#------------------------------------------------------------------------------
#$Date: 2020-06-05 14:32:24 +0300 (Fri, 05 Jun 2020) $
#$Revision: 252931 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/75/7157501.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_7157501
loop_
_publ_author_name
'Liu, Jing'
'Wang, Shi-Meng'
'Qin, Hua-Li'
_publ_section_title
;
 Light-induced [2 + 2] cycloadditions for the construction of
 cyclobutane-fused pyridinyl sulfonyl fluorides.
;
_journal_issue                   21
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4019
_journal_page_last               4023
_journal_paper_doi               10.1039/d0ob00814a
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C8 H12 F N O4 S'
_chemical_formula_weight         237.25
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2019-09-16 deposited with the CCDC.	2020-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                79.6510(10)
_cell_angle_beta                 81.793(2)
_cell_angle_gamma                80.0050(10)
_cell_formula_units_Z            2
_cell_length_a                   6.9928(5)
_cell_length_b                   7.7011(6)
_cell_length_c                   10.3093(9)
_cell_measurement_reflns_used    1609
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.209
_cell_measurement_theta_min      2.732
_cell_volume                     534.28(7)
_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  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2675
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.72
_exptl_absorpt_coefficient_mu    0.312
_exptl_absorpt_correction_T_max  0.8961
_exptl_absorpt_correction_T_min  0.8648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1849
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0402
_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)+(0.0512P)²+0.2393P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1132
_reflns_number_gt                1528
_reflns_number_total             1849
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0ob00814a2.cif
_cod_data_source_block           190909f
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157501.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7157501
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.7129(3) 0.0568(3) 0.0332(2) 0.0935(6) Uani 1 1 d . . .
N1 N 0.0590(3) 0.4696(2) 0.27935(18) 0.0401(4) Uani 1 1 d . . .
O1 O -0.2202(2) 0.4403(2) 0.41821(17) 0.0525(5) Uani 1 1 d . . .
O2 O 0.8158(3) 0.0726(3) 0.2416(2) 0.0657(5) Uani 1 1 d . . .
O3 O 0.7016(3) 0.3427(2) 0.09646(19) 0.0633(5) Uani 1 1 d . . .
O4 O 0.5485(3) 0.2835(2) 0.6467(2) 0.0661(5) Uani 1 1 d . . .
H4C H 0.6322 0.3163 0.5828 0.079 Uiso 1 1 d R . .
H4D H 0.4425 0.3556 0.6390 0.079 Uiso 1 1 d R . .
S1 S 0.68363(9) 0.15978(8) 0.14579(7) 0.0518(2) Uani 1 1 d . . .
C1 C -0.0449(3) 0.3851(3) 0.3837(2) 0.0385(5) Uani 1 1 d . . .
C2 C 0.0566(3) 0.2236(3) 0.4617(2) 0.0429(5) Uani 1 1 d . . .
H2 H -0.0170 0.1591 0.5298 0.052 Uiso 1 1 calc R . .
C3 C 0.2460(3) 0.1661(3) 0.4399(2) 0.0447(5) Uani 1 1 d . . .
H3 H 0.3007 0.0657 0.4946 0.054 Uiso 1 1 calc R . .
C4 C 0.3743(3) 0.2574(3) 0.3305(2) 0.0377(5) Uani 1 1 d . . .
H4 H 0.4808 0.3017 0.3607 0.045 Uiso 1 1 calc R . .
C5 C 0.2583(3) 0.3964(3) 0.2316(2) 0.0378(5) Uani 1 1 d . . .
H5 H 0.3336 0.4935 0.1938 0.045 Uiso 1 1 calc R . .
C6 C 0.2848(3) 0.2596(3) 0.1353(2) 0.0464(6) Uani 1 1 d . . .
H6A H 0.3343 0.3052 0.0451 0.056 Uiso 1 1 calc R . .
H6B H 0.1697 0.2044 0.1369 0.056 Uiso 1 1 calc R . .
C7 C 0.4427(3) 0.1419(3) 0.2169(2) 0.0406(5) Uani 1 1 d . . .
H7 H 0.4195 0.0179 0.2434 0.049 Uiso 1 1 calc R . .
C8 C -0.0317(4) 0.6313(3) 0.1995(3) 0.0612(7) Uani 1 1 d . . .
H8A H -0.1577 0.6720 0.2436 0.092 Uiso 1 1 calc R . .
H8B H -0.0468 0.6055 0.1141 0.092 Uiso 1 1 calc R . .
H8C H 0.0496 0.7225 0.1883 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'
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'
F F 0.0171 0.0103 '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 N1 C5 122.35(18) . . ?
C1 N1 C8 120.51(19) . . ?
C5 N1 C8 116.83(18) . . ?
H4C O4 H4D 108.0 . . ?
O3 S1 O2 114.53(12) . . ?
O3 S1 F1 109.86(13) . . ?
O2 S1 F1 109.00(13) . . ?
O3 S1 C7 110.03(11) . . ?
O2 S1 C7 108.84(11) . . ?
F1 S1 C7 104.05(11) . . ?
O1 C1 N1 122.4(2) . . ?
O1 C1 C2 119.8(2) . . ?
N1 C1 C2 117.81(19) . . ?
C3 C2 C1 123.6(2) . . ?
C3 C2 H2 118.2 . . ?
C1 C2 H2 118.2 . . ?
C2 C3 C4 122.0(2) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 112.97(18) . . ?
C3 C4 C7 111.36(17) . . ?
C5 C4 C7 88.32(15) . . ?
C3 C4 H4 113.9 . . ?
C5 C4 H4 113.9 . . ?
C7 C4 H4 113.9 . . ?
N1 C5 C4 117.18(17) . . ?
N1 C5 C6 117.73(18) . . ?
C4 C5 C6 90.17(16) . . ?
N1 C5 H5 110.1 . . ?
C4 C5 H5 110.1 . . ?
C6 C5 H5 110.1 . . ?
C5 C6 C7 89.07(16) . . ?
C5 C6 H6A 113.8 . . ?
C7 C6 H6A 113.8 . . ?
C5 C6 H6B 113.8 . . ?
C7 C6 H6B 113.8 . . ?
H6A C6 H6B 111.0 . . ?
C6 C7 C4 89.21(16) . . ?
C6 C7 S1 114.04(16) . . ?
C4 C7 S1 112.42(14) . . ?
C6 C7 H7 113.0 . . ?
C4 C7 H7 113.0 . . ?
S1 C7 H7 113.0 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
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
F1 S1 1.4917(19) . ?
N1 C1 1.341(3) . ?
N1 C5 1.461(3) . ?
N1 C8 1.462(3) . ?
O1 C1 1.248(3) . ?
O2 S1 1.4451(19) . ?
O3 S1 1.4297(18) . ?
O4 H4C 0.8500 . ?
O4 H4D 0.8500 . ?
S1 C7 1.757(2) . ?
C1 C2 1.481(3) . ?
C2 C3 1.322(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.489(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.544(3) . ?
C4 C7 1.568(3) . ?
C4 H4 0.9800 . ?
C5 C6 1.544(3) . ?
C5 H5 0.9800 . ?
C6 C7 1.547(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 O1 -174.2(2) . . . . ?
C8 N1 C1 O1 -0.9(3) . . . . ?
C5 N1 C1 C2 7.6(3) . . . . ?
C8 N1 C1 C2 -179.1(2) . . . . ?
O1 C1 C2 C3 -173.2(2) . . . . ?
N1 C1 C2 C3 5.0(3) . . . . ?
C1 C2 C3 C4 -1.9(4) . . . . ?
C2 C3 C4 C5 -11.8(3) . . . . ?
C2 C3 C4 C7 -109.3(2) . . . . ?
C1 N1 C5 C4 -21.6(3) . . . . ?
C8 N1 C5 C4 164.8(2) . . . . ?
C1 N1 C5 C6 84.2(3) . . . . ?
C8 N1 C5 C6 -89.4(3) . . . . ?
C3 C4 C5 N1 22.6(3) . . . . ?
C7 C4 C5 N1 135.16(18) . . . . ?
C3 C4 C5 C6 -99.0(2) . . . . ?
C7 C4 C5 C6 13.51(15) . . . . ?
N1 C5 C6 C7 -134.87(19) . . . . ?
C4 C5 C6 C7 -13.69(16) . . . . ?
C5 C6 C7 C4 13.49(16) . . . . ?
C5 C6 C7 S1 -100.81(16) . . . . ?
C3 C4 C7 C6 100.6(2) . . . . ?
C5 C4 C7 C6 -13.49(16) . . . . ?
C3 C4 C7 S1 -143.64(17) . . . . ?
C5 C4 C7 S1 102.30(16) . . . . ?
O3 S1 C7 C6 42.77(19) . . . . ?
O2 S1 C7 C6 169.02(16) . . . . ?
F1 S1 C7 C6 -74.87(18) . . . . ?
O3 S1 C7 C4 -56.89(18) . . . . ?
O2 S1 C7 C4 69.36(18) . . . . ?
F1 S1 C7 C4 -174.53(16) . . . . ?
