#------------------------------------------------------------------------------
#$Date: 2020-07-25 08:04:04 +0300 (Sat, 25 Jul 2020) $
#$Revision: 254579 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/22/2022210.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022210
loop_
_publ_author_name
'Kolade, Sherif O.'
'Izunobi, Josephat U.'
'Hosten, Eric C.'
'Olasupo, Idris A.'
'Ogunlaja, Adeniyi S.'
'Familoni, Oluwole B.'
_publ_section_title
;
 Synthesis, crystal structure and docking studies of tetracyclic
 10-iodo-1,2-dihydroisoquinolino[2,1-b][1,2,4]benzothiadiazine
 12,12-dioxide and its precursors
;
_journal_coeditor_code           EP3007
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229620009626
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C15 H11 I N2 O2 S'
_chemical_formula_moiety         'C15 H11 I N2 O2 S'
_chemical_formula_sum            'C15 H11 I N2 O2 S'
_chemical_formula_weight         410.22
_chemical_name_systematic
;
10-Iodo-1,2-dihydroisoquinolino[2,1-b][1,2,4]benzothiadiazine
12,12-dioxide
;
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 93.624(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9586(6)
_cell_length_b                   10.2679(6)
_cell_length_c                   12.9392(8)
_cell_measurement_reflns_used    7151
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.04
_cell_measurement_theta_min      2.53
_cell_volume                     1453.03(15)
_computing_cell_refinement
;
APEX2 (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Johnson, 1965, 1976; Farrugia,
2012)
;
_computing_publication_material
;
PLATON (Spek, 2020) and Mercury (Macrae et al.,  2020)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b) and ShelXle (Hübschle et al.,
2011)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.455
_diffrn_reflns_theta_min         1.862
_exptl_absorpt_coefficient_mu    2.352
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7631
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.875
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.488
_exptl_crystal_size_mid          0.362
_exptl_crystal_size_min          0.060
_refine_diff_density_max         1.855
_refine_diff_density_min         -1.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0444
_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)+(0.0905P)²+2.0774P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1390
_refine_ls_wR_factor_ref         0.1498
_reflns_number_gt                2871
_reflns_number_total             3628
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ep3007sup1.cif
_cod_data_source_block           8
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2022210
_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   0.393
_shelx_estimated_absorpt_t_max   0.872
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 1.01660(3) 0.46280(3) 0.16942(3) 0.06583(18) Uani d 1 . .
S S1 0.70749(8) 0.75401(9) 0.41931(8) 0.0379(2) Uani d 1 . .
O O1 0.8074(3) 0.7664(4) 0.4940(3) 0.0613(9) Uani d 1 . .
O O2 0.6731(4) 0.8659(3) 0.3584(3) 0.0624(9) Uani d 1 . .
N N1 0.5073(3) 0.5693(3) 0.3420(2) 0.0324(6) Uani d 1 . .
N N2 0.5882(3) 0.7021(3) 0.4798(2) 0.0335(6) Uani d 1 . .
C C1 0.4936(3) 0.6383(3) 0.4240(2) 0.0290(6) Uani d 1 . .
C C2 0.5695(4) 0.7534(4) 0.5854(3) 0.0407(8) Uani d 1 . .
H H2A 0.636382 0.810999 0.607258 0.049 Uiso calc 1 . .
H H2B 0.568488 0.681763 0.634225 0.049 Uiso calc 1 . .
C C3 0.4510(4) 0.8261(4) 0.5847(3) 0.0448(9) Uani d 1 . .
H H3A 0.456633 0.905008 0.543989 0.054 Uiso calc 1 . .
H H3B 0.434757 0.850892 0.654831 0.054 Uiso calc 1 . .
C C11 0.6227(3) 0.5507(3) 0.3062(2) 0.0293(6) Uani d 1 . .
C C12 0.7255(3) 0.6235(3) 0.3372(2) 0.0302(7) Uani d 1 . .
C C13 0.8396(3) 0.6004(3) 0.2992(3) 0.0354(7) Uani d 1 . .
H H13 0.907117 0.650186 0.321468 0.042 Uiso calc 1 . .
C C14 0.8503(4) 0.5020(4) 0.2277(3) 0.0361(7) Uani d 1 . .
C C15 0.7487(4) 0.4288(4) 0.1941(3) 0.0400(8) Uani d 1 . .
H H15 0.756778 0.362938 0.145654 0.048 Uiso calc 1 . .
C C16 0.6363(4) 0.4529(4) 0.2319(3) 0.0372(8) Uani d 1 . .
H H16 0.568830 0.403990 0.208068 0.045 Uiso calc 1 . .
C C21 0.3706(3) 0.6515(3) 0.4628(3) 0.0310(7) Uani d 1 . .
C C22 0.3482(3) 0.7433(4) 0.5396(3) 0.0369(8) Uani d 1 . .
C C23 0.2295(4) 0.7573(5) 0.5695(3) 0.0489(10) Uani d 1 . .
H H23 0.213387 0.818906 0.619466 0.059 Uiso calc 1 . .
C C24 0.1357(4) 0.6830(5) 0.5274(4) 0.0562(12) Uani d 1 . .
H H24 0.056878 0.694086 0.548763 0.067 Uiso calc 1 . .
C C25 0.1585(4) 0.5911(5) 0.4528(4) 0.0534(11) Uani d 1 . .
H H25 0.094778 0.539973 0.424588 0.064 Uiso calc 1 . .
C C26 0.2745(4) 0.5745(4) 0.4199(3) 0.0413(8) Uani d 1 . .
H H26 0.289054 0.512725 0.369543 0.050 Uiso calc 1 . .
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'
I I -0.4742 1.8119 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 O2 . . 117.9(2) ?
O1 S1 N2 . . 107.81(19) ?
O2 S1 N2 . . 109.33(19) ?
O1 S1 C12 . . 112.00(19) ?
O2 S1 C12 . . 108.68(19) ?
N2 S1 C12 . . 99.50(16) ?
C1 N1 C11 . . 120.3(3) ?
C1 N2 C2 . . 120.1(3) ?
C1 N2 S1 . . 119.5(2) ?
C2 N2 S1 . . 118.6(2) ?
N1 C1 N2 . . 124.3(3) ?
N1 C1 C21 . . 119.0(3) ?
N2 C1 C21 . . 116.7(3) ?
N2 C2 C3 . . 109.9(3) ?
N2 C2 H2A . . 109.7 ?
C3 C2 H2A . . 109.7 ?
N2 C2 H2B . . 109.7 ?
C3 C2 H2B . . 109.7 ?
H2A C2 H2B . . 108.2 ?
C2 C3 C22 . . 110.5(3) ?
C2 C3 H3A . . 109.6 ?
C22 C3 H3A . . 109.6 ?
C2 C3 H3B . . 109.6 ?
C22 C3 H3B . . 109.6 ?
H3A C3 H3B . . 108.1 ?
N1 C11 C12 . . 124.6(3) ?
N1 C11 C16 . . 117.7(3) ?
C12 C11 C16 . . 117.6(3) ?
C11 C12 C13 . . 122.4(3) ?
C11 C12 S1 . . 118.2(3) ?
C13 C12 S1 . . 119.3(3) ?
C14 C13 C12 . . 118.6(3) ?
C14 C13 H13 . . 120.7 ?
C12 C13 H13 . . 120.7 ?
C13 C14 C15 . . 120.3(3) ?
C13 C14 I1 . . 120.3(3) ?
C15 C14 I1 . . 119.4(3) ?
C16 C15 C14 . . 120.6(3) ?
C16 C15 H15 . . 119.7 ?
C14 C15 H15 . . 119.7 ?
C15 C16 C11 . . 120.5(3) ?
C15 C16 H16 . . 119.8 ?
C11 C16 H16 . . 119.8 ?
C26 C21 C22 . . 119.9(3) ?
C26 C21 C1 . . 119.6(3) ?
C22 C21 C1 . . 120.5(3) ?
C23 C22 C21 . . 118.4(4) ?
C23 C22 C3 . . 121.8(4) ?
C21 C22 C3 . . 119.7(3) ?
C24 C23 C22 . . 121.8(4) ?
C24 C23 H23 . . 119.1 ?
C22 C23 H23 . . 119.1 ?
C23 C24 C25 . . 119.6(4) ?
C23 C24 H24 . . 120.2 ?
C25 C24 H24 . . 120.2 ?
C26 C25 C24 . . 120.8(4) ?
C26 C25 H25 . . 119.6 ?
C24 C25 H25 . . 119.6 ?
C25 C26 C21 . . 119.5(4) ?
C25 C26 H26 . . 120.2 ?
C21 C26 H26 . . 120.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 C14 . 2.055(4) ?
S1 O1 . 1.419(3) ?
S1 O2 . 1.430(4) ?
S1 N2 . 1.653(3) ?
S1 C12 . 1.729(3) ?
N1 C1 . 1.293(4) ?
N1 C11 . 1.388(4) ?
N2 C1 . 1.389(4) ?
N2 C2 . 1.491(4) ?
C1 C21 . 1.474(5) ?
C2 C3 . 1.498(6) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C22 . 1.500(6) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C11 C12 . 1.389(5) ?
C11 C16 . 1.405(5) ?
C12 C13 . 1.393(5) ?
C13 C14 . 1.379(5) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.391(6) ?
C15 C16 . 1.376(6) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C21 C26 . 1.403(5) ?
C21 C22 . 1.403(5) ?
C22 C23 . 1.388(6) ?
C23 C24 . 1.365(7) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.384(8) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.376(6) ?
C25 H25 . 0.9300 ?
C26 H26 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C2 H2A O1 . 0.97 2.49 2.934(5) 107 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 S1 N2 C1 . . . . -157.1(3) ?
O2 S1 N2 C1 . . . . 73.5(3) ?
C12 S1 N2 C1 . . . . -40.2(3) ?
O1 S1 N2 C2 . . . . 38.2(3) ?
O2 S1 N2 C2 . . . . -91.1(3) ?
C12 S1 N2 C2 . . . . 155.1(3) ?
C11 N1 C1 N2 . . . . 2.5(5) ?
C11 N1 C1 C21 . . . . -177.3(3) ?
C2 N2 C1 N1 . . . . -166.0(4) ?
S1 N2 C1 N1 . . . . 29.6(5) ?
C2 N2 C1 C21 . . . . 13.8(5) ?
S1 N2 C1 C21 . . . . -150.6(3) ?
C1 N2 C2 C3 . . . . -46.8(5) ?
S1 N2 C2 C3 . . . . 117.8(3) ?
N2 C2 C3 C22 . . . . 52.9(4) ?
C1 N1 C11 C12 . . . . -15.1(5) ?
C1 N1 C11 C16 . . . . 166.1(3) ?
N1 C11 C12 C13 . . . . 179.7(3) ?
C16 C11 C12 C13 . . . . -1.5(5) ?
N1 C11 C12 S1 . . . . -4.7(5) ?
C16 C11 C12 S1 . . . . 174.1(3) ?
O1 S1 C12 C11 . . . . 142.0(3) ?
O2 S1 C12 C11 . . . . -85.9(3) ?
N2 S1 C12 C11 . . . . 28.3(3) ?
O1 S1 C12 C13 . . . . -42.3(4) ?
O2 S1 C12 C13 . . . . 89.8(3) ?
N2 S1 C12 C13 . . . . -156.0(3) ?
C11 C12 C13 C14 . . . . 0.4(5) ?
S1 C12 C13 C14 . . . . -175.2(3) ?
C12 C13 C14 C15 . . . . 0.5(6) ?
C12 C13 C14 I1 . . . . -179.7(3) ?
C13 C14 C15 C16 . . . . -0.3(6) ?
I1 C14 C15 C16 . . . . 179.9(3) ?
C14 C15 C16 C11 . . . . -0.9(6) ?
N1 C11 C16 C15 . . . . -179.4(3) ?
C12 C11 C16 C15 . . . . 1.8(5) ?
N1 C1 C21 C26 . . . . 9.3(5) ?
N2 C1 C21 C26 . . . . -170.5(3) ?
N1 C1 C21 C22 . . . . -168.6(3) ?
N2 C1 C21 C22 . . . . 11.6(5) ?
C26 C21 C22 C23 . . . . -1.5(5) ?
C1 C21 C22 C23 . . . . 176.4(3) ?
C26 C21 C22 C3 . . . . -179.5(3) ?
C1 C21 C22 C3 . . . . -1.7(5) ?
C2 C3 C22 C23 . . . . 150.6(4) ?
C2 C3 C22 C21 . . . . -31.4(5) ?
C21 C22 C23 C24 . . . . 1.1(6) ?
C3 C22 C23 C24 . . . . 179.1(4) ?
C22 C23 C24 C25 . . . . -0.1(7) ?
C23 C24 C25 C26 . . . . -0.6(7) ?
C24 C25 C26 C21 . . . . 0.2(7) ?
C22 C21 C26 C25 . . . . 0.8(6) ?
C1 C21 C26 C25 . . . . -177.0(4) ?

_cod_database_fobs_code 2022210
