#------------------------------------------------------------------------------
#$Date: 2022-06-06 04:47:48 +0300 (Mon, 06 Jun 2022) $
#$Revision: 275786 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/46/7244665.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_7244665
loop_
_publ_author_name
'Chen, Li'
'Niu, Shengtong'
'Lan, Shouang'
'Liu, Wenjun'
'Yang, Shuang'
'Fang, Xinqiang'
_publ_section_title
;
 Organocatalyzed trifunctionalization of alkynyl 1,2-diones for the
 concise synthesis of acyloxy allylidene malonates and
 γ-alkylidenebutenolides
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              3623
_journal_page_last               3628
_journal_paper_doi               10.1039/D2GC00061J
_journal_volume                  24
_journal_year                    2022
_chemical_formula_sum            'C23 H20 O6'
_chemical_formula_weight         392.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-12-29 deposited with the CCDC.	2022-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.0593(7)
_cell_length_b                   16.1161(10)
_cell_length_c                   20.7106(9)
_cell_measurement_reflns_used    19057
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      60.329
_cell_measurement_theta_min      3.984
_cell_volume                     4025.1(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.3414
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            52295
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        53.595
_diffrn_reflns_theta_max         61.012
_diffrn_reflns_theta_min         3.714
_exptl_absorpt_coefficient_mu    0.494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.0014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4591
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0670
_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)+(0.1099P)²+2.4210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1843
_refine_ls_wR_factor_ref         0.2027
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3706
_reflns_number_total             4591
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2gc00061j2.cif
_cod_data_source_block           CL-1_auto
_cod_depositor_comments
'Adding full bibliography for 7244664--7244667.cif.'
_cod_database_code               7244665
_shelx_shelxl_version_number     2014/7
_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   0.908
_shelx_estimated_absorpt_t_max   0.908
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, 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
O8 O 0.20891(12) 0.62856(10) 0.44495(6) 0.0371(4) Uani 1 1 d . . . . .
O18 O 0.34879(12) 0.69051(10) 0.25139(6) 0.0364(4) Uani 1 1 d . . . . .
O9 O 0.52653(13) 0.31968(10) 0.48644(7) 0.0398(4) Uani 1 1 d . . . . .
O29 O 0.24489(15) 0.63320(11) 0.17260(7) 0.0476(4) Uani 1 1 d . . . . .
O28 O 0.08978(14) 0.50429(11) 0.23565(8) 0.0490(5) Uani 1 1 d . . . . .
O24 O 0.11914(14) 0.49925(11) 0.34329(8) 0.0507(5) Uani 1 1 d . . . . .
C1 C 0.33829(16) 0.51982(13) 0.42655(9) 0.0311(4) Uani 1 1 d . . . . .
C7 C 0.26929(15) 0.59115(13) 0.40804(9) 0.0312(4) Uani 1 1 d . . . . .
C6 C 0.41784(16) 0.48708(13) 0.38486(9) 0.0318(4) Uani 1 1 d . . . . .
H6 H 0.4270 0.5105 0.3442 0.038 Uiso 1 1 calc R U . . .
C20 C 0.27836(15) 0.61932(13) 0.33842(9) 0.0319(4) Uani 1 1 d . . . . .
C19 C 0.35726(16) 0.68089(13) 0.31800(9) 0.0321(4) Uani 1 1 d . . . . .
C4 C 0.46856(17) 0.38562(13) 0.46362(9) 0.0337(4) Uani 1 1 d . . . . .
C21 C 0.22197(17) 0.59260(14) 0.28585(9) 0.0352(5) Uani 1 1 d . . . . .
C5 C 0.48354(17) 0.42049(13) 0.40267(9) 0.0333(4) Uani 1 1 d . . . . .
H5 H 0.5366 0.3994 0.3745 0.040 Uiso 1 1 calc R U . . .
C2 C 0.32626(18) 0.48485(14) 0.48822(9) 0.0361(5) Uani 1 1 d . . . . .
H2 H 0.2749 0.5069 0.5170 0.043 Uiso 1 1 calc R U . . .
C17 C 0.42948(16) 0.72162(14) 0.35591(9) 0.0340(4) Uani 1 1 d . . . . .
H17 H 0.4230 0.7093 0.3996 0.041 Uiso 1 1 calc R U . . .
C22 C 0.26571(18) 0.63717(14) 0.22938(9) 0.0372(5) Uani 1 1 d . . . . .
C23 C 0.13676(18) 0.52766(15) 0.28376(10) 0.0391(5) Uani 1 1 d . . . . .
C11 C 0.51519(17) 0.78098(15) 0.34115(10) 0.0376(5) Uani 1 1 d . . . . .
C3 C 0.39013(18) 0.41818(15) 0.50615(9) 0.0397(5) Uani 1 1 d . . . . .
H3 H 0.3811 0.3946 0.5468 0.048 Uiso 1 1 calc R U . . .
C10 C 0.61588(18) 0.28863(15) 0.44804(10) 0.0383(5) Uani 1 1 d . . . . .
H10A H 0.5879 0.2709 0.4069 0.057 Uiso 1 1 calc R U . . .
H10B H 0.6499 0.2425 0.4697 0.057 Uiso 1 1 calc R U . . .
H10C H 0.6699 0.3317 0.4418 0.057 Uiso 1 1 calc R U . . .
C16 C 0.54070(19) 0.80881(16) 0.27882(11) 0.0454(6) Uani 1 1 d . . . . .
H16 H 0.4992 0.7903 0.2438 0.055 Uiso 1 1 calc R U . . .
C12 C 0.5766(2) 0.81115(18) 0.39301(12) 0.0526(7) Uani 1 1 d . . . . .
H12 H 0.5599 0.7937 0.4347 0.063 Uiso 1 1 calc R U . . .
C15 C 0.6271(2) 0.8635(2) 0.26920(14) 0.0593(7) Uani 1 1 d . . . . .
H15 H 0.6447 0.8809 0.2276 0.071 Uiso 1 1 calc R U . . .
C25 C 0.0424(2) 0.43008(19) 0.35231(13) 0.0602(8) Uani 1 1 d . . . . .
H25 H -0.0193 0.4344 0.3217 0.072 Uiso 1 1 calc R U . . .
C14 C 0.6879(2) 0.8927(2) 0.32126(16) 0.0697(9) Uani 1 1 d . . . . .
H14 H 0.7461 0.9295 0.3146 0.084 Uiso 1 1 calc R U . . .
C13 C 0.6621(3) 0.8669(2) 0.38322(15) 0.0690(9) Uani 1 1 d . . . . .
H13 H 0.7022 0.8870 0.4182 0.083 Uiso 1 1 calc R U . . .
C26 C 0.0003(3) 0.4381(2) 0.42062(16) 0.0747(9) Uani 1 1 d . . . . .
H26A H 0.0595 0.4265 0.4503 0.112 Uiso 1 1 calc R U . . .
H26B H -0.0591 0.3994 0.4274 0.112 Uiso 1 1 calc R U . . .
H26C H -0.0263 0.4935 0.4276 0.112 Uiso 1 1 calc R U . . .
C27 C 0.1053(4) 0.3518(2) 0.3409(2) 0.0996(15) Uani 1 1 d . . . . .
H27A H 0.1368 0.3527 0.2983 0.149 Uiso 1 1 calc R U . . .
H27B H 0.0561 0.3052 0.3447 0.149 Uiso 1 1 calc R U . . .
H27C H 0.1636 0.3469 0.3722 0.149 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 0.0137 0.0067 '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 0.0389 0.0241 '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
C19 O18 C22 107.91(15) . . ?
C4 O9 C10 117.95(15) . . ?
C23 O24 C25 118.80(18) . . ?
C6 C1 C2 118.86(19) . . ?
C6 C1 C7 121.60(17) . . ?
C2 C1 C7 119.52(17) . . ?
O8 C7 C1 124.26(17) . . ?
O8 C7 C20 119.53(18) . . ?
C1 C7 C20 116.19(16) . . ?
C5 C6 C1 121.49(17) . . ?
C21 C20 C19 108.38(17) . . ?
C21 C20 C7 129.31(19) . . ?
C19 C20 C7 122.28(17) . . ?
C17 C19 O18 124.90(18) . . ?
C17 C19 C20 126.44(17) . . ?
O18 C19 C20 108.64(16) . . ?
O9 C4 C5 124.36(18) . . ?
O9 C4 C3 115.09(17) . . ?
C5 C4 C3 120.54(19) . . ?
C20 C21 C23 127.04(19) . . ?
C20 C21 C22 107.70(19) . . ?
C23 C21 C22 125.18(18) . . ?
C6 C5 C4 118.68(18) . . ?
C3 C2 C1 120.15(19) . . ?
C19 C17 C11 131.69(18) . . ?
O29 C22 O18 120.1(2) . . ?
O29 C22 C21 132.5(2) . . ?
O18 C22 C21 107.37(16) . . ?
O28 C23 O24 125.6(2) . . ?
O28 C23 C21 125.2(2) . . ?
O24 C23 C21 109.24(17) . . ?
C12 C11 C16 118.8(2) . . ?
C12 C11 C17 116.72(19) . . ?
C16 C11 C17 124.4(2) . . ?
C2 C3 C4 120.27(18) . . ?
C15 C16 C11 120.2(2) . . ?
C13 C12 C11 120.7(2) . . ?
C16 C15 C14 120.3(2) . . ?
O24 C25 C27 107.7(2) . . ?
O24 C25 C26 105.5(2) . . ?
C27 C25 C26 113.1(3) . . ?
C13 C14 C15 120.0(3) . . ?
C12 C13 C14 119.9(3) . . ?
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 C7 1.216(2) . ?
O18 C19 1.392(2) . ?
O18 C22 1.397(3) . ?
O9 C4 1.357(2) . ?
O9 C10 1.430(3) . ?
O29 C22 1.204(2) . ?
O28 C23 1.206(3) . ?
O24 C23 1.332(3) . ?
O24 C25 1.461(3) . ?
C1 C6 1.394(3) . ?
C1 C2 1.404(3) . ?
C1 C7 1.470(3) . ?
C7 C20 1.516(3) . ?
C6 C5 1.384(3) . ?
C20 C21 1.354(3) . ?
C20 C19 1.438(3) . ?
C19 C17 1.344(3) . ?
C4 C5 1.393(3) . ?
C4 C3 1.395(3) . ?
C21 C23 1.467(3) . ?
C21 C22 1.470(3) . ?
C2 C3 1.373(3) . ?
C17 C11 1.441(3) . ?
C11 C12 1.392(3) . ?
C11 C16 1.401(3) . ?
C16 C15 1.380(4) . ?
C12 C13 1.382(4) . ?
C15 C14 1.386(4) . ?
C25 C27 1.492(5) . ?
C25 C26 1.509(4) . ?
C14 C13 1.385(4) . ?
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
C6 C1 C7 O8 -170.41(19) . . . . ?
C2 C1 C7 O8 7.9(3) . . . . ?
C6 C1 C7 C20 8.1(3) . . . . ?
C2 C1 C7 C20 -173.60(18) . . . . ?
C2 C1 C6 C5 0.9(3) . . . . ?
C7 C1 C6 C5 179.28(18) . . . . ?
O8 C7 C20 C21 -94.3(3) . . . . ?
C1 C7 C20 C21 87.2(3) . . . . ?
O8 C7 C20 C19 88.1(2) . . . . ?
C1 C7 C20 C19 -90.5(2) . . . . ?
C22 O18 C19 C17 179.2(2) . . . . ?
C22 O18 C19 C20 0.6(2) . . . . ?
C21 C20 C19 C17 -179.3(2) . . . . ?
C7 C20 C19 C17 -1.3(3) . . . . ?
C21 C20 C19 O18 -0.7(2) . . . . ?
C7 C20 C19 O18 177.32(17) . . . . ?
C10 O9 C4 C5 6.1(3) . . . . ?
C10 O9 C4 C3 -173.73(19) . . . . ?
C19 C20 C21 C23 177.4(2) . . . . ?
C7 C20 C21 C23 -0.5(4) . . . . ?
C19 C20 C21 C22 0.6(2) . . . . ?
C7 C20 C21 C22 -177.32(19) . . . . ?
C1 C6 C5 C4 0.4(3) . . . . ?
O9 C4 C5 C6 179.11(19) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C6 C1 C2 C3 -1.7(3) . . . . ?
C7 C1 C2 C3 180.0(2) . . . . ?
O18 C19 C17 C11 -1.8(4) . . . . ?
C20 C19 C17 C11 176.6(2) . . . . ?
C19 O18 C22 O29 -178.3(2) . . . . ?
C19 O18 C22 C21 -0.3(2) . . . . ?
C20 C21 C22 O29 177.5(2) . . . . ?
C23 C21 C22 O29 0.6(4) . . . . ?
C20 C21 C22 O18 -0.2(2) . . . . ?
C23 C21 C22 O18 -177.08(19) . . . . ?
C25 O24 C23 O28 4.4(4) . . . . ?
C25 O24 C23 C21 -176.0(2) . . . . ?
C20 C21 C23 O28 -178.4(2) . . . . ?
C22 C21 C23 O28 -2.1(4) . . . . ?
C20 C21 C23 O24 2.0(3) . . . . ?
C22 C21 C23 O24 178.3(2) . . . . ?
C19 C17 C11 C12 -179.5(2) . . . . ?
C19 C17 C11 C16 -0.3(4) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
O9 C4 C3 C2 -179.8(2) . . . . ?
C5 C4 C3 C2 0.4(3) . . . . ?
C12 C11 C16 C15 1.7(4) . . . . ?
C17 C11 C16 C15 -177.6(2) . . . . ?
C16 C11 C12 C13 -0.8(4) . . . . ?
C17 C11 C12 C13 178.5(3) . . . . ?
C11 C16 C15 C14 -1.3(4) . . . . ?
C23 O24 C25 C27 84.3(3) . . . . ?
C23 O24 C25 C26 -154.7(3) . . . . ?
C16 C15 C14 C13 0.0(5) . . . . ?
C11 C12 C13 C14 -0.5(5) . . . . ?
C15 C14 C13 C12 0.9(5) . . . . ?
