Transition-Metal-Free Iodine Catalyzed Selenocayanation of Styrenyl Bromides and an Easy Access to Benzoselenophenes via Intermediacy of Styrenyl Selenocyanate.
Maity, Pintu; Paroi, Bidisha; Ranu, Brindaban C.; Organic letters 19 (2017) 5748–5751; doi:10.1021/acs.orglett.7b02571

data_1547801
_publ_section_title
;
 Transition-Metal-Free Iodine Catalyzed Selenocayanation of Styrenyl
 Bromides and an Easy Access to Benzoselenophenes via Intermediacy of
 Styrenyl Selenocyanate.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5748
_journal_page_last               5751
_journal_paper_doi               10.1021/acs.orglett.7b02571
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C11 H11 I O2 Se'
_chemical_formula_sum            'C11 H11 I O2 Se'
_chemical_formula_weight         381.06
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-08-11
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.931(5)
_cell_length_b                   10.477(4)
_cell_length_c                   18.151(7)
_cell_measurement_reflns_used    5278
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      23.42
_cell_measurement_theta_min      2.74
_cell_volume                     2459.1(16)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0761
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22906
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.046
_diffrn_reflns_theta_min         2.244
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.543
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.2433
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1820 before and 0.0834 after correction.
The Ratio of minimum to maximum transmission is 0.3264.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.059
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.116
_refine_diff_density_min         -1.039
_refine_diff_density_rms         0.142
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2427
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0452
_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/[\s^2^(Fo^2^)+(0.0882P)^2^+3.2950P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1517
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1795
_reflns_number_total             2427
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02571_si_001.cif
_cod_data_source_block           pintu
_cod_depositor_comments          'Adding full bibliography for 1547801.cif.'
_cod_database_code               1547801
_shelxl_version_number           2014/6
_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.a Secondary CH2 refined with riding coordinates:
 C00C(H00A,H00C)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00D(H00D)
2.c Idealised Me refined as rotating group:
 C00E(H00E,H00F,H00G), C00F(H00H,H00I,H00J)
;
_shelx_res_checksum              21860
_shelx_hkl_checksum              39098
_olex2_submission_special_instructions 'No special instructions were received'