#------------------------------------------------------------------------------
#$Date: 2025-03-04 20:09:34 +0200 (Tue, 04 Mar 2025) $
#$Revision: 297991 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/40/7134065.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_7134065
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            'C21 H22 O4'
_chemical_formula_weight         338.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 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                90
_cell_angle_beta                 108.5396(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.4908(4)
_cell_length_b                   8.9534(2)
_cell_length_c                   24.3196(7)
_cell_measurement_reflns_used    9801
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      74.44
_cell_measurement_theta_min      3.83
_cell_volume                     3610.86(16)
_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 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            39618
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.425
_diffrn_reflns_theta_min         3.834
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  0.9819
_exptl_absorpt_correction_T_min  0.8673
_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            colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.249
_exptl_crystal_size_min          0.181
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0411
_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)+(0.0565P)²+1.9216P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1083
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3486
_reflns_number_total             3684
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc05797j2.cif
_cod_data_source_block           ic22493
_cod_depositor_comments
'Adding full bibliography for 7134063--7134065.cif.'
_cod_original_cell_volume        3610.85(16)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7134065
_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   0.772
_shelx_estimated_absorpt_t_max   0.885
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'
'-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
O1 O 0.38744(4) 0.74024(9) 0.39187(3) 0.03143(19) Uani 1 1 d . . . . .
O2 O 0.37096(5) 0.94543(10) 0.44629(4) 0.0423(2) Uani 1 1 d . . . . .
O3 O 0.62843(6) 0.66823(13) 0.49881(6) 0.0715(4) Uani 1 1 d . . . . .
O4 O 0.50403(6) 0.99356(10) 0.34740(4) 0.0486(2) Uani 1 1 d . . . . .
C1 C 0.38676(7) 0.78958(13) 0.44765(5) 0.0347(3) Uani 1 1 d . . . . .
C2 C 0.47337(7) 0.77117(13) 0.48543(5) 0.0374(3) Uani 1 1 d . . . . .
H2A H 0.485680 0.665636 0.497029 0.045 Uiso 1 1 calc R U . . .
H2B H 0.485550 0.834013 0.520665 0.045 Uiso 1 1 calc R U . . .
C3 C 0.51980(7) 0.82331(12) 0.44588(5) 0.0329(2) Uani 1 1 d . . . . .
H3 H 0.520217 0.935001 0.446011 0.039 Uiso 1 1 calc R U . . .
C4 C 0.46469(6) 0.76964(11) 0.38464(4) 0.0273(2) Uani 1 1 d . . . . .
C5 C 0.32552(9) 0.69673(18) 0.46410(6) 0.0508(3) Uani 1 1 d . . . . .
H5A H 0.272367 0.709886 0.435019 0.076 Uiso 1 1 calc R U . . .
H5B H 0.323355 0.728705 0.502117 0.076 Uiso 1 1 calc R U . . .
H5C H 0.341027 0.591219 0.465872 0.076 Uiso 1 1 calc R U . . .
C6 C 0.29439(9) 0.99113(18) 0.40845(7) 0.0574(4) Uani 1 1 d . . . . .
H6A H 0.252455 0.964286 0.425474 0.086 Uiso 1 1 calc R U . . .
H6B H 0.283633 0.941039 0.370920 0.086 Uiso 1 1 calc R U . . .
H6C H 0.294353 1.099543 0.402894 0.086 Uiso 1 1 calc R U . . .
C7 C 0.60675(7) 0.76940(15) 0.46456(6) 0.0442(3) Uani 1 1 d . . . . .
C8 C 0.66407(8) 0.8526(2) 0.44178(7) 0.0578(4) Uani 1 1 d . . . . .
H8A H 0.714210 0.795488 0.449630 0.087 Uiso 1 1 calc R U . . .
H8B H 0.675779 0.950140 0.460886 0.087 Uiso 1 1 calc R U . . .
H8C H 0.639916 0.866793 0.399858 0.087 Uiso 1 1 calc R U . . .
C9 C 0.45461(6) 0.89385(11) 0.33875(5) 0.0310(2) Uani 1 1 d . . . . .
C10 C 0.38505(7) 0.89007(12) 0.28368(5) 0.0324(2) Uani 1 1 d . . . . .
C11 C 0.37587(9) 1.01256(16) 0.24683(6) 0.0475(3) Uani 1 1 d . . . . .
H11 H 0.413412 1.092592 0.256971 0.057 Uiso 1 1 calc R U . . .
C12 C 0.31236(10) 1.0181(2) 0.19555(7) 0.0615(4) Uani 1 1 d . . . . .
H12 H 0.306139 1.102581 0.170867 0.074 Uiso 1 1 calc R U . . .
C13 C 0.25827(9) 0.9026(2) 0.18008(6) 0.0599(4) Uani 1 1 d . . . . .
H13 H 0.214705 0.907186 0.144803 0.072 Uiso 1 1 calc R U . . .
C14 C 0.26723(9) 0.7798(2) 0.21584(6) 0.0553(4) Uani 1 1 d . . . . .
H14 H 0.229906 0.699543 0.204977 0.066 Uiso 1 1 calc R U . . .
C15 C 0.33045(8) 0.77282(15) 0.26758(5) 0.0423(3) Uani 1 1 d . . . . .
H15 H 0.336402 0.687872 0.291994 0.051 Uiso 1 1 calc R U . . .
C16 C 0.49455(6) 0.62613(11) 0.36428(4) 0.0294(2) Uani 1 1 d . . . . .
C17 C 0.47199(8) 0.48839(13) 0.38071(5) 0.0397(3) Uani 1 1 d . . . . .
H17 H 0.436743 0.484269 0.403399 0.048 Uiso 1 1 calc R U . . .
C18 C 0.50061(10) 0.35728(14) 0.36418(6) 0.0506(3) Uani 1 1 d . . . . .
H18 H 0.484620 0.263682 0.375345 0.061 Uiso 1 1 calc R U . . .
C19 C 0.55230(10) 0.36216(15) 0.33154(6) 0.0530(4) Uani 1 1 d . . . . .
H19 H 0.572012 0.272059 0.320395 0.064 Uiso 1 1 calc R U . . .
C20 C 0.57531(9) 0.49818(16) 0.31509(6) 0.0496(3) Uani 1 1 d . . . . .
H20 H 0.611077 0.501437 0.292778 0.060 Uiso 1 1 calc R U . . .
C21 C 0.54636(7) 0.63032(13) 0.33106(5) 0.0378(3) Uani 1 1 d . . . . .
H21 H 0.561918 0.723586 0.319310 0.045 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'
O O 0.0492 0.0322 '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
C1 O1 C4 110.50(8) . . ?
C1 O2 C6 115.70(11) . . ?
O2 C1 O1 109.97(9) . . ?
O2 C1 C5 113.49(10) . . ?
O1 C1 C5 107.60(10) . . ?
O2 C1 C2 105.75(9) . . ?
O1 C1 C2 103.54(9) . . ?
C5 C1 C2 115.99(11) . . ?
C1 C2 C3 102.49(9) . . ?
C2 C3 C7 113.53(10) . . ?
C2 C3 C4 102.50(9) . . ?
C7 C3 C4 116.11(9) . . ?
O1 C4 C16 108.45(8) . . ?
O1 C4 C9 108.87(8) . . ?
C16 C4 C9 110.08(8) . . ?
O1 C4 C3 104.88(8) . . ?
C16 C4 C3 113.26(8) . . ?
C9 C4 C3 111.07(8) . . ?
O3 C7 C8 122.05(12) . . ?
O3 C7 C3 120.61(13) . . ?
C8 C7 C3 117.23(12) . . ?
O4 C9 C10 120.23(10) . . ?
O4 C9 C4 119.52(10) . . ?
C10 C9 C4 120.25(9) . . ?
C15 C10 C11 119.04(12) . . ?
C15 C10 C9 124.04(10) . . ?
C11 C10 C9 116.92(11) . . ?
C12 C11 C10 120.26(14) . . ?
C13 C12 C11 120.46(14) . . ?
C12 C13 C14 119.87(13) . . ?
C13 C14 C15 120.36(14) . . ?
C14 C15 C10 119.99(13) . . ?
C17 C16 C21 119.11(10) . . ?
C17 C16 C4 119.66(10) . . ?
C21 C16 C4 121.19(10) . . ?
C18 C17 C16 120.41(12) . . ?
C19 C18 C17 120.21(13) . . ?
C18 C19 C20 119.93(11) . . ?
C19 C20 C21 120.27(13) . . ?
C20 C21 C16 120.07(12) . . ?
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 C1 1.4304(13) . ?
O1 C4 1.4410(12) . ?
O2 C1 1.4208(14) . ?
O2 C6 1.4226(16) . ?
O3 C7 1.2072(18) . ?
O4 C9 1.2136(14) . ?
C1 C5 1.5070(18) . ?
C1 C2 1.5103(16) . ?
C2 C3 1.5163(17) . ?
C3 C7 1.5209(16) . ?
C3 C4 1.5701(14) . ?
C4 C16 1.5276(14) . ?
C4 C9 1.5455(14) . ?
C7 C8 1.490(2) . ?
C9 C10 1.4963(15) . ?
C10 C15 1.3891(17) . ?
C10 C11 1.3929(17) . ?
C11 C12 1.382(2) . ?
C12 C13 1.371(3) . ?
C13 C14 1.380(2) . ?
C14 C15 1.3875(18) . ?
C16 C17 1.3916(16) . ?
C16 C21 1.3930(16) . ?
C17 C18 1.3849(17) . ?
C18 C19 1.381(2) . ?
C19 C20 1.381(2) . ?
C20 C21 1.3900(17) . ?
