Synthesis of difluoromethylselenoesters from aldehydes via a radical process.
Guo, Rui-Li; Zhu, Xue-Qing; Zhang, Xing-Long; Wang, Yong-Qiang; Chemical communications (Cambridge, England) 56 (2020) 8976–8979; doi:10.1039/d0cc02912b

data_7126769
_publ_section_title
;
 Synthesis of difluoromethylselenoesters from aldehydes via a radical
 process.
;
_journal_issue                   63
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8976
_journal_page_last               8979
_journal_paper_doi               10.1039/d0cc02912b
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C8 H5 Br F2 O Se'
_chemical_formula_sum            'C8 H5 Br F2 O Se'
_chemical_formula_weight         313.99
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-06
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-22 deposited with the CCDC.	2020-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                105.988(13)
_cell_angle_beta                 93.472(15)
_cell_angle_gamma                92.468(13)
_cell_formula_units_Z            2
_cell_length_a                   6.062(5)
_cell_length_b                   7.902(7)
_cell_length_c                   10.845(9)
_cell_measurement_reflns_used    899
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.76
_cell_measurement_theta_min      3.37
_cell_volume                     497.5(7)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2671
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         1.959
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.775
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.3545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1412 before and 0.0385 after correction. The Ratio of minimum to maximum transmission is 0.4756. The \l/2 correction factor is 0.0015.'
_exptl_crystal_density_diffrn    2.096
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_refine_diff_density_max         0.613
_refine_diff_density_min         -1.480
_refine_diff_density_rms         0.248
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1933
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0623
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1113P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1580
_refine_ls_wR_factor_ref         0.1755
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1358
_reflns_number_total             1933
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc02912b2.cif
_cod_data_source_block           aaa
_cod_depositor_comments
'Adding full bibliography for 7126769--7126770.cif.'
_cod_database_code               7126769
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 Se01-C004 \\sim Se01-C00C
 with sigma of 0.002
3. Rigid bond restraints
 C00C, C004
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C004) = Uanis(C00C)
5. Rigid body (RIGU) restrains
 C004, C00C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: H00B(0.5) H00C(0.5) F0AA(0.5) F2(0.5) F3(0.5) F4(0.5)
7.a Ternary CH refined with riding coordinates:
 C00C(H00B), C00C(H00C)
7.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C006(H006), C008(H008), C00A(H00A)
7.c Fitted hexagon refined as free rotating group:
 C005(C009,C006,C007,C008,C00A)
;
_shelx_res_checksum              47719
_shelx_hkl_checksum              45217
_olex2_submission_special_instructions 'No special instructions were received'