#------------------------------------------------------------------------------
#$Date: 2021-09-06 12:31:55 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268577 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/85/7128595.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_7128595
loop_
_publ_author_name
'Riley, William'
'Jones, Andrew C.'
'Singh, Kuldip'
'Browne, Duncan L.'
'Stuart, Alison M.'
_publ_section_title
;
 Accessing novel fluorinated heterocycles with the hypervalent
 fluoroiodane reagent by solution and mechanochemical synthesis.
;
_journal_issue                   60
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7406
_journal_page_last               7409
_journal_paper_doi               10.1039/d1cc02587b
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C18 H19 F N2 O2 S'
_chemical_formula_sum            'C18 H19 F N2 O2 S'
_chemical_formula_weight         346.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-05-11 deposited with the CCDC.	2021-07-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.644(4)
_cell_length_b                   9.1535(18)
_cell_length_c                   20.027(4)
_cell_measurement_reflns_used    822
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      21.520
_cell_measurement_theta_min      2.680
_cell_volume                     3417.8(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Apex 2000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1007
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            24963
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.034
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_correction_T_min  0.726
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
absoprtion correction based on 5721 reflections(SADABS);Rint 0.0776 before
correction and 0.0502 after.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3361
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0511
_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)+(0.0473P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1105
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2263
_reflns_number_total             3361
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc02587b2.cif
_cod_data_source_block           18105
_cod_depositor_comments
'Adding full bibliography for 7128595--7128600.cif.'
_cod_original_cell_volume        3417.7(11)
_cod_database_code               7128595
_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. 
;
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'
'-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 1.09142(3) 0.40441(7) 0.38337(3) 0.02834(18) Uani 1 1 d . . . . .
F1 F 0.98791(7) 0.31243(15) 0.20003(7) 0.0383(4) Uani 1 1 d . . . . .
O1 O 1.05600(9) 0.32999(18) 0.43629(8) 0.0330(4) Uani 1 1 d . . . . .
O2 O 1.15326(8) 0.34152(19) 0.35255(8) 0.0359(5) Uani 1 1 d . . . . .
N1 N 0.96772(10) 0.4796(2) 0.34477(10) 0.0274(5) Uani 1 1 d . . . . .
N2 N 1.03270(10) 0.4207(2) 0.32114(9) 0.0272(5) Uani 1 1 d . . . . .
C1 C 1.06099(13) 0.4788(3) 0.25771(12) 0.0297(6) Uani 1 1 d . . . . .
H1A H 1.104344 0.423761 0.244273 0.036 Uiso 1 1 calc R U . . .
H1B H 1.074274 0.582896 0.263106 0.036 Uiso 1 1 calc R U . . .
C2 C 1.00356(13) 0.4637(3) 0.20505(12) 0.0292(6) Uani 1 1 d . . . . .
C3 C 0.93543(12) 0.5379(3) 0.22772(12) 0.0292(6) Uani 1 1 d . . . . .
H3A H 0.936724 0.641272 0.213223 0.035 Uiso 1 1 calc R U . . .
H3B H 0.894149 0.490720 0.205315 0.035 Uiso 1 1 calc R U . . .
C4 C 0.92358(12) 0.5331(3) 0.30193(12) 0.0268(6) Uani 1 1 d . . . . .
C5 C 0.85713(12) 0.5985(3) 0.33026(12) 0.0282(6) Uani 1 1 d . . . . .
C6 C 0.80303(14) 0.6520(3) 0.28871(14) 0.0421(7) Uani 1 1 d . . . . .
H6 H 0.808041 0.644015 0.241646 0.051 Uiso 1 1 calc R U . . .
C7 C 0.74228(15) 0.7163(3) 0.31516(16) 0.0516(8) Uani 1 1 d . . . . .
H7 H 0.705787 0.751363 0.286193 0.062 Uiso 1 1 calc R U . . .
C8 C 0.73429(15) 0.7298(3) 0.38349(17) 0.0503(8) Uani 1 1 d . . . . .
H8 H 0.692708 0.774737 0.401672 0.060 Uiso 1 1 calc R U . . .
C9 C 0.78737(15) 0.6775(3) 0.42485(14) 0.0433(7) Uani 1 1 d . . . . .
H9 H 0.781993 0.685794 0.471873 0.052 Uiso 1 1 calc R U . . .
C10 C 0.84836(14) 0.6130(3) 0.39896(13) 0.0359(7) Uani 1 1 d . . . . .
H10 H 0.884593 0.578227 0.428297 0.043 Uiso 1 1 calc R U . . .
C11 C 1.03011(14) 0.5143(3) 0.13760(12) 0.0405(7) Uani 1 1 d . . . . .
H11A H 1.043744 0.617562 0.140197 0.061 Uiso 1 1 calc R U . . .
H11B H 0.991919 0.502232 0.104432 0.061 Uiso 1 1 calc R U . . .
H11C H 1.071863 0.456012 0.124444 0.061 Uiso 1 1 calc R U . . .
C12 C 1.11212(12) 0.5826(3) 0.40925(12) 0.0271(6) Uani 1 1 d . . . . .
C13 C 1.16801(13) 0.6582(3) 0.37921(13) 0.0338(6) Uani 1 1 d . . . . .
H13 H 1.196094 0.613153 0.345417 0.041 Uiso 1 1 calc R U . . .
C14 C 1.18221(13) 0.7990(3) 0.39894(13) 0.0373(7) Uani 1 1 d . . . . .
H14 H 1.220631 0.850667 0.378631 0.045 Uiso 1 1 calc R U . . .
C15 C 1.14146(13) 0.8675(3) 0.44810(13) 0.0326(6) Uani 1 1 d . . . . .
C16 C 1.08606(14) 0.7896(3) 0.47706(12) 0.0358(6) Uani 1 1 d . . . . .
H16 H 1.058003 0.834483 0.510939 0.043 Uiso 1 1 calc R U . . .
C17 C 1.07060(14) 0.6488(3) 0.45799(12) 0.0330(6) Uani 1 1 d . . . . .
H17 H 1.031878 0.597534 0.478005 0.040 Uiso 1 1 calc R U . . .
C18 C 1.15794(15) 1.0211(3) 0.47028(15) 0.0464(8) Uani 1 1 d . . . . .
H18A H 1.113121 1.071877 0.480982 0.070 Uiso 1 1 calc R U . . .
H18B H 1.182786 1.073120 0.434301 0.070 Uiso 1 1 calc R U . . .
H18C H 1.188649 1.018221 0.509971 0.070 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'
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 120.23(11) . . ?
O1 S1 N2 107.18(10) . . ?
O2 S1 N2 104.08(10) . . ?
O1 S1 C12 109.10(11) . . ?
O2 S1 C12 108.95(11) . . ?
N2 S1 C12 106.39(11) . . ?
C4 N1 N2 118.2(2) . . ?
N1 N2 C1 117.33(18) . . ?
N1 N2 S1 110.40(14) . . ?
C1 N2 S1 116.22(15) . . ?
N2 C1 C2 108.37(19) . . ?
N2 C1 H1A 110.0 . . ?
C2 C1 H1A 110.0 . . ?
N2 C1 H1B 110.0 . . ?
C2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
F1 C2 C1 106.58(19) . . ?
F1 C2 C3 106.70(19) . . ?
C1 C2 C3 110.2(2) . . ?
F1 C2 C11 107.66(19) . . ?
C1 C2 C11 111.3(2) . . ?
C3 C2 C11 114.0(2) . . ?
C4 C3 C2 114.1(2) . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
N1 C4 C5 115.6(2) . . ?
N1 C4 C3 125.2(2) . . ?
C5 C4 C3 119.2(2) . . ?
C10 C5 C6 118.1(2) . . ?
C10 C5 C4 120.9(2) . . ?
C6 C5 C4 121.0(2) . . ?
C7 C6 C5 120.9(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.4(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 119.1(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 121.0(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C5 120.5(2) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 120.4(2) . . ?
C17 C12 S1 119.47(19) . . ?
C13 C12 S1 120.0(2) . . ?
C14 C13 C12 119.2(2) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 121.4(2) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C16 C15 C14 118.2(2) . . ?
C16 C15 C18 120.7(2) . . ?
C14 C15 C18 121.2(2) . . ?
C17 C16 C15 121.6(2) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C12 119.3(2) . . ?
C16 C17 H17 120.4 . . ?
C12 C17 H17 120.4 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
S1 O1 1.4226(17) . ?
S1 O2 1.4288(17) . ?
S1 N2 1.6655(19) . ?
S1 C12 1.755(3) . ?
F1 C2 1.418(3) . ?
N1 C4 1.286(3) . ?
N1 N2 1.408(3) . ?
N2 C1 1.475(3) . ?
C1 C2 1.509(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.510(3) . ?
C2 C11 1.511(3) . ?
C3 C4 1.503(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.488(3) . ?
C5 C10 1.392(3) . ?
C5 C6 1.396(3) . ?
C6 C7 1.382(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.382(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.377(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C17 1.386(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.373(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(3) . ?
C15 C18 1.506(4) . ?
C16 C17 1.375(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
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
C4 N1 N2 C1 26.6(3) . . . . ?
C4 N1 N2 S1 162.87(17) . . . . ?
O1 S1 N2 N1 50.50(17) . . . . ?
O2 S1 N2 N1 178.89(14) . . . . ?
C12 S1 N2 N1 -66.10(17) . . . . ?
O1 S1 N2 C1 -172.67(16) . . . . ?
O2 S1 N2 C1 -44.29(19) . . . . ?
C12 S1 N2 C1 70.72(19) . . . . ?
N1 N2 C1 C2 -54.9(3) . . . . ?
S1 N2 C1 C2 171.33(15) . . . . ?
N2 C1 C2 F1 -60.0(2) . . . . ?
N2 C1 C2 C3 55.4(3) . . . . ?
N2 C1 C2 C11 -177.17(19) . . . . ?
F1 C2 C3 C4 83.1(2) . . . . ?
C1 C2 C3 C4 -32.3(3) . . . . ?
C11 C2 C3 C4 -158.3(2) . . . . ?
N2 N1 C4 C5 -177.86(19) . . . . ?
N2 N1 C4 C3 0.2(3) . . . . ?
C2 C3 C4 N1 3.9(3) . . . . ?
C2 C3 C4 C5 -178.1(2) . . . . ?
N1 C4 C5 C10 6.4(3) . . . . ?
C3 C4 C5 C10 -171.8(2) . . . . ?
N1 C4 C5 C6 -176.0(2) . . . . ?
C3 C4 C5 C6 5.8(3) . . . . ?
C10 C5 C6 C7 -0.5(4) . . . . ?
C4 C5 C6 C7 -178.2(2) . . . . ?
C5 C6 C7 C8 0.5(4) . . . . ?
C6 C7 C8 C9 -0.5(4) . . . . ?
C7 C8 C9 C10 0.5(4) . . . . ?
C8 C9 C10 C5 -0.5(4) . . . . ?
C6 C5 C10 C9 0.5(4) . . . . ?
C4 C5 C10 C9 178.2(2) . . . . ?
O1 S1 C12 C17 -26.6(2) . . . . ?
O2 S1 C12 C17 -159.59(19) . . . . ?
N2 S1 C12 C17 88.7(2) . . . . ?
O1 S1 C12 C13 155.85(19) . . . . ?
O2 S1 C12 C13 22.8(2) . . . . ?
N2 S1 C12 C13 -88.8(2) . . . . ?
C17 C12 C13 C14 0.8(4) . . . . ?
S1 C12 C13 C14 178.32(19) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C13 C14 C15 C18 179.1(2) . . . . ?
C14 C15 C16 C17 -0.5(4) . . . . ?
C18 C15 C16 C17 -179.4(2) . . . . ?
C15 C16 C17 C12 0.9(4) . . . . ?
C13 C12 C17 C16 -1.0(4) . . . . ?
S1 C12 C17 C16 -178.59(19) . . . . ?
