#------------------------------------------------------------------------------
#$Date: 2024-01-06 09:38:21 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288765 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/01/1570160.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_1570160
loop_
_publ_author_name
'Sar, Dinabandhu'
'Yin, Shuai'
'Grygus, Jacob'
'Rentería-Gómez, Ángel'
'Garcia, Melanie'
'Gutierrez, Osvaldo'
_publ_section_title
;
 Expanding the chemical space of enol silyl ethers: catalytic
 dicarbofunctionalization enabled by iron catalysis.
;
_journal_issue                   45
_journal_name_full               'Chemical science'
_journal_page_first              13007
_journal_page_last               13013
_journal_paper_doi               10.1039/d3sc04549h
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H12 F2 O3'
_chemical_formula_sum            'C16 H12 F2 O3'
_chemical_formula_weight         290.26
_chemical_name_systematic
3,3-Difluoro-5-(4-phenoxyphenyl)dihydrofuran-2(3H)-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-07
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-10-17 deposited with the CCDC.	2023-10-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   29.2415(18)
_cell_length_b                   7.5874(5)
_cell_length_c                   6.0208(4)
_cell_measurement_reflns_used    6291
_cell_measurement_temperature    110.00
_cell_measurement_theta_max      62.403
_cell_measurement_theta_min      3.022
_cell_volume                     1335.82(15)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'APEX 3 (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      110.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Venture (PHOTON III)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            13669
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        62.574
_diffrn_reflns_theta_max         62.574
_diffrn_reflns_theta_min         3.022
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.004
_exptl_absorpt_correction_T_max  0.7522
_exptl_absorpt_correction_T_min  0.6696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0895 before and 0.0645 after correction.
The Ratio of minimum to maximum transmission is 0.8902.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: mixture of Hexane and chloroform'
_exptl_crystal_size_max          0.129
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.008
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.3(2)
_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     191
_refine_ls_number_reflns         2091
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0334
_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)+(0.0414P)²+0.2694P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0820
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    0.958
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                1940
_reflns_number_total             2091
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc04549h2.cif
_cod_data_source_block           og388
_cod_depositor_comments
'Adding full bibliography for 1570159--1570162.cif.'
_cod_database_code               1570160
_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.
;
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.881
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7(2)
 0.3(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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
F1 F 0.48237(6) 0.9534(2) 0.6871(4) 0.0398(5) Uani 1 1 d . . . . .
F2 F 0.52089(6) 0.7499(3) 0.5165(3) 0.0363(5) Uani 1 1 d . . . . .
O1 O 0.43086(7) 0.5532(3) 0.6549(4) 0.0262(5) Uani 1 1 d . . . . .
O2 O 0.47531(8) 0.6366(3) 0.9393(4) 0.0375(6) Uani 1 1 d . . . . .
O3 O 0.24758(7) 0.5493(3) 0.0656(4) 0.0261(5) Uani 1 1 d . . . . .
C1 C 0.46235(11) 0.6552(4) 0.7525(6) 0.0266(8) Uani 1 1 d . . . . .
C2 C 0.47792(10) 0.7942(4) 0.5865(6) 0.0263(7) Uani 1 1 d . . . . .
C3 C 0.44317(10) 0.7898(4) 0.4055(6) 0.0251(7) Uani 1 1 d . . . . .
H3A H 0.457177 0.815090 0.259176 0.030 Uiso 1 1 calc R U . . .
H3B H 0.418208 0.875115 0.433369 0.030 Uiso 1 1 calc R U . . .
C4 C 0.42582(9) 0.5988(4) 0.4184(5) 0.0226(7) Uani 1 1 d . . . . .
H4 H 0.446321 0.521431 0.328051 0.027 Uiso 1 1 calc R U . . .
C5 C 0.37756(10) 0.5737(4) 0.3437(5) 0.0200(7) Uani 1 1 d . . . . .
C6 C 0.36889(10) 0.4848(4) 0.1461(6) 0.0220(7) Uani 1 1 d . . . . .
H6 H 0.393491 0.431272 0.068145 0.026 Uiso 1 1 calc R U . . .
C7 C 0.32518(10) 0.4730(4) 0.0614(5) 0.0218(7) Uani 1 1 d . . . . .
H7 H 0.319697 0.411533 -0.073470 0.026 Uiso 1 1 calc R U . . .
C8 C 0.28921(9) 0.5518(3) 0.1751(6) 0.0197(6) Uani 1 1 d . . . . .
C9 C 0.29678(10) 0.6380(4) 0.3753(5) 0.0218(7) Uani 1 1 d . . . . .
H9 H 0.271999 0.688988 0.454565 0.026 Uiso 1 1 calc R U . . .
C10 C 0.34082(10) 0.6486(4) 0.4578(5) 0.0218(7) Uani 1 1 d . . . . .
H10 H 0.346168 0.707775 0.594439 0.026 Uiso 1 1 calc R U . . .
C11 C 0.20677(9) 0.5523(3) 0.1833(6) 0.0202(6) Uani 1 1 d . . . . .
C12 C 0.20054(11) 0.4617(3) 0.3807(6) 0.0240(7) Uani 1 1 d . . . . .
H12 H 0.225271 0.400226 0.447594 0.029 Uiso 1 1 calc R U . . .
C13 C 0.15772(10) 0.4619(4) 0.4792(6) 0.0252(7) Uani 1 1 d . . . . .
H13 H 0.153103 0.399525 0.614194 0.030 Uiso 1 1 calc R U . . .
C14 C 0.12167(11) 0.5516(4) 0.3835(6) 0.0281(8) Uani 1 1 d . . . . .
H14 H 0.092494 0.552083 0.452910 0.034 Uiso 1 1 calc R U . . .
C15 C 0.12837(10) 0.6408(4) 0.1858(6) 0.0276(7) Uani 1 1 d . . . . .
H15 H 0.103536 0.701286 0.118497 0.033 Uiso 1 1 calc R U . . .
C16 C 0.17090(11) 0.6427(4) 0.0853(5) 0.0256(7) Uani 1 1 d . . . . .
H16 H 0.175453 0.705305 -0.049577 0.031 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 0.00 0.00 0.0040
-1.00 0.00 0.00 0.0030
0.00 1.00 0.00 0.0240
0.00 -1.00 0.00 0.0360
1.00 0.00 1.00 0.0630
-1.00 0.00 -1.00 0.0580
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
C1 O1 C4 110.9(2) . . ?
C8 O3 C11 120.8(2) . . ?
O1 C1 C2 108.5(3) . . ?
O2 C1 O1 124.3(3) . . ?
O2 C1 C2 127.2(3) . . ?
F1 C2 F2 105.5(2) . . ?
F1 C2 C1 110.6(3) . . ?
F1 C2 C3 114.3(3) . . ?
F2 C2 C1 107.9(2) . . ?
F2 C2 C3 113.3(3) . . ?
C3 C2 C1 105.1(2) . . ?
C2 C3 H3A 111.4 . . ?
C2 C3 H3B 111.4 . . ?
C2 C3 C4 102.1(2) . . ?
H3A C3 H3B 109.2 . . ?
C4 C3 H3A 111.4 . . ?
C4 C3 H3B 111.4 . . ?
O1 C4 C3 103.7(2) . . ?
O1 C4 H4 109.1 . . ?
O1 C4 C5 110.8(2) . . ?
C3 C4 H4 109.1 . . ?
C5 C4 C3 114.6(2) . . ?
C5 C4 H4 109.1 . . ?
C6 C5 C4 119.4(3) . . ?
C6 C5 C10 118.6(3) . . ?
C10 C5 C4 121.8(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.1(3) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 120.3 . . ?
C6 C7 C8 119.4(3) . . ?
C8 C7 H7 120.3 . . ?
O3 C8 C7 115.1(3) . . ?
O3 C8 C9 124.0(3) . . ?
C9 C8 C7 120.6(3) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 C8 119.2(3) . . ?
C10 C9 H9 120.4 . . ?
C5 C10 H10 119.5 . . ?
C9 C10 C5 121.1(3) . . ?
C9 C10 H10 119.5 . . ?
C12 C11 O3 122.9(3) . . ?
C16 C11 O3 116.2(3) . . ?
C16 C11 C12 120.8(3) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.1(3) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.5(3) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C11 C16 H16 120.4 . . ?
C15 C16 C11 119.3(3) . . ?
C15 C16 H16 120.4 . . ?
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
F1 C2 1.358(3) . ?
F2 C2 1.367(3) . ?
O1 C1 1.338(4) . ?
O1 C4 1.473(4) . ?
O2 C1 1.196(4) . ?
O3 C8 1.385(4) . ?
O3 C11 1.388(4) . ?
C1 C2 1.523(5) . ?
C2 C3 1.490(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.537(4) . ?
C4 H4 1.0000 . ?
C4 C5 1.493(4) . ?
C5 C6 1.391(5) . ?
C5 C10 1.396(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.379(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.390(4) . ?
C8 C9 1.389(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(5) . ?
C11 C16 1.385(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.381(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(4) . ?
C16 H16 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
F1 C2 C3 C4 -148.7(3) . . . . ?
F2 C2 C3 C4 90.3(3) . . . . ?
O1 C1 C2 F1 138.4(3) . . . . ?
O1 C1 C2 F2 -106.6(3) . . . . ?
O1 C1 C2 C3 14.6(3) . . . . ?
O1 C4 C5 C6 -133.1(3) . . . . ?
O1 C4 C5 C10 51.8(3) . . . . ?
O2 C1 C2 F1 -41.5(4) . . . . ?
O2 C1 C2 F2 73.5(4) . . . . ?
O2 C1 C2 C3 -165.3(3) . . . . ?
O3 C8 C9 C10 -172.9(3) . . . . ?
O3 C11 C12 C13 -175.5(3) . . . . ?
O3 C11 C16 C15 175.6(3) . . . . ?
C1 O1 C4 C3 -23.1(3) . . . . ?
C1 O1 C4 C5 -146.6(2) . . . . ?
C1 C2 C3 C4 -27.3(3) . . . . ?
C2 C3 C4 O1 30.4(3) . . . . ?
C2 C3 C4 C5 151.4(3) . . . . ?
C3 C4 C5 C6 109.9(3) . . . . ?
C3 C4 C5 C10 -65.2(4) . . . . ?
C4 O1 C1 O2 -174.3(3) . . . . ?
C4 O1 C1 C2 5.7(3) . . . . ?
C4 C5 C6 C7 -174.0(3) . . . . ?
C4 C5 C10 C9 173.9(3) . . . . ?
C5 C6 C7 C8 0.2(4) . . . . ?
C6 C5 C10 C9 -1.2(4) . . . . ?
C6 C7 C8 O3 173.3(3) . . . . ?
C6 C7 C8 C9 -1.7(4) . . . . ?
C7 C8 C9 C10 1.7(4) . . . . ?
C8 O3 C11 C12 -38.5(4) . . . . ?
C8 O3 C11 C16 145.6(3) . . . . ?
C8 C9 C10 C5 -0.2(4) . . . . ?
C10 C5 C6 C7 1.2(4) . . . . ?
C11 O3 C8 C7 152.8(3) . . . . ?
C11 O3 C8 C9 -32.4(4) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C12 C11 C16 C15 -0.5(4) . . . . ?
C12 C13 C14 C15 0.6(4) . . . . ?
C13 C14 C15 C16 -0.9(4) . . . . ?
C14 C15 C16 C11 0.8(4) . . . . ?
C16 C11 C12 C13 0.2(4) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.7(2)
2 0.3(2)
