Accessing structurally diverse aryl difluoromethyl ethers with bromo(difluoro)acetic acid.
Kumawat, Sandeep; Natte, Kishore; Chemical communications (Cambridge, England) 60 (2024) 13935–13938; doi:10.1039/d4cc04782f

data_7133879
_publ_section_title
;
 Accessing structurally diverse aryl difluoromethyl ethers with
 bromo(difluoro)acetic acid.
;
_journal_issue                   94
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13935
_journal_page_last               13938
_journal_paper_doi               10.1039/d4cc04782f
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C19 H14 F2 O5 S2'
_chemical_formula_sum            'C19 H14 F2 O5 S2'
_chemical_formula_weight         424.42
_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             2024-08-29
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-08-30 deposited with the CCDC.	2024-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                99.9870(10)
_cell_angle_beta                 97.5440(10)
_cell_angle_gamma                105.3410(10)
_cell_formula_units_Z            2
_cell_length_a                   7.2477(2)
_cell_length_b                   9.2848(3)
_cell_length_c                   14.6674(4)
_cell_measurement_reflns_used    8849
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.022
_cell_measurement_theta_min      2.330
_cell_volume                     920.97(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-IV Photon II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21103
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.212
_diffrn_reflns_theta_min         2.330
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1285 before and 0.0555 after correction.
The Ratio of minimum to maximum transmission is 0.8306.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.455
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.836
_refine_diff_density_min         -0.793
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4075
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0526
_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^)+(0.0522P)^2^+1.0762P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1374
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3312
_reflns_number_total             4075
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04782f2.cif
_cod_data_source_block           mo_kn_sk_dfm_53_2
_cod_depositor_comments          'Adding full bibliography for 7133879.cif.'
_cod_database_code               7133879
_shelx_shelxl_version_number     2019/1
_diffrn_oxdiff_ac3_digest_hkl    41d81ba910ff5454bc6dc2ad74c45837e9406d
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O3-C19 \\sim O3-C19A
 with sigma of 0.02
 F1-C19 \\sim F1A-C19A
 with sigma of 0.02
 F2-C19 \\sim F2A-C19A
 with sigma of 0.02
 O3-F1 \\sim O3-F1A
 with sigma of 0.04
 O3-F2 \\sim O3-F2A
 with sigma of 0.04
 F1-F2 \\sim F1A-F2A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
F1 \\sim C19 \\sim F2: within 2A with sigma of 0.0001 and sigma for terminal
atoms of 0.0002 within 2A
F1A \\sim C19A \\sim F2A: within 2A with sigma of 0.0001 and sigma for terminal
atoms of 0.0002 within 2A
Uanis(F1) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(F2) \\sim Ueq: with sigma of
0.0001 and sigma for terminal atoms of 0.0002
Uanis(F1A) \\sim Ueq, Uanis(C19A) \\sim Ueq, Uanis(F2A) \\sim Ueq: with sigma
of 0.0001 and sigma for terminal atoms of 0.0002
4. Others
 Sof(F1A)=Sof(F2A)=Sof(C19A)=Sof(H19A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(C19)=Sof(H00S)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C19(H00S), C19A(H19A)
5.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C8(H8), C18(H18), C5(H5), C1(H1), C9(H9), C4(H4), C14(H14),
 C17(H17), C3(H3), C16(H16), C15(H15), C2(H2)
;
_shelx_res_checksum              91668
_shelx_hkl_checksum              85121
_olex2_exptl_crystal_mounting_method 'Nylon loop used'
_olex2_submission_special_instructions 'No special instructions were received'