#------------------------------------------------------------------------------
#$Date: 2016-03-25 23:27:44 +0200 (Fri, 25 Mar 2016) $
#$Revision: 180040 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/34/7033404.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_7033404
loop_
_publ_author_name
'Clark, Ewan R.'
'Hayward, John J.'
'Leontowicz, Bryce J.'
'Anwar, Muhammad U.'
'Pilkington, Melanie'
'Rawson, Jeremy M.'
_publ_section_title
;
 Copper-promoted aerial oxidation of benzothiadiazines: access to
 benzothiadiazine S-oxide heterocycles.
;
_journal_issue                   5
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2071
_journal_page_last               2074
_journal_paper_doi               10.1039/c4dt03467h
_journal_volume                  44
_journal_year                    2015
_chemical_formula_moiety         'C14 H9 F3 N2 O S'
_chemical_formula_sum            'C14 H9 F3 N2 O S'
_chemical_formula_weight         310.29
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-12-09 deposited with the CCDC.
2014-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.918(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7488(9)
_cell_length_b                   8.6205(6)
_cell_length_c                   12.1309(8)
_cell_measurement_reflns_used    9989
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.71
_cell_measurement_theta_min      2.87
_cell_volume                     1304.46(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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-II CCD'
_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  0.0289
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19374
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.87
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.9832
_exptl_absorpt_correction_T_min  0.9172
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.211
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.211
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0307P)²+1.0263P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0870
_reflns_number_gt                2232
_reflns_number_total             2303
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4dt03467h2.cif
_cod_data_source_block           compound_2c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 7033401--7033404.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7033404
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.65273(4) 0.05147(5) -0.14912(4) 0.01891(14) Uani 1 1 d .
C3 C 0.81232(14) 0.0631(2) 0.17610(15) 0.0185(4) Uani 1 1 d .
H3 H 0.8071 0.1144 0.2441 0.022 Uiso 1 1 calc R
C4 C 0.89713(15) -0.0362(2) 0.17263(16) 0.0210(4) Uani 1 1 d .
C2 C 0.73445(14) 0.0863(2) 0.07762(15) 0.0171(4) Uani 1 1 d .
C9 C 0.46649(14) 0.2797(2) 0.01676(15) 0.0176(4) Uani 1 1 d .
C8 C 0.55878(14) 0.1867(2) -0.00360(14) 0.0172(4) Uani 1 1 d .
C1 C 0.74515(14) 0.0124(2) -0.02162(15) 0.0184(4) Uani 1 1 d .
C7 C 0.97867(15) -0.0667(2) 0.27812(17) 0.0256(4) Uani 1 1 d .
C10 C 0.39340(15) 0.3380(2) -0.07600(15) 0.0225(4) Uani 1 1 d .
H10 H 0.4021 0.3146 -0.1501 0.027 Uiso 1 1 calc R
C14 C 0.45158(14) 0.3128(2) 0.12487(15) 0.0207(4) Uani 1 1 d .
H14 H 0.4993 0.2708 0.1885 0.025 Uiso 1 1 calc R
C6 C 0.83046(16) -0.0880(2) -0.02302(16) 0.0244(4) Uani 1 1 d .
H6 H 0.8358 -0.1399 -0.0908 0.029 Uiso 1 1 calc R
C5 C 0.90716(16) -0.1124(2) 0.07353(17) 0.0257(4) Uani 1 1 d .
H5 H 0.9659 -0.1798 0.0728 0.031 Uiso 1 1 calc R
C13 C 0.36754(15) 0.4067(2) 0.14001(17) 0.0256(4) Uani 1 1 d .
H13 H 0.3588 0.4309 0.2140 0.031 Uiso 1 1 calc R
C11 C 0.30883(16) 0.4293(2) -0.06050(17) 0.0260(4) Uani 1 1 d .
H11 H 0.2591 0.4675 -0.1240 0.031 Uiso 1 1 calc R
C12 C 0.29601(16) 0.4656(2) 0.04750(18) 0.0278(4) Uani 1 1 d .
H12 H 0.2386 0.5304 0.0580 0.033 Uiso 1 1 calc R
N1 N 0.54770(12) 0.11578(18) -0.10099(12) 0.0198(3) Uani 1 1 d .
N2 N 0.64702(12) 0.18136(18) 0.08019(12) 0.0175(3) Uani 1 1 d .
H2 H 0.6492 0.2412 0.1394 0.021 Uiso 1 1 calc R
F2 F 1.07833(10) -0.0670(2) 0.26028(12) 0.0504(4) Uani 1 1 d .
F3 F 0.97579(12) 0.03518(17) 0.35974(11) 0.0503(4) Uani 1 1 d .
F1 F 0.96563(11) -0.20620(16) 0.32161(11) 0.0444(4) Uani 1 1 d .
O1 O 0.69844(10) 0.18814(16) -0.19933(11) 0.0248(3) 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'
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'
O O 0.0106 0.0060 '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
O1 S1 N1 106.83(8)
O1 S1 C1 105.06(8)
N1 S1 C1 101.27(8)
C4 C3 C2 118.82(17)
C4 C3 H3 120.6
C2 C3 H3 120.6
C3 C4 C5 121.75(18)
C3 C4 C7 119.42(17)
C5 C4 C7 118.81(17)
N2 C2 C1 120.75(16)
N2 C2 C3 119.72(16)
C1 C2 C3 119.52(17)
C14 C9 C10 119.08(17)
C14 C9 C8 122.26(16)
C10 C9 C8 118.65(16)
N1 C8 N2 125.39(16)
N1 C8 C9 117.35(16)
N2 C8 C9 117.26(15)
C2 C1 C6 120.72(17)
C2 C1 S1 120.06(14)
C6 C1 S1 119.17(14)
F3 C7 F2 107.23(17)
F3 C7 F1 105.99(17)
F2 C7 F1 105.24(16)
F3 C7 C4 113.55(16)
F2 C7 C4 112.27(16)
F1 C7 C4 112.00(16)
C11 C10 C9 120.38(17)
C11 C10 H10 119.8
C9 C10 H10 119.8
C13 C14 C9 120.29(17)
C13 C14 H14 119.9
C9 C14 H14 119.9
C5 C6 C1 120.20(18)
C5 C6 H6 119.9
C1 C6 H6 119.9
C6 C5 C4 118.97(18)
C6 C5 H5 120.5
C4 C5 H5 120.5
C14 C13 C12 120.24(18)
C14 C13 H13 119.9
C12 C13 H13 119.9
C10 C11 C12 120.32(18)
C10 C11 H11 119.8
C12 C11 H11 119.8
C11 C12 C13 119.64(18)
C11 C12 H12 120.2
C13 C12 H12 120.2
C8 N1 S1 121.80(13)
C8 N2 C2 123.39(15)
C8 N2 H2 118.3
C2 N2 H2 118.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4984(14)
S1 N1 1.6626(16)
S1 C1 1.7724(18)
C3 C4 1.386(3)
C3 C2 1.401(3)
C3 H3 0.9500
C4 C5 1.399(3)
C4 C7 1.496(3)
C2 N2 1.389(2)
C2 C1 1.393(3)
C9 C14 1.393(3)
C9 C10 1.398(3)
C9 C8 1.486(2)
C8 N1 1.312(2)
C8 N2 1.352(2)
C1 C6 1.393(3)
C7 F3 1.330(2)
C7 F2 1.332(2)
C7 F1 1.337(2)
C10 C11 1.379(3)
C10 H10 0.9500
C14 C13 1.385(3)
C14 H14 0.9500
C6 C5 1.378(3)
C6 H6 0.9500
C5 H5 0.9500
C13 C12 1.388(3)
C13 H13 0.9500
C11 C12 1.389(3)
C11 H11 0.9500
C12 H12 0.9500
N2 H2 0.8800
