#------------------------------------------------------------------------------
#$Date: 2019-11-23 19:10:47 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234590 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/63/4036349.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_4036349
loop_
_publ_author_name
'Yang, Zheng'
'Hao, Wen-Juan'
'Wang, Shu-Liang'
'Zhang, Jin-Peng'
'Jiang, Bo'
'Li, Guigen'
'Tu, Shu-Jiang'
_publ_section_title
;
 Synthesis of Allenyl Sulfones via a TBHP/TBAI-Mediated Reaction of
 Propargyl Alcohols with Sulfonyl Hydrazides.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9224
_journal_page_last               9230
_journal_paper_doi               10.1021/acs.joc.5b01684
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C28 H22 O2 S'
_chemical_formula_weight         422.52
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 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                 108.442(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5311(9)
_cell_length_b                   14.0448(12)
_cell_length_c                   15.9503(14)
_cell_measurement_reflns_used    1382
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.342
_cell_measurement_theta_min      2.502
_cell_volume                     2238.0(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0739
_diffrn_reflns_av_sigmaI/netI    0.1089
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10917
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.9884
_exptl_absorpt_correction_T_min  0.9803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.1371
_refine_ls_R_factor_gt           0.0496
_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)+(0.0003P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0508
_refine_ls_wR_factor_ref         0.0588
_reflns_number_gt                1746
_reflns_number_total             3945
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01684_si_002.cif
_cod_data_source_block           150611a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4036349
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O1 O 0.80697(17) 0.36797(13) 0.51758(11) 0.0755(6) Uani 1 1 d .
O2 O 0.69408(17) 0.21883(13) 0.45239(11) 0.0773(6) Uani 1 1 d .
S1 S 0.72240(8) 0.28926(6) 0.52192(5) 0.0604(2) Uani 1 1 d .
C1 C 0.7965(3) 0.23129(16) 0.62636(17) 0.0452(7) Uani 1 1 d .
C2 C 0.7218(3) 0.21814(18) 0.67568(18) 0.0477(7) Uani 1 1 d .
C3 C 0.6430(3) 0.2049(2) 0.72348(17) 0.0470(7) Uani 1 1 d .
C4 C 0.9391(3) 0.20193(17) 0.6499(2) 0.0481(7) Uani 1 1 d .
C5 C 1.0019(3) 0.18784(18) 0.5868(2) 0.0653(9) Uani 1 1 d .
H5 H 0.9566 0.2017 0.5279 0.078 Uiso 1 1 calc R
C6 C 1.1316(3) 0.1534(2) 0.6105(2) 0.0759(10) Uani 1 1 d .
H6 H 1.1735 0.1442 0.5678 0.091 Uiso 1 1 calc R
C7 C 1.1982(3) 0.1327(2) 0.6980(3) 0.0736(11) Uani 1 1 d .
H7 H 1.2844 0.1078 0.7140 0.088 Uiso 1 1 calc R
C8 C 1.1384(3) 0.1486(2) 0.7615(2) 0.0716(10) Uani 1 1 d .
H8 H 1.1849 0.1364 0.8205 0.086 Uiso 1 1 calc R
C9 C 1.0090(3) 0.18287(18) 0.73781(19) 0.0615(9) Uani 1 1 d .
H9 H 0.9684 0.1932 0.7810 0.074 Uiso 1 1 calc R
C10 C 0.6224(3) 0.2809(2) 0.78200(17) 0.0475(7) Uani 1 1 d .
C11 C 0.7144(3) 0.3528(2) 0.81150(18) 0.0605(9) Uani 1 1 d .
H11 H 0.7945 0.3509 0.7984 0.073 Uiso 1 1 calc R
C12 C 0.6900(4) 0.4272(2) 0.8598(2) 0.0795(11) Uani 1 1 d .
H12 H 0.7536 0.4751 0.8794 0.095 Uiso 1 1 calc R
C13 C 0.5720(4) 0.4315(2) 0.8795(2) 0.0871(11) Uani 1 1 d .
H13 H 0.5554 0.4824 0.9118 0.104 Uiso 1 1 calc R
C14 C 0.4788(3) 0.3601(3) 0.8515(2) 0.0790(10) Uani 1 1 d .
H14 H 0.3994 0.3621 0.8652 0.095 Uiso 1 1 calc R
C15 C 0.5043(3) 0.2858(2) 0.80274(18) 0.0634(9) Uani 1 1 d .
H15 H 0.4409 0.2378 0.7834 0.076 Uiso 1 1 calc R
C16 C 0.5706(3) 0.11188(19) 0.7157(2) 0.0470(8) Uani 1 1 d .
C17 C 0.5766(2) 0.0602(2) 0.79026(19) 0.0575(8) Uani 1 1 d .
H17 H 0.6223 0.0846 0.8458 0.069 Uiso 1 1 calc R
C18 C 0.5151(3) -0.0278(2) 0.7831(2) 0.0672(10) Uani 1 1 d .
H18 H 0.5208 -0.0629 0.8336 0.081 Uiso 1 1 calc R
C19 C 0.4457(3) -0.0634(2) 0.7011(2) 0.0679(10) Uani 1 1 d .
H19 H 0.4022 -0.1217 0.6964 0.081 Uiso 1 1 calc R
C20 C 0.4401(3) -0.0135(2) 0.6266(2) 0.0661(9) Uani 1 1 d .
H20 H 0.3950 -0.0384 0.5711 0.079 Uiso 1 1 calc R
C21 C 0.5018(3) 0.0739(2) 0.63413(19) 0.0597(8) Uani 1 1 d .
H21 H 0.4970 0.1081 0.5833 0.072 Uiso 1 1 calc R
C22 C 0.5706(3) 0.3316(2) 0.53098(19) 0.0543(8) Uani 1 1 d .
C23 C 0.5712(3) 0.4083(2) 0.58544(19) 0.0641(9) Uani 1 1 d .
H23 H 0.6502 0.4411 0.6127 0.077 Uiso 1 1 calc R
C24 C 0.4535(4) 0.4356(2) 0.5988(2) 0.0759(10) Uani 1 1 d .
H24 H 0.4542 0.4865 0.6362 0.091 Uiso 1 1 calc R
C25 C 0.3340(4) 0.3890(2) 0.5578(2) 0.0714(10) Uani 1 1 d .
C26 C 0.3362(3) 0.3148(2) 0.5013(2) 0.0730(10) Uani 1 1 d .
H26 H 0.2568 0.2837 0.4715 0.088 Uiso 1 1 calc R
C27 C 0.4534(3) 0.2859(2) 0.48829(18) 0.0656(9) Uani 1 1 d .
H27 H 0.4528 0.2354 0.4505 0.079 Uiso 1 1 calc R
C28 C 0.2076(3) 0.41675(19) 0.5761(2) 0.1022(12) Uani 1 1 d .
H28A H 0.1338 0.3811 0.5383 0.153 Uiso 1 1 calc R
H28B H 0.1915 0.4836 0.5651 0.153 Uiso 1 1 calc R
H28C H 0.2166 0.4033 0.6367 0.153 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'
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
O1 S1 O2 118.09(13)
O1 S1 C22 109.80(13)
O2 S1 C22 108.84(13)
O1 S1 C1 107.46(11)
O2 S1 C1 108.98(12)
C22 S1 C1 102.53(14)
C2 C1 C4 124.6(3)
C2 C1 S1 117.5(2)
C4 C1 S1 117.9(2)
C1 C2 C3 178.3(3)
C2 C3 C10 120.9(3)
C2 C3 C16 118.4(3)
C10 C3 C16 120.6(3)
C5 C4 C9 119.0(3)
C5 C4 C1 122.2(3)
C9 C4 C1 118.7(3)
C4 C5 C6 120.6(3)
C4 C5 H5 119.7
C6 C5 H5 119.7
C7 C6 C5 119.4(3)
C7 C6 H6 120.3
C5 C6 H6 120.3
C8 C7 C6 120.5(3)
C8 C7 H7 119.7
C6 C7 H7 119.7
C7 C8 C9 120.0(3)
C7 C8 H8 120.0
C9 C8 H8 120.0
C8 C9 C4 120.4(3)
C8 C9 H9 119.8
C4 C9 H9 119.8
C11 C10 C15 118.0(3)
C11 C10 C3 121.2(3)
C15 C10 C3 120.6(3)
C12 C11 C10 121.0(3)
C12 C11 H11 119.5
C10 C11 H11 119.5
C11 C12 C13 120.3(3)
C11 C12 H12 119.8
C13 C12 H12 119.8
C14 C13 C12 119.8(3)
C14 C13 H13 120.1
C12 C13 H13 120.1
C13 C14 C15 119.3(3)
C13 C14 H14 120.3
C15 C14 H14 120.3
C14 C15 C10 121.5(3)
C14 C15 H15 119.3
C10 C15 H15 119.3
C17 C16 C21 118.5(3)
C17 C16 C3 120.4(3)
C21 C16 C3 121.1(3)
C16 C17 C18 120.5(3)
C16 C17 H17 119.8
C18 C17 H17 119.8
C19 C18 C17 119.8(3)
C19 C18 H18 120.1
C17 C18 H18 120.1
C20 C19 C18 120.4(3)
C20 C19 H19 119.8
C18 C19 H19 119.8
C19 C20 C21 119.5(3)
C19 C20 H20 120.2
C21 C20 H20 120.2
C20 C21 C16 121.3(3)
C20 C21 H21 119.4
C16 C21 H21 119.4
C27 C22 C23 120.1(3)
C27 C22 S1 120.2(3)
C23 C22 S1 119.5(3)
C24 C23 C22 119.3(3)
C24 C23 H23 120.4
C22 C23 H23 120.4
C23 C24 C25 121.6(3)
C23 C24 H24 119.2
C25 C24 H24 119.2
C26 C25 C24 117.6(3)
C26 C25 C28 121.4(4)
C24 C25 C28 121.0(3)
C27 C26 C25 121.4(3)
C27 C26 H26 119.3
C25 C26 H26 119.3
C22 C27 C26 119.9(3)
C22 C27 H27 120.0
C26 C27 H27 120.0
C25 C28 H28A 109.5
C25 C28 H28B 109.5
H28A C28 H28B 109.5
C25 C28 H28C 109.5
H28A C28 H28C 109.5
H28B C28 H28C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 S1 1.4350(17)
O2 S1 1.4451(16)
S1 C22 1.753(3)
S1 C1 1.796(2)
C1 C2 1.290(3)
C1 C4 1.487(3)
C2 C3 1.306(3)
C3 C10 1.478(3)
C3 C16 1.498(3)
C4 C5 1.383(3)
C4 C9 1.388(3)
C5 C6 1.384(3)
C5 H5 0.9300
C6 C7 1.380(4)
C6 H6 0.9300
C7 C8 1.370(4)
C7 H7 0.9300
C8 C9 1.380(3)
C8 H8 0.9300
C9 H9 0.9300
C10 C11 1.376(3)
C10 C15 1.386(3)
C11 C12 1.370(3)
C11 H11 0.9300
C12 C13 1.377(4)
C12 H12 0.9300
C13 C14 1.374(4)
C13 H13 0.9300
C14 C15 1.378(3)
C14 H14 0.9300
C15 H15 0.9300
C16 C17 1.378(3)
C16 C21 1.381(3)
C17 C18 1.383(3)
C17 H17 0.9300
C18 C19 1.374(3)
C18 H18 0.9300
C19 C20 1.364(3)
C19 H19 0.9300
C20 C21 1.376(3)
C20 H20 0.9300
C21 H21 0.9300
C22 C27 1.367(3)
C22 C23 1.383(3)
C23 C24 1.377(4)
C23 H23 0.9300
C24 C25 1.384(4)
C24 H24 0.9300
C25 C26 1.383(4)
C25 C28 1.502(4)
C26 C27 1.375(3)
C26 H26 0.9300
C27 H27 0.9300
C28 H28A 0.9600
C28 H28B 0.9600
C28 H28C 0.9600
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
O1 S1 C1 C2 127.0(2)
O2 S1 C1 C2 -104.0(2)
C22 S1 C1 C2 11.3(3)
O1 S1 C1 C4 -53.0(2)
O2 S1 C1 C4 76.1(2)
C22 S1 C1 C4 -168.7(2)
C4 C1 C2 C3 -156(10)
S1 C1 C2 C3 24(10)
C1 C2 C3 C10 -108(10)
C1 C2 C3 C16 70(10)
C2 C1 C4 C5 158.0(3)
S1 C1 C4 C5 -22.1(3)
C2 C1 C4 C9 -18.3(4)
S1 C1 C4 C9 161.66(19)
C9 C4 C5 C6 1.3(4)
C1 C4 C5 C6 -174.9(2)
C4 C5 C6 C7 0.2(4)
C5 C6 C7 C8 -1.9(4)
C6 C7 C8 C9 2.0(5)
C7 C8 C9 C4 -0.4(4)
C5 C4 C9 C8 -1.2(4)
C1 C4 C9 C8 175.2(2)
C2 C3 C10 C11 -22.2(4)
C16 C3 C10 C11 159.6(2)
C2 C3 C10 C15 152.5(3)
C16 C3 C10 C15 -25.7(4)
C15 C10 C11 C12 -0.1(4)
C3 C10 C11 C12 174.7(3)
C10 C11 C12 C13 -0.2(5)
C11 C12 C13 C14 0.7(5)
C12 C13 C14 C15 -0.9(5)
C13 C14 C15 C10 0.5(5)
C11 C10 C15 C14 0.0(4)
C3 C10 C15 C14 -174.9(3)
C2 C3 C16 C17 128.7(3)
C10 C3 C16 C17 -53.1(4)
C2 C3 C16 C21 -48.3(4)
C10 C3 C16 C21 129.9(3)
C21 C16 C17 C18 0.2(4)
C3 C16 C17 C18 -176.9(2)
C16 C17 C18 C19 -1.1(4)
C17 C18 C19 C20 1.8(5)
C18 C19 C20 C21 -1.6(5)
C19 C20 C21 C16 0.7(4)
C17 C16 C21 C20 0.0(4)
C3 C16 C21 C20 177.1(2)
O1 S1 C22 C27 142.4(2)
O2 S1 C22 C27 11.7(3)
C1 S1 C22 C27 -103.6(2)
O1 S1 C22 C23 -41.2(3)
O2 S1 C22 C23 -171.8(2)
C1 S1 C22 C23 72.8(3)
C27 C22 C23 C24 2.6(4)
S1 C22 C23 C24 -173.9(2)
C22 C23 C24 C25 -1.1(5)
C23 C24 C25 C26 -1.2(5)
C23 C24 C25 C28 177.3(3)
C24 C25 C26 C27 2.1(5)
C28 C25 C26 C27 -176.4(3)
C23 C22 C27 C26 -1.7(4)
S1 C22 C27 C26 174.8(2)
C25 C26 C27 C22 -0.7(5)
