#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/39/1553972.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_1553972
loop_
_publ_author_name
'Wang, Shi-Meng'
'Li, Chen'
'Leng, Jing'
'Bukhari, Syed Nasir Abbas'
'Qin, Hua-Li'
_publ_section_title
;
 Rhodium(iii)-catalyzed Oxidative Coupling of N-Methoxybenzamides and
 Ethenesulfonyl fluoride: a C--H Bond Activation Strategy for the
 Preparation of 2-Aryl ethenesulfonyl fluorides and Sulfonyl fluoride
 Substituted γ-Lactams
;
_journal_issue                   9
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1411
_journal_paper_doi               10.1039/C7QO01128H
_journal_volume                  5
_journal_year                    2018
_chemical_formula_sum            'C15 H11 F O5 S'
_chemical_formula_weight         322.30
_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
_audit_update_record
;
2017-10-12 deposited with the CCDC.
2018-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.112(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6492(9)
_cell_length_b                   6.7929(8)
_cell_length_c                   25.645(3)
_cell_measurement_reflns_used    2743
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.763
_cell_measurement_theta_min      2.675
_cell_volume                     1491.6(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0586
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            2570
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_T_max  0.9182
_exptl_absorpt_correction_T_min  0.9029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2570
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0813
_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)+(0.1098P)²+1.9743P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2160
_refine_ls_wR_factor_ref         0.2291
_reflns_number_gt                1863
_reflns_number_total             2570
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7qo01128h2.cif
_cod_data_source_block           170906f
_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/RSC/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_cell_volume        1491.7(3)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1553972
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
O4 O 0.7330(6) 0.7871(9) 1.10163(18) 0.0999(19) Uani 1 1 d .
O1 O 0.7415(4) 0.9537(5) 0.99128(14) 0.0530(9) Uani 1 1 d .
O2 O 0.8862(4) 1.2054(5) 0.96973(15) 0.0605(10) Uani 1 1 d .
O3 O 0.8863(7) 0.4339(6) 0.81989(18) 0.0914(16) Uani 1 1 d .
F1 F 0.5021(5) 0.6488(8) 1.05511(16) 0.1036(15) Uani 1 1 d .
O5 O 0.7021(7) 0.4405(9) 1.0990(2) 0.113(2) Uani 1 1 d .
S1 S 0.66303(16) 0.6233(2) 1.07018(5) 0.0583(5) Uani 1 1 d .
C1 C 0.8385(6) 1.0420(7) 0.95994(19) 0.0457(11) Uani 1 1 d .
C2 C 0.8645(5) 0.9065(7) 0.91889(19) 0.0443(11) Uani 1 1 d .
C3 C 0.9538(6) 0.9262(8) 0.8782(2) 0.0551(13) Uani 1 1 d .
H3 H 1.0065 1.0432 0.8739 0.066 Uiso 1 1 calc R
C4 C 0.9636(7) 0.7730(9) 0.8445(2) 0.0609(15) Uani 1 1 d .
H4 H 1.0250 0.7832 0.8177 0.073 Uiso 1 1 calc R
C5 C 0.8796(7) 0.5988(8) 0.8509(2) 0.0588(14) Uani 1 1 d .
C6 C 0.7901(6) 0.5765(7) 0.89046(19) 0.0527(13) Uani 1 1 d .
H6 H 0.7360 0.4604 0.8945 0.063 Uiso 1 1 calc R
C7 C 0.7837(5) 0.7350(7) 0.92431(17) 0.0428(11) Uani 1 1 d .
C8 C 0.7029(6) 0.7553(7) 0.97240(18) 0.0448(11) Uani 1 1 d .
H8 H 0.5897 0.7417 0.9627 0.054 Uiso 1 1 calc R
C9 C 0.7619(6) 0.6089(7) 1.01482(18) 0.0462(11) Uani 1 1 d .
H9A H 0.8724 0.6317 1.0259 0.055 Uiso 1 1 calc R
H9B H 0.7502 0.4770 1.0003 0.055 Uiso 1 1 calc R
C10 C 0.9485(7) 0.4397(9) 0.7727(2) 0.0604(15) Uani 1 1 d .
C11 C 0.8937(8) 0.5588(10) 0.7321(3) 0.0796(19) Uani 1 1 d .
H11 H 0.8142 0.6482 0.7355 0.095 Uiso 1 1 calc R
C12 C 0.9566(11) 0.5472(12) 0.6850(3) 0.091(2) Uani 1 1 d .
H12 H 0.9224 0.6326 0.6574 0.110 Uiso 1 1 calc R
C13 C 1.0662(11) 0.4130(12) 0.6797(3) 0.093(2) Uani 1 1 d .
H13 H 1.1057 0.4024 0.6479 0.111 Uiso 1 1 calc R
C14 C 1.1203(10) 0.2925(12) 0.7202(3) 0.097(3) Uani 1 1 d .
H14 H 1.1959 0.1987 0.7160 0.117 Uiso 1 1 calc R
C15 C 1.0641(8) 0.3080(10) 0.7676(2) 0.0766(18) Uani 1 1 d .
H15 H 1.1047 0.2292 0.7959 0.092 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'
F F 0.0171 0.0103 '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
C1 O1 C8 109.8(4)
C5 O3 C10 122.0(4)
F1 S1 O4 112.2(3)
F1 S1 O5 113.2(3)
O4 S1 O5 108.7(4)
F1 S1 C9 111.2(2)
O4 S1 C9 106.2(3)
O5 S1 C9 104.9(3)
O2 C1 O1 120.0(5)
O2 C1 C2 131.3(5)
O1 C1 C2 108.6(4)
C7 C2 C3 120.1(4)
C7 C2 C1 109.5(4)
C3 C2 C1 130.4(4)
C4 C3 C2 119.5(5)
C4 C3 H3 120.2
C2 C3 H3 120.2
C3 C4 C5 119.3(5)
C3 C4 H4 120.3
C5 C4 H4 120.3
C6 C5 O3 114.3(4)
C6 C5 C4 122.2(5)
O3 C5 C4 123.4(4)
C5 C6 C7 117.0(4)
C5 C6 H6 121.5
C7 C6 H6 121.5
C2 C7 C6 121.9(4)
C2 C7 C8 107.8(4)
C6 C7 C8 130.2(4)
O1 C8 C7 104.2(4)
O1 C8 C9 109.4(4)
C7 C8 C9 112.4(4)
O1 C8 H8 110.2
C7 C8 H8 110.2
C9 C8 H8 110.2
C8 C9 S1 113.0(3)
C8 C9 H9A 109.0
S1 C9 H9A 109.0
C8 C9 H9B 109.0
S1 C9 H9B 109.0
H9A C9 H9B 107.8
C11 C10 C15 120.1(5)
C11 C10 O3 123.4(6)
C15 C10 O3 116.4(6)
C10 C11 C12 119.7(7)
C10 C11 H11 120.1
C12 C11 H11 120.1
C13 C12 C11 119.7(7)
C13 C12 H12 120.1
C11 C12 H12 120.1
C12 C13 C14 120.5(6)
C12 C13 H13 119.7
C14 C13 H13 119.7
C13 C14 C15 120.3(7)
C13 C14 H14 119.8
C15 C14 H14 119.8
C10 C15 C14 119.4(7)
C10 C15 H15 120.3
C14 C15 H15 120.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 S1 1.455(4)
O1 C1 1.378(6)
O1 C8 1.455(6)
O2 C1 1.198(6)
O3 C5 1.379(6)
O3 C10 1.392(6)
F1 S1 1.402(4)
O5 S1 1.461(5)
S1 C9 1.760(5)
C1 C2 1.440(7)
C2 C7 1.376(6)
C2 C3 1.391(7)
C3 C4 1.361(8)
C3 H3 0.9300
C4 C5 1.410(8)
C4 H4 0.9300
C5 C6 1.370(7)
C6 C7 1.389(7)
C6 H6 0.9300
C7 C8 1.507(6)
C8 C9 1.508(7)
C8 H8 0.9800
C9 H9A 0.9700
C9 H9B 0.9700
C10 C11 1.351(9)
C10 C15 1.362(9)
C11 C12 1.395(10)
C11 H11 0.9300
C12 C13 1.336(11)
C12 H12 0.9300
C13 C14 1.353(11)
C13 H13 0.9300
C14 C15 1.375(9)
C14 H14 0.9300
C15 H15 0.9300
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
C8 O1 C1 O2 -178.5(4)
C8 O1 C1 C2 1.1(5)
O2 C1 C2 C7 179.9(5)
O1 C1 C2 C7 0.3(5)
O2 C1 C2 C3 0.0(9)
O1 C1 C2 C3 -179.5(5)
C7 C2 C3 C4 -1.6(8)
C1 C2 C3 C4 178.3(5)
C2 C3 C4 C5 1.6(9)
C10 O3 C5 C6 168.6(6)
C10 O3 C5 C4 -14.5(10)
C3 C4 C5 C6 -1.2(10)
C3 C4 C5 O3 -177.8(6)
O3 C5 C6 C7 177.6(5)
C4 C5 C6 C7 0.7(9)
C3 C2 C7 C6 1.1(8)
C1 C2 C7 C6 -178.8(5)
C3 C2 C7 C8 178.3(5)
C1 C2 C7 C8 -1.6(5)
C5 C6 C7 C2 -0.6(8)
C5 C6 C7 C8 -177.1(5)
C1 O1 C8 C7 -2.0(5)
C1 O1 C8 C9 118.5(4)
C2 C7 C8 O1 2.1(5)
C6 C7 C8 O1 179.0(5)
C2 C7 C8 C9 -116.2(5)
C6 C7 C8 C9 60.7(7)
O1 C8 C9 S1 67.3(4)
C7 C8 C9 S1 -177.4(3)
F1 S1 C9 C8 41.4(5)
O4 S1 C9 C8 -80.8(5)
O5 S1 C9 C8 164.2(4)
C5 O3 C10 C11 -58.2(9)
C5 O3 C10 C15 125.8(7)
C15 C10 C11 C12 -0.4(10)
O3 C10 C11 C12 -176.2(6)
C10 C11 C12 C13 2.7(12)
C11 C12 C13 C14 -2.1(13)
C12 C13 C14 C15 -0.7(13)
C11 C10 C15 C14 -2.3(11)
O3 C10 C15 C14 173.7(7)
C13 C14 C15 C10 2.9(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168304178
