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#$Date: 2019-11-04 14:04:35 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222960 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/44/4034442.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_4034442
loop_
_publ_author_name
'Padmaja, Ramsingh Dhanbahadur'
'Balamurali, Musuvathi Motilal'
'Chanda, Kaushik'
_publ_section_title
;
 One-Pot, Telescopic Approach for the Chemoselective Synthesis of
 Substituted
 Benzo[e]pyrido/pyrazino/pyridazino[1,2-b][1,2,4]thiadiazine
 dioxides and Their Significance in Biological Systems †.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11382
_journal_page_last               11390
_journal_paper_doi               10.1021/acs.joc.9b00869
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C12 H9 Cl N2 O2 S'
_chemical_formula_sum            'C12 H9 Cl N2 O2 S'
_chemical_formula_weight         280.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 115.119(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4847(6)
_cell_length_b                   7.9336(4)
_cell_length_c                   13.1642(6)
_cell_measurement_reflns_used    6586
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.05
_cell_measurement_theta_min      3.08
_cell_volume                     1180.58(10)
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0208
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10799
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.065
_diffrn_reflns_theta_min         3.084
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.494
_exptl_absorpt_correction_T_max  0.918
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       0.036(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2874
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0389
_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)+(0.0616P)²+0.3500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1108
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2523
_reflns_number_total             2874
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b00869_si_002.cif
_cod_data_source_block           Pdsc_18
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4034442
_shelx_shelxl_version_number     2016/6
_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   0.895
_shelx_estimated_absorpt_t_max   0.921
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.69746(13) 0.51922(19) 0.86087(11) 0.0326(3) Uani 1 1 d . .
C2 C 0.58572(15) 0.4424(2) 0.80619(15) 0.0420(4) Uani 1 1 d . .
C3 C 0.54594(19) 0.3894(3) 0.69705(16) 0.0545(5) Uani 1 1 d . .
H3 H 0.471408 0.340896 0.660609 0.065 Uiso 1 1 calc R U
C4 C 0.6177(2) 0.4087(2) 0.64182(15) 0.0564(5) Uani 1 1 d . .
H4 H 0.591115 0.371345 0.568160 0.068 Uiso 1 1 calc R U
C5 C 0.72729(18) 0.4817(2) 0.69322(13) 0.0480(4) Uani 1 1 d . .
H5 H 0.774108 0.491542 0.654276 0.058 Uiso 1 1 calc R U
C6 C 0.77010(14) 0.54219(19) 0.80418(12) 0.0342(3) Uani 1 1 d . .
C7 C 0.92697(13) 0.67870(18) 0.94840(12) 0.0315(3) Uani 1 1 d . .
C8 C 1.03837(14) 0.76419(19) 0.98773(14) 0.0379(3) Uani 1 1 d . .
H8 H 1.074899 0.773490 0.939386 0.045 Uiso 1 1 calc R U
C9 C 1.09324(14) 0.8321(2) 1.09135(15) 0.0405(4) Uani 1 1 d . .
C10 C 1.03742(16) 0.8162(2) 1.16560(14) 0.0456(4) Uani 1 1 d . .
H10 H 1.073354 0.861624 1.237410 0.055 Uiso 1 1 calc R U
C11 C 0.93417(15) 0.7366(2) 1.13271(13) 0.0412(4) Uani 1 1 d . .
H11 H 0.899060 0.726957 1.182198 0.049 Uiso 1 1 calc R U
C12 C 1.20957(18) 0.9215(2) 1.1296(2) 0.0567(5) Uani 1 1 d . .
H12A H 1.232145 0.928440 1.068471 0.085 Uiso 1 1 calc R U
H12B H 1.268737 0.860270 1.190470 0.085 Uiso 1 1 calc R U
H12C H 1.202375 1.033056 1.154225 0.085 Uiso 1 1 calc R U
Cl1 Cl 0.49624(4) 0.41005(7) 0.87515(5) 0.06039(18) Uani 1 1 d . .
N1 N 0.87759(10) 0.66739(16) 1.02535(10) 0.0318(3) Uani 1 1 d . .
N2 N 0.87910(12) 0.61905(17) 0.84654(11) 0.0366(3) Uani 1 1 d . .
O1 O 0.67329(11) 0.71440(18) 1.01049(11) 0.0526(4) Uani 1 1 d . .
O2 O 0.76551(12) 0.44031(17) 1.07239(10) 0.0505(3) Uani 1 1 d . .
S1 S 0.74379(3) 0.58110(5) 0.99920(3) 0.03277(14) 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'
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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 120.38(14)
C2 C1 S1 118.45(13)
C6 C1 S1 121.16(11)
C3 C2 C1 120.50(18)
C3 C2 Cl1 118.45(15)
C1 C2 Cl1 121.05(13)
C2 C3 C4 119.34(18)
C2 C3 H3 120.3
C4 C3 H3 120.3
C5 C4 C3 121.43(17)
C5 C4 H4 119.3
C3 C4 H4 119.3
C4 C5 C6 121.02(19)
C4 C5 H5 119.5
C6 C5 H5 119.5
N2 C6 C5 116.48(15)
N2 C6 C1 126.23(13)
C5 C6 C1 117.30(15)
N2 C7 N1 124.96(14)
N2 C7 C8 119.64(14)
N1 C7 C8 115.39(13)
C9 C8 C7 123.50(15)
C9 C8 H8 118.2
C7 C8 H8 118.2
C8 C9 C10 118.06(15)
C8 C9 C12 122.09(18)
C10 C9 C12 119.85(17)
C11 C10 C9 120.41(15)
C11 C10 H10 119.8
C9 C10 H10 119.8
C10 C11 N1 121.29(15)
C10 C11 H11 119.4
N1 C11 H11 119.4
C9 C12 H12A 109.5
C9 C12 H12B 109.5
H12A C12 H12B 109.5
C9 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C7 N1 C11 121.35(13)
C7 N1 S1 125.33(10)
C11 N1 S1 113.25(11)
C7 N2 C6 121.39(13)
O1 S1 O2 117.44(9)
O1 S1 N1 106.12(7)
O2 S1 N1 106.88(7)
O1 S1 C1 112.04(7)
O2 S1 C1 111.83(8)
N1 S1 C1 100.83(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.408(2)
C1 C6 1.410(2)
C1 S1 1.7313(14)
C2 C3 1.372(3)
C2 Cl1 1.732(2)
C3 C4 1.381(3)
C3 H3 0.9300
C4 C5 1.371(3)
C4 H4 0.9300
C5 C6 1.409(2)
C5 H5 0.9300
C6 N2 1.375(2)
C7 N2 1.3034(19)
C7 N1 1.3944(18)
C7 C8 1.432(2)
C8 C9 1.352(2)
C8 H8 0.9300
C9 C10 1.427(3)
C9 C12 1.498(2)
C10 C11 1.332(3)
C10 H10 0.9300
C11 N1 1.3966(19)
C11 H11 0.9300
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
N1 S1 1.6999(13)
O1 S1 1.4234(12)
O2 S1 1.4240(12)
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 C1 C2 C3 -0.2(2)
S1 C1 C2 C3 -179.17(14)
C6 C1 C2 Cl1 178.96(12)
S1 C1 C2 Cl1 -0.02(19)
C1 C2 C3 C4 1.4(3)
Cl1 C2 C3 C4 -177.77(15)
C2 C3 C4 C5 -0.9(3)
C3 C4 C5 C6 -0.9(3)
C4 C5 C6 N2 -177.59(16)
C4 C5 C6 C1 2.1(3)
C2 C1 C6 N2 178.12(15)
S1 C1 C6 N2 -2.9(2)
C2 C1 C6 C5 -1.5(2)
S1 C1 C6 C5 177.43(12)
N2 C7 C8 C9 178.92(14)
N1 C7 C8 C9 -0.7(2)
C7 C8 C9 C10 0.6(2)
C7 C8 C9 C12 -179.69(15)
C8 C9 C10 C11 -0.1(3)
C12 C9 C10 C11 -179.82(17)
C9 C10 C11 N1 -0.2(3)
N2 C7 N1 C11 -179.23(15)
C8 C7 N1 C11 0.4(2)
N2 C7 N1 S1 -2.6(2)
C8 C7 N1 S1 177.02(11)
C10 C11 N1 C7 0.1(2)
C10 C11 N1 S1 -176.96(14)
N1 C7 N2 C6 2.2(2)
C8 C7 N2 C6 -177.36(14)
C5 C6 N2 C7 -179.70(15)
C1 C6 N2 C7 0.6(2)
C7 N1 S1 O1 -116.61(13)
C11 N1 S1 O1 60.26(13)
C7 N1 S1 O2 117.31(13)
C11 N1 S1 O2 -65.82(13)
C7 N1 S1 C1 0.32(14)
C11 N1 S1 C1 177.19(11)
C2 C1 S1 O1 -66.41(15)
C6 C1 S1 O1 114.61(13)
C2 C1 S1 O2 67.83(14)
C6 C1 S1 O2 -111.15(13)
C2 C1 S1 N1 -178.90(12)
C6 C1 S1 N1 2.12(14)
