#------------------------------------------------------------------------------
#$Date: 2024-12-06 18:18:27 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296348 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/28/1572874.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_1572874
loop_
_publ_author_name
'Huang, Shisheng'
'Luo, Jilong'
'Chen, Ping'
'Chen, Jiean'
'Wang, Zhaofeng'
_publ_section_title
;
 Three-component modular synthesis of chiral 1,3-dioxoles via a
 Rh-catalyzed carbenic olefination cascade.
;
_journal_issue                   44
_journal_name_full               'Chemical science'
_journal_page_first              18564
_journal_page_last               18571
_journal_paper_doi               10.1039/d4sc06166g
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H20 O4'
_chemical_formula_weight         372.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-09-12 deposited with the CCDC.	2024-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.57076(8)
_cell_length_b                   7.79768(12)
_cell_length_c                   42.0452(6)
_cell_measurement_reflns_used    7349
_cell_measurement_temperature    105(2)
_cell_measurement_theta_max      76.1640
_cell_measurement_theta_min      2.1050
_cell_volume                     1826.40(5)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      105(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            9451
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.348
_diffrn_reflns_theta_min         2.102
_exptl_absorpt_coefficient_mu    0.742
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1325 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(9)
_refine_ls_extinction_coef       0.0018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0317
_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)+(0.0384P)²+0.2399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0803
_reflns_Friedel_coverage         0.654
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.928
_reflns_number_gt                3456
_reflns_number_total             3628
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc06166g2.cif
_cod_data_source_block           wzf-20230712_auto
_cod_depositor_comments          'Adding full bibliography for 1572874.cif.'
_cod_database_code               1572874
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
O8 O -1.0131(2) -0.87192(17) -0.63437(3) 0.0268(3) Uani 1 1 d . . . . .
O11 O -1.2229(2) -0.63168(16) -0.62131(3) 0.0268(3) Uani 1 1 d . . . . .
O21 O -0.8932(3) -0.35504(18) -0.67205(4) 0.0375(4) Uani 1 1 d . . . . .
O18 O -0.1962(3) -0.93871(19) -0.73646(4) 0.0332(3) Uani 1 1 d . . . . .
C23 C -1.2646(3) -1.0239(2) -0.48637(4) 0.0201(4) Uani 1 1 d . . . . .
C4 C -1.2596(3) -0.9684(2) -0.52039(4) 0.0202(4) Uani 1 1 d . . . . .
C1 C -1.2394(3) -0.8695(2) -0.58487(4) 0.0224(4) Uani 1 1 d . . . . .
C26 C -1.2692(3) -1.1334(2) -0.42244(4) 0.0254(4) Uani 1 1 d . . . . .
H26 H -1.270917 -1.170422 -0.400920 0.030 Uiso 1 1 calc R U . . .
C7 C -1.2302(4) -0.8145(2) -0.61904(5) 0.0251(4) Uani 1 1 d . . . . .
H7 H -1.373416 -0.859685 -0.630687 0.030 Uiso 1 1 calc R U . . .
C24 C -1.0823(3) -0.9786(2) -0.46517(5) 0.0260(4) Uani 1 1 d . . . . .
H24 H -0.953626 -0.909096 -0.472485 0.031 Uiso 1 1 calc R U . . .
C9 C -0.9276(3) -0.7366(2) -0.65228(4) 0.0227(4) Uani 1 1 d . . . . .
C2 C -1.0597(4) -0.8206(2) -0.56389(5) 0.0276(4) Uani 1 1 d . . . . .
H2 H -0.929170 -0.753014 -0.571270 0.033 Uiso 1 1 calc R U . . .
C10 C -1.0521(3) -0.5932(2) -0.64463(4) 0.0228(4) Uani 1 1 d . . . . .
C5 C -1.4396(3) -1.0146(3) -0.54169(4) 0.0258(4) Uani 1 1 d . . . . .
H5 H -1.571610 -1.080669 -0.534332 0.031 Uiso 1 1 calc R U . . .
C12 C -0.7365(3) -0.7813(2) -0.67448(4) 0.0226(4) Uani 1 1 d . . . . .
C27 C -1.4526(4) -1.1799(3) -0.44300(4) 0.0283(4) Uani 1 1 d . . . . .
H27 H -1.580601 -1.249520 -0.435507 0.034 Uiso 1 1 calc R U . . .
C3 C -1.0693(4) -0.8695(3) -0.53231(5) 0.0266(4) Uani 1 1 d . . . . .
H3 H -0.944089 -0.835418 -0.518343 0.032 Uiso 1 1 calc R U . . .
C6 C -1.4304(3) -0.9660(2) -0.57358(5) 0.0259(4) Uani 1 1 d . . . . .
H6 H -1.555541 -0.999106 -0.587646 0.031 Uiso 1 1 calc R U . . .
C28 C -1.4507(3) -1.1255(3) -0.47444(4) 0.0258(4) Uani 1 1 d . . . . .
H28 H -1.578520 -1.158035 -0.488126 0.031 Uiso 1 1 calc R U . . .
C25 C -1.0840(3) -1.0325(2) -0.43367(5) 0.0282(4) Uani 1 1 d . . . . .
H25 H -0.957295 -0.999762 -0.419814 0.034 Uiso 1 1 calc R U . . .
C17 C -0.5965(3) -0.6585(2) -0.68995(4) 0.0260(4) Uani 1 1 d . . . . .
H17 H -0.626304 -0.540293 -0.686196 0.031 Uiso 1 1 calc R U . . .
C20 C -1.0492(4) -0.4139(2) -0.65458(4) 0.0251(4) Uani 1 1 d . . . . .
C16 C -0.4144(4) -0.7060(3) -0.71073(5) 0.0280(4) Uani 1 1 d . . . . .
H16 H -0.320151 -0.620675 -0.720936 0.034 Uiso 1 1 calc R U . . .
C15 C -0.3702(4) -0.8790(3) -0.71659(4) 0.0268(4) Uani 1 1 d . . . . .
C14 C -0.5100(4) -1.0025(3) -0.70152(4) 0.0280(4) Uani 1 1 d . . . . .
H14 H -0.480676 -1.120532 -0.705576 0.034 Uiso 1 1 calc R U . . .
C13 C -0.6908(4) -0.9560(2) -0.68074(4) 0.0259(4) Uani 1 1 d . . . . .
H13 H -0.784589 -1.041904 -0.670643 0.031 Uiso 1 1 calc R U . . .
C19 C -0.0434(4) -0.8150(3) -0.75115(5) 0.0341(5) Uani 1 1 d . . . . .
H19A H 0.075718 -0.873783 -0.764383 0.051 Uiso 1 1 calc R U . . .
H19B H 0.038831 -0.748069 -0.734697 0.051 Uiso 1 1 calc R U . . .
H19C H -0.139835 -0.738114 -0.764445 0.051 Uiso 1 1 calc R U . . .
C22 C -1.2469(4) -0.3023(2) -0.64186(5) 0.0287(4) Uani 1 1 d . . . . .
H22A H -1.238919 -0.299953 -0.618584 0.043 Uiso 1 1 calc R U . . .
H22B H -1.402452 -0.348535 -0.648552 0.043 Uiso 1 1 calc R U . . .
H22C H -1.228190 -0.185605 -0.650159 0.043 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
C9 O8 C7 107.22(14) . . ?
C10 O11 C7 106.26(14) . . ?
C15 O18 C19 117.32(16) . . ?
C24 C23 C28 116.96(16) . . ?
C24 C23 C4 121.60(16) . . ?
C28 C23 C4 121.43(16) . . ?
C5 C4 C3 117.16(17) . . ?
C5 C4 C23 121.82(15) . . ?
C3 C4 C23 121.01(16) . . ?
C6 C1 C2 119.02(16) . . ?
C6 C1 C7 120.58(17) . . ?
C2 C1 C7 120.38(17) . . ?
C25 C26 C27 119.12(17) . . ?
C25 C26 H26 120.4 . . ?
C27 C26 H26 120.4 . . ?
O11 C7 O8 104.82(14) . . ?
O11 C7 C1 110.47(15) . . ?
O8 C7 C1 111.59(15) . . ?
O11 C7 H7 110.0 . . ?
O8 C7 H7 110.0 . . ?
C1 C7 H7 110.0 . . ?
C25 C24 C23 121.81(17) . . ?
C25 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
C10 C9 O8 108.93(15) . . ?
C10 C9 C12 136.33(17) . . ?
O8 C9 C12 114.72(15) . . ?
C3 C2 C1 120.43(17) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C9 C10 O11 109.75(15) . . ?
C9 C10 C20 135.81(18) . . ?
O11 C10 C20 114.43(16) . . ?
C4 C5 C6 121.47(17) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C17 C12 C13 118.31(17) . . ?
C17 C12 C9 122.85(17) . . ?
C13 C12 C9 118.84(16) . . ?
C26 C27 C28 120.53(18) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C2 C3 C4 121.62(18) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C1 C6 C5 120.30(17) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C27 C28 C23 121.36(18) . . ?
C27 C28 H28 119.3 . . ?
C23 C28 H28 119.3 . . ?
C26 C25 C24 120.21(18) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C16 C17 C12 121.24(18) . . ?
C16 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?
O21 C20 C10 122.52(18) . . ?
O21 C20 C22 121.06(17) . . ?
C10 C20 C22 116.41(17) . . ?
C17 C16 C15 119.88(18) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
O18 C15 C14 116.17(18) . . ?
O18 C15 C16 124.41(18) . . ?
C14 C15 C16 119.42(18) . . ?
C13 C14 C15 120.93(18) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C13 C12 120.23(18) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
O18 C19 H19A 109.5 . . ?
O18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
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
O8 C9 1.381(2) . ?
O8 C7 1.442(2) . ?
O11 C10 1.399(2) . ?
O11 C7 1.430(2) . ?
O21 C20 1.227(2) . ?
O18 C15 1.362(2) . ?
O18 C19 1.427(3) . ?
C23 C24 1.397(3) . ?
C23 C28 1.398(3) . ?
C23 C4 1.495(2) . ?
C4 C5 1.392(3) . ?
C4 C3 1.403(3) . ?
C1 C6 1.387(3) . ?
C1 C2 1.388(3) . ?
C1 C7 1.500(3) . ?
C26 C25 1.381(3) . ?
C26 C27 1.387(3) . ?
C26 H26 0.9500 . ?
C7 H7 1.0000 . ?
C24 C25 1.389(3) . ?
C24 H24 0.9500 . ?
C9 C10 1.354(3) . ?
C9 C12 1.458(3) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9500 . ?
C10 C20 1.460(2) . ?
C5 C6 1.395(3) . ?
C5 H5 0.9500 . ?
C12 C17 1.396(3) . ?
C12 C13 1.411(3) . ?
C27 C28 1.388(3) . ?
C27 H27 0.9500 . ?
C3 H3 0.9500 . ?
C6 H6 0.9500 . ?
C28 H28 0.9500 . ?
C25 H25 0.9500 . ?
C17 C16 1.389(3) . ?
C17 H17 0.9500 . ?
C20 C22 1.502(3) . ?
C16 C15 1.393(3) . ?
C16 H16 0.9500 . ?
C15 C14 1.391(3) . ?
C14 C13 1.382(3) . ?
C14 H14 0.9500 . ?
C13 H13 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
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
C24 C23 C4 C5 179.34(18) . . . . ?
C28 C23 C4 C5 0.2(3) . . . . ?
C24 C23 C4 C3 0.5(3) . . . . ?
C28 C23 C4 C3 -178.57(18) . . . . ?
C10 O11 C7 O8 16.67(18) . . . . ?
C10 O11 C7 C1 137.00(15) . . . . ?
C9 O8 C7 O11 -16.82(18) . . . . ?
C9 O8 C7 C1 -136.40(15) . . . . ?
C6 C1 C7 O11 120.38(19) . . . . ?
C2 C1 C7 O11 -57.9(2) . . . . ?
C6 C1 C7 O8 -123.44(18) . . . . ?
C2 C1 C7 O8 58.3(2) . . . . ?
C28 C23 C24 C25 0.3(3) . . . . ?
C4 C23 C24 C25 -178.81(17) . . . . ?
C7 O8 C9 C10 10.6(2) . . . . ?
C7 O8 C9 C12 -168.12(15) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C7 C1 C2 C3 179.27(17) . . . . ?
O8 C9 C10 O11 0.1(2) . . . . ?
C12 C9 C10 O11 178.46(19) . . . . ?
O8 C9 C10 C20 179.8(2) . . . . ?
C12 C9 C10 C20 -1.9(4) . . . . ?
C7 O11 C10 C9 -10.9(2) . . . . ?
C7 O11 C10 C20 169.40(16) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C23 C4 C5 C6 -178.33(17) . . . . ?
C10 C9 C12 C17 14.6(3) . . . . ?
O8 C9 C12 C17 -167.18(17) . . . . ?
C10 C9 C12 C13 -165.3(2) . . . . ?
O8 C9 C12 C13 13.0(2) . . . . ?
C25 C26 C27 C28 -0.2(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C5 C4 C3 C2 -0.3(3) . . . . ?
C23 C4 C3 C2 178.53(17) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
C7 C1 C6 C5 -179.08(17) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C26 C27 C28 C23 0.4(3) . . . . ?
C24 C23 C28 C27 -0.5(3) . . . . ?
C4 C23 C28 C27 178.65(17) . . . . ?
C27 C26 C25 C24 0.0(3) . . . . ?
C23 C24 C25 C26 -0.1(3) . . . . ?
C13 C12 C17 C16 -0.8(3) . . . . ?
C9 C12 C17 C16 179.39(17) . . . . ?
C9 C10 C20 O21 -8.1(4) . . . . ?
O11 C10 C20 O21 171.50(17) . . . . ?
C9 C10 C20 C22 172.8(2) . . . . ?
O11 C10 C20 C22 -7.6(2) . . . . ?
C12 C17 C16 C15 0.5(3) . . . . ?
C19 O18 C15 C14 -177.32(17) . . . . ?
C19 O18 C15 C16 2.7(3) . . . . ?
C17 C16 C15 O18 -179.90(17) . . . . ?
C17 C16 C15 C14 0.1(3) . . . . ?
O18 C15 C14 C13 179.67(17) . . . . ?
C16 C15 C14 C13 -0.3(3) . . . . ?
C15 C14 C13 C12 0.0(3) . . . . ?
C17 C12 C13 C14 0.5(3) . . . . ?
C9 C12 C13 C14 -179.61(17) . . . . ?
