#------------------------------------------------------------------------------
#$Date: 2015-12-04 08:58:08 +0200 (Fri, 04 Dec 2015) $
#$Revision: 170722 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/34/7223425.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_7223425
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         'C11 H7 N3 O S'
_chemical_formula_sum            'C11 H7 N3 O S'
_chemical_formula_weight         229.26
_chemical_melting_point          543
_chemical_name_systematic
'5-phenyl-7H-[1,2,4]triazolo[5,1-b][1,3]thiazin-7-one (49)'
_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_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2015-07-06 deposited with the CCDC.
2015-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.277(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9892(6)
_cell_length_b                   10.5036(10)
_cell_length_c                   13.4268(13)
_cell_measurement_reflns_used    6498
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.94
_cell_measurement_theta_min      2.49
_cell_volume                     955.24(15)
_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-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0815
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19126
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.052
_diffrn_reflns_theta_min         2.492
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_T_max  0.8623
_exptl_absorpt_correction_T_min  0.6408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'sadabs v2014/4'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             472
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0495
_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)+(0.0871P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1365
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2570
_reflns_number_total             3319
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ra21270g2.cif
_cod_data_source_block           r615
_cod_database_code               7223425
_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   0.925
_shelx_estimated_absorpt_t_max   0.971
_shelxl_version_number           2014/6
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
S1 S 0.86424(5) 0.52186(3) 0.59908(3) 0.01333(12) Uani 1 1 d . .
O1 O 0.52515(15) 0.86517(10) 0.64580(9) 0.0186(2) Uani 1 1 d . .
N1 N 0.79372(17) 0.77876(11) 0.60186(9) 0.0109(2) Uani 1 1 d . .
N2 N 0.87795(16) 0.89236(12) 0.58430(9) 0.0134(3) Uani 1 1 d . .
N3 N 1.06864(18) 0.72463(12) 0.55894(10) 0.0144(3) Uani 1 1 d . .
C1 C 0.91122(19) 0.68093(14) 0.58565(10) 0.0114(3) Uani 1 1 d . .
C2 C 1.0392(2) 0.85313(14) 0.55935(11) 0.0142(3) Uani 1 1 d . .
H2 H 1.1304 0.9114 0.5425 0.017 Uiso 1 1 calc R U
C3 C 0.6122(2) 0.76984(14) 0.63081(11) 0.0125(3) Uani 1 1 d . .
C4 C 0.54351(19) 0.64043(14) 0.63950(11) 0.0134(3) Uani 1 1 d . .
H4 H 0.4183 0.6330 0.6547 0.016 Uiso 1 1 calc R U
C5 C 0.63463(19) 0.52929(13) 0.62873(10) 0.0098(3) Uani 1 1 d . .
C6 C 0.54862(19) 0.40211(13) 0.63976(10) 0.0108(3) Uani 1 1 d . .
C7 C 0.3731(2) 0.39129(15) 0.67198(11) 0.0141(3) Uani 1 1 d . .
H7 H 0.3098 0.4659 0.6880 0.017 Uiso 1 1 calc R U
C8 C 0.2906(2) 0.27256(15) 0.68067(12) 0.0159(3) Uani 1 1 d . .
H8 H 0.1708 0.2666 0.7018 0.019 Uiso 1 1 calc R U
C9 C 0.3829(2) 0.16221(15) 0.65850(11) 0.0155(3) Uani 1 1 d . .
H9 H 0.3268 0.0812 0.6649 0.019 Uiso 1 1 calc R U
C10 C 0.5578(2) 0.17131(15) 0.62695(11) 0.0153(3) Uani 1 1 d . .
H10 H 0.6218 0.0964 0.6122 0.018 Uiso 1 1 calc R U
C11 C 0.6386(2) 0.29030(14) 0.61698(11) 0.0141(3) Uani 1 1 d . .
H11 H 0.7568 0.2958 0.5943 0.017 Uiso 1 1 calc R U
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
C1 S1 C5 100.96(7)
C1 N1 N2 109.00(11)
C1 N1 C3 127.40(12)
N2 N1 C3 123.60(11)
C2 N2 N1 101.60(12)
C1 N3 C2 101.88(12)
N3 C1 N1 110.84(13)
N3 C1 S1 123.99(11)
N1 C1 S1 125.17(11)
N2 C2 N3 116.68(13)
N2 C2 H2 121.7
N3 C2 H2 121.7
O1 C3 N1 120.64(13)
O1 C3 C4 124.61(13)
N1 C3 C4 114.75(12)
C5 C4 C3 128.54(13)
C5 C4 H4 115.7
C3 C4 H4 115.7
C4 C5 C6 123.46(13)
C4 C5 S1 123.03(11)
C6 C5 S1 113.51(10)
C11 C6 C7 118.25(13)
C11 C6 C5 121.13(12)
C7 C6 C5 120.62(13)
C8 C7 C6 120.71(14)
C8 C7 H7 119.6
C6 C7 H7 119.6
C7 C8 C9 120.28(14)
C7 C8 H8 119.9
C9 C8 H8 119.9
C10 C9 C8 119.70(14)
C10 C9 H9 120.2
C8 C9 H9 120.2
C11 C10 C9 119.91(14)
C11 C10 H10 120.0
C9 C10 H10 120.0
C10 C11 C6 121.15(14)
C10 C11 H11 119.4
C6 C11 H11 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.7208(15)
S1 C5 1.7479(14)
O1 C3 1.2140(17)
N1 C1 1.3659(18)
N1 N2 1.3764(17)
N1 C3 1.4185(18)
N2 C2 1.3186(18)
N3 C1 1.3208(18)
N3 C2 1.3655(19)
C2 H2 0.9500
C3 C4 1.456(2)
C4 C5 1.3545(19)
C4 H4 0.9500
C5 C6 1.4872(19)
C6 C11 1.4010(19)
C6 C7 1.4027(18)
C7 C8 1.391(2)
C7 H7 0.9500
C8 C9 1.394(2)
C8 H8 0.9500
C9 C10 1.392(2)
C9 H9 0.9500
C10 C11 1.392(2)
C10 H10 0.9500
C11 H11 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 N2 0.95 2.67 3.4282(19) 137.7 3_776
C4 H4 N3 0.95 2.65 3.3462(18) 130.9 1_455
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
C1 N1 N2 C2 -0.19(14)
C3 N1 N2 C2 -179.48(13)
C2 N3 C1 N1 -0.34(15)
C2 N3 C1 S1 -179.74(11)
N2 N1 C1 N3 0.35(16)
C3 N1 C1 N3 179.61(13)
N2 N1 C1 S1 179.75(10)
C3 N1 C1 S1 -1.0(2)
C5 S1 C1 N3 -177.41(12)
C5 S1 C1 N1 3.27(13)
N1 N2 C2 N3 -0.02(16)
C1 N3 C2 N2 0.23(16)
C1 N1 C3 O1 177.73(13)
N2 N1 C3 O1 -3.1(2)
C1 N1 C3 C4 -2.7(2)
N2 N1 C3 C4 176.45(12)
O1 C3 C4 C5 -176.78(15)
N1 C3 C4 C5 3.7(2)
C3 C4 C5 C6 179.87(13)
C3 C4 C5 S1 -0.8(2)
C1 S1 C5 C4 -2.39(14)
C1 S1 C5 C6 176.98(10)
C4 C5 C6 C11 173.01(13)
S1 C5 C6 C11 -6.35(17)
C4 C5 C6 C7 -6.1(2)
S1 C5 C6 C7 174.56(10)
C11 C6 C7 C8 -0.2(2)
C5 C6 C7 C8 178.90(13)
C6 C7 C8 C9 0.7(2)
C7 C8 C9 C10 -0.4(2)
C8 C9 C10 C11 -0.5(2)
C9 C10 C11 C6 1.0(2)
C7 C6 C11 C10 -0.7(2)
C5 C6 C11 C10 -179.77(13)
