#------------------------------------------------------------------------------
#$Date: 2020-07-08 04:14:50 +0300 (Wed, 08 Jul 2020) $
#$Revision: 254098 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/85/1558532.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_1558532
loop_
_publ_author_name
'Zhang, Xueying'
'Zhang, Zhansong'
'Song, Jin-Na'
'Wang, Zikun'
_publ_section_title
;
 Reductive radical-initiated 1,2-C migration assisted by azidyl group
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02559C
_journal_year                    2020
_chemical_formula_moiety         'C22 H20 O3 S'
_chemical_formula_sum            'C22 H20 O3 S'
_chemical_formula_weight         364.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-02-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-02-16 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.359(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.855(3)
_cell_length_b                   5.7928(7)
_cell_length_c                   16.427(2)
_cell_measurement_reflns_used    1469
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.4250
_cell_measurement_theta_min      4.2590
_cell_volume                     1821.9(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.854
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.854
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7635
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.201
_diffrn_reflns_theta_min         3.530
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77576
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0029(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0438P)²+0.1879P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1139
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2750
_reflns_number_total             4207
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02559c2.cif
_cod_data_source_block           1
_cod_database_code               1558532
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.971
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C20(H20), C10(H10), C11(H11), C5(H5), C12(H12), C22(H22), C1(H1),
 C19(H19), C3(H3), C13(H13), C17(H17), C2(H2), C4(H4)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.30361(3) 0.89300(9) 0.08956(3) 0.04093(17) Uani 1 1 d . . . . .
O2 O 0.28407(8) 0.6599(2) 0.10130(9) 0.0538(4) Uani 1 1 d . . . . .
C6 C 0.04551(10) 1.1018(4) 0.11005(12) 0.0417(5) Uani 1 1 d . . . . .
C14 C 0.22852(10) 1.0725(4) 0.07155(12) 0.0410(5) Uani 1 1 d . . . . .
H14A H 0.243910 1.230925 0.083029 0.049 Uiso 1 1 calc R . . . .
H14B H 0.203721 1.062911 0.012234 0.049 Uiso 1 1 calc R . . . .
C15 C 0.36161(10) 0.9900(3) 0.18389(12) 0.0373(4) Uani 1 1 d . . . . .
O3 O 0.33472(8) 0.9421(3) 0.02181(8) 0.0571(4) Uani 1 1 d . . . . .
C8 C 0.17710(10) 1.0163(3) 0.12381(11) 0.0382(5) Uani 1 1 d . . . . .
H8 H 0.162399 0.854875 0.114129 0.046 Uiso 1 1 calc R . . . .
O1 O 0.11846(8) 1.3552(3) 0.06082(12) 0.0750(6) Uani 1 1 d . . . . .
C16 C 0.37091(10) 0.8620(4) 0.25670(12) 0.0426(5) Uani 1 1 d . . . . .
H16 H 0.348833 0.720028 0.255677 0.051 Uiso 1 1 calc R . . . .
C20 C 0.39523(11) 1.1984(4) 0.18490(13) 0.0459(5) Uani 1 1 d . . . . .
H20 H 0.389504 1.282928 0.135390 0.055 Uiso 1 1 calc R . . . .
C9 C 0.20743(10) 1.0547(3) 0.21789(12) 0.0376(5) Uani 1 1 d . . . . .
C10 C 0.20546(10) 0.8805(4) 0.27519(13) 0.0446(5) Uani 1 1 d . . . . .
H10 H 0.183893 0.740991 0.255978 0.054 Uiso 1 1 calc R . . . .
C7 C 0.11311(11) 1.1724(4) 0.09397(13) 0.0456(5) Uani 1 1 d . . . . .
C11 C 0.23515(11) 0.9123(4) 0.36033(13) 0.0512(6) Uani 1 1 d . . . . .
H11 H 0.233780 0.793925 0.398100 0.061 Uiso 1 1 calc R . . . .
C5 C 0.03496(11) 0.8939(4) 0.14590(14) 0.0520(6) Uani 1 1 d . . . . .
H5 H 0.071128 0.786984 0.160263 0.062 Uiso 1 1 calc R . . . .
C12 C 0.26667(12) 1.1176(4) 0.38951(13) 0.0539(6) Uani 1 1 d . . . . .
H12 H 0.287033 1.138095 0.446919 0.065 Uiso 1 1 calc R . . . .
C22 C 0.23847(11) 1.2626(4) 0.24845(13) 0.0462(5) Uani 1 1 d . . . . .
H22 H 0.239356 1.382689 0.211169 0.055 Uiso 1 1 calc R . . . .
C1 C -0.00982(11) 1.2555(4) 0.08769(14) 0.0535(6) Uani 1 1 d . . . . .
H1 H -0.003842 1.395542 0.062799 0.064 Uiso 1 1 calc R . . . .
C19 C 0.43735(11) 1.2806(4) 0.25979(14) 0.0503(6) Uani 1 1 d . . . . .
H19 H 0.460297 1.420882 0.260531 0.060 Uiso 1 1 calc R . . . .
C3 C -0.08234(12) 0.9991(5) 0.13870(15) 0.0629(7) Uani 1 1 d . . . . .
H3 H -0.125154 0.965525 0.148970 0.075 Uiso 1 1 calc R . . . .
C13 C 0.26811(12) 1.2930(4) 0.33377(14) 0.0528(6) Uani 1 1 d . . . . .
H13 H 0.289134 1.432928 0.353601 0.063 Uiso 1 1 calc R . . . .
C17 C 0.41318(11) 0.9466(4) 0.33082(13) 0.0507(6) Uani 1 1 d . . . . .
H17 H 0.419799 0.859880 0.379956 0.061 Uiso 1 1 calc R . . . .
C18 C 0.44601(11) 1.1574(4) 0.33396(14) 0.0539(6) Uani 1 1 d . . . . .
C2 C -0.07302(12) 1.2045(5) 0.10166(16) 0.0656(7) Uani 1 1 d . . . . .
H2 H -0.109716 1.309160 0.086048 0.079 Uiso 1 1 calc R . . . .
C4 C -0.02858(12) 0.8431(5) 0.16062(15) 0.0590(6) Uani 1 1 d . . . . .
H4 H -0.035013 0.703362 0.185381 0.071 Uiso 1 1 calc R . . . .
C21 C 0.48931(16) 1.2563(6) 0.41624(16) 0.0933(10) Uani 1 1 d . . . . .
H21A H 0.506850 1.405086 0.406191 0.140 Uiso 1 1 calc GR . . . .
H21B H 0.527749 1.154901 0.439907 0.140 Uiso 1 1 calc GR . . . .
H21C H 0.460867 1.271900 0.454946 0.140 Uiso 1 1 calc GR . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 C14 109.20(10) . . ?
O2 S1 C15 108.66(9) . . ?
O2 S1 O3 118.57(10) . . ?
C15 S1 C14 106.51(9) . . ?
O3 S1 C14 105.61(9) . . ?
O3 S1 C15 107.66(9) . . ?
C5 C6 C7 124.04(19) . . ?
C5 C6 C1 118.3(2) . . ?
C1 C6 C7 117.7(2) . . ?
C8 C14 S1 115.88(14) . . ?
C16 C15 S1 119.90(16) . . ?
C16 C15 C20 120.55(19) . . ?
C20 C15 S1 119.49(15) . . ?
C9 C8 C14 113.28(16) . . ?
C9 C8 C7 108.13(15) . . ?
C7 C8 C14 108.35(16) . . ?
C17 C16 C15 119.2(2) . . ?
C19 C20 C15 119.45(19) . . ?
C10 C9 C8 120.59(18) . . ?
C22 C9 C8 120.97(17) . . ?
C22 C9 C10 118.44(18) . . ?
C11 C10 C9 120.7(2) . . ?
C6 C7 C8 119.39(18) . . ?
O1 C7 C6 120.70(19) . . ?
O1 C7 C8 119.84(19) . . ?
C12 C11 C10 120.3(2) . . ?
C4 C5 C6 120.7(2) . . ?
C11 C12 C13 119.8(2) . . ?
C13 C22 C9 120.5(2) . . ?
C2 C1 C6 121.0(2) . . ?
C20 C19 C18 120.9(2) . . ?
C2 C3 C4 120.1(2) . . ?
C12 C13 C22 120.3(2) . . ?
C16 C17 C18 121.4(2) . . ?
C19 C18 C21 120.1(2) . . ?
C17 C18 C19 118.5(2) . . ?
C17 C18 C21 121.4(2) . . ?
C1 C2 C3 120.0(2) . . ?
C3 C4 C5 119.9(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4319(15) . ?
S1 C14 1.777(2) . ?
S1 C15 1.760(2) . ?
S1 O3 1.4370(14) . ?
C6 C7 1.492(3) . ?
C6 C5 1.381(3) . ?
C6 C1 1.386(3) . ?
C14 C8 1.533(3) . ?
C15 C16 1.378(3) . ?
C15 C20 1.378(3) . ?
C8 C9 1.519(3) . ?
C8 C7 1.530(3) . ?
O1 C7 1.208(3) . ?
C16 C17 1.373(3) . ?
C20 C19 1.377(3) . ?
C9 C10 1.387(3) . ?
C9 C22 1.385(3) . ?
C10 C11 1.379(3) . ?
C11 C12 1.370(3) . ?
C5 C4 1.378(3) . ?
C12 C13 1.373(3) . ?
C22 C13 1.380(3) . ?
C1 C2 1.366(3) . ?
C19 C18 1.383(3) . ?
C3 C2 1.371(4) . ?
C3 C4 1.372(3) . ?
C17 C18 1.379(3) . ?
C18 C21 1.510(3) . ?
