#------------------------------------------------------------------------------
#$Date: 2015-12-04 08:58:08 +0200 (Fri, 04 Dec 2015) $
#$Revision: 170722 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/34/7223423.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_7223423
loop_
_publ_author_name
'Shah, Tariq A.'
'Ahmad, Zubair'
'Mir, Niyaz A.'
'Muneer, Mohammad'
'Ahmad, Musheer'
'Rath, Nigam P.'
_publ_section_title
;
 One step synthesis of highly functionalized thiazolo[3,2-
 b][1,2,4]triazole, triazolo[1,5-a]pyrimidine and triazolo[3,4-
 b][1,3,4]thiadiazine†
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA21270G
_journal_year                    2015
_chemical_formula_moiety         'C13 H9 N3 O3 S'
_chemical_formula_sum            'C13 H9 N3 O3 S'
_chemical_formula_weight         287.29
_chemical_melting_point          451.5(5)
_chemical_name_systematic
'methyl 7-oxo-2-phenyl-7H-[1,2,4]triazolo[5,1-b][1,3]thiazine-5-carboxylate '
_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
;
2015-07-06 deposited with the CCDC.
2015-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.835(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1783(10)
_cell_length_b                   14.804(2)
_cell_length_c                   12.0251(19)
_cell_measurement_temperature    150(2)
_cell_volume                     1265.9(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Mercury 375/M CCD (Xta LAB mini)'
_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  0.0998
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13172
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_meas      1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             592.0
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile:methanol (2:1)'
_exptl_crystal_size_max          0.748
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.161
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2894
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0808P)²+0.2122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1456
_reflns_number_gt                2631
_reflns_number_total             2894
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c5ra21270g2.cif
_cod_data_source_block           datam
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '451-452' was changed to '451.5(5)' -
the average value was taken and precision was estimated.

'_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.

'_exptl_absorpt_correction_type' value 'None' changed to 'none'
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 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7223423
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
H4 H 0.295(4) 0.2705(19) 0.726(2) 0.062(8) Uiso 1 1 d .
S1 S 0.14078(6) 0.33638(3) 0.43758(3) 0.03020(17) Uani 1 1 d .
N1 N 0.29468(19) 0.46417(10) 0.58830(12) 0.0268(3) Uani 1 1 d .
N2 N 0.3391(2) 0.55457(10) 0.59273(12) 0.0285(3) Uani 1 1 d .
O1 O 0.18786(19) 0.13358(8) 0.64088(11) 0.0367(3) Uani 1 1 d .
O2 O 0.0796(2) 0.15145(9) 0.45737(12) 0.0428(4) Uani 1 1 d .
N3 N 0.19946(19) 0.51538(10) 0.41754(12) 0.0291(3) Uani 1 1 d .
O3 O 0.3993(2) 0.43688(9) 0.77318(12) 0.0455(4) Uani 1 1 d .
C6 C 0.2124(2) 0.44310(11) 0.48210(14) 0.0261(3) Uani 1 1 d .
C5 C 0.3266(2) 0.40680(12) 0.68337(14) 0.0304(4) Uani 1 1 d .
C8 C 0.2997(2) 0.67559(11) 0.45264(14) 0.0263(4) Uani 1 1 d .
C2 C 0.1463(2) 0.18034(12) 0.54763(16) 0.0316(4) Uani 1 1 d .
C4 C 0.2713(2) 0.31367(12) 0.66288(15) 0.0307(4) Uani 1 1 d .
C1 C 0.1942(2) 0.27873(11) 0.56396(14) 0.0276(4) Uani 1 1 d .
C7 C 0.2801(2) 0.58162(11) 0.48898(14) 0.0263(3) Uani 1 1 d .
C12 C 0.4033(3) 0.82873(12) 0.49352(16) 0.0345(4) Uani 1 1 d .
H12 H 0.4593 0.8715 0.5441 0.041 Uiso 1 1 calc R
C13 C 0.3837(2) 0.74019(12) 0.52795(14) 0.0292(4) Uani 1 1 d .
H13 H 0.4268 0.7238 0.6016 0.035 Uiso 1 1 calc R
C9 C 0.2342(2) 0.70099(13) 0.34216(14) 0.0306(4) Uani 1 1 d .
H9 H 0.1774 0.6586 0.2914 0.037 Uiso 1 1 calc R
C10 C 0.2542(2) 0.78978(14) 0.30883(16) 0.0355(4) Uani 1 1 d .
H10 H 0.2103 0.8067 0.2355 0.043 Uiso 1 1 calc R
C11 C 0.3391(3) 0.85353(13) 0.38359(18) 0.0370(4) Uani 1 1 d .
H11 H 0.3530 0.9127 0.3602 0.044 Uiso 1 1 calc R
C3 C 0.1556(4) 0.03657(13) 0.63107(19) 0.0484(5) Uani 1 1 d .
H3A H 0.1901 0.0086 0.7030 0.073 Uiso 1 1 calc R
H3B H 0.2304 0.0118 0.5781 0.073 Uiso 1 1 calc R
H3C H 0.0250 0.0254 0.6057 0.073 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 0.0033 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
C6 S1 C1 99.06(8)
C6 N1 N2 109.06(13)
C6 N1 C5 128.17(15)
N2 N1 C5 122.73(14)
C7 N2 N1 102.41(13)
C2 O1 C3 115.73(15)
C6 N3 C7 102.76(14)
N3 C6 N1 110.58(15)
N3 C6 S1 124.56(13)
N1 C6 S1 124.85(13)
O3 C5 N1 119.91(16)
O3 C5 C4 125.03(16)
N1 C5 C4 115.04(15)
C13 C8 C9 119.43(16)
C13 C8 C7 120.37(15)
C9 C8 C7 120.19(16)
O2 C2 O1 126.67(17)
O2 C2 C1 121.19(17)
O1 C2 C1 112.13(15)
C1 C4 C5 125.96(17)
C1 C4 H4 116.0(17)
C5 C4 H4 118.0(17)
C4 C1 C2 123.18(16)
C4 C1 S1 126.81(14)
C2 C1 S1 110.00(12)
N2 C7 N3 115.19(15)
N2 C7 C8 122.33(15)
N3 C7 C8 122.49(15)
C13 C12 C11 119.99(18)
C13 C12 H12 120.0
C11 C12 H12 120.0
C12 C13 C8 120.39(16)
C12 C13 H13 119.8
C8 C13 H13 119.8
C10 C9 C8 119.62(17)
C10 C9 H9 120.2
C8 C9 H9 120.2
C11 C10 C9 120.76(17)
C11 C10 H10 119.6
C9 C10 H10 119.6
C10 C11 C12 119.80(18)
C10 C11 H11 120.1
C12 C11 H11 120.1
O1 C3 H3A 109.5
O1 C3 H3B 109.5
H3A C3 H3B 109.5
O1 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C6 1.7238(17)
S1 C1 1.7396(18)
N1 C6 1.368(2)
N1 N2 1.375(2)
N1 C5 1.418(2)
N2 C7 1.324(2)
O1 C2 1.317(2)
O1 C3 1.457(2)
O2 C2 1.203(2)
N3 C6 1.318(2)
N3 C7 1.378(2)
O3 C5 1.218(2)
C5 C4 1.446(2)
C8 C13 1.396(2)
C8 C9 1.399(2)
C8 C7 1.471(2)
C2 C1 1.504(2)
C4 C1 1.345(2)
C4 H4 0.99(3)
C12 C13 1.388(2)
C12 C11 1.389(3)
C12 H12 0.9300
C13 H13 0.9300
C9 C10 1.387(3)
C9 H9 0.9300
C10 C11 1.386(3)
C10 H10 0.9300
C11 H11 0.9300
C3 H3A 0.9600
C3 H3B 0.9600
C3 H3C 0.9600
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 N1 N2 C7 0.15(16)
C5 N1 N2 C7 -177.62(14)
C7 N3 C6 N1 0.73(17)
C7 N3 C6 S1 -177.74(12)
N2 N1 C6 N3 -0.59(18)
C5 N1 C6 N3 177.03(15)
N2 N1 C6 S1 177.88(11)
C5 N1 C6 S1 -4.5(2)
C1 S1 C6 N3 -178.77(14)
C1 S1 C6 N1 2.98(15)
C6 N1 C5 O3 -178.68(16)
N2 N1 C5 O3 -1.4(3)
C6 N1 C5 C4 2.8(2)
N2 N1 C5 C4 -179.92(14)
C3 O1 C2 O2 2.5(3)
C3 O1 C2 C1 -176.71(16)
O3 C5 C4 C1 -178.62(18)
N1 C5 C4 C1 -0.2(3)
C5 C4 C1 C2 177.77(16)
C5 C4 C1 S1 -0.5(3)
O2 C2 C1 C4 -179.05(18)
O1 C2 C1 C4 0.2(2)
O2 C2 C1 S1 -0.5(2)
O1 C2 C1 S1 178.78(12)
C6 S1 C1 C4 -0.71(17)
C6 S1 C1 C2 -179.19(11)
N1 N2 C7 N3 0.33(17)
N1 N2 C7 C8 -179.49(13)
C6 N3 C7 N2 -0.68(18)
C6 N3 C7 C8 179.14(14)
C13 C8 C7 N2 0.3(2)
C9 C8 C7 N2 -179.67(14)
C13 C8 C7 N3 -179.51(14)
C9 C8 C7 N3 0.5(2)
C11 C12 C13 C8 0.0(3)
C9 C8 C13 C12 -0.4(2)
C7 C8 C13 C12 179.62(15)
C13 C8 C9 C10 0.3(2)
C7 C8 C9 C10 -179.74(15)
C8 C9 C10 C11 0.2(3)
C9 C10 C11 C12 -0.6(3)
C13 C12 C11 C10 0.5(3)
