#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:02:58 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/52/04/1520449.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_1520449
loop_
_publ_author_name
'Siva Reddy, Alla'
'Kumara Swamy, K. C.'
_publ_section_title
;
 Use of Elemental Sulfur or Selenium in a Novel One-Pot Copper-Catalyzed
 Tandem Cyclization of Functionalized Ynamides Leading to Benzosultams.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2996
_journal_page_last               2999
_journal_paper_doi               10.1021/acs.orglett.5b01287
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C16 H15 N O2 S Se'
_chemical_formula_weight         364.31
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.38023(19)
_cell_length_b                   12.8750(3)
_cell_length_c                   31.8273(8)
_cell_measurement_reflns_used    4366
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      71.8310
_cell_measurement_theta_min      3.4430
_cell_volume                     3024.24(13)
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_collection       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 16.3291
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            7482
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_reflns_theta_max         71.83
_diffrn_reflns_theta_min         5.56
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_number         'not applicable'
_exptl_absorpt_coefficient_mu    4.682
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, Oxford Diffraction Ltd.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2900
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0740P)²+1.1223P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1125
_reflns_number_gt                2711
_reflns_number_total             2900
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b01287_si_002.cif
_cod_data_source_block           compound-5a
_cod_depositor_comments
'Adding full bibliography for 1520446--1520450.cif.'
_cod_original_cell_volume        3024.25(14)
_cod_database_code               1520449
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Se1 Se 0.16162(4) 0.26384(2) 0.411564(8) 0.04648(15) Uani 1 1 d .
S1 S 0.23949(8) 0.45073(5) 0.335439(17) 0.03737(18) Uani 1 1 d .
O1 O 0.3313(3) 0.47505(18) 0.29727(6) 0.0541(5) Uani 1 1 d .
O2 O 0.1400(3) 0.52932(16) 0.35702(7) 0.0522(5) Uani 1 1 d .
C7 C 0.3185(3) 0.3822(2) 0.40918(7) 0.0351(5) Uani 1 1 d .
C6 C 0.0654(3) 0.26722(18) 0.35589(7) 0.0363(5) Uani 1 1 d .
C8 C 0.3569(3) 0.4415(2) 0.44215(8) 0.0380(5) Uani 1 1 d .
H8 H 0.4334 0.4977 0.4375 0.046 Uiso 1 1 calc R
N1 N 0.3926(3) 0.40647(18) 0.36877(6) 0.0388(4) Uani 1 1 d .
C2 C 0.0129(3) 0.3378(2) 0.28664(8) 0.0460(6) Uani 1 1 d .
H2 H 0.0339 0.3889 0.2666 0.055 Uiso 1 1 calc R
C5 C -0.0471(3) 0.1845(2) 0.34569(8) 0.0422(5) Uani 1 1 d .
H5 H -0.0660 0.1321 0.3653 0.051 Uiso 1 1 calc R
C1 C 0.0961(3) 0.34436(19) 0.32569(7) 0.0359(5) Uani 1 1 d .
C9 C 0.2903(3) 0.4271(2) 0.48533(7) 0.0359(5) Uani 1 1 d .
C4 C -0.1320(3) 0.1783(2) 0.30690(9) 0.0456(6) Uani 1 1 d .
C3 C -0.1003(4) 0.2562(2) 0.27762(9) 0.0492(7) Uani 1 1 d .
H3 H -0.1565 0.2530 0.2515 0.059 Uiso 1 1 calc R
C10 C 0.2797(4) 0.3299(2) 0.50409(8) 0.0474(6) Uani 1 1 d .
H10 H 0.3228 0.2718 0.4899 0.057 Uiso 1 1 calc R
C13 C 0.1603(4) 0.5006(3) 0.54814(10) 0.0577(8) Uani 1 1 d .
H13 H 0.1218 0.5585 0.5631 0.069 Uiso 1 1 calc R
C12 C 0.1441(4) 0.4037(3) 0.56557(9) 0.0587(8) Uani 1 1 d .
H12 H 0.0919 0.3956 0.5920 0.070 Uiso 1 1 calc R
C14 C 0.2337(4) 0.5130(2) 0.50822(9) 0.0478(6) Uani 1 1 d .
H14 H 0.2450 0.5791 0.4968 0.057 Uiso 1 1 calc R
C15 C -0.2560(4) 0.0884(3) 0.29711(12) 0.0648(9) Uani 1 1 d .
H15A H -0.3782 0.1067 0.3043 0.097 Uiso 1 1 calc R
H15B H -0.2194 0.0288 0.3131 0.097 Uiso 1 1 calc R
H15C H -0.2492 0.0726 0.2677 0.097 Uiso 1 1 calc R
C11 C 0.2055(5) 0.3186(3) 0.54384(9) 0.0597(8) Uani 1 1 d .
H11 H 0.1972 0.2529 0.5559 0.072 Uiso 1 1 calc R
C16 C 0.5251(4) 0.3318(3) 0.35179(10) 0.0609(8) Uani 1 1 d .
H16A H 0.6290 0.3291 0.3699 0.091 Uiso 1 1 calc R
H16B H 0.5620 0.3534 0.3242 0.091 Uiso 1 1 calc R
H16C H 0.4707 0.2642 0.3502 0.091 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 '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
C6 Se1 C7 99.78(10)
O1 S1 O2 119.94(14)
O1 S1 N1 107.32(11)
O2 S1 N1 106.72(12)
O1 S1 C1 107.87(12)
O2 S1 C1 109.13(12)
N1 S1 C1 104.86(11)
C8 C7 N1 120.1(2)
C8 C7 Se1 123.71(18)
N1 C7 Se1 116.13(18)
C5 C6 C1 118.7(2)
C5 C6 Se1 114.94(19)
C1 C6 Se1 126.35(18)
C7 C8 C9 126.4(2)
C7 C8 H8 116.8
C9 C8 H8 116.8
C7 N1 C16 116.1(2)
C7 N1 S1 113.00(16)
C16 N1 S1 116.34(18)
C3 C2 C1 120.2(3)
C3 C2 H2 119.9
C1 C2 H2 119.9
C4 C5 C6 121.5(3)
C4 C5 H5 119.3
C6 C5 H5 119.3
C2 C1 C6 120.0(2)
C2 C1 S1 118.1(2)
C6 C1 S1 121.93(18)
C14 C9 C10 118.4(2)
C14 C9 C8 119.3(2)
C10 C9 C8 122.3(2)
C5 C4 C3 118.6(3)
C5 C4 C15 120.2(3)
C3 C4 C15 121.2(3)
C2 C3 C4 121.0(3)
C2 C3 H3 119.5
C4 C3 H3 119.5
C11 C10 C9 120.6(3)
C11 C10 H10 119.7
C9 C10 H10 119.7
C12 C13 C14 120.6(3)
C12 C13 H13 119.7
C14 C13 H13 119.7
C13 C12 C11 119.6(3)
C13 C12 H12 120.2
C11 C12 H12 120.2
C9 C14 C13 120.3(3)
C9 C14 H14 119.8
C13 C14 H14 119.8
C4 C15 H15A 109.5
C4 C15 H15B 109.5
H15A C15 H15B 109.5
C4 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C12 C11 C10 120.4(3)
C12 C11 H11 119.8
C10 C11 H11 119.8
N1 C16 H16A 109.5
N1 C16 H16B 109.5
H16A C16 H16B 109.5
N1 C16 H16C 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
Se1 C6 1.910(2)
Se1 C7 1.915(3)
S1 O1 1.4259(19)
S1 O2 1.427(2)
S1 N1 1.651(2)
S1 C1 1.758(3)
C7 C8 1.328(4)
C7 N1 1.432(3)
C6 C5 1.389(4)
C6 C1 1.400(3)
C8 C9 1.471(3)
C8 H8 0.9300
N1 C16 1.474(3)
C2 C3 1.373(4)
C2 C1 1.389(3)
C2 H2 0.9300
C5 C4 1.387(4)
C5 H5 0.9300
C9 C14 1.389(4)
C9 C10 1.389(4)
C4 C3 1.389(4)
C4 C15 1.507(4)
C3 H3 0.9300
C10 C11 1.386(4)
C10 H10 0.9300
C13 C12 1.370(5)
C13 C14 1.391(5)
C13 H13 0.9300
C12 C11 1.373(5)
C12 H12 0.9300
C14 H14 0.9300
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C11 H11 0.9300
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139045564
