#------------------------------------------------------------------------------
#$Date: 2025-03-04 20:09:34 +0200 (Tue, 04 Mar 2025) $
#$Revision: 297991 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/40/7134063.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_7134063
loop_
_publ_author_name
'Indurmuddam, Ranadheer Reddy'
'Hong, Bor-Cherng'
'Chien, Su-Ying'
_publ_section_title
;
 Synthesis of polysubstituted tetrahydrofurans via visible
 light-induced De Mayo acetalization of benzoylacetones.
;
_journal_issue                   10
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2040
_journal_page_last               2043
_journal_paper_doi               10.1039/d4cc05797j
_journal_volume                  61
_journal_year                    2025
_chemical_formula_sum            'C22 H24 O4'
_chemical_formula_weight         352.41
_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_method           SHELXL-2019/1
_audit_update_record
;
2024-09-06 deposited with the CCDC.	2024-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                111.527(3)
_cell_angle_beta                 96.606(3)
_cell_angle_gamma                104.002(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3493(7)
_cell_length_b                   10.3182(8)
_cell_length_c                   12.4869(10)
_cell_measurement_reflns_used    2296
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      22.23
_cell_measurement_theta_min      2.58
_cell_volume                     945.89(14)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.16'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'Bruker APEX4'
_computing_publication_material  'Bruker APEX4'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_unetI/netI     0.0794
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19902
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         2.219
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9602
_exptl_absorpt_correction_T_min  0.7947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.134
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         5523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0657
_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)+(0.0860P)²+0.0271P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1580
_refine_ls_wR_factor_ref         0.1925
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3186
_reflns_number_total             5523
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc05797j2.cif
_cod_data_source_block           ic22359
_cod_depositor_comments
'Adding full bibliography for 7134063--7134065.cif.'
_cod_original_cell_volume        945.89(13)
_cod_database_code               7134063
_shelx_shelxl_version_number     2019/1
_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_min   0.980
_shelx_estimated_absorpt_t_max   0.989
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
O1 O 0.59896(14) 0.44708(12) 0.16843(9) 0.0375(3) Uani 1 1 d . . . . .
O2 O 0.85214(19) 0.60708(15) 0.45419(11) 0.0590(4) Uani 1 1 d . . . . .
O3 O 0.4341(2) 0.14129(16) 0.28830(16) 0.0737(5) Uani 1 1 d . . . . .
O4 O 0.48606(17) 0.62689(14) 0.27286(11) 0.0471(3) Uani 1 1 d . . . . .
C1 C 0.6844(2) 0.42787(18) 0.26549(14) 0.0355(4) Uani 1 1 d . . . . .
C2 C 0.5447(2) 0.39475(18) 0.33481(15) 0.0392(4) Uani 1 1 d . . . . .
H2 H 0.570891 0.480326 0.412644 0.047 Uiso 1 1 calc R U . . .
C3 C 0.3838(2) 0.3871(2) 0.25891(16) 0.0457(4) Uani 1 1 d . . . . .
H3A H 0.321191 0.284842 0.203414 0.055 Uiso 1 1 calc R U . . .
H3B H 0.308713 0.427901 0.308558 0.055 Uiso 1 1 calc R U . . .
C4 C 0.4463(2) 0.47868(19) 0.19308(15) 0.0408(4) Uani 1 1 d . . . . .
C5 C 0.8273(2) 0.57018(19) 0.34740(15) 0.0405(4) Uani 1 1 d . . . . .
C6 C 0.9365(2) 0.66007(18) 0.29739(15) 0.0378(4) Uani 1 1 d . . . . .
C7 C 0.9472(2) 0.60802(19) 0.17967(15) 0.0421(4) Uani 1 1 d . . . . .
H7 H 0.881928 0.511199 0.126451 0.051 Uiso 1 1 calc R U . . .
C8 C 1.0529(2) 0.6972(2) 0.14001(17) 0.0476(5) Uani 1 1 d . . . . .
H8 H 1.060569 0.661135 0.059627 0.057 Uiso 1 1 calc R U . . .
C9 C 1.1470(3) 0.8381(2) 0.21632(18) 0.0507(5) Uani 1 1 d . . . . .
H9 H 1.218903 0.899041 0.188517 0.061 Uiso 1 1 calc R U . . .
C10 C 1.1367(3) 0.8903(2) 0.33284(18) 0.0546(5) Uani 1 1 d . . . . .
H10 H 1.201365 0.987524 0.385411 0.066 Uiso 1 1 calc R U . . .
C11 C 1.0326(2) 0.8020(2) 0.37377(16) 0.0479(5) Uani 1 1 d . . . . .
H11 H 1.026875 0.838431 0.454541 0.058 Uiso 1 1 calc R U . . .
C12 C 0.7604(2) 0.30345(18) 0.21457(14) 0.0371(4) Uani 1 1 d . . . . .
C13 C 0.8947(2) 0.2906(2) 0.28232(17) 0.0465(4) Uani 1 1 d . . . . .
H13 H 0.945398 0.363701 0.359954 0.056 Uiso 1 1 calc R U . . .
C14 C 0.9556(3) 0.1729(2) 0.2383(2) 0.0562(5) Uani 1 1 d . . . . .
H14 H 1.047026 0.165109 0.285941 0.067 Uiso 1 1 calc R U . . .
C15 C 0.8838(3) 0.0665(2) 0.1253(2) 0.0602(6) Uani 1 1 d . . . . .
H15 H 0.924636 -0.015092 0.095272 0.072 Uiso 1 1 calc R U . . .
C16 C 0.7528(3) 0.0795(2) 0.05652(19) 0.0575(5) Uani 1 1 d . . . . .
H16 H 0.704845 0.007426 -0.021829 0.069 Uiso 1 1 calc R U . . .
C17 C 0.6899(3) 0.19658(19) 0.10017(16) 0.0460(4) Uani 1 1 d . . . . .
H17 H 0.598731 0.203905 0.052033 0.055 Uiso 1 1 calc R U . . .
C18 C 0.5301(3) 0.2580(2) 0.35700(17) 0.0475(5) Uani 1 1 d . . . . .
C19 C 0.6382(3) 0.2759(2) 0.46903(18) 0.0618(6) Uani 1 1 d . . . . .
H19A H 0.578352 0.301537 0.533119 0.093 Uiso 1 1 calc R U . . .
H19B H 0.745063 0.353939 0.489136 0.093 Uiso 1 1 calc R U . . .
H19C H 0.661804 0.183891 0.458131 0.093 Uiso 1 1 calc R U . . .
C20 C 0.3275(3) 0.4398(2) 0.07731(18) 0.0557(5) Uani 1 1 d . . . . .
H20A H 0.379345 0.500598 0.038249 0.083 Uiso 1 1 calc R U . . .
H20B H 0.220380 0.457327 0.092466 0.083 Uiso 1 1 calc R U . . .
H20C H 0.305775 0.336301 0.026170 0.083 Uiso 1 1 calc R U . . .
C21 C 0.5509(3) 0.7340(2) 0.22851(18) 0.0515(5) Uani 1 1 d . . . . .
H21A H 0.459376 0.735539 0.171499 0.062 Uiso 1 1 calc R U . . .
H21B H 0.641356 0.710041 0.187462 0.062 Uiso 1 1 calc R U . . .
C22 C 0.6205(3) 0.8801(2) 0.3311(2) 0.0664(6) Uani 1 1 d . . . . .
H22A H 0.530473 0.902274 0.371696 0.100 Uiso 1 1 calc R U . . .
H22B H 0.663889 0.955607 0.302599 0.100 Uiso 1 1 calc R U . . .
H22C H 0.712674 0.878185 0.386063 0.100 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 0.0033 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'
O O 0.0106 0.0060 '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
C4 O1 C1 109.61(12) . . ?
C4 O4 C21 116.23(14) . . ?
O1 C1 C12 107.94(12) . . ?
O1 C1 C5 110.39(13) . . ?
C12 C1 C5 109.68(14) . . ?
O1 C1 C2 105.20(13) . . ?
C12 C1 C2 114.02(13) . . ?
C5 C1 C2 109.50(13) . . ?
C18 C2 C3 113.06(15) . . ?
C18 C2 C1 114.45(15) . . ?
C3 C2 C1 103.36(13) . . ?
C4 C3 C2 104.04(14) . . ?
O4 C4 O1 109.33(14) . . ?
O4 C4 C3 106.85(14) . . ?
O1 C4 C3 103.61(14) . . ?
O4 C4 C20 113.62(16) . . ?
O1 C4 C20 108.46(14) . . ?
C3 C4 C20 114.44(16) . . ?
O2 C5 C6 120.03(16) . . ?
O2 C5 C1 119.07(15) . . ?
C6 C5 C1 120.88(14) . . ?
C11 C6 C7 119.16(16) . . ?
C11 C6 C5 117.59(16) . . ?
C7 C6 C5 123.26(15) . . ?
C8 C7 C6 119.97(17) . . ?
C9 C8 C7 120.41(18) . . ?
C10 C9 C8 119.88(18) . . ?
C9 C10 C11 120.29(18) . . ?
C10 C11 C6 120.28(18) . . ?
C13 C12 C17 118.66(17) . . ?
C13 C12 C1 121.19(15) . . ?
C17 C12 C1 120.08(16) . . ?
C14 C13 C12 120.88(18) . . ?
C15 C14 C13 120.1(2) . . ?
C16 C15 C14 119.6(2) . . ?
C15 C16 C17 120.8(2) . . ?
C16 C17 C12 120.01(19) . . ?
O3 C18 C19 121.95(18) . . ?
O3 C18 C2 121.14(19) . . ?
C19 C18 C2 116.90(17) . . ?
O4 C21 C22 108.03(16) . . ?
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
O1 C4 1.430(2) . ?
O1 C1 1.4363(19) . ?
O2 C5 1.221(2) . ?
O3 C18 1.202(2) . ?
O4 C4 1.415(2) . ?
O4 C21 1.432(2) . ?
C1 C12 1.530(2) . ?
C1 C5 1.547(2) . ?
C1 C2 1.576(2) . ?
C2 C18 1.515(2) . ?
C2 C3 1.520(3) . ?
C3 C4 1.507(2) . ?
C4 C20 1.512(3) . ?
C5 C6 1.493(2) . ?
C6 C11 1.389(2) . ?
C6 C7 1.390(2) . ?
C7 C8 1.383(3) . ?
C8 C9 1.377(3) . ?
C9 C10 1.375(3) . ?
C10 C11 1.381(3) . ?
C12 C13 1.388(3) . ?
C12 C17 1.393(2) . ?
C13 C14 1.382(3) . ?
C14 C15 1.380(3) . ?
C15 C16 1.376(3) . ?
C16 C17 1.386(3) . ?
C18 C19 1.498(3) . ?
C21 C22 1.496(3) . ?
