#------------------------------------------------------------------------------
#$Date: 2024-05-05 03:52:58 +0300 (Sun, 05 May 2024) $
#$Revision: 291517 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/28/7132876.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_7132876
loop_
_publ_author_name
'Zhou, Xinlong'
'Jiang, Jingjing'
'Zhang, Min'
'Wu, Qingqing'
'Zhu, Keyong'
'Shi, Dongjie'
'Hou, Sensen'
'Zhao, Jingjing'
'Li, Pan'
_publ_section_title
;
 Dioxane promoted photochemical O-alkylation of 1,3-dicarbonyl
 compounds beyond carbene insertion into C-H and C-C bonds.
;
_journal_issue                   32
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4330
_journal_page_last               4333
_journal_paper_doi               10.1039/d4cc00778f
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C20 H22 O5 S'
_chemical_formula_sum            'C20 H22 O5 S'
_chemical_formula_weight         374.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-09-25 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.929(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.549(3)
_cell_length_b                   10.8252(14)
_cell_length_c                   17.856(3)
_cell_measurement_reflns_used    4488
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.511
_cell_measurement_theta_min      2.496
_cell_volume                     3807.3(10)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Helios multilayer optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20858
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.068
_diffrn_source_type              Microfocus
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.0479
_exptl_absorpt_correction_T_min  0.0252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1166 before and 0.0607 after correction. The Ratio of minimum to maximum transmission is 0.5261. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3739
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0416
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0387P)²+3.6759P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.1089
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2864
_reflns_number_total             3739
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc00778f2.cif
_cod_data_source_block           m12075_0m
_cod_depositor_comments
'Adding full bibliography for 7132875--7132877.cif.'
_cod_original_cell_volume        3807.4(9)
_cod_database_code               7132876
_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   0.982
_shelx_estimated_absorpt_t_min   0.977
_diffrn_source_source            'Incoatc Ius 3.0 '
_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:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.c Me refined with riding coordinates:
 C7(H7A,H7B,H7C)
2.d Aromatic/amide H refined with riding coordinates:
 C14(H14), C8(H8), C3(H3), C5(H5), C2(H2), C15(H15), C18(H18), C6(H6),
 C16(H16), C17(H17)
2.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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 0.61235(3) 0.88685(5) 0.75134(3) 0.03680(16) Uani 1 1 d . . . . .
O3 O 0.48944(7) 0.62546(13) 0.60746(9) 0.0369(3) Uani 1 1 d . . . . .
O4 O 0.49630(7) 0.71342(14) 0.47040(10) 0.0417(4) Uani 1 1 d . . . . .
O1 O 0.59368(8) 1.01528(14) 0.74173(10) 0.0455(4) Uani 1 1 d . . . . .
O5 O 0.41552(8) 0.85499(14) 0.45392(10) 0.0474(4) Uani 1 1 d . . . . .
O2 O 0.62540(8) 0.82751(16) 0.82863(10) 0.0479(4) Uani 1 1 d . . . . .
C13 C 0.37549(10) 0.60534(19) 0.50984(13) 0.0341(5) Uani 1 1 d . . . . .
C12 C 0.44775(10) 0.76550(19) 0.48733(13) 0.0348(5) Uani 1 1 d . . . . .
C11 C 0.43263(10) 0.69567(19) 0.55200(13) 0.0343(5) Uani 1 1 d . . . . .
H11 H 0.418085 0.755887 0.584203 0.041 Uiso 1 1 calc R . . . .
C4 C 0.68577(10) 0.86838(19) 0.73165(13) 0.0337(5) Uani 1 1 d . . . . .
C9 C 0.54147(10) 0.6866(2) 0.66726(13) 0.0354(5) Uani 1 1 d . . . . .
C14 C 0.31197(10) 0.6274(2) 0.50958(14) 0.0366(5) Uani 1 1 d . . . . .
H14 H 0.305173 0.696585 0.538134 0.044 Uiso 1 1 calc R . . . .
C8 C 0.54738(10) 0.8095(2) 0.67234(13) 0.0355(5) Uani 1 1 d . . . . .
H8 H 0.514345 0.857529 0.630592 0.043 Uiso 1 1 calc R . . . .
C3 C 0.73782(11) 0.7898(2) 0.77934(14) 0.0407(5) Uani 1 1 d . . . . .
H3 H 0.735196 0.747245 0.824503 0.049 Uiso 1 1 calc R . . . .
C5 C 0.68988(11) 0.9322(2) 0.66648(15) 0.0407(5) Uani 1 1 d . . . . .
H5 H 0.654569 0.986868 0.634498 0.049 Uiso 1 1 calc R . . . .
C2 C 0.79372(11) 0.7741(2) 0.76020(15) 0.0438(6) Uani 1 1 d . . . . .
H2 H 0.829406 0.720545 0.792748 0.053 Uiso 1 1 calc R . . . .
C15 C 0.25839(11) 0.5484(2) 0.46757(15) 0.0422(5) Uani 1 1 d . . . . .
H15 H 0.214682 0.564315 0.466474 0.051 Uiso 1 1 calc R . . . .
C1 C 0.79829(11) 0.8353(2) 0.69437(15) 0.0414(5) Uani 1 1 d . . . . .
C18 C 0.38550(12) 0.5020(2) 0.46974(16) 0.0445(6) Uani 1 1 d . . . . .
H18 H 0.429057 0.485828 0.470427 0.053 Uiso 1 1 calc R . . . .
C19 C 0.51089(13) 0.7706(2) 0.40481(16) 0.0480(6) Uani 1 1 d . . . . .
H19A H 0.468500 0.804772 0.362656 0.058 Uiso 1 1 calc R . . . .
H19B H 0.528449 0.707202 0.378447 0.058 Uiso 1 1 calc R . . . .
C6 C 0.74609(12) 0.9153(2) 0.64863(16) 0.0454(6) Uani 1 1 d . . . . .
H6 H 0.749110 0.959222 0.604171 0.054 Uiso 1 1 calc R . . . .
C16 C 0.26854(12) 0.4470(2) 0.42752(16) 0.0489(6) Uani 1 1 d . . . . .
H16 H 0.231723 0.393173 0.398707 0.059 Uiso 1 1 calc R . . . .
C10 C 0.58837(12) 0.5937(2) 0.72395(16) 0.0508(6) Uani 1 1 d . . . . .
H10A H 0.571644 0.569979 0.765404 0.076 Uiso 1 1 calc GR . . . .
H10B H 0.633849 0.629578 0.750928 0.076 Uiso 1 1 calc GR . . . .
H10C H 0.590428 0.520498 0.692726 0.076 Uiso 1 1 calc GR . . . .
C17 C 0.33208(13) 0.4229(2) 0.42894(17) 0.0527(6) Uani 1 1 d . . . . .
H17 H 0.338960 0.352080 0.401854 0.063 Uiso 1 1 calc R . . . .
C7 C 0.85771(13) 0.8138(2) 0.67157(19) 0.0560(7) Uani 1 1 d . . . . .
H7A H 0.852322 0.864605 0.623878 0.084 Uiso 1 1 calc R . . . .
H7B H 0.899935 0.836588 0.717790 0.084 Uiso 1 1 calc R . . . .
H7C H 0.859434 0.726437 0.658254 0.084 Uiso 1 1 calc R . . . .
C20 C 0.56226(14) 0.8719(2) 0.43828(18) 0.0578(7) Uani 1 1 d . . . . .
H20A H 0.570780 0.909849 0.393498 0.087 Uiso 1 1 calc GR . . . .
H20B H 0.604682 0.837605 0.478763 0.087 Uiso 1 1 calc GR . . . .
H20C H 0.544886 0.934608 0.464437 0.087 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
O1 S1 O2 118.76(11) . . ?
O1 S1 C4 108.40(10) . . ?
O1 S1 C8 105.87(10) . . ?
O2 S1 C4 107.29(10) . . ?
O2 S1 C8 109.91(10) . . ?
C8 S1 C4 105.93(10) . . ?
C9 O3 C11 118.79(16) . . ?
C12 O4 C19 116.54(17) . . ?
C14 C13 C11 119.55(19) . . ?
C14 C13 C18 119.7(2) . . ?
C18 C13 C11 120.74(19) . . ?
O4 C12 C11 113.15(17) . . ?
O5 C12 O4 125.5(2) . . ?
O5 C12 C11 121.28(19) . . ?
O3 C11 C13 107.13(16) . . ?
O3 C11 C12 113.58(16) . . ?
C13 C11 C12 108.97(17) . . ?
C3 C4 S1 120.85(17) . . ?
C5 C4 S1 118.55(16) . . ?
C5 C4 C3 120.6(2) . . ?
O3 C9 C10 108.62(18) . . ?
C8 C9 O3 124.13(19) . . ?
C8 C9 C10 127.2(2) . . ?
C15 C14 C13 119.9(2) . . ?
C9 C8 S1 123.75(17) . . ?
C2 C3 C4 119.3(2) . . ?
C6 C5 C4 119.1(2) . . ?
C1 C2 C3 121.1(2) . . ?
C16 C15 C14 120.0(2) . . ?
C2 C1 C6 118.4(2) . . ?
C2 C1 C7 121.0(2) . . ?
C6 C1 C7 120.6(2) . . ?
C17 C18 C13 120.0(2) . . ?
O4 C19 C20 110.7(2) . . ?
C5 C6 C1 121.5(2) . . ?
C15 C16 C17 120.4(2) . . ?
C18 C17 C16 120.0(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 O1 1.4381(17) . ?
S1 O2 1.4428(17) . ?
S1 C4 1.766(2) . ?
S1 C8 1.746(2) . ?
O3 C11 1.440(2) . ?
O3 C9 1.365(3) . ?
O4 C12 1.327(2) . ?
O4 C19 1.467(3) . ?
O5 C12 1.200(2) . ?
C13 C11 1.512(3) . ?
C13 C14 1.388(3) . ?
C13 C18 1.391(3) . ?
C12 C11 1.522(3) . ?
C4 C3 1.390(3) . ?
C4 C5 1.387(3) . ?
C9 C8 1.336(3) . ?
C9 C10 1.492(3) . ?
C14 C15 1.388(3) . ?
C3 C2 1.389(3) . ?
C5 C6 1.384(3) . ?
C2 C1 1.387(3) . ?
C15 C16 1.375(3) . ?
C1 C6 1.392(3) . ?
C1 C7 1.511(3) . ?
C18 C17 1.381(3) . ?
C19 C20 1.500(3) . ?
C16 C17 1.384(3) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C4 C3 C2 177.67(17) . . . . ?
S1 C4 C5 C6 -177.78(17) . . . . ?
O3 C9 C8 S1 177.39(16) . . . . ?
O4 C12 C11 O3 26.6(2) . . . . ?
O4 C12 C11 C13 -92.8(2) . . . . ?
O1 S1 C4 C3 139.58(18) . . . . ?
O1 S1 C4 C5 -41.7(2) . . . . ?
O1 S1 C8 C9 -170.27(19) . . . . ?
O5 C12 C11 O3 -156.67(19) . . . . ?
O5 C12 C11 C13 84.0(2) . . . . ?
O2 S1 C4 C3 10.2(2) . . . . ?
O2 S1 C4 C5 -171.05(17) . . . . ?
O2 S1 C8 C9 -40.9(2) . . . . ?
C13 C14 C15 C16 1.2(3) . . . . ?
C13 C18 C17 C16 0.4(4) . . . . ?
C12 O4 C19 C20 87.5(2) . . . . ?
C11 O3 C9 C8 -8.2(3) . . . . ?
C11 O3 C9 C10 171.41(18) . . . . ?
C11 C13 C14 C15 176.8(2) . . . . ?
C11 C13 C18 C17 -177.6(2) . . . . ?
C4 S1 C8 C9 74.7(2) . . . . ?
C4 C3 C2 C1 -0.1(3) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C9 O3 C11 C13 -164.08(17) . . . . ?
C9 O3 C11 C12 75.5(2) . . . . ?
C14 C13 C11 O3 127.9(2) . . . . ?
C14 C13 C11 C12 -108.9(2) . . . . ?
C14 C13 C18 C17 0.9(4) . . . . ?
C14 C15 C16 C17 0.1(4) . . . . ?
C8 S1 C4 C3 -107.18(19) . . . . ?
C8 S1 C4 C5 71.58(19) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C3 C2 C1 C6 1.4(3) . . . . ?
C3 C2 C1 C7 -177.4(2) . . . . ?
C5 C4 C3 C2 -1.1(3) . . . . ?
C2 C1 C6 C5 -1.4(3) . . . . ?
C15 C16 C17 C18 -1.0(4) . . . . ?
C18 C13 C11 O3 -53.6(3) . . . . ?
C18 C13 C11 C12 69.6(3) . . . . ?
C18 C13 C14 C15 -1.7(3) . . . . ?
C19 O4 C12 O5 -0.4(3) . . . . ?
C19 O4 C12 C11 176.18(18) . . . . ?
C10 C9 C8 S1 -2.2(3) . . . . ?
C7 C1 C6 C5 177.3(2) . . . . ?
