#------------------------------------------------------------------------------
#$Date: 2019-11-04 12:46:54 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222781 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/42/4034238.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_4034238
loop_
_publ_author_name
'Barthelemy, Anne-Laure'
'Anselmi, Elsa'
'Le, Thanh-Nghi'
'Vo-Thanh, Giang'
'Guillot, Régis'
'Miqueu, Karinne'
'Magnier, Emmanuel'
_publ_section_title
;
 Divergent Synthesis of 1,2-Benzo[ e]thiazine and Benzo[ d]thiazole
 Analogues Containing a S-Trifluoromethyl Sulfoximine Group: Preparation
 and New Properties of the Adachi Reagent.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4086
_journal_page_last               4094
_journal_paper_doi               10.1021/acs.joc.9b00079
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C15 H10 F3 N O S'
_chemical_formula_sum            'C15 H10 F3 N O S'
_chemical_formula_weight         309.30
_space_group_crystal_system      monoclinic
_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_Int_Tables_number      14
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.410(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0768(4)
_cell_length_b                   10.4534(5)
_cell_length_c                   13.9478(6)
_cell_measurement_reflns_used    9106
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      36.35
_cell_measurement_theta_min      2.45
_cell_volume                     1301.63(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            45767
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         36.409
_diffrn_reflns_theta_min         2.450
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_T_max  0.9701
_exptl_absorpt_correction_T_min  0.9458
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.843
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         6320
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0366
_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)+(0.0456P)²+0.6834P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0982
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5416
_reflns_number_total             6320
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b00079_si_002.cif
_cod_data_source_block           5e
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4034238
_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   0.959
_shelx_estimated_absorpt_t_max   0.970
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.55412(9) 0.25400(8) 0.43976(6) 0.00997(13) Uani 1 1 d . .
C2 C 0.66234(10) 0.19573(8) 0.39555(6) 0.01261(14) Uani 1 1 d . .
H2 H 0.6385 0.1578 0.3344 0.015 Uiso 1 1 calc R U
C3 C 0.80780(10) 0.19729(9) 0.44773(7) 0.01571(15) Uani 1 1 d . .
H3 H 0.8843 0.1591 0.4216 0.019 Uiso 1 1 calc R U
C4 C 0.84022(10) 0.25603(9) 0.53950(7) 0.01642(16) Uani 1 1 d . .
H4 H 0.9384 0.2556 0.5734 0.020 Uiso 1 1 calc R U
C5 C 0.72978(10) 0.31499(9) 0.58145(7) 0.01425(14) Uani 1 1 d . .
H5 H 0.7537 0.3543 0.6421 0.017 Uiso 1 1 calc R U
C6 C 0.44071(9) 0.43073(8) 0.64073(6) 0.01138(13) Uani 1 1 d . .
H6 H 0.5323 0.4375 0.6829 0.014 Uiso 1 1 calc R U
C7 C 0.31421(10) 0.48994(8) 0.67534(6) 0.01140(13) Uani 1 1 d . .
C8 C 0.34597(11) 0.56265(8) 0.76167(6) 0.01383(14) Uani 1 1 d . .
H8 H 0.4442 0.5685 0.7949 0.017 Uiso 1 1 calc R U
C9 C 0.23272(11) 0.62578(9) 0.79795(7) 0.01607(16) Uani 1 1 d . .
H9 H 0.2558 0.6739 0.8547 0.019 Uiso 1 1 calc R U
C10 C 0.08546(11) 0.61700(9) 0.74953(7) 0.01634(16) Uani 1 1 d . .
H10 H 0.0097 0.6591 0.7738 0.020 Uiso 1 1 calc R U
C11 C 0.05142(10) 0.54476(9) 0.66438(7) 0.01514(15) Uani 1 1 d . .
H11 H -0.0474 0.5385 0.6321 0.018 Uiso 1 1 calc R U
C12 C 0.16419(10) 0.48189(9) 0.62720(7) 0.01354(14) Uani 1 1 d . .
H12 H 0.1402 0.4343 0.5702 0.016 Uiso 1 1 calc R U
C13 C 0.28907(10) 0.10767(9) 0.39977(7) 0.01522(15) Uani 1 1 d . .
C14 C 0.44452(9) 0.36770(8) 0.55679(6) 0.01048(13) Uani 1 1 d . .
C15 C 0.58290(9) 0.31394(8) 0.53083(6) 0.01028(13) Uani 1 1 d . .
N1 N 0.31692(8) 0.34541(7) 0.48300(5) 0.01235(12) Uani 1 1 d . .
O1 O 0.31147(8) 0.31145(7) 0.29883(5) 0.01772(13) Uani 1 1 d . .
F1 F 0.34005(9) 0.05396(7) 0.48489(5) 0.02599(15) Uani 1 1 d . .
F2 F 0.32866(9) 0.03697(7) 0.32989(5) 0.02660(15) Uani 1 1 d . .
F3 F 0.14070(7) 0.11222(8) 0.38604(7) 0.03219(18) Uani 1 1 d . .
S1 S 0.36369(2) 0.27215(2) 0.39799(2) 0.01039(5) Uani 1 1 d . .
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
C2 C1 C15 124.62(8)
C2 C1 S1 129.84(7)
C15 C1 S1 105.53(6)
C3 C2 C1 116.33(8)
C3 C2 H2 121.8
C1 C2 H2 121.8
C2 C3 C4 120.45(8)
C2 C3 H3 119.8
C4 C3 H3 119.8
C5 C4 C3 121.95(8)
C5 C4 H4 119.0
C3 C4 H4 119.0
C15 C5 C4 118.67(8)
C15 C5 H5 120.7
C4 C5 H5 120.7
C14 C6 C7 129.68(8)
C14 C6 H6 115.2
C7 C6 H6 115.2
C12 C7 C8 118.09(8)
C12 C7 C6 124.56(8)
C8 C7 C6 117.34(8)
C9 C8 C7 121.07(9)
C9 C8 H8 119.5
C7 C8 H8 119.5
C10 C9 C8 120.11(9)
C10 C9 H9 119.9
C8 C9 H9 119.9
C9 C10 C11 119.75(9)
C9 C10 H10 120.1
C11 C10 H10 120.1
C12 C11 C10 120.53(9)
C12 C11 H11 119.7
C10 C11 H11 119.7
C11 C12 C7 120.45(8)
C11 C12 H12 119.8
C7 C12 H12 119.8
F1 C13 F2 109.10(8)
F1 C13 F3 109.09(8)
F2 C13 F3 108.51(8)
F1 C13 S1 109.75(6)
F2 C13 S1 111.12(7)
F3 C13 S1 109.23(7)
C6 C14 N1 124.23(8)
C6 C14 C15 123.64(8)
N1 C14 C15 112.14(7)
C5 C15 C1 117.99(8)
C5 C15 C14 130.60(8)
C1 C15 C14 111.42(7)
C14 N1 S1 109.75(6)
O1 S1 N1 120.75(4)
O1 S1 C1 119.35(4)
N1 S1 C1 101.15(4)
O1 S1 C13 102.74(5)
N1 S1 C13 107.49(4)
C1 S1 C13 103.84(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3911(12)
C1 C15 1.3979(12)
C1 S1 1.7319(8)
C2 C3 1.3878(13)
C2 H2 0.9300
C3 C4 1.4022(14)
C3 H3 0.9300
C4 C5 1.3926(13)
C4 H4 0.9300
C5 C15 1.3915(12)
C5 H5 0.9300
C6 C14 1.3493(11)
C6 C7 1.4611(12)
C6 H6 0.9300
C7 C12 1.4078(12)
C7 C8 1.4090(12)
C8 C9 1.3915(13)
C8 H8 0.9300
C9 C10 1.3874(14)
C9 H9 0.9300
C10 C11 1.3942(13)
C10 H10 0.9300
C11 C12 1.3929(12)
C11 H11 0.9300
C12 H12 0.9300
C13 F1 1.3193(12)
C13 F2 1.3236(11)
C13 F3 1.3264(11)
C13 S1 1.8498(9)
C14 N1 1.4228(11)
C14 C15 1.4795(12)
N1 S1 1.5345(8)
O1 S1 1.4385(7)
