A novel methodology for the synthesis of condensed selenium heterocycles based on the annulation and annulation − methoxylation reactions of selenium dihalides
Musalov, Maxim V.; Yakimov, Vladimir A.; Potapov, Vladimir A.; Amosova, Svetlana V.; Borodina, Tatiana; Zinchenko, Sergey V.; New Journal of Chemistry 43 (2019) 18476–18483; doi:10.1039/C9NJ04707G

data_7059016
_publ_section_title
;
 A novel methodology for the synthesis of condensed selenium heterocycles
 based on the annulation and annulation &#x2212; methoxylation reactions
 of selenium dihalides
;
_journal_issue                   47
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              18476
_journal_page_last               18483
_journal_paper_doi               10.1039/C9NJ04707G
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C11.57 H15.55 O2.59 Se, 0.41(C), 0.41(O)'
_chemical_formula_sum            'C11.98 H15.55 O3 Se'
_chemical_formula_weight         286.54
_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             2019-01-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-25 deposited with the CCDC.	2019-11-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.018(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3669(6)
_cell_length_b                   6.1164(3)
_cell_length_c                   15.6194(7)
_cell_measurement_reflns_used    9263
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      2.61
_cell_measurement_theta_min      30.06
_cell_volume                     1181.28(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            40146
_diffrn_reflns_theta_full        30.08
_diffrn_reflns_theta_max         30.08
_diffrn_reflns_theta_min         2.61
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.168
_exptl_absorpt_correction_T_max  0.0320
_exptl_absorpt_correction_T_min  0.0051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1342 before and 0.0783 after correction. The Ratio of minimum to maximum transmission is 0.1594. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.673
_exptl_crystal_size_mid          0.673
_exptl_crystal_size_min          0.472
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         3473
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0297
_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/[\s^2^(Fo^2^)+(0.0286P)^2^+1.5397P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0723
_refine_ls_wR_factor_ref         0.0734
_reflns_number_gt                3278
_reflns_number_total             3473
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9nj04707g2.cif
_cod_data_source_block           compound_8
_cod_database_code               7059016
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Se1-C2 \\sim Se1-C2A
 with sigma of 0.02
 O3-C10 \\sim O3A-C10
 with sigma of 0.02
 O3-C13 \\sim O3A-C13
 with sigma of 0.02
 C3-C2 \\sim C3-C2A
 with sigma of 0.02
 C10-C2 \\sim C10-C2A
 with sigma of 0.02
3. Others
 Sof(C3)=Sof(H3a)=Sof(H3b)=Sof(C10)=Sof(H10a)=Sof(H10b)=Sof(C13)=Sof(H13a)=
 Sof(H13b)=Sof(H13c)=FVAR(1)
 Sof(C2A)=Sof(O3A)=1-FVAR(2)
 Sof(O3)=Sof(C2)=Sof(H2)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C2(H2)
4.b Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b), C10(H10a,H10b)
4.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4)
4.d Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C11(H11a,H11b,H11c), C13(H13a,H13b,H13c)
;
_olex2_submission_special_instructions 'No special instructions were received'