#------------------------------------------------------------------------------
#$Date: 2022-03-05 00:19:36 +0200 (Sat, 05 Mar 2022) $
#$Revision: 273390 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/11/7061172.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_7061172
loop_
_publ_author_name
'Shyamsivappan, Selvaraj'
'Vivek, Raju'
'Suresh, Thangaraj'
'Naveen, Palanivel'
'Kaviyarasu, Adhigaman'
'Amsaveni, Sundarasamy'
'Athimoolam, Shunmuganarayanan'
'Mohan, Palathurai Subramaniam'
_publ_section_title
;
 New
 N-(3′-acetyl-8-nitro-2,3-dihydro-1H,3′H-spiro[quinoline-4,2′-[1,3,4]thiadiazol]-5′-yl)
 acetamides induced cell death in MCF-7 cells via G2/M phase cell cycle
 arrest
;
_journal_issue                   6
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2817
_journal_page_last               2828
_journal_paper_doi               10.1039/D1NJ02550C
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C14 H15 N5 O4 S'
_chemical_formula_sum            'C14 H15 N5 O4 S'
_chemical_formula_weight         349.37
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2020-01-28 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   18.03(3)
_cell_length_b                   18.03(3)
_cell_length_c                   20.39(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.67
_cell_measurement_theta_min      2.36
_cell_volume                     6628(2)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-2014
_computing_structure_refinement  SHELXL-2014
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            28469
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.259
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             2912
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0440
_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)+(0.0580P)²+6.7829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1224
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2456
_reflns_number_total             2922
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj02550c2.cif
_cod_data_source_block           shelx_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7061170--7061176.cif.'
_cod_original_cell_volume        6627(26)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               7061172
_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.
;
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/4, x+3/4, z+3/4'
'y+1/4, -x+1/4, z+1/4'
'-x, -y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-y+3/4, x+5/4, z+5/4'
'y+3/4, -x+3/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'-x, -y, -z'
'y-1/4, -x-3/4, -z-3/4'
'-y-1/4, x-1/4, -z-1/4'
'x, y-1/2, -z'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/4, -x-1/4, -z-1/4'
'-y+1/4, x+1/4, -z+1/4'
'x+1/2, y, -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 0.77585(16) 0.5647(2) 0.4535(3) 0.1246(19) Uani 1 1 d . . . . .
H1A H 0.7972 0.5701 0.4106 0.187 Uiso 1 1 calc R U . . .
H1B H 0.7803 0.5140 0.4675 0.187 Uiso 1 1 calc R U . . .
H1C H 0.8015 0.5963 0.4839 0.187 Uiso 1 1 calc R U . . .
C2 C 0.69614(13) 0.58576(13) 0.45124(16) 0.0624(7) Uani 1 1 d . . . . .
C3 C 0.57397(11) 0.54099(10) 0.42160(10) 0.0364(5) Uani 1 1 d . . . . .
C4 C 0.44359(11) 0.58722(10) 0.40051(10) 0.0351(4) Uani 1 1 d . . . . .
C5 C 0.43095(12) 0.61722(11) 0.33254(11) 0.0415(5) Uani 1 1 d . . . . .
C6 C 0.38934(14) 0.68341(12) 0.32584(11) 0.0490(6) Uani 1 1 d . . . . .
C7 C 0.38255(19) 0.71105(15) 0.26102(14) 0.0739(9) Uani 1 1 d . . . . .
C10 C 0.46224(16) 0.58334(15) 0.27881(12) 0.0617(7) Uani 1 1 d . . . . .
H5 H 0.4901 0.5405 0.2848 0.074 Uiso 1 1 calc R U . . .
C11 C 0.4534(2) 0.61113(19) 0.21636(15) 0.0909(11) Uani 1 1 d . . . . .
H11 H 0.4742 0.5869 0.1805 0.109 Uiso 1 1 calc R U . . .
C12 C 0.4139(2) 0.67446(19) 0.20804(15) 0.0955(12) Uani 1 1 d . . . . .
H6 H 0.4078 0.6937 0.1661 0.115 Uiso 1 1 calc R U . . .
C14 C 0.36967(14) 0.69097(12) 0.44512(11) 0.0479(6) Uani 1 1 d . . . . .
H14A H 0.3267 0.7040 0.4714 0.057 Uiso 1 1 calc R U . . .
H14B H 0.4127 0.7153 0.4639 0.057 Uiso 1 1 calc R U . . .
C15 C 0.38070(12) 0.60800(11) 0.44657(11) 0.0440(5) Uani 1 1 d . . . . .
H8 H 0.3354 0.5833 0.4331 0.053 Uiso 1 1 calc R U . . .
H9 H 0.3925 0.5921 0.4908 0.053 Uiso 1 1 calc R U . . .
C16 C 0.40901(12) 0.45528(11) 0.38102(11) 0.0430(5) Uani 1 1 d . . . . .
C17 C 0.43384(14) 0.37688(12) 0.37816(14) 0.0546(6) Uani 1 1 d . . . . .
H12 H 0.3921 0.3455 0.3689 0.082 Uiso 1 1 calc R U . . .
H13 H 0.4552 0.3631 0.4195 0.082 Uiso 1 1 calc R U . . .
H14 H 0.4703 0.3714 0.3442 0.082 Uiso 1 1 calc R U . . .
N1 N 0.3421(2) 0.77856(16) 0.24800(16) 0.1092(12) Uani 1 1 d . . . . .
N2 N 0.35907(13) 0.71621(11) 0.37906(10) 0.0596(6) Uani 1 1 d . . . . .
H7 H 0.3317 0.7547 0.3730 0.072 Uiso 1 1 calc R U . . .
N3 N 0.45959(9) 0.50674(9) 0.40019(9) 0.0378(4) Uani 1 1 d . . . . .
N4 N 0.53375(9) 0.48537(9) 0.40646(9) 0.0368(4) Uani 1 1 d . . . . .
N5 N 0.64938(9) 0.53236(9) 0.42801(10) 0.0467(5) Uani 1 1 d . . . . .
H4 H 0.6683 0.4905 0.4166 0.056 Uiso 1 1 calc R U . . .
O3 O 0.34550(9) 0.47432(9) 0.36758(10) 0.0629(5) Uani 1 1 d . . . . .
O4 O 0.67336(10) 0.64550(9) 0.46913(12) 0.0788(7) Uani 1 1 d . . . . .
S1 S 0.53119(3) 0.62679(3) 0.43330(3) 0.0460(2) Uani 1 1 d . . . . .
O1 O 0.3168(2) 0.81527(15) 0.29331(15) 0.1303(12) Uani 1 1 d . . . . .
O2 O 0.3339(3) 0.79815(16) 0.19184(13) 0.1747(19) 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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O4 C2 N5 121.6(2) . . ?
O4 C2 C1 123.2(2) . . ?
N5 C2 C1 115.3(2) . . ?
N4 C3 N5 119.76(18) . . ?
N4 C3 S1 118.60(17) . . ?
N5 C3 S1 121.64(14) . . ?
N3 C4 C5 112.20(17) . . ?
N3 C4 C15 112.96(16) . . ?
C5 C4 C15 111.57(19) . . ?
N3 C4 S1 102.27(13) . . ?
C5 C4 S1 108.80(14) . . ?
C15 C4 S1 108.50(18) . . ?
C10 C5 C6 121.0(2) . . ?
C10 C5 C4 120.8(2) . . ?
C6 C5 C4 118.15(19) . . ?
N2 C6 C5 120.3(2) . . ?
N2 C6 C7 124.1(2) . . ?
C5 C6 C7 115.6(2) . . ?
C12 C7 C6 121.6(3) . . ?
C12 C7 N1 117.6(3) . . ?
C6 C7 N1 120.8(3) . . ?
C5 C10 C11 121.8(3) . . ?
C5 C10 H5 119.1 . . ?
C11 C10 H5 119.1 . . ?
C12 C11 C10 118.8(3) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C7 121.1(3) . . ?
C11 C12 H6 119.4 . . ?
C7 C12 H6 119.4 . . ?
N2 C14 C15 110.50(19) . . ?
N2 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 C4 109.30(17) . . ?
C14 C15 H8 109.8 . . ?
C4 C15 H8 109.8 . . ?
C14 C15 H9 109.8 . . ?
C4 C15 H9 109.8 . . ?
H8 C15 H9 108.3 . . ?
O3 C16 N3 120.0(2) . . ?
O3 C16 C17 122.64(19) . . ?
N3 C16 C17 117.35(19) . . ?
C16 C17 H12 109.5 . . ?
C16 C17 H13 109.5 . . ?
H12 C17 H13 109.5 . . ?
C16 C17 H14 109.5 . . ?
H12 C17 H14 109.5 . . ?
H13 C17 H14 109.5 . . ?
O2 N1 O1 120.8(3) . . ?
O2 N1 C7 118.9(3) . . ?
O1 N1 C7 120.4(3) . . ?
C6 N2 C14 124.2(2) . . ?
C6 N2 H7 117.9 . . ?
C14 N2 H7 117.9 . . ?
C16 N3 N4 118.71(17) . . ?
C16 N3 C4 122.70(17) . . ?
N4 N3 C4 117.17(15) . . ?
C3 N4 N3 110.45(17) . . ?
C2 N5 C3 124.34(19) . . ?
C2 N5 H4 117.8 . . ?
C3 N5 H4 117.8 . . ?
C3 S1 C4 89.20(12) . . ?
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 1.487(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O4 1.209(3) . ?
C2 N5 1.365(3) . ?
C3 N4 1.275(3) . ?
C3 N5 1.375(3) . ?
C3 S1 1.745(2) . ?
C4 N3 1.479(2) . ?
C4 C5 1.505(4) . ?
C4 C15 1.519(3) . ?
C4 S1 1.857(3) . ?
C5 C10 1.376(4) . ?
C5 C6 1.416(3) . ?
C6 N2 1.351(4) . ?
C6 C7 1.418(4) . ?
C7 C12 1.386(5) . ?
C7 N1 1.444(4) . ?
C10 C11 1.378(5) . ?
C10 H5 0.9300 . ?
C11 C12 1.356(5) . ?
C11 H11 0.9300 . ?
C12 H6 0.9300 . ?
C14 N2 1.435(4) . ?
C14 C15 1.509(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H8 0.9700 . ?
C15 H9 0.9700 . ?
C16 O3 1.226(3) . ?
C16 N3 1.358(3) . ?
C16 C17 1.484(3) . ?
C17 H12 0.9600 . ?
C17 H13 0.9600 . ?
C17 H14 0.9600 . ?
N1 O2 1.207(4) . ?
N1 O1 1.225(4) . ?
N2 H7 0.8600 . ?
N3 N4 1.397(3) . ?
N5 H4 0.8600 . ?
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
N3 C4 C5 C10 -26.4(3) . . . . ?
C15 C4 C5 C10 -154.3(2) . . . . ?
S1 C4 C5 C10 86.0(2) . . . . ?
N3 C4 C5 C6 156.93(19) . . . . ?
C15 C4 C5 C6 29.0(3) . . . . ?
S1 C4 C5 C6 -90.6(2) . . . . ?
C10 C5 C6 N2 -179.8(2) . . . . ?
C4 C5 C6 N2 -3.2(3) . . . . ?
C10 C5 C6 C7 0.2(4) . . . . ?
C4 C5 C6 C7 176.8(2) . . . . ?
N2 C6 C7 C12 -179.1(3) . . . . ?
C5 C6 C7 C12 0.9(5) . . . . ?
N2 C6 C7 N1 0.6(5) . . . . ?
C5 C6 C7 N1 -179.4(3) . . . . ?
C6 C5 C10 C11 -1.3(4) . . . . ?
C4 C5 C10 C11 -177.9(3) . . . . ?
C5 C10 C11 C12 1.3(5) . . . . ?
C10 C11 C12 C7 -0.1(6) . . . . ?
C6 C7 C12 C11 -1.0(6) . . . . ?
N1 C7 C12 C11 179.3(4) . . . . ?
N2 C14 C15 C4 54.1(3) . . . . ?
N3 C4 C15 C14 178.48(18) . . . . ?
C5 C4 C15 C14 -54.0(2) . . . . ?
S1 C4 C15 C14 65.8(2) . . . . ?
C12 C7 N1 O2 3.8(6) . . . . ?
C6 C7 N1 O2 -175.9(4) . . . . ?
C12 C7 N1 O1 -176.0(4) . . . . ?
C6 C7 N1 O1 4.3(6) . . . . ?
C5 C6 N2 C14 4.0(4) . . . . ?
C7 C6 N2 C14 -176.0(3) . . . . ?
C15 C14 N2 C6 -30.5(3) . . . . ?
O3 C16 N3 N4 -171.3(2) . . . . ?
C17 C16 N3 N4 9.5(3) . . . . ?
O3 C16 N3 C4 -5.3(3) . . . . ?
C17 C16 N3 C4 175.5(2) . . . . ?
C5 C4 N3 C16 -65.3(3) . . . . ?
C15 C4 N3 C16 61.9(3) . . . . ?
S1 C4 N3 C16 178.27(17) . . . . ?
C5 C4 N3 N4 100.9(2) . . . . ?
C15 C4 N3 N4 -131.9(2) . . . . ?
S1 C4 N3 N4 -15.5(2) . . . . ?
N5 C3 N4 N3 -177.86(19) . . . . ?
S1 C3 N4 N3 1.9(2) . . . . ?
C16 N3 N4 C3 176.79(19) . . . . ?
C4 N3 N4 C3 10.0(3) . . . . ?
O4 C2 N5 C3 1.2(5) . . . . ?
C1 C2 N5 C3 -179.5(3) . . . . ?
N4 C3 N5 C2 -172.1(2) . . . . ?
S1 C3 N5 C2 8.2(3) . . . . ?
N4 C3 S1 C4 -9.49(18) . . . . ?
N5 C3 S1 C4 170.22(19) . . . . ?
N3 C4 S1 C3 12.66(14) . . . . ?
C5 C4 S1 C3 -106.19(16) . . . . ?
C15 C4 S1 C3 132.24(15) . . . . ?
