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#$Date: 2021-08-03 22:38:24 +0300 (Tue, 03 Aug 2021) $
#$Revision: 267917 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/89/4518943.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_4518943
loop_
_publ_author_name
'Xia, Liwen'
'Fan, Wenjing'
'Yuan, Xiang-Ai'
'Yu, Shouyun'
_publ_section_title
;
 Photoredox-Catalyzed Stereoselective Synthesis of C-Nucleoside Analogues
 from Glycosyl Bromides and Heteroarenes
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              9397
_journal_page_last               9406
_journal_paper_doi               10.1021/acscatal.1c02088
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_sum            'C13 H15 N O5 S'
_chemical_formula_weight         297.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6530(4)
_cell_length_b                   6.9677(4)
_cell_length_c                   27.9699(13)
_cell_measurement_reflns_used    3578
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      54.807
_cell_measurement_theta_min      6.026
_cell_volume                     1296.58(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            6198
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.913
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorleee
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
; 
 Flack x determined using 851 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2538
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0300
_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)+(0.0313P)²+0.2108P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0721
_reflns_Friedel_coverage         0.677
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                2308
_reflns_number_total             2538
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c02088_si_002.cif
_cod_data_source_block           mo_d8v21076_0m
_cod_database_code               4518943
_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_min   0.953
_shelx_estimated_absorpt_t_max   0.974
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_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 0.40156(11) 0.45387(12) 0.57608(3) 0.0476(2) Uani 1 1 d . . . . .
O1 O 0.5291(2) 0.4236(2) 0.67992(6) 0.0307(4) Uani 1 1 d . . . . .
O2 O 0.8269(3) 0.3270(3) 0.75134(6) 0.0417(5) Uani 1 1 d . . . . .
H2 H 0.8320 0.2273 0.7675 0.063 Uiso 1 1 calc R U . . .
O3 O 1.1393(3) 0.4917(3) 0.70135(8) 0.0540(6) Uani 1 1 d . . . . .
H3 H 1.2330 0.4268 0.6903 0.081 Uiso 1 1 calc R U . . .
O4 O 0.9201(3) 0.7819(3) 0.65294(6) 0.0438(5) Uani 1 1 d . . . . .
H4 H 0.9307 0.7581 0.6240 0.066 Uiso 1 1 calc R U . . .
O5 O 0.3429(3) 0.0668(3) 0.67832(7) 0.0560(6) Uani 1 1 d . . . . .
H5 H 0.2662 -0.0010 0.6945 0.084 Uiso 1 1 calc R U . . .
N1 N 0.7660(3) 0.5849(3) 0.57379(7) 0.0384(5) Uani 1 1 d . . . . .
C1 C 0.5180(5) 0.4697(4) 0.52090(10) 0.0465(7) Uani 1 1 d . . . . .
C2 C 0.4447(6) 0.4206(4) 0.47579(11) 0.0634(10) Uani 1 1 d . . . . .
H2A H 0.3146 0.3702 0.4720 0.076 Uiso 1 1 calc R U . . .
C3 C 0.5690(7) 0.4486(5) 0.43709(11) 0.0726(12) Uani 1 1 d . . . . .
H3A H 0.5224 0.4178 0.4063 0.087 Uiso 1 1 calc R U . . .
C4 C 0.7610(8) 0.5209(4) 0.44258(11) 0.0706(11) Uani 1 1 d . . . . .
H4A H 0.8420 0.5383 0.4154 0.085 Uiso 1 1 calc R U . . .
C5 C 0.8372(6) 0.5682(4) 0.48699(9) 0.0564(8) Uani 1 1 d . . . . .
H5A H 0.9685 0.6161 0.4904 0.068 Uiso 1 1 calc R U . . .
C6 C 0.7119(5) 0.5424(4) 0.52660(9) 0.0427(6) Uani 1 1 d . . . . .
C7 C 0.6175(4) 0.5468(3) 0.60222(8) 0.0339(5) Uani 1 1 d . . . . .
C8 C 0.6199(3) 0.5811(3) 0.65561(8) 0.0308(5) Uani 1 1 d . . . . .
H8 H 0.5349 0.6951 0.6618 0.037 Uiso 1 1 calc R U . . .
C9 C 0.8284(4) 0.6242(3) 0.67643(9) 0.0318(5) Uani 1 1 d . . . . .
H9 H 0.8080 0.6627 0.7102 0.038 Uiso 1 1 calc R U . . .
C10 C 0.9579(3) 0.4442(4) 0.67708(9) 0.0353(6) Uani 1 1 d . . . . .
H10 H 0.9895 0.4060 0.6438 0.042 Uiso 1 1 calc R U . . .
C11 C 0.8488(4) 0.2802(4) 0.70205(8) 0.0321(6) Uani 1 1 d . . . . .
H11 H 0.9297 0.1616 0.6991 0.039 Uiso 1 1 calc R U . . .
C12 C 0.6449(3) 0.2489(3) 0.67876(8) 0.0286(5) Uani 1 1 d . . . . .
H12 H 0.6647 0.2091 0.6451 0.034 Uiso 1 1 calc R U . . .
C13 C 0.5224(4) 0.0999(4) 0.70419(9) 0.0364(6) Uani 1 1 d . . . . .
H13A H 0.5993 -0.0196 0.7068 0.044 Uiso 1 1 calc R U . . .
H13B H 0.4902 0.1442 0.7366 0.044 Uiso 1 1 calc R U . . .
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'
N N 0.0061 0.0033 '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
C1 S1 C7 88.94(13) . . ?
C8 O1 C12 114.42(15) . . ?
C11 O2 H2 109.5 . . ?
C10 O3 H3 109.5 . . ?
C9 O4 H4 109.5 . . ?
C13 O5 H5 109.5 . . ?
C7 N1 C6 109.8(2) . . ?
C6 C1 C2 121.0(3) . . ?
C6 C1 S1 109.6(2) . . ?
C2 C1 S1 129.4(3) . . ?
C3 C2 C1 117.8(4) . . ?
C3 C2 H2A 121.1 . . ?
C1 C2 H2A 121.1 . . ?
C2 C3 C4 121.3(3) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C3 C4 C5 121.7(3) . . ?
C3 C4 H4A 119.1 . . ?
C5 C4 H4A 119.1 . . ?
C4 C5 C6 117.6(4) . . ?
C4 C5 H5A 121.2 . . ?
C6 C5 H5A 121.2 . . ?
C1 C6 C5 120.5(3) . . ?
C1 C6 N1 115.0(2) . . ?
C5 C6 N1 124.5(3) . . ?
N1 C7 C8 124.4(2) . . ?
N1 C7 S1 116.68(18) . . ?
C8 C7 S1 118.89(17) . . ?
O1 C8 C7 110.17(19) . . ?
O1 C8 C9 110.65(18) . . ?
C7 C8 C9 114.53(19) . . ?
O1 C8 H8 107.0 . . ?
C7 C8 H8 107.0 . . ?
C9 C8 H8 107.0 . . ?
O4 C9 C10 113.6(2) . . ?
O4 C9 C8 111.4(2) . . ?
C10 C9 C8 110.8(2) . . ?
O4 C9 H9 106.9 . . ?
C10 C9 H9 106.9 . . ?
C8 C9 H9 106.9 . . ?
O3 C10 C9 107.1(2) . . ?
O3 C10 C11 111.1(2) . . ?
C9 C10 C11 110.74(18) . . ?
O3 C10 H10 109.3 . . ?
C9 C10 H10 109.3 . . ?
C11 C10 H10 109.3 . . ?
O2 C11 C12 110.87(19) . . ?
O2 C11 C10 108.7(2) . . ?
C12 C11 C10 109.65(19) . . ?
O2 C11 H11 109.2 . . ?
C12 C11 H11 109.2 . . ?
C10 C11 H11 109.2 . . ?
O1 C12 C13 106.46(18) . . ?
O1 C12 C11 110.25(19) . . ?
C13 C12 C11 112.4(2) . . ?
O1 C12 H12 109.2 . . ?
C13 C12 H12 109.2 . . ?
C11 C12 H12 109.2 . . ?
O5 C13 C12 109.2(2) . . ?
O5 C13 H13A 109.8 . . ?
C12 C13 H13A 109.8 . . ?
O5 C13 H13B 109.8 . . ?
C12 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?
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 C1 1.731(3) . ?
S1 C7 1.737(2) . ?
O1 C8 1.425(3) . ?
O1 C12 1.441(3) . ?
O2 C11 1.424(3) . ?
O2 H2 0.8300 . ?
O3 C10 1.423(3) . ?
O3 H3 0.8300 . ?
O4 C9 1.418(3) . ?
O4 H4 0.8300 . ?
O5 C13 1.415(3) . ?
O5 H5 0.8300 . ?
N1 C7 1.296(3) . ?
N1 C6 1.400(3) . ?
C1 C6 1.395(4) . ?
C1 C2 1.395(4) . ?
C2 C3 1.376(5) . ?
C2 H2A 0.9400 . ?
C3 C4 1.382(6) . ?
C3 H3A 0.9400 . ?
C4 C5 1.382(4) . ?
C4 H4A 0.9400 . ?
C5 C6 1.398(4) . ?
C5 H5A 0.9400 . ?
C7 C8 1.513(3) . ?
C8 C9 1.535(3) . ?
C8 H8 0.9900 . ?
C9 C10 1.521(4) . ?
C9 H9 0.9900 . ?
C10 C11 1.523(4) . ?
C10 H10 0.9900 . ?
C11 C12 1.520(3) . ?
C11 H11 0.9900 . ?
C12 C13 1.500(3) . ?
C12 H12 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5 O2 0.83 2.03 2.818(2) 158.6 3_646
O4 H4 N1 0.83 2.15 2.799(3) 134.9 .
O3 H3 O5 0.83 2.63 3.319(3) 140.7 1_655
O3 H3 O1 0.83 1.99 2.704(2) 143.5 1_655
O2 H2 O3 0.83 1.87 2.695(2) 173.7 3_746
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
C7 S1 C1 C6 0.5(2) . . . . ?
C7 S1 C1 C2 -179.9(3) . . . . ?
C6 C1 C2 C3 -0.8(4) . . . . ?
S1 C1 C2 C3 179.7(2) . . . . ?
C1 C2 C3 C4 0.7(5) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C3 C4 C5 C6 -0.7(5) . . . . ?
C2 C1 C6 C5 0.2(4) . . . . ?
S1 C1 C6 C5 179.8(2) . . . . ?
C2 C1 C6 N1 -179.8(3) . . . . ?
S1 C1 C6 N1 -0.2(3) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
C4 C5 C6 N1 -179.5(3) . . . . ?
C7 N1 C6 C1 -0.5(3) . . . . ?
C7 N1 C6 C5 179.5(3) . . . . ?
C6 N1 C7 C8 -177.9(2) . . . . ?
C6 N1 C7 S1 0.9(3) . . . . ?
C1 S1 C7 N1 -0.9(2) . . . . ?
C1 S1 C7 C8 178.0(2) . . . . ?
C12 O1 C8 C7 70.0(2) . . . . ?
C12 O1 C8 C9 -57.7(2) . . . . ?
N1 C7 C8 O1 -138.4(2) . . . . ?
S1 C7 C8 O1 42.8(3) . . . . ?
N1 C7 C8 C9 -12.9(3) . . . . ?
S1 C7 C8 C9 168.28(18) . . . . ?
O1 C8 C9 O4 -179.42(18) . . . . ?
C7 C8 C9 O4 55.3(3) . . . . ?
O1 C8 C9 C10 53.0(2) . . . . ?
C7 C8 C9 C10 -72.2(3) . . . . ?
O4 C9 C10 O3 59.7(3) . . . . ?
C8 C9 C10 O3 -173.98(19) . . . . ?
O4 C9 C10 C11 -179.04(19) . . . . ?
C8 C9 C10 C11 -52.7(3) . . . . ?
O3 C10 C11 O2 52.1(2) . . . . ?
C9 C10 C11 O2 -66.8(2) . . . . ?
O3 C10 C11 C12 173.43(18) . . . . ?
C9 C10 C11 C12 54.6(3) . . . . ?
C8 O1 C12 C13 -177.80(18) . . . . ?
C8 O1 C12 C11 60.0(2) . . . . ?
O2 C11 C12 O1 63.4(2) . . . . ?
C10 C11 C12 O1 -56.7(2) . . . . ?
O2 C11 C12 C13 -55.2(3) . . . . ?
C10 C11 C12 C13 -175.32(19) . . . . ?
O1 C12 C13 O5 64.1(3) . . . . ?
C11 C12 C13 O5 -175.1(2) . . . . ?
