso 1 1 calc R
C10 C 0.35136(14) 0.5816(4) 0.25688(15) 0.0569(6) Uani 1 1 d .
C9 C 0.25761(16) 0.5256(4) 0.18942(15) 0.0594(6) Uani 1 1 d .
B B 0.25406(16) 0.7342(5) 0.29357(15) 0.0506(6) Uani 1 1 d .
C8 C 0.28765(18) 1.3812(4) 0.47496(15) 0.0653(7) Uani 1 1 d .
H8A H 0.2642 1.5154 0.4781 0.078 Uiso 1 1 calc R
C7 C -0.01664(16) 0.7526(5) 0.33893(19) 0.0791(8) Uani 1 1 d .
H7A H -0.0646 0.8267 0.3418 0.095 Uiso 1 1 calc R
H7B H -0.0350 0.7133 0.2807 0.095 Uiso 1 1 calc R
C6 C 0.40576(17) 1.1307(5) 0.52557(15) 0.0683(7) Uani 1 1 d .
H6A H 0.4626 1.0966 0.5633 0.082 Uiso 1 1 calc R
C5 C 0.37144(17) 1.3317(5) 0.53058(15) 0.0709(8) Uani 1 1 d .
H5A H 0.4051 1.4322 0.5714 0.085 Uiso 1 1 calc R
C4 C 0.41097(18) 0.6684(5) 0.22281(19) 0.0818(9) Uani 1 1 d .
H4A H 0.4670 0.6976 0.2686 0.123 Uiso 1 1 calc R
H4B H 0.3873 0.8007 0.1921 0.123 Uiso 1 1 calc R
H4C H 0.4164 0.5618 0.1861 0.123 Uiso 1 1 calc R
C3 C 0.24228(19) 0.2842(5) 0.1665(2) 0.0857(9) Uani 1 1 d .
H3A H 0.1834 0.2631 0.1247 0.128 Uiso 1 1 calc R
H3B H 0.2529 0.2006 0.2156 0.128 Uiso 1 1 calc R
H3C H 0.2808 0.2370 0.1446 0.128 Uiso 1 1 calc R
C2 C 0.39513(18) 0.3951(5) 0.31827(19) 0.0828(9) Uani 1 1 d .
H2A H 0.4524 0.4389 0.3582 0.124 Uiso 1 1 calc R
H2B H 0.3987 0.2693 0.2879 0.124 Uiso 1 1 calc R
H2C H 0.3619 0.3597 0.3473 0.124 Uiso 1 1 calc R
C1 C 0.0029(3) 0.5501(6) 0.3897(3) 0.1136(12) Uani 1 1 d .
H1A H -0.0476 0.4588 0.3685 0.170 Uiso 1 1 calc R
H1B H 0.0195 0.5869 0.4472 0.170 Uiso 1 1 calc R
H1C H 0.0494 0.4735 0.3862 0.170 Uiso 1 1 calc R
C16 C 0.2267(2) 0.6662(6) 0.11192(17) 0.0942(10) Uani 1 1 d .
H16A H 0.1688 0.6245 0.0729 0.141 Uiso 1 1 calc R
H16B H 0.2643 0.6471 0.0864 0.141 Uiso 1 1 calc R
H16C H 0.2271 0.8167 0.1272 0.141 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 0.0033 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'
B B 0.0013 0.0007 '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
C11 S1 C7 101.35(13)
B O2 C9 107.17(17)
B O1 C10 107.62(18)
C11 C15 C14 122.3(2)
C11 C15 B 116.7(2)
C14 C15 B 120.95(19)
C12 C14 C13 117.4(2)
C12 C14 C15 122.0(2)
C13 C14 C15 120.6(2)
C6 C13 C14 120.8(2)
C8 C12 C14 121.8(2)
C15 C11 S1 127.60(19)
O1 C10 C4 108.3(2)
O1 C10 C2 106.78(19)
C4 C10 C2 110.2(2)
O1 C10 C9 102.28(17)
C4 C10 C9 115.4(2)
C2 C10 C9 113.2(2)
O2 C9 C16 107.0(2)
O2 C9 C3 108.2(2)
C16 C9 C3 111.2(2)
O2 C9 C10 101.99(17)
C16 C9 C10 113.3(2)
C3 C9 C10 114.5(2)
O1 B O2 112.9(2)
O1 B C15 124.2(2)
O2 B C15 122.9(2)
C5 C8 C12 120.0(3)
C1 C7 S1 114.1(2)
C13 C6 C5 120.4(2)
C8 C5 C6 119.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C11 1.746(2)
S1 C7 1.808(3)
O2 B 1.372(3)
O2 C9 1.463(3)
O1 B 1.359(3)
O1 C10 1.455(3)
C15 C11 1.347(3)
C15 C14 1.486(3)
C15 B 1.556(3)
C14 C12 1.387(3)
C14 C13 1.403(3)
C13 C6 1.379(3)
C12 C8 1.383(3)
C10 C4 1.516(3)
C10 C2 1.525(3)
C10 C9 1.559(3)
C9 C16 1.508(4)
C9 C3 1.525(4)
C8 C5 1.370(4)
C7 C1 1.482(4)
C6 C5 1.388(4)
