#------------------------------------------------------------------------------
#$Date: 2025-08-05 22:42:00 +0200 (Tue 05 de Aug de 2025) $
#$Revision: 301485 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/46/7134676.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_7134676
loop_
_publ_author_name
'Miele, Margherita'
'Castiglione, Davide'
'Prado-Roller, Alexander'
'Castoldi, Laura'
'Pace, Vittorio'
_publ_section_title
;
 Geminal homologative fluorination of carbonyl derivatives en route
 to 1-fluoro-2-haloethyl skeletons.
;
_journal_issue                   58
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10792
_journal_page_last               10795
_journal_paper_doi               10.1039/d5cc01542a
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C8 H5 Cl4 F'
_chemical_formula_sum            'C8 H5 Cl4 F'
_chemical_formula_weight         261.92
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2024-11-25
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2024.11.02 svn.r19aeb66f for OlexSys, GUI svn.r7078)
;
_audit_update_record
;
2024-12-14 deposited with the CCDC.	2025-06-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.434(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8894(3)
_cell_length_b                   6.0908(3)
_cell_length_c                   16.5497(9)
_cell_measurement_reflns_used    6263
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.552
_cell_measurement_theta_min      2.533
_cell_volume                     990.58(8)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10830
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.543
_diffrn_reflns_theta_min         2.292
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.154
_exptl_absorpt_correction_T_max  0.5645
_exptl_absorpt_correction_T_min  0.5352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0512 before and 0.0366 after correction.
The Ratio of minimum to maximum transmission is 0.9481.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         2927
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0233
_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/[σ²(Fo²)+(0.0256P)²+0.2204P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0561
_refine_ls_wR_factor_ref         0.0596
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2415
_reflns_number_total             2927
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cc01542a2.cif
_cod_data_source_block           mo_vipa_mami980_1_p21n
_cod_depositor_comments          'Adding full bibliography for 7134676.cif.'
_cod_database_code               7134676
_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.
;
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.945
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
Cl1 Cl 0.35875(3) 0.25531(5) 0.42849(2) 0.02229(8) Uani 1 1 d . . . . .
Cl2 Cl 0.66849(3) 0.11043(5) 0.09073(2) 0.01644(8) Uani 1 1 d . . . . .
Cl3 Cl 0.68660(3) -0.32807(6) 0.02586(2) 0.02267(8) Uani 1 1 d . . . . .
Cl4 Cl 0.77557(3) -0.24426(5) 0.19502(2) 0.01768(8) Uani 1 1 d . . . . .
F1A F 0.49685(8) -0.44474(12) 0.14126(5) 0.0207(2) Uani 0.969(2) 1 d . . P A 1
C1 C 0.50728(12) -0.21934(19) 0.13222(8) 0.0154(2) Uani 1 1 d D . . . .
H1B H 0.516034 -0.374546 0.151816 0.018 Uiso 0.031(2) 1 calc R U P A 2
C2 C 0.46846(11) -0.10572(19) 0.20686(7) 0.0131(2) Uani 1 1 d . . . . .
C3 C 0.40546(11) 0.0999(2) 0.19902(8) 0.0135(2) Uani 1 1 d . . . . .
H3 H 0.386546 0.164453 0.146721 0.016 Uiso 1 1 calc R U . . .
C4 C 0.37028(11) 0.21048(19) 0.26697(8) 0.0143(2) Uani 1 1 d . . . . .
H4 H 0.328430 0.350931 0.261773 0.017 Uiso 1 1 calc R U . . .
C5 C 0.39747(11) 0.1118(2) 0.34270(8) 0.0144(2) Uani 1 1 d . . . . .
C6 C 0.45591(11) -0.0951(2) 0.35186(8) 0.0159(2) Uani 1 1 d . . . . .
H6 H 0.471073 -0.161725 0.403991 0.019 Uiso 1 1 calc R U . . .
C7 C 0.49185(12) -0.2031(2) 0.28349(8) 0.0147(2) Uani 1 1 d . . . . .
H7 H 0.532658 -0.344291 0.288927 0.018 Uiso 1 1 calc R U . . .
C8 C 0.65413(12) -0.17325(19) 0.11287(7) 0.0139(2) Uani 1 1 d . . . . .
F1B F 0.426(3) -0.242(4) 0.0689(13) 0.0207(2) Uani 0.031(2) 1 d D . P A 2
H1A H 0.448(2) -0.185(3) 0.0840(13) 0.025 Uiso 0.969(2) 1 d . U P A 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'
Cl Cl 0.1484 0.1585 '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'
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
F1A C1 C2 109.78(10) . . ?
F1A C1 C8 106.56(10) . . ?
F1A C1 H1A 105.2(12) . . ?
C2 C1 H1B 100.9 . . ?
C2 C1 C8 114.75(10) . . ?
C2 C1 H1A 113.2(12) . . ?
C8 C1 H1B 100.9 . . ?
C8 C1 H1A 106.7(12) . . ?
F1B C1 H1B 100.9 . . ?
F1B C1 C2 122.5(13) . . ?
F1B C1 C8 112.2(13) . . ?
C3 C2 C1 119.24(11) . . ?
C7 C2 C1 121.31(11) . . ?
C7 C2 C3 119.45(11) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.59(11) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.70(11) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 Cl1 118.64(9) . . ?
C6 C5 Cl1 119.50(10) . . ?
C6 C5 C4 121.86(11) . . ?
C5 C6 H6 120.6 . . ?
C5 C6 C7 118.85(11) . . ?
C7 C6 H6 120.6 . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.50(11) . . ?
C6 C7 H7 119.8 . . ?
Cl2 C8 Cl3 108.83(7) . . ?
Cl4 C8 Cl2 109.53(6) . . ?
Cl4 C8 Cl3 108.94(6) . . ?
C1 C8 Cl2 108.54(8) . . ?
C1 C8 Cl3 109.26(8) . . ?
C1 C8 Cl4 111.69(9) . . ?
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
Cl1 C5 1.7458(12) . ?
Cl2 C8 1.7752(12) . ?
Cl3 C8 1.7802(12) . ?
Cl4 C8 1.7641(12) . ?
F1A C1 1.3861(14) . ?
C1 H1B 1.0000 . ?
C1 C2 1.5028(17) . ?
C1 C8 1.5474(16) . ?
C1 F1B 1.257(17) . ?
C1 H1A 0.96(2) . ?
C2 C3 1.3982(17) . ?
C2 C7 1.3956(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.3883(17) . ?
C4 H4 0.9500 . ?
C4 C5 1.3888(18) . ?
C5 C6 1.3875(17) . ?
C6 H6 0.9500 . ?
C6 C7 1.3892(18) . ?
C7 H7 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C5 C6 C7 -177.10(9) . . . . ?
F1A C1 C2 C3 -147.69(10) . . . . ?
F1A C1 C2 C7 31.15(15) . . . . ?
F1A C1 C8 Cl2 174.32(8) . . . . ?
F1A C1 C8 Cl3 55.78(11) . . . . ?
F1A C1 C8 Cl4 -64.82(11) . . . . ?
C1 C2 C3 C4 -179.00(10) . . . . ?
C1 C2 C7 C6 179.67(10) . . . . ?
C2 C1 C8 Cl2 -63.96(12) . . . . ?
C2 C1 C8 Cl3 177.50(9) . . . . ?
C2 C1 C8 Cl4 56.90(12) . . . . ?
C2 C3 C4 C5 -0.73(16) . . . . ?
C3 C2 C7 C6 -1.49(17) . . . . ?
C3 C4 C5 Cl1 177.74(8) . . . . ?
C3 C4 C5 C6 -1.36(17) . . . . ?
C4 C5 C6 C7 2.00(17) . . . . ?
C5 C6 C7 C2 -0.54(17) . . . . ?
C7 C2 C3 C4 2.14(17) . . . . ?
C8 C1 C2 C3 92.36(13) . . . . ?
C8 C1 C2 C7 -88.80(13) . . . . ?
F1B C1 C2 C3 -49.5(14) . . . . ?
F1B C1 C2 C7 129.3(14) . . . . ?
F1B C1 C8 Cl2 81.8(13) . . . . ?
F1B C1 C8 Cl3 -36.7(13) . . . . ?
F1B C1 C8 Cl4 -157.3(13) . . . . ?
