#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:24:11 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268918 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158124.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_7158124
loop_
_publ_author_name
'Zhang, Zai-Wei'
'Rakesh, K. P.'
'Liu, Jing'
'Qin, Hua-Li'
'Tang, Haolin'
_publ_section_title
;
 A general approach to nitrile- and sulfonyl fluoride-substituted
 cyclopropanes.
;
_journal_issue                   27
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6021
_journal_page_last               6024
_journal_paper_doi               10.1039/d1ob01043c
_journal_volume                  19
_journal_year                    2021
_chemical_formula_sum            'C16 H12 F N O2 S'
_chemical_formula_weight         301.33
_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
;
2021-03-13 deposited with the CCDC.	2021-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                95.348(2)
_cell_angle_beta                 100.866(3)
_cell_angle_gamma                105.796(3)
_cell_formula_units_Z            2
_cell_length_a                   6.4301(5)
_cell_length_b                   7.7504(6)
_cell_length_c                   14.9740(12)
_cell_measurement_reflns_used    861
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.945
_cell_measurement_theta_min      2.764
_cell_volume                     696.89(10)
_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 0.972
_diffrn_measured_fraction_theta_max 0.972
_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  0.0425
_diffrn_reflns_av_sigmaI/netI    0.1046
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3439
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.76
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.9569
_exptl_absorpt_correction_T_min  0.8971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.914
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1269
_refine_ls_R_factor_gt           0.0836
_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)+(0.1464P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2110
_refine_ls_wR_factor_ref         0.2441
_reflns_number_gt                1515
_reflns_number_total             2396
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ob01043c2.cif
_cod_data_source_block           181206b
_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 7158124--7158125.cif.
;
_cod_original_cell_volume        696.89(9)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7158124
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 -0.4880(5) 0.3883(5) 0.1216(2) 0.0681(10) Uani 1 1 d . . .
N1 N 0.1313(9) -0.0709(8) 0.1255(3) 0.0759(16) Uani 1 1 d . . .
O1 O -0.2395(6) 0.4635(5) 0.0232(3) 0.0694(13) Uani 1 1 d . . .
O2 O -0.5384(6) 0.1829(5) -0.0119(2) 0.0584(11) Uani 1 1 d . . .
S1 S -0.37075(19) 0.31752(17) 0.05288(9) 0.0459(5) Uani 1 1 d . . .
C1 C 0.0743(8) 0.0539(8) 0.1164(3) 0.0490(13) Uani 1 1 d . . .
C2 C 0.0094(7) 0.2146(7) 0.1038(3) 0.0415(12) Uani 1 1 d . . .
H2 H 0.0473 0.2725 0.0511 0.050 Uiso 1 1 calc R . .
C3 C -0.2075(7) 0.2199(6) 0.1261(3) 0.0368(11) Uani 1 1 d . . .
H3 H -0.2866 0.1153 0.1512 0.044 Uiso 1 1 calc R . .
C4 C 0.0029(7) 0.3389(6) 0.1862(3) 0.0392(12) Uani 1 1 d . . .
H4 H 0.0358 0.4673 0.1789 0.047 Uiso 1 1 calc R . .
C5 C 0.0749(7) 0.3058(6) 0.2823(3) 0.0384(11) Uani 1 1 d . . .
C6 C -0.0752(8) 0.2516(7) 0.3366(4) 0.0483(13) Uani 1 1 d . . .
H6 H -0.2258 0.2293 0.3121 0.058 Uiso 1 1 calc R . .
C7 C -0.0049(8) 0.2298(7) 0.4270(4) 0.0479(13) Uani 1 1 d . . .
H7 H -0.1092 0.1953 0.4624 0.057 Uiso 1 1 calc R . .
C8 C 0.2168(7) 0.2579(6) 0.4658(3) 0.0391(11) Uani 1 1 d . . .
C9 C 0.3654(8) 0.3122(7) 0.4092(3) 0.0465(13) Uani 1 1 d . . .
H9 H 0.5162 0.3334 0.4328 0.056 Uiso 1 1 calc R . .
C10 C 0.2957(7) 0.3347(7) 0.3210(3) 0.0447(12) Uani 1 1 d . . .
H10 H 0.3998 0.3706 0.2856 0.054 Uiso 1 1 calc R . .
C11 C 0.2924(8) 0.2382(6) 0.5628(3) 0.0395(11) Uani 1 1 d . . .
C12 C 0.1815(9) 0.2735(7) 0.6304(4) 0.0519(14) Uani 1 1 d . . .
H12 H 0.0541 0.3089 0.6139 0.062 Uiso 1 1 calc R . .
C13 C 0.2544(10) 0.2577(8) 0.7209(4) 0.0590(16) Uani 1 1 d . . .
H13 H 0.1764 0.2815 0.7646 0.071 Uiso 1 1 calc R . .
C14 C 0.4416(10) 0.2070(8) 0.7462(4) 0.0606(16) Uani 1 1 d . . .
H14 H 0.4917 0.1967 0.8073 0.073 Uiso 1 1 calc R . .
C15 C 0.5563(9) 0.1711(8) 0.6817(4) 0.0576(15) Uani 1 1 d . . .
H15 H 0.6842 0.1371 0.6993 0.069 Uiso 1 1 calc R . .
C16 C 0.4830(8) 0.1853(7) 0.5911(4) 0.0490(13) Uani 1 1 d . . .
H16 H 0.5611 0.1593 0.5479 0.059 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
O1 S1 O2 119.6(3) . . ?
O1 S1 F1 108.8(3) . . ?
O2 S1 F1 105.8(2) . . ?
O1 S1 C3 110.5(2) . . ?
O2 S1 C3 110.9(2) . . ?
F1 S1 C3 99.1(2) . . ?
N1 C1 C2 177.9(6) . . ?
C1 C2 C3 117.1(4) . . ?
C1 C2 C4 119.8(4) . . ?
C3 C2 C4 59.0(3) . . ?
C1 C2 H2 116.2 . . ?
C3 C2 H2 116.2 . . ?
C4 C2 H2 116.2 . . ?
C4 C3 C2 60.7(3) . . ?
C4 C3 S1 118.6(3) . . ?
C2 C3 S1 116.9(3) . . ?
C4 C3 H3 116.4 . . ?
C2 C3 H3 116.4 . . ?
S1 C3 H3 116.4 . . ?
C3 C4 C5 120.2(4) . . ?
C3 C4 C2 60.4(3) . . ?
C5 C4 C2 121.9(4) . . ?
C3 C4 H4 114.6 . . ?
C5 C4 H4 114.6 . . ?
C2 C4 H4 114.6 . . ?
C10 C5 C6 117.5(4) . . ?
C10 C5 C4 120.8(4) . . ?
C6 C5 C4 121.7(4) . . ?
C5 C6 C7 121.0(4) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 121.6(4) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 116.3(4) . . ?
C7 C8 C11 121.6(4) . . ?
C9 C8 C11 122.1(4) . . ?
C10 C9 C8 121.9(4) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C9 C10 C5 121.7(5) . . ?
C9 C10 H10 119.1 . . ?
C5 C10 H10 119.1 . . ?
C12 C11 C16 116.8(5) . . ?
C12 C11 C8 122.2(5) . . ?
C16 C11 C8 121.0(4) . . ?
C13 C12 C11 122.0(5) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C14 C13 C12 119.7(5) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 120.2(5) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 120.3(5) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 121.0(5) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
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 1.529(3) . ?
N1 C1 1.135(7) . ?
O1 S1 1.380(4) . ?
O2 S1 1.413(4) . ?
S1 C3 1.741(4) . ?
C1 C2 1.435(7) . ?
C2 C3 1.504(6) . ?
C2 C4 1.508(7) . ?
C2 H2 0.9800 . ?
C3 C4 1.483(6) . ?
C3 H3 0.9800 . ?
C4 C5 1.494(6) . ?
C4 H4 0.9800 . ?
C5 C10 1.376(6) . ?
C5 C6 1.381(6) . ?
C6 C7 1.385(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.383(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.401(7) . ?
C8 C11 1.479(7) . ?
C9 C10 1.356(7) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.391(7) . ?
C11 C16 1.399(7) . ?
C12 C13 1.376(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.364(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(7) . ?
C15 H15 0.9300 . ?
C16 H16 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 179(100) . . . . ?
N1 C1 C2 C4 -113(17) . . . . ?
C1 C2 C3 C4 110.1(5) . . . . ?
C1 C2 C3 S1 -140.6(4) . . . . ?
C4 C2 C3 S1 109.3(4) . . . . ?
O1 S1 C3 C4 32.9(5) . . . . ?
O2 S1 C3 C4 167.9(3) . . . . ?
F1 S1 C3 C4 -81.2(4) . . . . ?
O1 S1 C3 C2 -36.6(5) . . . . ?
O2 S1 C3 C2 98.4(4) . . . . ?
F1 S1 C3 C2 -150.7(4) . . . . ?
C2 C3 C4 C5 -111.8(5) . . . . ?
S1 C3 C4 C5 141.6(4) . . . . ?
S1 C3 C4 C2 -106.5(4) . . . . ?
C1 C2 C4 C3 -105.6(5) . . . . ?
C1 C2 C4 C5 3.6(7) . . . . ?
C3 C2 C4 C5 109.2(5) . . . . ?
C3 C4 C5 C10 144.1(5) . . . . ?
C2 C4 C5 C10 72.2(6) . . . . ?
C3 C4 C5 C6 -38.2(7) . . . . ?
C2 C4 C5 C6 -110.1(6) . . . . ?
C10 C5 C6 C7 0.9(8) . . . . ?
C4 C5 C6 C7 -176.9(5) . . . . ?
C5 C6 C7 C8 -1.2(8) . . . . ?
C6 C7 C8 C9 0.9(8) . . . . ?
C6 C7 C8 C11 178.8(5) . . . . ?
C7 C8 C9 C10 -0.4(8) . . . . ?
C11 C8 C9 C10 -178.2(5) . . . . ?
C8 C9 C10 C5 0.2(8) . . . . ?
C6 C5 C10 C9 -0.4(8) . . . . ?
C4 C5 C10 C9 177.4(5) . . . . ?
C7 C8 C11 C12 -30.3(7) . . . . ?
C9 C8 C11 C12 147.4(5) . . . . ?
C7 C8 C11 C16 150.7(5) . . . . ?
C9 C8 C11 C16 -31.6(7) . . . . ?
C16 C11 C12 C13 0.1(7) . . . . ?
C8 C11 C12 C13 -179.0(5) . . . . ?
C11 C12 C13 C14 0.4(8) . . . . ?
C12 C13 C14 C15 -0.3(9) . . . . ?
C13 C14 C15 C16 -0.3(9) . . . . ?
C14 C15 C16 C11 0.7(8) . . . . ?
C12 C11 C16 C15 -0.6(7) . . . . ?
C8 C11 C16 C15 178.4(4) . . . . ?
