#------------------------------------------------------------------------------
#$Date: 2020-07-09 07:18:34 +0300 (Thu, 09 Jul 2020) $
#$Revision: 254125 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/85/4038559.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_4038559
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         'C19 H18 N2 O2 S'
_chemical_formula_sum            'C19 H18 N2 O2 S'
_chemical_formula_weight         338.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                95.298(6)
_cell_angle_beta                 90.260(7)
_cell_angle_gamma                113.046(6)
_cell_formula_units_Z            2
_cell_length_a                   7.6361(15)
_cell_length_b                   8.1452(15)
_cell_length_c                   14.722(3)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.198
_cell_measurement_theta_min      2.732
_cell_volume                     838.2(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0384
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18274
_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         27.498
_diffrn_reflns_theta_min         2.732
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.267
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3855
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.267
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0449
_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          0.1537
_refine_ls_wR_factor_ref         0.1657
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3177
_reflns_number_total             3855
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00275_si_003.cif
_cod_data_source_block           KA540_0m
_cod_original_cell_volume        838.1(3)
_cod_database_code               4038559
_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   0.920
_shelx_estimated_absorpt_t_max   0.941
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.2097(2) 0.4659(2) 0.88982(11) 0.0368(4) Uani 1 1 d . . . . .
C2 C 0.0925(2) 0.3276(2) 0.93725(11) 0.0434(4) Uani 1 1 d . . . . .
H2 H 0.144849 0.277089 0.978213 0.052 Uiso 1 1 calc R U . . .
C3 C -0.1039(3) 0.2648(2) 0.92318(12) 0.0462(4) Uani 1 1 d . . . . .
C4 C -0.1770(3) 0.3413(2) 0.86032(13) 0.0486(4) Uani 1 1 d . . . . .
H4 H -0.308251 0.298062 0.849822 0.058 Uiso 1 1 calc R U . . .
C5 C -0.0603(2) 0.4805(2) 0.81253(12) 0.0441(4) Uani 1 1 d . . . . .
H5 H -0.112651 0.529108 0.770559 0.053 Uiso 1 1 calc R U . . .
C6 C 0.1356(2) 0.5456(2) 0.82860(10) 0.0360(4) Uani 1 1 d . . . . .
C7 C -0.2357(3) 0.1124(3) 0.97243(15) 0.0649(6) Uani 1 1 d . . . . .
H7A H -0.272360 0.002109 0.933411 0.097 Uiso 1 1 calc R U . . .
H7B H -0.347241 0.133955 0.988284 0.097 Uiso 1 1 calc R U . . .
H7C H -0.171540 0.104086 1.026957 0.097 Uiso 1 1 calc R U . . .
C8 C 0.4633(2) 0.6890(2) 0.80521(10) 0.0356(4) Uani 1 1 d . . . . .
C9 C 0.2723(2) 0.8388(2) 0.75543(10) 0.0349(3) Uani 1 1 d . . . . .
C10 C 0.1235(2) 0.8953(2) 0.77351(11) 0.0426(4) Uani 1 1 d . . . . .
H10 H 0.016306 0.824007 0.802455 0.051 Uiso 1 1 calc R U . . .
C11 C 0.1392(3) 1.0590(3) 0.74746(13) 0.0490(4) Uani 1 1 d . . . . .
H11 H 0.040997 1.097418 0.759112 0.059 Uiso 1 1 calc R U . . .
C12 C 0.2959(3) 1.1659(2) 0.70489(14) 0.0527(5) Uani 1 1 d . . . . .
H12 H 0.304080 1.276136 0.688427 0.063 Uiso 1 1 calc R U . . .
C13 C 0.4419(3) 1.1091(2) 0.68650(12) 0.0458(4) Uani 1 1 d . . . . .
H13 H 0.548161 1.181410 0.657352 0.055 Uiso 1 1 calc R U . . .
C14 C 0.4315(2) 0.9455(2) 0.71109(10) 0.0372(4) Uani 1 1 d . . . . .
C15 C 0.5848(2) 0.8751(2) 0.69205(11) 0.0386(4) Uani 1 1 d . . . . .
H15 H 0.703774 0.976795 0.683229 0.046 Uiso 1 1 calc R U . . .
C16 C 0.5331(2) 0.7449(2) 0.60444(12) 0.0453(4) Uani 1 1 d . . . . .
H16A H 0.410886 0.647899 0.610635 0.054 Uiso 1 1 calc R U . . .
H16B H 0.520717 0.807683 0.553482 0.054 Uiso 1 1 calc R U . . .
C17 C 0.6800(3) 0.6679(3) 0.58430(12) 0.0502(4) Uani 1 1 d . . . . .
N1 N 0.27862(17) 0.67948(17) 0.78529(9) 0.0352(3) Uani 1 1 d . . . . .
N2 N 0.61631(18) 0.78495(19) 0.76895(10) 0.0397(3) Uani 1 1 d . . . . .
O1 O 0.6612(3) 0.5174(2) 0.59118(14) 0.0851(5) Uani 1 1 d . . . . .
O2 O 0.8386(2) 0.7927(2) 0.55700(11) 0.0639(4) Uani 1 1 d . . . . .
S1 S 0.45937(6) 0.55152(6) 0.89124(3) 0.04486(19) Uani 1 1 d . . . . .
C18 C 1.0144(6) 0.7639(9) 0.5397(3) 0.0539(11) Uani 0.709(11) 1 d . . P A 1
H18A H 1.016627 0.667086 0.572863 0.065 Uiso 0.709(11) 1 calc R U P A 1
H18B H 1.124632 0.871735 0.560192 0.065 Uiso 0.709(11) 1 calc R U P A 1
C19 C 1.0193(7) 0.7177(7) 0.4400(3) 0.0576(12) Uani 0.709(11) 1 d . . P A 1
H19A H 1.022564 0.816286 0.408015 0.086 Uiso 0.709(11) 1 calc R U P A 1
H19B H 0.907653 0.613164 0.420057 0.086 Uiso 0.709(11) 1 calc R U P A 1
H19C H 1.130883 0.693878 0.427568 0.086 Uiso 0.709(11) 1 calc R U P A 1
C18D C 0.9446(16) 0.6763(15) 0.5252(7) 0.048(2) Uani 0.291(11) 1 d . . P A 2
H18C H 0.990998 0.634692 0.576164 0.057 Uiso 0.291(11) 1 calc R U P A 2
H18D H 0.866348 0.574218 0.483391 0.057 Uiso 0.291(11) 1 calc R U P A 2
C19D C 1.1028(16) 0.8074(18) 0.4786(10) 0.068(4) Uani 0.291(11) 1 d . . P A 2
H19D H 1.201023 0.762862 0.468392 0.101 Uiso 0.291(11) 1 calc R U P A 2
H19E H 1.153826 0.919844 0.516230 0.101 Uiso 0.291(11) 1 calc R U P A 2
H19F H 1.055761 0.824395 0.421164 0.101 Uiso 0.291(11) 1 calc R U P A 2
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 121.62(15) . . ?
C2 C1 S1 126.38(14) . . ?
C6 C1 S1 111.86(12) . . ?
C1 C2 C3 119.53(17) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 118.64(16) . . ?
C4 C3 C7 120.36(18) . . ?
C2 C3 C7 120.97(19) . . ?
C3 C4 C5 122.21(17) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C6 C5 C4 118.86(17) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C1 119.10(15) . . ?
C5 C6 N1 128.04(15) . . ?
C1 C6 N1 112.70(13) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 N1 126.48(14) . . ?
N2 C8 S1 122.87(12) . . ?
N1 C8 S1 110.64(11) . . ?
C14 C9 C10 120.32(15) . . ?
C14 C9 N1 115.99(13) . . ?
C10 C9 N1 123.56(15) . . ?
C11 C10 C9 118.62(16) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C12 C11 C10 121.58(16) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 119.63(17) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 120.64(17) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C9 119.20(15) . . ?
C13 C14 C15 123.21(14) . . ?
C9 C14 C15 117.59(14) . . ?
N2 C15 C14 111.42(12) . . ?
N2 C15 C16 109.75(13) . . ?
C14 C15 C16 110.60(13) . . ?
N2 C15 H15 108.3 . . ?
C14 C15 H15 108.3 . . ?
C16 C15 H15 108.3 . . ?
C17 C16 C15 112.29(14) . . ?
C17 C16 H16A 109.1 . . ?
C15 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.9 . . ?
O1 C17 O2 123.62(19) . . ?
O1 C17 C16 126.01(19) . . ?
O2 C17 C16 110.38(15) . . ?
C8 N1 C6 113.13(13) . . ?
C8 N1 C9 114.70(13) . . ?
C6 N1 C9 127.71(13) . . ?
C8 N2 C15 113.80(13) . . ?
C17 O2 C18 123.6(3) . . ?
C17 O2 C18D 99.8(5) . . ?
C1 S1 C8 91.09(7) . . ?
O2 C18 C19 108.2(3) . . ?
O2 C18 H18A 110.1 . . ?
C19 C18 H18A 110.1 . . ?
O2 C18 H18B 110.1 . . ?
C19 C18 H18B 110.1 . . ?
H18A C18 H18B 108.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C19D C18D O2 99.9(8) . . ?
C19D C18D H18C 111.8 . . ?
O2 C18D H18C 111.8 . . ?
C19D C18D H18D 111.8 . . ?
O2 C18D H18D 111.8 . . ?
H18C C18D H18D 109.5 . . ?
C18D C19D H19D 109.5 . . ?
C18D C19D H19E 109.5 . . ?
H19D C19D H19E 109.5 . . ?
C18D C19D H19F 109.5 . . ?
H19D C19D H19F 109.5 . . ?
H19E C19D H19F 109.5 . . ?
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 1.386(2) . ?
C1 C6 1.395(2) . ?
C1 S1 1.7540(16) . ?
C2 C3 1.389(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(3) . ?
C3 C7 1.508(3) . ?
C4 C5 1.392(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(2) . ?
C5 H5 0.9300 . ?
C6 N1 1.411(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 N2 1.276(2) . ?
C8 N1 1.4099(19) . ?
C8 S1 1.7592(16) . ?
C9 C14 1.394(2) . ?
C9 C10 1.401(2) . ?
C9 N1 1.426(2) . ?
C10 C11 1.382(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.385(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.509(2) . ?
C15 N2 1.472(2) . ?
C15 C16 1.536(2) . ?
C15 H15 0.9800 . ?
C16 C17 1.504(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O1 1.191(2) . ?
C17 O2 1.333(2) . ?
O2 C18 1.470(3) . ?
O2 C18D 1.515(7) . ?
C18 C19 1.486(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C18D C19D 1.484(15) . ?
C18D H18C 0.9700 . ?
C18D H18D 0.9700 . ?
C19D H19D 0.9600 . ?
C19D H19E 0.9600 . ?
C19D H19F 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 0.7(2) . . . . ?
S1 C1 C2 C3 -174.66(13) . . . . ?
C1 C2 C3 C4 1.1(2) . . . . ?
C1 C2 C3 C7 178.98(16) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C7 C3 C4 C5 -179.16(17) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 2.1(3) . . . . ?
C4 C5 C6 N1 177.10(15) . . . . ?
C2 C1 C6 C5 -2.2(2) . . . . ?
S1 C1 C6 C5 173.69(12) . . . . ?
C2 C1 C6 N1 -178.02(14) . . . . ?
S1 C1 C6 N1 -2.09(17) . . . . ?
C14 C9 C10 C11 -0.7(2) . . . . ?
N1 C9 C10 C11 175.01(15) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 C9 -0.5(2) . . . . ?
C12 C13 C14 C15 179.30(16) . . . . ?
C10 C9 C14 C13 1.0(2) . . . . ?
N1 C9 C14 C13 -175.03(14) . . . . ?
C10 C9 C14 C15 -178.80(14) . . . . ?
N1 C9 C14 C15 5.1(2) . . . . ?
C13 C14 C15 N2 140.58(16) . . . . ?
C9 C14 C15 N2 -39.59(19) . . . . ?
C13 C14 C15 C16 -97.06(18) . . . . ?
C9 C14 C15 C16 82.77(17) . . . . ?
N2 C15 C16 C17 -55.19(18) . . . . ?
C14 C15 C16 C17 -178.52(14) . . . . ?
C15 C16 C17 O1 108.4(2) . . . . ?
C15 C16 C17 O2 -71.62(19) . . . . ?
N2 C8 N1 C6 172.88(15) . . . . ?
S1 C8 N1 C6 -8.48(16) . . . . ?
N2 C8 N1 C9 -28.9(2) . . . . ?
S1 C8 N1 C9 149.72(11) . . . . ?
C5 C6 N1 C8 -168.43(16) . . . . ?
C1 C6 N1 C8 6.88(19) . . . . ?
C5 C6 N1 C9 36.8(2) . . . . ?
C1 C6 N1 C9 -147.87(15) . . . . ?
C14 C9 N1 C8 28.02(18) . . . . ?
C10 C9 N1 C8 -147.90(16) . . . . ?
C14 C9 N1 C6 -177.56(14) . . . . ?
C10 C9 N1 C6 6.5(2) . . . . ?
N1 C8 N2 C15 -7.4(2) . . . . ?
S1 C8 N2 C15 174.08(11) . . . . ?
C14 C15 N2 C8 40.19(18) . . . . ?
C16 C15 N2 C8 -82.66(16) . . . . ?
O1 C17 O2 C18 -5.5(4) . . . . ?
C16 C17 O2 C18 174.5(2) . . . . ?
O1 C17 O2 C18D 9.9(5) . . . . ?
C16 C17 O2 C18D -170.1(4) . . . . ?
C2 C1 S1 C8 173.38(15) . . . . ?
C6 C1 S1 C8 -2.32(13) . . . . ?
N2 C8 S1 C1 -175.22(14) . . . . ?
N1 C8 S1 C1 6.08(12) . . . . ?
C17 O2 C18 C19 97.6(5) . . . . ?
C17 O2 C18D C19D 169.6(10) . . . . ?
