#------------------------------------------------------------------------------
#$Date: 2020-09-06 10:11:55 +0200 (dom 06 de sep de 2020) $
#$Revision: 255949 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/67/7126769.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_7126769
loop_
_publ_author_name
'Guo, Rui-Li'
'Zhu, Xue-Qing'
'Zhang, Xing-Long'
'Wang, Yong-Qiang'
_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       'φ and ω 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 λ/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/[σ²(Fo²)+(0.1113P)²] where P=(Fo²+2Fc²)/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 > 2σ(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
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se01 Se 0.43714(13) 0.76014(12) 0.87842(7) 0.0688(4) Uani 1 1 d D . . . .
Br02 Br 0.78513(14) 0.80380(10) 0.25924(7) 0.0685(3) Uani 1 1 d . . . . .
O003 O 0.0827(8) 0.6465(8) 0.6959(5) 0.0731(16) Uani 1 1 d . . . . .
C004 C 0.2734(11) 0.7020(9) 0.7090(5) 0.0560(12) Uani 1 1 d D U . . .
C005 C 0.4019(6) 0.7304(5) 0.6032(3) 0.0407(13) Uani 1 1 d . . . . .
C009 C 0.6133(6) 0.8131(5) 0.6250(3) 0.0484(15) Uani 1 1 d G . . . .
H009 H 0.6791 0.8536 0.7084 0.058 Uiso 1 1 calc R . . . .
C006 C 0.7264(5) 0.8353(5) 0.5223(4) 0.0515(16) Uani 1 1 d G . . . .
H006 H 0.8678 0.8907 0.5369 0.062 Uiso 1 1 calc R . . . .
C007 C 0.6280(7) 0.7748(5) 0.3977(3) 0.0483(16) Uani 1 1 d G . . . .
C008 C 0.4166(7) 0.6920(5) 0.3758(3) 0.0512(16) Uani 1 1 d G . . . .
H008 H 0.3508 0.6515 0.2924 0.061 Uiso 1 1 calc R . . . .
C00A C 0.3035(5) 0.6698(5) 0.4786(4) 0.0462(15) Uani 1 1 d G . . . .
H00A H 0.1621 0.6145 0.4639 0.055 Uiso 1 1 calc R . . . .
C00C C 0.1824(11) 0.7035(10) 0.9661(6) 0.0560(12) Uani 1 1 d D U . . .
H00B H 0.0914 0.6100 0.9028 0.067 Uiso 0.5 1 calc R . P A 2
H00C H 0.0446 0.6721 0.9106 0.067 Uiso 0.5 1 calc R . P B 1
F0AA F 0.061(3) 0.829(3) 1.003(2) 0.142(8) Uani 0.5 1 d . . P C 2
F2 F 0.170(3) 0.849(3) 1.0733(14) 0.114(7) Uani 0.5 1 d . . P C 1
F3 F 0.245(4) 0.638(4) 1.058(2) 0.129(11) Uani 0.5 1 d . . P C 2
F4 F 0.236(7) 0.581(4) 1.028(3) 0.125(10) Uani 0.5 1 d . . P C 1
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
C00C Se01 C004 94.1(3) . . ?
O003 C004 Se01 120.3(5) . . ?
O003 C004 C005 124.4(5) . . ?
C005 C004 Se01 115.2(4) . . ?
C009 C005 C004 122.4(3) . . ?
C009 C005 C00A 120.0 . . ?
C00A C005 C004 117.6(3) . . ?
C005 C009 H009 120.0 . . ?
C005 C009 C006 120.0 . . ?
C006 C009 H009 120.0 . . ?
C009 C006 H006 120.0 . . ?
C009 C006 C007 120.0 . . ?
C007 C006 H006 120.0 . . ?
C006 C007 Br02 119.4(2) . . ?
C006 C007 C008 120.0 . . ?
C008 C007 Br02 120.6(2) . . ?
C007 C008 H008 120.0 . . ?
C007 C008 C00A 120.0 . . ?
C00A C008 H008 120.0 . . ?
C005 C00A H00A 120.0 . . ?
C008 C00A C005 120.0 . . ?
C008 C00A H00A 120.0 . . ?
Se01 C00C H00B 106.5 . . ?
Se01 C00C H00C 113.9 . . ?
F0AA C00C Se01 113.7(11) . . ?
F0AA C00C H00B 106.5 . . ?
F0AA C00C F3 112.4(18) . . ?
F2 C00C Se01 105.5(8) . . ?
F2 C00C H00C 113.9 . . ?
F3 C00C Se01 110.7(12) . . ?
F3 C00C H00B 106.5 . . ?
F4 C00C Se01 109.5(17) . . ?
F4 C00C H00C 113.9 . . ?
F4 C00C F2 98.9(15) . . ?
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
Se01 C004 1.961(5) . ?
Se01 C00C 1.960(5) . ?
Br02 C007 1.886(3) . ?
O003 C004 1.205(8) . ?
C004 C005 1.487(7) . ?
C005 C009 1.3900 . ?
C005 C00A 1.3900 . ?
C009 H009 0.9300 . ?
C009 C006 1.3900 . ?
C006 H006 0.9300 . ?
C006 C007 1.3900 . ?
C007 C008 1.3900 . ?
C008 H008 0.9300 . ?
C008 C00A 1.3900 . ?
C00A H00A 0.9300 . ?
C00C H00B 0.9800 . ?
C00C H00C 0.9800 . ?
C00C F0AA 1.25(2) . ?
C00C F2 1.403(18) . ?
C00C F3 1.29(2) . ?
C00C F4 1.36(3) . ?
