#------------------------------------------------------------------------------
#$Date: 2020-07-09 07:18:59 +0300 (Thu, 09 Jul 2020) $
#$Revision: 254126 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/85/4038560.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_4038560
loop_
_publ_author_name
'Honnanayakanavar, Jyoti M.'
'Harish, Battu'
'Nanubolu, Jagadeesh Babu'
'Suresh, Surisetti'
_publ_section_title
;
 Tandem Copper-Catalyzed Regioselective N-Arylation-Aza-Michael
 Addition: Synthesis of Tetracyclic
 5H-Benzothiazolo[3,2-a]quinazoline Derivatives.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00275
_journal_year                    2020
_chemical_formula_moiety         'C17 H15 N3 O2 S'
_chemical_formula_sum            'C17 H15 N3 O2 S'
_chemical_formula_weight         325.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 104.478(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   36.176(5)
_cell_length_b                   5.6425(8)
_cell_length_c                   15.396(2)
_cell_measurement_reflns_used    1743
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.113
_cell_measurement_theta_min      3.115
_cell_volume                     3042.9(7)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1145
_diffrn_reflns_av_unetI/netI     0.1388
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9395
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.689
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_description       plate
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.960
_refine_ls_R_factor_all          0.1546
_refine_ls_R_factor_gt           0.0652
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1481
_refine_ls_wR_factor_ref         0.1902
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1437
_reflns_number_total             2681
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00275_si_005.cif
_cod_data_source_block           KA714_0m
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4038560
_shelx_shelxl_version_number     2018/3
_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   0.923
_shelx_estimated_absorpt_t_max   0.978
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C1 C 0.39089(12) 0.9522(7) 0.2984(3) 0.0389(11) Uani 1 1 d . . . . .
C2 C 0.40189(13) 1.1516(7) 0.2596(3) 0.0432(12) Uani 1 1 d . . . . .
H2 H 0.385222 1.224203 0.211064 0.052 Uiso 1 1 calc R U . . .
C3 C 0.43795(15) 1.2412(8) 0.2940(3) 0.0495(13) Uani 1 1 d . . . . .
H3 H 0.445828 1.375393 0.268410 0.059 Uiso 1 1 calc R U . . .
C4 C 0.46255(14) 1.1326(8) 0.3663(3) 0.0500(13) Uani 1 1 d . . . . .
H4 H 0.487061 1.192848 0.387940 0.060 Uiso 1 1 calc R U . . .
C5 C 0.45136(12) 0.9350(7) 0.4075(3) 0.0435(12) Uani 1 1 d . . . . .
H5 H 0.468037 0.864413 0.456529 0.052 Uiso 1 1 calc R U . . .
C6 C 0.41511(12) 0.8458(7) 0.3742(3) 0.0358(11) Uani 1 1 d . . . . .
C7 C 0.36004(12) 0.6036(7) 0.3544(3) 0.0370(11) Uani 1 1 d . . . . .
C8 C 0.34882(12) 0.2822(7) 0.4419(3) 0.0412(11) Uani 1 1 d . . . . .
H8 H 0.347827 0.121603 0.417248 0.049 Uiso 1 1 calc R U . . .
C9 C 0.41225(12) 0.5029(7) 0.4797(3) 0.0360(10) Uani 1 1 d . . . . .
C10 C 0.38921(12) 0.3186(7) 0.4967(3) 0.0367(11) Uani 1 1 d . . . . .
C11 C 0.40549(14) 0.1696(8) 0.5667(3) 0.0495(12) Uani 1 1 d . . . . .
H11 H 0.391486 0.042941 0.580310 0.059 Uiso 1 1 calc R U . . .
C12 C 0.44232(14) 0.2064(8) 0.6167(3) 0.0543(13) Uani 1 1 d . . . . .
H12 H 0.453529 0.105269 0.663557 0.065 Uiso 1 1 calc R U . . .
C13 C 0.46186(13) 0.3951(8) 0.5954(3) 0.0515(13) Uani 1 1 d . . . . .
H13 H 0.486576 0.421814 0.629762 0.062 Uiso 1 1 calc R U . . .
C14 C 0.31931(13) 0.2898(7) 0.4969(3) 0.0450(12) Uani 1 1 d . . . . .
H14A H 0.294438 0.256221 0.457453 0.054 Uiso 1 1 calc R U . . .
H14B H 0.325033 0.164472 0.541376 0.054 Uiso 1 1 calc R U . . .
C15 C 0.31699(12) 0.5201(7) 0.5441(3) 0.0379(11) Uani 1 1 d . . . . .
C16 C 0.28084(14) 0.7229(8) 0.6308(3) 0.0599(14) Uani 1 1 d . . . . .
H16A H 0.280485 0.867007 0.596265 0.072 Uiso 1 1 calc R U . . .
H16B H 0.301385 0.734327 0.684931 0.072 Uiso 1 1 calc R U . . .
C17 C 0.24408(16) 0.6910(11) 0.6538(4) 0.0838(18) Uani 1 1 d . . . . .
H17A H 0.223975 0.681057 0.599826 0.126 Uiso 1 1 calc R U . . .
H17B H 0.239518 0.823483 0.688911 0.126 Uiso 1 1 calc R U . . .
H17C H 0.244752 0.547788 0.687845 0.126 Uiso 1 1 calc R U . . .
N1 N 0.39698(9) 0.6531(5) 0.4063(2) 0.0363(9) Uani 1 1 d . . . . .
N2 N 0.33712(10) 0.4418(6) 0.3650(2) 0.0428(10) Uani 1 1 d . . . . .
N3 N 0.44732(10) 0.5453(6) 0.5274(2) 0.0445(10) Uani 1 1 d . . . . .
O1 O 0.33898(9) 0.6825(5) 0.5522(2) 0.0520(9) Uani 1 1 d . . . . .
O2 O 0.28647(8) 0.5181(5) 0.5784(2) 0.0523(9) Uani 1 1 d . . . . .
S1 S 0.34702(3) 0.8054(2) 0.26476(8) 0.0494(4) 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'
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
_geom_angle_publ_flag
C2 C1 C6 121.4(4) . . ?
C2 C1 S1 126.6(3) . . ?
C6 C1 S1 112.0(3) . . ?
C3 C2 C1 118.8(4) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 120.3(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 121.3(4) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 118.8(4) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C1 119.3(4) . . ?
C5 C6 N1 129.0(4) . . ?
C1 C6 N1 111.7(4) . . ?
N2 C7 N1 129.0(4) . . ?
N2 C7 S1 120.7(3) . . ?
N1 C7 S1 110.4(3) . . ?
N2 C8 C10 114.4(4) . . ?
N2 C8 C14 109.4(3) . . ?
C10 C8 C14 113.8(4) . . ?
N2 C8 H8 106.2 . . ?
C10 C8 H8 106.2 . . ?
C14 C8 H8 106.2 . . ?
N3 C9 C10 124.5(4) . . ?
N3 C9 N1 117.8(4) . . ?
C10 C9 N1 117.7(4) . . ?
C11 C10 C9 116.2(4) . . ?
C11 C10 C8 121.3(4) . . ?
C9 C10 C8 122.5(4) . . ?
C12 C11 C10 120.7(4) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 118.1(4) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
N3 C13 C12 123.6(4) . . ?
N3 C13 H13 118.2 . . ?
C12 C13 H13 118.2 . . ?
C15 C14 C8 115.2(4) . . ?
C15 C14 H14A 108.5 . . ?
C8 C14 H14A 108.5 . . ?
C15 C14 H14B 108.5 . . ?
C8 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
O1 C15 O2 123.9(4) . . ?
O1 C15 C14 126.5(4) . . ?
O2 C15 C14 109.6(4) . . ?
O2 C16 C17 107.3(4) . . ?
O2 C16 H16A 110.3 . . ?
C17 C16 H16A 110.3 . . ?
O2 C16 H16B 110.3 . . ?
C17 C16 H16B 110.3 . . ?
H16A C16 H16B 108.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C7 N1 C9 117.6(3) . . ?
C7 N1 C6 114.3(3) . . ?
C9 N1 C6 128.0(3) . . ?
C7 N2 C8 118.6(3) . . ?
C9 N3 C13 116.9(4) . . ?
C15 O2 C16 117.2(3) . . ?
C1 S1 C7 91.7(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.378(6) . ?
C1 C6 1.406(5) . ?
C1 S1 1.750(4) . ?
C2 C3 1.376(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(6) . ?
C5 H5 0.9300 . ?
C6 N1 1.421(5) . ?
C7 N2 1.271(5) . ?
C7 N1 1.403(5) . ?
C7 S1 1.760(4) . ?
C8 N2 1.464(5) . ?
C8 C10 1.507(6) . ?
C8 C14 1.520(6) . ?
C8 H8 0.9800 . ?
C9 N3 1.319(5) . ?
C9 C10 1.398(6) . ?
C9 N1 1.410(5) . ?
C10 C11 1.377(6) . ?
C11 C12 1.378(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.362(6) . ?
C12 H12 0.9300 . ?
C13 N3 1.348(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.502(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O1 1.199(4) . ?
C15 O2 1.337(5) . ?
C16 O2 1.453(5) . ?
C16 C17 1.470(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 2.7(6) . . . . ?
S1 C1 C2 C3 -178.7(3) . . . . ?
C1 C2 C3 C4 -0.2(7) . . . . ?
C2 C3 C4 C5 -1.5(7) . . . . ?
C3 C4 C5 C6 0.7(7) . . . . ?
C4 C5 C6 C1 1.7(6) . . . . ?
C4 C5 C6 N1 -177.7(4) . . . . ?
C2 C1 C6 C5 -3.5(6) . . . . ?
S1 C1 C6 C5 177.7(3) . . . . ?
C2 C1 C6 N1 176.0(4) . . . . ?
S1 C1 C6 N1 -2.8(4) . . . . ?
N3 C9 C10 C11 -2.1(6) . . . . ?
N1 C9 C10 C11 177.5(4) . . . . ?
N3 C9 C10 C8 178.0(4) . . . . ?
N1 C9 C10 C8 -2.3(6) . . . . ?
N2 C8 C10 C11 -174.5(4) . . . . ?
C14 C8 C10 C11 58.8(5) . . . . ?
N2 C8 C10 C9 5.4(6) . . . . ?
C14 C8 C10 C9 -121.3(4) . . . . ?
C9 C10 C11 C12 0.8(6) . . . . ?
C8 C10 C11 C12 -179.4(4) . . . . ?
C10 C11 C12 C13 0.7(7) . . . . ?
C11 C12 C13 N3 -1.1(8) . . . . ?
N2 C8 C14 C15 -67.9(4) . . . . ?
C10 C8 C14 C15 61.4(5) . . . . ?
C8 C14 C15 O1 -10.5(6) . . . . ?
C8 C14 C15 O2 170.5(3) . . . . ?
N2 C7 N1 C9 1.8(6) . . . . ?
S1 C7 N1 C9 -178.3(3) . . . . ?
N2 C7 N1 C6 178.7(4) . . . . ?
S1 C7 N1 C6 -1.3(4) . . . . ?
N3 C9 N1 C7 178.4(3) . . . . ?
C10 C9 N1 C7 -1.3(5) . . . . ?
N3 C9 N1 C6 1.9(6) . . . . ?
C10 C9 N1 C6 -177.8(4) . . . . ?
C5 C6 N1 C7 -177.9(4) . . . . ?
C1 C6 N1 C7 2.6(5) . . . . ?
C5 C6 N1 C9 -1.4(7) . . . . ?
C1 C6 N1 C9 179.2(4) . . . . ?
N1 C7 N2 C8 1.6(7) . . . . ?
S1 C7 N2 C8 -178.3(3) . . . . ?
C10 C8 N2 C7 -4.9(5) . . . . ?
C14 C8 N2 C7 124.1(4) . . . . ?
C10 C9 N3 C13 1.8(6) . . . . ?
N1 C9 N3 C13 -177.9(4) . . . . ?
C12 C13 N3 C9 -0.2(7) . . . . ?
O1 C15 O2 C16 -2.2(6) . . . . ?
C14 C15 O2 C16 176.8(3) . . . . ?
C17 C16 O2 C15 174.8(4) . . . . ?
C2 C1 S1 C7 -177.0(4) . . . . ?
C6 C1 S1 C7 1.7(3) . . . . ?
N2 C7 S1 C1 179.7(4) . . . . ?
N1 C7 S1 C1 -0.2(3) . . . . ?
