#------------------------------------------------------------------------------
#$Date: 2020-10-04 06:34:46 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257126 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/87/4038753.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_4038753
loop_
_publ_author_name
'Nguyen, Thi Mo'
'Cao, Hoang Anh'
'Thuong Cao, Thi Thuong'
'Koyama, Satoki'
'Mac, Dinh Hung'
'Nguyen, Thanh Binh'
_publ_section_title
;
 Access to [2,1]Benzothiazine S,S-Dioxides from
 β-Substituted o-Nitrostyrenes and Sulfur.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12058
_journal_page_last               12066
_journal_paper_doi               10.1021/acs.joc.0c00918
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C13 H9 F N2 O2 S'
_chemical_formula_sum            'C13 H9 F N2 O2 S'
_chemical_formula_weight         276.28
_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-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3094(3)
_cell_length_b                   11.2860(5)
_cell_length_c                   18.0876(8)
_cell_measurement_reflns_used    9917
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      30.59
_cell_measurement_theta_min      3.01
_cell_volume                     1492.12(11)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.918
_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  0.0415
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26732
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.469
_diffrn_reflns_theta_min         2.886
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0650 before and 0.0597 after correction.
The Ratio of minimum to maximum transmission is 0.9319.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.153
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 980 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.853
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         4356
_refine_ls_number_restraints     156
_refine_ls_restrained_S_all      0.844
_refine_ls_R_factor_all          0.1037
_refine_ls_R_factor_gt           0.0599
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1873
_refine_ls_wR_factor_ref         0.2290
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.823
_reflns_number_gt                2947
_reflns_number_total             4356
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00918_si_003.cif
_cod_data_source_block           oPy
_cod_depositor_comments
'Adding full bibliography for 4038753--4038754.cif.'
_cod_database_code               4038753
_shelx_shelxl_version_number     2014/7
_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   0.954
_shelx_estimated_absorpt_t_max   0.966
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
S9 S 0.12540(17) 0.44310(9) 0.55721(5) 0.0453(3) Uani 1 1 d . U . . .
F1 F 0.0639(5) 0.1864(3) 0.23425(15) 0.0712(9) Uani 1 1 d . U . . .
O1 O 0.2451(6) 0.4997(3) 0.60854(17) 0.0613(10) Uani 1 1 d . U . . .
O2 O -0.0644(5) 0.4774(3) 0.5605(2) 0.0583(9) Uani 1 1 d . U . . .
N12 N 0.1653(5) 0.1132(3) 0.63557(19) 0.0457(8) Uani 1 1 d . U . . .
C5 C 0.1261(6) 0.2773(4) 0.4249(2) 0.0414(8) Uani 1 1 d . U . . .
N10 N 0.2118(6) 0.4656(4) 0.4750(2) 0.0526(10) Uani 1 1 d . U . . .
H10 H 0.2882 0.5228 0.4691 0.063 Uiso 1 1 calc R U . . .
C6 C 0.1668(6) 0.3958(4) 0.4140(2) 0.0432(9) Uani 1 1 d . U . . .
C3 C 0.0990(7) 0.2557(5) 0.2939(2) 0.0548(12) Uani 1 1 d . U . . .
C7 C 0.1207(6) 0.2272(3) 0.4987(2) 0.0398(8) Uani 1 1 d . U . . .
H7 H 0.1068 0.1455 0.5021 0.048 Uiso 1 1 calc R U . . .
C11 C 0.1343(6) 0.2298(4) 0.6364(2) 0.0394(8) Uani 1 1 d . U . . .
C4 C 0.0907(7) 0.2065(4) 0.3632(2) 0.0503(11) Uani 1 1 d . U . . .
H4 H 0.0618 0.1268 0.3691 0.060 Uiso 1 1 calc R U . . .
C16 C 0.0979(8) 0.2943(4) 0.7009(2) 0.0520(12) Uani 1 1 d . U . . .
H16 H 0.0743 0.3752 0.6991 0.062 Uiso 1 1 calc R U . . .
C14 C 0.1394(7) 0.1122(5) 0.7677(2) 0.0557(11) Uani 1 1 d . U . . .
H14 H 0.1484 0.0697 0.8115 0.067 Uiso 1 1 calc R U . . .
C8 C 0.1337(6) 0.2874(3) 0.5627(2) 0.0395(8) Uani 1 1 d . U . . .
C13 C 0.1664(7) 0.0580(5) 0.7012(3) 0.0568(12) Uani 1 1 d . U . . .
H13 H 0.1871 -0.0233 0.7013 0.068 Uiso 1 1 calc R U . . .
C2 C 0.1450(7) 0.3733(5) 0.2821(2) 0.0530(11) Uani 1 1 d . U . . .
H2 H 0.1521 0.4040 0.2345 0.064 Uiso 1 1 calc R U . . .
C1 C 0.1797(7) 0.4435(5) 0.3427(2) 0.0532(11) Uani 1 1 d . U . . .
H1 H 0.2119 0.5226 0.3363 0.064 Uiso 1 1 calc R U . . .
C15 C 0.0979(8) 0.2330(5) 0.7685(2) 0.0600(13) Uani 1 1 d . U . . .
H15 H 0.0709 0.2717 0.8125 0.072 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'
F F 0.0171 0.0103 '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
O1 S9 O2 116.3(2) . . ?
O1 S9 N10 106.6(2) . . ?
O2 S9 N10 111.6(2) . . ?
O1 S9 C8 112.9(2) . . ?
O2 S9 C8 107.4(2) . . ?
N10 S9 C8 101.1(2) . . ?
C11 N12 C13 116.8(4) . . ?
C6 C5 C4 118.6(4) . . ?
C6 C5 C7 120.9(4) . . ?
C4 C5 C7 120.5(4) . . ?
C6 N10 S9 122.7(3) . . ?
C5 C6 N10 118.9(4) . . ?
C5 C6 C1 121.1(4) . . ?
N10 C6 C1 119.7(4) . . ?
F1 C3 C4 119.0(5) . . ?
F1 C3 C2 118.4(4) . . ?
C4 C3 C2 122.6(4) . . ?
C8 C7 C5 126.4(3) . . ?
N12 C11 C16 123.5(4) . . ?
N12 C11 C8 115.0(3) . . ?
C16 C11 C8 121.4(4) . . ?
C3 C4 C5 119.4(4) . . ?
C11 C16 C15 118.0(4) . . ?
C13 C14 C15 118.6(4) . . ?
C7 C8 C11 123.5(3) . . ?
C7 C8 S9 117.0(3) . . ?
C11 C8 S9 119.2(3) . . ?
N12 C13 C14 124.8(4) . . ?
C1 C2 C3 118.3(4) . . ?
C2 C1 C6 119.9(5) . . ?
C14 C15 C16 118.2(4) . . ?
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
S9 O1 1.427(4) . ?
S9 O2 1.442(4) . ?
S9 N10 1.635(4) . ?
S9 C8 1.761(4) . ?
F1 C3 1.358(6) . ?
N12 C11 1.336(6) . ?
N12 C13 1.340(5) . ?
C5 C6 1.385(6) . ?
C5 C4 1.396(6) . ?
C5 C7 1.449(5) . ?
N10 C6 1.395(6) . ?
C6 C1 1.401(5) . ?
C3 C4 1.372(6) . ?
C3 C2 1.386(8) . ?
C7 C8 1.345(5) . ?
C11 C16 1.402(6) . ?
C11 C8 1.483(5) . ?
C16 C15 1.404(6) . ?
C14 C13 1.364(7) . ?
C14 C15 1.396(8) . ?
C2 C1 1.376(7) . ?
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
C16 H16 O1 0.93 2.49 3.054(6) 119.0 .
C14 H14 O2 0.93 2.61 3.504(5) 161.0 3_546
C2 H2 O1 0.93 2.63 3.544(5) 166.2 2_564
