#------------------------------------------------------------------------------
#$Date: 2025-03-07 18:30:27 +0200 (Fri, 07 Mar 2025) $
#$Revision: 298328 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/67/7126770.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_7126770
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         'C18 H13 F2 O3 S Se'
_chemical_formula_sum            'C18 H13 F2 O3 S Se'
_chemical_formula_weight         426.32
_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
_audit_creation_date             2020-01-04
_audit_creation_method
;
Olex2 1.2
(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                97.388(6)
_cell_angle_beta                 97.162(7)
_cell_angle_gamma                106.374(6)
_cell_formula_units_Z            2
_cell_length_a                   8.167(3)
_cell_length_b                   9.361(4)
_cell_length_c                   12.114(5)
_cell_measurement_reflns_used    2418
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.82
_cell_measurement_theta_min      2.64
_cell_volume                     868.5(6)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.972
_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  0.0183
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4612
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.932
_diffrn_reflns_theta_min         2.302
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.316
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0610 before and 0.0298 after correction.
The Ratio of minimum to maximum transmission is 0.7283.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_description       bulk
_exptl_crystal_F_000             426
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.816
_refine_diff_density_min         -1.072
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0506
_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)+(0.0984P)²+0.5560P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1465
_refine_ls_wR_factor_ref         0.1552
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2726
_reflns_number_total             3286
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc02912b2.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7126769--7126770.cif.

2025-03-04
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         106.58
_cod_original_formula_moiety         '0.25(C18 H13 F2 O3 S Se)'
_cod_original_formula_units_Z            8
_cod_original_formula_sum        'C4.50 H3.25 F0.50 O0.75 S0.25 Se0.25'
_cod_database_code               7126770
_shelx_shelxl_version_number     2018/3
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00M(H00M)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00C), C00G(H00G), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00N(H00N), C00O(H00O)
2.c Idealised Me refined as rotating group:
 C00P(H00B,H00D,H00E)
;
_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 0.25197(8) 0.29040(5) 0.21974(4) 0.0705(2) Uani 1 1 d . . . . .
S002 S 0.21089(11) 0.05487(9) 0.63017(7) 0.0357(2) Uani 1 1 d . . . . .
O003 O 0.0733(3) 0.0325(3) 0.6944(3) 0.0493(7) Uani 1 1 d . . . . .
O004 O 0.2026(4) -0.0535(3) 0.5331(2) 0.0484(6) Uani 1 1 d . . . . .
C005 C 0.2243(4) 0.2163(3) 0.5798(3) 0.0260(6) Uani 1 1 d . . . . .
O006 O 0.3345(5) 0.5748(3) 0.3504(3) 0.0739(10) Uani 1 1 d . . . . .
F007 F 0.2031(5) 0.4870(4) 0.0801(3) 0.1037(12) Uani 1 1 d . . . . .
C008 C 0.2629(5) 0.3790(4) 0.4580(3) 0.0393(8) Uani 1 1 d . . . . .
C009 C 0.4070(4) 0.0904(4) 0.7227(3) 0.0349(7) Uani 1 1 d . . . . .
C00A C 0.5566(5) 0.0916(4) 0.6778(3) 0.0414(8) Uani 1 1 d . . . . .
H00A H 0.554144 0.077991 0.600155 0.050 Uiso 1 1 calc R . . . .
C00B C 0.2146(5) 0.3537(4) 0.6382(3) 0.0396(8) Uani 1 1 d . . . . .
C00C C 0.2548(5) 0.2352(4) 0.4727(3) 0.0385(8) Uani 1 1 d . . . . .
H00C H 0.267962 0.161233 0.418467 0.046 Uiso 1 1 calc R . . . .
C00D C 0.2381(5) 0.4582(4) 0.5629(3) 0.0406(8) Uani 1 1 d . . . . .
C00E C 0.2926(5) 0.4428(4) 0.3556(3) 0.0472(9) Uani 1 1 d . . . . .
F00F F 0.3755(7) 0.3684(5) 0.0341(3) 0.1281(16) Uani 1 1 d . . . . .
C00G C 0.4104(5) 0.1126(5) 0.8382(3) 0.0477(9) Uani 1 1 d . . . . .
H00G H 0.310118 0.112778 0.867040 0.057 Uiso 1 1 calc R . . . .
C00H C 0.7146(5) 0.1330(5) 0.8672(4) 0.0498(10) Uani 1 1 d . . . . .
C00I C 0.7097(5) 0.1136(5) 0.7520(4) 0.0483(9) Uani 1 1 d . . . . .
H00I H 0.810463 0.115350 0.723226 0.058 Uiso 1 1 calc R . . . .
C00J C 0.1851(6) 0.3905(5) 0.7466(4) 0.0512(10) Uani 1 1 d . . . . .
H00J H 0.169314 0.319966 0.794912 0.061 Uiso 1 1 calc R . . . .
C00K C 0.5634(6) 0.1344(5) 0.9105(4) 0.0543(10) Uani 1 1 d . . . . .
H00K H 0.566218 0.150129 0.988162 0.065 Uiso 1 1 calc R . . . .
C00L C 0.2308(7) 0.6034(5) 0.5984(4) 0.0599(11) Uani 1 1 d . . . . .
H00L H 0.246012 0.674239 0.550373 0.072 Uiso 1 1 calc R . . . .
C00M C 0.3317(7) 0.4383(6) 0.1242(4) 0.0684(13) Uani 1 1 d . . . . .
H00M H 0.429666 0.522996 0.165631 0.082 Uiso 1 1 calc R . . . .
C00N C 0.2005(8) 0.6401(5) 0.7062(5) 0.0740(15) Uani 1 1 d . . . . .
H00N H 0.193620 0.736399 0.730135 0.089 Uiso 1 1 calc R . . . .
C00O C 0.1797(8) 0.5359(6) 0.7808(4) 0.0691(13) Uani 1 1 d . . . . .
H00O H 0.162265 0.564642 0.853738 0.083 Uiso 1 1 calc R . . . .
C00P C 0.8805(7) 0.1539(7) 0.9462(5) 0.0791(16) Uani 1 1 d . . . . .
H00B H 0.931259 0.077160 0.921351 0.119 Uiso 1 1 calc GR . . . .
H00D H 0.856337 0.146133 1.021090 0.119 Uiso 1 1 calc GR . . . .
H00E H 0.959628 0.251737 0.946401 0.119 Uiso 1 1 calc GR . . . .
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'
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'
S S 0.1246 0.1234 '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
C00M Se01 C00E 94.08(19) . . ?
O003 S002 O004 120.58(18) . . ?
O003 S002 C005 106.77(16) . . ?
O003 S002 C009 108.55(17) . . ?
O004 S002 C005 104.53(16) . . ?
O004 S002 C009 109.94(17) . . ?
C005 S002 C009 105.36(15) . . ?
C00B C005 S002 127.4(3) . . ?
C00C C005 S002 123.5(2) . . ?
C00C C005 C00B 109.0(3) . . ?
C00C C008 C00D 107.7(3) . . ?
C00C C008 C00E 126.3(3) . . ?
C00D C008 C00E 126.0(3) . . ?
C00A C009 S002 119.0(3) . . ?
C00G C009 S002 119.9(3) . . ?
C00G C009 C00A 121.0(3) . . ?
C00I C00A C009 118.5(3) . . ?
C00D C00B C005 107.0(3) . . ?
C00J C00B C005 130.6(3) . . ?
C00J C00B C00D 122.3(3) . . ?
C008 C00C C005 109.7(3) . . ?
C00B C00D C008 106.5(3) . . ?
C00L C00D C008 134.4(4) . . ?
C00L C00D C00B 119.1(4) . . ?
O006 C00E Se01 120.8(3) . . ?
O006 C00E C008 125.3(4) . . ?
C008 C00E Se01 113.9(3) . . ?
C00K C00G C009 119.7(4) . . ?
C00I C00H C00K 119.3(4) . . ?
C00I C00H C00P 120.6(4) . . ?
C00K C00H C00P 120.1(4) . . ?
C00H C00I C00A 121.3(4) . . ?
C00B C00J C00O 117.8(4) . . ?
C00G C00K C00H 120.3(4) . . ?
C00N C00L C00D 118.7(4) . . ?
F007 C00M Se01 111.4(4) . . ?
F007 C00M F00F 103.9(4) . . ?
F00F C00M Se01 108.1(4) . . ?
C00L C00N C00O 121.7(4) . . ?
C00J C00O C00N 120.4(4) . . ?
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 C00E 1.961(4) . ?
Se01 C00M 1.942(5) . ?
S002 O003 1.428(3) . ?
S002 O004 1.432(3) . ?
S002 C005 1.682(3) . ?
S002 C009 1.758(4) . ?
C005 C00B 1.413(5) . ?
C005 C00C 1.376(5) . ?
O006 C00E 1.198(5) . ?
F007 C00M 1.337(7) . ?
C008 C00C 1.364(5) . ?
C008 C00D 1.453(5) . ?
C008 C00E 1.462(5) . ?
C009 C00A 1.396(5) . ?
C009 C00G 1.383(5) . ?
C00A C00I 1.392(5) . ?
C00B C00D 1.412(5) . ?
C00B C00J 1.382(6) . ?
C00D C00L 1.392(6) . ?
F00F C00M 1.340(6) . ?
C00G C00K 1.381(6) . ?
C00H C00I 1.378(6) . ?
C00H C00K 1.403(6) . ?
C00H C00P 1.506(6) . ?
C00J C00O 1.386(6) . ?
C00L C00N 1.377(7) . ?
C00N C00O 1.403(7) . ?
