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#$Date: 2023-03-08 10:59:41 +0200 (Wed, 08 Mar 2023) $
#$Revision: 281735 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/68/8106878.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_8106878
loop_
_publ_author_name
'Bhatt, Nilay'
'Samipillai, Marivel'
'Bhatt, Pralav'
'Govender, Thavendran'
'Kruger, Hendrik G.'
'Maguire, Glenn E.M.'
_publ_section_title
;
 Crystal structure of butyl
 2-(3,5-dimethyl-1,1-dioxido-2H-1,2,6-thiadiazin-4-yl)benzoate,
 C16H20N2O4S
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              373
_journal_page_last               374
_journal_paper_doi               10.1515/ncrs-2014-9094
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C16 H20 N2 O4 S'
_chemical_formula_weight         336.40
_chemical_name_systematic
;
butyl-2-(3,5-dimethyl-1,1-dioxido-2H-1,2,6-thiadiazin-4-yl)benzoate
;
_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'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 99.985(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.229(2)
_cell_length_b                   16.995(4)
_cell_length_c                   11.084(3)
_cell_measurement_temperature    173(2)
_cell_volume                     1712.2(7)
_computing_cell_refinement       'SAINT-plus (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'X-Seed (Barbour, 2001)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart ApexII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            29937
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.494
_diffrn_reflns_theta_min         2.217
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.512
_exptl_crystal_size_mid          0.488
_exptl_crystal_size_min          0.358
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3179
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0393
_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)+(0.0548P)²+0.7125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1081
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    0
_reflns_Friedel_fraction_max     0
_reflns_number_gt                2912
_reflns_number_total             3179
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2014-9094_suppl.cif
_cod_data_source_block           1
_cod_original_cell_volume        1712.3(8)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8106878
_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   0.900
_shelx_estimated_absorpt_t_max   0.929
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.29229(5) 0.14261(3) 0.17009(3) 0.04282(15) Uani 1 1 d . . . . .
O1 O 0.31450(17) 0.06281(8) 0.14000(12) 0.0608(4) Uani 1 1 d . . . . .
N1 N 0.42578(17) 0.16965(9) 0.28070(12) 0.0412(3) Uani 1 1 d . . . . .
C1 C 0.42221(17) 0.15397(8) 0.40088(13) 0.0329(3) Uani 1 1 d . . . . .
O2 O 0.28992(18) 0.19865(9) 0.07357(11) 0.0636(4) Uani 1 1 d . . . . .
N2 N 0.14885(17) 0.15038(10) 0.23269(13) 0.0501(4) Uani 1 1 d . . . . .
C2 C 0.29249(16) 0.13422(9) 0.43714(13) 0.0320(3) Uani 1 1 d . . . . .
O3 O 0.19390(14) 0.30071(8) 0.70382(11) 0.0525(3) Uani 1 1 d . . . . .
C3 C 0.15861(18) 0.13848(10) 0.35147(15) 0.0409(4) Uani 1 1 d . . . . .
C4 C 0.29426(16) 0.11639(9) 0.57010(13) 0.0332(3) Uani 1 1 d . . . . .
C5 C 0.27764(16) 0.17327(10) 0.65938(13) 0.0341(3) Uani 1 1 d . . . . .
C6 C 0.28876(19) 0.15047(11) 0.78215(15) 0.0435(4) Uani 1 1 d . . . . .
H7 H 0.2773 0.1889 0.8420 0.052 Uiso 1 1 calc R U . . .
C7 C 0.3159(2) 0.07374(12) 0.81776(16) 0.0516(5) Uani 1 1 d . . . . .
H8 H 0.3249 0.0596 0.9016 0.062 Uiso 1 1 calc R U . . .
C8 C 0.3300(2) 0.01720(12) 0.73075(17) 0.0540(5) Uani 1 1 d . . . . .
H9 H 0.3472 -0.0362 0.7544 0.065 Uiso 1 1 calc R U . . .
C9 C 0.3188(2) 0.03890(10) 0.60831(16) 0.0460(4) Uani 1 1 d . . . . .
H10 H 0.3282 -0.0004 0.5492 0.055 Uiso 1 1 calc R U . . .
C10 C 0.56291(18) 0.16638(12) 0.48694(16) 0.0469(4) Uani 1 1 d . . . . .
H16A H 0.6455 0.1608 0.4426 0.070 Uiso 1 1 calc R U . . .
H16B H 0.5720 0.1272 0.5527 0.070 Uiso 1 1 calc R U . . .
H16C H 0.5640 0.2193 0.5222 0.070 Uiso 1 1 calc R U . . .
C11 C 0.0144(2) 0.13393(16) 0.39667(19) 0.0656(6) Uani 1 1 d . . . . .
H14A H 0.0025 0.1808 0.4456 0.098 Uiso 1 1 calc R U . . .
H14B H 0.0131 0.0868 0.4474 0.098 Uiso 1 1 calc R U . . .
H14C H -0.0663 0.1313 0.3266 0.098 Uiso 1 1 calc R U . . .
C12 C 0.24219(17) 0.25761(10) 0.63256(14) 0.0394(4) Uani 1 1 d . . . . .
C16 C 0.3959(3) 0.40669(16) 0.2083(2) 0.0712(6) Uani 1 1 d . . . . .
H1A H 0.4987 0.4174 0.2019 0.107 Uiso 1 1 calc R U . A 1
H1B H 0.3609 0.3610 0.1577 0.107 Uiso 1 1 calc R U . A 1
H1C H 0.3354 0.4526 0.1797 0.107 Uiso 1 1 calc R U . A 1
O4A O 0.2565(3) 0.2804(2) 0.5214(3) 0.0479(7) Uani 0.7766 1 d . . P B 1
C13A C 0.2039(4) 0.35987(14) 0.4857(3) 0.0578(7) Uani 0.7766 1 d . . P B 1
H13A H 0.2598 0.3994 0.5407 0.069 Uiso 0.7766 1 calc R U P B 1
H13B H 0.0983 0.3649 0.4911 0.069 Uiso 0.7766 1 calc R U P B 1
C14A C 0.2265(3) 0.37267(14) 0.3561(2) 0.0510(6) Uani 0.7766 1 d . . P B 1
H14D H 0.1642 0.4173 0.3210 0.061 Uiso 0.7766 1 calc R U P B 1
H14E H 0.1926 0.3252 0.3074 0.061 Uiso 0.7766 1 calc R U P B 1
C15A C 0.3847(4) 0.38954(18) 0.3430(4) 0.0578(7) Uani 0.7766 1 d . . P B 1
H15A H 0.4470 0.3436 0.3723 0.069 Uiso 0.7766 1 calc R U P B 1
H15B H 0.4215 0.4354 0.3944 0.069 Uiso 0.7766 1 calc R U P B 1
O4B O 0.3143(11) 0.2917(8) 0.5459(11) 0.044(2) Uani 0.2234 1 d . . P B 2
C13B C 0.3087(11) 0.3783(5) 0.5294(7) 0.0476(19) Uani 0.2234 1 d . . P B 2
H13C H 0.3545 0.4045 0.6064 0.057 Uiso 0.2234 1 calc R U P B 2
H13D H 0.2052 0.3959 0.5087 0.057 Uiso 0.2234 1 calc R U P B 2
C14B C 0.3907(11) 0.4001(5) 0.4275(9) 0.051(2) Uani 0.2234 1 d . . P B 2
H14F H 0.4875 0.3734 0.4415 0.062 Uiso 0.2234 1 calc R U P B 2
H14G H 0.4087 0.4576 0.4299 0.062 Uiso 0.2234 1 calc R U P B 2
C15B C 0.3077(14) 0.3777(5) 0.3007(9) 0.048(2) Uani 0.2234 1 d . . P B 2
H15C H 0.2956 0.3199 0.2943 0.057 Uiso 0.2234 1 calc R U P B 2
H15D H 0.2090 0.4023 0.2862 0.057 Uiso 0.2234 1 calc R U P B 2
H1D H 0.502(2) 0.1852(11) 0.2591(19) 0.047(5) Uiso 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'
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
O1 S1 O2 116.39(8) . .
O1 S1 N2 110.13(9) . .
O2 S1 N2 111.25(9) . .
O1 S1 N1 108.77(8) . .
O2 S1 N1 106.49(9) . .
N2 S1 N1 102.84(8) . .
C1 N1 S1 122.08(12) . .
C1 N1 H1D 120.9(14) . .
S1 N1 H1D 116.0(14) . .
N1 C1 C2 120.32(14) . .
N1 C1 C10 115.61(14) . .
C2 C1 C10 123.87(14) . .
C3 N2 S1 120.04(13) . .
C1 C2 C3 119.59(14) . .
C1 C2 C4 118.44(13) . .
C3 C2 C4 121.69(13) . .
N2 C3 C2 125.07(15) . .
N2 C3 C11 115.42(15) . .
C2 C3 C11 119.42(15) . .
C9 C4 C5 117.86(14) . .
C9 C4 C2 117.63(14) . .
C5 C4 C2 124.48(14) . .
C6 C5 C4 119.55(15) . .
C6 C5 C12 115.89(14) . .
C4 C5 C12 124.51(13) . .
C7 C6 C5 121.39(16) . .
C7 C6 H7 119.3 . .
C5 C6 H7 119.3 . .
C6 C7 C8 119.59(16) . .
C6 C7 H8 120.2 . .
C8 C7 H8 120.2 . .
C7 C8 C9 119.69(17) . .
C7 C8 H9 120.2 . .
C9 C8 H9 120.2 . .
C4 C9 C8 121.91(16) . .
C4 C9 H10 119.0 . .
C8 C9 H10 119.0 . .
C1 C10 H16A 109.5 . .
C1 C10 H16B 109.5 . .
H16A C10 H16B 109.5 . .
C1 C10 H16C 109.5 . .
H16A C10 H16C 109.5 . .
H16B C10 H16C 109.5 . .
C3 C11 H14A 109.5 . .
C3 C11 H14B 109.5 . .
H14A C11 H14B 109.5 . .
C3 C11 H14C 109.5 . .
H14A C11 H14C 109.5 . .
H14B C11 H14C 109.5 . .
O3 C12 O4A 122.5(2) . .
O3 C12 O4B 118.1(6) . .
O3 C12 C5 122.85(15) . .
O4A C12 C5 114.5(2) . .
O4B C12 C5 115.2(6) . .
C15A C16 H1A 109.5 . .
C15A C16 H1B 109.5 . .
H1A C16 H1B 109.5 . .
C15A C16 H1C 109.5 . .
H1A C16 H1C 109.5 . .
H1B C16 H1C 109.5 . .
C12 O4A C13A 116.1(3) . .
O4A C13A C14A 107.3(2) . .
O4A C13A H13A 110.3 . .
C14A C13A H13A 110.3 . .
O4A C13A H13B 110.3 . .
C14A C13A H13B 110.3 . .
H13A C13A H13B 108.5 . .
C13A C14A C15A 114.4(3) . .
C13A C14A H14D 108.7 . .
C15A C14A H14D 108.7 . .
C13A C14A H14E 108.7 . .
C15A C14A H14E 108.7 . .
H14D C14A H14E 107.6 . .
C14A C15A C16 110.8(3) . .
C14A C15A H15A 109.5 . .
C16 C15A H15A 109.5 . .
C14A C15A H15B 109.5 . .
C16 C15A H15B 109.5 . .
H15A C15A H15B 108.1 . .
C12 O4B C13B 119.4(9) . .
O4B C13B C14B 108.9(8) . .
O4B C13B H13C 109.9 . .
C14B C13B H13C 109.9 . .
O4B C13B H13D 109.9 . .
C14B C13B H13D 109.9 . .
H13C C13B H13D 108.3 . .
C13B C14B C15B 113.0(8) . .
C13B C14B H14F 109.0 . .
C15B C14B H14F 109.0 . .
C13B C14B H14G 109.0 . .
C15B C14B H14G 109.0 . .
H14F C14B H14G 107.8 . .
C16 C15B C14B 107.6(8) . .
C16 C15B H15C 110.2 . .
C14B C15B H15C 110.2 . .
C16 C15B H15D 110.2 . .
C14B C15B H15D 110.2 . .
H15C C15B H15D 108.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.4200(14) .
S1 O2 1.4297(13) .
S1 N2 1.6031(16) .
S1 N1 1.6458(16) .
N1 C1 1.365(2) .
N1 H1D 0.82(2) .
C1 C2 1.369(2) .
C1 C10 1.487(2) .
N2 C3 1.320(2) .
C2 C3 1.424(2) .
C2 C4 1.502(2) .
O3 C12 1.2170(19) .
C3 C11 1.503(2) .
C4 C9 1.390(2) .
C4 C5 1.411(2) .
C5 C6 1.401(2) .
C5 C12 1.489(2) .
C6 C7 1.373(3) .
C6 H7 0.9500 .
C7 C8 1.383(3) .
C7 H8 0.9500 .
C8 C9 1.393(2) .
C8 H9 0.9500 .
C9 H10 0.9500 .
C10 H16A 0.9800 .
C10 H16B 0.9800 .
C10 H16C 0.9800 .
C11 H14A 0.9800 .
C11 H14B 0.9800 .
C11 H14C 0.9800 .
C12 O4A 1.320(4) .
C12 O4B 1.387(13) .
C16 C15B 1.498(10) .
C16 C15A 1.543(4) .
C16 H1A 0.9800 .
C16 H1B 0.9800 .
C16 H1C 0.9800 .
O4A C13A 1.466(4) .
C13A C14A 1.503(4) .
C13A H13A 0.9900 .
C13A H13B 0.9900 .
C14A C15A 1.519(4) .
C14A H14D 0.9900 .
C14A H14E 0.9900 .
C15A H15A 0.9900 .
C15A H15B 0.9900 .
O4B C13B 1.482(16) .
C13B C14B 1.511(13) .
C13B H13C 0.9900 .
C13B H13D 0.9900 .
C14B C15B 1.527(12) .
C14B H14F 0.9900 .
C14B H14G 0.9900 .
C15B H15C 0.9900 .
C15B H15D 0.9900 .
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{9f50d681-4f2b-4223-9cd1-e186ce55bc96} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_cif.paper_type
EE
