#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:20:56 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180501 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/70/7217005.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_7217005
loop_
_publ_author_name
'Reddy, Alla Siva'
'Reddy, M. Nagarjuna'
'Swamy, K. C. Kumara'
_publ_section_title
;
 A simple copper-catalysed tandem cyclisation of ynamides leading to
 triazolo-1,2,4-benzothiadiazine-1,1-dioxides in PEG-400 medium
;
_journal_issue                   54
_journal_name_full               'RSC Advances'
_journal_page_first              28359
_journal_paper_doi               10.1039/c4ra03503h
_journal_volume                  4
_journal_year                    2014
_chemical_formula_sum            'C18 H18 N2 O5 S'
_chemical_formula_weight         374.40
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 97.179(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3978(17)
_cell_length_b                   19.453(4)
_cell_length_c                   9.6211(19)
_cell_measurement_reflns_used    1680
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      70.3480
_cell_measurement_theta_min      4.2990
_cell_volume                     1930.8(6)
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_collection       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0698
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6419
_diffrn_reflns_theta_full        71.49
_diffrn_reflns_theta_max         71.49
_diffrn_reflns_theta_min         4.29
_exptl_absorpt_coefficient_mu    1.754
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, Oxford Diffraction Ltd.'
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3614
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0622
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1607P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1826
_refine_ls_wR_factor_ref         0.2664
_reflns_number_gt                2152
_reflns_number_total             3614
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra03503h2.cif
_cod_data_source_block           kck21
_cod_original_cell_volume        1930.7(6)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7217005
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
C9 C 0.8336(4) 0.1324(2) -0.0198(4) 0.0370(9) Uani 1 1 d .
C10 C 0.9375(4) 0.1069(2) 0.0685(5) 0.0445(11) Uani 1 1 d .
H10 H 1.0139 0.1322 0.0847 0.053 Uiso 1 1 calc R
C6 C 1.0492(4) 0.3262(2) -0.0599(5) 0.0395(10) Uani 1 1 d .
C11 C 0.9282(5) 0.0433(3) 0.1337(5) 0.0516(12) Uani 1 1 d .
C14 C 0.7190(4) 0.0955(2) -0.0435(5) 0.0438(10) Uani 1 1 d .
C13 C 0.7104(5) 0.0318(3) 0.0194(7) 0.0602(14) Uani 1 1 d .
H13 H 0.6350 0.0059 0.0006 0.072 Uiso 1 1 calc R
C1 C 1.1097(5) 0.3589(3) 0.0576(6) 0.0586(14) Uani 1 1 d .
H1 H 1.0606 0.3774 0.1228 0.070 Uiso 1 1 calc R
C17 C 1.0412(6) 0.0165(3) 0.2341(6) 0.0682(16) Uani 1 1 d .
H17A H 1.1169 0.0437 0.2256 0.102 Uiso 1 1 calc R
H17B H 1.0579 -0.0305 0.2119 0.102 Uiso 1 1 calc R
H17C H 1.0204 0.0193 0.3284 0.102 Uiso 1 1 calc R
C12 C 0.8139(5) 0.0065(3) 0.1103(7) 0.0656(15) Uani 1 1 d .
H12 H 0.8062 -0.0353 0.1556 0.079 Uiso 1 1 calc R
C5 C 1.1234(4) 0.2964(3) -0.1540(6) 0.0568(13) Uani 1 1 d .
H5 H 1.0836 0.2731 -0.2322 0.068 Uiso 1 1 calc R
C4 C 1.2581(5) 0.3017(4) -0.1307(8) 0.081(2) Uani 1 1 d .
H4 H 1.3084 0.2819 -0.1934 0.097 Uiso 1 1 calc R
C3 C 1.3168(5) 0.3364(3) -0.0139(8) 0.0770(19) Uani 1 1 d .
H3 H 1.4066 0.3406 0.0008 0.092 Uiso 1 1 calc R
C2 C 1.2440(5) 0.3640(3) 0.0784(7) 0.0721(18) Uani 1 1 d .
H2 H 1.2842 0.3868 0.1571 0.087 Uiso 1 1 calc R
C7 C 0.9033(4) 0.3192(2) -0.0866(4) 0.0358(9) Uani 1 1 d .
H7 H 0.8753 0.3131 -0.1869 0.043 Uiso 1 1 calc R
C8 C 0.8660(3) 0.2564(2) -0.0051(4) 0.0345(9) Uani 1 1 d .
O3 O 0.8601(3) 0.25862(16) 0.1211(3) 0.0478(8) Uani 1 1 d .
O4 O 0.8461(3) 0.37998(15) -0.0363(3) 0.0428(7) Uani 1 1 d .
O5 O 0.6515(3) 0.3355(2) -0.1106(4) 0.0596(10) Uani 1 1 d .
C15 C 0.7149(4) 0.3826(3) -0.0621(5) 0.0473(11) Uani 1 1 d .
C16 C 0.6635(5) 0.4516(3) -0.0281(8) 0.0727(17) Uani 1 1 d .
H16A H 0.6276 0.4740 -0.1131 0.109 Uiso 1 1 calc R
H16B H 0.7327 0.4790 0.0184 0.109 Uiso 1 1 calc R
H16C H 0.5973 0.4460 0.0321 0.109 Uiso 1 1 calc R
S1 S 0.58209(10) 0.12841(7) -0.15179(13) 0.0505(4) Uani 1 1 d .
O1 O 0.4849(3) 0.0768(2) -0.1600(4) 0.0720(12) Uani 1 1 d .
N2 N 0.8469(3) 0.19831(18) -0.0810(3) 0.0355(8) Uani 1 1 d .
H2A H 0.8426 0.2011 -0.1706 0.043 Uiso 1 1 calc R
O2 O 0.6237(3) 0.1546(2) -0.2777(4) 0.0651(11) Uani 1 1 d .
N1 N 0.5323(4) 0.1937(2) -0.0696(5) 0.0565(11) Uani 1 1 d .
H1A H 0.5318 0.2343 -0.1050 0.068 Uiso 1 1 calc R
C18 C 0.4879(7) 0.1815(4) 0.0673(7) 0.087(2) Uani 1 1 d .
H18A H 0.4318 0.1421 0.0615 0.131 Uiso 1 1 calc R
H18B H 0.4415 0.2211 0.0938 0.131 Uiso 1 1 calc R
H18C H 0.5614 0.1733 0.1361 0.131 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C14 C9 C10 120.4(4)
C14 C9 N2 121.6(4)
C10 C9 N2 117.9(4)
C9 C10 C11 120.1(4)
C1 C6 C5 119.6(4)
C1 C6 C7 121.7(4)
C5 C6 C7 118.6(4)
C12 C11 C10 119.6(5)
C12 C11 C17 120.4(5)
C10 C11 C17 120.0(5)
C9 C14 C13 119.5(4)
C9 C14 S1 121.3(4)
C13 C14 S1 119.2(3)
C12 C13 C14 120.3(5)
C6 C1 C2 120.0(5)
C11 C12 C13 120.1(5)
C6 C5 C4 119.6(5)
C3 C4 C5 119.9(6)
C2 C3 C4 120.1(5)
C3 C2 C1 120.9(6)
O4 C7 C6 108.5(3)
O4 C7 C8 110.1(3)
C6 C7 C8 107.4(3)
O3 C8 N2 123.1(4)
O3 C8 C7 121.8(4)
N2 C8 C7 115.0(4)
C15 O4 C7 114.8(3)
O5 C15 O4 122.5(4)
O5 C15 C16 125.6(4)
O4 C15 C16 111.9(4)
O1 S1 O2 119.6(2)
O1 S1 N1 108.3(2)
O2 S1 N1 106.5(2)
O1 S1 C14 106.9(2)
O2 S1 C14 108.7(2)
N1 S1 C14 106.2(2)
C8 N2 C9 123.1(3)
C18 N1 S1 117.9(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C9 C14 1.385(6)
C9 C10 1.381(6)
C9 N2 1.425(5)
C10 C11 1.395(7)
C6 C1 1.378(7)
C6 C5 1.388(6)
C6 C7 1.512(5)
C11 C12 1.383(7)
C11 C17 1.518(7)
C14 C13 1.387(7)
C14 S1 1.775(4)
C13 C12 1.389(8)
C1 C2 1.390(7)
C5 C4 1.394(7)
C4 C3 1.386(10)
C3 C2 1.349(9)
C7 O4 1.435(5)
C7 C8 1.528(6)
C8 O3 1.224(5)
C8 N2 1.346(5)
O4 C15 1.356(5)
O5 C15 1.190(6)
C15 C16 1.495(7)
S1 O1 1.420(4)
S1 O2 1.430(4)
S1 N1 1.615(5)
N1 C18 1.469(7)
