#------------------------------------------------------------------------------
#$Date: 2020-10-20 07:26:09 +0300 (Tue, 20 Oct 2020) $
#$Revision: 258491 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/14/7241417.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_7241417
loop_
_publ_author_name
'Ruberte, Ana Carolina'
'Aydillo, Carlos'
'Sharma, Arun K.'
'Sanmartín, Carmen'
'Plano, Daniel'
_publ_section_title
;
 Vilsmeier reagent, NaHSe and diclofenac acid chloride: one-pot synthesis
 of a novel selenoindolinone with potent anticancer activity
;
_journal_issue                   63
_journal_name_full               'RSC Advances'
_journal_page_first              38404
_journal_page_last               38408
_journal_paper_doi               10.1039/D0RA07332F
_journal_volume                  10
_journal_year                    2020
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C16 H11 Cl2 N O Se'
_chemical_formula_sum            'C16 H11 Cl2 N O Se'
_chemical_formula_weight         383.12
_chemical_melting_point          446
_chemical_name_systematic
((E)-1-(2,6-dichlorophenyl)-3-((methylselanyl)methylene)indolin-2-one
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-01-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-10 deposited with the CCDC.	2020-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.072(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3923(9)
_cell_length_b                   12.7253(14)
_cell_length_c                   14.6560(15)
_cell_measurement_reflns_used    3722
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.238
_cell_measurement_theta_min      2.427
_cell_volume                     1565.2(3)
_computing_cell_refinement       'SAINT V6.36A (BRUKER, 2016)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT V6.36A (BRUKER, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 8.34
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13375
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.12
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.737
_exptl_absorpt_correction_T_max  0.9
_exptl_absorpt_correction_T_min  0.717833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS V2.05 (BRUKER, 2001) was used for absorption correction. R(int) was 0.0808 before and 0.0187 after correction. The Ratio of minimum to maximum transmission is 0.7178. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3859
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0587P)²+0.1981P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1049
_reflns_number_gt                2893
_reflns_number_total             3859
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0ra07332f2.cif
_cod_data_source_block           aks4s
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7241417
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C15(H15)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Se1 Se 0.10067(3) 0.50093(2) 0.662168(16) 0.05351(12) Uani 1 d . . .
Cl2 Cl 0.20025(9) 0.39022(5) 0.20020(5) 0.0635(2) Uani 1 d . . .
Cl3 Cl 0.44198(10) 0.08956(7) 0.41979(5) 0.0758(2) Uani 1 d . . .
O1 O 0.4211(2) 0.42263(14) 0.40139(12) 0.0589(5) Uani 1 d . . .
N1 N 0.2510(2) 0.28258(15) 0.38009(12) 0.0427(4) Uani 1 d . . .
C1 C 0.3345(2) 0.23897(18) 0.30454(14) 0.0406(5) Uani 1 d . . .
C2 C 0.4319(3) 0.1525(2) 0.31470(16) 0.0481(5) Uani 1 d . . .
C3 C 0.5210(3) 0.1137(2) 0.24283(18) 0.0580(7) Uani 1 d . . .
H3 H 0.5845 0.0545 0.2507 0.070 Uiso 1 calc . . R
C4 C 0.5147(3) 0.1634(2) 0.15967(17) 0.0569(7) Uani 1 d . . .
H4 H 0.5763 0.1386 0.1116 0.068 Uiso 1 calc . . R
C5 C 0.4182(3) 0.2493(2) 0.14698(16) 0.0520(6) Uani 1 d . . .
H5 H 0.4141 0.2827 0.0906 0.062 Uiso 1 calc . . R
C6 C 0.3273(3) 0.28561(18) 0.21908(15) 0.0427(5) Uani 1 d . . .
C7 C 0.1144(3) 0.24171(18) 0.42308(14) 0.0421(5) Uani 1 d . . .
C8 C 0.0283(3) 0.1534(2) 0.40109(19) 0.0604(7) Uani 1 d . . .
H8 H 0.0567 0.1108 0.3522 0.072 Uiso 1 calc . . R
C9 C -0.1031(4) 0.1304(2) 0.4552(2) 0.0706(8) Uani 1 d . . .
H9 H -0.1635 0.0710 0.4424 0.085 Uiso 1 calc . . R
C10 C -0.1455(3) 0.1938(2) 0.5270(2) 0.0669(8) Uani 1 d . . .
H10 H -0.2349 0.1769 0.5615 0.080 Uiso 1 calc . . R
C11 C -0.0580(3) 0.2818(2) 0.54884(17) 0.0542(6) Uani 1 d . . .
H11 H -0.0878 0.3240 0.5977 0.065 Uiso 1 calc . . R
C12 C 0.0749(3) 0.30694(18) 0.49728(14) 0.0402(5) Uani 1 d . . .
C13 C 0.1920(3) 0.39089(17) 0.50090(13) 0.0384(5) Uani 1 d . . .
C14 C 0.3039(3) 0.37290(18) 0.42393(14) 0.0426(5) Uani 1 d . . .
C15 C 0.2191(3) 0.46994(19) 0.55940(14) 0.0420(5) Uani 1 d . . .
H15 H 0.3057 0.5133 0.5471 0.050 Uiso 1 calc . . R
C16 C 0.2231(4) 0.6197(3) 0.7057(2) 0.0811(10) Uani 1 d . . .
H16A H 0.2238 0.6737 0.6601 0.122 Uiso 1 calc . . GR
H16B H 0.3304 0.5978 0.7181 0.122 Uiso 1 calc . . GR
H16C H 0.1757 0.6464 0.7606 0.122 Uiso 1 calc . . GR
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'
Cl Cl 0.1484 0.1585 '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'
Se Se -0.0929 2.2259 '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
C15 Se1 C16 98.62(12) . . ?
C7 N1 C1 127.27(18) . . ?
C14 N1 C1 121.66(18) . . ?
C14 N1 C7 111.01(17) . . ?
C2 C1 N1 121.3(2) . . ?
C2 C1 C6 117.6(2) . . ?
C6 C1 N1 121.0(2) . . ?
C1 C2 Cl3 119.44(18) . . ?
C1 C2 C3 121.6(2) . . ?
C3 C2 Cl3 119.0(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.4(2) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.2(2) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 Cl2 120.03(17) . . ?
C5 C6 Cl2 118.40(18) . . ?
C5 C6 C1 121.6(2) . . ?
N1 C7 C12 108.71(19) . . ?
C8 C7 N1 128.7(2) . . ?
C8 C7 C12 122.6(2) . . ?
C7 C8 H8 121.5 . . ?
C7 C8 C9 117.1(2) . . ?
C9 C8 H8 121.5 . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.4(3) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.1(2) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.4(2) . . ?
C12 C11 H11 120.3 . . ?
C7 C12 C13 107.54(18) . . ?
C11 C12 C7 118.4(2) . . ?
C11 C12 C13 134.0(2) . . ?
C12 C13 C14 106.69(18) . . ?
C15 C13 C12 133.6(2) . . ?
C15 C13 C14 119.6(2) . . ?
O1 C14 N1 124.3(2) . . ?
O1 C14 C13 129.7(2) . . ?
N1 C14 C13 106.05(18) . . ?
Se1 C15 H15 116.9 . . ?
C13 C15 Se1 126.18(19) . . ?
C13 C15 H15 116.9 . . ?
Se1 C16 H16A 109.5 . . ?
Se1 C16 H16B 109.5 . . ?
Se1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
Se1 C15 1.848(2) . ?
Se1 C16 1.935(3) . ?
Cl2 C6 1.728(2) . ?
Cl3 C2 1.738(3) . ?
O1 C14 1.216(3) . ?
N1 C1 1.424(3) . ?
N1 C7 1.408(3) . ?
N1 C14 1.389(3) . ?
C1 C2 1.379(3) . ?
C1 C6 1.387(3) . ?
C2 C3 1.383(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(3) . ?
C7 C8 1.375(3) . ?
C7 C12 1.408(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.389(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.373(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(3) . ?
C12 C13 1.453(3) . ?
C13 C14 1.487(3) . ?
C13 C15 1.341(3) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C15 H15 O1 0.93 2.55 3.363(3) 146.7 3_666
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
Cl3 C2 C3 C4 -179.5(2) . . . . ?
N1 C1 C2 Cl3 4.8(3) . . . . ?
N1 C1 C2 C3 -175.9(2) . . . . ?
N1 C1 C6 Cl2 -6.6(3) . . . . ?
N1 C1 C6 C5 174.5(2) . . . . ?
N1 C7 C8 C9 -179.9(3) . . . . ?
N1 C7 C12 C11 179.2(2) . . . . ?
N1 C7 C12 C13 -0.5(2) . . . . ?
C1 N1 C7 C8 -2.0(4) . . . . ?
C1 N1 C7 C12 177.5(2) . . . . ?
C1 N1 C14 O1 1.4(4) . . . . ?
C1 N1 C14 C13 -177.38(19) . . . . ?
C1 C2 C3 C4 1.2(4) . . . . ?
C2 C1 C6 Cl2 176.84(17) . . . . ?
C2 C1 C6 C5 -2.1(3) . . . . ?
C2 C3 C4 C5 -1.5(4) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 Cl2 -177.18(19) . . . . ?
C4 C5 C6 C1 1.8(4) . . . . ?
C6 C1 C2 Cl3 -178.70(17) . . . . ?
C6 C1 C2 C3 0.6(4) . . . . ?
C7 N1 C1 C2 -75.1(3) . . . . ?
C7 N1 C1 C6 108.5(3) . . . . ?
C7 N1 C14 O1 178.8(2) . . . . ?
C7 N1 C14 C13 0.0(2) . . . . ?
C7 C8 C9 C10 0.5(5) . . . . ?
C7 C12 C13 C14 0.5(2) . . . . ?
C7 C12 C13 C15 -175.0(2) . . . . ?
C8 C7 C12 C11 -1.3(4) . . . . ?
C8 C7 C12 C13 179.1(2) . . . . ?
C8 C9 C10 C11 -0.8(5) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
C10 C11 C12 C7 0.9(4) . . . . ?
C10 C11 C12 C13 -179.6(3) . . . . ?
C11 C12 C13 C14 -179.1(3) . . . . ?
C11 C12 C13 C15 5.4(4) . . . . ?
C12 C7 C8 C9 0.6(4) . . . . ?
C12 C13 C14 O1 -179.0(2) . . . . ?
C12 C13 C14 N1 -0.3(2) . . . . ?
C12 C13 C15 Se1 -1.7(4) . . . . ?
C14 N1 C1 C2 101.8(3) . . . . ?
C14 N1 C1 C6 -74.6(3) . . . . ?
C14 N1 C7 C8 -179.2(3) . . . . ?
C14 N1 C7 C12 0.3(3) . . . . ?
C14 C13 C15 Se1 -176.67(16) . . . . ?
C15 C13 C14 O1 -2.8(4) . . . . ?
C15 C13 C14 N1 176.0(2) . . . . ?
C16 Se1 C15 C13 178.5(2) . . . . ?
